Release From the Prison of Regrets! (Part Two)

Chris W.

Apparently my last one, “The Lifelong Regret,” touched (torched?) a few raw nerves. Proof positives are the many lengthy phone conversations on the topic of “regret” that made me cringe at the thought of the size of my next phone bill.  

You see, some conversations were longer than I anticipated since I’m not skillful at effectively hinting, “hey, gotta go.” And others were of the brief “sorry but I don’t want to talk about that stuff” category. 

Now the common thread in all those recollections were the immediacy of the responses to my query and the length of time transpired that caused those regrets; a few more than five decades ago. 

Although many I talked to have yet to come to terms with a particularly painful regret, my sense was that it was cathartic for them to share theirs once I opened up by sharing a few of mine. 

Let’s first center up on a simple definition. Aleks Krotoski defines a regret as “that sinking, nagging feeling we get when we realize we have made the wrong choice, or when things have not gone the way we hoped or imagined they would.”

With that definition sinking in with you readers, check out a few regrets that surfaced during my recent conversations:

“Because of school integration, my biggest regret in life was not being able to fulfill my dream of graduating from and playing on the basketball team at the predominately African-American Julius P. Rosenwald High School that closed down.”    – Chris W.

“My biggest regret is that I married way too early to the wrong man although I had two great children from that marriage.”  – Pat S.

“Shamefully, I caved into peer pressure, joined a fraternity in college and engaged in acts of hazing and other things I’m ashamed of today.”  –Floyd L.

“I now regret that I did not speak up when I was the target of a sexist comment during a homeowner’s meeting of which I was the chair.” –Shirley A. 

“I regret that getting a girl pregnant in high school and never married her or developed a relationship with our son from that union. He still refuses to have anything to do with me. “-John P.

Back to Chris W. above, a talented yet complicated and sometimes misunderstood history buff who I’ve dubbed “the compelling storyteller” (or “griot” as attorney “Ms. Jackson” affectionally describes him.) 

Near the end of our hour-long conversation, I shared my worry about opening a keg of worms filled with decades of folks’ nagging regrets. But in mid-sentence he stopped me dead in my tracks with this:

“C’mon bro, there’s something powerful in asking about real examples of personal regrets. I say that because there’s a good chance that others will relate to some of them at some level and others may be much more circumspect about decisions they’re about to make, not wanting to make a similar mistake.”

Thanks Chris. I needed that reality check, that kick in the rear end!

Krotoski cautions that regret can keep us looking back rather than moving forward. If you find yourself overwhelmed by regrets, Krotoski says, then the approaches below might help:

• Accept that making mistakes is part of life – none of us are perfect! Humans are fallible and some regret is inevitable.

• See a bad decision as an opportunity to learn. Focus on the things you can control, not the things you can’t.

• Avoid self-shaming. Rather than thinking, “I shouldn’t have done that”, say to yourself, “I’ll learn from this and do better next time.”

• Share your regrets to help others. Telling others about your regrets will help them too if they are faced with similar decisions.

• Focus on the good decisions you made and the things you did well. There are always things that you did right.

• If your regrets are about how your actions affected other people, then apologize. Take positive action to right the wrongs.

I liken how we respond to regrets to how batters sometimes respond to “blowback pitches” – in baseball parlance when they fall to the ground to avoid getting hit by a fastball, then get up and hit a game winning homerun.

You see, Chris responded to his “blowback pitch” by getting up and salving his regret with positive actions by moving from letdown to triumph. 

First, he arranged for the showing of an eye-opening Rosenwald documentary in a downtown theater in 2018 that was completely sold out. And second, he was asked to chair the Rosenwald High School 2022 reunion which resulted in the biggest turnout ever.

Since then, after putting the final nail in his regret coffin, Chris continued as an expert in and storyteller about African American history in his part of the state, and beyond.

So please don’t regret not sharing this piece with someone dear to you because doing so may turn out to be a game (or trajectory) changer you never anticipated.

Just saying….and not regretting!© Terry Howard is an award-winning writer and storyteller. He is also a contributing writer with the Chattanooga News Chronicle, The American Diversity Report, The Douglas County Sentinel,, co-founder of the “26 Tiny Paint Brushes” writers’ guild, recipient of the 2019 Dr. Martin Luther King, Jr. Leadership Award and 3rd place winner of the 2022 Georgia Press Award.