Ep 028: What I’d Tell My 20-Year-Old Self About Starting a Business

Starting a business is exciting… but it can also feel really overwhelming.

I still remember sitting at my desk in a tiny loft apartment, staring out the window, wondering:

Where do I even start?
What actually matters?
How do I make this into something real?

If you’re in that season right now—where your wheels are spinning and your ideas feel bigger than your next step—I see you. I’ve been you.

In this episode of The Kelsi Bailey Photography Podcast, I’m sharing what I would tell my 20-year-old self at the very beginning of my business.

The things I’m so glad I did… and the things I really wish I hadn’t spent so much time worrying about.

More importantly, we’re talking about what actually moves the needle when you’re building something from scratch.

Lesson #1: Learn your craft before anything else

If you are building a business around a skill, that skill matters. A lot. At the beginning of my business, I didn’t have clients. I didn’t have a full calendar. I didn’t have anything pulling me in a hundred different directions. So I picked up my camera… and I practiced. Every single day. I photographed everything. I tested light. I tried different lenses. I played with editing styles. I joined photo challenges.

At the time, I thought I was just filling my time. Now I know—that was the foundation of everything. Your website can be simple. Your logo can be basic. Your following can be small. But your work? That has to be strong.

Lesson #2: Simple is not a bad thing

At the beginning, I spent so much time trying to make everything look impressive.

The perfect website.
The perfect logo.
The perfect brand colors.

And you know what? None of that made me a better photographer. If I could go back, I would tell myself this: Simple is best.

People don’t need a flashy website to hire you. They need to understand who you are, what you do, and how to book you. That’s it. Everything else can come later.

Lesson #3: Start the email list sooner than you think

This is the one I wish I could go back and change. I didn’t start my email list until years into my business—and that is a lot of missed opportunity. An email list is personal. It’s direct. It’s yours. Social media platforms come and go. Algorithms change. Reach fluctuates.

But your email list?

That’s a relationship you get to build over time. If you’re at the beginning, don’t wait until everything looks perfect. Start collecting emails. Start showing up in their inbox. Start inviting people into your world.

Lesson #4: Your brand is more than your business

For a long time, I kept people at arm’s length. I shared my work… but not much of me.

And over time, I realized something really important: People don’t just hire a photographer.
They hire a person. When you let people see who you are—what you love, what you’re reading, what your life looks like in the in-between moments—you create connection.

And connection builds trust. You don’t have to share everything. But you do have to let people in.

A Final Reminder If You’re Just Starting

If you’re in the beginning stages of your business, take a deep breath.

You don’t need the perfect website.
You don’t need the perfect logo.
You don’t need everything figured out.

You need to practice your craft.
You need to keep things simple.
You need to start building connection.

And most importantly—

You need to keep going.

Because the girl sitting at the desk, wondering if this will ever work?

She figures it out.

And so will you.