5 Dark Sides To Being “Your Own Boss”

Entrepreneurship is sold as a sexy career choice for young millennials, but beneath the surface of a path that allows one to set their own schedule, travel when they want, and work from home is a darker truth. Being an entrepreneur is one of the most rewarding choices you can make, but it comes with a cost. I learned a lot when I decided to run my own business (and I am still learning). Here are five dark truths to consider before jumping into being your own boss.

Lacks ‘The Glamour’

In the beginning, you better NOT expect fame or glory. Even after rising to the status of an established business owner, entrepreneurship is not the glamorous world of working the 4-hour work week schedule. The thing about being an entrepreneur is that your work never ends, and you have to wear multiple hats within your business. That means, you get the glamorous tasks like unclogging toilet for tenant or driving across the state to meet with a client. As a business owner, you will have to learn to take the good with the bad, and the unglamorous before the glamour.

The Sacrifices

I’ve heard a saying that goes, “You can have it all, but not all at once.” I think this to be true, and I would rather live by this mindset than the more popular one that states, “You can’t have it all.” You can have what you want out of life, and I believe all of it, but not all at once. Everything requires a sacrifice; whether that be time, money, family, or resources. Decide what you will compromise on and what you will NEVER bend with. With one of the first companies I started, I had negative funds in my bank account. The bank provided me an “unofficial loan” when I overdrew from my account. Once I began bringing in profit, I paid that money back. During that time, I made a lot of sacrifices, and I still do. The friends that I had during that time I no longer associate with. They were bringing me down rather than pushing me up. Being an entrepreneur takes sacrifice.

It’s “Your Call”

Every decision and direction is up to you. That can be ‘freeing' as an entrepreneur, and equally as stressful. There will be no one there to “hold your hand.” I’m not saying, don’t have a mentor, as that is extremely important to success, but what I mean is that you have to be strong, relentless, objective, and confident in who you are and what you can do for your company. Take a minute to read Ralph Waldo Emerson's poem on self-reliance. It was a game-changer for me.

Ralph Waldo Emerson Self-Reliance

Constant Improvement

As an entrepreneur, you must always improve. Manage your weaknesses and capitalize on your strengths. Read to improve your mind. Learn from others. Stay ahead of the curve. Otherwise, you will not make it in business for yourself. As it is said, "Once a trend hits ‘trend status,’ the trend is already over." Be the one who is always improving so that you can be ahead of the crowd.

Taking a Pay-cut

Don’t think that when you become an entrepreneur you will all of a sudden be able to pay yourself more. Actually, you will most likely take a pay-cut. Your business will need the money. Your employees must get paid. You are of last importance when it comes to accounting. To be transparent, I am the least paid at my organization, and I am fine with that. That money that could be used towards my salary goes straight to advertising, which brings in more business leading to the growth of the top line revenue.

The Bright Side

Of course, it’s not all darkness as an entrepreneur. There are some who make it and make it big. One must first endure the darker sides before making it to the moment where they think, “This is all worth it.” Take on the mindset that you will embrace every challenge and work through discouragement. Building anything takes a lot of work, and entrepreneurship requires that you put in time and energy. If you only want a hobby or side-gig, that’s different. Let your goals guide you and remember to look at them everyday.


One thing to really consider is if you are cut out to be an entrepreneur or not. Some just aren’t. As a kid at school, I was in my element— between classes— when I could sell anything and everything to my classmates. Entrepreneurship was something in my blood, but that doesn’t mean that I didn’t have to make sacrifices and work hard. The path to working for yourself and building a company isn’t for everyone. Talent won’t take you the whole way either. You will have to decide and work—and continue to work! When you do this, you will make it past the dark sides and downsides.

Sterling White Elite Real Estate Investor