I got the email on a Tuesday afternoon. A former colleague, someone I’d shared a cramped office with for six years, was retiring. The photos showed him on a beach, drink in hand, looking like a man who’d just won life. I sat at my desk, staring at the screen, and felt something I was not proud of.
It wasn’t happiness for him.
It was a cold, familiar claw in my chest. The same one I used to get in my twenties when I saw friends buying houses while I was still eating pasta for a week straight.
FOMO. At fifty-seven. Over retirement.
Ridiculous, right? I knew it was ridiculous. I sat there, in my home office, with work I actually enjoyed, and I felt like I was losing some race I didn’t even know I was in.
Here’s what I’ve learned since that Tuesday afternoon, after I stopped feeling sorry for myself and started thinking like a grown-up again.
First, let’s be honest about what’s really going on. It’s not the retirement. It’s the comparison.
You see their photos. The golf trips. The grandkids. The long, unstructured days that look, from the outside, like one continuous vacation. And your brain does what brains do. It builds a story. They made it. They’re free. You’re still in it. Still grinding. Still doing the thing you’ve been doing for thirty years.
But here’s the part your brain conveniently leaves out. You have no idea what their life actually feels like.
I’ve watched enough friends retire now to know the full picture. Some of them are genuinely happy. Thriving. But others? They’re restless. Bored. Lost. They spent forty years defining themselves by their job, and when the job went away, they didn’t know who the hell they were. They’d be the first to tell you, if you asked, that the first year was harder than any year they worked.
But they’re not posting that on Instagram.
The other thing nobody tells you about the retirement FOMO? It’s not about them. It’s about you. It’s a question you’re asking yourself, dressed up as envy. Am I doing this right? Am I behind? Should I be done by now?
That’s the real conversation. Not “why do they get to retire and I don’t.” It’s “what am I still doing here, and is it worth it?”
So let’s talk about that instead.
I had to sit with that question for a while. Longer than I wanted to. Because the answer wasn’t simple. I wasn’t still working because I had to be. Financially, I could have made it work. Not lavishly, but workable. I was still working because I wanted to. Because I like what I do. Because the thought of not doing it—of having no deadlines, no projects, no younger people to annoy with my opinions—felt less like freedom and more like being cut loose.
That was uncomfortable to admit. Because in our culture, retirement is framed as the goal. The finish line. If you’re not desperate to get there, something’s wrong with you.
Bullshit.
Some people thrive on structure. Some people need the intellectual engagement. Some people genuinely enjoy their work and aren’t ready to be done with it. That’s not a failure. That’s self-awareness. It’s only a problem if you’re staying out of fear—fear of what you’d do with yourself, fear of who you’d be without the title, fear of the empty hours.
If that’s you, we need to have a different conversation. Because staying in a job you hate because you’re afraid of what comes next? That’s not a career choice. That’s a hostage situation.
But if you’re staying because you still find meaning in it? Because you’re curious, engaged, maybe even having fun? That’s not FOMO territory. That’s just living your life on your own timeline.
I had to get honest with myself about that. I was feeling envy, sure. But underneath it was a different fear. Not that I was missing out on retirement. But that I was missing out on… something. The next thing. The chapter I couldn’t see yet.
Here’s what I did about it, because wallowing wasn’t helping anyone.
First, I stopped treating my career like a race. There’s no finish line. There’s no “ahead” or “behind.” There’s just your life, your choices, your weird, winding path. Comparing it to someone else’s is like comparing a hiking trail to a river. They’re both journeys. They don’t follow the same logic.
Second, I started asking myself a different question. Not “when do I get to stop?” but “what do I want more of, and what do I want less of?”
That shifted everything. Suddenly I wasn’t thinking about retirement as an escape hatch. I was thinking about my actual work. What parts still lit me up? What parts drained me? Could I do less of the draining stuff? Could I say no more often? Could I restructure my days so they looked less like a marathon and more like something I’d actually choose?
I could. I did. Nothing radical. Just some boundaries. Some conversations. A gradual shift toward work that felt meaningful and away from work that felt like obligation.
Third, I started building what I now call my “after work” life while I was still working. Not waiting. Not saving it all for some mythical retirement date. I took that trip. I started that hobby. I called that old friend I’d been meaning to reconnect with. I stopped telling myself “I’ll do that when I have time.” Because that’s the trap, isn’t it? You defer everything to a future that keeps receding. Then you look up and realize you deferred your whole life.
Fourth, I got curious about my friends’ actual retirement experiences. Not the beach photos. The real stuff. So I started asking. And what I heard was a lot more complicated than I expected.
One friend told me the first six months were great. The next six were brutal. He’d underestimated how much of his social life was tied to work. Another friend said she’d never been busier—volunteering, consulting, a part-time thing she actually loved—and that retirement was just a tax status, not an identity. Another told me, quietly, that she wished she’d waited another year. Financially, it was tighter than she’d planned. She felt trapped in a different way.
I’m not telling you this to make you feel better about still working. I’m telling you because the grass is not actually greener. It’s just different grass. With different problems.
Here’s what I finally landed on, after all that hand-wringing.
FOMO is a liar. It tells you there’s a right way to do this life, and you’re not doing it. It tells you everyone else figured it out and you’re the one who got left behind. It tells you happiness is somewhere else, in some other person’s situation, and you just need to catch up.
None of that is true.
The people retiring? Good for them. Seriously. I hope they love it. I hope they find what they’re looking for. Their path is theirs.
Your path is yours. And your path is not a consolation prize. It’s not the slow lane. It’s not the “still working” lane. It’s just your lane. The only one that matters.
So if you’re sitting there, reading this, feeling that familiar claw in your chest because another friend just announced their retirement and you’re not there yet—take a breath. Put down the phone. Stop scrolling.
Then ask yourself the real question. Not “why not me?” but “what do I actually want?”
Not what you’re supposed to want. Not what your friends have. Not what the retirement ads tell you.
What do you want?
Maybe it’s to keep working. Maybe it’s to work differently. Maybe it’s to start planning your own exit, on your own timeline, with your own version of what comes next. Maybe it’s just to stop comparing yourself to people whose full story you’ll never know.
Whatever it is, that’s your answer. Not theirs.
And for what it’s worth? That colleague from the cramped office? The one on the beach? I called him a few months later. We had a good laugh about the old days. Then he told me he was thinking about picking up some consulting work. He was bored. Missed the problems. Missed the people.
I didn’t say “I told you so.”
But I thought it. Just a little.