🐦‍🔥 "The Crumbling," Part Two

NYT–bestselling author Luvvie Ajayi Jones' on rebuilding her business after near-bankruptcy: "My inner compass was compromised. North didn’t feel like up anymore."

❤️ Jenny Blake

Mar 01, 2025

Catch up with part one first:

🐦‍🔥 Luvvie's "The Crumbling," Part One

❤️ Jenny Blake

Feb 26

“My CFO said, if we do not bring in one additional dollar—if we do not book one more piece of business—the company would be bankrupt by the end of June. This is March. Awe Luv Media would have zero in less than three months. Y’all, it was red alert time. I was officially the closest to panicking."

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“I took a deep breath—not to do, just to sit in the crumbling for a second. You know what’s interesting? A part of me felt a little bit free, because sometimes we’re afraid of the crumbling. But when it happens, you realize you just took some heavy weight off. The fear of failing that we have is often bigger than the fail itself. And I, by the criteria I had set for myself, had failed at CEOing. I spent six months in the Titanic version of a company and I had almost lost it all.”

—Luvvie Ajayi Jones, Professional Troublemaker podcast S5:E5, “Brave the Fallout”

In the valley of “The Crumbling,” after Luvvie Ajayi Jones1 fired all but one of her team members while steering through her hardest year of business, she encountered something surprising: relief.

Cascading mistakes large and small led to her Burn It All Down Moment. In an earlier post on Climbing Down the Entrepreneurial Ladder, I described a similar experience, also surrounding a book launch:

My most miserable months [of self-employment] coincided precisely with when I ran the biggest team—one that was still tiny by most outside standards.
I thought it was what I was supposed to do—have a growing coterie of consultants on retainer: an attorney, a sales agent (who sold nothing), a career EA (aka highly paid) program manager for corporate licensing and speaking clients, two entry-level admins, a community manager for my membership program, and a podcast production team.
Managing that many people made me increasingly miserable. I couldn’t hear myself think, no matter how many systems I devised or how much I delegated. So, shortly after the book launched, I let everyone go, leaving just me and the podcast production team for the summer of 2022. I was instantly happier. I had peace again, in my heart, my inboxes, and my Slack channels.

I’m so passionate about resisting the urge to grow at all costs that when I pitched the proposal for my third book to Portfolio (my previous publisher) in March 2021, it was called Delightfully Tiny Teams.

I ended up titling it Free Time after the podcast, dedicating an entire chapter to the “Goldilocks quality” of team size. If your team is too big or too small for your personality and preferences, you may feel dread, despair, depressed, drained, or distracted. For creative entrepreneurs who prioritize high net freedom, here is the horseshoe of team happiness:

Too small, and you are taxingly tiny: the burden constantly falls on you, and it’s hard to get the rest and recharging you need to do strategic work. You risk exhaustion and burnout from overwork, and from processing minutiae you dread.
If your team is too big, you may feel overwhelmed by pressure and complexity. Unless building a large company is your ambition and you love managing people, recurring meetings start to overwhelm your calendar. Time spent responding to questions adds up. Meanwhile, you’re on the hook for higher overhead; profit margins may be thinner despite—or because of—the growing team.
Delightfully Tiny Teams help you reach a personal sweet spot of efficiency and freedom as the owner, enabling you to focus on your best work.

For some of us, that means working with one or two part-time contractors, or hiring teams of specialists on an as-needed basis. Sometimes, you don’t know you’ve grown too large until you’re mired in what my friend

Charlie Gilkey

calls the “social overhead” of managing people.

Although it would soon be revealed as a blessing, at first, clearing the chaos in Luvvie’s complex operations left her reeling, shattering her trust in herself and others.

“I no longer trusted my sense of discernment, my intuition, my gut, because I felt like I had made so many mistakes in personnel choices and the trust that I gave to people,” she recounts in her “Brave the Fallout” podcast episode.

“I started taking longer to make decisions. I started asking more people for their thoughts because my compass, my inner compass, was compromised. It was off.
North didn’t feel like up anymore.”

Luvvie and I weren’t alone: according to the National Federation of Independent Businesses, confidence tanked in early 2024 as small business owner optimism fell to 88.5, its lowest levels in eleven years, and the twenty-seventh consecutive month that the index was below the 51-year average of 98.2 As of January 2025, optimism rebounded to above-average at 102.8, even as uncertainty soared to 100, the third-highest level ever recorded.

U.S. NFIB Small Business Optimism Index Strengthens in October; Uncertainty Soars - Haver Analytics

Here’s an even closer look at 2020 to 2023 as companies weathered pandemic fallout:

Chart of the Day - 9.13.23 - NFIB Small Business Optimism Index

These moments can culminate in a form of business owner ego death: whoever you thought you were, whatever you thought you were capable of, the ways of building that you thought would work begin to crumble. Your mind and your old methods are unable to gain traction in reassembling the pieces.

In his book Languishing: How to Feel Alive Again in a World That Wears Us Down, sociologist and flourishing professor Corey Keyes describes a moment when his career seemed to be peaking from the outside, but had become increasingly brittle on the inside. Even as he traveled the world giving talks while amassing “thousands of citations—the currency of intellectuals,” he felt brittle.

“As my ego expanded, my spiritual life shrank,” Keyes writes. “That change happens gradually; you don’t realize you are falling down on the dimensions of divinity until it is almost too late.”

In a foundational series of early twentieth century lectures at the intersection of psychology and religion, assembled in a book called Varieties of Religious Experience, psychologist William James calls this moment “self-surrender,” a vital turning point in religious life when one gives their conscious self over to a higher power.

For Keyes, community and spiritual practices (among other flourishing ingredients he shares throughout the book) helped him slow down again, enabling him to reconnect to himself and to the divine. He writes,

“When we honor the best inside us, we honor our higher power, whether that higher power be God, nature, or anything else that is inherently good, bigger and stronger than you are when you are at your weakest.”

If you are one of the strange types like me who are called run their business (and life) through faith and surrender, this is when you must get quiet enough to hear the next call. You must clear the way—or it will be cleared for you.

I can only speak for myself, reinvigorated by Keyes’ and Luvvie’s stories, that in these moments, faith becomes utterly essential. It’s all that’s left.

❤️

Continue reading part three on the aha moment that pulled Luvvie out of despair: “You can't have two drivers to a car.”3