We will likely regret the things we did not try. (JOHN IZZO)

We will likely regret the things we did not try. (JOHN IZZO)

To leave no regrets we must live with courage, moving toward what we want rather than away from what we fear. To leave no regrets we must overcome the inevitable disappointments that life hands us.

Knowing that we will likely regret the things we did not try can have a significant effect on how we make decisions. Failure, it appears, is not the regret that haunts most people; it is the choice not to risk failure at all. In fact, many of those I interviewed told me that what we call “mistakes” often turn out to be the moments of greatest learning.

One way to frame this idea is that we can never guarantee success in our lives, since every attempt at anything holds within it the possibility of failure. If we love, there is always the risk of rejection. If we follow a dream, there is always the possibility of falling short. We cannot guarantee success, but we can guarantee failure merely by choosing not to try at all. Choosing to take a risk, however small, can have far-reaching implications in the course of a human life.

Donald was 84 years old when I interviewed him. A psychologist by training, he looked back on a rich, meaningful life. He had few regrets. One of the greatest sources of happiness in his life had been his 56-year marriage to his wife, who had died six years before our interview. When I asked him about “cross-roads” moments in his life, he immediately took me back 62 years to a college dance.

“I was a shy young man, very shy, especially when it came to talking to the ladies. In my freshman year at a college dance I saw a beautiful young woman across the room. She was wearing a cream sweater, her hair was soft, and she had a wonderful smile. The moment I laid eyes on her I knew she was the one. This was the woman I was going to marry.”

As young Donald looked across that room, he knew she was a popular girl, surrounded by other popular girls, and he knew that popular girls would hardly talk to the shy guys, let alone give them a dance. He knew he risked ridicule and embarrassment if he went up to her and she rejected his offer to dance.

“Taking a big gulp, I walked right over and told her she was the woman I was going to marry. This came as news to her and she wasn’t terribly impressed but danced with me anyway. One dance turned to two and then three. Over the next few weeks I had to pursue her quite a bit before she realized this dance would last a lifetime.”

Such a small decision, made in his early twenties—the decision to risk failure reaching out for what he wanted—turned out to be one of the most important decisions of Don’s entire life. The marriage defined his life in many ways, and even six years after her death he told me “there is not one day that I don’t feel her presence around me.”

Yet I kept wondering what would have happened if the fear of embarrassment had won out that day; if he had sealed his failure by taking no action? At the age of 84, would he look back and regret not having walked across the room and tried?

Of course, not every small act of courage winds up defining our lives or being a major crossroad in our search for happiness. But since we cannot know in advance the risks that matter, we must always move toward what we want rather than away from what we fear.

Perhaps we must make a basic choice as to whether we will live in fear or focus on what we want. Each time we play it safe, we move farther away from our truest self. Each time we choose not to move in the direction of what we want, we plant the seeds of future regret.







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