I met up with an old friend from college last month, and within five minutes of sitting down, I knew something was wrong. He kept talking about his startup idea from 2018 — the one that never launched — as if he was still actively working on it. He referenced skills he hadn’t used in years like they were current. He described himself as an entrepreneur, though he’d been working a corporate job for the past three years. The disconnect was so jarring that I found myself checking my phone to confirm what year it was.
Later that night, I couldn’t stop thinking about our conversation. Not because his situation was unique, but because it was so common. How many men do I know who are stuck in this same loop, clinging to a version of themselves that expired years ago? More importantly, how often have I done the same thing?
When my second startup failed spectacularly at twenty-nine, burning through investor money in eighteen months, I spent the next year still introducing myself as a founder. Not “former founder” or “I used to run a startup” — just founder, present tense. The identity had become so central to who I thought I was that letting it go felt like admitting that entire chapter of my life had been pointless. Every networking event became a performance where I played a character I no longer was, hoping nobody would notice the costume didn’t fit anymore.
The problem wasn’t motivation. I read every productivity book, maintained elaborate morning routines, and could recite discipline mantras in my sleep. The problem was that I’d built my entire sense of self around being a successful entrepreneur, and when that stopped being true, I couldn’t figure out who I was supposed to be instead. Starting over meant acknowledging that the person I’d spent years becoming was gone, and that felt like betrayal.
This resistance to updating our identities might be more common than we think. I see it in thirty-year-olds still talking about their college achievements, forty-year-olds referencing job titles they haven’t held in a decade, and fifty-year-olds whose entire personality revolves around who they were at twenty-five.
The gym where I work out has become an unexpected laboratory for observing this phenomenon. There’s a guy who shows up every morning wearing his college football jacket from fifteen years ago. He spends more time talking about his glory days than actually working out, cornering anyone who will listen with stories about games that happened when smartphones barely existed. His identity is frozen in amber, preserved at the exact moment when he felt most powerful and certain about who he was.
I used to judge him harshly until I realized I was doing the exact same thing, just with different props. Instead of a letterman jacket, I had LinkedIn headlines. Instead of game stories, I had pitch deck presentations. The medium was different, but the message was identical: I am who I used to be, and I refuse to be anything else.
The hardest part about updating your identity isn’t the practical stuff. It’s not rewriting your resume or learning new skills or even admitting failure. The hardest part is sitting with the feeling that you wasted years becoming someone who no longer exists. Every book you read, every late night you worked, every sacrifice you made — all in service of an identity you now have to abandon. That’s not just difficult; it feels like grief.
After my startup failed, I spent months reading personal development books, thinking I was doing the work of change. In reality, I was intellectualizing my way around actually changing. I could tell you everything about growth mindset, but I was still showing up to coffee meetings pretending to be someone I wasn’t. The books became a sophisticated form of procrastination, a way to feel productive while avoiding the messier, scarier work of actually letting go.
What finally broke the spell wasn’t some grand revelation or motivational breakthrough. It was a simple question from someone I’d just met at a conference: “What do you do now?” Not what did you do, not what are you planning to do, but what do you do now, present tense, today. I stumbled through an answer about “exploring opportunities” and “leveraging past experience,” but the truth was I had no idea. For the first time, I had to confront the gap between who I was pretending to be and who I actually was.
Robyne Hanley-Dafoe, Ed.D., a psychologist, captures this perfectly: “If change has felt like something that happened to us rather than something we chose, resistance is a natural response..” It’s about invalidating the known past.
Letting go of an outdated identity doesn’t mean that time was wasted. The skills you learned, the relationships you built, the lessons you absorbed — these don’t disappear just because you stop defining yourself by them. But we get so attached to the label that we forget the substance underneath it. We become the title instead of the person who earned it.
The friend I met for coffee is still stuck in 2018, but our conversation forced me to examine my own expired identities. How many versions of myself am I still carrying around like old membership cards to clubs that no longer exist? How much energy am I spending maintaining facades that stopped serving me years ago?
Moving forward requires a kind of brutal honesty that most of us spend our entire lives avoiding. It means looking at yourself without the filters of past achievements or future potential, just seeing what’s actually there. It means having conversations where you don’t know what to say when someone asks what you do. It means starting from zero in areas where you used to be an expert, and being okay with being bad at things again.
The men who never move forward often aren’t lazy or unmotivated or lacking discipline. They’re protecting themselves from the vulnerability of becoming beginners again. They’re choosing the familiar prison of an outdated identity over the terrifying freedom of not knowing who they are yet. And honestly, I understand why. Some days, I still catch myself reaching for old business cards, both literal and metaphorical, trying to prove I’m someone I stopped being long ago.
