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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Four Years Into the Unknown: A Personal Story of Growth, Setbacks, and Self-Reflection
Four years ago, we left our stable jobs chasing a dream we couldn’t fully define—but felt in our bones. What followed was a rollercoaster of uncertainty, financial hits, caregiving, and growth we never saw coming. We weren’t ready then—and maybe that’s the point. Through setbacks, debt, late-night deliveries, and full-time caregiving, we learned how to slow down, get present, and finally become the kind of people who can live that dream. This isn’t just a story about photography or going off-grid. It’s about self-reflection, personal evolution, and trusting the process—especially when it’s uncomfortable. If you’re in the middle of your own pivot, we hope this helps you feel a little less alone.
Four years ago, my wife Stephanie and I made a decision that changed everything. We walked away from comfortable, steady paychecks to chase something we couldn’t quite explain—but deeply believed in. We wanted freedom, creativity, time together, and the space to build something on our own terms.
What we didn’t realize back then was how much the journey would test us—and grow us.
Whether you’re planning a shoot, dreaming up a creative project, or just want to chat—we’re all ears. Let’s build something beautiful together, one memory at a time.
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Before the Fall
We were still working our 9–5s when COVID hit.
I had just been promoted to Store Manager at a luxury clothing store in Palm Springs. Stephanie was working the front desk at her parents’ small photography business. When the pandemic swept in and everything shut down, we were both furloughed.
Those first few months were filled with uncertainty and unemployment checks. Like many, we felt displaced—grateful for the pause, but unsure what would come next.
When we were called back into work, we walked into a completely different world.
Policies were changing daily. I found myself managing a business while trying to enforce new health mandates I had no experience with. Stephanie was doing the same on her end. It felt like we were just surviving. And that’s when we had to ask ourselves: Is this really the life we want to go back to?
The answer was no. So we left.
We stepped away from the familiar and into the unknown.
The First Year Was the Hardest
What we didn’t realize was how quickly things could unravel.
I had invested everything we had left into crypto—believing, like many others, that it was the golden ticket. And for a moment, in late 2021, it looked like I was right. But when the market crashed, so did our safety net. Our portfolio dropped by 90%.
My inner voice was screaming at me to sell what we had left. But we stayed strong—diamond hands, as some people say. We pivoted. We leveraged what credit we had, took on a lot of debt to hold us through the winter, and waited for things to turn around.
And eventually—they did.
But in between, we weren’t just sitting around hoping. We knew we had to develop better habits. So we got to work. We focused on what we could control—our health, our mindset, our communication. We started learning new skills online. We built ourselves up quietly, brick by brick, while the world around us still felt unsure.
Although we had to put our dreams on pause again, I’m actually glad we did—because we weren’t ready to live our dream with the version of ourselves we were back then.
We were spending more than we generated.
Living like we still had a steady paycheck every two weeks.
You only get from the universe what you put into it—and we hadn’t put in the work yet.
So if you're asking yourself, “Am I ready?”—I think you already know the answer.
Only you know how much work you’ve put in to get where you are, and where you want to be in the next one to three years. One of my favorite quotes is from Jocko Willink. He says:
“Didn’t get what you wanted? Good.”
I can hear him now:
“Oh, you didn’t get to chase your dream? Good. Now you can save more, build more, and be better—so when you do chase that dream, you’re ready.”
That’s stuck with me.
Trust in the process.
Trust the person you’re becoming.
Doing Whatever It Took
We started delivering food through Uber Eats and DoorDash. I became a full-time caregiver for my mom, who’s in the late stages of Parkinson’s and now completely immobile. Steph and I tag-team her care—meals, cleaning, bathing, whatever’s needed.
It wasn’t the life we imagined. But it gave us something unexpected: perspective.
Caregiving shifted how we see the world—and how we move through it.
It made us slow down.
It made us more present.
It helped me become less reactive.
I smile more now, despite what the world throws at us.
That season of service reminded us what actually matters. It showed us how strong we could be, even when things felt uncertain. It helped us take a step back, so we could eventually move forward.
We stopped pretending we had it all figured out and started doing what we had to do.
We developed better habits—financially, emotionally, and creatively. We lived leaner. We got sharper. And through it all, we kept pouring into Last Minute Photoshoot, the business that’s now become our heartbeat.
We kept learning. We kept dreaming. We kept showing up.
Now: On the Road to Something More
Four years later, we’re finally preparing to do what we set out to do from the beginning.
By the end of this year, we’ll be living on the road with our pups—traveling the coast, shooting the life around us, and running our business wherever we go. We’ve spent years putting everything on pause to care for family. And while it’s hard to pass that responsibility to someone else, we’ve realized this simple truth:
Life doesn’t wait.
And if we don’t take the leap now, we may never.
If You’re Still in the Middle of It…
If you’re in that blurry space—wondering if you messed it all up, if it’s too late, if the dream is slipping away—just know: we’ve been there.
Some days, we’re still there.
But here’s what we’ve learned:
Growth doesn’t happen in comfort.
Change doesn’t come without struggle.
And you don’t have to have all the answers to move forward.
We’re still figuring things out. But we’re doing it with intention, with love, and with faith in the life we’re building—one mile, one lesson, and one photo at a time.
Let’s Connect—For Real
If you’re in the thick of it right now—trying to figure things out, questioning your timing, wondering if it’s too late—we see you.
And if you just need an ear… we’re here.
If you’re working through your own leap of faith and want to connect, collaborate, or just share your story—we’re all ears.
Reach out to us.
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We’ll respond with love and kindness—always.
Let’s lift each other up.
Because no one gets through this alone.