First, I've never met anyone who regretted going self-employed.

I know quite a few. As a full time entrepreneur since 2000, I used to think anyone could do it, if I could. I don't think that anymore. It just isn't a happy lifestyle for some people, most people if I'm honest.

I've known many folks in my industry who went out on their own, only to seek the comfort of working for someone else in a year or so.

Yesterday I spoke to a colleague, my age minus a couple of years, who I've known forever in the industry. He is trying to figure out his next career move. It was clear that entrepreneurship just wasn't in the cards for him, even though we possess almost identical skills, name recognition, and background.

He said, regarding the company I started 5 years ago, a subscription based community/publishing/event business, "You know, what you've done is really quite brilliant. When you started I really didn't know how it was going to work, but then you added the newsletter advertising stream, then the web banners and now the confererence really brilliant the way you built it out."

And I had to tell him that there was no grand plan. That I didn't know how it was going to work either but I just tried this thing and that thing and saw what stuck. And while he remembers the success I've had, he's forgotten all the things that I announced I was going to do during the last 5 years that didn't pan out for one reason or another.

He remembers the successes, forgets the failures.

But that kind of uncertainty, that kind of constant iteration, the risk, the creativity required, the sacrifices especially in your persona life required....well, it is not for everyone.

You and I couldn't live any other way. But we are a bit crazy if truth be told.