A co-worker told me once that I'd never truly be happy until I worked for myself.
I didn't believe him at the time. But he was completely right.
My career wasn't what I thought it was going to be. I went to school for special effects design. That didn't last. I jumped to this new thing called the internet—learned multimedia and web design. Yes, I know how to make interactive CDs with Macromedia Director.
UX didn't officially exist back then. When it became mainstream in the early 2000s, it was the most logical path for me.
But I never really fit anywhere.
I've worked for marketing teams doing design. Did early web and Flash development—yes, I was Adobe Flash Certified back in the day. At Microsoft, I had an incredibly difficult tenure because I didn't fit into engineering, PM, or design. I did all of it. I wasn't able to float between them; I had to be graded against one, and it never went well at review time.
That sentiment was foreshadowing. I have never truly fit anywhere since.
Over the years I've had titles like partner implementation specialist, Flash developer, marketing designer, PHP developer, UX designer, UX engineer, manager, director—and several others mixed in. Worked for GE, GM, Microsoft, AT&T, Indeed, Anaconda, and companies no one has heard of.
I was a "unicorn." An anomaly. I could do design, write code, manage projects and people. But I never felt like "this is it, this is where I belong."
A recurring pattern: I always wanted to do more than what I was assigned.
I felt capped. Held down by my role. My mind works at the strategic level, but most employers don't want that. They want you to stay in your box and do the tasks assigned to you.
The higher I climbed, the more strategic I could operate—but it still wasn't satisfying. Still stuck in the sandbox the company wanted me in.
I solved things quickly and at high quality. We all know what that gets you: more work. No recognition, no reward. Just more assignments and the expectation that everything can be done that fast at that quality.
More work output, same pay. Perfect for them. Meanwhile I'm killing myself for nothing.
Even at the director level, I felt underutilized. Like I could do more but was capped in my UX world. Unable to truly operate cross-functionally.
That's when my co-worker made his comment. I didn't fully understand it then.
No matter what I did—what role, what company, what industry—happiness at work never lasted. The honeymoon phase of a new job wore off, and the novelty sank into the same rut I'd left previously.
I didn't intentionally jump jobs and industries, but I've been everywhere: enterprise corporations, government contractors, small startups. B2C, B2B, B2E, military, data science, HR. All different audiences and products, but UX principles stayed the same.
And at the end of every stop, the same feeling: underutilized and held down.
Don't get me wrong—I liked where I worked. I don't despise those experiences. They got me where I am and made me who I am professionally. I'm grateful. I learned difficult lessons over those decades.
It wasn't until I was forced out that everything clicked.
I got caught in the net of the big tech layoffs. Tried to find a new role, but so were 50,000 other people laid off without warning. I gave up and decided to do my own thing.
That's when I grew. That's when I made these realizations—because I could finally look from the outside in. It's hard to see your situation when you're directly in it. Much easier from the stands.
I realized I could do so much more. Execute more. Learn and expand into anything that interested me, rather than what an employer thought was best for my role.
I realize this isn't for everyone.
While unemployed, a friend and I would regularly meet up and chat about our search and life in general. He and I couldn't be more different. Doing his own thing was never going to happen for him. Not interested in the slightest.
I've met others like that—no desire to go independent, completely satisfied working for someone else. I understand. Not everyone has an entrepreneur spirit, and if they did, there'd be no one to work for them.
My life now is about balance.
I'm not chasing a salary or climbing a corporate ladder. Not pleasing someone artificially to get ahead. I teach myself what I'm interested in. I solve problems I've encountered. I build systems and work with people I enjoy.
There are real trade-offs. It's not as stable as a monthly paycheck—but is that paycheck truly stable? You're replaceable no matter what you think.
I don't adhere to a 9-to-5 schedule. I work when I want. I enjoy life with my family and make work fit into my life, not my life fit into a work schedule.
I'm not touting this as a dream that fixes everything. It has similar challenges to having a job—you just deal with them differently. For me, this works. It lets me stretch my wings and fully be me. Not who a corporate culture thinks I should be.
Even today, going back to a job is a dreadful thought.
I operate at such a high level across organizations that there's really no role except C-level that would accommodate it. Unless companies truly shift their thinking about how their workforce collaborates, I don't see the benefit.
Can you relate?
Are you feeling this in your current role? Have you taken the plunge, or are you standing on the diving board waiting for a push?
Let's talk. I'm all for networking and helping however I can. Maybe there's a future where we collaborate. Maybe we just say hi and move on. Whatever it is—the freedom I feel, I hope everyone finds.
May you find yours.