🧐 Do What You Love and the Money Will Follow...IF:
You meet more than three of the following twenty criteria ✅
The phrase is emblazoned at WeWorks across the globe: in large neon lights across lobby walls, bedecking laptops via swag stickers, and printed in playful cursive on the mugs that facilitate bottomless free coffee—with the addition of always in small print at the top.
But what becomes of the adage to do what you love when the company blasting it everywhere declares bankruptcy? As the Associated Press reported two weeks ago:
NEW YORK (AP) — WeWork has filed for Chapter 11 bankruptcy protection, a stunning fall for the office-sharing company that once promised to upend the way people went to work around the world.
The filing comes at a time of incredible disruption in the commercial real estate market. The COVID-19 pandemic led to a spike in vacancies, and major markets from New York to San Francisco, are still struggling.
But it was an aggressive expansion in WeWork’s early years that led to the bulk of its current troubles. The company went public in October 2021 after an attempt two years earlier collapsed spectacularly. The debacle led to the ouster of founder and CEO Adam Neumann, whose erratic behavior and exorbitant spending spooked early investors.
If you’re noticing a pattern, yes, I admit: I can’t stand actual true crime shows—I would never sleep or leave the house—but true business crime based on Icarus-like ambition, charm, and manipulation? Putty in producers’ hands. From Billy McFarland to Elizabeth Holmes to Travis Kalanick to Adam Neumann to Sam Bankman-Fried, I do enjoy seeing business hucksters served their just desserts.
If what you love involves defrauding people, manipulating others for personal gain, or playing dirty, please do not do more of it.
But what about the rest of us?
To start by stating the obvious, mindset-wise, the viability of doing-what-you-love-and-the-money-following differs by generation. I asked ChatGPT how each cohort might react when applying this phrase to career pursuits. Generational stereotypes are just that—we are all unique ❄️—but allow me to summarize.
Generational reactions to this adage might sound something like:
Greatest and Silent: You’ve got to be EFFING kidding me. Get back to work.
Baby Boomers: Fat chance, kid. Find a good, stable job to fall in love with.
Generation X: I guess, if you have a day job while also “doing what you love”
Millennials: Look, this person on the internet did it! So can we! (Reality: 😭)
Gen Z: Do what you love as an influencer, and the #sponcon money will follow.
Gen Alpha: Does TikTok scrolling count? In all fairness, it’s too soon to tell; they were born after 2010, so the oldest are only thirteen. At that age, I had a triple-whammy of braces (plus headgear at night), glasses, and an inhaler. 🙌
Being an elder millennial myself, by 2020 I had just been sailing through ten years of a wildly booming economy during the same ten years I launched into self-employment. That means I had mostly been successful in pursuing my various passions—or at least independently groping around to find them—when the pandemic hit.1
After 80 percent of my income was wiped out within the first two weeks of March, accompanied by news headlines of people dying all around me in New York City, it was with full millennial passion scales over my eyes that I decided to double down on all the clichés: Life is short! I am going to carpe that diem! Every damn diem! I will do even more of what I love! And the money will follow! 😭😭😭🤣🤣🤣
In all seriousness, I did stop doing things that were draining my energy, and that also weren’t producing positive results. I loved speaking gigs, my steadiest income source for the previous ten years, except they had all but dried up.
So I decided to go all-in on a new direction, a book and podcast to follow where my heart had been for a long time: small business owners with Delightfully Tiny Teams. I wrote Free Time in 2021, in a state of near-hermetic bliss. I finally got out of the way of being a bottleneck in my business and “went pro” on my two podcasts by hiring a wonderful production company, the best outside team I have ever worked with.
Everything about podcasting filled me with glee—it still does. Preparing for interviews, conducting them, connecting with guests, getting feedback from listeners.
One year after launching, the show was nominated for a Webby, alongside four heavy hitters in the business category that had massive budgets and institutional money behind them. Mine was the only indie, and I was proud to represent small shows.
I can honestly say that while podcasting, I feel I am adding unique value in the world, operating at my “highest and best.”2 When I decided to go all-in, I had been podcasting for seven years; surely that was enough time to take a flyer on making it a more significant part of my business goals for the next two. Not much else was popping anyway.
For the first time—and for the last two years—I was working precisely in the strike zone of my supposed zone of genius, doing activities that truly fueled me.
Except just one problem: the money didn’t follow, at least not in a big enough way to support a household, and/or at least not yet. In contrast to 2020, I am now out of financial runway and more tired—having weathered these last three years of dumpster fires, and having tried so many things that didn’t work.
Instead of gaining unstoppable momentum via book sales and podcast downloads, my business flywheel has all-but sputtered to a stop. Hence, the need to regroup by taking a quiet sabbatical in the new year.
With all this biased context established, I now hereby offer a checklist for those of you aiming to do more of what you love. Pair this with’s post, Making the Content Math Work, and an eyeroll from anyone over 40 saying, I COULD HAVE TOLD YOU ALL OF THIS BEFORE YOU WIPED OUT YOUR SAVINGS. 🙄🙄🙄
Those who flow as life flows know they need no other force.*
* But one must do some flowing where there is an income stream.
—My Dad’s addition, written in the margins of this Ch. 8 epigraph while editing Free Time
🧐 Do what you love and the money will follow . . . IF you meet more than three of the following criteria:
You have enough money in long-term investments—index funds and the like—to live off the interest alone, keeping the principal tucked safely aside for retirement.
You are already independently wealthy. See #2, trustafarian, or #4.
You have a spouse AND said spouse earns a robust living with solid health insurance and a thick paycheck every two weeks.
You have abundant financial runway AND you don’t mind that runway crumbling beneath your wheels as you try to get the 747 of your passion off the ground.
Your passion happens to be highly lucrative and/or
“What you love” aligns with an in-demand, profitable, thriving industry—i.e. not crypto or the arts. The income streams by what you love have not been dammed, dried up, or redirected.
Even better, what you love includes working a full-time job in one of those thriving industries. You love leading teams of AI software engineers, for example.
You excel at withstanding intense, unrelenting uncertainty and financial pressure. You are also patient and stubborn.
You love your passion more than paying your bills on time.
You are clear on what you love in the first place. You’re not still in the Tinker Dabble Doodle Try phase.
You love teaching other people how to teach other people how to make money online.
You are a dynamo! In this now-global economy, you possess a one-in-a-million edge in terms of raw talent. Good looks are a plus.
You absolutely love sales and marketing! L-O-V-E. It’s a fun game, you never tire of it, and you thrive on the competitive art of climbing charts. If a leaderboard exists, you are ON IT, in both senses of the phrase.
You are well-networked by birth (fancy parents, schooling, etc.) AND/OR because you love connecting with people. You will happily meet with hordes of industry peers until your passion plane takes flight. This IG reel does not apply to you.
Caveat to #15: you must be likeable, and ideally helpful to others too. Just meeting with people won’t cut it if they can’t stand you.
You are porting over a large existing platform—email and/or any of the socials—to your new passion. AKA your personal brand plane is already well in flight, so when you punch some buttons on the dashboard to alter your course, you can now land wherever you want. See also: celebrity book clubs (those Reese boxes make great gifts, btw).
You have abundant runway and/or a large existing stream of income and/or investor funding that funnels enough paid advertising into your passion to achieve profitability escape velocity.
What you think you love is also in the highest good, and/or aligned with your soul path, what the world needs, and/or what the market wants.
🍀 You’ve hit a stroke of great luck, in perfect timing for pursuing what you love and the money following! See also: Success and Luck: Good Fortune and the Myth of Meritocracy by Robert Frank.
What am I missing??
In Conclusion . . .
Ten years ago, I read Steve Martin’s biography, Born Standing Up. I was inspired to read it by Cal Newport’s So Good They Can’t Ignore You, an entire treatise building upon one of Martin’s most famous pieces of advice. Martin recounts this idea in a 2007 interview with Charlie Rose. Here’s a one-minute clip for context:
“Nobody ever takes note of [my advice], because it’s not the answer they wanted to hear. What they want to hear is ‘Here’s how you get an agent, here’s how you write a script’ . . . but I always say, ‘Be so good they can’t ignore you.’ I just think that, if somebody’s thinking, ‘how can I be really good? people are going to come to me.’ It’s much easier doing it that way than going to cocktail parties.”
Cal’s book does a better job than I can dispelling “pursue your passion” myths. He suggests adopting a craftsperson mindset instead, while building career capital.
But still, sometimes no matter how crafty you become, you try your very best to be so good they can’t ignore you, but your best just isn’t good enough. So they do ignore you, whoever they are.3
Sometimes, despite your best efforts, you simply aren’t good enough at your chosen work-love-passion-income, or you’re not good enough in time, or you’re good-not-great while attempting to thread the needle of a winner-take-all industry that’s also experiencing a significant rise in big conglomerate competition and consolidation (ahem, like podcasting).4
So you pivot, and your right-size your goals,5 and you regroup. You connect with a new crew in the meantime (), the ones who are at least happy to hear about all your perils and pitfalls along the way, just as long as you keep getting back up.
You know in your heart something no one can ever take away from you: that at least once in your life, you lived fully, creatively, blissfully from the center of what lights you up. You recall those days so fondly it’s as if they were all a dream.6
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The term highest and best use originates from real estate. It’s a little cringe when applied to careers, but you get the idea. From Wikipedia: “[HBU] is a concept in real estate appraisal that originated with early economists such as Irving Fisher, who conceptualized the idea of maximum productivity. According to the doctrine of highest and best use, in any case where the market value of real property is sought, that value must be based on that use that would produce the highest value for a property, regardless of its actual current use.”
Speaking of appealing to the masses (or not): Read this hilarious NYT Q&A with proudly self-declared “cultural elitist” Andrew Wylie for a permission slip to focus back on the meaningful few. Don’t miss the hilarious comments section on this one too.
Although Pivot and Free Time are ranked in the top 0.5% and 2.5% of 3+ million podcasts respectively, podcasting has a massive long tail. Mine are still in the expensive, unprofitable hobby bucket; ad revenue won’t cover production costs, unless I monetize the shows via expensive products on the back-end, something that never worked very well for me either. Being in the top 0.5% means Pivot is among the top 150,000 shows.
From Edison Research — here is the distribution across the top 100 and top 1,000 shows:
“While there is plenty of listening represented all along this view, more than half of all the listening happening in the top thousand podcasts is happening in the top 100.”
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