Two roads diverged, and I chose the one that takes me forever to explain
3 years in, the obvious road I prepared for, and the weird one I chose instead [How to Be Irrelevant: Part 6]
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.
This month is the 3-year anniversary of leaving the corporate world, so it’s time for a little reflection, and another hopeless attempt at explaining what I’m actually doing with my life.
Back then, leaving was the punctuation after a crazy, but unquestionably net-positive 12-year run at a company I helped to build from zero to $2B+. At the age of 38, an Obvious Road emerged ahead: I had experience, investors, and a war chest to help me build something special in the health-tech space.
At the time, every part of me expected I’d start a company. Simply, it was the only thing I’d ever wanted to do. There were no other paths. Oh, and I had one helluva ego, which, say what you want, helps with this kinda thing.
Fast forward to today: I just wrote a dark, psychological post-apocalyptic novel.
(yeah, I keep telling people it’s fiction… it’s fiction!)
The book is weird. The choice to write it may be even weirder.
The Obvious Road
If you don’t believe my company-building conviction, and are another one of these of-course-you-did-what-you-did folks, let me prove it to you:
I have a Notion Doc where I built an entire company that doesn’t exist.
Because I’m a huge nerd, I’d devoted years-and-years of compiling notes on how to run a business. It covers topics like Starting the Company, Growth, Product, Leadership, and so on. I’ve read hundreds of business-adjacent books (not to mention all the articles and podcasts, too), then manually transcribed my underlines and notes into a master document, categorizing them by topic.
Every book. Every post. Every time.
Wacko, I know.
Nerdness Exhibit A: here’s a snapshot of the Product & Ops page where you can see I planned out, in detail, how to run usability tests (and product reviews, and product roadmaps, etc.) years before I started a business:
Each note, each little arrow, expands into a confident vote for a future I was certain I’d be living in by now. It is, without question, the most disciplined writing I’ve ever done about a thing I never ended up doing.
Buried in this document is a list of 100+ company ideas. Most are too boring to talk about in public with a general audience (Value-Based Urgent Care Enabler, anyone?). But I’m still fond of a few of them:
“Old Rush” - midlife healthcare company
“Manifest” - male-focused mental health company
“The Bunion” - The Onion, but for healthcare
I never said they were all “good” ideas, did I?
I also have, it turns out, a love for naming companies I will never start. Here’s a bunch of healthcare ones I’ll sadly never get to use:
“WellWellWell”
“Up Yours Health”
“Hole Care”
Well, maybe it’s a good thing I didn’t start that company.
Reviewing these documents always brings me a twinge of regret; a “what could have been?” feeling. These ideas are fully built, fully ready, still there, waiting. Waiting. Always. Waiting.
And man, it would’ve been easy to do one of them.
By “easy,” I don’t mean “not difficult.” I mean, starting a company is, like, kinda hard. Beyond hard, actually. What I really mean is doing “more-of-the-same.”
It’d have been the easiest decision in the world to continue doing what I’m used to doing. Then I could have kept the reputation intact, kept the identity, kept the status (with a little “Founder/CEO” boost), kept the version of me that’s easy to explain to other people, and doesn’t have to endure another “what do you do?” conversation at a kids event filled with lawyers and doctors whose eyebrows raise when I’m on paragraph two of “Well, you know, it’s a long story. I used to be a…”
If I’d gone down this path, then you, at least, wouldn’t have to suffer through my whinging online, my openbook midlife crisis, with all its twists, false starts, and dead ends.
But of course, I didn’t take that road. Instead, I took a road that made no sense at all.
The Weird Road
I discarded all those playbooks, reluctantly, all that work I’d accumulated, and chose something more akin to existential angst.
Freeing, in some ways. Totally distorting, in most others.
Overall, not a great career option.
Sure, I set up a little LLC, did some advising here and there (mostly for free). And ironically, this LLC proved to be another perfectly named business for my writing career: “Blank Page”
After feeling like the Obvious Road wasn’t it, I decided to go dark for half a year, avoiding all meetings, all outside connections, and anything looking like work. But those few months turned into a form of reawakening. Without getting all woo-woo on you, I figured out my shit. Or at least, started to be honest with myself why I wanted the things I wanted.
(if you talked to me during that period, let me just say: “I’m sorry”)
I’m not saying I didn’t have advantages. Money is the obvious one. Less obvious is the introversion. I generally prefer avoiding human encounters, or at least keeping you all at a distance, and this strange feature comes in handy when it’s time to disappear from society.
The other non-obvious advantage: I hate boxes. Always have, even when I was normal-working. I hate when anyone tries to shove me into some narrow category that may explain one fraction of me, but clearly is meant to simplify and generalize. I hate not being able to move around to try different stuff, just to fill some pre-conceived, bullshit identity someone established long ago.
The moment someone pins a label on me — “operator,” “startup guy,” “executive,” whatever — I feel the walls going up, and the need to get the hell out. It’s also why I’m not falling for my shiny new identity of “author,” because if I’m not careful, all of a sudden I need to start doing the type-of-thing-that-authors-do, like I don’t know, taking pictures of a desk with coffee on it staring out at a meadow.
No, thank you.
Guides for the Road
Of course, these types of moves are never done alone. Even I can’t avoid everyone. Instead, it’s helpful to have a few well-placed, well-timed voices of wisdom. A few that stood out, in retrospect:
“Why don’t you leave the country?” - Anne Loehr
This is probably the question that started it all.
I was going down the road of starting a company, but something didn’t feel right. So Anne gives me this unexpected zinger, that opened up a whole world of opportunity. No, I never left the country, but this question reframed my problem as one of proximity and that I just needed to get away, which I did.
(Anne also recommended I start writing, which again, was kinda solid advice)
“Why not make your sabbatical permanent?” - Khe Hy
Speaking of free consulting, Khe wins the award for: the person who most changed the trajectory of my life + I’ve never met in person.
I was in the middle of my “go dark” period, searching for answers, trying to meet people who’d gone through a similar big-life-transition. Khe’s own story is one of legend.
And I’ll never forget our first conversation where he dropped this bomb on me: why not make my whatever weird search I was on… permanent?
What do you mean? How do you make a sabbatical, by definition impermanent, permanent? That sounds like dumbest—
It was such a strange question, so out there, it took me a while to digest, and I still think about it to this day. I always thought I needed to have a thing; something that defined me that I’d settle into long-term. Certainly, something I could explain to my parents.
But wait… Did I? Why couldn’t I just keep, well, exploring?
“The people who don’t care won’t stick around.” - Kris Abdelmessih
If Anne got me writing, Kris deserves the credit for getting me to share it publicly.
(he’s got a fantastic newsletter that I’ve long recommended – I especially enjoy his one-of-a-kind rants on life)
I was worried whether sharing my inner-most existential crisis would really be a smart, strategic move. (still TBD, honestly). More importantly, I was worried about being judged by my former peers and colleagues. Even, and especially, the ones I disliked — which is its own kind of weird psychosis we don’t have time for here.
This cropped up again after I started writing fiction. The recurring nigthmare:
“Now Rick’s really gone off the deep end!”
And you know what?
They do say that! Or, most of the time, think that, then quickly walk away.
Trust me, I know. I know you know.
And guess what? That’s fine. Most people do disappear. They don’t care. They don’t reach out. They don’t respond back. They even… unsubscribe!
HOW DARE YOU?!?
But, but, but…
The people who do care stick around. People like you. You keep wondering. You’re still curious. Maybe even invested somehow in what I’m doing. You’re rooting for me. (or, of course, waiting for me to implode)
To you, I can’t say it enough: I’m grateful. Thank you.
Cause I’m doubling down. This book I wrote, it’s a weird one. By weird, I mean truly epic and awesome, filled with all the intensity and angst, plus my special dash of humor that’s edgy-yet-sophisticated, showing an undeniable cleverness that the world will finally (finally!) come to know and appreciate and love.
And I’m warning you: I’m gonna keep choosing that ol’ weird road, and it’s probably gonna get stranger with each step. And I’m gonna keep choosing to refuse to fall in love with any version that makes me stop choosing this road, again and again.
No, I can’t tell you if this all is a good idea, or it’ll all work out in the end, or you should too, because… who knows?
I’ve criticized freedom before, but this may be one of its best uses: doing stuff that’s weird and illogical and requires backflips to explain to normal people, but who cares, you want to do it anyways.
That easy, Obvious Road from before? Yeah. That’s still there, fully mapped, lights on, ready to go. It’s nice and safe and warm and people might understand you and respect you again, Rick, in the way you’ve always really wanted to be respected, and—
You know what?
Nah, I’m good.
I’m gonna stick with this weird thing I got going.
See you next time,
Rick
Open book mid-life crises is a wild phrase. I also am now curious about this Notion doc as a business nerd 👀
I felt a bit suffocated when you described the walls that close in when labels are attached - I almost on purpose stay away from labels (even though I want them and feel my ego ache) because I don't want to fool myself into thinking the labels are who I am. But this is a process
There’s a real cost to choosing the weird road, especially after you’ve built the résumé, the credibility, and the identity people know how to applaud. Walking away from the next “logical” move means losing the clean one-sentence answer to “what do you do?”
But maybe that’s the point. Some chapters aren’t supposed to make you more legible. They’re supposed to make you more honest.
The line that stuck with me is the refusal to fall in love with any version of yourself that stops you from choosing again. That feels like the real flex here: not reinvention as a new box, but reinvention as an ongoing refusal to be boxed at all.