Every time I work for someone else, I spend a lot of time fantasizing about quitting.
I love work. I enjoy being productive. I get excited about accomplishing goals. But I chafe when I work for others. It doesn’t matter who the boss is. It doesn’t matter how well he treats me. If I must take orders from someone else, I’m unhappy — no matter how nicely the orders are given.
Early in my life, I always blamed the boss. For years, I thought that each boss I had was dumber than the last one. I’ve told you before about how my arrogance about my boss almost got me fired from my first full-time job. (I really should have been fired, but luck got me promoted instead.)
The pattern continued. Every boss I had seemed terminally stupid. I knew more than they did and I had no respect for them. Even though I obeyed their orders — for the most part, at least grudgingly — I chafed and I knew I could have done their jobs better than they did.
It took me a long time to have an epiphany.
My bosses hadn’t been the problem. I had been the problem. No matter the boss — some good and some bad — I had trouble simply because I’m not wired up to take orders well.
I’ve come to accept a simple truth. I need to work for myself. If I’m going to work for an idiot, that idiot might as well be me.
I’ve also come to accept something else — and this applies to everyone. It’s ultimately a problem to work for someone who you don’t respect and who you don’t admire.
This is been a problem for me, because I’ve always felt that I was smarter and more competent than the people I worked for. Whether I was right or not is immaterial. The dynamic of my belief caused problems for me.
I understand now that the only way I can be happy in the long term working for someone else is if that person is smarter than I am and more capable than I am — enough that I have tremendous respect for the person’s complete capabilities. Otherwise, I’m always going to be second-guessing that person. I’m always going to be thinking that we should be following my instincts. I’m always going to believe that I ought to be the one giving the orders.
This is a strong reason that I am happiest when I’m self-employed.
The happiest I’ve been in the past was when I was a self-employed consultant. I had clients to whom I had to answer, but I chose my clients and I could walk away from clients I didn’t want. If I didn’t want to be at a certain place at a certain time, I simply did what I wanted to do. As long as I achieved the goal I was being paid to achieve, I did things my way.
I had no employees to control. I simply had vendors to whom I contracted everything I didn’t want to do. It was a perfect arrangement for me. I was the one who was seen as having the expertise, so clients paid me for my knowledge of what to do — and then I paid others to do the work I preferred not to do.
Working for someone else is like living in a cage. Even if the cage is really fancy — and even if the boss treats you well — it still feels like a cage. It still feels like confinement. At least it does to me.
One day, I’ll be self-employed again. I don’t know when. I’m not sure exactly how I’ll structure what I’m doing. I’m not even entirely sure what I’ll be doing.
Some people are very happy working as cogs in someone else’s machine. There’s nothing wrong with that. The vast majority of people have to do that — and many of them prefer it.
But for some among us — and definitely for me — control of time and direction is ultimately far more important than the security that allegedly comes from working for others.
One day, I’ll strap on my solo rocket pack again — and I’ll fly right out of my gilded cage for good.

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