Being Your Own Boss Is Risky — Are You Ready?

by | Mar 8, 2022

The 2020s have marked the beginning of a new era — the era of being your own boss. In 2020, 36% of U.S. workers, or 59 million Americans, reported freelancing within the last year. In a similar vein, 62% of Americans stated that they want to start their own business someday. Why? Well, people want to be their own boss. They want to have the flexibility and authority to travel, take time off, add extra work, work from home, and set their own schedules. They may even have ambitions of growing their own company. 

While all of that can sound great, it’s important to also assess the risks of being your own boss. Working for yourself can be both rewarding and flexible but can open you up to added stress, responsibilities, and costs. Here are our top 4 factors that you should consider before deciding to work for yourself. 

Say ‘Bye-Bye’ To Your Benefits. 

One of the major perks of working for a sizable company is the benefits. From health insurance to paid time off, benefits will almost certainly cost more if you’re working for yourself. Why? Well, insurance companies have deals with businesses that allow them to drive the prices down for individual employees. You’re not going to get that benefit if you start working for yourself, and after a while, those costs can pile up.

Heavy Is The Head That Wears The Crown. 

A male businessman's hand holding a golden crown on an open palm. Invitation to fist class. Join privileged group. Fame and success.

A wise man once said, “With great power comes great responsibility” — and being your own boss is no exception. When you decide to work for yourself, your successes and failures are your own. While that may add some unique challenges to your workday, it can also be very rewarding. It all depends on what you’re willing to give up and what you think you can handle. 

It’s All Up To You. 

One of the biggest benefits of working for an organization is that you don’t have to figure out everything for yourself. But when you’re your own boss, you have to do everything for yourself. From renting a workspace to figuring out how to work any new program, it all falls on your shoulders. That’s why it’s essential to be prepared for your newfound level of independence before taking the plunge and starting your own business. 

Be Prepared For Regulations, Regulations, Regulations 

rubber stamps marked with regulations and rules

When you’re the boss, you have to deal with regulations. That includes items like taxes, trademarks, and maintaining licenses and certificates. If you’re not confident in your abilities to navigate such things, that could mean you’ll be looking at some costly legal fees. The number of regulations you will have to deal with will depend on what services you offer and your industry, so it may be worthwhile to consult a colleague in your field or do research to better gauge what the legal burden will be for you specifically. 

While being your own boss does come with unique risks, it can also be very rewarding. That’s why it’s important to be prepared and think through how your obligations will change when you decide to work for yourself. That way you can set yourself up for success in the long run.

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