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.

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Adapting to a new environment: What we learned (and the mistakes we made) During our first networking event photoshoot.

Adapting to a New Enviroment: What we learned (and the mistakes we made) During our first networking event shoot.

Photographing a networking event for the first time was a new and slightly nerve wrecking experience for us. We've shot fast paced, high energy events like Electric Daisy Carnival but this was entirely different. Along the way, I made a few mistakes, like leaving our flash behind and underestimating how important it was to approach guest for posed shots.

We quickly learned that networking events are all about capturing subtle moments, like a handshake or meaning conversation and that preparation is key. One of our biggest lessons was not being afraid to asked for posed shots because as the great Wayne Gretzky said "You miss 100% of the shots you don't take"

From blending into the background to learning the value of key interactions every challenge we faced taught us something new about adapting our photography skills to fit the environment. Though we stumbled a few times we walked away more prepared for future events and some cool photos to show for it.

We’ve captured everything from wild music festivals to emotional surprise proposals, high-energy graduations, and intimate maternity sessions. But when we booked our very first networking event, we quickly realized we were entering a different arena altogether.

The energy was quieter, the flow of movement more intentional, and the stakes different. It wasn’t about the biggest moment of the night—it was about the subtle connections happening in the background. And as much as we pride ourselves on adapting fast, we made a few rookie mistakes.

Here’s what we learned so you don’t have to make the same errors—and how these lessons made us better photographers for future corporate and lifestyle events.

Mistake #1: Underestimating the Pace

At festivals, everything moves fast—you have to be ready to catch those blink-and-you-miss-it moments. We walked into the networking event expecting the same level of action. Instead, it felt calm, even slow at times. We found ourselves anxiously waiting for "the shot"—until we realized the real story was unfolding in the quiet: handshakes, laughs, eye contact, introductions.

Lesson Learned: Learn to read the room. The magic is in the micro-moments. That brief smile, a shared laugh, a business card exchange—those are the moments that truly reflect the event’s purpose.

Mistake #2: Being Too Obvious

In weddings or family shoots, we’re used to moving freely to get the perfect angle. But at a professional networking event, being too visible can disrupt conversations and make people uncomfortable. I caught myself hovering once or twice—definitely not the vibe.

Lesson Learned: Be a ghost. Use longer lenses to stay back, move with intention, and blend into the scene. Discretion is your superpower at corporate or business events.

Mistake #3: Missing the VIPs

We focused so much on capturing ambiance and candids that we forgot to prioritize the key players—like the main speaker and a few vendors our client specifically invited. That was a hard one to admit.

Lesson Learned: Ask for a shot list or do your homework. Know who the client wants photos of and plan your timeline around their appearances. Those are the images they’ll use in press kits, social media, and marketing for years to come.

Mistake #4: Underpacking Gear

We made the mistake of assuming the venue lighting would be enough—so we left our flash at home. Bad move. The lighting was way dimmer than expected, and we spent more time fixing things in post than we should have.

Lesson Learned: Always bring your flash, extra memory cards, and backup batteries. Even if it looks well lit during setup, things change once guests arrive. Pack for the “what-ifs”—because they happen.

Mistake #5: Over-Relying on Candids

We initially avoided asking guests to pose, thinking we’d interrupt the flow. But we realized that intentional portraits—especially of attendees, sponsors, or client guests—are often what organizers value the most.

Lesson Learned: Don’t be afraid to politely ask for a posed shot, especially during natural breaks in conversation. If you ask with confidence and respect, most people are more than happy to say yes.

Mistake #6: Ignoring the Flow of the Room

This is one we realized after reviewing our photos: we hadn’t considered the layout of the event. Our coverage was good—but the storytelling could’ve been stronger if we had anticipated how people would naturally move from the entryway to vendor booths to the speaker area.

Lesson Learned: Take 5–10 minutes to walk the room before guests arrive. Visualize the flow. Anchor your coverage around where key moments will unfold. It helps you stay one step ahead instead of reacting to what’s happening.

Final Thoughts

Photographing that first networking event was a humbling experience—but one we’re incredibly grateful for. It pushed us out of our comfort zone and made us sharper, more intentional photographers. We now approach corporate events, branding sessions, and lifestyle content with a deeper understanding of how to tell stories that are quiet but powerful.

And yes, we still say yes to last-minute bookings—but we’re now better prepared for every type of moment, whether it’s a surprise proposal in Orange County or a branding shoot in Downtown Riverside.

Need an Event Photographer Who’s Ready for Anything?

Whether you're planning a last-minute networking mixer, launching a new brand, or throwing a milestone event in Temecula or Palm Desert—we've got you.
We specialize in fast turnarounds, meaningful storytelling, and capturing real human connection in any environment.

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👉 Book your event shoot today: https://lastminutephotoshoot.com/bookings
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