Last night I had dinner with an old friend I hadn’t seen in 30 years. Yes, I know what that means. I’m old. Thanks for the reminder, Captain Obvious.

Although our career paths couldn’t be more different – she’s into art and teaching and my thing is tech and business – we’ve somehow found ourselves in exactly the same situation: Trying to make a go at what we love after long careers doing what paid the bills.

If you’re nodding your head because you or someone close to you is doing more or less the same thing, I’m not a bit surprised. More and more Baby Boomers are in various stages of developing or executing what I call a second half career strategy. An intriguing confluence of factors has led to this phenomenon. 

First, think about how your career developed. I don’t know about you, but I came from a lower middle-class family that didn’t have much. So I did what I was good at for a living and really just followed the money up the corporate ladder.

Sure, there were some hiccups and changes along the way, but they were more like branches off the same tree than moving to a whole different forest. My career moves were all about getting promotions, homing in on what I was really good at, and following market demand.

That was all well and good until my perspective on life changed. It happens when you get older and realize your mortality or some other event causes you to see your world in a different light. That’s when I realized there was something else I’d always loved but never had the chance to try my hand at. You’re reading a component of that strategy.

The second factor is the economy. The great recession has thrown a wrench into a lot of retirement plans. Interest rates are non-existent and expenses – everything from food and energy to health insurance and taxes – are rising faster than expected. And the boomerang kids are no help. Even conservative planners are finding that they don’t have enough stashed away. Nobody saw this coming.

Unfortunately, finding a job in your 50s is a little harder than it sounds, courtesy of a growing age discrimination problem. While Jesse Jackson grabs headlines over tech’s lack of diversity, nobody seems to care that the average age at Facebook (FB), Google (GOOGL), Amazon (AMZN) and Apple (AAPL) are 28, 29, 32 and 33 while the average American worker is 42.3.   

That brings us to the final factor. This is after all the age of the entrepreneur, is it not? The barriers to doing your own thing have never been lower thanks to the searchable Web, e-commerce and social media. The competition may be stiff, but that’s nothing new. It has certainly never stopped us before.

When you put it all together you get a big slice of a populous generation pursuing their dreams as small business owners searching for personal fulfillment and additional income to help pay the bills, not necessarily in that order. They call Millennials the entrepreneurial generation, but I know a lot of Boomers that would challenge that label.

A retired former CEO once told me, “There are two reasons that people don’t retire and both are tragic. The first is that they can’t afford to. The second is that they have no other interests.” As much as I respect this man, he was wrong. There is a third reason.

I have loads of interests to spend my time on, but as with many people, I’m just not cut out for the pasture. There is something wonderful about reaching for the stars I haven’t quite gotten my fill of, at least not yet. And that’s far from tragic. It’s challenging and fun. To my old friend and I, it feels like a second life. You can’t beat that.

  

Steve Tobak is a management consultant, executive coach, columnist, and former senior executive. He runs Silicon Valley-based Invisor Consulting where he advises executives and business leaders on anything and everything. Contact Tobak.

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