How Real CEOs Build Their Own Careers


With job security a thing of the past and the notion of spending decades climbing the corporate ladder a decidedly unattractive proposition, entrepreneurship has become the career mantra of the masses. But being your own boss and owning a business, even as a solopreneur, is far from the panacea it’s been made out to be.

Lurching headfirst into the startup realm without the right expertise, skill set and network could be a huge mistake, as many are surely finding out. Slugging it out with everyone else as a blogger, content marketer, web developer or a coach of some sort is no way to achieve career nirvana.

There’s certainly nothing wrong with dreaming of becoming the next wunderkind like Mark Zuckerberg or Evan Spiegel, but the truth is, that’s not how the vast majority of today’s business leaders got where they are. Instead, they spent years grooming themselves and building their own careers before striking out on their own.

Twitter chief executive Dick Costolo worked in improvisational comedy after college. Don’t laugh, thinking on your feet and a good sense of humor are both critical leaderships skills. He then spent eight years at Andersen Consulting before co-founding his first company.

While everyone knows that Facebook acquired WhatsApp for $19 billion last year, co-founders Jan Koum and Brian Acton didn’t just waltz into the land of entrepreneurial riches. The pair cut their teeth at Yahoo for nine years before an iPhone purchase gave Koum the idea for an ad-free, game-free and gimmick-free mobile messaging app.

Doug Mack may not be a household name but he’s CEO of $1 billion sports retailer Fanatics and former boss at One Kings Lane. After getting a finance degree he spent more than a decade at GE, McKinsey and The Learning Company before spinning out Scene7 as co-founding CEO.

I can tell you story after story but the truth is, grooming your own career is nothing new. After my engineering management career sort of flat-lined, I decided to fill a gaping hole in my skill set and segued into sales and marketing. That turned out to be the ticket to executive management and eventually co-founding a management consulting firm.

If you’ve got high aspirations for your career and are pondering the entrepreneurial route or how to get to the top from here, consider this:

Nobody has it an easier than you do.

Of course that’s not entirely true. Some do but most don’t. The point is, that didn’t stop any of us from getting to where we are. I grew up with nothing and fought hard every step of the way. That’s how most do it. Besides, choosing to see it any other way will only make you bitter and angry and that’s no way to go through life.

Take off the rose-colored glasses.

On the opposite end of the spectrum I see a lot of utopian thinking going on out there. Too many of you are of the mindset that “if I think like an entrepreneur and call myself an entrepreneur, then I’m an entrepreneur.” I hear it all the time: “fake it ‘til you make it.” Unfortunately, that’s not how it works.

Moving forward in your career has far more to do with figuring out what’s really holding you back than a lack of positive thinking. If you’re not willing to be honest with yourself about the challenges you face, how in the world do you expect to overcome them?

Don’t think “entrepreneur.”

A growing problem, especially with the younger crowd, is that, in a mad rush to build their personal brands and cast themselves as entrepreneurs, they lock themselves out of potentially career-making opportunities.

Early in your career is no time to reduce your options. Once you’ve figured out what you do better than anyone, that’s when you want to focus on doing just that. Until then, keep your options open. Besides, your reputation is built on credibility. Don’t be so quick to call yourself something until you’ve achieved it.

Your career is a marathon, not a sprint.

I saw an article the other day called something like “How to become a CEO by the time you’re 30.” Granted, that’s an eyeball catching headline but still, when did a label or even a title become a goal in life? Besides, calling yourself a CEO – or an entrepreneur, for that matter – doesn’t make you one.

You’ve got to marvel at the irony. Nobody becomes a successful executive or business leader by following anyone else’s prescriptive “how to” list. They do it by thinking and acting differently and carving their own unique path. That’s what this is really all about. It’s your career, no one else’s. If you want to be a leader, then lead. Don’t follow.