Being Your Own Boss – Toughest and Most Rewarding

I have been an employee of a couple of Fortune 20 companies. I have been my own boss. I have been an employee of a startup, and now CEO of a SaaS technology company. I have seen all ends of the spectrum and each has its own advantages. Ever since I was a kid, I wanted to own my own company and be my own boss. I always wanted a soccer store. I loved soccer so why not own a store in something I loved? Then, in college, I majored in Entrepreneurship. The idea to own your own thing is something many kids, my son included, dream about, and I am often asked what it is like to be your own boss.

I never really know how to answer that question. I feel like I should be honest with the people asking, as they think they want to be their own boss, but I don’t think that’s really what they want. I was fortunate enough to be my own boss for 12 years, and it was the most nerve-racking and lonely period. I was truly my own boss, our company didn’t have a board, we didn’t have investors, we didn’t have bankers, we had nothing but ourselves. And dammit, it is tough. 

I also suffered through a very common retail fear that tomorrow, no one will show up, ever again. Since we were at it alone, I never really celebrated when we had the best month ever. After all, I feared no one would show up next month, so why celebrate the past? That already happened. I was often consumed with decisions that I just struggled to make; some of them would completely annihilate the company if it were a bad decision. I struggled with analysis paralysis, wanting to ensure I knew everything possible. The only thing that got me through this was my dad’s constant reminder that once you make a decision, you don’t get to go back and redo it, you make it and live with it.

What’s most interesting about going out on your own is that you don’t have the support staff out of the gate. You can’t hire a top-tier senior leadership team unless you have gotten some funding – but if you got funding, are you really your own boss? When the trash has to go out, you have to be willing to be the janitor. When the phone rings, the customer service rep. When the check bounces, the accounts receivable. I think you get the point. 

Obviously I am speaking about truly starting your own thing, but as I alluded to, you are only your own boss if you own it all. And if you own it all, it will be the toughest and most rewarding thing you will ever do. So stop reading this, quit your job, and start your own company now. 

Okay, maybe don’t follow all of my advice.