I like introducing people. Whether it is romantic matchmaking or a great bizdev partnership or finding the right person to fill a job, there is a certain rush you feel when you connect the dots in just that certain way and it all fits together.*
The side effect is that I spend a lot of time talking to people about what they want to do in life, since that forms the basis of figuring out a good pairing for them. And this has a notable downside: I hear the phrase “be my own boss” far, far too often. It sets my teeth on edge and the word “entitled” flashes from the sky like a lightning bolt. If my blood were not bossed around by physics, it would instantly boil.
The response comes at a fairly predictable juncture, where people start talking about why they left what they were doing and what they are looking to do next. It is especially prevalent among people who are thinking about going into startups, without really having any idea what one is. They are often the same people that think “more freedom” means “more options” and I suspect them of having bad musical taste as well.
Put simply: you are never your own boss. You could make an argument about how you always have a choice and you really never have to do anything, but back here in reality, most people need a steady source of income, which means a job, which means a boss.
Now, you may want your boss to be your customer, and that is certainly something entrepreneurship brings. But if you couldn’t learn to please your boss at your previous job, chances are you’re going to both chafe and be bad at pleasing customers as well. An orientation towards fulfilling needs is a stable, portable characteristic: quitting your job and starting a startup isn’t going to make you magically care about meeting the needs of others.
The important choice we do have is not whether or not to have a boss, but who (or what) our boss is going to be. Because in the end, the ultimate boss is simply responsibility: whatever thing we need to do in order to fulfill our role in the machine. Serving customers through entrepreneurship is still part of that machine and just like physics keeps my blood from boiling, the same rules apply no matter what the role. Designers design, founders found, coders code, but it is always in service of an outcome. So pick your outcome.
* As a complete side note, there is some great research that shows that we are evolutionarily wired to get a little burst of pleasure from resolving incongruity and ambiguity. Which makes sense, in that the person who enjoys seeing the tiger in the trees is going to have an extra shot at running away.