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This Is How You Solve the Stickiest Career Dilemma

Here's a hint: If you believe in yourself and are willing to take risks, nobody can tell you what you can and can't do.

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If you’re the kind of person who’s driven to succeed, you probably started your career just like I did. Hungry for knowledge and ready to take on any obstacle in my path, I charged out into the world shouting “Bring it on!” … and ran straight into a brick wall.

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That wall is called being pigeonholed.

The better you are at something and the longer you do it, the more likely that you’ll be stuffed into a neat little classification from which you will find it annoyingly difficult to escape. Some call it the competency curse, but from what I’ve seen, it happens no matter how good or bad you are at your job.

While its popular to whine about all manner of –isms these days, here’s a problem that affects everyone. I don’t care if you’re black, white, green or gender agnostic, your career is far more likely to be stunted by being branded according to your experience than your appearance.

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As a young engineer frustrated by an inability to break into the management ranks, I once sought the advice of my boss’s boss. He told me that his biggest mistake was becoming indispensable at his current position and never cultivating an understudy to take his place.

What a dilemma. If you’re lousy at your job, you never get promoted. If you’re good, you still get stuck. Talk about a Catch-22.

I soon learned that, even if you do manage to segue to a different field, you just get stuck with a different label. It’s a sticky problem that plagued me throughout my career. But there are creative ways out. Listen and learn.

It took forever, but I finally became an engineering manager, only to get trapped in the middle management abyss. Beyond frustrated, I did something you’d never think of to overcome the dilemma: I chucked it all -- 10 years of experience -- to start at the bottom as a sales engineer.

Granted, I initially took a salary hit, but with all that technical and management experience under my belt, I was able to become a top salesman practically overnight. I made lots of connections and, within two years, ended up running sales at a software startup. But after a successful IPO, the company got squashed by Microsoft.

The timing sucked. I was out on the street, pounding the pavement during a recession. Since sales leadership jobs were few and far between, I set my sights on marketing. Once again, I found myself categorized, this time as a sales guy. Still, I used my connections to land an interview with a fast-growing public company in Silicon Valley.

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As I sat across from the VP of marketing, he looked down at my resume, shook his head, and said, “I’m sorry that you came all this way, but I’m afraid you don’t meet our requirements. I’m looking for someone with at least five years of marketing experience and an MBA. You have neither qualification.”

That’s when I learned the second way to overcome being pigeonholed: I sold the guy. Maybe it was that my wife and I were almost out of savings and I was desperate. I wasn’t entirely sure where it came from, but I pulled out all the stops and, 30 minutes later, had the guy convinced that I had the capability he was looking for.

Sure enough, I went on to become a successful VP of marketing over the following years, but that wasn’t the end of this insidious curse. Having been contacted by several executive recruiters, I finally decided to throw my hat into the ring for a CEO job. That’s when I found myself sitting across from a prominent venture capitalist. Once again, he looked down at my resume, looked up at me, and asked, “How did a marketing guy end up being considered for a CEO job?”

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With 20 years of experience, including a decade as a pretty accomplished senior executive with some very well-known companies, I was still being typecast. Sheesh.

Still, I got the job.

In case it doesn’t pop right out at you, the solution to the pigeonhole dilemma is this: If you believe in yourself, are reasonably competent, are willing to take risks, can think on your feet and are good with people, nobody will ever be able to tell you what you can and can’t do.    

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