You only get one life, so why not take some chances now and again. Quitting a great job in the middle of the worst economy since the Great Depression  might not seem like the best decision at first, but if history is any indicator its a great idea.  I did this once before, in 1998.  I was working for a good company, as the Executive Vice President and my career was going really well but I was restless. I suppose I suffer from a permanent case of wanderlust.  If I look back on my life, not only don’t I regret what I did, but it was probably the single best decision I’ve ever made.  Sure there are some things I would have done differently, but if I had it to do all over again knowing everything I know now would I?  You bet I would! 

When I left on that first trip I thought I’d be gone for probably 6-8 weeks, then come back to New York to sort out a long term plan.  What actually happened was I never came back from the initial departure and I asked my dad to sell my apartment while I was abroad. I wound up staying away for four glorious years!  If I had one “do over”  I would have kept the apartment and rented it out.  I look at it this way though, how many people get to travel for four years in their late thirties, and then come back to NYC to have a great second act.  So I guess the universe required a sacrifice for the privilege of that adventure and virgins just aren’t that easy to come by in Manhattan!

Here I am again, some thirteen years after I left the first time and I find myself on the verge of committing voluntary career suicide for a second time.  I love my job, have the best boss in the entire world and I mean, the entire world, I’m good at what I do and I work for a company that pays me well and appreciates my efforts, so why the somewhat untimely exit?  The answer is because it feels like the right thing to do.  It may not make much sense but that’s why I trust it. 

I”m currently in the planning phase but hopefully in 10 short weeks I’ll move into the execution phase.  The world is different than it was when I did this the last time, smaller in so many ways, more connected.  When I traipsed across the globe last time, no one had a cell phone, or an ipad or an ipod for that matter, none of those things had been invented yet (well cell phones were around but I never thought about carrying one and I don’t remember any of my fellow travelers carrying one either. There was no Facebook, Twitter or Linkedin. , I never heard of a blog and I’m not sure they existed.  My point is that no matter how far I go, I don’t think it will feel as exotic as it did last time because things have changed so much, but an adventure is an adventure is an adventure and I can’t wait.

The other difference is, this is a road trip through the U.S. and Canada.  No airplanes, no taking  my shoes or belt off, no waiting in endless lines, just me, motels and the open road. When I want to go somewhere I’ll get in my car and go, I’ll stay as long as I like and then hit the road again when the mood strikes me. 

In case anyone is thinking  how long can I spend driving around, I’d like to draw your attention to “Exhibit A”