The Superintendent of Schools had summoned him to the district offices as soon as the bell rang, ending another day of higher learning. He’d been called there before in other districts where he had worked, often to discuss the most recent controversy he had entangled himself in. While he had a reputation as a good classroom teacher, he wasn’t much for following the latest directives from the new, trendy curriculum administrators. “You ready for me to help you get out of this mess you put yourself in?” He was taken off guard and, in that moment, felt most vulnerable. “Your probationary five-year teaching certificate for earning your mandatory master’s degree has expired. Officially, you’ve been teaching here for two years without the proper accreditation.” The young man squirmed in his chair, knowing the gig was up and it was past decision time. He was confident, however, that the Superintendent was his ally. “You’re an excellent teacher, but a better coach. I’m proposing you leave your current coaching position in the other district and come here as our head basketball coach. I’ll get you out of the classroom; your main responsibility will be to win basketball games. As for this master’s degree business, I’ll help you with a plan at the college to get the necessary credits over the next couple of years. I’ve heard through the grapevine that where you’re coaching now will not be renewing your contract next year, so this is the perfect escape hatch.”
There it was—one of the most important decisions of his life staring directly at him. These are the moments that can turn everything around, one way or the other. “Should I stay or should I go?” If he wanted to stay in his chosen career, here was the chance: make a change, compromise, settle into the cushy life of education and an easy retirement. Or take the ball, walk out the door, and see where destiny would lead.
Destiny hunts us, but we can control our destiny. There are times in our life when we must make decisions that will have large ramifications on the rest of our journey. “Regrets, I’ve had a few,” as Mr. Sinatra would say. “I should have stayed in education. I really am a teacher. I need to make a lot of money. I want to be rich and famous. I just want to be happy.” Sometimes we walk away without even knowing what we are looking for on the other side. We ask ourselves, “What could have been? What should have been? What might have been?” Nobody wins when we start wandering down “could-have-been” lane.
We have so many choices in this life. We make them, and then new questions and concerns immediately arrive. In the end, we know this life is no dress rehearsal. You get one shot. If you’re lucky, you’ll get many years to either thrive or continue searching. Some will say they have no regrets, no matter their circumstances, that regrets are a waste of time. But those are the souls that rarely change or evolve, because regret can be a powerful catalyst for growth. If we are honest with ourselves, it’s doubtful anyone wouldn’t want to go back and do some things differently.
Nobody wants to come to a point where their plan needs to be blown up. Yet, we move on, thinking we can go back and correct whatever outcomes we’ve become disgruntled with—until a day comes when we run out of time and options. Do you regret your career choices? Did you miss your true calling? Thirty-five years later, the young man wasn’t so young. He appreciated the offer that had been put before him back then. But he didn’t know at the time that when he walked out of that door with a, “Give me a week to think on it,” he would never step foot in a classroom or basketball court again. This is what was meant to be?
During these formative years when we are also contemplating a romantic partner, we have to figure out what is it we want out of love. For those determined to only do marriage once this can be an area of regret. He was only 25, already a tenured schoolteacher and varsity basketball coach. He had come all the way home to the place he’d swore to never return. The balls were being cleared and the players were headed for the showers. The young coach was working on posts moves with one of the big men when she came through the gym doors. He recognized her right away, the same girl he had seen pass by a few years back. Happenstance , or fate had put the young lady’s brother on the new coach’s team. “Hey, it’s been a longtime, how’ve you’ve been?” , the coach said with his chest stuck out proudly behind his whistle. “I’m good, I’m home for Christmas break and came to pick up my brother,” the senior co-ed said to her brother’s coach. The neophyte golden boy had so far not been very good in the girlfriend category. In his mind he had some subtle regrets as to the way things worked out with a couple of co-eds back in the day. He was firmly entrenched in the “I am forever a bachelor world. “My life is pretty filled these days, but I’d love to find time catch-up. How’s Friday night? The same girl that had rejected him in the past was now on a mission to discover what had become of the returning conquering hero. “Yeah, that sounds good, I’ll see you Friday.” Four years later, that once-rising star would walk away from everything related to teaching. At the time he believed that destiny would take care of it all. In his wildest imagination he could not have imagined that he would walk out the classroom forever and down the aisle to a 35-year-old marriage. He had let go, or been let go by so many good catches from the past. It turned out his destiny was with a girl from the place they were both spawned.
The thing to remember is that sometimes our regret in the moment turns out to be the opportunity we had been looking for the whole time. When Napoleon was pouting on the island of Elba after meeting his destiny at the Battle of Waterloo, he surely had to ponder regret. The National Democratic Party must have deep regret over their investment in Kamala Harris. The New York Football Giants can’t help but question their fatal decision to ship Saquon Barkley to Philadelphia, choosing instead to spend their money on a franchise quarterback. In hindsight, there is always room for doubt when the results come in. Of course, dwelling on the wrong turns taken at the fork in the road long ago is left for the miserable, non-evolving persons among us. There is little doubt that if Napoleon, the Democrats, or the Giants’ leadership could turn back time, they would. But we all know there is no reversing the clocks of time; there is only making the best of what already is.
The funny thing is we can’t change history, but boy, can we learn from it. “I should have, would have” is the jargon of losers. If you are one who believes in the hands of fate, it is easy to sit back and simply react to the cards the machine keeps dealing you. Or, you can throw your current hand in and patiently wait for the next deal. The latter often seems to be a surrender to your present situation, even if there isn’t an alternative plan immediately at hand. We can look through the years and dwell on what could have been, what might have happened, if only…
As life progresses, we set out on an ambitious path of collection: houses, partners, money, reputation, and position. Then come the days we start losing things: youth, innocence, friends, loved ones, and—in the lowest of times—our self-worth. It is questioned by the imaginary voices that come from our own doubts. The word regret, according to Webster or Google, means feeling sad or disappointed over something that has happened or been done. So, regret is a very personal thing. It has less to do with destiny and more with the solo pain you feel over the roads you opted to take—or not take. By this definition, regret is a place that can only be recognized by those who have made it far enough up the mountain to see where they’ve been.
At some point, we all stand on our own mountains. We look around at the view, and we can’t help but look up. We see there is still so far to go. We think about whether this is as high as we are going to get. In our quiet moments, we stand still and look down. We are startled at how far we have come. We are also filled with that voice inside our head that keeps pushing us to catch up. This is the place where we contemplate regret. Most of us say we have no regret, that every decision we made was our best effort at the time and that it makes no sense to dwell on what can’t be changed. Some face a few bumps in the road and let regret take over. It is hard not to feel sorry for ourselves and act the part of the victim.
Sometimes, we just need to look back, and we will realize that all regret and disappointment are just opportunities in disguise.
Thirty-five years have passed since the day the young man walked out of his boss’s office with the decision of a lifetime hanging over his head. “Wow, now what?” he remembered saying sheepishly to himself as he walked out the door. It was the last day of the school year in 1989, and decision day had arrived. “This isn’t easy for me, boss, so I’ll say it fast. I’m resigning my teaching position and am going to try to weather the storm with my coaching job in the other district.” Without knowing it, this was the turning point in his destiny. He had been dealt a great hand and played it way too loosely. He was 100% responsible for the position he found himself in.
This was the opportunity to change direction. Who could tell if there would ever be another? At the age of 30, the picture was bleak for a young man who would soon be without a classroom or basketball court to showcase his talents. He was aware he was playing chicken with his life’s legacy. It is possible to become numb to our situation, so we keep moving forward, relying on a brave confidence that comes from pure terror. While it may be painful to look back, it doesn’t have to be.
This New Year’s, the resolution is to get a perspective on regret and disappointment. Do what you have to do to find opportunity in the obstacles that confront you. If you were given the chance to start over a thousand miles away. Do you think you could find yourself? Resolve to turn all regrets into opportunities.
