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Is There a Positive Side to Regrets?  Or Shoulda, Coulda, Woulda


Co-Author of Conflict  The Unexpected Gift

“Back when I was offered a job, a dozen years ago, I should have taken it. Then I could have grown in my profession and by now I would be doing great. Instead I’m in this dead-end, low paying job, for which I get no respect.” 

“I accepted the first marriage proposal I got just because I was already 32 and felt hopeless about ever getting one. Looking back, it was a huge mistake on my part. I wish I had listened to that nagging voice in my head, telling me I could do better. If I had I wouldn’t have ended up with a horrible divorce that led to my complete lack of self-esteem.”

How often have we heard stories similar to these, or even experienced ones like them in different settings ourselves?  They reflect what I call the “Shoulda, Coulda, Woulda” syndrome. People often berate themselves for what they consider to have been mistakes they made, which led to what they see as their current unfortunate situation.  

Instead of bemoaning the mistakes we’ve made in the past and living with regrets, what are ways we can look at, deal with and resolve issues that have arisen from them? In the Bible, Peter, the apostle, three times denied his association with Jesus, which he came to regret tremendously. (See Luke 22:54-62) However, he later came to acknowledge Jesus’ teachings and healings to such an extent that he himself became a teacher and a healer. Rather than wallowing in his past mistake, he grew from it. Have any of us done that?

I know a mother who sometimes didn’t listen well to her young children. It made for unpleasant confrontations and angry words between them and her. She could have let it go at that, with the thought, “that’s the way it is between parents and kids” and shrugged it off. However, that didn’t make for a harmonious family and her husband was also upset by her behavior. 

One day, the mother told her kids they should take umbrellas with them to school, because rain was pouring down. They responded in no uncertain terms that it wasn’t “cool” to carry umbrellas and that they’d rather get soaked than have their friends see them carrying umbrellas. Remarkably, she decided for the first time to try something different that was outside her comfort zone. Instead of trying to talk them out of their “foolish behavior,” she decided to listen to what they were saying. The more she listened the better able she was to hear the fear in their voices of being shunned by their peers and to understand their plight as they saw it. As a result, she was able to hug each one and say as they left for school, “I hope you don’t get too wet.” She “coulda” ignored the situation, which “woulda” led to more frustration and her later realization that she “shoulda” done something different.

If we made what we consider later to have been a misstep, we don’t have to fall into the trap of self-blame. Rather, we have the choice to consider how we might view a current situation differently. If we pause, become quiet and listen to our “inner voice,” we can become aware of what is truly needed both by others and by ourselves. The key question to ask ourselves is:

What can we learn from the path we mistakenly took then, in order to take a different more progressive one now?

Let us give ourselves credit for having the insight and ability to make better choices today than we did in the past, forgive ourselves and turn regrets into positive insights and actions.