Several years ago, I was talking with one of my colleagues about a project he was thinking about taking on. We were both solidly in the middle of our careers, but his evaluation of the possible project surprised me. He said, "There are a limited number of things that I'll be able to say I've done in my career, and I'm just not convinced that this should be one of them."
What struck me about this conversation is that it took a backward-looking perspective. That is, my colleague projected himself to the end of his career and looked backward over his contribution.
By contrast, most of us tend to be forward-looking. We make decisions based on how we think that particular decision might influence the next stage. This strategy can be seen clearly in politics, where politicians often make decisions based on what will help them get re-elected.
Research on regret has made a similar distinction. Psychologist Tom Gilovich and his colleagues have compared the regrets of college students to those of people in their 70s and 80s. College students asked about what they regret almost always talk about actions they took that did not go well: asking someone out and getting turned down, getting drunk, or failing a test. In contrast, older people generally regret actions that they did not take: not learning to dance, not asking out an attractive person, not taking advantage of an opportunity, etc. The backward-looking perspective highlights missed opportunities and things left unsaid.
Throughout your career, there will be many potentially pivotal moments — times when you make decisions that might shape the next several years of your life. In these moments, there is a tendency to be risk-averse. People shy away from opportunities that might go wrong for fear that they will regret failing.
A second line of research, though, suggests that you should not be too afraid of failure. Psychologist Dan Gilbert and his colleagues have done work exploring how people's lives are affected by negative events. For example, he asked a number of assistant professors who were being evaluated for tenure how they would feel six months after the decision. Unsurprisingly, people predicted that they would be happier if they got tenure than if they did not.
The surprising part comes from a follow-up survey six months after the tenure decision. Professors didn't report feeling any happier if they had received tenure than if they had been denied tenure. That is, the many other facets of their lives that influence happiness (family, friends, health, etc.) had such a strong influence on their overall life satisfaction, that even what appeared to be a devastating blow to their careers did not have a huge effect on their life satisfaction.
The outcome of this experiment suggests that it is worthwhile to take a backward perspective on key career decisions. The specter of failure looms large when there is potential risk in a particular course of action. When looking forward, the risk of failure seems important. But even significant failures are unlikely to derail your career, and what seems like a catastrophe may have little impact on your overall life satisfaction.
Instead, base your career decisions (at least in part) on what hope to say when you look back on your life. You may not always succeed, but are unlikely to look back with regret on those decisions that gave you the opportunity to reach your aspirations. And statistically you are much more likely to look back with regret on the roads not taken.
John Lennon famously wrote, "Life is what happens while you're busy making other plans." It is easy to get caught up in small projects and the day-to-day minutia of business. At least once a year, though, it is important to take stock of how you are progressing on your larger goals. If you find that you have not accomplished anything in the past year that you will look back on with pride, think about what you can do in the coming year to get you a step closer to doing what you want to have done.
Finally, encourage your colleagues to take the same approach. Every company has lofty goals. An organization that consistently looks back on the present from the desired future has an excellent chance of achieving those goals.
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