Don't Start A Company to Be Your Own Boss

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TL;DR: Everyone is your boss.

When I worked at Green Dot and people asked me at a party or get together what I did for a living, I would say that I worked in financial services. This ended the conversation pretty quickly. Now I say something like “I have a software startup.” A frequent response now is “I’d like to be my own boss.”

Sorry to disappoint, but working for yourself is never working for yourself.

The politicians and media in this country have really glamorized startups and small business owners. While I think many of us love our job (I do!), I doubt you find a lot of small business owners truly characterizing themselves as their own boss. We all know that when you’re in charge, everyone is your boss. 

First, if you have investors, you are working for them. They are providing the capital for your business and you have a fiduciary responsibility to return their investment with profit. Unless you’re Mark Zuckerburg, they can probably fire you, too, via the board, so they are truly your boss.

Second, you have your employees. They may technically work for you, but let’s be honest, you work for them. In a small business, your business is your team. This is doubly true for a software company. I can write code, but not well. If my team walked out one day, I would be extremely hard pressed to remain a going concern. Your employees represent you to the world and build and deliver your product. Without them you have some assets that probably don’t work.

That’s why you have to keep them engaged and satisfied. This isn’t to say that you should break the basic tenets of management and not provide guidance and oversight, but rather that you need to be aware of their opinions, attitudes and contributions. You need to take advantage of their skills to make your company better and grow.

Third, you have your customers. Without customers, there is really no point. Sadly, many startups stumble along without customers for a long time. Some people think they are Steve Jobs and can tell the customer what they want.  Good for them, but that probably doesn’t apply to most companies. You must build products that someone wants to use and, ideally, that generates revenue.

As many others have said before me, when you work for yourself you are not your own boss. That doesn’t mean that there aren’t many, many great advantages.  There is often a huge advantage in control over your own schedule, your own daily tasks and more.

I love being a founder and CEO.  Maybe it’s that I’m a narcissistic, optimistic control-freak. Maybe it’s because the times I have worked for myself have always been my most fun jobs (I never watch the clock when I’m in these jobs.)  Either way, I know I’m not my own boss. I hope I’m doing a good job for my many bosses and that the year-end evaluation goes well!

Edit: Comment Thread on Hacker News