“Oops, I Did It Again” — Common Ways Businesses Fail (and How to Not Be That Business)
- Jorge Ocasio
- Jul 3
- 4 min read
Let’s talk about common ways businesses fail—not the fun, dramatic kind where someone blows all their money on gold-plated office chairs and a company llama (true story, Google it). I mean the sneaky kind. The slow, creeping, “why the f%#k are we always broke?” kind. The kind of failure that doesn’t show up with fireworks and nice music playing in the background that lifts you up—it just ghosted your bank account and left a note that says “it’s not you, it’s your systems.”
“Let’s talk about common ways businesses fail—not the fun, dramatic kind where someone blows all their money on gold-plated office chairs and a company llama (true story, Google it).”
Here’s the truth: businesses don’t fail overnight. They fail in small, preventable ways—until the whole thing collapses like a Jenga tower built by toddlers.
Let us dive in, so grab your coffee, your sense of humor, and maybe a notebook, because we’re diving into the most common business faceplants, plus how to dodge, survive, or bounce back like a boss.
No Clear Business Plan = Chaos with a Logo
The Fail: You have a logo, a name, and a burning desire to sell beard oil to the masses. But when someone asks, “What’s your target market?” your answer is, “Uh...everyone with a face?”
The Fix: Get a business plan. And no, not just a napkin sketch. We’re talking goals, marketing strategy, financial projections, ideal customer, the whole shebang. This gives you clarity, direction, and something to update when the market shifts (because it will).
Pro Tip: Use tools like LivePlan or Notion templates to map it out. And no, it doesn’t have to be a 100-page MBA thesis. Just a living document you can tweak as you grow.
Poor Cash Flow Management: Broke But Busy
The Fail: You’re selling, hustling, invoicing—but still broke. Why? Because the money’s leaving faster than it’s coming in.
Example: A bakery selling $10,000 a month... but spending $11,000 on ingredients, rent, and five different frosting suppliers.
The Fix: Track your inflows and outflows. Every. Single. Month. Get real about your numbers and stop ignoring your P&L like it’s your ex that you are still afraid of because they threw all your stuff in a pile and lit in on fire.
Pro Tip: Wave or QuickBooks are great to track transactions. A “profit first” system: pay your business and yourself—before reinvesting every dime back in.
Trying to Be Everything to Everyone = Burnout Boutique
The Fail: You sell custom mugs, do taxes on the side, walk dogs on weekends, and just launched a course on “manifesting wealth through cheese.” Don't judge me.
The Fix: Pick a lane. Then dominate it. You can always expand later, but without a strong foundation, you’re just juggling flaming swords.
Pro Tip: Rebrand. Refocus. Tell your audience, “We’re evolving,” and niche down to what actually makes money and brings joy (and doesn’t involve cheese unless you're in the dairy biz).
Ignoring Marketing Because “It’s Too Much Work”
The Fail: You built it… and no one came. Not because your product sucks, but because nobody knows you exist.
The Fix: Marketing isn’t optional. It’s oxygen. You don’t need a Super Bowl ad—just consistent visibility.
Examples that Work:
A dog groomer makes Instagram Reels and posts in local Facebook groups.
A candle shop emails their list twice a month with actual value, not just “buy this” spam.
Pro Tip: Canva + Mailchimp + ChatGPT = marketing magic for the overwhelmed entrepreneur.
Not Understanding the Difference Between a W-2 and 1099 Worker
The Fail: You hired “contractors” but made them clock in, follow dress codes, and attend staff meetings. Hello, IRS audit.
The Fix: Know the difference:
W-2 employees = you withhold taxes, follow labor laws, and usually provide benefits.
1099 contractors = independent, work how/when they want, file their own taxes.
Pro Tip: Use platforms like Gusto or ADP for payroll compliance. Consult an accountant before handing out titles like the Price is Right hands out cars.
No Customer Retention Strategy
The Fail: You spend all your money chasing new customers while your old ones leave like it’s a clearance sale at the competition.
The Fix: It’s cheaper to keep ‘em.
Set up:
Loyalty programs
Automated email thank-you's
Birthday discounts
“We miss you” coupons
Example: A small smoothie bar added a punch card offering loyalty program to customers.
Quitting Too Soon (aka “The Early Exit Syndrome”)
The Fail: You launched, didn’t make a million in 30 days, and decided to become a life coach for people who also gave up.
The Fix: Success takes time. Rihanna didn’t wake up flawless—she trained, failed, rehearsed, got booed, kept going. You need that same energy (minus the heels unless you’re into that).
Pro Tip: Re-evaluate what’s working, pivot if needed, and stay in the game longer than your doubt.
Look, failure isn’t fatal (If you learn from it). Every entrepreneur’s made a mess or three. If you’re reading this and thinking, “Well, I’ve done half of these already,” don’t stress. It doesn’t make you a bad business owner—it makes you a learning one.
Every successful founder has been there. They just kept moving, kept fixing, and kept showing up—even after the 2 a.m. crying-in-the-car moments (don’t lie, we have all had them).
Quick Cheatsheet: How to Not Fail (or Recover If You Did)
✅ Write a flexible business plan
✅ Monitor cash flow like your business life depends on it (because it does)
✅ Find your niche and own it
✅ Market consistently—even on a budget
✅ Know your team structure: 1099 vs W-2
✅ Focus on customer retention
✅ Be patient and persistent—growth is not instant noodles
Now go out there and fail forward—because that’s how legends are made and as always, sending positive vibes your way 🙏
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