Retire? Not in a Million Years. I used to dream of living in a tropical paradise searching for the perfect Mai Tai. Not anymore...and I couldn't be happier.

By Steve Tobak

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"Wish I could talk more but, you know the drill … gotta run," I said.

"You know we all end up in the same place," said my lunch buddy. "Why are you in such a hurry to get there?"

I took that as a typical snarky remark and headed off, although my mind was already somewhere else. Sad thing is, I didn't even realize what my friend was trying to tell me. And he certainly wasn't the first.

Once, in a mad freeway dash to the airport, my wife turned to me and said, "You know, always running late like this is a sign of immaturity."

Again, I scoffed at the insinuation that there was something wrong with my behavior. But each time, it chipped away just a little bit at whatever it was that drove me to always be moving. To always be heading somewhere and never just being somewhere.

That's all ancient history, now; I've since learned more about myself than I ever wanted to know. One thing I learned is that, while we all look pretty normal on the outside, we're all sorts of weird on the inside. Our minds are like convoluted gray onions with lots of layers that go way back. Too far back, if you ask me.

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All I can say in my defense is that, before I became a more enlightened soul or a less layered onion, depending on how you look at it, I did actually think I knew where I was going and I definitely wanted to get there as fast as I could. Maybe you've heard of the place.

It's called retirement.

As far back as I can remember, I had my sights set on making enough money that I would never have to work again. Actually, it wasn't work that I was running from. It was the idea of someone else having control over my life. I was always running numbers in my head to figure out when I might get to that elusive Holy Grail.

I had all sorts of dreams of how I would live in retirement. I think my favorite fantasy was running a beachfront bar in a tropical paradise, spending every lazy day in search of nothing more than the perfect Mai Tai.

Yup, that's what drove me -- the idea of a utopian existence with no responsibilities, no worries and definitely no bosses. I was so completely and totally consumed by that vision that I was going to do whatever it took to get there. The ends would justify the means. At least that's what I thought.

As for all the relationships, the years of living, and the sanity I had to sacrifice in the process – that actually never occurred to me.

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Eventually, I reached the top of the corporate ladder and had most of my money invested in the stock market when something terrible happened. The dot-com bubble burst. And when the market began to show signs of life, I foolishly doubled down – not once, but twice – on what turned out to be insidious dead-cat bounces.

When the dust settled, there wasn't much left of my portfolio or the stock options I'd accumulated over years as an executive. To say I was distraught is putting it lightly. Truth is, when the tech bubble burst, all my hopes and dreams burst with it.

That's when somebody told me the story of Sisyphus, a figure in Greek mythology who was compelled to push an immense boulder up a hill, only to watch it roll right back down, over and over. I saw myself in Sisyphus. I finally understood what my friend, my wife, and everyone else had been trying to tell me for so long.

And I realized how many years I'd lost pushing that rock, years that I could have spent and should have spent living.

That's what did it. That's when I decided to let go. Retirement? Forget it. So what if I had to work my entire life? How bad could it be if I worked to live instead of lived to work, as the saying goes? I was finally free of that cursed boulder. I felt impossibly light. I felt incredibly strong. I felt more alive than I'd ever felt before.

Over the next few years, all good things came to me. Don't get me wrong. I never stopped working hard. But I did it with balance and perspective I never had before.

While I did eventually quit the corporate life and start my own consulting business, I've abolished the word "retirement" from my vocabulary. My motto now is, "I'll quit working when they pry this MacBook out of my cold, dead hands." You see, I know I'm not going anywhere. I'm already here. And I've never been happier.

Truth is, there is no Holy Grail called retirement, at least not the way I used to think of it. There is no utopia where you have no responsibilities, no worries, and no bosses. There is only the here and now, those you care about, and those who care about you. And every day, you get to choose how you want to live. That's all there is to it.

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Steve Tobak

Author of Real Leaders Don't Follow

Steve Tobak is a management consultant, columnist, former senior executive, and author of Real Leaders Don’t Follow: Being Extraordinary in the Age of the Entrepreneur (Entrepreneur Press, October 2015). Tobak runs Silicon Valley-based Invisor Consulting and blogs at, where you can contact him and learn more.

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