10 Solid Reasons Why You Shouldn’t Start Your Own Business (Unless You’re Ready to Cry in the Shower Sometimes)
Starting a business sounds romantic—until you realize you're up at 4:45AM charging batteries, juggling invoices, and wondering if anyone even saw that post you spent hours on. Inspired by Chris Williamson’s podcast and our own messy journey, this blog shares 10 brutally honest reasons why you shouldn’t start your own business—unless you're okay with self-doubt, debt, wearing 12 hats at once, and crying in the shower. From racking up credit cards to working sick and missing out on weekends, Stephanie and I lived it all. But writing this is a reminder to ourselves and maybe to someone out there too: if you show up daily, it does get better. This isn’t just a rant—it’s real-life perspective from two full-time photographers who are still grinding, still learning, and still not giving up.
A black and white photo of us, reflected on the surface of a car — simple, stripped of distraction, and exactly how life feels when you stop making excuses. This image reminds me that life, like this photo, is often black and white. You either show up for yourself every day or you don’t. And if you don’t, that’s fine — just don’t complain when things don’t go your way. After leaving our 9–5 jobs, I learned that truth the hard way. Now, every single day I ask myself: Is this moving me toward my goal, or not? Reflect as often as you can.
I was listening to Chris Williamson on Modern Wisdom the other day when he mentioned a blog titled something like “Reasons You Shouldn’t Start a Business” — and it hit me. Hard. Because I’ve lived it.
When Stephanie and I got furloughed during COVID, we took a leap of faith and decided to go all-in on photography — our side hustle turned last-ditch plan. At first, things looked good. We had a cushion. Over 100 hours of PTO paid out. I cashed out my 401k after seven years with the same company. We thought we were set… until we weren’t.
Suddenly, we were charging groceries, gas, gear, and coffee onto our credit cards. The debt piled up faster than bookings. We doubted ourselves so many times. There were nights we cried, wondering if we made a mistake. And mornings where we faked confidence, packed our gear, and drove out anyway — sometimes to last-minute shoots, sometimes to clients who ghosted us.
That blog reminded me of something else I heard from Gary Vee: everything you create in the beginning is going to suck. Your posts, your offers, your edits — it’s all trial and error. Don’t get stuck in analysis paralysis. Just post it, move on, and do it again. Over time, you get sharper, faster, and better.
But here’s the truth they don’t put on those “Follow your dreams!” mugs: it’s so much harder than you think. It’s like when you’ve been eating junk for years and suddenly expect a six-pack because you did cardio twice and passed on a cheeseburger. Nope. Starting your own business is a grind — slow, thankless, and invisible at first. There’s little to no traction most days, and you’ll feel like quitting more than once.
But if you show up daily, stay consistent, and stop waiting for perfect? You’ll start to see momentum. And weirdly enough, you’ll grow more in six months running your own thing than you would in six years working for someone else.
So inspired by that episode, and based on everything we’ve learned the hard way, here are 10 brutally honest reasons why starting your own business might not be for you — unless you’re into discomfort, debt, and the occasional happy tear when things finally click.
1. You Actually Have to Work Harder (Like… A Lot Harder)
Forget the 9–5. Say hello to the 5–9 (yes, both AM and PM). The hustle doesn’t stop just because you don’t clock in anymore. You are the business — and the janitor, customer service rep, creative director, and unpaid intern. You're the one fixing the broken gear, fielding texts from nervous clients, and shooting for 4 hours on 3 hours of sleep.
2. You’ll Wake Up Earlier Than You Ever Thought Possible
Alarms at 6AM? Luxury. Try 4:45AM wake-ups with a mental to-do list already screaming at you. You’ll be packing gear in the dark, charging batteries you forgot the night before, and praying traffic doesn’t kill your golden hour light.
3. No One Cares as Much as You Do (Seriously, No One)
That logo you obsessed over? Your client didn’t even notice. Your new service launch? Crickets. And that post you spent three hours editing? Your mom gave it a like — maybe.
But here’s the real kicker: it’s supposed to suck at first. Like Gary Vee says, everything you write, post, or work on early on is going to be mid at best. Don’t get stuck in analysis paralysis. Just post it, move on, and keep showing up. The more you do it — like anything in life — the better you get.
And yes, it’s so much harder than it looks. You think a couple reels and a Canva post are going to launch your brand? Think again. It’s months (sometimes years) of silence, of trying new things, of learning what works — and then doing it all over again.
4. You’ll Question Every Life Choice You’ve Ever Made
Multiple times a month, possibly a day. You’ll wonder if you should’ve just stayed at that stable job with benefits, free coffee, and zero existential dread over website traffic or your last invoice getting ghosted.
5. You Can’t Call in Sick (Even When You’re Sick-Sick)
No PTO here. If you’ve got the flu, you better hope you can still hold a camera or type with one hand while sipping tea with the other. If your dog is sick, your car breaks down, or your body’s telling you to rest — too bad. You’ve got a 4PM shoot in Palm Springs and an invoice to pay off.
6. You're Going to Wear Every Hat (and None of Them Fit)
You're the CEO, CMO, CFO, and janitor. You’re also tech support when your client’s download link won’t open. Accounting? That’s on you. SEO? YouTube tutorials. Legal? Google and hope for the best.
7. Motivation Doesn’t Magically Show Up Every Day
Some days you’ll feel unstoppable. Other days you’ll stare at your screen, paralyzed, wondering if you’re in over your head. You'll compare yourself to other creators, photographers, or friends who seem like they’ve got it all figured out — spoiler alert: they don’t either.
8. You Will Miss Out on Things (Weddings, Weekends, Wine Nights)
While your friends are out brunching or sipping wine in Temecula, you’re tweaking your booking form, re-editing a gallery that “just doesn’t feel right,” or trying to learn retargeting ads at midnight with 12 tabs open and a cold cup of coffee.
9. There’s No Guaranteed Paycheck (Only Guaranteed Bills)
Money doesn’t appear every two weeks. One month you’re flush with cash. The next, you’re selling gear to pay for car repairs. Your bank account will flirt with zero more times than you’d like to admit.
10. You’ll Grow in Ways You Never Asked For
You’ll be stretched. Humbled. Burned out. Built back up. You'll learn how to light a room with a flashlight and bounce card when you forget your flash. You’ll learn how to talk to strangers, pitch your value, stand your ground, and still show up with love for the craft — even on the hard days. It’ll feel like a bootcamp for your soul. And weirdly? That’s the part that makes it all worth it.
I know sometimes when I write these behind-the-lens style blogs I might sound a little repetitive… but the truth is, I’m writing these to remind myself, too. You’ve been through the fire. You survived. You’re still here. So keep going.
Thanks for letting me rant — seriously. I appreciate you for reading.
Final Thoughts: Don’t Do It… Unless You’re Willing to Become the Main Character in a Gritty Underdog Movie
Starting your own business isn’t for everyone. But if reading this didn’t scare you off — if it made you laugh, nod, or even cry a little — then maybe, just maybe, you’re crazy enough to make it work.
And if you ever need a reminder that you're not alone in the chaos, come find us — we’re the couple with cameras, three dogs, overdue invoices, a truck full of props, and a dream that refuses to quit.
Want more behind-the-scenes stories, travel adventures, and creative photography challenges? We’d love to have you along for the ride.
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