“I’ll retire … when they pry the computer out of my cold, dead hands.”

When I was a young up-and-comer, I thought about retirement all the time. As soon as I got a taste of the windfall returns stock options could generate, I couldn’t wait to hit it big so I could do what I wanted, when I wanted, instead of working like a dog and spending half my life on airplanes.

I had all sorts of fantasies about pristine sandy beaches, mountaintop estates, and of course, telling my jerk of a CEO to take his job and shove it.

That was about 20 years ago. Things certainly have changed since then. Actually, everything’s changed, courtesy of a confluence of factors I have to admit, I never saw coming. And if I’m not mistaken, an awful lot of you are probably in the same boat.

First, to say the economic picture for retirees has changed would be a ridiculous understatement. There was a time when I was sure I knew how much money I would need. Somehow, over the past decade or so, that became a moving target.

The economists tell us inflation’s been low for years, but somehow, the cost of everything has skyrocketed. Healthcare, energy, food, even real estate – at least where I live in Silicon Valley – is out of control.   

Retirement ain’t what it used to be, that’s for sure. And not in a good way.

Second, I may have burned out on the corporate executive lifestyle, but not on the need to have a fulfilling life. And that includes accomplishing some things on my own that I never got to do working for a company. Turns out I had some fantasies I wasn’t even aware of that could actually generate significant income.   

Entrepreneurship ain’t what it used to be, either. And I mean that in a good way.

You see, a former executive and an old friend once told me, “There are two reasons why people don’t retire and both are tragic: The first is they can’t afford to. The second is they have no other interests.”

Turns out he was wrong, dead wrong. There’s a third reason. They have lots more left to do on this planet than seeing the sights, stuffing their faces, and working on their handicap, which is what most of the retired people I know seem to spend their time doing. And they have other interests that just happen to involve working.

In a recent interview, when asked, “Would you ever give up this gig?” Jethro Tull frontman Ian Anderson said, “By and large people who do what I do prefer to die with their boots on. We'd rather go to the bitter end and be having some kind of fun doing it than retiring and playing golf and going fishing, which may be seductive to someone who's spent their entire working life sitting in an office, but obviously my job is a little bit more… invigorating, and a bit more romantic in a kind of way."

Maybe you don’t rock and roll like Anderson, and I know I’ve spent enough time at 30,000 feet to last a lifetime, but the point is valid, nevertheless. Most of us had romantic notions – things we wanted to do before we got sucked into our careers – that remain unfulfilled, undiscovered, or in my case, submerged in our subconscious.

Ten years ago I quit the corporate grind and started my own consulting firm. Then came executive coaching and, the biggest surprise, writing. Ever since I was a little boy, I’ve been a prolific reader. I wasn’t even aware that, deep down, I’d always romanticized the profession. So when the opportunity came, I jumped at it. Truth is, I’ve never been happier. 

I was recently searching for a good landscape firm and came upon a well-respected company run by a guy named Phil. Turns out, Phil is a former Wall Street attorney who moved out west to become general counsel of a public company and ended up buying a landscape company. He loves it. And he never looks back.

You know, some executives hit it big, make their money, and that’s it, they’re done. I’ve known quite a few. They don’t seem happy when I see them. It’s as if what they did for all those years was nothing more than a means to an end. And once they got their pile of gold, they bought their Ferraris, their trophy wives, their second or third homes, and faded to black.

I guess it’s never been that way for me. I’m more passionate about my life. I get a real kick out of helping other people and companies achieve success. And the connected world makes it ridiculously easy to explore opportunities, find what you never thought you were looking for, and maybe fill the gap between what you thought you would need to retire and that moving target.

As I begin the second decade of the second half of my career, all I have to say about retirement is, I’ll retire … when they pry the computer out of my cold dead hands.  

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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