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What Was Your Best and Worst Career Move?

Regret is a bitter pill to swallow. That's why, in terms of your career, it's a good idea to understand opportunities missed and mistakes made in real time. They don't age well.

Unfortunately, when it comes to career moves, insight can be elusive. And the good moves can be just as perplexing as the bad ones. I'm not sure what's worse: having one success and being completely unable to duplicate it because you don't understand how or why it happened, or not facing the fact that you made a bad decision and blew it all on your own.

That why you really have to take a hard look at both the good moves and the bad for them to be of any value. To that end, here are my best and worst career moves and lessons learned. They're amusing and insightful all by themselves, but in exchange, we'd all like to read and laugh at -- I mean learn from yours. That's the deal, okay?
Best Career Move
I graduated from college in 1977 with a B.S. in physics, but there were no jobs, my grades were so-so, and I had no idea what to do next. I was dating a girl whose father just happened to be chairman of a semiconductor startup. He drove a Porsche, showed me around his very cool company, and I was hooked. So I went back to school, got a master's degree in electrical engineering, and the rest is history.

Lessons learned: I remember being really down because my career had hit a dead end even before it started. Still, I never gave up hope, probably because, for whatever reason, having a successful career was imperative to me.

So when the opportunity arose, I pursued it like a starving pit bull, which meant bugging my girlfriend's dad about how to get a job in the industry, then getting the graduate engineering school to admit me part time (they wouldn't admit me full-time until I demonstrated I could pick up my grades, which I did, bigtime), and on and on.

Lessons Learned:

  1. Set your goals and don't let anything stand in your way
  2. Pursue opportunities to the end, no matter the odds
  3. Trust your instincts - when they say go, you go and don't stop until you get there, wherever there is
Worst Career Move
In 2000, I was a senior VP with a late-stage startup company when the tech bubble began to deflate. Instead of hunkering down and sticking it out, I left to take a CEO job at an early-stage startup in need of a second round of funding. That's when the bubble really burst and we ended up shutting the doors just seven or eight months after I got there. Four years later, the company I originally left went public and, well, let's just say I left a lot of dough on the table.

Lessons learned:

  1. The Value of Stick-with-it-ness,
  2. It's way better to be the number two guy at a company with a good chance of success than the top guy at a company with little-to-no chance of success
  3. Early-stage startups suck (for me, at that stage of my career, anyway)
Okay, now it's your turn: Best and worst career moves, let's have 'em!

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