It is, in many ways, the call of the siren. We find ourselves being beckoned to take the risk, make the leap, gamble it all in the cause of greater promises. To some, it remains the American dream. To other, a bridge too far to even attempt in crossing.
It is that wistful hope of owning your own business. where the roads can all be paved with gold and the naysayers will drown in their hawking of doom.
How am I doing for drama?
Think of it. You are your own boss. Big cheese, head honcho, Numero Uno, top dog, main man, woman with a righteous cause, the last stop where the buck stops here with no doubt who is in charge.
You call the shots, and no one tells you what to do. Well, almost no one.
Except for customers, employees, suppliers, your accountant, and possibly the IRS, you are all powerful and mighty.
But hey, it’s your dream, so let’s lean into it.
Here are the top five sparkling positives of being a business owner, along with five delicious pitfalls that will keep you on your toes—or curled up in the fetal position, depending on if its a day ending in “Y”.
The Positives
Total Control Over Your Destiny (a.k.a., All the Responsibility) Ah, the sweet smell of power! As a business owner, you get to make all the decisions. Want to close shop early? Sure thing. Need to change your brand color from blue to chartreuse because Mercury is retrograding? Go for it.
The Reality: While you bask in the glow of this autonomy, remember that the same people congratulating you will also blame you when things go sideways. Enjoy deciding whether to reinvest profits or just blow them on a stress-induced, luxury vacation you can’t actually afford.
Unlimited Earning Potential (Technically) Theoretically, there’s no cap on your income. Elon Musk, Jeff Bezos, and Oprah started somewhere, and so did you. This is your chance to become a billionaire… or at least make enough to pay your electricity bill without crying.
The Reality: Unlimited potential often translates to limited actual earnings for a while. You’ll quickly discover that “profits” mean whatever’s left after paying everyone else’s salary, rent, marketing costs, and that inexplicably high water bill.
Flexible Schedule (a.k.a., No Schedule at All) Business owners love to boast about “setting their own hours,” which roughly translates to working 80 hours a week so they don’t have to work 40 for someone else. Sure, you can start your day at 10 a.m. and end it whenever your laptop finally overheats.
The Reality: Flexibility means you’re working during holidays, weekends, and that family reunion everyone else seemed to enjoy. But hey, at least you can take a call in your pajamas. Well, in the ZOOM world you’ll have to learn the fine art of dressing only from the waist up while ensuring the cat isn’t digging into that little box just in camera view over your left shoulder.
Building Your Legacy (And Your Migraine Collection) You’re not just running a business—you’re crafting a legacy. One day, your great-grandkids will marvel at how you grew a taco truck empire or single-handedly revolutionized artisanal dog leashes.
The Reality: While they’re marveling, you’ll be wondering if that legacy is worth the sleepless nights you just spent begging the bank for a line of credit.
Creative Freedom (Within Reason) Want to launch a goat yoga studio or a kombucha brewery that also sells handmade candles? Go for it! As a business owner, the world is your oyster—as long as you can sell it to customers.
The Reality: “Creative freedom” sometimes means trying to explain to investors why you thought a raccoon as a mascot was a good idea. Spoiler: it wasn’t.
The Negatives
Taxes: Your New Best Frenemy Taxes are like that clingy friend you can’t avoid. You don’t just pay them—you navigate them. Quarterly filings, payroll deductions, and a tax code that reads like it was written in ancient Sumerian are all part of the joyride.
The Sarcastic Silver Lining: At least you’ll get real cozy with your accountant, who may or may not be calculating their rates by the sigh.
Employee Drama: Live Soap Opera, Business Edition Managing people is rewarding! Until it’s not. Expect sudden resignations, passive-aggressive Slack messages, and Karen from HR’s third meltdown over the coffee machine.
The Sarcastic Silver Lining: At least you’ll have stories for your memoir, like the time Bob called in sick but posted beach selfies on Instagram. Thanks, Bob.
The Market Never Sleeps (And Neither Do You) Running a business means keeping up with trends, competitors, and that random tweet Elon Musk just posted, which somehow tanked your stock prices. If you’re lucky, you’ll sleep… eventually.
The Sarcastic Silver Lining: Coffee is a small business owner’s best friend. Bonus: your local barista will know your life story by month two.
Customer Expectations: Impossible, Yet Mandatory Today’s customers expect next-day shipping, 24/7 support, and personalized thank-you notes written in calligraphy. Oh, and they want it all for 10% less than your competitors.
The Sarcastic Silver Lining: At least their one-star Yelp reviews will be hilariously petty. “The napkins weren’t folded properly… would NOT recommend.”
Burnout: The Gift That Keeps on Giving Owning a business is exhausting. By year three, you’ll wonder if you’ve aged in dog years. But don’t worry; burnout is just your body’s way of reminding you that sleep is a thing.
The Sarcastic Silver Lining: Burnout might be terrible, but at least you’ll look distinguished with those new stress lines. Who needs Botox?
Final Thoughts
Owning a business is a wild ride—part adrenaline rush, part existential crisis. It’s not for the faint of heart, but it’s also incredibly rewarding (most of the time). Embrace the chaos, laugh at the absurdity, and keep moving forward. Because at the end of the day, being a business owner is all about the journey… and maybe a few well-mixed cocktails along the way.
Ed Berliner knows this subject matter, having been on the creative and management team for 6 broadcast cable networks, having started four successful entrepreneurial media businesses, and taken his share of lumps along the way. He now writes about business as the Executive Producer and Lede Columnist for the email newsletter, "The Business Beagle", and serves in those capacities for the popular email newsletter about news, sports, politics and everything in between, "Shakedown Street". Ed invites you to join the fray and sign up for both, thus helping another small business.
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