Episode #054
5 Things I Know After 15 Years Of Pivoting
I've been changing directions in my career for nearly two decades. And while every pivot has looked different from the outside, I've started to notice some remarkably familiar moments inside them.
In this solo episode, I'm looking back at the parts of career change we tend to leave out of the before-and-after story: the strange stretch when the old thing no longer fits, the new thing isn't clear yet, and you're left trying to determine whether you're moving forward at all.
I get into the timing of knowing you're ready for a change, the surprising pull that can show up once you've decided to move in a new direction, and what our obsession with staying busy can obscure when we don't yet know what's next. I also talk about the parts of leaving an old career that have very little to do with the work itself—and a realization I've had recently about where some of our next chapters may actually begin.
Knowing You Need a Career Change Before You Know What Comes Next
I knew my dream job wasn't going to work about two months after I started it.
On paper, almost nothing could have made more sense. I had gone back to school for two graduate degrees and landed at Johns Hopkins working on international health projects funded by the Bill & Melinda Gates Foundation. The role combined communication, research, storytelling, international travel, and work that felt meaningful.
I finished my work quickly and went to my manager asking if another team needed help. She suggested I enjoy the downtime and research something interesting on the internet.
For someone who wanted to move quickly and feel useful, the day-to-day reality of the job didn't fit the picture I'd spent years working toward.
I knew that within months. I stayed for more than two years.
Leaving meant confronting much more than whether I liked my job. I had built an entire vision of my future around this career. I had three degrees, direct experience, and a promotion—and still couldn't land an interview somewhere else doing similar work.
Walking away felt like admitting I wasn't cut out for the life I'd spent years preparing to have.
Why Career Pivots Take Longer Than We Expect
One of the things I think most pivot advice gets wrong is how contained the process appears.
We see the beginning and the end: I realized I wanted something different, figured out what that was, made a plan, and moved toward it.
My experience has been far less linear.
I've found that you know something doesn't fit well before you know what does. Once you've acknowledged that something isn't working, it's difficult to unsee. But knowing what you don't want doesn't automatically produce the answer to what you want instead. That's the point where I tend to get restless.
I love forward momentum. I love getting things done. When I don't know what's next, I can convince myself that almost any movement is progress. I've taken action because something genuinely felt promising and I've taken action because I couldn't stand waiting anymore.
I've also learned how easy it is to default to what you already know during this period.
When you've built a reputation around certain work, people continue coming to you for it. The opportunities can be good. The money can be good. You may still enjoy parts of the work.
The harder question is whether you're taking it because it makes sense for this moment or because you're afraid the next thing won't work.
Why Slowing Down Matters During a Career Transition
I have said for years that you cannot change directions going 100 miles per hour. I am also exceptionally bad at following my own advice.
This summer, I decided not to push new work forward. I would finish my book, devote myself to the podcast, and let that be enough while I was home with my kids.
I hated it.
An extreme workload with competing deadlines would have been easier in some ways because productivity gives me feedback. There is something to finish, measure, or point to as evidence that I'm moving in the right direction.
Slowing down removes a lot of that.
It also creates the space that I've found almost impossible to access when every inch of my attention is occupied. There isn't much room to notice what you're drawn toward when you're constantly doing, consuming, producing, or solving.
This is different from taking a vacation. I'm talking about allowing enough space in regular life to notice what happens when every idea doesn't immediately become an action item.
For me, that's especially uncomfortable during a pivot because the absence of movement can feel like evidence that I'm stuck.
But I've jumped from one bad fit to another enough times to know that movement and forward movement aren't necessarily the same thing.
Letting Go of the Career You Thought You Would Have
It took me years to fully accept that I wasn't going back to the career I'd originally imagined.
I kept finding ways to preserve pieces of the old vision. Maybe I'd return through philanthropy. Maybe I could lead trips connected to community impact. I kept trying to make the future I'd once wanted fit the person I had become.
Part of that attachment was practical. I'd paid for the degrees. I'd invested the time. People knew me a certain way. A much bigger part was identity.
Changing direction can mean giving up a picture of yourself that you've carried for years: the work you thought you'd do, the money you expected to make, the way other people understood you, and the life you assumed would follow. I'm facing a version of that again now.
For the last seven years, much of my business has centered on brand strategy, digital presence, website copywriting, and creative direction. I love that work. I also know it isn't what I want to be doing in my next chapter.
I've had to admit that part of what has kept me frozen is that I haven't fully let that chapter expire.
Asking What You Want Now
The question I've returned to at every pivot is deceptively simple:
What do I want now?
Now matters.
I'm not asking what I want forever or demanding that the answer become my new permanent professional identity. Different seasons of my life have required different things from my work.
There have been seasons when making money mattered most. Over the past two years, I've needed creativity and enough space to write a book, build this podcast, and spend more of my attention on my own ideas after years of using my skills primarily for other people.
I'm also noticing that what I'm moving toward doesn't feel entirely new.
The part of my Johns Hopkins job I loved most was storytelling: getting close enough to understand what was happening in someone's life, making meaning from it, and helping that story matter to someone else.
Nearly two decades later, that's what I'm drawn toward again.
For a while, I've been tempted to look at the squiggly path between those two points and wonder whether I wasted time. I don't think I did. I'm returning to something I've always loved with years of experiences I couldn't have had if I'd stayed on the path I originally chose.
Maybe that's another possibility inside a career pivot worth considering: the next chapter doesn't always begin with finding something you've never done before. It might begin by noticing what has been there all along.
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