Start Here (when work stops working)
For the "Successful and Stuck" - essays on meaning, identity, and what comes after ambition.
I write for the person who did everything right: built the career, hit the milestones, collected the titles and the income and the respect of people whose respect you thought mattered. You may have even reached the most envious of all modern milestones: freedom!
And here comes this f-ing thing, this inner angst, that feels like a gap between the life you’ve built and the life you thought you’d feel inside it.
The problem: you’re successful and it isn’t enough.
At this point, it’s fair to wonder:
“WTF?”
“Rick has a gift for conveying deep, thought-provoking ideas.”
— Ellen Kelsay, CEO, Business Group on Health
About me
I’m Rick Foerster. I helped build a company from zero to a $2B+ public company. It was the kind of career that’s supposed to fill the void and conquer all life’s questions.
For some reason, it didn’t.
Instead, I stepped away at 38 to figure out what comes next. Two weeks into my newfound freedom, I broke down crying to my wife. I was lost.
Instead of jumping back in, I disappeared, figured out what was really going on, and eventually, found writing. The core tension I landed on: work is both the answer and the enemy. It can give us status, money, and meaning… while hollowing out our sense of self.
I started writing The Way of Work in 2024, with essays on identity, ambition, and reinvention — the real stuff underneath the career. I also wrote my debut novel (coming soon), which is either a sign of creative evolution or evidence that I’m the kind of guy who escapes the rat race… and then builds a new maze in my mind.
I try to write not as an expert, but as someone thinking out loud while walking the edges of the map. My skill is more in poking and provoking than in providing polished answers.
So if you’ve ever felt successful and still vaguely trapped… this is the right place for you.
🎧 My essays are also available on YouTube, Spotify, and Apple Podcasts.
“So well written. Sophisticated ideas in refreshingly clear prose.”
— Christopher Morris, PhD, Professor, George Mason
Who is The Way of Work for?
The Successful+Stuck. You’ve achieved most conventional measures. Career on track, bills paid (mostly), resume impresses your parents. But something underneath has shifted: you’re starting to suspect that work can’t deliver what it promised.
The Recently Unmoored. You stepped off the treadmill (by choice or by circumstance), and the freedom you expected to feel, well, didn’t show up. Instead: it’s a void, a wobble, an identity crisis you weren’t prepared for. And you’re smart enough to know a bunch of motivational platitudes won’t save you here.
The Deep Thinkers. You’re not looking for another productivity hack or a 5-step framework. You want someone that takes the hard questions seriously. You’re tired of the same shallow answers the rest of work culture keeps recycling.
But NOT for… readers who are looking for productivity hacks, “follow your passion” porn, or anything looking like tidy, cliché career advice.
“Rick walks the walk. A lot of hard fought knowledge.”
— Kristopher Abdelmessih, Founder, Moontower
Where to start?
If you’re feeling stuck in a career that looks great from the outside:
→ What You Need is a Midlife Crisis — My personal favorite. Starts with the most pathetic man alive (balding midlife man in a red convertible), but reframes the opportunity as creative destruction.
→ Why You Probably Have a Low Leverage Career — Bestselling author Nick Maggiulli included this one in his “Favorite Investment Writing of 2025”. A framework for understanding why most “good” careers are actually traps.
If you’ve already achieved enough and wonder why it doesn’t feel like enough:
→ “Fuck You Money” is Useless Without the “Fuck You” — Maybe the most popular essay I’ve written. The psychological prison most people walk into after escaping the material one.
→ Freedom is Not the Highest Form of Wealth — Another popular one. After 2 years of freedom, I have to disagree with this common belief.
If you’re asking the deeper questions (e.g. identity, meaning, what comes after ambition):
→ From Businessman to ‘Existential Explorer’ — Two weeks into my “freedom” I broke down crying to my wife. This essay is about what happened after that.
→ The Open Frontier of Meaning — My most ambitious essay. I wish more people liked it, TBD, because it’s the closest to the core of what I’m exploring here.
If you’re early in your career, but suspect you’re getting fed a lot of bullshit by others:
→ You Will Never Feel Done — Why productivity won’t save you.
→ Fulfillment FOMO — What to do when “find your passion” fails.
“[His] explorations about life remain terrifically interesting.”
— Sara Pendergast, Artist
If this sounds like it’s for you, join me. If it’s not, no hard feelings. There are plenty others that will tell you how to optimize your morning routine.
You can also check me out on YouTube, Spotify, and Apple Podcasts.
🙏 One ask: the only way writing like this finds the people who need it is when someone shares it. If you know a person who’s successful and still asking “is that it?”, then send them here.