Nancy Halpern

The world is divided into two groups of people: those who love the question “where do you see yourself in five years?” and those who recoil in horror and dive under the couch whenever it’s asked.

For the five year-ers, life can be planned. These people have a destination, and they set out the markers, the milestones, and the achievements by calendar date. They know where they want to be and they know when it’s going to happen. They are seen as goal driven and clear headed, and they have already nailed the second most boring interview question ever. But they also run the risk of developing tunnel vision and therefore missing great opportunities because they don’t necessarily adhere to a particular plan.

For the couch divers, this is a ridiculous question. They’re fond of quoting that infamous guru Woody Allen: “If you want to hear God laugh, tell him about your plans.” You can have a goal, you can schedule it out and then – stuff happens. These people are seen as the adventurers, explorers, and change agents. They can be, however, victims of shiny penny syndrome – chasing down every new idea, being an inch deep and looking back without a clear sense of what exactly they achieved.

For the ambitious, it doesn’t really matter which you are. It matters that you’re hungry and that you try harder – all the time. It matters that you often feel that your best could still be better. You want more. You’ll take more. You’ll do more. And you really want to get ahead.

In my coaching practice, the first question I ask the strivers and drivers is: “how do you define success?” This is the place to start – not with a plan, necessarily, but with a sense. How will you know that you’re successful? Different people have wildly different answers and definitions. For one client, it was a dollar figure. Money bought her freedom, and she wanted lots of freedom, so she wanted lots of money.

For another, it was a title – the recognition from the outside world that she was a CEO. And yet a third believed that it was tapping her potential, working her way down the professional list to know that she had done all that she was capable of doing.

The answer to this question creates a litmus test for you to better assess what sacrifices are worth making and which are unnecessary -- and therefore avoidable. For the money driven, it means that they will sacrifice interesting work if something less glamorous will increase net worth faster.

For the woman wanting to maximize her abilities, she’ll sacrifice forward movement up a large corporate ladder to sniff out the work no one has yet done or the problems that are still to be solved because they energize her.

No matter what getting ahead means to you, there are also the personal sacrifices to consider. If you’re married, there’s a partner in the mix. How much time with them do you want to sacrifice? Will they understand? What won’t they accept?

And of course children add another layer of complexity to this equation. How much time away from them is acceptable to you? Do you see this as a sacrifice or just part of normal life? Both answers are true, either is acceptable.

If you’re single, there are still sacrifices to weigh. Will working this hard make you happy? Are you seeing your friends, spending time with family, and doing the things you love that make you a better rounded and more content human being?

Succeeding at anything means a trade off of time and patience for the hope of something yet achieved. You can’t have it all – but you can figure out what you really want and go into that thoughtfully and consciously about what you also can’t have.


Nancy Halpern is an executive coach with a proven track record in helping senior leaders and their teams reach their full potential. She's been quoted in The Financial Times, The New York Times and other publications, as well as appearing on both NPR and the PBS NewsHour.


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