Why You Should Dump Your 5-Year Career Plan

I feel incredibly fortunate to be in the position that I'm in — running Expedia, Inc. — at a relatively young age (although I have to say that I'm feeling a bit older recently). These days, young CEOs running technology companies are nothing new, but I'm different from many of these young CEOs in that I'm not the founder of Expedia, Inc. — that title goes to Rich Barton who has continued on to found a number of amazing companies, including Zillow and Glassdoor. I'm what you'd call 'professional management.'

Though I wasn’t part of Expedia’s founding team, I was lucky enough to be in the right place at the right time to take over as CEO of Expedia, Inc. and build on the foundation set by the founders of 'revolutionizing travel through the power of technology.'

The secret to being at the right place at the right time is of course great career planning – carefully understanding your strengths and weaknesses, working on those weaknesses, picking the right career path and moving up the right ladder, and picking up the right skill sets. Right? Well, not really, at least based on my experience.

A number of our young employees ask me about planning their careers, and for them I always have two pieces of advice:

Tip #1: Don’t plan your career.

What do I mean by don’t plan your career? You wouldn’t believe the number of people I've seen make bad decisions about their careers based on preconceived notions of where they want to be in five or 10 years. They feel like they have to make a certain amount of money, have a certain title, be promoted every three years, or move on. Yet what I've seen, both in terms of general business and individual career planning, is that in a world that is ever-changing with uncertainty just around the corner, long-term career planning is effectively extinct.

I'd be an absolute genius if I could predict exactly what Expedia, Inc. would look like five years from now. While I have one eye toward the future, I spend a majority of my time planning how we can be incredibly agile and smart about finding the right opportunities today and pouncing on them faster than our competition. I have no idea what feature set our air or hotel team will be building six months from now, and I consider that a good thing. Whatever they do, they'll do it fast.

My career planning advice is similar: optimize for the next one to two years instead of the next five or 10. Look for the right opportunities, stay flexible, have some idea of what direction you are headed in, but don’t lock into a long-term direction because chances are that the world will change up on you.

Tip #2: Work for the right person.

The one constant I've found in an ever-changing world is that great, smart people stay great and smart. So my second piece of career planning advice is to find the smartest and most competent person around you and work for that person. It doesn’t matter if the move is lateral, down or up. Just get yourself working for that great person. Don’t ask for much; just work your ass off.

The benefit is two-fold. First, you'll learn a lot. You'll be challenged. You'll grow as a person and as a professional. Second, smart people tend to get promoted. When they get promoted, you'll tend to follow them as they rise in the ranks (assuming you've done a great job). You'll essentially have your career planning taken care of until you find another amazing interest or great person that you can learn from. You won't know exactly where you are headed, but chances are, at some point — and hopefully at more than one point — you'll find yourself at the right place at the right time, and you'll do better than fine.

Photo: Warren Mell Images