So, a few weeks ago, I told you why I keep leaving jobs that finally feel easy. The pattern. The fear. That brutal first-year tax where you question every life decision you’ve ever made.
Cool story, Chad. But how do you actually do it?
Fair question.
Because knowing you need to leave comfort isn’t the same as knowing how. And honestly? The leap is only half the problem. The other half is not face-planting on the landing.
Here’s what three major career pivots taught me about making the jump without breaking your neck.
Build Your Runway Before You Need It
Every major leap I’ve made has one thing in common: I didn’t make it broke.
When I left that cushy 22% commission gig in 2007 to start Brown Veterinary Services, I had cash reserves. Not because I was rolling in money—I wasn’t. But I’d been squirreling away funds while the checks were good.
Here’s the math that keeps people stuck: You’re making $150K. You’re spending $140K. You feel successful. You are successful. But you’re also trapped. That $10K gap isn’t freedom—it’s a leash.
You want to leap? Get six to twelve months of living expenses saved. Not invested. Not locked in your house. Boring, liquid, sitting-in-a-savings-account money. The kind that makes your financial advisor cringe because it’s “not working for you.”
It is working for you. It’s buying you options.
Start building this now. Even if you love your job. Especially if you love your job. Because when the right opportunity shows up—and it always shows up suddenly—you want to be able to say yes without your stomach dropping.
Stop Calling Yourself Your Job Title
This one drives me crazy.
“What do you do?”
“I’m a veterinarian.”
No. Stop. That’s your license. What do you actually DO?
When I was an associate vet running someone else’s clinic, I wasn’t just “a vet.” I was managing a team of people. I was making high-stakes decisions with incomplete information. I was delivering bad news to people who didn’t want to hear it. I was running a profit center. I was teaching clients complex medical concepts in language they could understand.
None of that belongs to veterinary medicine. That’s leadership. Communication. Management. Financial acumen. Those skills translate everywhere.
But if I’d kept calling myself “just a vet,” I’d have missed every opportunity outside clinical practice.
Here’s your homework: Start a running list. Word doc, Google Sheet, notes app—I don’t care. Write down every skill you use that isn’t industry-specific. Every problem you solve. Every process you improve. Every difficult conversation you navigate.
Update it monthly. Because when you’ve done something for years, you forget it’s a skill. You think everyone can do it. They can’t. That thing you find easy? Someone else finds it impossible. And that gap is your ticket out of the comfort trap.
Own Your Story Before Someone Else Does
A non-linear career path is only a liability if you let someone else narrate it.
When I interviewed at Iowa State, my resume looked like a choose-your-own-adventure book. Practice owner. Community college teacher. Vet Nursing Program director. I could almost see the committee thinking: “Does this guy know what he wants to be when he grows up?”
So I told them before they could decide for themselves.
Practice ownership? That’s where I learned what decisions feel like when your name is on the door. Teaching? That’s where I learned to meet people where they are. Program direction? That’s where I learned to scale impact from twelve students to hundreds. Each role built something the previous one couldn’t.
Same resume. Completely different story.
Start practicing your version now. Write it out. Say it out loud in the shower. Refine it until it doesn’t sound rehearsed. When someone asks, “So why did you leave that position?” you shouldn’t be scrambling. Your wandering path should look exactly like what it was: strategic capability building, not career ADHD.
Set a Damn Deadline
Comfort is a masterful procrastinator.
“I’ll make the move next year when I have more saved.” “After this project wraps up.” “When the timing is better.”
The timing is never better. Later never comes. You know this.
If you genuinely believe you’ve hit your ceiling—if comfort has become a cage—then put a date on the calendar. Not a vague intention. An actual deadline. “By June 30th, I will have either actively pursued new opportunities or committed to staying put for another two years.”
That deadline forces clarity. It forces action. It prevents the slow drift into permanent comfort that disguises itself as patience and practicality.
When I was at Mountwest in that easy teaching job, my wife and I had been casually talking about “what’s next” for months. Going nowhere. Then I gave myself a six-month window. When Purdue called within that window, I was mentally ready. Without that deadline? I probably would have talked myself out of it.
The deadline kept me honest with myself.
Brace for Impact
Nobody tells you this part: You’re going to feel stupid again.
After years of being the expert—the person with answers, the one everyone asks—you’re suddenly the one Googling where the bathroom is. You’ll make rookie mistakes you haven’t made in a decade. You’ll forget things you used to know cold because your brain is maxed out learning new systems, new politics, new unwritten rules.
This is the tax. It’s unavoidable. And it sucks.
But here’s what I had to keep reminding myself during my first year at Iowa State: That discomfort is data. It means you’re in the growth zone. If you’re not struggling, you’re not stretching. And if you’re not stretching, you’re not building anything new.
Prepare for this emotionally. Tell your spouse, your mentor, your friends: “The next twelve months are going to be rough. I need you to remind me why I did this when I forget.”
Having people who knew you before you felt incompetent—that’s what gets you through.
The Real Question
Before you go, sit with this one:
In ten years, what scares you more—the discomfort of growing or the comfort of staying exactly where you are?
For me? The guy who peaked at 45 and spent the next twenty years reminding everyone how good he used to be—that guy terrifies me more than any first-year stumble ever could.
But that’s my answer. Yours might be different. Maybe comfort is exactly right for you right now. Maybe your growth comes in depth, not breadth.
But if that ceiling is pressing down—if you feel yourself shrinking to fit a space you’ve outgrown—then you’ve got tools now. Build the runway. Document the skills. Own the narrative. Set the deadline. Brace for impact.
And when the opportunity comes? Be ready to jump.
Because the alternative is spending two decades being the professional who peaked early and spent the rest of their career talking about the good old days.
I don’t know about you, but that version of me keeps me up at night.
If you found this helpful, there’s more.
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This is Part II of a two-part series. If you missed Part I—where I explain why I keep leaving jobs that finally feel easy—you can read it here: [Why I Keep Leaving Jobs That Finally Feel Easy]