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Career Choices are Hard But This Is How You Make Them Easier


Dec. 28, 2016 Entrepreneur

For some, the holidays are a time of reflection. For others, it’s a great excuse to chill out and party. I like to do a little of both. OK, maybe a little of the former and a little too much of the latter, but that’s just me.

The other day, I was driving around doing some last minute Christmas shopping when John Lennon’s “Watching the Wheels” came on. Maybe it’s the time of year or just my mood, but the lyrics really spoke to me in a way they never have before, particularly on the subject of hard career choices many of us wrestle with.

The song is a response to those who took issue with Lennon’s five-year exit from the music business to enjoy a little family time and raise his son, Sean. While there is some question about how happy he really was in that role, there’s little doubt that he willingly dropped out of “the big time,” as the song suggests.

You’d think that would be a tough move, but that very much depends on his reasons for making it. It may have been a hard choice, but if he did it for the right reasons, it was probably the right choice … for him.

I can relate. In 2003, I gave up all the power and perks of a senior executive in the high-tech industry and, instead, chose to lead a relatively quiet life as a management consultant, a columnist and most recently, a writer. I took that big step and never looked back. And the funny thing is, I don’t miss being a corporate bigshot one bit.

As explained in the preface of my first book, Real Leaders Don’t Follow, I didn’t quit the life out of any particular sense of purpose — certainly not to become an entrepreneur, change the world, or any of that nonsense — but because I was exhausted from all the crazy travel and stress. I needed a break. Apparently, a long one.  

Climbing the corporate ladder like some crazed workaholic monkey for 23 years was enough. Put a fork in me, I was done. I needed some me time. And I knew that I had to do something different with my life before I burst into a massive fireball from burning my candle at both ends for way too long.

Don’t get me wrong. Helping to run a corporation — getting a startup get off the ground or growing an established company into a market leader — is among the most fun and gratifying ways to make a living. But, exhaustion notwithstanding, my career had become routine. I needed a new challenge. So here we are.

The thing is, I couldn’t do what I do now if not for what I’d done before. Where would my insights and inspiration have come from if not from a successful career? Who would pay me for strategic advice without all that experience behind it? Who would hire me to consult, read my columns, or buy my books? Nobody, and rightly so.

More important, I wouldn’t be happy in this new role if I hadn’t first accomplished what I set out to do.

That was probably true of Lennon, as well. Of course, the man had tremendous talent, but I doubt if he would have felt fulfilled as a stay-at-home dad and writing the occasional ballad if he hadn’t first spent the previous twentysomething years setting the world on fire.

If you’re the kind of person who’s driven to make a difference, change the world, do great things, or any one of the popular memes of the entrepreneurial crowd, here’s my advice. Don’t be so grandiose. Don’t try to conquer the world all at once or plan everything out. That’s not how it works.

Just follow your interests, accomplish one thing at a time, and let your life unfold organically. If you stay true to yourself, everything will work out fine. Then someday, maybe around the holidays, you’ll hear a song, do some reflecting and realize that everything happened exactly as it should have.   

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