I want to tell you all about my friend Caroline. (Not her real name!)
I’ve known Caroline personally and professionally for over a decade. In that span, she’s been an absolute powerhouse—rising through the ranks, getting big awards, growing her expertise.
Until earlier this year. Like so many of you, she was laid off—and the job search took it out of her. When she finally signed an offer letter last week, she was elated.
But on our coaching call this week, she admitted that as excited as was, she didn’t talk much about the job to her family over Thanksgiving. Because, well… she was a little embarrassed by what they might think.
It’s not a prestigious job. You’ve definitely never heard of this org. It’s small, scrappy, and local. There are no RSUs or perks to speak of. They’ve got the technical and design maturity of an org in the early aughts.
But when talking about it to me—she didn’t sound embarrassed at all. She sounded excited. And not just because she’s getting a paycheck and health benefits again, though obviously that’s a huge relief.
There’s the lifestyle piece: Caroline’s spent years working remotely and she’s actually looking forward to being around people again. She’s newish to a small city, and has been really missing being part of a community. Yes, she has to arrive at 9am—but everyone closes their laptops precisely at 5pm, and they aren’t expected to bring any work home.
Work-wise, she gets to go elbows-deep into a thicket of systems held together by duct tape and safety pins and make it work better for her new colleagues and their customers—and they are so pumped to have her. She’s interviewing her teammates, scheduling discovery sessions, and thinking about the roadmap she’s about to own. For an org stuck in the past, she’s the perfect person to gently guide people through big changes—and make them feel safe and included in the process. Plus she gets to nerd out on a new domain that has personal meaning to her.
Does that sound like an embarrassing job? Nope.
Around the time I met Caroline, I gave a talk to a group of new designers and developers called Doing Tech Outside of Tech. It was inspired by my frustration over people’s narrow view of what “making it” looked like—working at a FAANG company, cool agency, or well-known corporation—and the unfair pressure it put on people entering the field. And, if I’m being honest with myself, I also wrote it because I had a chip on my shoulder about how undervalued I felt as someone who’d never been in those kinds of spaces.
Like Caroline, I worked at a nonprofit where our entire employee and audience experience was built on a hot mess of legacy systems, rogue Wordpress sites, and stray spreadsheets hosted on someone’s personal desktop. There was nothing glamorous about it—but I had the authority to set an end-to-end vision for our entire digital ecosystem. I was a Jill-of-all-trades: I got to own our strategy and get my hands dirty making it real. Month by month, I could see a clear, direct line between my work and its impact. I was really freaking proud of it.
And yet, eventually I left to take a fancy consulting job. Deep down, I felt like I had to prove to myself—and the world—that I could look externally successful, too.
I know right now it feels like so many of the ladders to success—to big-income, prestigious jobs—have been yanked away. I’m not celebrating that. Those jobs transformed people’s lives and gave people access to the kind of economic stability that has generational impact. I helped a lot of people transition into those jobs. And yet, all these years later, I’m still frustrated by how narrow people’s view of “making it” is.
In 2023, I left my consulting job to work for Active Voice. Even at 40, I had to field concerned questions from my family about the security and cushiness I was giving up. But where was all that concern when I nearly had a breakdown from burning out?
Who cares—I still looked great on paper.
A few months ago, I suggested that Caroline read The Good Enough Job. (You should pick it up, too!) Today, I keep thinking of this quote from philosopher Agnes Callard in it: “We seek status because we don’t know our own preferences. When we don’t trust our own definition of what is good, we let other people define it for us.”
Caroline knew her preferences: working somewhere with interesting projects to solve, with people she could collaborate with in person, where she could have time to keep up with her hobbies and life outside of work.
“I’m a big fish in a small pond, for a change,” she shared. “It’s different—but I think I’m digging it.”
She’s blocking out the noise of her family’s expectations and what reaction she might get when she updates her LinkedIn—because she knows this is what is good for her right now.
If her story resonates with you, I encourage you to spend time separating what you want from work from what you think you’re supposed to want from work. Life has its seasons—and your needs and priorities are going to change along with them.
Will everyone in your life understand—or celebrate—all of your career moves? No. But when you’re confident in your own preferences, those outside opinions don’t matter to you as much anymore. At the very least, you can catch yourself when pangs of worry or shame arise and flag them for what they are: a whole lot of conditioning that you’re slowly unlearning—that lots of us are slowly unlearning, day by day.
—Jen
Let’s write design’s next chapter.
January 29-30, 2026 • Online
Two days. Zero nonsense. Just brilliant speakers ready to get real about the chaos and contradictions of this moment in UX—and show you what happens when design steps up instead of shrinking back.
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