After I posted about stepping off the corporate treadmill (again) to travel, I got a flood of connection requests and several requests to chat.

Those folks, young, old and in between, wanted to say that my story resonated, and they wanted to know how I built a career that allowed me to step away, unplug, and wander the world.

The answer? It’s not a secret. It’s just not the usual and for whatever reason, my inner voice didn’t force me to follow the “you should do . . . ” that we get all the time.

Here’s what I told them (with some elaboration)

I didn’t follow a roadmap and I didn’t climb the ladder.

I took jobs that interested me. When they stopped being interesting, I left. Ok, sometimes I was shown the door. That’s it. No grand master plan, no five-year goals, no “ladder climbing” logic.

I wasn’t thinking about how each role fit neatly into a narrative that would lead to partner, VP, or any other title. Mostly because no one ever told me I should. I didn’t have good mentors early on laying out that kind of map or explaining to me how this all worked. So I made it up as I went along.

That means my career looks, and is, nonlinear. A bit jagged. Unconventional. Curious.

I said yes to things that didn’t make sense on paper.

I moved from law to business, from big pharma to tiny startups, from product liability to compliance to launching an association and a conference. I’ve not fit a convenient box more than once. I’ve taken pay cuts. I’ve walked away from good jobs. I’ve done things that made recruiters scratch their heads.

Has it always been easy? Hell no. 

Have there been tears? I can literally take you to the corner in Washington, DC where I broke down sobbing to a friend that I was never going to get a job in law again.

(Spoiler alert: I did get another job in law.)

But here’s the thing: I kept going. I kept hustling. I learned a ton. I stayed engaged. I never failed to pay my bills, even with 50% paycuts.

And I (almost) never felt stuck. I kept my expenses low, prioritized experiences over stuff, all of which might be worth more than a title or a corner office.

I’ve always known I could fall back on bartending and scuba instructing.

No, seriously. I’ve kept my fallback plan simple: I know how to make drinks and I know how to teach people to dive. And I’ve always been okay with the idea of using those skills to get by, if needed. I’m not hung up on the fact that I’m a lawyer. I don’t need a fancy title to derive self confidence or personal value (much!) I’ve worked part time and for the man and for myself. I’ve been smart with my money and investments and been very fortunate to be very overpaid at times and not to blow that money on stuff.

That’s easier, of course, when it’s just you. I’ve never married. I don’t have kids and never wanted them. That’s not better or worse, it just means the risk calculation is different. I can bounce between jobs and industries and countries without asking anyone for permission or making anyone dinner.

The world loves specialists. I’m not one.

And that’s been both a blessing and a pain. Our work culture loves tidy narratives: consistent job titles, rising responsibility, industry focus. Generalists like me don’t fit easily into that mold.

Some employers look at my résumé and see chaos. You trying explaining to people who are looking for an employee who has done this exact job, in this exact type of company, in this exact way since the start of time why and how you can do it with your eyes closed. They are looking for perfect box fillers, not someone who clearly can pick up something new and run with it. Way too much of a chance for most companies. So there have been periods of struggle with finding jobs. 

I wish more saw resourcefulness, curiosity, and adaptability, because I promise, that’s what’s actually there. 

So what’s the advice?

Decide what’s important to you early. 

Money? Titles? Career progression? 

or time and control? 

If it’s the former, I don’t have much advice for you because none of that was ever a prime motivator for me. Well, ok, money motivates me, and I chose my profession wisely as it comes with more money than most. As Mom said, you can be anything you want but make sure you choose something that will allow you to keep yourself in the style to which you are accustomed.

But if it’s the latter that motivates you? 

Take the job that excites you, even if it doesn’t make sense to anyone else. Don’t be afraid to pivot. Don’t cling to titles or compensation as your only guideposts. And if your gut says it’s time to move on, trust it.

Careers aren’t always built by climbing up. Sometimes they’re built by moving across, through, or completely off the grid.

That’s the long answer to a simple question: How did I get here?

I followed my curiosity. And when that stopped working, I moved on.

And now, I’m moving again, literally. Sabbatical II is underway. No job, no plan, just me and the road.

If nothing else, I’ll always have a backup plan involving cocktails and compressed air.