Breaking the Looking-Glass Self
On identity, reinvention, and the permission to evolve
For twenty-five years, I was Charles. Then, in 2013, I moved to Shanghai. In a city of 24 million people, no one knew who Charles was.
I started introducing myself as Charlie.
Two letters and my name became softer, easier across languages, and less formal. It was more than a new name. It was an experiment.
Charles had been an introverted wallflower from Connecticut who played computer games, wrote the beginnings of science fiction stories, loved his family dogs, cared about environmental issues, and quietly wondered if and where he’d ever fit into the world.
Charlie became the advisor for the entrepreneurship club at NYU Shanghai, started showing up to startup pitch and demo nights, and began learning to code. Bit by bit, Charlie realized that he could do things Charles never would have dreamed of.
The Looking-Glass
Something happens when you stay in one place long enough.
Your public identity stabilizes. People know you as the person who does the thing or plays the part.
In high school I was the white kid who studied Chinese and whose friends were mostly from East Asia, the shy pudgy freshman who went through puberty late, listened to emo music, and played a lot of computer games. After Shanghai, after steeping myself in the tech mecca of San Francisco, I became the Scoot guy, the Ridepanda guy. The e-bike founder. The person working on sustainable commuting.
None of those labels were wrong. They were real parts of my life. But I didn’t feel like I fully fit inside that form either. I was still changing, still morphing. And when a person with many interests keeps evolving, the narrow story people have about them can start to feel tight.
The sociologist Charles Cooley had a term for this over a century ago: the looking-glass self. We build our external sense of self by imagining and receiving how others see us. The people around us become a kind of mirror.
The mirror is useful. But it can also become a cage. You have many interests, contradictions, half-formed ideas about who you might become. But the people around you only interact with a slice, a facet. And those facets can start to feel like the whole thing when repeatedly reflected. Not just to them. To you.
People start to know you for a specific thing. The tech person. The analyst. The musician. They come to you for that, and they think of you in that way. Opportunities outside that frame don’t naturally come your way. And shifting that perception can take real effort.
This happens in jobs too.
A company is its own kind of city. People know you as the person in the role. You’re the shy engineer, the opinionated product manager, the gruff ops lead. You can grow within that frame, get promoted, take on new projects, but most organizations aren’t built to let you completely change your trajectory. You progress in your vertical. Some companies are better about this than others. Most aren’t great.
Breaking the Mirror
"In New York, you can be a new man" - Hamilton, Lin-Manuel Miranda
When you move to a new job or a new town, city or neighborhood, nobody knows your story. No one carries your past reputation: they don’t know the old versions of you, they don’t see all the old labels people attached to you over the years.
Without a narrative to overwrite, you can introduce yourself however you want. And remarkably, people tend to accept that version. Less friction than trying to break out of the mold people previously had of you.
This doesn’t mean you become someone fake. But it does mean you get to choose which parts of yourself get emphasized, which parts get to fade away, and which new parts get room to grow.
When I moved to Shanghai, I got to start choosing what to grow and what to retire almost immediately.
The point isn’t my specific story. The point is the mechanism: when the expectations around you dissolve, you get to run experiments with yourself. You discover that you’re far less fixed than you thought.
Leaving a job can be frightening. Moving to a new place can be disorienting. I don’t want to romanticize either one.
There are nights in a new city where I sit alone and think, “what the heck am I doing here?” The silence of a new apartment in a city where hardly anyone knows you is a heavy kind of quiet. You’re away from context. Away from the people who knew you well enough to call on without a reason. Away from the shorthand, the inside jokes, the places where you don’t have to explain yourself.
That loneliness can do something useful, if you let it. It forces a question you can avoid when life is so full and familiar: what am I actually after?
Not what role am I playing. Not what people expect from me. Just: what do I want?
The emptiness that comes from pulling up roots is the same emptiness that creates space. All that potential and possibility can feel incredible or terrifying depending on the day.
I’ve been nomadic the past year but have spent significant time in Mexico City, and I can feel it happening again. People in CDMX don’t meet the Scoot engineer or the Ridepanda founder. They meet someone in a café in Roma Norte on a laptop managing a dozen AI agents who never sleep.
Staying Power
I should say: staying in one place is also a critical part of identity change.
None of my reinventions would have worked without it. Shanghai wasn’t just the flight. It was the year on the ground, showing up to the pitch nights, building the relationships, learning to code, letting people treat me as entrepreneurial until I started feeling it too. San Francisco wasn’t arriving. It was eight years of community reinforcing that new version of me. Cofounders, collaborators, friends who saw the capable, social, builder Charlie and reflected that back.
The looking-glass self isn’t only a trap. It’s also how new identities take root. You need people around you who mirror the version you’re becoming, not just the one you were.
The deepest relationships in my life weren’t built in transit. They were built by showing up to the same places, with the same people, over months and years. Letting someone see you at your worst and sticking around. Having someone who knows your whole story, not just the version you introduced last month.
Staying at a job has enormous value too. I spent four years at Scoot and close to six at Ridepanda, and I wouldn’t trade that for anything. Strong relationships where I got mentored and eventually where I mentored. Understanding how different parts of a company work, what breaks, what motivates and frustrates people, how systems change as the business scales. That kind of depth only comes from staying.
Uprooting is a little different now that relationships can be more easily maintained over long distances. I left San Francisco, but I didn’t lose the people who matter. A voice note from a friend in the Mission. A video call with a cofounder. Physical distance is real. It can fray once-strong threads. But the ones that survive, maintained by both sides across distance and phases of life, often turn out to be some of the strongest ones you’ll ever have.
The Shift
But let’s be real: it isn’t necessarily about geography.
Moving or changing your job simply creates the conditions for something deeper. Identity fluidity. Human beings are not nearly as fixed as we often think. We’re shaped by the expectations around us, by the stories people tell about us, by the roles we fall into over time.
When those expectations relax, something opens up. You get to ask:
Who am I when I’m not locked into a single role?
What am I curious about now?
What would I try if no one expected me to stay the same?
You don’t need a plane ticket to ask those questions. And maybe you don’t want one.
A move is the dramatic version. It can truly give you a fresh start. If that’s what you want, it can be extraordinary. It was for me.
But there are gentler ways to create the same opening without uprooting.
Join a writing group with a bunch of strangers. Talk to people in a cafe where no one knows your job title. Try a community built around something unfamiliar. Show up to a beginner class in a discipline that has nothing to do with your career.
The Permission
This is a deliberate choice to allow yourself to evolve.
Sometimes that requires a new town or a new city. Other times, it’s just finding a new room to walk into, a writing group of strangers, a job with a different title, or a creative side project.
You aren’t erasing who you were. You’re just refusing to be stuck in the reflection of who you used to be. You’re giving yourself permission to run new experiments.
Sometimes those experiments turn out to be the most important moves of your life.