Standing at the Crossroads

Career decisions can sometimes feel as random as a flip of the coin. Do you take the enticing job offer from the firm across town, or try and leverage it into a promotion at your current job? Both paths offer potential rewards — and unseen risks.

Over the course of your career, you will face dozens of agonizing career decisions. Since you only get to move through life once there is an understandable desire to try to make each career decision the “best one.”  The difficult thing is that maximizing returns on decisions like these is impossible.  There are simply too many unknowns. As a result, employing a rational approach to the decision is a fool’s errand.  In cases like these, such efforts only provide comfort to the degree you let yourself be fooled about your ability to know the unknowable risks associated with each choice.  Fortunately, we think we have an approach to offer that beats a coin flip by focusing you on your situation, as well as your strengths and weaknesses.

Decide whether to go your own way or follow the crowd

Sometimes getting ahead requires the courage to break away from the pack.  The sport of sailing exemplifies this approach. Since sailboats can’t sail directly in to the wind, boats racing to an upwind mark must work their way upwind by zigzagging—what sailors call tacking—back and forth.

In a race, several boats will be working in such a manner to be the first to reach the upwind mark.  Here is where strategy comes in to play.  At some point during this leg, the captain of one of the boats will decide it is time to tack.  Immediately, every other captain has to decide whether it is better to continue a bit farther on the current course or to tack to cover.

What drives this decision?  If the captain tacks to cover he expects to experience the same sailing conditions enjoyed by the lead boat—tide, wind, and current should be largely the same. Tacking to cover means the captain thinks the boat and crew have what it takes to out sail the other boats; taking to cover effectively holds other factors, such as weather conditions, constant.

On the other hand, by continuing on course a captain is betting the wind, tide, and current will be at least as favorable as, if not better than, those experienced by the tacking boats.  Staying on course provides an opportunity to make the most of not just the talent of the crew but hopefully unique and positive sailing conditions.

So it is clear to a sailor that tacking to cover is safe, but it does make it more difficult to create a separation from the other boats.  The strategy makes sense when you think your boat and crew are unequivocally better than the others—you should emerge as a winner with everything else held constant.  But if you are not sure your boat and crew are superior, sailing on alone may provide lift that the others won’t experience.

In our study of career decisions, we see so much tacking to cover.  It begins very early in life, but perhaps for adults the first example is deciding to go straight from high school to college, like everyone else.  Some, though, opt for a “gap year” experience that might provide them lift to create separation from the competition as they move on in their career.

As you think about how to develop and deploy a career strategy that will help you get ahead, this is the central question you must face.  For your best move, what you have to decide is simple.  When you are confident that your your résumé and talent have what it takes to outshine the competition, then taking the “safe” path make sense.  On the other hand, if you are not convinced you can win by copying the strategies of others, then tacking to cover is a bad move. In this instance, you are better off making career moves that head you in a different direction, where you can enjoy unique experiences that you can use to differentiate your résumé, and develop your talent, to win in the future.

Understand the Risks

We are quick to agree that properly understanding risk may be one of the skills that differentiate truly remarkable executives from merely successful ones. Remarkable executives are able to exploit risk to their advantage. They create wins by seeing the opportunity where others fear to tread. They know how to use opportunities to set off on their own course to tell stories that differentiate them in meaningful ways from competitors.  That is how they separate themselves from the competition.  Tacking to cover is safe—you likely won’t finish second by a larger distance than that you already trail by.  But if the conditions are right, setting your own course may ultimately be the winning strategy.

This post was co-written with Nathan Bennett, the Wahlen Professor of Management at Georgia Tech. Miles and Bennett are authors of the recent Stanford University Press title, “Your Career Game.”