Principal’s Eye View

Ira Pernick
3 min readMar 4, 2022

I’ve been thinking a lot about regret these past few weeks. I stumbled on a book by author Dan Pink called The Power of Regret and have been absorbing its message about a topic so many of us would rather never discuss.

First, according to Pink, we all have regrets. Even those who claim to have none or those who use the phrase “no regrets” have regrets. Just the knowledge that we are not alone when it comes to regrets makes me feel a little better. Now that I am in the process of transitioning to my new role in the district I can’t help but think about the things I regret. Some of those regrets are connected to interactions that I wish went better or projects I couldn’t quite get off the ground. I know I missed opportunities here and there and I would give a lot to have a do over when I know I wasn’t at my best. Pink posits that we can use those regrets as opportunities for growth, to learn and improve. We can use our regrets as the start of our own redemption stories as we continue our never ending pursuit of perfection.

Second, and likely more importantly, is the role we can play in the formation of regret in our own children. Many of us received advice when we were young about choices we should or shouldn’t make from parents, family members or trusted educators. Sometimes that advice, a course that might be too difficult or a college that may be out of reach, caused us not to try at all. So many stories in the book reveal that not trying has a longer, more deleterious impact on us than trying and failing does. I know that’s true for me. Other stories are about professional decisions encouraged by parents concerned about money instead of happiness that led to people miserable in their careers. I don’t think any of this happens with malice, everyone who has given me advice has done so with my best interests in mind.

Still, there is a way for us to protect our children while not stifling their dreams or becoming the source of their own regret. I think of this as the “and/but” proposition. Often when our children come to us with a goal we greet it with “but” in the sentence. But is a stop sign and almost always comes with disagreement. If we substitute “and” for “but” we can create a much different sentence filled with potential. I think “and” is a yield sign…proceed with caution. I may not think my daughter’s plan for college is realistic and that her top choice is a stretch. I don’t want to “but” her, I want to “and” her. Applying to that dream school is a good idea and may change the way she works. I don’t want to stop her I want to help her add other schools around it. I know this is simplistic. According to Pink we all have regrets he categorizes as boldness regrets, times we didn’t push ourselves regardless of the reason. Often the reason to avoid being bold was connected to someone’s advice we respect.

My decision to pursue this next opportunity in my career is all about boldness. I wasn’t bold as a child, a teen, a college student. My boldness came from gaining confidence and not liking what I saw in myself when I looked in the mirror. I’ve chosen boldness ever since knowing I don’t want to regret not taking the chance ever again.

I will work to keep writing my blog, although I will have to change the name. I’ll create a plan for how to push it out as well because I do like writing it and I suspect, in my new role I will be seeing many things that excite me that are so worth sharing. Thanks for reading.

Talk soon.

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