All your friends tell you they wish they had your job, and you tell them you wish you had their’s

You might be an entrepreneur if…all your friends tell you they wish they had your job, and you tell them you wish you had their’s.

I was visiting with a friend of mine a year or two ago. He had a six or near-six-figure salary, a $650K house that was half paid off, nice cars, a big plasma screen TV, his wife was able to stay home, and while he certainly worked hard, he probably wasn’t putting in the hours I have. And so imagine my surprise when he said “Man, I wish I were doing what you’re doing.”

Meanwhile, I look at my friend and think “Man, I wish I were doing what he’s doing.” But in truth, I think both of us are more or less happy with what we’re doing. If we weren’t, we’d be doing something else. While I sometimes tell people I’m trapped in my business, I’m sure if I really wanted to get out of entrepreneurship I could find a way. And if my friend really wanted to be an entrepreneur he would be.

This is a true case of “the grass is greener on the other side” wherein my friend and I saw certain aspects of the others’ situation we desired without seeing the baggage that comes along with it. When my friend said he wanted to do what I was doing he was probably thinking of the autonomy, the thrill of working for yourself, the control, and the potential for great returns. When I look at his situation I think about how great it would be to make consistently good money, to have a nice house, and be able to give my wife some relief from the stress of being an entrepreneur’s wife. I don’t think my friend was thinking about the long hours, low pay, stress of making payroll, and chance to lose everything. Nor was I thinking about working within a large bureaucracy, being a number, reporting to others, and dealing with office politics.

The more I think about it, I think the grass is greener on my side. At least for me. I think the chances that I might have what I envy about my friend’s situation without leaving entrepreneurship are greater than the chances of him getting what he wants about my situation without him leaving the large corporate world.

However, about a year after our conversation where my friend had expressed an interest in starting his own business he quit his full-time job and became an independent consultant. While that’s not exactly my definition of entrepreneurship it’s a good step in that direction and it seems to be working out well for him so far. Of course if he decides to hire on some employees and start a full-fledged firm he’ll really find out what he’s been missing and we’ll see if he changes his tune.