The Business of Daring

Building, Failing, and Learning: My Journey Through Entrepreneurship

If there’s one thing I’ve learned about myself, it’s that I can’t sit still when an idea sparks. I’ve started more businesses than I can count on one hand, and every single one taught me something different about ambition, patience, and the strange, exhausting joy of building something from scratch.

There was the wedding photography business, where I learned that love looks perfect in pictures but timing, lighting, and what to do when bridezillas don’t always cooperate. Then came construction remodeling, where I went from editing photos to holding power tools, learning that there’s nothing quite like turning outdated homes into something beautiful, but also, that dust gets everywhere.

At one point, I even photographed pet portraits exclusively. Yes, actual furry muses with personalities bigger than most humans I’ve met. That venture taught me that people will pay good money to immortalize their pets (and that cat owners are some of the most passionate clients on the planet).

Then came rental arbitrage, which was like learning business on hard mode. I was juggling leases, furniture, and maintenance calls at all hours because when you’re running a business, it’s not 9 to 5, it’s 24/7. Weekends? Gone. “Days off”? Funny. The hustle doesn’t clock out when you own the clock.

And most recently, there’s been thrifting and flipping, which started as a passion for unique finds and streetwear but quickly became a crash course in online marketing, customer service, and pricing psychology. It’s thrilling to see a sale go through, but it’s also real work, and the line between “hobby” and “business” blurs fast.

Some of these ventures worked. Some didn’t. Some had shining moments of success, and others fell apart in a mix of burnout, bad timing, or partnerships that just didn’t fit. I’ve worked solo and with partners, and I’ve learned both can be tough in different ways. When you’re alone, the weight of every decision falls on your shoulders. When you’re with a partner who doesn’t pull their share or whose vision just doesn’t align it becomes a tug-of-war instead of teamwork.

Here’s what I know now:

But through it all, I learned more about myself than any single venture could’ve taught me. I learned how to create LLCs, file taxes, track expenses, manage clients, market online, and most importantly, how to fail forward. I learned that failure isn’t a wall; it’s a checkpoint. Every “not quite right” business built me into someone sharper, more grounded, and more realistic about what success really takes. I learned that as a business owner, you wear all of the hats; you are the head of all the departments.

Starting a business requires more than an idea, it needs obsession. The kind of passion that keeps you awake at night brainstorming logos or figuring out how to fix something that just broke. And if that passion fades, if it starts feeling like a chore instead of a challenge, it’s okay to pivot. Passion that feels forced is just pressure with a different name.

Motivation can come from wanting freedom, control, creativity, or financial independence. But those reasons alone aren’t enough to sustain you when it gets hard. Because it will get hard. You’ll question yourself, your path, your sanity. You’ll work longer hours than any 9–5 job could ever demand and sometimes, the paycheck won’t match the effort. But the trade-off? The ownership of your choices, the freedom to say “I built that,” and the lessons that stick long after the business fades.

I’ve started and closed more businesses than I ever expected to, but every one was a dare worth taking. Because at the end of the day, it’s not about the ones that failed, it’s about the fact that I had the guts to start them at all.

So here’s to the dreamers, the builders, the ones who can’t stop creating even when it hurts. To every business that started with hope and ended with growth. To learning, to pivoting, and to daring again.

Because the real business we’re all in? The business of becoming who we’re meant to be.