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? What about the rest of us?
Today’s essay is a crossover from my paid Substack, Rolling in D🤦🏻♀️h. I encourage you to join us there if you haven’t already!
🧐 Do what you love and the money will follow . . . if you meet more than three of the following 20 criteria:
The economy is booming. Actually booming, not “soft landing” or “immaculate disinflation” “booming.” 😉
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 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 #4, trustafarian, or #6.
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.
📝 Permission
To pause doing what you love if the money isn’t following and you need to regroup.
✅ Do (or Delegate) This Next
What did I miss on the Top 20 list? Share in the comments and let me know :)
🔗 Resources Mentioned
Rolling in D🤦🏻♀️h: Do What You Love and the Money Will Follow . . . IF (and updated Top 20 here)
What Works: Making the Content Math Work
Khe Hy’s RadReads: **The $645,099 Business Pivot
AP: WeWork declares bankruptcy
Economic BS: “soft landing” or “immaculate disinflation”
Edison Research: Podcasting’s winner-take-all industry
Video: Steve Martin in Conversation with Charlie Rose
Podcast Production: One Stone Creative
Apps: Substack
📚 Books Mentioned
Turning the Flywheel: A Monograph to Accompany Good to Great by Jim Collins
Born Standing Up by Steve Martin
So Good They Can’t Ignore You by Cal Newport
🎧 Related Episodes
Free Time: 141: Process, Permission Slips, and Business Pivots with Tara McMullin
143: Exploring Time, Money, and Energy Capacity with Tara McMullin and Charlie Gilkey (Replay)
173: Cut Your Losses—Even While Pivoting in Public—with Khe Hy
Pivot: 326: Fool Me Once—How to Avoid Accidental and Righteous Fraud with Kelly Pope
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✍️ Check out Jenny’s personal business essays on Substack, Rolling in D🤦🏻♀️h
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