The Hilarious Struggles of Wearing All the Hats: Owning Your Own Business

Victoria Kasdan
Founder & CEO / Mission Made Possible, LLC

Owning your own business sounds like a dream come true. The freedom! The control! The ability to work in your pajamas! But let’s be real folks. It’s not all sunshine and rainbows. If you’ve ever owned a business, you know that it often feels like you’re juggling flaming swords while riding a unicycle on a tightrope. Here’s a humorous take on the many hats you wear and the daily struggles that come with running your own show.

Juggling Flaming Swords: The Many Hats of a Small Business Owner

The CEO Hat: Master of the Universe

When you start your own business, you might imagine yourself as a powerful CEO, commanding an army of employees, attending glamorous meetings, and making decisions that change the world. In reality, you’re more like the captain of a very leaky ship, desperately bailing out water while trying to steer towards that distant, elusive island of “Success.”

The Salesperson Hat: Pitching Like a Pro

Selling your own products or services is a unique challenge. On the one hand, you’re passionate about what you’re offering; on the other, convincing others to share that passion can feel like trying to sell ice to a polar bear. You end up honing your sales pitch in front of the mirror, wondering if maybe you should have pursued that career in acting after all. After numerous failed attempts, you might start to feel like that annoying infomercial guy, only less enthusiastic and without fancy gadgets. It’s a bit like being in a comedy sketch, but without the laughter.

The Accountant Hat: Crunching Numbers and Crushing Dreams

Ah, the joys of bookkeeping! You start out thinking it’s just simple math, but soon, you’re knee-deep in receipts, invoices, and the nightmare that is tax season. You’ve got spreadsheets open on every device and still can’t figure out where that extra $50 came from or, worse, where it went. At some point, you seriously consider using Monopoly money because it seems less complicated. It’s like being in a never-ending puzzle game, but without the satisfaction of solving it.

The Marketer Hat: Social Media Maven

Being your own marketer means mastering the fine art of self-promotion without coming across as desperate. You find yourself posting on social media at odd hours, trying to get the algorithm to work in your favor. Hashtags, trends, SEO—these become the buzzwords of your life. You know you’ve hit rock bottom when you start analyzing your cat’s Instagram account for tips on how to boost engagement.

The IT Specialist Hat: Tech Guru

When you own your business, every tech issue becomes your problem. Printer jam? You’re on it. Website crash? Roll up your sleeves. Wi-Fi down? You’re suddenly a network engineer. You quickly realize that “turn it off and on again” is the extent of your tech knowledge and wonder if maybe you should have paid more attention to that computer science class you took or didn’t take in college.

The Customer Service Hat: Always Be Smiling

No matter how bad your day is going when a customer reaches out, you’ve got to channel your inner Mary Poppins. Polite, helpful, and upbeat—that’s you! Even when the customer is clearly wrong, you smile through gritted teeth and promise to fix the issue. After all, “the customer is always right,” even when they’re not.

The Therapist Hat: Managing Stress with Grace

Being your own boss means you’re also your own therapist. The stress of running a business can be overwhelming, and sometimes you need to talk to someone who understands—except that someone is usually yourself. You give yourself pep talks, read motivational quotes, and occasionally have a good cry in the bathroom. Self-care becomes a crucial part of your schedule, squeezed in between client meetings and inventory checks.

Conclusion: Laughing Through the Chaos

Owning your own business is undoubtedly challenging, but it’s also incredibly rewarding. The freedom, the control, and yes, even the chaos make it all worthwhile. So, the next time you’re feeling overwhelmed by the hats you must wear, remember to step back and laugh at the absurdity of it all. Because if you can’t find humor in the daily grind, you might as well go back to that 9-to-5 job—and we all know that’s not happening!

In the end, embracing the chaos and finding humor in the struggles is what makes the entrepreneurial journey unique and fulfilling. Believe me, I know from personal experience. So, here’s one word of advice from one small business owner to another: Keep juggling those hats and putting out or preventing fires.  Meanwhile, don’t forget to enjoy the ride!

Victoria P. Kasdan is a dynamic executive, leadership coach, consultant, and strategist who excels in helping organizations turn challenges into stepping stones for growth and success. As a keynote speaker and trainer, Victoria inspires and empowers leaders across various sectors. She is also the founder of Mission Made Possible, LLC, a successful consulting firm based in Southwest Florida, dedicated to driving impactful change and strategic development for nonprofits and businesses alike. Connect with Victoria on LinkedIn or visit her website to learn more about her transformative work at