What I’ve Learned in 3.5 Years of Being My Own Boss (That Retail Could Never Teach Me)
After over a decade managing teams in retail, I thought I had business figured out—until I took the leap into full-time self-employment. In this blog, I share the raw truth about what it’s really like to build a photography business from the ground up. Spoiler: it’s not all golden hour edits and client praise. We started with a failed t-shirt company, a poorly designed website, and no idea how SEO, marketing, or branding worked. After a long season of side hustles like DoorDash and Uber Eats, we launched our current brand, lastminutephotoshoot.com, and it’s only now—three and a half years later—that we’re seeing real traction. From hitting 40 monthly visitors to nearly 1,000, and getting consistent inquiries from our site’s contact form, every step has been a grind. I dive into how we learned discipline, balance, and self-respect—things I never learned while clocked into a corporate store. Whether you're a creative entrepreneur, new photographer, or side hustler trying to make the leap, this post will give you a brutally honest (and hopeful) view of what it really takes to build something sustainable.
Cover Image Courtesy of Jon Tyson
Let’s start with the truth:
Self-employment has been the hardest, most humbling, and most liberating experience of my life.
When I left retail management—where I ran teams of 6 to 20 people depending on the season—I thought I knew what hard work was. I’d worked weekends, holidays, late nights, back-to-back double shifts. I knew how to manage schedules, hit sales targets, coach underperformers, and keep my store afloat during Black Friday chaos.
But nothing in that job prepared me for the mental, emotional, and physical weight of running my own business.
After 3.5 years of building a business from the ground up, we’ve learned that success isn't a straight line—and you don’t have to figure it out alone. If you're navigating your own journey, we'd love to connect, swap stories, or just listen.
👉 Reach Out—We’re Here
1. The Learning Curve is Brutal (and Beautiful)
I’ve learned more in 3.5 years of working for myself than I did in all my years managing retail. You don’t just “wear many hats”—you are the business. Sales, marketing, taxes, SEO, social media, customer service, copywriting, networking, branding, accounting, production, logistics, and sometimes, janitor.
➡️ We’ve launched two websites now. Our first? It was called Hubfey. We spent a few hours a week on it (if that), didn’t touch SEO, had no social presence, and honestly expected it to just take off. Spoiler: it didn’t.
That failure forced us to learn.
Learn how to build a real website, how to create SEO-friendly pages, how Google actually works. We fumbled forward, made a ton of mistakes, Googled our way through it, and slowly found our rhythm.
When we launched lastminutephotoshoot.com, we started with zero traffic. I remember in January of this year, we hit 40 visitors for the month, and I was pumped. Now, we’re just shy of 1,000 a month—and it’s wild to think how far we’ve come. Weekly leads. Monthly bookings. We’re finally seeing momentum. It’s like watching a dream grow legs and start walking.
There’s no safety net. And strangely, that’s what makes the growth so real.
2. Discipline is the Real Boss
In retail, someone told me where to be and when. Clock in, clock out, repeat.
Now? No one’s watching. No one’s clapping. No one’s warning you when you’re coasting or burning out.
I had to build discipline from scratch—learning how to stay focused when money was low, when clients ghosted, when doubt crept in.
➡️ Everyone online says you need a perfect morning routine to succeed. Ours? It’s simple and sustainable. We wake up early, go for a walk to clear our heads, get errands and housework done in the morning, then spend the rest of the day either editing, working on the website, or creating content when we don’t have a schedule photoshoot.
When we need a break, we walk our three pups or hit the home gym. Once a week, we carve out time just for creativity—no client work, just us creating for the love of it. Or we’ll escape to the mountains for a hike and fresh air. It’s not glamorous—but it’s honest. And it works for us.
3. Side Hustles Aren’t Failures—They’re Chapters
Before Last Minute Photoshoot, we tried everything. Multiple side hustles, pivot after pivot. Some flopped. Some showed us what we didn’t want.
But each one taught us something.
➡️ Before Last Minute Photoshoot, we tried everything:
Food delivery with Uber Eats and DoorDash
A t-shirt design company (also named Hubfey)
A failed photography site under StephanieLePhotography
What we learned?
No one tells you to clock in when you’re self-employed. That food delivery grind taught us time management and hustle. We’d write “Thank you” notes with orders just to brighten someone’s day—and we saw it reflected in our tips.
Those “failures” taught us that a website isn’t a goldmine unless you nourish it—consistently. You have to learn sales, marketing, SEO, customer care. You can’t fake momentum.
4. You Don’t Just Work On Your Business, You Work On Yourself
This journey has forced me to face every insecurity I had around money, value, rejection, visibility, and worth. Running a business is personal development on steroids.
It’ll show you what you believe about yourself real quick.
Are you confident pitching yourself? Can you recover from setbacks? Do you know how to rest without guilt?
➡️ In my old life, I’d make promises to myself all the time—only to break them. Now? I can’t afford to. Being your own boss means if you don’t show up, you don’t eat. There’s no fall guy.
I’ve had to build self-trust from the ground up. These days, I check in with myself constantly:
What’s working?
Where are we stuck?
What needs improving?
What do I need to research today?
Whether it’s blog ideas, cold outreach, or figuring out a better client experience—if it moves the business forward, we do it. Even if it’s uncomfortable.
5. Success Isn’t a Moment. It’s a Series of Decisions
There’s no finish line where you “make it.” What you have instead are dozens of small decisions you make every week—some painful, some exciting—that shape the path forward.
Success started to look less like a number and more like:
Taking a day off without guilt
Feeling proud of how you handled a tough client
Seeing your work genuinely impact someone’s life
➡️ This one still blows my mind.
When we added a contact form to our site, it sat silent for months. Zero submissions. Then another month: zero.
Now? We average 1–2 form submissions every week. Not all of them book, but each one is a chance to get better at listening, understanding what clients actually want, and learning how to serve—not just sell.
I used to think success was followers or viral content. Now I know: it’s learning how to communicate better, connect more deeply, and build something real—one person at a time.
Closing Thoughts:
If you’re in the early stages of building something from scratch, know this: it’s okay to pivot. It’s okay to doubt yourself sometimes. And it’s okay to grow slower than others around you.
But don’t stop. This version of you—disciplined, creative, resilient—is being built for a reason.