What happened to my career? (and other questions entrepreneurs ask themselves)

I have been helping to launch start-ups for about 15 years and every now and then someone asks "how many start-ups have you worked for". I usually say "about 5 or 6, maybe 7" I lost count, really. So now I'm in one of those moods where I want to know the real answer. How exactly did I end up steeped in the start-up life when I spent many wonderful years on the east coast with a corporate commute and a pretty badge that told the elevator I was allowed to visit the 17th floor? Major change typically happens when you're faced with a major decision. One choice is usually "safe", with a predictable outcome. The other is full of unknowns and way more likely to get you in trouble. I figure making that choice 10 or 12 times is bound to move you around a bit. Or not.

Do I stay in DC and fight with the FCC over telecommunication depreciation rates or do I pack up my truck and move to Boulder, CO where I have no job and do not know a single person? (I moved).

Do I date the MBA student or the bush pilot from Alaska? (many fond memories helping deliver beer and whipped cream to Eskimos)

Should I stay and rock climb with the band of firefighters at the campsite next to mine or leave early and make it to Kansas before Tuesday? (I climbed)

Do I drive up the coast of California in search of my dharma or make turkey burgers for dinner? (turns out they have turkey burgers in CA)

Should I have a baby or get a puppy? (a puppy can't play Risk or mow the lawn)

Do I throw the yearly bonus into my 401K or take my son to Burma and meditate in caves with Japanese monks? (we met monks)

Do I eat the quarter-sized ball of wasabi or lose the dare and the $2? (OK that wasn't me, that was my son, but he SO got that stupidity from me)

Should I stay with the company with the stable paycheck or jump ship and create something new? (I jumped)

Repeat last question (and answer) 5-6 times.

OK, I'm beginning to see the pattern. When faced with the decision to stay where life is seemingly predictable or jump into the abyss of the unknown, I tend to always take the riskier choice. One of my favorite quotes has always been "fate favors the bold", although I don't know who said it. Another favorite is from Wayne Gretzky, who is famous for saying "100% of the shots you don't take, don't go in". SO. TRUE. How will we ever know what we could have been if we don't ever try? What if the odds were so drastically skewed towards those who simply tried something new? Would it inspire you to try?

Another pattern in my career is choosing creating over maintaining. The early, creative stage of a start-up is way more fun for me. I like getting in when there are few people and no real brand name or market presence and then building it all from scratch. I've written about this stage before and it is as true for me today as it was 15 years ago, when I worked for my first start-up.

So that is what happened to my career. It feels weird even calling it a career. Its more like an addiction. A bizarre love affair with risk and possibility that continually draws me deeper into the world of start-ups. So that's how I got here - glad that mystery is solved :)