During the height of the pandemic, it felt like the internet was trying to encourage anyone who would listen to start a business, launch a product or pick up a side hustle. The rhetoric was that if you had not done so, you were wasting this precious “free time” we had been given. The push for entrepreneurship was intense. Owning your own business provides a different level of freedom, expanded creativity, and the opportunity to see your dreams come to fruition. But that doesn’t mean it’s easy. Here are some of the challenges of being an entrepreneur. 

Being the One to Take the Fall 

When you work for a corporation, there’s always someone to blame be it the CEO, upper management, or even HR. When you’re an entrepreneur, the buck stops with you. Whether you’re a one-woman band or you have a team working on your vision, if something goes awry, all eyes are on you to fix it. 

No Benefits 

In addition to a check, a 9-5 gig also comes with other goodies. When you’re traditionally employed, you can receive health insurance, meaning you don’t spend thousands of dollars on medical care. Many jobs offer a 401k, so the work you do now benefits you in the future. When you work for yourself, it may take you a long time before you’re able to offer these type of benefits to yourself, let alone future employees. In the meantime, it may mean paying out of pocket. 

Being Payroll

It’s one thing if you can’t afford to pay yourself for a few weeks. It’s an entirely different story when you’ve hired employees and they’re looking at you to help them support themselves and their families. The pressure is real. And it’s not to be taken lightly. When you hire employees, you need to be sure that you can maintain the responsiblity.

Inconsistent Paychecks

Traditional employment often means payday is like clockwork. When you’re an entrepreneur, especially if your work is contracted and short term, checks are less consistent. Entrepreneurs have to be good at managing money, especially when they may have to wait up to 90 days for payment. 


When you’re the person responsible for coming up with the ideas, executing them, hiring, firing and everything in between, it can begin to weigh on you. It’s more responsibility than most people can understand. May entrepreneurs just walk away from it all because they find that the quality of their overall life begins to suffer. If you embark on this journey, you’ll have to be strategic about ways to pour back into yourself.