Reinventing Myself Twice: Lessons from Photography to Entrepreneurship

Mar 5

Winging It with a Camera and a Dream

When I first started as a photographer, I felt like I was figuring it out as I went along. No real plan, no defined style—just me, my camera, and a lot of winging it. I’d scroll through the sites of established fashion photographers, soaking in their perfectly curated portfolios, trying to decode their magic formula.

It was both inspiring and completely paralyzing. On one hand, I wanted to be like them—confident, polished, unmistakably professional. On the other hand, it just made me feel like I was lightyears behind. It was like staring at the finish line from a thousand miles away.

Starting out in a creative field can feel like everyone else is already miles ahead—like they’ve unlocked some secret sauce while you’re still figuring out the ingredients. My brain didn’t take it well:

They have everything figured out.
They’ve done it all already.
Where do I even fit in?

Eventually, I just decided to put myself out there. I built a quick, not-so-pretty website. I called myself a professional photographer—even though I’d been shooting for years without any formal online presence. Up to that point, I’d relied on word of mouth, which works when you’re in a place like New York. But if I wanted to grow, I had to start showing up differently.

And that’s when I learned something big: The only way to find your style is to start sharing your work, even if it feels unfinished or messy. You can’t get better at something if you don’t put yourself out there.

Reinvention Is Weirdly Familiar

A few years later, I found myself at a similar crossroads, but this time, as an entrepreneur.

Turns out, the comparison game doesn’t care if you’re a beginner or a seasoned pro. Whenever you reinvent yourself or start a new project, those old insecurities can creep back in. Now, instead of looking at photographers, I was checking out these ridiculously polished entrepreneurs. They had brands that looked like they were built in some sleek, futuristic lab—podcasts, books, courses, thriving communities. Meanwhile, I was just over here, trying to figure out where to start.

And there it was again:

How do they make it look so effortless?
How will I ever get there?
What if I’m just not cut out for this?

Honestly, it’s easy to feel like the world is divided into two camps: the polished pros and the messy work-in-progress types. But here’s the kicker: most of those polished pros? They were the messy types once too. They just kept going. They kept showing up when their website was a mess, when their ideas weren’t fully formed, when they were still figuring it out.

The Space Between You and “That Version” of You

It’s so tempting to feel like there’s this massive gap between who you are now and who you’re trying to become. It’s like everyone else has already made it across, and you’re still trying to find the bridge.

But it’s a lot closer than you think. The secret is that you don’t have to leap the whole distance at once. You just keep taking steps. The smallest move forward is still forward.

Tuning Out the Noise & Trusting Your Own Way

We live in a world that makes it really easy to think you’re behind. Social feeds are just endless highlight reels, and it’s hard not to feel like you’re lagging. But if you constantly measure your progress against other people’s finished products, you’ll never start.

Here’s what I’ve learned to do instead:

Put the blinders on when needed.
Work on your stuff first before looking at others.
Trust that your way of doing things has value—even if it doesn’t look like everyone else’s.

Your unique approach, your perspective, your way of navigating challenges—that’s what people will connect with. Not a flawless imitation of someone else.

What’s Your Next Step?

If you’re feeling stuck or overwhelmed, here are a few questions that might help:

What’s the smallest action you can take today that moves you forward?
If you didn’t care how it looked to anyone else, what would you create?
How can you lean into your own weird, messy process without worrying about the outcome?

Take a step, even if it’s small. You’ll figure it out as you go. Because that’s how all the best things happen anyway—by showing up before you’re ready.

Want more like this?

If this hit home, let me know. Drop a comment, share it with someone who needs a little nudge, or connect with me here. We’re all in this messy, creative, constantly evolving thing together.