So, You Want to be Your Own Boss?

Every time I speak to a group, I ask which of the audience members want to own their own business. Inevitably, several hands go up. I like to go around the room and ask everyone what kind of business they want to own, and why. The answers are usually pretty standard – they’ve always loved doing such-and-such, their family has a business doing x, they think there’s a gap in the market they can fill with y.

But my favorite answer, by far, if just for the sheer level of delusion it demonstrates, is when someone tells me they have no idea what kind of business they want to start, they just want to “be their own boss.” I even had a student tell me once that she wanted to be an entrepreneur because she “didn’t want to work a 9-5 job.”

I just smiled.

The biggest fallacy about owning your own business is that you get to “set your own hours.” You get to “be your own boss.” You can do other imaginary things in quotation marks.

The truth of the matter is that when you are an entrepreneur, you are going to “work more hours than you ever thought possible.” And you are going to “have more bosses than at any other point in your life.” Also, you might “gain sixty pounds of stress weight and lose the will to live.”

I’ve had plenty of nine-to-five jobs. And for the past seven years, I’ve been an entrepreneur. If all I cared about was controlling my schedule or having time with my family, I’d go back to a 9-5. Since starting Legion in 2009, I’ve cancelled more vacations, worked through more weekends, skipped more family events and missed out on more social occasions than I care to think about. And every other entrepreneur I know has done the same.

You cannot undertake a business venture because you want MORE leisure time or flexibility. The only reason you should ever start your own business is because you feel an overwhelming passion for it and you have a vision for how you are going to make a difference in the world through that business. “I am tired of my boss/schedule/company” is a terrible reason to do your own thing, because you will be burnt out, dead tired, and totally frustrated in no time.

The best story I can tell about “being my own boss” is about my maternity leave. I found out I was pregnant with my daughter Catherine less than a year after starting Legion. I spent my entire pregnancy, including morning sickness, extreme fatigue, and eventually, high blood pressure, glued to my desk, furiously making phone calls. The only time I wasn’t sitting at my desk is when I was napping underneath it, so overwhelmed by fatigue that I couldn’t keep my eyes open, but knowing I had to be close enough to answer the phone if it rang. I was the entire company for much of my pregnancy and there was no time to waste.

When I actually went into the hospital to give birth, my mother, her boyfriend and my brother had all moved in with us to work on Legion, which at that point was still not turning a profit. I gave birth on Friday, and when I looked at our checking account that day, I saw that we had $63, and that was all the money we had to support the five of us adults, and now this new baby.

I got home from the hospital on Sunday afternoon, and Monday morning, I woke up, wrapped Catherine in her Moby wrap and sat back down at my desk. My maternity leave lasted all of a weekend. I had customers to take care of, invoices to send out, and marketing work to do. There was no time to waste.

Now, is that story extreme? Yes. But it’s not that unusual. I’ve heard lots of similar stories from other entrepreneurs and it’s the sort of circumstance you have to prepare for if you think you are ready to start your own business. If you are a new business, you are going to have to be available for every crisis, every question, every emergency. And when you have a bigger business, like Legion has become, you have a whole new set of problems, multiplied by the number of employees you have.

The moral of the story is to walk into any entrepreneurial venture with eyes wide open. Owning a business is harder than anything you’ll ever do in your life. But if it is the right business – that you start for the right reasons – you’ll never want to do anything else.


by Lacy Starling, President and Fearless Leader