I finally figured out why I can’t stop hustling. It took one phone call to get there.
I was on with my friend Todd Schuchart — future podcast co-host, unofficial therapist — and somewhere in the middle of catching up, he asked me a question I didn’t have a rehearsed answer for. Something like: what are you actually running from?
I knew immediately. I just hadn’t said it out loud before.
Our daughter was nine months old the last time I got laid off. Zero savings. No other income. My wife wasn’t working yet. It remains one of the scariest stretches of my life, and I used to stand in a ring with other men who were intent on pummeling/choking me to death — so that’s saying something.
I had no idea, in that moment, that I’d land a better job within weeks. I remember the exact spot I was standing when the offer call came in: the landing on our stairs, half-turned toward our bedroom. My wife came around the corner to listen in, and the second I gave her the nod — deal’s done — she started crying right there in the hallway.
I made a promise on those stairs. Never again.
The Reality Check:
That promise is the real reason I work as hard as I do today. Not ambition. Not passion. Insurance.
I call it career insurance — and once I named it, I understood why “just chase the passion” has never once worked as advice for me.
Career insurance isn’t a savings account. It’s not a resume. It’s the sum of every proactive habit that makes you un-layoff-able — the stuff you build before you need it, so that when your role, your company, or your entire industry becomes obsolete (hi, AI 👋), you’re not standing on a staircase finding out whether the offer comes through in time.
After that layoff, I built mine on five pillars of career insurance:
Cash runway. Not “an emergency fund” — a specific number of months you could survive at zero income, calculated, not guessed at. Today we have that and more. Back then, we had nada.
A second income stream. Something small, something real, something that doesn’t depend on your employer’s org chart. I’m decades down the road of side hustling. It’s a small business, but it’s the fuel that built the most career insurance.
Debt burned down. Every dollar of debt is a dollar of someone else’s leverage over your decisions. I went on a debt pay down streak…all funded by my side hustling.
A network you maintain, not mine. People you talk to when you don’t need anything — so it’s not strange when you do. The reason I was only unemployed for a few weeks was my network. In fact, I had a job interview before I left the parking lot.
A skill set that compounds. Not a certification. The kind of skill that makes you more valuable in a downturn, not just a boom. This one is huge. I’ve spent countless hours per week building new skills. Leveling up to stay relevant (hi, again, AI 👋).
None of these are novel. What’s novel is treating them like insurance instead of self-improvement. Insurance isn’t optional, and you don’t wait until the house is on fire to buy it.
Here’s what I didn’t expect: building career insurance didn’t make me less ambitious. My five pillars? ✅on all of them. Built up over more than a decade of being terrified I’d end up on that stairway landing again, this time without a job offer.
You would think that I’d be able to let go of my career insurance. But, I’m not. It’s engrained in who I am. The problem is—I still make decisions like I’m that same guy. Up until my call with Todd, I thought that was a bad thing. It’s not. My need for career insurance is what makes me who I am. It’s why I keep building on those five pillars even single week.
The life design version of this:
I think about this every time I’m gassed at the end of an training round and want to drop my hands or tap out. The fighters who fall apart in round three aren’t the ones with worse cardio. They’re the ones who never trained for round three — they trained to look good in round one.
Career insurance is round-three training for your income. You don’t build it in the emergency. You build it on the boring Tuesday, or in my case, I Sunday night at 9:42pm, when nothing’s wrong yet.
I still hustle. I probably always will. But I’ve stopped pretending it’s hunger.
It’s a promise I made on a staircase, to a nine-month-old who had no idea her dad was scared — and to the version of me who never wants to make his wife cry in a hallway from relief again.
Build the insurance before you need the claim.
P.S. Todd and I are in the middle of recording the opening episodes of our upcoming podcast—Sunday, Unedited. It’s an honest, transparent discussion with no script and no polish sounds interesting. Be sure you subscribe to the newsletter to get the episodes in your inbox.