“Rick has a gift for conveying deep, thought-provoking ideas.”
- Ellen Kelsay, CEO, Business Group on Health
So I want to be honest with you from the beginning:
I’m a recovering startup addict and self-proclaimed “Pretty Big Deal” (well, I used to be…). Now? I’ve become an aspiring nobody writer.
After helping build and grow a company from zero to $2B+, I thought I had the kind of career that’s supposed to fill the void and conquer all life’s questions. For some reason, it didn’t.
So I walked away from that safe and warm and respected life to basically become professionally unemployed, and eventually, find writing. Today, I now have what I can only describe as a “diversified portfolio of identities:” part writer, part advisor, part dad, and part ain’t-never-gonna-to-be-boxed-in-by-another-identity.
I write essays about meaning, identity, and reinvention (with my special dash of charming humor). My debut novel — An End to Remember, a post-apocalyptic survival story with a psychological bite — will be coming out soon.
So join me and let’s find a way to knock out all the big questions, while having fun and, most importantly, remaining the center of attention.
It’s the simple things in life, right?
Cheers,
Rick
“So well written. Sophisticated ideas in refreshingly clear prose.”
- Christopher Morris, PhD, Assistant 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.
“[His] explorations about life remain terrifically interesting.”
— Sara Pendergast, Artist
Where to start?
You can start with the series collection, or…
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 about work:
→ 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.
🎧 My essays are also available on YouTube, Spotify, and Apple Podcasts.
“Rick walks the walk. A lot of hard fought knowledge.”
- Kristopher Abdelmessih, Founder, Moontower
