Sometime during the post-COVID housing crisis, I got the wild idea to quit my job and become a life coach. I had been kicking myself since 2014 to take a real risk. One day at work, a simple thought hit me: “What if I’m still asking ‘what if’ ten years from now?”

The answer was that I’d be in my 50s. My boss, from where I was sitting, was actively grappling with the realization that his career had peaked. He wasn’t going any higher up the corporate ladder; he was hanging onto what he had achieved by sheer force of will. From my vantage point, the personalities at the top were all cut from the same cloth: charmers with big ideas who didn’t do a damn thing. They could argue endlessly about aesthetics or why their vision was revolutionary, but they couldn’t tell you how a single mechanism actually worked.

And here’s the fuck—they were making decisions that dictated the daily lives of everyone who actually knew what to do and how to do it.

So I jumped ship.

Of course, this was after a deeply introspective exercise where a quiet, nuanced truth bubbled to the surface. The resolution was simple: No more asking what-if. In a moment of clarity, I finally understood what my subconscious had been trying to tell me. The panic attacks I was having weren’t because I felt trapped in the job; they were happening because I was terrified of leaving the question unanswered!

I was actively dodging the risk, and it was long past time to answer. The day I submitted my resignation, all of my anxiety vanished. Every single spike.

You want to know the answer I got by replacing “what-if” with action?

Proof that quitting my career to become a life coach was a terrible, awful, horrific idea.

Dear God, it was a horrendous mistake. If I could go back in time, reclaim my old desk, and sit there listening to those lobotomized squirrels with nuts for brains brainstorm terrible ideas that needed to be implemented yesterday—I’d do it in a heartbeat. Even if they sank the ship? You bet your ass. You’d find me at the bow with my closest work-wife, going down dramatically like Leonardo DiCaprio in Titanic.

I had to give up my apartment. I almost lost my car. I simply waited too long and knowingly jumped without a solid plan during the absolute worst economic climate to launch a business.

I hope you’re laughing by now, because it was a terrible, terrible idea. Taking that leap in your early 30s is a world away from walking away from a career in your early 40s. Sooner is always better than later. In my case, here are just a few of the realities I had to face because I waited:

• The digital takeover of common sense: I left right when corporations were still telling polite lies to their staff about Artificial Intelligence: “We aren’t replacing personnel! We’re just enhancing the workflow!”
• Algorithms running the gatehouse: When I was ready to return to a full-time gig to secure health coverage, I was met by a wall of AI resume screeners that jumped to absurd conclusions. It took eight grueling months to land a decent job.
• A shifting economic reality: While the market fluctuated, everyday life got expensive fast, and people tightened their belts on non-essential spending—like personal coaching.
• The coaching industry racket: I burned through a small fortune on the business side of coaching. I still coach today, and I’m damn good at it, but I have some scathing critiques of the industry that deserve their own space.

So, in the end, did I make the right decision? Yes.

Would I make the same choice again? Yes—though with a few heavy modifications.

Because most of all, I no longer have to lie awake asking “what if.” I took the risk. I paid the tuition. And the relief that comes with actually knowing the answer is something I can barely articulate.

Till next time.