The Bankruptcy and Pursuit of Dreams

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:

1. The economy is booming. Actually booming, not “soft landing” or “immaculate disinflation” “booming.” 😉
2. You are clear on what you love in the first place. You’re not still in the Tinker Dabble Doodle Try phase.
3. You love teaching other people how to teach other people how to make money online.
4. 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.
5. You are already independently wealthy. See #4, trustafarian, or #6.
6. You have a spouse AND said spouse earns a robust living with solid health insurance and a thick paycheck every two weeks.
7. 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.

Continue reading »

📝 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
• Reese’s Book Club
• 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
• Free Time: Lose the Busywork, Love Your Business
• Pivot: The Only Move That Matters Is Your Next One
• Life After College

🎧 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
• 183: Letting Go of Productivity Guilt with Madeleine Dore
• Pivot: 326: Fool Me Once—How to Avoid Accidental and Righteous Fraud with Kelly Pope; 29: Deep Work: Ditch Cognitive Junk Food with Cal Newport; 122: Digital Minimalism with Cal Newport

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✍️ Check out Jenny’s personal business essays on Substack, Rolling in D🤦🏻‍♀️h

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