Being Your Own Boss Isn’t All It’s Cracked Up to Be

Conor Cawley

With entrepreneurship comes a lot of baggage. Between sleepless nights, hectic mornings, and a schedule that Tim Cook would shutter at, entrepreneurs are constantly inundated with problems to solve, fires to put out, and employees to deal with. But as anyone hoping to start their own business will tell you, the freedom of entrepreneurship should be enough of a reward to keep your eyes on the prize. Unfortunately, being your own boss isn't as glamorous as people think.

As an entrepreneur, you do have control over your entire company. You have the freedom to take a 3-day weekend. You have the flexibility to start work at 9:30 AM instead of 9 AM. But what TV shows, movies, and books don't tell you is that being an entrepreneur doesn't make you your own boss. It just makes you an employee of a bevy of other business factors rather than a boss on a power-trip.

One of these new bosses you'll get as an entrepreneur are your customers. As a budding startup, you'll likely be in dire need of some capital. Without paying customers, you won't be alive for long, which is why you need to dedicate all your time, all your energy, and all your capital into getting pay customers. Sounds like a boss to me.

“If you have no customers — or more accurately, no paying customers — you have no business,” said Carol Roth, author of The New York Times bestselling book The Entrepreneur Equation. “It is impossible to have a business without any customers. This gives your customers the ultimate power — basically, they own you.”

Being your own boss gets even more convoluted when you realize that investors are the ones calling the shots in your startup. Again, you need capital to run your business. And if your investors don't like the direction you're headed in, it turns out you have to do what they say. Otherwise, that capital isn't going to be around for long.

The burden of entrepreneurship does have it's rewards. In the event that you do become successful. You will have the pride and experience necessary to continue your business journey with confidence and poise. But that journey houses a great deal of failure and stress. So if being your own boss is the only reason you want to get into the world of starting a business, you might want to reconsider.

This article was last updated on:
Did you find this article helpful? Click on one of the following buttons
We're so happy you liked! Get more delivered to your inbox just like it.

We're sorry this article didn't help you today – we welcome feedback, so if there's any way you feel we could improve our content, please email us at

Conor is the Senior Writer for For the last five years, he’s written about everything from Kickstarter campaigns and budding startups to tech titans and innovative technologies. His extensive background in stand-up comedy made him the perfect person to host tech-centric events like Startup Night at SXSW and the Timmy Awards for Tech in Motion. You can email Conor at