How to avoid becoming the next cautionary tale in someone else’s LinkedIn post

Starting a business is like trying to bake a soufflé while riding a unicycle during a thunderstorm. It looks impressive when it works, but one wrong move and suddenly you’re Googling “how to file for bankruptcy” at 2 a.m. The truth is, building something from scratch is exhilarating, but it’s also riddled with opportunities to mess up in spectacular and occasionally hilarious ways.

So, I talked to real business owners, advisors, and people who’ve been there, done that, and lived to warn the rest of us. If you’re about to launch your dream biz—or you’ve already soft-launched it with a Canva logo and a prayer—please read this first. Because while mistakes are part of the journey, a few of them are totally avoidable if you know what not to do.

Let’s start with the big one: being afraid to fail. Yes, I know that sounds counterintuitive. But if you’re waiting until everything is perfect and risk-free, you’ll be waiting forever. Failure is part of the startup starter pack. It’s not fun, but it’s how you learn to do better next time. So fall down, get back up, and maybe document the chaos for your future memoir.

Another surefire way to derail your launch? Not making a business plan. I’m not saying you need a 72-page investor deck with ten-year projections, but you do need to know things like: how much does it cost to run this thing, who are you selling to, and why would they buy from you instead of someone else? Winging it works for road trips and karaoke, not for staying solvent past month three.

Organization is your best friend, even if your brain is powered mostly by iced coffee and chaos. Running a business means juggling approximately 64 things at once, including things you didn’t even know existed (like trademark law or quarterly tax estimates). A simple priority list can save your life—or at least your lunch break.

Speaking of lifesavers, please define your market. I know you want everyone to buy your thing, but “everyone” is not a target audience. Find your niche. Get weirdly specific. Imagine your ideal customer, give them a name like “Podcasting Penny” or “DIY Derek,” and market like you’re writing love letters directly to them.

Also, please, for the love of legal sanity, set up the right business structure. LLC, sole prop, S-corp… it matters. Not just for taxes, but for protecting your personal assets if things go sideways. And don’t skip contracts. Your best friend today could ghost you tomorrow if there’s no paper trail. Having it in writing isn’t untrusting—it’s responsible. Like carrying an umbrella even if the weather says sunny.

Now let’s talk about a classic mistake: doing everything yourself. Look, I know you’re scrappy and multi-talented and have a color-coded Asana board, but even superheroes need a team. Surround yourself with advisors who’ve done it before. Ask questions. Share your ideas. Build your own little league of extraordinary humans who will gently tell you when that pricing strategy is bonkers.

While we’re here, a quick note about investors. If someone offers you money but also gives you the ick? Don’t take it. Investors aren’t just financial—they’re like unofficial co-parents to your business. Make sure you vibe. If they’re going to question your every move or push your vision off a cliff, say no. There are better fits out there.

Avoiding contracts is another rookie move. It’s easy to trust people when everyone’s enthusiastic and things are going well. But when projects shift or money’s late or someone suddenly gets amnesia about your agreement, you’ll wish you had it in writing.

Oh, and don’t hire too fast. I know it feels legit to say “I have a team,” but early on, contractors and part-timers are often a better move. They give you flexibility without locking you into overhead you can’t afford. Which brings us to: capital. You’re going to need more of it than you think. Plan for delays, hiccups, and surprise costs. Budget like you’re building a spaceship on Mars where nothing goes to plan.

Also: don’t set your salary by vibes. Too high and your business can’t grow. Too low and you start to resent your own company. Tie it to revenue or some other solid metric so you’re not working 70 hours a week for a glorified title and no groceries.

While we’re on the subject of money, please don’t undervalue your product. Yes, it’s tempting to discount everything or work for free to “build exposure,” but that often attracts clients who want something for nothing. Price like you believe in what you’re offering. Because if you don’t, no one else will.

Launch timing matters too. Don’t rush it if your backend systems aren’t ready. You might only get one shot to impress those first customers, and if things are glitchy or inconsistent, it’s harder to win them back.

And don’t expand just because something went well once. Scaling takes strategy. Hire slow. Spend slower. Growth is exciting, but it’s also a test of your foundations. If those aren’t solid, things will crack the minute your audience doubles.

Get a bookkeeping system. Seriously. Even if it’s just a Google Sheet and a dream at first, keep your finances clear. You want to be the kind of person who knows their monthly burn rate, not the one who finds out they’re broke via a bounced payment.

Create a marketing plan. Not just “post on Instagram when I remember.” Think through how you’ll get users, how you’ll convert them, and how they’ll become your biggest fans. Marketing isn’t just about getting noticed—it’s about building momentum.

And finally: don’t hire the wrong people. Early-stage teammates should be scrappy, adaptable, and cool with doing a little bit of everything. Don’t bring in a specialist when you need a Swiss army knife. And don’t hire someone just because you like them. Hire because they solve a real need.

Running a business is hard. You will mess up. That’s part of the deal. But if you can avoid these rookie mistakes—or at least recognize them when they sneak up on you—you’ll be a lot closer to turning that messy, magical idea into something real.

And hey, when in doubt? Take a breath. Eat a snack. Write a new to-do list. You’ve got this. Even if you’re still figuring it out, you’re doing more than most people ever dare to try.