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There are, of course, many great ways to get high.

Thanks to seeing Requiem for a Dream as a teenager, I’ve stayed away from the hard kind. I prefer to create my own hallucinations, thank you very much.

But there are plenty more legal, and certainly encouraged, ways to get high. And for me, none better than the drug of validation and status.

Oh damn, that’s some good shit.

As you all know by now and no doubt think about all the time, I used to be a Pretty Big Deal. Respected, admired, and even hated in that special way someone gets when they’re successful while also young and way too obnoxious. I advanced quickly in my career, faster than most, which offered me a swift and significant dose of the greatest of all drugs: prestige.

Big titles? Great. Impressive accomplishments? Even better. My enemies admitting they were wrong about me and that I actually am quite impressive? Well, one can dream, can’t they.

People looked up to me and wanted to recreate my journey. People looked down at me and wondered: “WTF is this kid doing here?” It’s the latter kind that really got me high; in fact, it might be my Ikigai.

So when all the status and validation and ego got ripped away when I stepped away from the corporate world nearly 3 years ago, I lost that buzz. And now, I’m feeling the lingering effects of that status-bender.

I’m hardly the only addict. You know the type: the many who need to maintain the high.

The guy who’s been successful for years—could probably coast, maybe even step back—but can’t. He needs that next deal, that next $$$, that next room where people know his name.

This guy doesn’t even know who he is unless he keeps chasing the rush.

Or the woman who keeps reaching, who says “after this next thing, I’ll be good.” After she makes partner. After her next bonus. After the <whatever>. There’s always one more hit between her and peace. She thinks, only then, for once, she’ll feel done.

She won’t.

But you don’t need big ambitions like this to get hooked. Only a few dreams and some intermittent reinforcement here and there does the trick. Don’t pretend like you don’t know what I mean…

For anyone who’s been through a major life transition, professional or otherwise, you know what it feels like to lose that high, willingly or not. You know what it feels like to have built up something, maybe even something great, putting in all that goddamn work, only for it to do you no good now that you’re here.

In my own transition, I’ve passed the initial “lostness” feeling—the emptiness that comes when you have no idea where you’re going. But this new stage I’m in, a second hangover, really sucks.

And I want that high again.

To catch you up to date: over the last year, I wrote my first fiction novel and am now trying to get it published.

The writing of the book: fulfilling.
The selling of the book: humbling.

Here’s how I know I’m still in a state of withdrawal: I crave validation in my new “mountain” immediately. I feel guilty when I relax, like I’m being watched. And I still want my old colleagues to think about me.

(Do they think about me? Why don’t they think about me? I don’t ever come up? Not even once?)

It’s like I’ve come to peace with losing my prior status, only to wish I had new status in this new domain.

In the writing world, no one cares that I used to be a Pretty Big Deal. They don’t care if I helped build a $2B+ company (yeah, BILLION!), or a lot of people reported to me, or I did talks at conferences, or was a Senior Vice Peasant, or whatever.

On top of that, while creative endeavors help satisfy the intrinsic motivations, they do little for the extrinsic ones. There’s no money in this game and I’ve conveniently timed this transition to coincide with a surge of AI slop into the market. Just great, Rick!

The most likely outcome of my art is irrelevance.

Jeff, who built/sold a 9-figure business and walked away from it, nailed this when I interviewed him:

“When you get to where I am, it’s time to embark on a second hero’s journey. But the catch is all the things you learned before are gonna work against you now.

Because the dragon’s already dead. So now it’s different. Your sword does you no good at all.”

I want my book to be read. To be loved. To make lists and win awards and get optioned by Netflix. It doesn’t matter that none of this is likely… I still want it.

And hey, I’ll just take one of those hits, man. Only this last project. Please?

My prior prestige-filled-network? Does me no good in this new world, though this moment is exactly when some network/reputation would help most. I wrote a dark, intense post-apocalyptic story with a psychological bite. You know how many people from my old world care to read something like that?

Consider this:

100 people used to report to me. Now, I’m not sure if 100 people will read my book.

I’m no longer a Pretty Big Deal. I’m a Nothing Deal.

I know what I’m supposed to say here. This is the part of the essay where I show you I’m now enlightened, that I’m above all this nonsense, and here’s how you can be too. Something like: “I’m a nobody, and that’s okay.”

Not this time. Not today.

I’d be lying if I said I don’t still want a dose of that old drug. Just one last hit of validation, one last high on this project and I’ll be done. I promise.

Tomorrow, I quit. Today, I get high.

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The Way of Work is a newsletter for mid-career professionals who are successful on paper, but suspect work can’t deliver what it promised. This is part of the series, How to Be Irrelevant: on creativity and identity after the hunger to be impressive wears off. A few good ones:

• Why I didn’t write another self-help essay and wrote a novel instead

• The joy of having zero New Year’s resolutions

Or if you want to know where the addiction started:

Fiction lies. But what if it brings us closer to the truth?

I remember the first time I read The Lord of the Rings. In fact, I remember exactly where I was: on the living room couch inside an old red cottage on Keuka Lake, NY. For some strange reason, I listened to a Limp Bizkit album while reading (my parents probably didn’t approve). To this day, 25+ years later, the rare times I hear any song from Limp Bizkit, like My Way, I think of The Lord of the Rings… just like Tolkien would have wanted.

The best fiction stays with you.

Then there’s The Road, by Cormac McCarthy. I remember exactly where I was for that book too: in my studio apartment in the dark basement of a building in Foggy Bottom, DC. The place had this massive picture window that looked out at dumpsters and rat traps in the alleyway. I took down the whole book in one sitting, by myself, one Sunday evening 16 years ago. I can picture the room, the lighting, everything.

Meanwhile, I have a hard time remembering my wife’s phone number.

Years later, I re-read the book after becoming a father, and woah, the story hit with a whole new punch. I remember what the dad and son found in the locked basement of that one house (if you read it, I’m sure you remember it). But most of all, I remember when they were chased and the dad pushed the gun into his little son’s hand, “Take it, he whispered. Take it.” And then, “If they find you you are going to have to do it. Do you understand? Shh. No crying. Do you hear me? You know how to do it. You put it in your mouth and point it up. Do it quick and hard. Do you understand? Stop crying. Do you understand?”

The best fiction stays with you.

Of course, it’s all make believe. Little more than a fairy tale. Two random guys imagined some things that most of us would dismiss as crazy if they didn’t put it down in ink on a piece of paper and get a corporation to print it out. To the productive side of you? This, and all make-believe, is just a bunch of nonsense. The trivial illusions of a child. Detached from reality. No hard, practical facts or skills that make your life any better in any definitive way.

In other words: what’s the point?

No doubt, I’ve read some great non-fiction that certainly helped. Nietzsche was formative during my quarter-life crisis. Ernest Becker shaped a great deal of my worldview. Alan Watts came to me at the perfect time. More recently, The Second Mountain helped me reinvent myself after I left the corporate world (and I highly recommend that book to this crowd).

There’s something about the nonfiction frame — the implicit promise to the reader that we’re dealing with facts, real experience, actual takeaways — that makes their lessons feel more legitimate, while fiction alternatives feel indulgent, escapist, and useless.

But while the best nonfiction helps you, the best fiction stays with you.

Fiction is just way more fun, too, isn’t it?

Think of the classic philosophical thought experiment: is any of this real or are we living through a simulation? Sure, you can read what some crusty, old philosopher says about it — I’m sure some weirdos enjoy that sort of thing (hey, I’m not judging). But what about exploring this question… with AWESOME GRAVITY-DEFYING MOVES from The Matrix. “Hell yeah!” I guarantee you remember Neo dodging bullets better than you do Descartes’ theory of the thing-a-ma-jober.

Now, all this isn’t why I actually started writing fiction. The real reason is far less sexy. I’d been writing non-fiction (let’s be honest: self-help essays) for about a year and half when I started to get a bit bored. I’d tapped my available experience and wasn’t interested in dredging around the depths of my psyche to find new material.

Said simply: my life is quite boring.

And that’s totally fine! In fact, I prefer it that way. But it doesn’t exactly generate new material in the same way were I (see: What it feels like to get blown up) or you know, anyone else living a far more interesting life.

No, my reason for writing fiction had much more to do with: “I’m bored, let’s try something new.”

But it wasn’t until I really got into the story that I realized there was something bigger here. The whole process consumed me. The flow states hit harder than a Limp Bizkit song. Daily, the story pulled me under in a way I’d not experienced before, maybe in a way that some might call, dare I say, a “calling” (a word I try to stay away from).

More unexpectedly, through creating a story, I was also able to hit new ground. There’s something special about fiction, as both the writer and the reader, that allows us to access places deeper than we ever thought we could go. You can go there — wherever “there” might be. While non-fiction deals with the truth, it’s fiction that can sometimes get closer to the truth by not being constrained by it.

How so? Well, in my essays here, I don’t flinch away from topics like meaning, identity, or ambition, and I revel in the chance to poke at conventional wisdom. But what about the stuff underneath that? The stuff that even I don’t want to say out loud?

What about my fear of death? Not the abstract philosophical kind, but the specific, visceral fear that I will leave my kids before I’m ready or they’re ready? That one day they’ll become adults with lives of their own, and whatever I was to them will slowly blur, and then I’ll be gone. And soon after, they’ll be gone too. And the memory of me, of them, will be erased, like chalk washed off in the rain, vanished as if never here, slipped quietly into the eternal empire of the forgotten.

Sorry, but nonfiction doesn’t cut it here.

And I bet you can name a story that hit you in a way that no accurate, practical, grounded nonfiction book ever could.

The best fiction stays with you.

Now, I’m not claiming that my debut novel will come out of the gate and shock the world. It probably won’t be considered “the best fiction ever” (though if you were to say that, I wouldn’t stop you; and it’s not like I’m gonna decline the Pulitzer). And when I consider all the time I spent writing fiction, compared to the thousands upon thousands of people who’ve read my nonfiction writing, it’s likely that far less people ever read my book.

Also, my novel could flop, and I could be accused of adding to the slop. I could torch my hard earned reputation, which I increasingly seem desperate to light on fire. Or worse, no one will care… forgotten even before I’m gone.

After all, art’s most likely outcome is irrelevance.

Even still, there’s something, something special about fiction that, in the end, is worth the try. Maybe some day, one kid, a punk like I was, will pick up my story and feel something he hasn’t felt before. It’s not likely, but it’s possible. It’s possible I’ll help him access something he couldn’t have found on his own. Maybe it’s a stranger. Maybe it’s one of my own.

I won’t be able to explain things to him with a perfectly logical argument delivered through an old, forgotten newsletter post. No, the topic’s too deep and the essay would be way too boring. Instead, it can only be accessed through this story that I’ve created. One that isn’t real, that isn’t my own story, but also, really is my story.

And years later, after he tastes success but it feels flimsy, after he’s exhausted every bit of self-help advice he can handle, after his ambition runs dry, then maybe, just maybe, like me, he’ll too decide to give fiction a try.

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The Way of Work is a newsletter for mid-career professionals who are successful on paper, but suspect work can’t deliver what it promised. This is part of the series, How to Be Irrelevant: on creativity and identity after the hunger to be impressive wears off.

Essay 1: The joy of having zero New Year’s resolutions
Essay 2: How to be creative (without being a “creative person”)
Essay 3: The best work is work you’d pay to do

Essay 1: The joy of having zero New Year’s resolutions
Essay 2: How to be creative (without being a “creative person”)

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Most people think the best work is work that pays you a lot of money. They’ll say:

“Get paid to do the thing you love!”

Well, here’s my outrageous counter-claim:

The best work is work you’d pay to do.

Wait, what?!?

Yup. I think the “best work” is not only work you’d do for free, but it is so good that you’d be willing to spend your money to do it.

I know, I know… I can already sense the eye-rolls and/or groans. But bear with me because this thought experiment may be useful to you too.

Money is good

Every so often, someone will come to me with an offer that sounds like cheating:

“We’ll pay you a lot of money for little work.”

Side note: the cruel irony of a career is you get more of these offers the less you need them.

And my first reaction is still quite primitive. I’ll think about the check. The number of commas (hopefully). I’ll think about what that check can buy. I’ll access that enormous backlog of “things to purchase,” and without much effort, find a few new things to add too. It’s so easy to envision the value money brings; the clarity is powerful enough to split the heavens.

Let me be clear: money matters. Money is good. Obviously.

But at the same time, I also know, deep down, there’s a price to be paid for that money. It’s not only what I get, but what I give: the time, stress, status, and identity at play. Money is the world’s most effective way to warp your decisions; it’s the anesthetic that covers up pain and the bribe that makes bad work look really good.

Given this same offer, you may take the money. Fine. Many times, that’s what you need to do.

But I’m willing to bet there’s a point where, no matter how good the money is, the work makes your stomach turn. I bet there’s a point where you wouldn’t sell your soul (e.g. human trafficking or investment banking). Or certain kinds of work you wouldn’t be willing to do (e.g. cleaning septic tanks or enduring the politics necessary to get your budget approved in a large co).

I know this. You know this.

But it’s never black-and-white, is it? No one ever hands you a clear this-or-that decision. Instead, it’s a whole bunch of gray. So how can you detect how much money is seducing you into the wrong decision?

Use money to invert its signal

If you really want to find the best work, you may be better off thinking about your options across a different continuum:

Run this test on your work (not only your full-time job, but everything around that). Ask yourself: “would I do it for free?” and even, “would I pay to do it?”

While the framework may seem absurd on the surface, it’s the ultimate clarifier. It shows what you value. It shows when you’re using hush money for your conscience or subsidizing a life you don’t respect. It may also clarify what you’re missing and need to find.

How do I know this continuum exists? Because I’ve lived through every step myself:

Two years ago, I didn’t know the last 2 levels on this continuum even existed. My concept of “work” was highly restrictive. Now I like writing so much that I’d do it even if it never makes me a dollar (I even expect to lose money from it). This is not meant to induce jealousy or “look at me, my life is so great!” It’s just evidence — from one former workaholic — that there are other forms of work worth taking seriously.

For the best work, you’ll have to pay

Don’t confuse this with an argument to quit your job or an argument about financial independence, as if your dreams come true as soon as you become free (I’ve written about why this isn’t true, extensively). And no, this isn’t a way to reorganize your life tomorrow.

Maybe you need the money, even if it’s not the “best work.” That’s most people. But if you can name the thing you’d pay to do, you can start moving toward it, even slowly. Or maybe you have no idea yet — in that case, keep searching.

Because if you want the best work, you will pay. Somewhere, somehow. Maybe not directly, but you’ll pay in:

• Sacrificed earnings — taking less money to do something that matters more.

• Flexibility — buying back time or lowering your stress so you can focus on higher-value work.

• Status — stepping off the impressive track to do something that feels truer.

• Comfort — choosing something harder but more important.

So no, there’s no version of “the best work” that’s free or coming to save you with a bag. Instead, find the thing you’d pay to do. That, in my opinion, is where the best work lives.

Disagree? Feel free to debate in the comments.

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📖 Book Update: My debut novel is finished! Ten beta readers have completed it (including 4 that I met through this newsletter - thank you!), along with feedback from a professional editor. One reader described it as:

“[An] edge-of-your-seat post-apocalyptic thriller that had me crying [from a book] for the first time since sophomore year of high school — a must read.”

I’m now weighing publishing options, so it’ll be some time before it reaches a broader audience. If you want early access updates as this next phase unfolds, you can learn more here:

Learn more about the book

Or if you haven’t already, check out my last post in the series:

See you next time,
Rick

This is my 2nd essay in my new series, How to Become Irrelevant: A guide to not being a big deal. The first was nice and controversial: The joy of having zero New Year’s resolutions

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So you want to make something original? Something new and fresh and cool?

Well… too bad.

Because you’re not a “creative person.”

Sorry, you’re just not the type of person that does that kind of stuff. No, you’re a realist. Sensible. Practical. And all those “creative people” are weird, dreamy-eyed hippies who hate capitalism, wear scarves indoors, and waste their lives while calling it work.

So stay focused. Stay useful. Stay (most importantly) employable. And never, and I mean never, do something that’d embarrass yourself in front of people you don’t like.

Sound familiar?

If you’re already overflowing with ideas and constantly shipping them, congratulations. If you’re already in touch with the creative inside, if it hasn’t been stamped out of that dull husk of a human you’ve become, good for you. I’m not here for you today.

I’m not a “creative person.” I never liked art class. Don’t draw. Don’t paint. Never wrote stories for fun or even liked English Class. The only vaguely creative thing I did as a kid was play trumpet in high school, and that was because of a music requirement.1

All this led me to believe:

“Rick, you’re a practical man. Go and do boring things with your life.”

So I did. And it was fine. For a while.

But <insert midlife crisis>, I’ve come to realize I’ve fenced off entire regions of experience. Whole rooms I’ve locked, because I’d decided “that’s not me.” So when I finally picked up something really creative for the first time at the age of 40 (writing fiction), the real question was: “am I even allowed to try?”

A month later, the surprising answer:

“No, Rick. You shouldn’t try.”

No, no, no. That was the first answer. What was the later answer? The one that came after working through all the muck behind-the-scenes, enduring months of questioning. Oh, yeah it was:

“Yes, you can do this.”

So here’s what you can do to anoint yourself, just like I did, as an official “creative person”…

1. Don’t create new ideas, follow existing ones

Okay, sit down and think really hard of something original. C’mon, do it.

Did it work?

Okay, maybe try sitting in a coffee shop with a copy of The Creative Act next to you. Now, do it.

Still didn’t work, did it?

Right. Because ideas don’t arrive like that. I certainly don’t know where they come from. Neil Gaiman says his friend gets them from a little idea shop in Schenectady. Then he says the real thing: idea people are just trained to notice when ideas appear.

The same happened for me. My novel didn’t start as “I have an original concept fully thought out.” I barely had any idea where it would go. Instead, it started as a sequence of unglamorous “what ifs” that I followed:

• I like writing, but have only written essays. What if I tried a novel?

• Okay, I like post-apocalyptic stories w/ deeper themes. Let’s start there.

• My favorite book is The Road. I can picture the setting, the mood, etc.

• Now, how about: what happened to the kid in The Road after the book ends? Where does the kid go from here?

That last question became page one. Page one evolved into ten pages. Then, a few months later, my first draft was done.

And, here’s the key thing: I never knew I had that story in me.

2. Stop outsourcing your imagination to others

Conventional advice says:

“Read more.”
“Listen more.”
“Study the masters.”

Or in your world it may be:

“Follow the competition.”
“Learn from an expert.”
“Do more research.”

It’s trying to solve creativity with a constant stream of other people’s ideas. Meanwhile, your own brain never gets a chance to cook up something new because you’re following everyone else’s recipes. In fiction, it’s escaping into other people’s worlds, but never creating your own.

Rather than researching “how do I write a book?” then locking myself away for a few years studying, maybe take a course, maybe get a coach, reading, reading, reading… I just started writing. Then after my ideas were flushed out on the page, I went back and studied how stories are formed and went back to tweak my original creation.

So try this: create first, study later.

3. The best ideas show up on the 5th try.

Or 10th. Or 20th. You won’t know when they’ll come.

When I started my book… it sucked. Like horrible stuff no one would read. I was somehow ashamed of what I’d written, while also being the only person to have read it. (how is that possible?)

But I went through it over and over again. Deleted bad ideas. Added new ones. Kept writing more. And then, finally, the really good ideas appeared.

This is annoying. I wish it were easier. But also, it’s freeing to know you don’t have to have great ideas out the gate. You don’t have to kill your initial bad idea because, hey, it might get better.

4. Make something that doesn’t matter

Nothing will kill your ideas faster than the following practical concerns:

• “How will this make money?”

• “Will so-and-so think it’s stupid?”

• “How will I explain this to people I don’t like, at a party I don’t want to attend?”

It’s all different forms of the same question:

“Will people love me?”

WHOA!

Or, wait, I mean, let’s not get too far out there…

The main question, the more grounded one, you’re circling is:

“Is it worth it?”

It’s the sort of hardcore triage most adults get good at in life to eliminate the unnecessary. And I get it. It’s a valid question. But when it comes to creativity, you only find out the answer to that question later.

These practical concerns are all idea killers and toxic for early creativity. If you want more ideas, you need more low-stakes experiments and projects that are allowed to be pointless, private, and unimpressive.

When inspiration strikes, it’s best not to question it, just follow it to see where it goes.

5. Understand the rules, then break a big one

As you try something new, you’ll invariably run into different commandments:

• In business: “Set goals.”

• In life: “Don’t blow up a good thing.”

• In fiction: “Make your main character likable.”

Here’s the problem with rules: they’re often just patterns that worked for someone else in a different context. They’re average advice for average outcomes. (and they’re probably the same boring crap that AI will develop in massive quantities; i.e. not original)

Similarly, I got the advice from a writing coach who read my manuscript: “you can’t have your character do <this frowned upon thing>.” It was generic advice, the kind you’d see if you were to skim YouTube videos for an hour.

Here’s the thing: I know it’s a rule. And I choose to break it anyways.

Doing something original usually means, by definition, breaking a rule. And maybe the rule is right — but there’s only one way to find out…

6. Only you decide what “creative” means

The minute you make something original, your brain will immediately start looking to judge it relative to some impossible standard. Specifically: “is this creative to other people?”

No, it’s probably not. And most people probably won’t care. What’s “creative” to you, is “cliché” to others. Someone else will always be more creative than you, and you’ll never get there, and down and down you go.

But you don’t avoid exercise because you’re not a professional athlete. You don’t avoid thinking because you’re not a philosopher. You don’t tell your kid not to paint because they’re not Picasso. And it’s hard to know if what you’re creating is creative until the end.

Being “creative” is not a badge you’re even granted, it’s not some universal credential someone gives out. So if I’m the one who originally called myself “not creative,” then I’m the only one who can reverse the curse.

7. Last: Don’t read listicles.

The only thing less creative than reading listicles is writing them.

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Want more on the creative transition?

I was recently on the podcast by , and it turned out to be one of the best conversations I’ve had about this whole identity shift. At least read the written summary, which stands alone and is worth your time.

A few highlights:

• Why the best work is work you’d pay to do

• The unsexy reality of how creative work actually gets funded

• Why I’m not latching onto my shiny, new identity of “writer”

Available on: YouTube, Spotify, Apple, or wherever you get your podcasts.

Let’s say you’re tired of the same-old at work, but not so naive to think you should just quit-and-follow-your-dreams (terrible advice unless you’re the one person it works out for).

Rather than believing a new, shiny job will fix your problems, or that you’ll need to wait until retirement to finally do what you want, it might be worth considering a new item on the menu: the portfolio career.

is one of those people who’s experimenting at work’s edges. She’s been deconstructing “the jobs of a job” and rebuilding those pieces again through a new way of working, not only for herself, but advising others looking to make the same type of change.

Her way is one that doesn’t discount the value of an income (kinda useful), but creates the flexibility, accountability and experimentation that so many successful people want in a next step.

I invited Iwana here to talk about why work is evolving toward portfolio careers, and why you might want one.

Iwana is the first entrant to my new series, Alter Egos; honest accounts from real people who are trying to push work past its limits.

- Cheers, Rick

👉 P.S. If you’re interested in this topic, I urge you check out her writing at After Work. She’s one of the few people I recommend following.

Afterwork

Exploring the future of work and helping you shape your own. How technology disrupts not only jobs but also identity, purpose and life itself.

By Iwana Johannsen

From Jobs to Portfolio Careers to Portfolio Lives

The full-time job has long been the center of work and life. It shapes how we spend our time, how we earn money, and how we make sense of ourselves. None of us knows exactly how work will evolve in the coming years but we can all feel that something is changing. That our narrow definition of work may no longer fit the world we’re moving into.

Is it the end of work? Probably not yet, but it may be the beginning of the end of the full-time job as the dominant container through which work is organized.

A hint of what’s coming is already in the air: a world where ‘fractional’ might become the default, not the exception. Where people mix multiple roles, projects and income streams into portfolio careers.

Could the path ahead not be from job to job, or even from job to freedom, but from full-time jobs, to portfolio careers, and eventually to portfolio lives?

That thought has been circling my mind for a while and it’s the one I want to explore more deeply here.

Our Definition of Work

For a long time, I didn’t really question what we mean by work. Like most of us, I treated it as shorthand for paid employment: the job, the role, the title on a LinkedIn profile. For decades, the full-time job became the primary container for our time, energy, and attention. It absorbs most of our waking hours. Life is structured around the job, and everything else has to squeeze in around it.

But that narrow definition excludes much of what actually keeps our lives, and society, functioning. Care work, relationships, learning, tending to our health, contributing to society. All of this requires real effort, time, and energy, yet rarely counts as ‘real work’. We’ve learned to treat these activities as secondary, something to fit in around the edges of what’s considered productive. This is exhausting and it undervalues everything we do that keeps society alive, connected, and compassionate.

We’ve internalized the idea that value only shows up on a payslip. We’ve built a society that runs on invisible labor and then organized identity and security around the one form of work that pays.

So isn’t what we define as ‘work’ overdue for a massive reframe, for one that makes room for the full human experience?

The Job is Losing its Monopoly

What I’ve been describing is not necessarily new. The flaws of the system have been visible for a long time. What is changing now is the speed and the convergence of forces hitting the full-time job at once. AI, automation, and robotics are driving the cost of knowledge and labor toward zero. Tasks that once required whole teams are now being absorbed by technology, breaking traditional jobs into smaller components. As work becomes more modular, companies are increasingly hiring for projects, part-time, or fractional roles rather than permanent positions. A shift accelerated by digital platforms, the need for specialized skills on demand, and the desire to remain flexible in volatile markets.

Apart from that, the full-time job was never able to meet all our needs in the first place. We are multi-dimensional humans, yet industrialisation pushed us into ever narrower forms of specialization. Instead of chasing a perfect job that delivers income, meaning, security, creativity, and impact all at once, people break this bundle apart and reassemble it on their own terms.

And as work becomes more fragmented, modular, and unstable, people have started reorganizing themselves with a new model.

Portfolio Careers as a Transitional Model

Portfolio careers are a pragmatic response to these shifts. Rather than relying on a single full-time role, it combines different forms of work and income streams into a deliberately designed mix. That might include part-time or fractional roles, consulting, creative projects, digital products, services, or volunteering. Some parts generate income. Others provide meaning, learning, or connection. Together, they form one coherent working life.

There’s also the practical dimension. By diversifying work across multiple sources, people become less dependent on a single employer, more resilient to change and better able to adapt as industries shift. Instead of putting all your eggs in one basket, you spread your bets.

In practice, portfolio careers can take many forms. Most combine stable income streams with more exploratory work.

In my own case, I currently split my week between a fractional marketing role for two days, which covers the basics, one day writing on the future of work, and two days focused on portfolio career mentoring and further developing my offerings. Alongside this, I deliberately set time aside for investing, continuous learning, and contributing to the local climate community. Others assemble different components around the same logic.

My friend Fiona works fractionally in customer success at a tech start-up while teaching yoga and building products and services around her work on overcoming insomnia among high achievers. Her current split is roughly 30% fractional work, 20% yoga, and 50% focused on insomnia-related content creation, coaching, and digital products.

Many actually transition from a job to a portfolio career by developing a side project alongside a job and then gradually shifting the balance over time. It’s a way to experiment without jumping off a cliff building skills, confidence, and optionality as you go. Importantly, portfolio careers are not static. They evolve with life stages, interests, and responsibilities. Workloads scale up and down. Components are added, paused, or dropped. That flexibility is precisely the point.

Lately, I’ve been thinking that portfolio careers may not be the end of the story, but a transitional model. A practical way of navigating the gap between the collapsing world of jobs and a more self-authored way of working and living.

Portfolio Lives: Beyond the Job as the Centre of Life

For decades, the job has shaped how we allocate our time, define success, and decide what counts as valuable. As that structure weakens, something important becomes visible again: much of what keeps life and society functioning was never absent but it was clearly pushed to the margins.

Seen in this light, the shift toward portfolio careers is not just a labor market adjustment. It is a first step toward recalibrating what we value. A move away from treating paid employment as the sole legitimate form of work, and toward recognising the full range of activities that sustain a meaningful and resilient life. A larger shift from organizing life around a job to organizing life around a portfolio: of work, care, relationships, health, learning, contribution.

It’s understandably hard to imagine life without jobs at the center. For most of us, work has been synonymous with survival, structure, and legitimacy. But once AI and automation performs most labor better, faster, cheaper, and safer, we may be forced to confront a new reality. One where questions of identity, contribution, and meaning can no longer be outsourced to employment alone.1

As Rick Foerster points out in this article, this is not about abandoning ambition or productivity. It’s about taking a more deliberate, multi-dimensional approach to life that doesn’t collapse identity into a single role, but allows different sources of motivation and meaning to coexist and evolve over time.

The example Rick shares of how his own portfolio has shifted across life stages makes this tangible. It’s not a rigid framework or a calculated formula, but a living composition shaped by circumstances, priorities, and personal values. Just like a portfolio career, a portfolio of life is never finished. It adapts as we do.

The transition from full-time jobs, to portfolio careers, and eventually to portfolio lives won’t be easy. But rather than being abruptly pushed into a post-labor future, it could offer a gradual way out of job-centered living.

That pace matters. Not just economically, but especially psychologically, because the hardest part will be letting go of identities, routines, and measures of worth shaped by decades of job-centered living.2

Navigating it will require new forms of guidance - culturally, politically, and personally. But if we get it right, it may also be our best chance to build a society that values what actually makes life work.

Afterwork

Exploring the future of work and helping you shape your own. How technology disrupts not only jobs but also identity, purpose and life itself.

By Iwana Johannsen

Postscript from Rick: Iwana is the first entrant to my new series, Alter Egos; honest accounts from real people who are trying to push work past its limits. Stay tuned for more guest posts and interviews

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I gave up on my goals. And maybe you should too.

No resolutions last year. Zero again next year. And, I’ve gotta say, it feels fantastic.1

A few weeks ago, I also sat down to write an end of year reflection. You know, try to jam a coherent narrative on top of an arbitrary bracket of time. Maybe come up with a few lessons learned over here, a few important-sounding achievements over there. Summed up in a tidy plot to make it all make sense.

There’s no need for that.

The desire to control one’s fate is universal. Studies show this, probably. And the delusion of control hits its peak at New Year’s, when we reluctantly admit we’re deeply flawed, and need to do something about it.

So we hastily throw some ideas on paper, commit to real change this time (cause last time, there were <excuses>). But does it work like that? For anybody?

If you genuinely need change, and this arbitrary bracket of time motivates you… then please, do your thing. But be careful of deceiving yourself. Again.

What you “should” do

Resolutions sound like one of those things we should do. Year-based goals are what serious people do, right? If you don’t have goals, I mean, what are you even doing with your life?

Companies set goals like this. Teams set goals like this. And as we all know, that’s worked out beautifully for everyone involved.

For some people, maybe the structure works. Maybe you need more pressure. More self-torture and anxiety and pushing-and-pulling at yourself until you tear yourself to pieces. I did that too, for a while. So it could work for you.

But as one guy who’s been living life without goals for a while now, I gotta say, it’s way better on this side.

Here. Just give it a try. C’mon. Your parents won’t find out…

I used to have an intense, categorized, color-coded spreadsheet that looked something like this:

Sure, I like making progress. I’m still oriented toward certain outcomes, like having a vague sense of whether I’m healthier or not. But I don’t worry too much about the details. And I don’t write down my goals explicitly anymore.

You may point to my circumstances, saying I’m increasingly detached from the real world. Fair! But I stopped resolutions and personal goals a while ago, even back to when I was part of the traditional working world.

I’ve found life is much better when you stop pretending you can impose your will on everything. When you stop over-structuring and just live, goddamnit.

Accomplishing big things without goals

At the beginning of 2025, I never set out to write a book. Certainly not fiction. And yet here I am, and I did the thing. It became my main focus of the year. Accidentally.

Would a resolution or goal have helped? Of course not. If anything, I would have set some other goal and missed the real one entirely.

Should I have a goal this year of getting it published? Maybe. I’ll work toward it, but like most hard-to-do things, it’s impossible to know how long the process will take. So why set a goal of 12 months, when it could take 18? Am I worse off if it takes 18?

I think there’s a superstition buried in most high-achievers that without constant self-punishment, we’ll wake up as average people. That ease is dangerous and pressure is the only thing holding everything together.

Let me be clear: if your work has goals/objectives, please fulfill the requirements of your job. Please. I built the whole OKR system at my last company, set goals for my team, and aligned goals across a matrixed org. I get it!

But do you really need to double down with goals in your personal life? Does that really help your life get better?

Boxes upon boxes

The more I embrace this directionless-ness, the better I feel. It brings me back to something I wrote early on, in How to stay out of their box (in your career):

The world is desperate to put you into a box and most of us are more than willing to comply. It’s the label(s) by which they can define you…

Boxes can be good for you. They create a container for people to understand your value… And they create guardrails for you to operate within…

Boxes can be bad for you. If you want something else. If you want to move around. If you want your work (or life) to be diverse. If you like to try new things and learn new subjects…

Resolutions and goals are more boxes. They prevent serendipity and evolving interests and emergent opportunities. I’m now an anti-box person. They make me feel claustrophobic.

So no, 2025 wasn’t a year of tidy resolutions or conclusions. It was a year of more searching, questioning, and admitting I don’t have nearly as much figured out as I once pretended. And weirdly? I’m cool with that.

Some people need structure. I apparently need the opposite.

Who’s with me?

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Best posts of the year

Most Popular

People love swearing in headlines + a clever Shawshank Redemption reference.

Most Controversial

After 2 years of “freedom,” I had to disagree.

Most Discussed

Why you should buy the red convertible… then crash it on purpose.

Most Loved Series

Interviews with people who hit “enough” and discovered a whole new set of problems after. V2 may come out next year (but I’m not setting any goals about it). If you know someone who I should talk to, let me know.

My Favorite

This one’s closest to the core of what I’m exploring. How the collapse of old meaning systems doesn’t shrink our lives; it expands the frontier.

Oldie

I was honored when bestselling author of The Wealth Ladder, , included this post in his Favorite Investment Writing of 2025.

If you’re interested in my upcoming book and want to be on my super-special, ultra-secret early-access list (updates, sneak peeks, maybe a free copy), you can find out more here:

Learn more about the book

UPDATE: The response to my book-completion announcement floored me. So many of you offered to “beta read” that I had to cap the group just to protect my sanity. But if you want to be on my super-special, ultra-secret early-access list (updates, sneak peeks, maybe a free copy), you can find out more here:

Learn more about the book

(one early reader finished it in <24 hours saying “it sucked me in.” Another said, after a twist: “I can’t believe you [spoiler] like that… You got me.”)

Over the course of the Existential Explorer series, I’ve tried to explore the edges of the map while on one man’s search for meaning. I’ve argued in favor of a midlife crisis, warned against the successful-and-miserable trap, and — my most controversial take — pushed back on the idea that freedom is the highest form of wealth.

And folks… I did it. I figured it out.

I figured out the meaning of life.

Yup. Solved.

Which is why I’m launching a new course: “10 Easy Steps to Flip Your Life from Miserable to Meaningful.” It’s a bargain at $9,999. I mean, can you even put a price on meaning? If so… is it higher than that? Please let me know.

…

Okay, I’m done. I’ve shilled plenty of nonsense in my life, but you know you should be skeptical of anyone selling “simple solutions to existential dread” (excellent post on this by ). You won’t find meaning here, in a newsletter. You’ll need to find it out there, in the real world. Which brings me to my first stray rant:

Doing Meaning > Talking Meaning

I like to talk about meaning. Yeah, I’m a weirdo. I like how essential, yet slippery it is. And I believe it’s one of the most important frontiers for humankind we are missing.

But earlier this year, all of this talk screeched to a halt when I started writing a fiction novel.

I never planned to write fiction. Honestly. I like fiction, but never thought I’d be the one doing it. Then one Monday, I started writing a first chapter. (It sucked.) Tuesday, I tried again. Then Wednesday. Then—

2 months later I had completed my first draft.1

For those who don’t know, this is quite quick. Most people take years. But the ideas detonated in my brain. In fact, I had a hard time NOT writing. I was obsessed! I’d wake up early just to empty my head before it overflowed.

I’ve enjoyed writing work-ish essays over these last two years. But fiction? Damn. The flow states are on another level. Intoxicating even. Honestly, I can’t wait to get back to fiction after finishing this rambling post…

And this experience hammered home something simple for me: doing meaning is better than talking meaning.

Sure, I could research meaning in more depth, trying to become some Arthur Brooks-style thought leader Boomers seem to gravitate to. I’m sure the adults would approve. But that life sounds so… how do you put it? Oh yeah: boring.

I’d rather make things (even if they don’t matter). Explore. Push the edges of my creativity rather than intellectualizing every goddamn thing. You know, like, experience life.

Which leads me to my next point:

There’s a Fine Line Between a Calling and a Curse

My fiction obsession unleashed something I thought I’d already conquered: that old cocktail of burnout, frenzy, and work-identity addiction.

Obsession can be exhilarating. It also can be consuming.

I told you I started losing sleep. So was that good excitement over new ideas? Or unhealthy compulsion?

I struggled to sit through dinner with my family without scenes from the book popping into my head. It felt uncomfortably familiar to my old corporate wiring, with those end-of-day ruminations I could never shut off.

And for 2 of those 8 weeks when I finished my first draft, our family was on vacation. 😬 Make of that what you will.

I’ve seen this elsewhere too, in different forms. The concept of a “calling” morph into a slow-acting “curse” for many: entrepreneurs, doctors, nurses, teachers — especially anyone whose identity is fused with their output.

We want to fall in love with our work. We want to commit ourselves to something. We want to be all in.

But even gifts have shadows. And we need to be careful to control even the greatest of callings.

The fear of being ordinary after success

You know that I used to be kind of a big deal. You knew that, right? Cause if you didn’t, I’d be happy to share more about my—

Stepping into something brand-new, like writing (in fiction for god sakes) really makes you realize your exact level of relevance in this life. I mean…

• What if I’m no good at this?

• What if I never reach the same level of success?

• What if… (gasp) I’m no longer kind of a big deal?

One important fact the self-improvement culture bulldozes over: the world is filled with growth AND decline. Seasons. Death. You get it.

Life moves forward, whether we do or not.

And it’s easy to feel fulfilled when everything is clicking. When we’re growing. When the world feels like it wants us. When we feel accepted, respected and loved. But who are you when you’re not moving forward?

My last venture was a hit. But what if my work never reaches the same heights? Can I find meaning when things are moving backwards? These are all questions I’m trying to figure out.

Or maybe, I should hold out for posthumous success. Van Gogh, Nietzsche, Dickinson, etc. — geniuses who struggled in solitude only to have their work discovered after they were gone. This seems like a solid back-up plan.

Which brings me to the only answer that seems to help:

Don’t Keep Score

I’ve tried to stop measuring success relative to other people. All the metrics — money, title, or achievements — they’re not bad in isolation. But constantly compared against others? Exhausting.

Because the things that actually matter — meaning, love, connection, the Buffalo Bills finally winning a Super Bowl which isn’t looking like it’s going to happen AGAIN this year — don’t come with metrics. There’s no dashboard for this stuff.

The objective world is a terrible proxy for the subjective one. And when we excessively focus on the hard/easy-to-calculate measures, we crowd out the more important ones. You can have a brutal life and still make it meaningful. Or have every conceivable success and feel hollow.

“But— but— but Rick! You can’t manage what you don’t measure!”

Yeah, that’s the problem.

So I’ve stopped keeping score. The kind where I try to assess “how am I doing?” relative to where I should be. Trying, at least. My brain still wants to run the calculations, but I’ve committed to not to feed that machine no mo’!

For example, for my upcoming book, I’m avoiding any sales targets, awards, even whether I get a publishing deal or not. Sure I’d love all the above, and I’ll learn from what works or doesn’t, but keeping score won’t help and will suck away all the meaning and joy the process has brought me.

Instead, I’m focused on waking up, and making my meaning every day.

Meaning doesn’t need proof. Do you?

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Recommendations

A few things I’ve been enjoying lately:

• ’s special edition of The Pathless Path - It’s a beauty. If you haven’t read it, here’s your chance. And if you have, get it again. This guy keeps pushing the frontier for the rest of us. I, for one, am rooting for him.

• Tea After the Apocalypse by - I always love a fresh angle on the apocalypse (see mine). Then it’s got an ending that’s… 🤌🤌🤌

• Disposal by - Wow. So messed up in all the right ways. There’s no way to explain it. Just read it.

• & ’s Between Drafts Podcast - If you’re writing or publishing anything, these guys are invaluable trail markers. They’re living the journey ahead of me, and I appreciate anyone who charts their path for others.

UPDATE: Big news… I just finished my first book!

It’s the most original and probably coolest thing I’ve ever created. Even though it’s fiction, it wrestles with similar themes I explore here: meaning, identity, and staying human when the world is unraveling. I’m collaborating with a professional editor on the final draft and exploring the best path to publication (if you know an agent/publisher, hit me up).

👉 If you’d like to learn more or become an early reader (with a few special perks), find out more here:

Learn more about the book

The Way of Work explores stories of where we fit in the world of work. This is part of the Existential Explorer series. My last post was pretty popular (and stirred some debate):

Freedom is not the highest form of wealth

Do you remember the Loom founder from a few months ago who was rich, but felt lost? He came up on a podcast I was recently interviewed on.

His post went viral, after people had a lot of weird reactions to it:

We love stories like this because they’re vulnerable peeks behind-the-curtain of an important person’s life (by Western standards). They have something we really want ($$$), while revealing they don’t have all the other parts that we know actually matter.

Imagine if the post’s title were inverted: “I am poor and know what to do with my life”

BORING!!!

This piece also has the unique effect of confirming whatever you already believe:

• Money doesn’t solve big problems, or

• Money would solve MY big problems, or

• Work is the answer (keep working), or

• Work isn’t the answer (stop working), or

• You’re privileged, so STFU.

If you think I’m about to sympathize with the guy, that’s not quite the point of this post. Instead, I think all these reactions miss a critical piece of nuance:

We just witnessed a single point-in-time snapshot in a transition.

We didn’t get the full story. The before-and-after. A thoughtful retrospective after long-years of reflection. No, we got a single picture in the midst of a guy’s transition. It’s gonna be weird.

It’s like asking how I’m doing a few days after I throw my back out while putting on a sock. No, I’m not okay!

Or let’s say we sent you into the wilderness, and in mid-starvation, asked you to write a blog post about it. Yeah. How do you think that’d turn out?

Because if you’re in the middle of transition (rich or not), here’s the key part to know:

Being lost is the point. It’s okay. And it’s necessary.

One of the most counterintuitive lessons you’ll ever learn in a transition of any kind — job loss, death, midlife crisis, or just feeling stuck in general — is you have to go through the lostness before being found.

You’ll want nothing more than to get out of this feeling, to alleviate the pain ASAP, so you’ll take any option to avoid it. But in my experience, the trick to getting out of a gnarly transition is to live with it and not suppress it.

It’s one of those lessons that you’d really like to skip:

“Hey, I’d like to figure out my life and all, but how can I avoid that one really hard step?”

Instead, what do most people do: “Shut the hell up and get back to work.”

That’s what I almost did. I was an expert in suppressing my unease, shoving it back down where it came from, and getting busy again. I’m on like the 10,000-hours-level of mastery here, so I know what I’m talking about.

Maybe this founder guy, while awkward sounding, IS doing it right. Maybe he’s going to figure it out, it’ll just take more time. Maybe it’s okay what he’s going through. Totally normal, in fact.

Maybe disorientation doesn’t equal failure.

So, how do you “live with the lostness?”

(even assuming you don’t have the $$$ he has, but you’re still human and deal with human emotions)

Warning: these recommendations are going to sound so woo-woo, like I’m one step away from chugging some cyanide-laced Kool-Aid. But they’re, as far as I can tell, the truth:

1. Let the wildness phase stretch as long as you can, allowing yourself time to NOT have a thing figured out (i.e. no goals or deadlines to reverse engineer from).

2. Let opportunities emerge to you, rather than forcing yourself to take on opportunities (only respond to genuine pulls of interest/excitement).

3. Avoid grasping onto the “next thing” so urgently, aka the rebound (it may work, but you’ll likely become lost again).

4. Get into the lostness. Write about it. Talk about it. Take long walks. Do things to get out of your head and into your body. Do whatever you need, just stop trying to escape!

5. Optional: don’t share your feelings online during this phase.

If you want to find something genuine and intrinsic, and your life up to this point has been built on a cage of expectations, it’s going to take some time to get out. I wrote before:

Instead of stopping at the first off-ramp, with the need to define or distract, we replace trying to answer with asking. True exploration demands that you sit in the fog, and stay lost on purpose. It’s deeply unproductive, often lonely, maddeningly inconclusive. But it requires loosening your grip: on certainty, on speed, on the self you think you have to be. — from The Open Frontier of Meaning

That was pretty good actually. Did I really write that?

As I’ve shared before, I’m infinitely thankful I had the time and ability to disconnect — I wouldn’t have figured my stuff out without it. That’s why I hope to share my experience even if you don’t share my circumstance.

So go climb a mountain, write that self-indulgent blog post, and stop paying attention to the noise. Life isn’t a spreadsheet problem, where when all the numbers add up, everything turns out to be fine. It’s messy and you’ll have to embrace that mess if you ever want to “find yourself.”

Yes, you want to escape the wilderness eventually. No, you don’t want to be lost forever. But if you try to force yourself out, it likely won’t work.

And the most counterintuitive point of all may be: you don’t ever really “find yourself,” you just get more comfortable being lost.

🤯

So… will you give it a second?

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I go deeper about the Loom founder, limits of freedom, and lostness in my recent interview with Brendan Frazier, in The Human Side of Money Podcast:

🎧 Ep: The Dark Side of Financial Freedom No One Prepares You For with Rick Foerster (Loom founder discussion starts around 30:20)

I’m more open than ever in this one 👀

Today, I’m going after a sacred modern virtue. Tell me if you’ve heard this one before:

“Freedom is the highest form of wealth.”

A few examples:1

After 2 years of freedom, I’d like to disagree.

I don’t have issue with freedom as a form of wealth. Or that it’s a better form of wealth than money (it is). I only take issue with the “highest” or “greatest” part of this argument.

People who believe into this sort of thing tend to gravitate to a few modern cults: FIRE, solopreneurship, entrepreneurship = freedom, life in a cabin in the woods, the apocalypse as a fresh start,2 and people who think they can make money writing a newsletter.

It’s this deep desire and belief that if you can GET OUT of the system you’re in, you’ll live happily-ever-after.

I used to believe all this stuff, too. But then I got freedom. And I realized it wasn’t enough.

It’s not enough to have control of your time. It’s not enough to have options. It’s not enough to be able to “do what you want” because, in fact, it’s really hard to figure out and force yourself to “do what you want.”

And are you sure you know what you want, and when you get what you want will it be what you really want or will there now be something else in its place, and who says what you want is the best thing for you/everyone? etc. etc.

I know what all this sounds like: privileged whining. But I’m not here to generate sympathy for myself, and instead explain what is around the corner of that thing you’re chasing.

Before I go any further, I need to clarify something. I’m NOT saying any of the following…

• Money is bad.

• Having a lot of money is bad.

• Using money to buy freedom is bad.

• Freedom is bad.

Can we move on?

Yes, it’s great to have freedom. But then, guess what, you have to fill it. It’s like:

“Awesome, I made it! This is so great!”

Then, immediately followed by–

“Okay. Now what?”

It’s a problem you can barely understand when you are not free. And it sounds like one of those problems you’d like to have. But rather than finally being able to “do what you want,” you are more likely to:

1. Feel completely unmoored when all your old motivations are gone.

2. Run away from one bad boss to a worse one (i.e. yourself).

3. Jump quickly back to the old thing that made you feel safe/valued/loved/etc.

4. Go on an existential-sized rebound, doing stuff like ayahuasca-retreats in the mountains.

Oh, and here’s a bizarre thought that I guarantee enters into the mind of most people with freedom (at least once, though it can be recurring):

“Was I better off before, when I wasn’t free?”

So, what do I think now, after 2 years of freedom?

I think that freedom, like money, is just another means to an end. It’s a milestone, not an endgame.

I now believe that meaning is the highest form of wealth.

The ability to continually have and make meaning, every day. To feel a deep sense of fulfillment and purpose in our actions; emphasizing what we do more than who we are. To feel like it all makes sense; there is a coherent narrative about the world and our place in it.

The good news is you don’t need money for meaning (though it can help). There’s plenty who never find freedom, but still find purpose. So wait, does that make them free? And having freedom without meaning is its own kind of prison.

Here’s another captain-obvious angle: relationships require dependence. I’m not truly “free” as long as I’m a father. Or a husband. Or a citizen. Or a mentor. Or have any projects/commitments whatsoever.

True fulfillment often requires commitment → which limits freedom → but grants meaning. Even love requires dependence. 😱

Oh, but you think: “I just want freedom from work.”

No. You don’t!

You want fun, meaningful projects and activities with people you like, on your own terms. You want to help people you like. You want a healthier relationship with better boundaries. What you really want is to expand the definition of work beyond the narrow conventions you think are available to you. Or maybe you just need a nap.

Or maybe what you really want is to transcend death in a metaphysical form, but woah!, that’s way too heavy.

This freedom business is really about the freedom to choose our work (and our sources of meaning).

Ironically, the pursuit of freedom gives you meaning, but once you obtain freedom, it loses its meaning completely.

To someone who is not free, this all sounds so dumb.

But it’s like being sick: all you want is to be not-sick. At the same time, you know that being not-sick is not the highest form of health. There’s longevity, strength, energy, physical autonomy, and so on. So why do you think the same about being not-free?

I think this modern obsession with freedom comes down to something else:

The quest for freedom is the assumed cure for a society devoid of meaning.

In plain English: our life is meaningless, so we think freedom from our circumstances will somehow fix things.

But even if we can become free of tedious pointlessness of our modern lives, we may finally realize something else: we now need meaning.3

Freedom is a beautiful escape. But meaning is what makes freedom worth it.

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Next up, why you need to sit through the hardest part of any transition:

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The Way of Work explores stories of where we fit in the world of work. This is part of the Existential Explorer series. A few suggestions to start:

Part 1: From Businessman to ‘Existential Explorer’
Part 2: The Open Frontier of Meaning
Part 3: What You Need is a Midlife Crisis
Part 5: just kidding… work actually is the meaning of life!

Check out my other series, such as The Other Side of Enough (when you have enough).

Subscribe now

Mastery without meaning, is still meaningless.

Tell me if you’ve heard this one before:

“You should pursue mastery, because in mastery, you’ll find: satisfaction/purpose/money/etc.”

Another variant of it is:

“Find something to get good at first and that will turn into something you love over time.”

Except, well… sometimes, it doesn’t.

The world values mastery. People who go above and beyond to excel at something specific. We like to do things we're good at, are valued, and challenge our skills forward. And it sort of helps when we make a boatload of money from it.

But what if the thing that makes you successful, also makes you miserable?

The Making of the Mask

I carried the pain in my face and my gut.

Before I get to that, allow me to brag for a second…

I built my career as an operator and builder, especially at the early stage of things. I was better than most at turning a new, ambiguous idea into reality. Some come up with ideas. Some take an existing process and improve it. I was damn good in between, building when an idea is just an idea.

And (sorry, some more bragging), the systems I built, helped a company grow from almost zero to a multi-billion-dollar public company.

Have I mentioned that I’m a very important and distinguished businessman who should be taken seriously?!

No, it wasn’t all me, nor do I believe I was the most important piece. Repeat, I got lucky. But (and I promise, here’s my last and ultimate brag) I’m convinced the company wouldn’t have been a success without me. Sorry, ain’t nobody gonna persuade me otherwise!

On top of all that, this was in healthcare! It’s not like we fixed the system (spoiler: still fucked up), but we nudged it in the right direction. It always feels good to make an impact on an obvious problem.

Doesn’t this all sound like the perfect setup for a rich and fulfilling career?

But man… doing the work was draining.

First, if you didn't know, startup operations doesn’t deal with “fun problems.” Instead, it’s continual firefighting. It has a way of putting you in a permanent state of high-alert – constantly scanning for the next failure, inspecting every little problem that could metastasize into a bigger catastrophe. It’s a job of anticipating what could go wrong next, which means living in constant future-based fear.

I also grew into a senior executive in charge of things, so people looked to me for answers (sorry, still bragging). People problems, bad metrics, products failing, unhappy customers, you name it… it had to be handled.

And I was pretty good at it.

But I was wearing a mask, and my face knew it. I would end each day with tension under my eyes and across my forehead. Like I had been flexing my face into an acceptable expression: keeping calm during stress, performing optimism, reassurance, authority, competence. All. Day. Long. Torn up on the inside, but unable to express it on the outside.

Where did all this tension go? I swallowed it. From The Value of Disappearing:

“I was an expert in plowing through unease and overcoming obstacles. I could always outwork my problems. Suppressing distracting questions, and shoving discomfort back down where it came from.

‘Shut the fuck up and get back to work!’”

I didn’t let go of the stress, I ingested it. And it sat like a ball in my gut. I didn’t even realize it was there (or that it wasn’t normal), until I finally released it a few months after leaving work, almost 2 years ago.

Sounds horrible? Well, this persona also got me money, validation, relevance, power, security, status. The success was so good, I never stopped to ask if it was good for me.

And why would I question it? I was getting promoted. I was getting paid. People admired me. I was praised for my competence, leadership, and ability to fix things. Caught in the momentum, “liking something” wasn’t even allowed to be a question.

What? Like you would have turned down the rewards? The pain, in retrospect, even to me, seems like a fair trade. I mean, isn’t that just the nature of work? Suffering is required.

It wasn’t until I left that I could even ask the question: “do I like what I’m good at?”

The Trap of Competence

I don’t believe I'm entitled to perfect work (see Fulfillment FOMO). Nor do I have illusions about what the market requires of me. But, and it’s taken me a while to understand this, what started as a skill, turned into a track, and then into a trap.

It sounds so obvious looking back, but during the doing, I had no idea. I needed the distance myself to see the truth:

1. I didn’t choose my skill set, I fell into it.

2. I got good at something early, which was reinforced by others.

3. I leaned further into what I was good at.

4. And so on in a cycle.

I never fell in love with the work, I just adapted to it.

Success is a great servant, but a terrible master. It builds expectations, income, status – a weight that you need to keep pulling. Like, okay man, you’ve built your house. Now go live in it forever.

And didn’t I have a duty to others? To use my skills and experience in a problem area (like healthcare) for the good of others? So what if “I didn’t like it?” Boo hoo, poor, selfish, Rick!

You see, this is a kind of success that’s hard to walk away from because no one else thinks it’s a problem. Like what if Superman didn’t like superman-ing and instead, wanted to be a musician? I doubt everyone else would think that’s normal, let alone be okay with it. As one mentor explained to me:

“What do you mean you don't want to use your superpower?”

And boy, I was so close to going back to using it. But a nagging feeling stuck with me that something was not right.

Did I truly like what I do? Or was it more about the ego, social status, and approval that convinced me that's what I “like?”

Did I want to become a master at my old skills? Or try something new?

Did I have a duty to that old world, one of obvious problems and impact? Or did I have a different duty to the world? A higher calling that I hadn’t understood yet?

I’m reminded of my interview with Marlo (from Rich, Powerful, and Ready to Quit):

“It goes to the core of, who do I want to be?

Do I want to be this turbo executive, stressed out, pressed for time, but achieving and accomplishing in a business sense? Or do I want to be a more thoughtful, engaged person?”

Glimpses of Alignment

If I was better at paying attention, I would have noticed that, deep down, I actually loved certain types of work. The times where I broke through the day-to-day noise, and entered into moments of depth, truly in the zone.

In that space, my work could create something transcendent.

One simple example… I worked with a colleague on a slide that would depict the customer’s journey, including some future-oriented stuff no one had seen before. It was a few days of heads down work, closing my office door, shutting out the world, and thinking.

What we created ended up connecting the dots on everything we had built to date. It shaped our company strategy going forward. It was a primary way we pitched ourselves to customers and partners. And it was featured in our company’s IPO as a core explanation of our strategy.

Calling one slide “transcendent” may seem like hyperbole. But that’s what it felt like.

On the surface, I was a startup operator, adept at fighting fires and inching the business forward. But my real power, or more precisely what fueled me, was as a creative thinker in solitude. Someone who could create clarity out of chaos.

And isn’t that what I’m trying to do here, at The Way of Work? Maybe on another wavelength or at another altitude. What is writing if not sitting alone, wrestling with a messy problem, and turning it into something (hopefully) elegant and useful?

The work was hard and draining. But burnout, for me, had a lot more to do with chronic suppression of the work I really wanted to do.

Some might say: “what about giving back? What about all that high-impact stuff you left behind?” Sure. But is my suffering required to give back? Is there not some other purpose that I can pursue? A higher duty that doesn’t require sacrificing my soul?

No doubt, I’d rather have success over no-success. I’m no saint. And I’m so grateful for the part of the story where I got the reward. If I hadn’t received that pot of gold at the end of the rainbow… man, I’d be in a different mental state now.

And I’m not sure bypassing the rewards would have been the answer either. Success can be an enabler, if you do it right. Maybe I had to be miserable, so I could be not miserable now. Maybe I needed to go through all of it to figure myself out. So no, I don’t regret any of it.

But for me at least, the greatest trap isn’t in doing something I hate. Because if I hate it, I’ll do something about it. The trap is when I do something that I’m good at and rewarded for it. Because that situation locks me in: comfortable, successful, miserable.

Mastery without meaning is still meaningless.

I’ll end with Sara Pendergast, the consultant-turned-artist, who is pursuing mastery at a depth that’s rare (from Waiting Decades to Finally Follow Your Dreams):

“Unlike the hollow expertise I developed during my corporate career, the mastery I pursue now feels very rich and rewarding. It helps me explore why I exist at all and allows me to connect to others in ways that feel very natural.

What is it in life that means something to me? What catches my eye? Why do I think about what I think about? All of these things I can't describe, but I might be able to create a visual language for showing what they are and what they mean to me.”

📚 Further Exploration: Open: An Autobiography, by Andre Agassi
⍰ Question: do you like what you’re good at?
👀 Next up: what really is the highest form of wealth?

The Way of Work

Freedom is not the highest form of wealth

UPDATE: I’m posting less (and more off-the-cuff) because I’m working on an awesome, yet kinda secret, but increasingly less secret, project. There’s a hint hidden in today’s post (hint: it’s not that hidden…

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8 months ago · 7 likes · 4 comments · Rick Foerster

🙏 My Ask: If this essay meant something to you, pass it along, ❤️ or 🔄.

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The Way of Work explores stories of where we fit in the world of work. This is part of the Existential Explorer series:

Part 1: From Businessman to ‘Existential Explorer’
Part 2: The Open Frontier of Meaning
Part 3: What You Need is a Midlife Crisis
Part 4: Total Addressable Meaning
Part 5: just kidding… work actually is the meaning of life!

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In the absurd, we may find meaning.

I’ve always wanted to write for The Onion. Ever since my parents bought Our Dumb Century, I’ve envied their ability to say something blatantly ridiculous, and still land uncomfortably close to the truth. Spoiler: my thesis is that’s how passion projects work, as well.

Here’s a classic example:

Another fun fact is that in high school I received the superlative “Most Sarcastic.” Other people got stuff like “Most Likely to Succeed” or “Best Smile.” Instead, I got one of the throwaway categories. It’s probably like winning an Oscar for “Sound Mixing.”

But honestly? I still consider it my proudest achievement. More than any professional or personal succ…

Sorry, honey, I mean you and the kids are my greatest accomplishment!1

That partially explains why I went off the deep-end last week and wrote an offensive, heretical satire about the meaning of life told via an afterlife bureaucracy. Even though it was absurd. Especially since it was absurd.

I know it may land me a spot in Hell (supposedly a tight community btw). But it was worth the price (though I may regret it later for an eternity). Maybe my mom, a retired pastor, can put in a good word for me. Because Very-Serious-Artists like yours truly must push the boundaries of convention, speak truth through our craft, blah blah blah... while others look on uncomfortably wondering: what’s wrong with him?!

Here’s the point: I tried something I’ve been wanting to do for a long time. It was a tiny, little thing. A project within a project. Something utterly pointless that probably goes nowhere.

But it gave me life! That’s the paradox: sometimes the more absurd it seems, the more meaningful it can become.2

I made no money (in fact, I lost a few confused readers). And a prestigious publication, like The Onion, hasn’t called me (yet). Apparently, I’m the primary audience for my own jokes. But I still had more fun writing it than most things I’ve ever done. And it opened my eyes to new opportunities – maybe I’ll write some more fiction or more failed attempts at humor. Who knows.

At some point, you need to realize that no one will recruit you to do your own thing.

No one asked me to start a newsletter. No one asked me to dig into meaning. And no one asked me to write about a performance review in purgatory, making nuanced, yet undoubtedly clever critiques about our work-oriented society.

That’s the point, folks.

The Way of Work is my passion project. It will probably never be a financial success; though for some reason, me making money from it would validate its existence to you. But it allows me to do all sorts of weird stuff: examine my past, explore the edges of the map, talk to interesting people, and, occasionally, screw around.

Maybe the truth lies a bit outside the obvious and into the absurd. Things that may seem like they barely matter on the surface can be, in fact, exactly where we find what matters most of all.

Why you need a “Passion Project”

I’ve written before about how meaning is an open frontier — something we’re no longer handed, but now have to seek and shape for ourselves.

If I could prescribe one step to anyone feeling stuck, hollow, or burnt out, it would be a Passion Project. One way to stake your claim in the unknown.

Not a sabbatical. Not a career pivot. Not a startup. Just a project. Something weird, small, and unnecessary… except to you.

I think a lot of people, like me, need a place to put all the peculiar stuff bouncing around inside their heads. A passion project gives it somewhere to go; a place to channel what feels like excess energy. And it can be one of the most tangible first steps toward finding more meaning in your life.

Yes, I know how this sounds: privileged and preachy (the worst combination). “Must be nice!” But stay with me.

During my own messy transition, I received some advice from a mentor, Anne Loehr.3 Her brother created a coffee-table book profiling immigrants in America. It was a passion project, one thing within a busy, accomplished life as a lawyer and professor.

The lesson was this: I didn’t need to find that singular, all-consuming purpose that would propel me through the rest of time. Instead of putting enormous pressure on myself to answer vomit-inducing questions, like “what is the meaning of life?” I could simply ask myself: “what's a project I’d like to try?"

And so: The Way of Work was born.

Meaning won’t make itself

What I’m calling “passion projects” is what we typically call: “hobbies” or “volunteering.”

Unfortunately, our culture treats these things as optional or indulgent. The kind of thing that’s nice to do… if you have time.

But for many people, they’re the only place where they feel like themselves. It’s the thing no one asked them to do, that no one’s grading them on. While the rest of our lives are filled with obligations, passion projects are an outlet to let the real you breathe. One of the last places people can feel alive and express something that feels real. For some, it may even be the first place they encounter true meaning outside of work.

For me, that includes poking around strange topics most others won’t touch (see What You Need is a Midlife Crisis), and exploring them from a new lens – whether that be from an alternate perspective, or even, in the case of last week’s adventure, an alternate reality.

And here’s where I take a hard right turn away from what everyone else is selling: don’t expect to make money from a passion project (at least for a while). Influencers corrupt the concept by turning every passion into a monetizable hustle. The seductive promise of: “turn what you love into passive income.”

Yeah, right! Selling you on a dream is their passion project.

I also used to believe that if something didn’t make money, it didn’t really count. Not kidding. It was a dumb mental block that prevented so much progress across so many domains. My brain would go:

“Pursue a venture with zero money-making potential?
But… how will it be valued? How will I know if it’s working?
Aren’t I a serious businessman? Who am I if it doesn’t make money?”

Or, I believed, projects needed to be big and life-changing. Something impressive that would get strangers to care about me.

It’s taken my own exploration to realize that sometimes, the best things are the ones that make zero sense on paper. But they matter to you anyway. And in my experience, that’s where real meaning hides.

One small step for you,
one giant leap for meaning

One last story…

An old co-worker, Brian Tajlili, is a Very-Serious-And-Important Person. He’s a senior actuary at a health insurance company. It’s a great career, but no offense to Brian, it’s not the kind of thing they end up making a documentary about (unless he does something very bad…).

I’ll always remember Brian because he’s the first guy to ever coach me through VLOOKUP tables in Excel. Which, as I recall, I royally screwed up for a major client. Sorry again, Brian!

Recently, Brian tried his hand at speculative fiction. No, it’s not the first thing you’d expect from an actuary. But, to his credit, he submitted an essay into a contest… and won first prize. You can read his prize-winning story: Faulty Medication

The $400 reward won’t change his life or allow him to quit his job (at least, I wouldn’t advise it). But I’ll bet it felt good. A tiny, unexpected vote of confidence for trying something new.

Or maybe he’ll never do it again. That’s fine too. Not everything needs to become a career or lifelong passion. Can we stop putting so much damn pressure on everything?4

That’s the power of passion projects: one small, self-directed way to try something “pointless.” And, in the process, maybe find something meaningful.

Make it anyway

Let’s not lie to each other: passion projects often require resources that not everyone has. Of course you don’t have the time. Or energy. Or money. Or <insert whatever>.

I’m lucky. I could afford to launch The Way of Work without the need to make money. Yet. Eventually, I’ll try to monetize you. Especially the segment of my audience that buys Malcolm Gladwell books.

So yeah, you might discount everything I’ve said because I’m not you. But here’s a strange fact I’ve noticed as I’ve gotten older: few people, even in a place of security, pursue their own passion projects. They put them off, waiting until a day where they’re finally granted permission (they won’t). Or lose the fear (they won’t). Or can ensure their project won’t suck (it will).

Even people with all the resources in the world still find all kinds of rationale for not doing something they really want to do. I’m not saying everyone can do a passion project. I am saying more people could, and should.

Because I’ve found them to be one of the most powerful ways to access personal meaning. They can be a big, long-term commitment like The Way of Work is for me. In-between things. Or a side quest, like Anne’s brother or Brian.

This isn’t a pitch to quit your job. Or to throw away your life in search of reinvention. Just to try something. Anything… Join a band. Create an interview series. Restore an old home. Play board games competitively.5

It can sound stupid, or weird, or temporary, or too personal to share. But I guarantee you: no one will ever ask you to do it.

If it goes nowhere, so what? But if you’re lucky, it might become your own little award.

Like your favorite Onion article: a touch outside the obvious and into the absurd, but still, somehow closer to the truth.

📚 Further Exploration: For those curious enough to continue the exploration…

• The Myth of Sisyphus, by Albert Camus (how even in the absurd, we can find meaning)

⍰ Question: what’s a project you’d try if money didn’t matter?
👀 Next up: what if mastery doesn’t bring you meaning?

The Way of Work

How to be successful and miserable

Update: I been quiet lately because I’ve been workin on a SUPER SECRET PROJECT. It came out of nowhere and has claimed most of my attention. I’ll be posting less for a bit… but if you’re curious, stick around. I’ll share more soon…

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10 months ago · 5 likes · 1 comment · Rick Foerster

🙏 My Ask: If this essay meant something to you, pass it along, ❤️ or 🔄.

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This one’s a little different. Skip it if you get easily offended, don’t like to laugh, or are in HR.

Sometimes I like to switch it up, trying something new. Mostly because… I feel like it. Don’t worry, I’ll return to my serious and boring essays next week.

This is part of my Existential Explorer series. Last week was about building a life around what matters. This week is asks: “what if work really IS all that matters?”

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Bob stared at the Pearly Gates, immediately regretting his enthusiasm at that children’s birthday party. Bob had thought he wasn’t too big for the bounce house. Turns out, he was.

The gates ahead beamed a reflective glare, trying a bit too hard to look impressive. Next to them stood a man in flowing priestly robes, wearing a laminated badge.

I

Bob mumbled to himself: “Ah shit… Catholic.”

The Saint didn’t look up right away, he just sighed and flipped a page.

Saint: “What was that?”

Bob: “Oh nothing. Just was hoping for one a little more… sympathetic.”

Saint: “Well Bob, welcome to the afterlife.

The kids call it ‘Purgatory.’ Internally, we just call it ‘The Performance Review.’

Let’s get this over with, shall we?”

Bob: “Performance Rev-?”

Saint: “Yes, Bob. Every human is judged for their worth on Earth. Then we decide what to do with you after.

We soft-launched performance reviews down there to ease people in. But well… HR got a little carried away with it.”

Bob: “That’s for sure!”

He shuddered at the memory of one review that ended with his manager saying, “I’m not sure why you’re still here.”

Saint: “Well, let’s get started, shall we? Did you complete your Self-Evaluation?”

Bob: “Umm, I, umm… I must have missed that email.”

Saint: “Well, you can fill out the 47-page form on your own time. No one reads it anyways.

Let’s start with the first thing on the list: your number of hours worked.”

Bob: “Number of hours worked? Why is that important?”

Saint: “Right. Context. I always forget that part.

We just had a thought leader pass through recently. Gave the keynote at AngelConf. Big on ‘start with why.’

So now, of course, it’s a whole thing.”

Bob: “Start with-?”

Saint: “Yeah. Funny story…

When he was done, we sent him straight to Hell. Gave him a job in middle management. 50 direct reports. Zero decision-making power. Calendar is pre-booked to eternity with back-to-back meetings.

And we never told him why!

(chuckles to himself)

Honestly, there are perks to this job.”

Bob: “My God, that’s awful!”

Saint: “No, I’m not God. Common mistake though.”

II

Saint: “Anyway, back to the review. Let me explain what we’re doing here. You see, the meaning of life…”

Bob leaned in, now listening.

Saint: “...is work.”

Bob: “Work?”

Saint: “Yes. Your pure output. How much you produced while alive. Plus, any indirect impact that made others produce more too. The more, the better.”

Bob: “Work is the meaning of life?”

Saint: “Yeah. Paid employment, more specifically.

Think of humans as machines, built by us gods, because we like to see a range of consumable goods in the marketplace. I guess souls are sacred, but we prefer to think of them as our ‘greatest assets.’

You, humans, were our finest creation. Completely insatiable. Always producing. The other animals turned out to be basically useless.

We had to phase out the dinosaurs because without thumbs, they weren't going to be able to handle spreadsheets.”

Bob: “Wait, what? Slow down. I’m just trying to catch up here. You’re saying the greatest mystery in life… is work?

What about altruism? Compassion? You know… uhhh, all that other stuff we’re supposed to care about?”

Saint: “Nope. None of that mattered. Unless it helped you work more. Then, yeah, I guess it was fine.”

Bob: “But what about family?”

Saint: “Dude. We don’t care how many kids you have. Or even if you were around.

In fact, the less you were there, the better. Kids who grow up chasing unavailable approval? They outperform on their metrics, like, off the charts.”

Bob: “What about community?”

Saint: “Community? Ha! I’ll show you ‘community.’

Down in Hell, they’ve got a GREAT community! Nothing brings people together like suffering.”

Bob: “But… what about right and wrong? Good and evil?”

Saint: “C’mon man. We’re the Catholic Church. We’re fine with a few indiscretions!”

III

Saint: “Let me repeat: It’s. All. About. Work.

Haven’t you been paying attention? Damn. We sent all those hustle-bros down there to spread the word.

Look at Heaven. It’s filled with all the greats.

Did you know we have the first guy who ever replied ‘per my last email’? He’s a legend around here.”

Bob: “I don’t understand why all this comes down to work? I mean, there’s so much more to life than that!”

Saint: “Yeah, that was the idea. At least, for a while.

But all those supposed ‘virtues’ you were talking about? WAY too subjective. So squishy. Open to interpretation.

The angels kept arguing about it – couldn't agree on anything. There were power struggles. Everyone trying to protect their headcount. Even… ‘Alignment Meetings.’ Can you believe it? It got ugly.

Plus, when there were just a few million people on Earth, we could get away with judging everyone one-by-one. But once it got to be about, say, a billion people or so? Forget it. Completely inefficient. Couldn’t automate it either.

We even brought in a change management consultant. Nobody liked him though. So guess where he is now?

Anyway, that’s why we introduced Capitalism. Not just an economic system. A moral one.

Objective. Scalable. Looks great on a dashboard.

The rollout got delayed by the Dark Ages, but once we got it live… I’ll admit, I was skeptical, but it’s been a total godsend. No pun intended.

I’ve finally been able to spend more time on my harp lessons. You know, at least one thing for me…”

Bob: “But why would God do that?”

Saint: “Oh, well, the change was approved by the Board. God’s hand was ultimately forced by our primary shareholder.”

Bob: “Who’s that?”

Saint: “Goldman.”

Bob: “Fuckin’ Goldman…”

They nod in agreement.

IV

Bob: “By the way, I thought it was the Protestant Work Ethic, not Catholic?”

Saint: “Yeah. It’s THE one thing those bozos got right.

They figured out that if you blend work with religion, you can get people to do a lot of stuff they’d never do otherwise. So we threw in ‘enlightenment’ as a performance perk for upper management. Morale went through the roof.

But eventually, the system got overloaded. We needed a place to put all the missed potential, procrastination, and social media influencers.

We call it ‘Heaven’s Excess Labor Losses.’”

Bob: “You mean… HELL?”

Saint: “Bingo. Satan runs it. He’s a contractor. Unionized though. We don’t like to talk about it.”

There’s a long pause.

“Back to your file. Now, for this part, I’ve looped in Janice from Celestial Resources. Legal reasons. I’m sure you understand.”

Bob: “Oh, okay… hi, Janice!”

Saint: “No. You won’t hear from Janice. Trust me… you do NOT want to hear from Janice.”

He looks up slightly and shudders.

“As I said, let’s start with hours worked. First, I have to commend you on the number of hours you told other people you worked. Even if you only worked, say, half that – it’s still appreciated. The illusion of hard work keeps everyone feeling guilty about not working more.

So that was a good thing. But, on the other hand…”

Bob: “Wait. Are you giving me the shit sandwich?”

Saint: “You didn’t work as long as you could have. You did a lot of screwing around at work. And I don’t mean staying late for no reason, which is fine in our book.

I mean, specifically: your bathroom breaks. They went long. Like, suspiciously long. At one point, we were worried whether you were okay.”

Bob: “Well, I… I know I didn’t have the best diet.”

Saint: “Sure. But you know. And I know. And Janice definitely knows what you were really doing in there.”

Bob: “Uhhhh…”

Saint: “And it says here you stopped working at 61. You easily had 4 more years in you. C’mon dude. Those last few years could’ve really helped your case here.”

Bob: “Well, I’ve always wondered: what’s the significance of 65? It feels like an arbitrary number that has very little do with when someone should stop working.”

Saint: “Yeah, 65? No idea why, to be honest. It’s just what’s in the book.

I follow the book. You know what they say… complianceness is next to godliness.”

Bob: “I thought it was ‘cleanliness?’”

Saint: “Nah. The prophet screwed up the translation. Which is kinda annoying because we sent around follow-up notes after the meeting.”

V

Saint: “Alright, let’s look at the type of work you did.”

Bob: “I know Accounting wasn’t the most glamorous, but at least I wasn’t in Finance!”

Saint: “Funny you say that. Finance is the highest calling.”

Bob: “Finance?!”

Saint: “Yeah. You don’t want to be IN the arena, you want to be FINANCING the arena.

Ideally hands-off. Private equity. Shell corporations. Offshore accounts. That kinda thing.”

Bob: “But why?!”

Saint: “The tax benefits.”

Bob: “Oh.”

Saint: “You see, there is no higher calling than getting other people to work. It’s a form of passive salvation. It’s the type of stuff that separates the saints from the staff.

The second highest calling is Marketing.”

Bob: “Marketing?”

Saint: “Marketing is essential because we need to convert all this meaningless stuff into money.

It’s the sacred lubricant of economic production. Marketers get people to buy more stuff. Stuff requires money. Money requires work. And so on. The cycle repeats.

I mean, what is evolution if not a highly efficient system for moving inventory?”

Bob: “Wait… you mean like, we’re the inventory?”

Saint: “You’re finally catching on!

We move inventory via humans. You move inventory via work.

Bob, you were basically a SKU. Low-margin. Clearly upgradeable. But still, part of the supply chain.

And again, we’re back to the point of it all: output. It’s all very meta, I know.”

Bob: “What’s the third highest calling? HR?”

Saint: “Oh, those people are just as insufferable in the afterlife. They can skip the performance review and go straight to Hell!”

Bob: “Wait. Since you’re doing performance reviews, aren’t you technically in HR?”

Saint: “Careful now, Bob… Your fate across an eternity is in my hands…”

VI

Bob: “Fine. Whatever. Can we just skip all this BS and get to the verdict?

Damn, this is just like a REAL performance review! Everyone knows you’re supposed to lead with the decision, then backfill the rationale.”

Saint: “Alright, alright. No need to get pushy.

Now I’m starting to understand the comments section of your review…”

Bob: “Just tell me already.”

Saint: “Fine. After careful consideration. Taking into account all your direct and indirect output. Plus, a few points deducted for how annoying you’ve been today...”

He closes the file.

“It’s reincarnation for you.”

Bob: “Reincarnation? I thought you were Christian?”

Saint: “Yeah, we’re in the middle of a divine pivot.

Your assignment: Worker Bee.

Let’s show you what a lifetime of real work looks like. If you don't work a full day, your boss eats you.”

Bob: “Wait! Please. There has to be another option. I mean, I’ll do anything!

I’ll even… I’ll even accept a role as an unemployed newsletter writer.”

Saint: “To be honest, Bob, I didn’t even read your file. We just fed your data into a large soul model. It wrote the entire review on its own.”

The Saint leans in.

“Between you and me, I’m actually sort of worried about my own job. This new GPT-God 5.6 model really makes you wonder…”

Janice crackles over the loudspeaker: “Ahem!”

Saint: “Sorry, Janice! You can disregard that.”

Bob: “Are you done?”

Saint: “No, but you are. We went way over time. I’ve got 3 million more reviews to get through today. The dead just won’t stop dying…”

As Bob’s vision fades to black, a soothing synthetic voice chimes in…

“Thank you for participating in your Final Performance Review.

Your feedback matters to us. To help us improve the process for future souls, please take a moment to complete a brief survey…”

Bob, his voice faint and dissolving: “You’ve gotta be fuc—”

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👀 Next up: something far less fun, but also less embarrassing to my parents.

⍰ Question: if this made you laugh, cry, or want to put me through your own performance review, let me know.
🙏 My Ask: If you enjoyed this essay, pass it along, ❤️ or 🔄.

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The Way of Work explores stories of where we fit in the world of work. This is part of the Existential Explorer series:

Part 1: From Businessman to ‘Existential Explorer’
Part 2: The Open Frontier of Meaning
Part 3: What You Need is a Midlife Crisis

Also, check out my popular series: The Other Side of Enough (what’s life is like when you have enough).

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You wake up. Check your phone. Scan the headlines. Skim some work emails. Slog out of bed.

Another day. Another cycle of output. You’ve barely opened your eyes, and already you’re behind.

You’ve got things to do, people to reply to, progress to make. Productive, respected, maybe even successful. By most standards, you’re doing quite well.

And still, something is off. You’re moving through the world, but not really in it. Awake, but not alive. Wishing you were somewhere else, but not sure where. And maybe wondering: Is this it?

Of course, it’s not like you’re aimless! You’re trying to find work that matters. You want to make an impact. You want to do more than get by. So what’s wrong here?

If you’re lucky, maybe you can name it: you’re missing meaning. It’s a hard thing to define that can take many forms. Not just “happiness,” but a deeper feeling of being alive, connected, and part of a bigger story. It’s not something you can easily measure, but you know it when you feel it.

You’re not alone. I’ve felt it and so have many more. This disorientation to the world; a sense that life feels full on the outside, but hollow on the inside.

What if the problem is we’ve built our lives around the wrong center of gravity? That, in all our busyness, we forgot to seek meaning? And instead, we’ve been chasing its shadows?

Imagine: what if we stopped building our lives around markets, and started building them around meaning?

A world where meaning was at the center of life. Not markets, or money, or our relative place in the hierarchy. Where we stopped measuring life in terms of output or accomplishments, but moments that actually mattered.

(sometimes imagining a different world is the only way to see the strange one we’re already in)

School wouldn’t be a training ground for the labor market (not that it's even good at that). Or a place where we pound our kids with pointless facts. It’d be a playground for discovering meaning: a place to try, discover, and build a life that felt purposeful. Where children wouldn’t be asked “what do you want to be when you grow up?” but “what are you curious about?” Instead of over-engineering their days, we’d watch where they gravitate and explore.

Real meaning, after all, must be felt, not forced. Just as there’s no way to rationally convince someone to love another, we can’t thrust meaning onto someone without their own discovery.

Teachers, then, would be mentors, elders and artists, who could guide us on this pursuit, not bureaucrats who just comply with a broken system.

In this world, ambition is not extinguished, but pointed in a different direction.

We’d still work. But work wouldn’t be at the core, our default identity. Instead, careers would be one expression of meaning amongst many. Not ladders in a single direction, but landscapes with the ability to move and roam. Where meaning wasn’t an afterthought, squeezed into the margins of a career or what you do when your career is done, but what you do from the start.

We certainly wouldn’t confuse our economic system (e.g. capitalism), for a system of morality and meaning.

Companies and their leaders would no longer be our idols. We’d barely care enough to tune into one of their podcasts. Instead, it’d be community leaders, spiritual guides, teachers, and artists that hold the most social capital.

Meanwhile, writers with a small and mildly successful newsletter would sit at the top of the food chain. Okay, okay… that was a bit of a reach!

We wouldn’t need to advertise our experiences, turning everything into content. A walk in the park wouldn’t require perfect lighting and a few takes to make sure we recorded the right mood. In fact, we’d grow suspicious of anything too optimized, seeing them as performances of purpose, but not the real thing.

We wouldn’t try to monetize it all, turning hobbies into side hustles or relationships into transactional exchanges. In fact, we’d be resistant to financial incentives, as they’d risk leading us astray from where we felt pure purpose. Instead of orienting toward outcomes that add market value, we’d look to activities that make us lose track of time. Ones that involve, not just our head, but also our body and soul.

We’d consider the open frontier of creativity, community, philosophy, even spirituality. Acts of building, caring, moving, making. Showing up for something outside ourselves – a cause worth fighting for, a group worth backing, an activity valuable as an end in itself. We’d place higher value on transcendence, wonder, and awe; being one with a greater whole. Perhaps even new forms of meaning we haven’t discovered yet (or forgot along the way).

There’d be burnout too. But not from doing too much.

Instead, it’d be from forgetting why any of it mattered. Pointless busyness would be polishing the surface while the inside remains hollow. Recovery, then, wouldn’t be collapsing on the couch, phone in hand, scrolling with dead eyes. It would be a space for reconnecting with our search for meaning. Maybe we’d make more room for a weekly sabbath, occasional sabbaticals, and pilgrimages that reorient us back to what matters.

The measure of a good life would not be output, but depth. We’d worry less about doing more, and ask harder questions about what any of it is for. Instead of the arbitrary goal of “peak performance,” we’d pursue “peak purpose” looking for ways to realize the total addressable meaning available across our lives.

To be successful in this world would be to be fully awake. Where you’d breathe your last breath, and say “damn, that was a great life!” And maybe, most importantly, the ability to share meaning with others. (Now those would be the people we admire most.)

Paradoxically, we might not even talk about meaning (at least explicitly). Like happiness, meaning tends to happen when you don’t chase it directly. Instead of contemplating meaning, we’d be focused on doing meaning. And we’d conclude that theoretical thought experiments were a colossal waste of time (cough, cough).

Of course, even a world centered on meaning would have flaws.

We’d mess it up somehow, finding ways to corrupt it, commercialize it, and turn it into a performance.

There’d be Ikigai coaches, influencers peddling purpose, and so on. “Get meaning quick” instead of “get rich quick” gurus. Existential grifters. Maybe better than the bullshit they sling today, but still there.

We’d still fall for status hierarchies, envying those that are most fulfilled. Inequality would be: “why does she get to live a more meaningful life than me?”

There’d be over-optimizers, tracking KPIs and OKRs, turning meaning into a performance review. Well intentioned, but applying the wrong solution to the right problem.

There’d still be tribes organized around bundles of meaning, like today, selling us their templated version of salvation. Still a bit too enthusiastic about shoving their beliefs down on us. We’d find value in them, but stay vigilant about where they might lead us off course.

Maybe we don’t need to imagine this world.

Maybe this isn’t a thought experiment after all. Maybe, instead, it’s a distorted mirror. Showing us that we’re not ignoring meaning at all, but we’re already obsessed with it.

And we just really suck at it.

Maybe we already do try to live for meaning, just awkwardly, performatively, dishonestly. Like we sense what matters, but still filter it through the same metrics we think we’re moving beyond.

We hoard money, put our names on buildings, leave artifacts of our existence behind. We find ways to destroy their tribe while growing our tribe. What better proof of our validity than having our way win?

We spend our lives chasing the illusions instead, attempting to feel permanent through fame, productivity, and success. Our survival instincts, always inventing ways to leave something behind via symbols, to outlive a body that won’t last.

But maybe, instead of hiding behind these pseudo-meaningful masks, we’d be better off being honest about what we’re actually after. Pointing ourselves, intentionally, toward something real. Not fooling ourselves with the distracting illusion of meaning, but getting at the crux of meaning itself.

Is this just another unrealistic utopia?

A stupid thought experiment for over-thinkers?

Right now, the rebuttals may be blaring, starting with: “Rick, easy for you to say. You benefited from the markets, and are now free to pursue meaning.” Yeah, yeah, you got me. I do have space to examine these questions more than most. (Maybe that could be useful to you, if you think about it…). But I don’t think my circumstances let others off the hook.

In the future, meaning may not be a luxury problem reserved only for the well-off. (Though I’d argue it isn’t today, either.) If this all sounds indulgent or unrealistic, consider what’s coming: a future where AI upends our work, even whether we can or need to work at all. What then?

When markets no longer need us, meaning might be all we have left. The robots may take our jobs, but we’ll keep the existential crises.

What if we were forced to find meaning outside of work, outside of money, outside of markets? Would we still live the way we do today? Or would we finally be honest, and start pursuing a life around what really matters?

📚 Further Exploration: For those curious enough to continue the exploration…

• If work dominated your every moment would life be worth living?, by Jordan Taggart (heavy inspiration for this essay)

• Die With Zero, by Bill Perkins (similar case for “Net Fulfillment” > net worth)

• Denial of Death, by Ernest Becker (all the symbolic ways we try to outsmart our own mortality)

⍰ Question: if meaning was your center of gravity, how would your life look different?
👀 Next up: what if work was ALL that really matters?

🙏 My Ask: If this essay meant something to you, pass it along, ❤️ or 🔄.

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The Man in the Red Convertible

We mock the Midlife Crisis, but you may want to have one.

The “Midlife Crisis” automatically conjures up the picture of a middle-aged man, probably with a gut, wearing a shirt with too many buttons undone at the top, sitting inside a red convertible (leased, not owned), the strands of hair on a balding head flowing in the breeze.

Pathetic, right? Chasing status he’ll never have, youth that won’t return, approval he’ll never receive.

His dreams are dying. But they hang on for dear life in his head, unable to accept that certain roads may be closed for good.

Maybe he buys a leather jacket. Gets some Botox. Looks for a young fling to prove he’s still got it. Books a spiritual retreat to reinvent himself over a long weekend. Or maybe he just needs to start a newsletter. Some symbol to reaffirm that he still matters.1

Because the bills keep coming. The children are relentless. Obligations, endless. His marriage dulled down to the logistics. Hobbies? What are those? Life turned out to be harder, and way more boring, than he thought it would be.

Didn’t he do all the right things? Met life’s demands, strove for what he was supposed to? But the life he’s built, filled with nice things and important-sounding titles, all things he thought he wanted, now feels like a cage. Regretfully, it’s one he made himself. Inconveniently, it’s not one he can easily escape.

He may fantasize about running off to a cabin in the woods. Maybe even an apocalypse… something, please, to help clear a few things off his calendar.

And as if things weren’t bad enough, death is within view. He sees it in his aging parents. But no place more than the mirror: the accumulating midsection, the receding hairline, wrinkles around the eyes, aches all over. He’ll listen to one Huberman podcast, start binging on strange supplements, and sign up for a 10K (his knees, in no way are ready).

His life? Feels like a whole lotta nothing. One step after another, on the way to nowhere profound. His memory? Will be lost in the abyss of history. Forgotten even before he’s gone.

“I think I know him better than anyone here. This is a quiet, frightened, insignificant man who has been nothing all his life, who has never had recognition, his name in the newspapers. Nobody knows him, nobody quotes him, nobody seeks his advice... That’s a very sad thing, to be nothing.” – Juror #9, from 12 Angry Men

But underneath it all, there’s something else: the genuine opportunity for reinvention.

Maybe it’s not too late.

Crashing the Car

A few years ago, I accelerated myself into a midlife crisis by stepping away from a secure identity into the unknown. Crashed the car on purpose, it may seem.

I was told that at 38 I wasn't midlife enough to have a midlife crisis. Well, I’ve always been a bit advanced for my age 😏 — an old fart at heart.

Don’t worry, I’m not going to rehash my story again; you’re welcome to read about my rise and fall elsewhere. But here’s some new information: I contemplated starting a “midlife healthcare company” that was focused on the unique challenges of men and women in this life-stage. We’ve got pediatrics and geriatrics, then not much in between. The hope was you could exit midlife better off than you entered.

If you need the summary: midlife is a bitch. It’s more of a midlife crunch where pressure comes from all sides: work, money, health, family. You’re juggling needy kids and aging parents. Too many hours to pay off a crippling mortgage. Less energy despite more to do. It’s when you’re more at risk for deaths of despair (e.g. suicide, alcoholism, drug-overdoses), depression, and heart issues. Famously, this was synthesized into the “U-shaped curve of happiness,” where life bottoms out at 47.2 years old. Even apes, it turns out, show signs of midlife slumps.

For those of us in or approaching midlife… “FUCK!!!”

What may once have been thought of as a period of thriving – career on track, family coming together, secure in our identity, etc. – turns out to be a couple decades of doom.

But, as I’ve learned, the crisis of midlife is an opportunity for renewal. A fresh start before it’s too late. The unhappiness, overwhelm, and oncoming decline are shoves to step back and ask:

• “What have I done with my life?”

• “What have I been avoiding?”

• “What do I want with the time I have left?

These can be viewed as big, scary questions… OR necessary ones to explore before it’s too late. The crisis, if you’re lucky enough to feel it, forces you to stop.

Maybe it’s your health. Face it, you’re aging and things don’t get automagically better from here. But this is an opportunity, not to live forever, but to live well while it lasts.

Maybe it’s your peace. It’s time to stop pretending stress is the price of success. That if you keep going like this, your body might quit before you do.

Maybe it’s your relationships. The half-attention you bring to your partner. The way your kids are growing up in front of you, yet you’re still distracted. A chance to not just physically be there, but mentally present.

Maybe it’s your ambition. Good job, you’ve played the game well thus far. But now it’s time to build your own ladder, instead of climbing someone else’s. It’s time to clarify what success means to you, not someone else.

Maybe it’s time to start again. Not to reinvent yourself into something impressive, but into something more alive. More human. Shedding the inherited structures, the masks you put on, to rebuild your own.

Sometimes we need a crisis, something greater than the quiet hum of dissatisfaction, to make a change. “Creative destruction,” a period where old assumptions fall apart to make room for something new. It’s a necessary rebellion against outdated versions of ourselves. recently said it well:

Sure, our choices are more narrow now. We have less energy and more reason for caution. But that also brings clarity. There’s little time left and fewer lies we can afford to tell ourselves. A healthy sense of urgency seems like a wise move — this, right now, may be our last time.

Instead of starting that company, I chose the reckoning within. I refused to continue heads down, only to awake one day and wonder what I may have missed. I didn’t want my future to be a dull extension of my past.

Yeah, it sucked. I felt a special kind of fear, which I can only describe as a black hole in my chest. A vertigo that comes from standing at the edge of the void, only to realize the void is inside you. It’s one that shows up when you start asking yourself questions you’re not sure you want the answers to. Fun ones like: “What if I am nobody?”

Yikes.

And yet, somehow, that was still better than pretending everything was fine as is.

Instead of seeing it as a midlife crisis, I tried to reframe it as a “midlife reset.” Not a grand hero’s journey anyone will make a movie about, just a quiet rite of passage. A chance to reconcile my past and recommit to what mattered.

That old saying, “never let a good crisis go to waste”2 can flip the midlife malaise from something to avoid, to something to need.

Off Cruise Control

Let’s get back to our middle-aged main character…

Maybe he looks in the mirror and decides it’s time to change. He’ll never be ripped, but he starts adding back healthy habits, one-by-one (a little Botox couldn’t hurt either, right?). And he wisely skips the young-thing fling and decides to revitalize his relationship with his wife instead.

He picks up a hobby. It’s the guitar. Yeah, super cheesy, I know. But who the hell cares? Maybe he does start that newsletter (read it for christ’s sake!), content with a tiny following that will never make him a living, but allows him to explore ideas and meet interesting people.

He’s grateful for his success so far, but decides to define it for himself going forward. There are other mountains he feels he’s meant to summit. Maybe he doesn’t need to blow up his career, but he can make edits to make it more meaningful. He won’t work with assholes anymore (and tries to not be one). He accepts some drudgery, but inches further toward projects that interest him. Give back more, not just extract more. At midlife, he may have less time, but he has more leverage.

He reconnects with a few childhood friends and joins a new community. It’s a group of men his age who also like convertibles. Go figure! Maybe contentment can even be found in the cliché.

But the biggest shift is when he realizes there’s a layer beyond the tactical and practical edits. Beneath the surface-level momentum. It touches the ambient fear that, as he declines, the guitars and cars won’t save him from nothingness. That all this activity, switching from this to that, is still a mask.

And in embracing that void, something unexpected happens: he creates space to allow something new in. Call it “spirituality” or whatever you want. It’s a path he’s bulldozed over in the past. Maybe it’ll lead to nowhere. But it feels like an opening to something beyond himself. Where, for the first time, he may finally glimpse what really matters.

I’m not saying our main character pulls it all off. He’s unlikely to flip from pathetic to perfection overnight. But improvement could happen. That’s what the crisis offers: the catalyst for change while we still can.

When it comes to the “Midlife Crisis,” the real problem may be never having one at all. Postponing the dread with dull comforts. Quelling the unease with quick fixes. Until later, when there’s no time left.

Maybe it’s not too late. Not fixed, but now awake. And that might be enough.

📚 Further Exploration: For those curious enough to continue the exploration…

• Midlife: A Philosophical Guide, by

• what does it mean to shed your masks at 40. the jung theory., credit for sharing

• The Midlife Reorientation - a User’s Guide, by

• The Seasons of a Man’s Life, by Brett and Kate McKay

• Why men shouldn’t fear being “middle aged”, with and 3

⍰ Question: Have you had a midlife crisis? In what ways did it change you?
👀 Next up: what if life were oriented around meaning, not markets?

🙏 My Ask: If this essay meant something to you, pass it along, ❤️ or 🔄.

Subscribe now

The Way of Work explores stories of where we fit in the world of work. This is part of my 5th series, Existential Explorer, exploring the uncharted edges of who we become when we try to matter.

Part 1: From Businessman to ‘Existential Explorer’ – An attempt to explain what I’m doing

Also, check out my last series, Not Obvious (why work advice fails us) or The Other Side of Enough (what’s life is like when you have enough).

Subscribe now

Let’s get caught up: God is dead. We’re connected but alone. Work feels hollow. And most days, we struggle to form a coherent narrative about the events of the world, let alone our own lives.

We are freer than ever, and have no idea what to do with it. In the vacuum of meaning, we cling to substitutes, but their effects are thin and fleeting.

Meanwhile, we race to conquer new frontiers: AI, outer space, even immortality. We fund expeditions and issue grand pronouncements about the future. But we ignore the other frontier that sits closer to home: our search for meaning.

In the busyness of modern life, “meaning” doesn’t feel urgent. It feels abstract. Optional. A luxury problem.

You may not think about meaning when you’re busy. But you’ll feel its absence when you’re bored, broken, or burned out.

Without meaning, success feels empty.
Without meaning, productivity feels purposeless.
Without meaning, suffering feels unbearable.
Without meaning, freedom feels unmoored.

Meaning is the quiet sense that our life is coherent, that our days add up to something more than survival. And right now, it’s up for grabs.

The structures that once gave life coherence have eroded (“The Old World”). In their place, we hastily fill the void with quick but empty fixes (“The Now World”). So we have a choice: go back to the old, grasp for the new, or step into the wide-open landscape ahead, where meaning must be explored, not inherited (“The New World”).

This essay is an attempt to trace that collapse, the frantic grasping that followed, and the open frontier that remains.

Let’s get into it.

I. The Old World:
Collapse of Inherited Maps

Meaning used to come with instructions. You didn’t have to find it, you inherited it.

Not long ago, the question “what is the meaning of life?” didn’t feel like a personal burden. It was given to you, in prepackaged boxes with rituals, hierarchies, and hand-me-down beliefs.

The Old World offered maps. Crude, maybe. Incomplete, often. But they pointed somewhere.

You inherited a religion, which told you who you were and why you were here. It gave you a moral structure, a shared community, and a set of rituals to shake you out of distraction. This solved a lot of problems.

You chose a profession (or more likely, it was chosen for you). That career came with stability, status, and a story: a known path to follow, a sense that you were part of something. Work was identity, structure, contribution.

You belonged to a place. A neighborhood or church or club. There was a we to belong to, with others to share the journey. That place also shaped a collective narrative for understanding the world.

These maps weren’t perfect, but they worked. Consider that once, you had an answer to all the big questions:

• an explanation of the world and your place in it,

• a structure for creating purpose,

• moral guidance to keep you in line, and

• community to hold it all together.

Now? That scaffolding has collapsed, or, at best, has become optional. Religion is less a way of life and more treated like a lifestyle brand, as if the nature of the universe came down to one’s personal preferences. Religious participation is down, especially the organized kind. And even the devoted can agree that it's lost its cultural relevance, no longer at the center of defining our collective values.

Careers are volatile and uncertain. You're unlikely to spend your life doing just one thing anymore. Even more urgently, your employability comes down to your performance last quarter. And with AI, what work will even be safe anymore? How can you find meaning in something that might not be around next year?

Meanwhile, you’re more connected than ever, yet lonelier than ever. You may now find more friendship with pixels on a screen than people in real life. Or wait, was that a bot? And any collective identity has been replaced by fragmentation down to the individual, with algorithms pushing you this way or that. The town square, a ‘For You’ feed.

Some celebrate the collapse of The Old World. But I’m not so sure. Even if their maps were flawed, they functioned. They offered direction, connection, and a sense of contribution. And as they fade, most people haven’t fully reckoned with what we’ve lost.

What we’re left with is a world where the maps are gone, the signs are unclear, and the burden of meaning falls entirely on the individual.

II. The Now World:
Grasping for Quick Fixes

When traditional meaning structures collapse, we don’t sit calmly inside the emptiness. We don’t float serenely into enlightened freedom. We reach for something – anything! – that might hold us. Often without realizing it.

We are desperate to fill the void.

In theory, freedom offers space for transcendent discovery. But in practice, it’s terrifying to not know who you are. We’re confronted with endless possibilities, and no clear direction. Viktor Frankl called it “the existential vacuum.” Søren Kierkegaard called it the “dizziness of freedom.” A place of disorientation and vertigo, where we cling to whatever promises quick relief.

I’ve seen it firsthand. Many who chase freedom, especially the financial independence kind, fail to realize: freedom just gives you freedom. I can assure you, it doesn’t tell you what to do with it.

The Now World is not just the era we live in now. It’s also the speed at which we demand answers. We need meaning, like pronto!

Because in a world where nothing is inherently meaningful, the pressure is on you to define it. And if you don’t? The world is happy to fill the hole for you. Someone else – your employer, your political tribe, your local influencer – will do it for you. These Existential Grifters. Gurus, not gods. Promising the latest “unlock” to a spiritually starved audience.

So we inhale meaning the way we scroll content: passively and reactively. We follow without reflecting. We’re nudged into new identities. Caught in this existential drift. And when one fails to deliver the feeling we’re after? We move on to the next. Meaning, just another subscription we cancel when it stops delivering.

“In the day-to-day trenches of adult life… there is no such thing as not worshipping. Everybody worships.” – David Foster Wallace, from This is Water

Work is no longer just a place where we find purpose, structure, and community. It’s now where we sacrifice ourselves at the altar of hard work, impact, and achievement. It was my drug of choice. Workaholism is modern life’s fools gold for fulfillment, and the market is happy to abide. Even the most cynical hustlebro, in a weird way, is just looking for meaning.

"They intoxicate themselves with work so they won’t see how they really are." — Aldous Huxley

Our identity becomes a performance, an aesthetic of meaning we project for others to see, even when we don’t feel it inside. We polish our personal brands, pretend we’ve figured it out, and try to optimize/habit/goal our way into feeling whole. But it never quite lands. Even the wins feel thin on arrival, with the need for a new one now in its place. The self-help junkie keeps needing more reassurance, and the void keeps leaking through.

We are bored as fuck, but won’t give ourselves even a second to sit with the void. Distraction becomes the norm: constant entertainment, political theater, parasocial intimacy (e.g. Joe Rogan feels like your friend)… anything to avoid being alone with the uncomfortable questions.

“The mind wants to wander from the meaty big questions, which are completely daunting and unanswerable, to the diverting candy right on your phone.” — David Brooks, from The Second Mountain

What we’re experiencing is an epic-sized rebound. After breaking up with The Old World, we’re grasping for the next thing to give us structure. The void hasn’t been left empty. It’s been hastily filled with pseudo-relationships that masquerade as meaningful.

Salvation won’t come from grasping. (It hasn’t.) So what happens when we stop pretending we’ve found the answer?

III. The New World:
Exploring Without a Map

When faced with the big questions of meaning, we can retreat back to the old maps. We can reach for the quick fixes. Or… we can keep asking. We can stay in the search.

If the Old World is a cathedral,
and the Now World is a carnival,
then the New World is an open landscape.

We’re standing at the edge of something vast. Because without inherited meaning, and without easy replacements, we’re left with open space. And space, in the right light, is opportunity.

There are no official maps. No consensus truths. The terrain is a jungle of psychological, philosophical, social, and spiritual domains. Some of it may feel familiar. But most of it will ask more from you than The Now World ever did.

I’m not here to act like a guide, like I know exactly where we’re going. Sorry, this is not a how-to blueprint. It’s an open frontier for me too. But what I’m confident in is that there’s no answers in the quick fixes. We don’t need more maps. We need more people willing to wander.

I know transitional periods, having gone through one myself, and their potential for a positive reinvention. But only if done well! Transitions can leave us worse off than before, especially when we rush to get to the other side.

“Man’s search for meaning may arouse inner tension rather than inner equilibrium.” – Viktor Frankl, from Man’s Search for Meaning

Instead of stopping at the first off-ramp, with the need to define or distract, we replace trying to answer with asking. True exploration demands that you sit in the fog, and stay lost on purpose. It’s deeply unproductive, often lonely, maddeningly inconclusive. But it requires loosening your grip: on certainty, on speed, on the self you think you have to be.

If you’re an atheist (or even ambivalent), exploration may be recognizing the role religion used to play and what we’ve lost without it. If you’re religious, exploration might mean confronting the outdated holes in your faith.

If you define yourself by work, imagine who you’d be if you stopped working. If you’re anti-work, consider what might happen if the world stopped working.

If you measure life by being useful, always productive, exploring may be finding something useless and seeing where it leads. Following a curiosity with no promise of return. Letting a project be unfinished or unshared.

If ambition drives you (the need for impact, scale, applause) exploration may be shrinking your horizon, trying something so small that nobody else notices. If you’re unambitious, exploration may be attempting one bold project outside your comfort zone.

If you run on virtual connection (social media friends, podcasts filling your commutes) then exploration might mean risking the awkwardness of real connection again. Join a community (not as just a follower). Build one of your own (not just a following). Exchange self-help for other-help.

These are just examples, some I’ve tried and some I’m trying. They’re ways to tinker and experiment with new ways of looking at the world. Attempts to slow the existential drift. You can’t force your way into meaning, but you can design conditions to encourage it. All this poking around may evolve into what cognitive scientist John Vervaeke calls an “ecology of practices” – an organic system of habits, rituals, and communities that support meaning over time.

But don’t confuse exploring with escaping. It’s not about following your anxiety, but your curiosity. It’s not about fixing discomfort, but sitting with it. Not quick emotional relief, but deeper fulfillment over the long-term. It’s slow, imperfect work, and it demands more patience than The Now World ever asks for.

So you can take those psychedelics and sit in those saunas. Just be careful not to mistake the first rock you find for a home. It may just be a rock.

We are in the early days of The New World. Exploration may never be enough. The systemic problems may be too deep. Some may need a map, unable to construct meaning on their own. And we may be so far gone that we wouldn’t recognize meaning even if it smacked us in the head.

But I can offer this: it’s okay to not know. To believe something might still yet be found. It’s okay to embrace the frontier of meaning, not because you know where it leads, but because it’s the only honest move left.

I'm not here to give you a map, but a call: It’s time to explore. To embrace the open frontier, and the chance to find something real along the way.

The Old World is collapsing. The Now World is hollow. The New World is waiting.

📚 Further Exploring: For those curious enough to continue exploring…

• The Creation of Meaning (podcast), by Stephen West

• Awakening from the Meaning Crisis (video series), by John Vervaeke

• This is Water (speech), by David Foster Wallace

• The Second Mountain (book), by David Brooks

• The Purpose Code (book), by

⍰ Question: This essay is the start of a larger exploration and I invite feedback. What resonates (or not)? What questions does it raise? And what are other ways to explore?

👀 Next up: we’ll dive into the light subject that hits too close to home: The Midlife Crisis!

🙏 My Ask: the only way writing gets discovered by new readers, is when it’s shared. If you enjoy this essay, please ❤️ or 🔄 or send it to a friend.

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The Way of Work explores stories of where we fit in the world of work. This is an introduction to my 5th series, Existential Explorer - Ideas at the Edge of the Map, exploring the uncharted edges of who we become when we try to matter.

Check out my last series, Not Obvious (why work advice fails us), The Other Side of Enough (what’s life is like when you have enough).

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Nearly two years ago, I left the traditional working world at the age of 38. I found myself with time, freedom, and a gnawing sense that there was something more important to figure out than how to make more money.

The world was wide open, but I struggled to find my footing, having exited a system that once gave me structure, identity, and external metrics of success.

I thought that in the space away from work, I’d find clarity. Instead, I found more questions. Not just the “what do I do next?” variety, but also the “who am I?” ones, even some unexpected ones, like “why do I need to do anything at all?” There’s nothing quite like spending decades building a fortress of identity, only to have it crumble once you finally settle in.

Two weeks into my newfound freedom, I broke down crying to my wife. I felt alone. No one seemed to understand what I was going through. And there was guilt for questioning a life that had turned out so well. Is there anything less sympathy-inducing than the privileged guy in the midst of a midlife crisis?

One year later (a year ago), I decided to turn away from my old career to start writing. My wife will attest the day that I “went public” with this news was surprisingly emotional. Not just because I sent my first essay to a whopping 127 people (btw, thanks for everyone who has shown up since). But because it marked the beginning of an identity shift, stepping away from a place where I knew I could excel, into the unknown.

I’ve found that many people, when faced with similar questions of existential weight, go back to what they know. They handicap their own transformation by not sitting with the unsettledness, and working through it. Instead, they go back to the world they’re comfortable with. Or they swap one game for another, off the treadmill but back on a new one. They want to get themselves back on the map.

And honestly, I almost did the same, originally intending to become an Even-More-Important-Person with the next logical thing that one does in my situation. Some of you think that, armed with freedom, you’d do this or that. But just you wait… the scaffolding holding up your identity largely goes unnoticed, and when it vanishes underneath you, you’re left grasping for almost anything that can put you back on solid footing.

Meanwhile, the price of not going back induces a special kind of nausea. I had close to a million reasons to stay. Instead, I chose to start over in a new endeavor, with no promise of success. I chose to fumble around when others ask me “what do you do?” I chose to put my earned reputation in risk of ruin. No big deal!

But I chose not to go back, despite the unease. Or at least I was willing to wait out the tension a little while longer. I sensed that there was something for me, out across the open horizon, even if I couldn’t see anything there. And if I kept going, I thought I’d discover it, whatever it was.

Turns out, I did.

“Why am I here?”

At first, I thought writing was just a side project. Something to do in-between other things, while I reconciled the old me and figured out a new one. A way to keep myself occupied, rather than sliding into irrelevant oblivion.

Now, I realize that writing was the point. Or more specifically the exploration behind the writing.

One of the first lines I ever wrote still sticks with me today. It’s “the why” behind The Way of Work:

“help us find our place in the world of work.”

Whatever chaos is happening out there, we ultimately must find our place within it. While the macro changes shape the world, the micro questions carry existential weight. And the wrong lens can be the difference between a life that feels like a calling or a curse.

I know my writing is hard to label – I jump around – at least within the conventional, boring category of work or career advice. I find most of the space suffocating, ranging from feel-good (but useless) platitudes, flat either/or thinking, or “things worked out for me so they will work out for you too” blowhards.

We have deep questions about work, but the answers out there are shallow. We get productivity hacks, motivational fluff, and the same-old recycled career advice. I’m just not interested in that stuff anymore.

What I am interested in is questions of meaning and identity, with “work” as the vehicle to explore them. Because how we think about work, including its familiar themes of success, ambition, and freedom, reflects who we believe we are. Scratch the surface, and you’ll find the real stuff underneath: love, legacy, morality and mortality.

For example:

I’m less interested in what jobs AI will take,
and more interested in how we find meaning in a world without work.

I’m less interested in how to “succeed at work,”
and more interested in why success matters in the first place.

I’ve tried to write not as an expert, but as someone thinking out loud while walking the edge of the map. I have no desire to be the go-to-guy in any specialized domain. I’m too imprecise and clumsy in my approach. My skill is more in poking and provoking than in providing polished answers.

That’s why my tone changes. My format shifts. Each series is a way to test myself and the boundaries of my identity. Each essay is a way of making sense of my past, my own evolutions, and where I’m going next. These are methods of exploration, breadcrumbs left behind for anyone interested in following the spectacle.

It hasn’t always been smooth. I’ve gotten in my own way – overthinking, trying to outsmart the instincts that brought me here. I’ve chased originality, dodged cliché, and occasionally disappeared into the fog of my own expectations. I reject formulas, but secretly wonder if I should invent my own. External validation is a shallow game, but I still track my metrics religiously. It’s hard to take the businessman out of me.

I asked AI to roast my writing,1 and it came back with some uncomfortably accurate stuff:

“You’re the kind of guy who escapes the rat race… and then builds a new maze in your mind.”

Yup, sounds about right. Also:

“You loathe gurus, yet flirt with becoming one.”

C’mon, AI! Why you gotta play me like that?!?

The truth is I get stuck in my head, over-intellectualizing everything (this essay may provide some evidence). Sometimes I wonder if I’m on the verge of a breakthrough or a breakdown.

But I’ve found the payoff is so much greater when I lean into the unknown. Sure, exploring the frontiers of oneself requires risk, but the reward is discovery. Especially, when I embrace what I think I’m really doing: being an Existential Explorer.

A New Lens on Living: An ‘Existential Explorer’

I want to introduce a new concept that I’ve never heard used before: Existential Explorer. It’s a bit abstract (on purpose). And yes, it sounds a little pretentious (also on purpose 😉).

However, I think it captures what I’ve been circling this whole time. It combines two ideas:

Existentialism - explores meaning and identity, especially through the lens of the individual experience

Explorer - someone willing to head into uncharted territory, without needing to land anywhere too long

Put them together, and you get a certain type of person.

An Existential Explorer wants to understand how people make sense of their lives and their place within it. They study not just what people do, but why they do it.

They look at how we can construct a life outside of predefined structures (teaser for my next essay). They don’t just pick a popular purpose off the shelf. They check the ingredients. Try different brands. And sometimes leave the store to forage for something wilder.

An Existential Explorer starts with not trying to answer the questions, but trying to question the answers. The seeker in them is less concerned with finding “The Unifying Theory of Everything,” and more so wants to explore, and ideally live, what it is to have a good life.

They reject the illusion of rigid frameworks in favor of movement, curiosity, and contradiction. Instead of chasing certainty, they embrace ambiguity. They see the paradox in people without needing to flatten them out.

It’s a place where freedom is real, but so is uncertainty. They must contend with what it’s like to navigate without a map. The endeavor requires plenty of tangents and side quests. Some lead to strange and beautiful places. Some lead nowhere.

Identity gets slippery here too. Even following a big discovery, they are content to sail off again, never landing too long. Value is in the exploration, not the destination.

Failure is getting stuck when it’s time to move on. Or worse, wandering off into the infinite horizon, lost in perpetual confusion.

And most inconveniently, there's no money in it! Lest you believe I'm pitching some great new career opportunity… I’m not! There are many great reasons to write and explore, but don’t fool yourself that money is one of them. Yet.

I think this moment in time is ripe for existential exploration. Most of us have let our big questions get sidelined as we slog through our days. But the systems we lean on are cracking and the narratives we inherited don’t hold. A bit more poking around would probably be good for us.

Meaning is up for grabs. Institutions won’t save us. And AI will make us question our place at the top of the food chain. Living inside a world in flux, our place in it can feel so small and fragile. Some hunker down. Some numb themselves with distraction. Others try to punch a dent into the world.

Or, like me, you can move to the edges of the map. At the very least, you can watch me send myself into the void. I, for one, would rather be lost at the edge than asleep at the center.

What will be discovered out here (if anything)? We’ll see. I’ll do my best to let you know as I go.

⍰ Question: What do you think of the term ‘Existential Explorer?’ What resonates or not with you? Comment below.
🙏 My Ask: the only way writing gets discovered by new readers, is when it’s shared. Please ❤️ or 🔄 or send it to a friend.
👀 Next up: I cover The Open Frontier of Meaning (maybe my most ambitious essay yet).

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The Way of Work explores stories of where we fit in the world of work. This is part of the series, Not Obvious, exploring why work advice fails us. A few suggestions:

• Burnout, Balance, and the Bullshit in Between (on “hard work”)

• You Will Never Feel Done (on “productivity”)

• Fulfillment FOMO (on “passion”)

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I used to think success was a static conclusion you arrived at. Something that could be decided once and for all, the case closed:

“The final verdict is… you are successful!!!

(the imaginary crowd cheers)

Okay, you can go home. You’re done now.”

Sure, I’ve been pretty successful. By most objective measures, I’ve done quite well.

Financially, I’m on solid ground and even fortunate enough to examine the question of “enough.” Let me be clear: I would not be writing to you now in this non-money-making passion project without financial stability. I’ve joked that the best way to be a rich writer is to become rich, then become a writer.

Professionally, I’ve “checked all the boxes” far earlier than expected (before the age of 40), concluding I don’t need another level up the ladder. I’ve done some big/important things, too, like helping build an innovative company (in healthcare no less), that successfully IPOed and is still going strong today.

Admitting this out loud sounds like a confession, like it’s not something I’m supposed to say. But it would be dishonest to say it any other way:

“Yes, I am successful.”1

But that was the old me. I’m someone new now. And being successful is not the same as being done. Even the wildly successful must wake up and figure out what to do with their day.

I remember the moment I thought I had “made it,” but I felt… weirdly empty. Like success had arrived, but I hadn’t. Achievement is unending in this way – a loop where one triumph begets the need for another, and so on.

And every major milestone invites an inevitable appeal:

• Is my success my own, or was I lucky?

• Am I chasing the right type of success?

• Am I still successful if I can’t recreate new success?

• Who am I if I become unsuccessful?

I know I’ll never fully resolve these questions. And I wonder if maybe I’m not chasing success as much as just trying to win the argument in my head.

So what if success wasn’t a destination, but a debate? No resolution, only negotiation. A tension you live with inside yourself.

Alleged Answers

For a while, I thought I could skip the debate and go straight to the template.

I’d listen to the classic definitions of success and the templates of how to get there: the formulas, the blueprints, the 10-steps. I hoped success could be wrestled down and conquered, like hitting a bullseye on a career choice, working the perfect amount, or getting everything done.

Uncertainty bad! Certainty good! The more order put on the world → more success.

I wanted the success without the struggle. Struggle, not in terms of hard work, but as in, “I have no idea what I’m doing!” So in the absence of clarity, I turned to the ready-made answers. Each made a persuasive case. But together, they’d drown out my ability to decide what I really wanted. Loud voices in an ongoing argument I’m still trying to moderate.

“Success” seems so obvious on it’s face, that we forget it can be so malleable.

For example, success to you, could be failure to me. All the professional success in the world, without time to see my kids, is still a big net negative from my lens. That’s why certain types of broad generalized success-prescriptions make no sense. A healthy dose of cross-examination is needed.

Then there’s the inconvenient fact that we have no way of knowing what someone else’s inner life is really like, despite the arguments they make out loud. Striving for success, as we know, so often comes from a source of deep psychological pain – an unloving parent, childhood trauma, a void of meaning.

Or maybe what you’re doing looks unsuccessful today, but turns into success later on. Or what you want right now, will look different in the next decade. Or maybe… Do I need to keep going?

You will hear many definitions of success in your life (whether you want to or not). Feel free to swallow them whole without interrogation. Because, as I’ve found, they will assuage your anxiety. They will give you the comfort of certainty.

Until someday you can no longer defer the deeper questions, and the backlog builds up from a quiet hum to a rousing revolt. Take it from me: even armed with success, at some point, you will need to finally face the questions.

The Final Verdict

Others turn to me for my template: “how to be successful?” But I feel uncomfortable answering with all the questions still rolling around.

I’ve given enough advice in my life to know I don’t share all the evidence. Not that I’m lying, the bumps just get smoothed out to create a cleaner picture. Successful people post-rationalize their journey to make it sound linear, presenting the closing argument without all the evidence ahead of time. It’s a rewrite, not a reality. You can read my linear story here.

Advice givers rarely face the risks of advice takers; they have no real downside other than being ignored.

So the most unsatisfying advice you’ll ever hear would probably be the most accurate:

“This is what worked for me. I think. Based on what I can remember.

But I’m probably leaving stuff out. Maybe even lying a bit. Not to deceive you, more to deceive myself.

It’s what I think mattered. But I could be wrong. And circumstances mattered too, as well as many other factors outside my control (like luck).

And on my road to success in this one particular lane, I became unsuccessful in many others. Maybe it wasn’t all worth it.”

It’s not exactly the kind of thing that goes viral on LinkedIn. But it’s more honest.

The real skill, as I’m learning, is not finishing the perfect path, but learning to live with the paradox. Less of a judge, more of a witness.

I’ve found there is no destination called “success.” It’s not something you ever arrive at. It’s something you constantly question, redefine, and argue with yourself about. And the ones who stop debating often end up stuck in an old definition (or someone else’s idea of success).

My advice? Question it all. What your parents think. What your idols think. Definitely question that random guy online (myself included). And even question yourself. But don’t expect a verdict where you find your final answer, once and for all.

Maybe someday I’ll clean it all up. Turn the questions into a tidy, 10-part lessons learned. Or someone can do it for me (you know, at the eulogy).

Until then, I guess. I choose. I argue with myself. And the debate goes on.

Next up, will be a new series: Existential Explorer - Ideas from the Edge of the Map:

If you’ve enjoyed The Way of Work: comment, ❤️ or 🔄 below and/or share it with a friend.

The Way of Work explores stories of where we fit in the world of work. This is part of the series, Not Obvious, exploring why work advice fails us:

• Part 1: Why Work Advice Fails Us (intro)

• Part 2: Burnout, Balance, and the Bullshit in Between (on “hard work”)

• Part 3: You Will Never Feel Done (on “productivity”)

• Part 4: Welcome to Management: Please Proceed With Delusions of Control (on “management”)

• Part 5: Fulfillment FOMO (on “passion”)

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Every workplace is political. The question is: which side are you on?

On one side, are the Idealists. They think they are above politics.

They bring their whole selves to work. They focus on the work, their performance speaking for itself. Politics is what other people do.

On the other side, are the Schemers. They embrace politics and “play the game to win.”

They go full on Machiavelli, treating every interaction as a strategic move in a power game. Work isn’t about work, it’s a game of self-promotion, manipulation, and ladder-climbing. Anything goes on the way to the top.

At the start of any career, and every day after, we all have a vote: which party do we pick?

I’ve tried both sides.

I started as an Idealist. Head down, believing results would speak for themselves. And it worked, at least for a while. But as I moved up, from a junior level to SVP, the stakes changed. I found myself entangled in shifting alliances and an org chart in flux. Suddenly, great work wasn’t enough:

“I was no longer considered one of the top performers and missed a few promotions. I went through 5 different bosses in less than 2 years.” - Fluidity: How to continually reinvent yourself (in a world of change)

So I adapted and played the game. I embraced the role of a Schemer, a chameleon tuned to power dynamics. I knowingly played the relationships, shifting others in my favor. And honestly? That strategy worked too. But I lost something in the process…

“‘Other people think you are a mercenary and you will slit their throat to hit your goal.’ - feedback given to me as part of my performance review.” - From early startup to $2B public company, what 12 years at Privia Health taught

So, which side do you choose?

I. Do you stay authentic or filter yourself?

If you’re fully yourself, are you prepared for the consequences?

They didn’t mention this in that motivational seminar: other people might not like “the real you.”

I’ve seen how my “radical candor” turned into “difficult to work with.” How others didn’t appreciate my style of directness (which can be quite abrasive). They wanted silence and soft landings. So much for being myself.

Others would rather you bring your “best self” to work and not your “real self.” By being authentic, you think you are choosing integrity, but are you really choosing naïveté?

If you filter yourself, you will die a million deaths before your career is done. A silence in a meeting. A compromise you didn’t believe in. A gut instinct ignored. Every edit, denying yourself.

I too took on this mask for a few years on my way to becoming a senior executive. I was safe. Acceptable. Promotable. And unrecognizable.

Watch as your view of yourself erodes. As you step in line, your soul steps out. Your identity outsourced. A version so filtered down, you barely know who you are any more.

You think it’s a strategy, but is it more like surrender?

Which side do you choose?

II. Do you focus on the tasks or the tricks?

If you only focus on the work, how are you sure it will be seen? Will others help or block your way?

I’ve built something I deemed very valuable – only to watch it get ignored, delayed, and blocked by someone with better relationships (and worse ideas).

People who reject politics often end up frustrated, watching less competent but savvier colleagues pass by while they stay stuck. You may think you are being useful, but what if no one else agrees?

And if you are a leader, your idealism will become a liability. See as your team’s work crumbles under the weight of another exec’s ego. See as it gets killed off in a cross-functional knife fight you chose to ignore.

If you only focus on the maneuvers, when will the work actually get done? Eventually, people start asking: What do you actually do?

Being likable is nice, but it’s not the same as being respected or having influence. And when others realize you’re more style than substance, you’ll quickly lose both.

Avoid real work and you’ll soon be out of work.

Which side do you choose?

III. Do you align with power or stay independent?

If you align with power, you may rise faster. Careers are often built this way, by riding the wave of someone else (mine too). But when does loyalty turn into blind allegiance?

When you follow power, you need to accept their destination, including where it ends. I rode the power of someone for 6 years, but when they left, I had to scramble for my own survival, as I reported to 5 different bosses over the next 2 years.

Power shifts. It fades. Power might leave. Or turn on you. The same person who built you up may later hold you back, resenting your rise. Rely on one champion at your own risk.

If you stay independent, you get to chart your own course. But you may drown. You may be on your own, but that means you are on your own.

You’re free, but exposed. Principled, but alone.

When you need help, see how few volunteer to your aid. Instead of bridges, there’s walls between you. Notice, even, how others may be a little excited to see you struggle.

Which side do you choose?

IV. Do you play or get played?

If you play to win, eventually people will see right through you. It’s hard to treat every interaction as a power move without the deception seeping through your mask. One truly remarkable asshole comes to mind here…

You might win in the short term, but the reputation will catch up to you. Those who are too obvious about their maneuvering will soon find defensive rivals, intent on thwarting their moves.

Politics is like flirting, overt action spoils the game.

If you opt-out of politics entirely, it may be you who gets played. People who say, “I don’t do office politics,” are still in the game, just playing poorly.

You will certainly hit a ceiling (as I did, before I accepted the game). Beyond a certain point, it’s not about performance, it’s about perception and positioning. Who supports your work? Whose ideas get funded? Opt out of politics, and you’ve just opted out of important decisions, too.

Some companies claim they have “no politics.” What that means is: we’ve already chosen who holds power, and we don’t want you questioning it.

Which side do you choose?

V. The Paradox of Politics

Me? I’d call myself a Moderate-Idealist. I still hope the quality of my will speak for itself, and maybe even get rewarded someday by karma. But I’m willing to switch into Schemer-mode (begrudgingly) when I have to; e.g. time to get budget approved, survive until the next bonus hits the bank account.

I’m fine with Idealists, but detest Schemers – I’ve seen them infect and destroy a culture faster than it was built.1 In the end, I still hold out hope for the fantasy, but have come to accept the reality.

The problem is the two-party system can create a false choice. An either/or illusion in a world that’s far messier. Most people think there is a “right side,” but that’s the trap: there is no safe side. The enemy isn’t politics, it’s being naïve about how things work.

Conventional wisdom, it seems, gets it wrong on both ends:

“Work hard and be nice” pretends that power doesn’t exist.
“Play the game to win” assumes you can win without losing something.

Play too hard, and you lose yourself. Stay too pure, and you lose your seat. Every move shifts your standing, your story, your shot.

Others may have their side, but ultimately, you must find your own.

Bonus: Ambiguous Advice

▸ "Bring your whole self to work."
Except all those weird parts we don’t want to see.

▸ “Be a team player.”
i.e. smile, nod, and shut the hell up.

▸ “Play the game to win.”
I never let my daughter win Candy Land.

▸ “Just focus on doing great work.”
Everyone will definitely notice. Eventually. Maybe. Probably not.

Next up, I explore the concept of being “successful.” Subscribe to stay tuned.

If you’ve enjoyed The Way of Work: comment, ❤️ or 🔄 below and/or share it with a friend.

The Way of Work explores stories of where we fit in the world of work. This is part of the series, Not Obvious, exploring why work advice fails us:

• Part 1: Why Work Advice Fails Us (intro)

• Part 2: Burnout, Balance, and the Bullshit in Between (on “hard work”)

• Part 3: You Will Never Feel Done (on “productivity”)

• Part 4: Welcome to Management: Please Proceed With Delusions of Control (on “management”)

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Has any advice created as much hopeless misery as “find your passion”?

Modern workers are infected with a disease: Fulfillment FOMO.

The gnawing anxiety that you’re not quite where you’re supposed to be. That something better is out there, just beyond your grasp. You’re in the wrong job, the wrong career, maybe even the wrong life. And if you haven’t found it? You’re stuck with visions of what could be.

For a while, I bought into the hype, believing that others had it all figured out. Not anyone I knew personally, but people were out there, for sure! They told me they were living their perfect life and I bought it:

“Do what you love and the money will follow.”

But I’ve come to see this as the online version of a late-night infomercial selling miracle juice. A classic bait-and-switch: vague enough to intrigue, empty enough to disappoint.

The problem is that the alternative – suppressing your dreams – sounds way worse. So we’re supposed to endure a life of drudgery, meaninglessness, and regret? That’s what life is like?

In a choice between heaven and hell, we’re holding out hope for a heaven. So we continue on with Fulfillment FOMO, overlooking that purpose might be found in paths that don’t require a perfect fit. I explore those alternatives later.

The career fantasy that won’t set you free

I blame Ikigai.

Even if you don’t recognize the word, you already know the promise:

• Do what you love.

• Do what you’re good at.

• Do what the world needs.

• And get paid for it.

Ikigai dangles a fantasy in front of your face: a “sweet spot” where your ideal life is custom-fitted, purpose-filled, and waiting just for you.

It’s a beautifully simple formula for fulfillment… until it becomes a high-stakes hunt for the holy grail, where any wrong move results in failure.

If your work doesn’t check all the boxes, you’re settling. You’re successful, but unfulfilled. You love your work, but never make enough money. You’re doing what the world wants, but not what you want. You haven’t searched hard enough, self-reflected enough, or micro-dosed enough.

While Ikigai is theoretically possible, in reality, it’s a perfectionist’s nightmare:

“…this diagram frankly had the opposite effect, it was paralyzing. It made me miserable, and I wasted a lot of time trying to figure it out… What is my ‘one thing’ at the center of my universe that meets all these criteria? I thought about it a few different ways, but ended up giving up in frustration.” - , from Ikigai Ruined My Life

The concept of Ikigai (and others like it) sells you a fairy tale and then makes you feel like an idiot for not living up to it. For many, it doesn’t solve career anxiety, it creates it. The framework is right, just you aren’t.

The main problem, as I see it, is you can rarely jam a paycheck into a passion, let alone get the stars to align across all four categories.

“The truth is that the market doesn’t give a damn about your calling. You’re deluding yourself if you believe the system is organized around helping you find your perfect work.” - from When you don’t have a “calling”

And even if you find your thing, who says it will last forever? Most athletic careers are over soon after they begin; even Tom Brady (at 47) needs to figure out his next act. Artists have short creative peaks; there’s more one-hit-wonders than Billy Joels. Founders (who I salute but whose contentment is over-glorified) work themselves out of what they love when they sell their company (if they’re lucky), scale so big they no longer do what they love, or burnout in the process.

Callings, Ikigai, or whatever you want to call them, are actually quite fragile. Because no one tells you the small print: results may vary.

Paths to Passion

So if the apex is out of reach, now what? Do we settle for a joyless grind? Accept that work will always suck? I don’t think that’s the right answer either.

Because fulfilled people do exist! I know a few. Maybe you know some too. But in my experience, they find meaning, not nirvana. And it’s that slightly-lower-than-heaven part that’s a bit more in reach for the rest of us.

So at the risk of tearing down a flawed diagram, and then replacing it with my own flawed diagram, I’m going to share some options (not answers) I’ve noticed over time. I’ve studied people on these paths, especially looking to understand the trade-offs, not just the sugar coated sales pitch. There may be more options or more precise options-within-the-options or ways to remix them and so on. Naming this type of thing is an imprecise science (hey, just like finding your passion, which is kinda my point…).

So with full awareness that I might be doing exactly what I just critiqued, here are some imperfect, but real, paths to passion:

The Practical Path

Here, work is primarily practical and transactional. We first orient toward opportunities profit (e.g. income and savings). Passion is put on hold until later, either because it hasn’t revealed itself yet or because financial independence is required first.

“Anyone who tells you to follow your passion is already rich.” – Scott Galloway

Strengths

• Financial stability: income is predictable, bills get paid

• Clear trajectory: structured paths, makes planning easier

• Skill-building: can find fulfillment from mastery over-time

Trade-offs

• Life deferral: “I’ll do what I love later,” but later may never come

• No guarantees: that patience will be rewarded

• Habit-forming: you might never pivot (never knowing enough), career exits (voluntary or not) can become an existential crisis

Examples: stability-first careers (e.g. lawyers, doctors, accountants), FIRE (e.g. MadFientist), later career passion pursuers (e.g. Sara Pendergast, Cathy Foerster, me?)

Read next: Waiting Decades to Finally Follow Your Dreams

The Passion Bet

The leap now, figure-it-out later path. They prioritize fulfillment over finances, jumping headfirst into work they love, even if it doesn’t pay well (or at all). It’s not that money doesn’t matter, but it’s secondary to doing something meaningful.

"Follow your bliss and the universe will open doors where there were only walls." – Joseph Campbell

Strengths

• Live now: no waiting or deferral, intrinsic motivation can fuel long-term persistence

• Less regret: don’t have to wake up later wondering “what if?” (at least the passion part)

• Potential upside: if break through, the rewards can be big (financial or otherwise)

Trade-offs

• Financial instability: many struggle for years (or forever)

• No ladders: lack of defined paths to success

• Social outlier: can appear too risky or irresponsible to outsiders

Examples: creatives, artists, activists, mission-driven workers

Read next: The Pathless Path by

The Work-Life Split

The work-to-live path. Work is a means that pays the bills, funds interests, and, ideally, takes up as little time and mental space as possible. Passion isn’t monetized or careerized, it exists separately from any job.

"Not everything you love should be turned into a career. Some things are better left as hobbies." — Paul Jarvis

Strengths

• Unlimited passion options: because passions don’t need to pay

• Clarity in work’s purpose: it just has to fund life + take as little time as possible

• Like with like: no need to force passion into work (or vice versa)

Trade-offs

• Partial passions: must fit into the margins of the day

• Job is a slog: work feels like a distraction away from what you really want

• Either/or thinking: over-compartmentalize, not realizing that work can sometimes be fulfilling even if it’s not a passion

Examples: 9-5er who’s an artist on the side, weekend warriors, amateur hobbyists

Read next: The Good Enough Job by

The Passion Pivot

Like The Practical Path, but with less waiting. Instead of grinding toward financial independence, they build career capital (which creates a base), then pivot toward passion when they have enough leverage. Rather than climbing a single career ladder forever, they trade wins for freedom; shaping their work on their own terms, sometimes one move at a time. Money isn’t the goal; it’s the bridge to something better.

"Become so good they can’t ignore you. Then, use that leverage to do what excites you." — Cal Newport

Strengths

• Have it both ways: build security, but don’t wait forever

• Accelerated: to partial-freedom at midlife where you choose work you prefer

• Optionality: once you gain leverage, you have more choices

Trade-offs

• $$$ left on the table: pivot during peak earning years (a crime against capitalism!)

• Living in limbo: not maximizing either side, no single-minded clarity

• “What if?”: should you have gone all-in earlier or waited a little longer?

Examples: Successful-to-independents (e.g. , ), Portfolio Careers (e.g. ), CoastFIRE

Read next: Just Enough to Walk Away

Which trade-offs could you live with? What do you think I missed or messed up? Let me know in the comments.

Let go of the FOMO

The happiest people I know have made peace with imperfection. They shift between priorities, adjust to life’s trade-offs, and adapt instead of agonizing. They build a life that works for them, not one that fits neatly inside a Venn diagram.

I’m not going to claim any one choice is right. Every path has risks. Exactly zero are easy. But the biggest risk may be wasting your life chasing something theoretically possible, but practically out of reach.

Careers evolve (and end). Interests change. What excites you at 25 might bore you at 50. There’s rarely a "eureka moment," but always another step forward.

It turns out you can live out your passion. Just maybe not in the perfect, heavenly form you hoped for.

And if you are able to pair your passion with a paycheck… then go for it! Just think twice before you tell all of us it’s possible too.

Bonus: Ambiguous Advice

▸ “Just do what you love and the money will follow.”
- guy selling B2B accounting software.

▸ "The only way to do great work is to love what you do." – Steve Jobs
Steve, I’m so glad tech guys understand this. Because I really love my work and excited for a long, stable career at USAID.

▸ "Look for a job you love, and you will never have to work a day in your life."
Because they aren’t hiring.1

▸ “Find your calling.”
My calling is to not work, then come back and tell you all about it.

Next up, I’ll be exploring the office politics.

If you’ve enjoyed The Way of Work: comment, ❤️ or 🔄 below and/or share it with a friend.

The Way of Work explores stories of where we fit in the world of work. This is part of the series, Not Obvious, exploring why work advice fails us:

• Part 1: Why Work Advice Fails Us (intro)

• Part 2: Burnout, Balance, and the Bullshit in Between (on “hard work”)

• Part 3: You Will Never Feel Done (on “productivity”)

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Ahhh, management… the noble science of keeping everyone happy, productive, and aligned while pretending you have control over what happens next.

The workers look up, longing for a shepherd to guide them to prosperity. Or at the very least, steer away from misery. The bosses look down, longing for a proxy (paid far less), to implement their undoubtedly clear vision.

In the fantasy-land of “good management,” we are loved by all:

To our team… we’re the wise, effortless leader. Hands-off but always in tune, like the cool mom/dad on the team. We inspire, delegate flawlessly, and offer up insight when needed. And they’ll certainly never wonder if they could do our job better!

To our bosses… we are the golden child – exceeding goals, sidestepping political landmines, never passing stress back upward. In fact, did you hear? They’re reserving a spot for us up the ladder next year, a cell higher up and with a better view. And they’ll definitely never wonder if someone else could do our job better!

Guiding us through this impossible balancing act? The Management Messiahs, armed with their 1:1s, OKRs, and 10 ways to 10x our team (personally, I’m more of an 11x guy). My bookshelf groans under the weight of leadership advice, ranging from retired generals → turned-out-to-be-a-fraud CEOs → that guy who runs a lot.

And the self-help industrial complex (after successfully making us healthier and happier), double downs on dishing out wisdom, serving up platitudes from influencer-types whose most challenging direct report is a social media algorithm.

But anyone who has actually managed knows: this land is full of myths that sound great in theory but get messy in real life. That adherence to certain prescribed strategies won’t inevitably lead to success. That the notion of a 'good manager' is a well-crafted illusion, promising certainty in a role built on uncertainty.

I’ve seen too many contradictions to believe that management is a science. So, let’s talk about the myths. The ones that fill bookshelves, fuel leadership offsites, and haunt every manager who wants to get it right.

Bad Managers

Let’s get the obvious out of the way: there are a lot of “bad managers” out there. Even after we skip over the most egregious acts of immorality (e.g. harassment, fraud, general evil), it’s not too hard to spot the asshole in the office.

We all know at least one manager who makes everyone miserable. Me? One summer in college, while roofing, I had a boss who spewed so many racist and sexist slurs that the memory of him has stuck longer with me than the tar that got on my clothes.

But beyond the obvious, I’m skeptical of our definition of a “bad manager.”

One guy I worked with was disliked by many (think drill sergeant), but in chaos, he was necessary. Another time, I inherited a team that was nearly 100% not good; either deceptive under-achievers or folks who didn’t fit the future of the company. If you asked them, I’m sure I would have failed their “good manager” test. Hell, maybe I did – most were gone within the year.

Even the best business-builders of our time seem pretty horrific to work for. Scratch beyond the surface of any of your idols…

"Steve was so hard on people—relentlessly critical, often cruel. People would regularly break down in tears." – early Apple engineer

Of course, no experienced manager wants you tracking down their ex-employees to dig up dirt. It wouldn’t be that hard to find my flaws, that’s for sure. You might even get some eager volunteers.

But spotting a “bad manager” is harder than it seems. One “right” decision over here will definitely piss someone off over there. What you call an “asshole” might to me be an “asset.” Please don’t overthink that sentence.

So what about spotting the so-called “good managers”?

Good Managers

Let’s work through some of the conventional wisdom:

“Don’t micromanage.”

Okay, here’s some universal advice, right? Everyone hates micromanagers.

Except sometimes you need to micromanage. Wait, what?!?

The new employee. Or the one with performance issues. The key project or product release. The key customer. The company crisis. The critical process that cannot fail.

The defining moment of my career was when I led the launch of our business’ pivot to a new model. So you better believe I micromanaged the hell out of that project.

Sometimes you need to get up in people’s business and demand excellence. Unless, of course, that backfires and makes everything worse.

“Be a Servant Leader.”

Everyone loves a Servant Leader, especially the people getting served.

It works great…when the team is already high-functioning, clear on goals, and full of competent/collaborative people. It's management on easy-mode. Anyone can serve a team that runs itself.

But if your team needs direction or correction, what they actually need is a goddamn leader! When the company is collapsing, people are lost (or disagree), when the strategy changes overnight – you don’t want a Servant Leader attempting to create buy-in across every person and need. You need someone to dictate, not facilitate.

“Lead with transparency.”

…Right up until the moment where your team spirals into violent panic.

People say they want truth. What they really want is comfort.

Tell them all, openly, about your doubts as a leader, the fragility of your command, that their work is meaningless, their jobs are threatened by the tides of AI, that their (and your) loyalty is conditional… and watch as they crumble.

Transparency is a virtue. But so is knowing when to shut up.

“Be accountable.”

No one likes an unaccountable leader. For example, you need to “accept feedback like it’s a gift.” But if you think all feedback is useful, you’ve never been ambushed by a few detractors hijacking a meeting while everyone else tries to move forward.

Being accountable also means taking the blame when something goes wrong. You shield the team from the shit. Employees love autonomy, except when they autonomously make a huge mistake.

But be careful: take too much blame, and people might start wondering if you really are to blame! The trick is to own the failure in a noble-sort-of-way, where everyone knows you’re not really at fault. Simple, right?

“Delegate work to your team.”

Delegation is essential. But delegate too much and they’ll get overwhelmed. Worse, they’ll start wondering: “wait… what do you even do here?” Never a good question.

You should also “trust but verify.” Which means that you trust your employees, but monitor them closely in case they aren't trustworthy. And they’ll always make the right decisions because they know what you want, because you know what you want!

So encourage mistakes. Let them take risks. Just… not too many risks. Not too many mistakes! Otherwise, they need to go.

Where’s that line? Good luck finding it!

“Only hire A-players.”

The first person I ever managed was a guy named Will Wiet; still one of the best I’ve worked with (to all my former teammates reading this: you too, were one of the best!). But Will being great probably had more to do with him than me. Which raises the question: was I a good manager or did I just manage a good employee?

Not everyone will be an A-player (if you can even define that). Some of you will say: “everyone needs to be great!” Well, I don’t think you’re grounded in reality.

Sometimes A-players become A-players over time. Sometimes they aren’t “A” here, but would be an “A” over there (or without you as their manager). I worked with someone who I thought was a “B” player, but turned out to be an “A” player in another role. Or they’re an “A” this quarter, but a “B” the next (a fireable offense!). Sometimes you can’t pay enough for an A-player.

And let’s be honest: if they were that good, what are they doing working for you?

“Set clear goals. Manage what you measure.”

You need the team to work on the most important thing. Which is obvious to begin with, right? But don’t drop the other important things. Like when a client threatens to leave. Or new information upends your strategy.

We set goals. Measure progress. Implement OKRs. In our desperate search for order, we pretend human activity can be turned into pixels on a spreadsheet.

I’ve used all these before and they DO work… until they’re gamed, misinterpreted, and weaponized against common sense. Here’s how it plays out:

1. Pick a metric.

2. Incentivize it.

3. People chase the metric (because incentives).

4. Build process to keep hitting the metric.

5. Automate parts of the process.

6. …and before long, the metric becomes one with the company, embedded inside a bureaucratic nightmare that only exists to sustain itself.

KPIs don’t always measure excellence. They measure compliance. And they can be a crutch for the shallow-minded who would rather count than comprehend reality. Some of the most important things aren’t measurable: culture, customer relationships, burnout. Ignore the vibes at your own risk.

But, but, but – "you don't manage what you don't measure!" Yeah. That's the problem.

So… what makes a good manager? Depends on what you need.

Beyond Good & Bad Management

Let me be clear: I'm not saying abandon all management advice. Just that it isn’t as obvious as they make it seem. While the maxims can contain elements of truth, their blind application can create unintended consequences. They're tools, not truths.

Leadership is basically the art of making decisions while always wondering if you're doing it wrong. It invites doubt – from those you manage, those who manage you, and your own 3AM conscience. And work isn’t a predictable, rational environment where logic prevails. No one has perfect control and neither will you. Once you accept this, you stop looking for the right answer and start figuring out what works now.

When I think of the good managers I've had, the one constant is they were the right manager for me at that time, but would’ve been wrong at another time.

If "good managers" exist at all, they're those who embrace the ambiguity. Adaptable people with diverse tools for diverse problems. They don’t see choices as good vs. bad, but trade-offs with unpredictable consequences. They can live with the endless loop of contradictions, while discarding the warped expectations created by management mythology.

If you’re going to lead, then lead. But do not be fooled into believing there is some universal path to doing it “right.”

And if you somehow do it all well? Then, what are you doing here? Go forth! You’re the management guru now (just hope no one asks too many questions).

Bonus: Ambiguous Advice

▸ “Start with why.”
It’s a fancy way of saying: “because I said so.”

▸ “Lead by example.”
Wait! No, not that example!!!

▸ “Hire slow. Fire fast.”
Try no to get sued.

▸ "People don’t leave bad jobs; they leave bad managers.”
I’m also able to offer you a combo pack!

▸ “We’re like a family here.”
Dysfunctional, passive-aggressive, and full of unresolved trauma.

Next up, I explore the advice around “follow your passion:”

If you’ve enjoyed The Way of Work: comment, ❤️ or 🔄 below and/or share it with a friend.