top of page
  • Writer's pictureEli Gonzalez

5 Reasons why it SUCKS to be your own boss

I'm not sure if the phenomena is sweeping across the country, but here in the Tampa Bay Area, you can't throw a rock without hitting 17 entrepreneurs.

When most people branch out on their own, they are filled with visions of success. They love the thought of being their own boss, of being in control of their own schedules, of perhaps scaling their business and providing others a means of making a living, and some even spend time thinking of the day they'll be cruising in their yachts while other people manage the business. Starting a business is an integral endeavor. I commend all of those who have the confidence to bet on themselves and forego a steady paycheck. The problem is, nobody told us how much it sucks to be our own boss!

Before I get into the top 5 reasons why it sucks to be your own boss, allow me to explain something: an entrepreneur can mean several types of people. It can mean a person who works for him or herself by him or herself. It could mean someone that started a business in a garage and now has five contracted employees working out of their respective homes. It could also mean someone who started a business and now has 25 full time employees that show up to their place of business. There are also many multi-millionaires who have built many successful businesses who consider themselves as entrepreneurs, and rightly so.

For the remainder of this article, so that it's clear, I'll be referring to the entrepreneur who works for him or herself by him or herself. That person is often referred to as a solo-preneur.

Here are the top 5 reasons why it sucks to be your own boss (as a solo-preneur).

ONE: You are your own Customer Service Department. - - Making the sale feels great. Cashing checks that don't bounce makes you feel even better. But when thing's don't go well, the same person that entrusted you with his or her hard earned dollars is the same person that you must now eat crow for. As your own Customer Service Rep, you are tasked with customer retention. At times, that's a demeaning job. It requires you to apologize for whatever went wrong.

Even when you're right, because you may not have many clients or solid testimonials of former clients, at times you will accept the blame to keep the clients you have or to at least salvage some semblance of a friendship so that your former client doesn't write a negative review about you. It's difficult to feel good about yourself when you have to apologize for not living up to your commitment. And not feeling good about yourself sucks.

TWO: You're in charge of delivering refunds. - - The main issue with delivering refunds for solo-preneurs is that most or all of the funds have already been spent! Hey, the bills have to be paid, I get it. When there's a little extra money, we spend it on marketing, restaurants (because we're always outside the house trying to conjure up business), networking events, clothes, business cards, an updated website, and the many nuances of digital marketing, which is totally different than regular marketing. When the money has been spent but you're the person in charge of delivering refunds, it sucks to be you.

THREE: You don't control your own schedule - - One of the many myths of working for oneself is that you can make up your own schedule. In the real world, when you're fighting to keep your business going or your struggling to grow enough so that you can bring on an assistant, you don't have the luxury of not meeting your prospects when they have time to meet you. If you have lunch date planned with your sweet ol' mom but a potential big client can only meet you at the same time, you'll be on the phone apologizing to Dear Mom and tell her how you're going to make it up to her with the money you're going to make from the same guy you're ditching her for.

The truth for most solo-preneurs is that they don't control their own schedules. Other people's schedules controls them. And that sucks.

FOUR: There's no such thing as a 40-hour workweek- - Tim Ferris made a name for himself by writing, The 4-hour workweek. I'm sure the fact that his book became a New York Times Best Seller and sold more than 1.3 million copies made it easier for Tim to work only 4 hours a week. But for most solo-preneurs, we're always working!

Even when we're not working we're thinking about work. We think about it while we're eating, when we're having conversation with our significant other, while we're driving, while we're shopping, and while we're trying to get ourselves to stop thinking about work. When we finally forget about work and watch television, we're back at it because a commercial or a character on the show we were watching said something that gave us a new idea on how to market our service or ourselves. It's a blessing and a curse!

A 4-hour workweek? Pssht. As if!

An 80-hour workweek more closely resembles the truth for most solo-preneurs. That sucks.

FIVE: You're your Collections Department - -

I know a landscaper who continued cutting someone's lawn for six months without pay. Why? He needed the money.

When you're establishing your business and some of your clients have fallen into arrears with their payments, it sucks to be the jerk who has to call people for money. The fact that you have worked for it and deserve it doesn't help much. If you have a service based business, it's tricky on how you ask for the money owed you because you know that there's not much you can do if they decide not to pay you.

It's not as if you have a lawyer on your payroll. It's also highly unlikely that you'll pay for one when he or she will charge you more than what's owed you. That's a sucky position to be in.

So, what should you do? You have this great idea or you have this great talent for something, but launching a business by yourself is daunting. Should you keep working for, The Man? Should you press down your desire to start your own business and take over the world? Certainly not. Go for it. Go for it, hard.

Here’s a bit of advice: Think about scaling and about how to have others share in your vision as quickly as possible. Then, execute on that plan as quickly as possible.

Trust me, when you do get to the point when you’re handing out checks to the people that work for you, and their grateful for the opportunity to work for you, and you know it helps feed and clothe them and their families, and there’s plenty of money left over for you – that doesn’t suck. That doesn’t suck at all.

37 views1 comment

Recent Posts

See All

1 Comment

Feb 02, 2021

Makes perfect sense!

Post: Blog2_Post
bottom of page