I quit a good banking job after making it through the recession and several rounds of layoffs. My friends thought I was nuts. I had friends take me out to lunch and tell me most people were looking for jobs, not quitting them. But I didn't quit just because I was dissatisfied. At the heart of it, I just felt like a caged animal and I knew I had to break free.
I don't regret taking the leap, but I also didn't need to be convinced nor did I carefully ask people what they thought. It's sort of something that needs to be done because you're the right kind of crazy.
The thing I've learned from trying to be independent for four years is that you always have to answer to someone. Whether it's a boss or customers or business partners or the platform provider you depend on you are never truly "free".
I don't buy this. As CEO you have the right to say "You know what Big Important Customer? You're a dick and I don't want to do business with you."
That is a strategically stupid thing to do. You may not ever actually do it. But being able to do that without having to answer to anyone but yourself is enough. There's a very real psychological difference.
You have the right to say this while being the lowest ranking employee in the company, not CEO. But when you're CEO, you have other people you're responsible for, you hired them and they depend on you being able to run the business so they can feed their families. Saying "fuck you" to the customer who is bringing you 10% of revenue is not what CEO can really do.
