Why Work Advice Fails Us
How neatly packaged advice keeps us lost and frustrated [Not Obvious: Intro]
Update: Welcome to the new folks who have joined recently (things are really taking off around here). Check out my Series Index for a good place to start.
I’m grateful to everyone who has shared my work. Now, for my new series…
The Way of Work explores stories of where we fit in the world of work. This is part of the new series, Not Obvious, exploring why work advice fails us – and what to do about it. Check out my last series, The Other Side of Enough, exploring what life is like when you have enough to never work again.
The world wants you to believe the answers are obvious.
That success follows a playbook. That if you just follow the right framework, the right guru, the right mindset — you’ll figure it all out.
The answers are out there! If you’d just for god’s sakes pick up your pathetic self and do something about it.
Like many, I’ve been warped by consuming too many neatly packaged-up lessons learned from supposedly enlightened success-types.
I’ve plugged into the drip of motivational sludge, expecting the next hit to inject me with the right insights. I still fall for the podcasts, protocols, and pieces of propaganda that are designed to make me feel like I’m missing something. That I’m behind. And I don’t quite get it yet.
I’ve routined my morning, zeroed my inbox, OKR-ed and KPI-ed my team, started with why, and all that. Sure, some ideas helped, but each created new unexpected problems that I was unprepared for. The authors conveniently never disclose the side effects, do they?
For this series, I started down that “here’s the answer” path, writing my how-to guide to work, with more bullets and less bluster. But I tidied it up too tightly, like I was hosting guests and had to hide the mess before they came over. The reality is that I’ve had too much struggle over my career, even while armed with the “right advice”, to act like I’ve got it all figured out.
My last series explored another one of these supposed “obvious answers” — financial independence — beyond the surface-level to what its really like. Similarly, I’m writing about work straight from the gut, from a place deep down that’s suffered and stressed. I’ve been in the mess too, I’m not above it.
But rather than add to the pile of sludge, with more of the same, I’m going to try to add an alternate perspective. Welcome to Not Obvious.
Join the Cult of Confidence
At the center of the problem are people who tell us to do things a certain way. As if there is a way. And if-this-then-that, cause-and-effect, we progress… in total control over our lives. It’s the seductive song:
“This is the way to be successful…”
Each bit of advice is engineered to prey on our fear, FOMO, and curiosity while promising instant transformation.
We can be drawn to this kind of success porn – and following it is a kind of masturbation. It makes us feel good (temporarily), watching other people live out their life onstage, while we look on from below in the dark, disappointing setting of our own existence.
The internet, especially, is drowning in people who have all the answers. No hesitation. No nuance. Just absolute certainty that this — whatever this is — is the answer. The perfect mix of faux wisdom and blind confidence, served daily for maximum engagement.
“It worked out for me, so it’s going to work out for you.”
They are selling the promise of certainty and we keep buying.
I’ve chased clarity from a guy with great camera lighting, but without much legitimate experience. He repackages common sense and sells it back to me as wisdom. Somehow this guy has answers?
I, myself, fit the semi-successful-guy-turned-enlightened archetype. Talk about seductive…
If there is a secret, it’s whatever they are doing to get our attention. And while we know, deep down, we’re watching the stage — a manufactured version of reality — we hope to one day act on that same stage ourselves. We not only want the advice, we want what this other person has! So that we too, may break through this crowd of pitiful peasants, to become someone who truly matters in this world – a know-it-all playing onstage for the next group of dopes in line.
I’m here to question all of this. To pull apart the pieces and see what’s really there under the bullshit.
The Bullshit and the Burden
Because the advice never really gets us anywhere, does it? The real life that most of us endure isn’t that packaged version of reality… it can be a cloud of eternal gray.
It’s dripping with ambiguity. It’s full of false starts, luck, trade-offs, and nuance. Our outside mask is one thing – it’s the performance we put on for others. But inside, we oscillate between moments of confidence and doubt.
My own career, from individual → manager → leader → whatever the heck I’m doing now, has included moments of clarity where I thought I’d cracked the code, only to be humbled soon after.
To begin with, it’s hard to know exactly where we’re going or if that direction is the right way. Sure, we aim for the best, but it’s impossible to know what’ll work. And even when we know the right direction, the muddy swamp can suck us back in. Every step demands willpower, and just when we get moving, there’s another snare to trip us up.
And it can feel like no one else is doing us any favors. The universe has its cosmic indifference, and we humans seem intent on layering more bureaucratic bullshit on top. There’s always another form to fill out!
Meanwhile, we think everyone needs to see us in a state of total control. Check your contract – it says we need to look and play the part. Nowhere does it say we need to feel the part, too. So we put on our show and others put on theirs. And we all live uncomfortably together in this way, not quite being honest with anyone, especially ourselves.
No wonder we crave answers to escape the mess!
But in our desperation, we’re drawn to easy answers – the illusion that there’s one right way.
The One Way to Rule Them All
Yes, there are good ideas out there (no doubt my newsletter has most of them 😉). The advice isn’t all wrong. It’s that it pretends to be universal. That there’s one right way and it’ll solve your specific mess.
I’m not talking about hard knowledge, like how-to build a rocket, which is abound with useful methodologies (I’m guessing, I have no idea how to build a rocket). I’m talking about the soft stuff, like how to deal with other people at work and navigate our careers, which is nearly impossible to learn without direct experience. In other words: trying things and figuring it out.
Real life can never be controlled like we hope it can. It doesn’t fit into a neat little framework. We’ll learn one “rule,” only to realize that rule needs to be broken in a slightly different circumstance.
But we must figure out our work all the same. And while we may never figure it out, we must keep on figuring.
No, there is no one way of work. And the real way of work isn’t in trying out everyone else’s supposed way. Instead, my best guess is that it is in stumbling into our own way, however confusing it may be.
Introducing: Not Obvious
The Not Obvious series is about breaking the illusion of easy answers. It’s about resisting the temptation of the obvious, to see the trade-offs and inconvenient truths.
This series is my attempt to wrestle with the advice we encounter every day:
How hard should we work?
How to be productive?
How to manage people?
How to “be successful”?
The way we talk about these things is full of contradictions wrapped in bullshit:
Work hard (but don’t burn out).
Get more done (but only the right things).
Follow your passion (unless it won’t pay).
We let clichés guide our biggest decisions and pretend these platitudes actually help. But they don’t. They just keep us running in circles, chasing certainty where none exists.
So if you’re here for another tidy little lesson, you’re in the wrong place. Go scroll LinkedIn. This is a place for the people who feel like the mainstream advice doesn’t match their reality.
This is why I’m writing Not Obvious.
The only way forward is through the mess. Are you with me?
Check out the next essay, on the never-obvious question: how hard should we work?
Special thanks to for reviewing an early draft.
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This hits hard. The way we chase advice like it’s some magic pill only to realize every "proven system" comes with fine print is painfully relatable. The whole self-help industry thrives on our insecurities, packaging common sense with just enough charisma to make it feel profound. Great article as always, Rick.
Wow, Rick. Saying the quiet parts out loud. It makes me feel less alone and certainly less inept. Thank you!