What Challenges Do You Face When Becoming Your Own Boss?

We’ve all sat at our desks before, staring up the corporate ladder, dreaming of one day becoming our own boss. However, said ladder may be more difficult to climb than once thought, so you decide to quit and start your own business. Easy solution, right? Not exactly. Transitioning from a large corporation to self-employment doesn’t happen overnight.

There are challenges that many self-employed entrepreneurs face during their transition from the corporate world. We’ve highlighted a few of those bumps in the road so you can better prepare yourself for the journey of one day becoming your own boss.

Financial Security

If you like the idea of giving yourself a paycheck, you’ll first need to consider the current situation of your finances. Starting your own business isn’t cheap, so it may be wise to hold on to your previous job while you first begin your start-up to ensure financial security. The last thing you need is to find holes in your finances before your business is up and running. Budget and lay out a solid financial plan before jumping into your start-up.


Sure, the passion to be your own boss can be enough to persuade you to start your own business, but do you have the drive to get through the rocky times? To be successful, you need to believe in your business and continue working at it until it blossoms into what you had envisioned. Of course, too much passion and ignoring red flags can be malicious to your business.


As you begin your journey, it’s important to realize that it takes time, and lots of it. It’s likely you have other obligations, such as a family, another job, not to mention a social life. The journey to becoming self-employed will require hours upon hours of time to successfully launch your new business. Working the long hours can be difficult at times, but the key is to find the right balance between work and your personal responsibilities.

Fear of Failure

Even with an amazing idea, financial backup and a well thought out business plan, the reality is that 50 percent of businesses fail within the first 5 years. You have to realize there will be mistakes along the way, but don’t let them stop you from doing what you’re passionate about. Pick yourself up and learn from your mistakes.

The notion of owning your own business and being self-employed can be highly rewarding, but you need to be aware of the challenges the journey brings along the way. Have you quit your job to open your own business? What challenges did you experience? Let us know in the comments.

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