Try Not To Regret Anything Before You’re 40…

Dan Duffy
5 min readApr 15, 2020
Some day, with a few more wrinkles and a lot more gray hairs, this will be me. Maybe.

Lately, I’ve been thanking God every day for my dog, Summer. She forces me to actually leave my house to take her for a walk, necessitating a change of scenery I never knew I desperately needed when I used to take it for granted. These daily walks not only reset my sanity, but they also reaffirm that I’m not guest-starring in Fox’s Last Man On Earth.

Most of the people I see are those I recognize from the neighborhood, usually resulting in a pleasant “hello.” But once and again, I run into a legit-friend with whom I reconnect with… six feet apart… as I did this past Saturday.

As we talked about our new normal, I could sense that self-quarantine was really getting to him. Hoping to brighten his mood, I asked how his kiddos were doing… which actually made things worse. His son is in school studying audiology, and was supposed to graduate in May. But in a twist of unforeseen bad timing…

“He took a year off school to work, which means that he was originally supposed to graduate last year. He said, ‘Dad, I won’t get to graduate. I really regret taking that year off.’ No 26 year old kid should have regrets.”

Those words really struck me. At first, I internally disagreed with him vehemently. There were things I did in life that I regretted from the time I was just shy of in utero. In fact, I have a series of regrets that start back to when I was twelve that snowballed into a life of self-disappointment for a good nine years… each step a larger regret than the last.

But as I ruminated on it a bit, I realized that my friend was absolutely right: no 26 year old kid should have regrets. Where I think we differ is that I think a regret needs to play out to completion before it should actually be considered a legitimate life-long regret.

Like that tattoo you got on a dare. Who’s Ruby?

I’ve always thought that life boiled down to ten or so moments when you hit a fork, and the path you take determines the next set of dominoes waiting to be knocked down, like Choose Your Own Adventure. When I was twelve, I attended a pre-politically correct school where you were placed into levels, or blocks. Block five was the highest-ranked scholastically, followed by seven, six, and then eight. At the start of my seventh-grade year, I was placed in block five, where I was expected to get mostly A’s, and nothing lower than a B. I was even asked to be in this special class for high-achievers each Monday afternoon in an effort to foster creativity and outside-the-box thinking.

Five C’s later, I was moved down to block seven at the end of the first quarter. I was angry with myself, primarily because the work wasn’t extraordinarily hard; there was just more of it and I was a lazy student. I begged and pleaded for another chance, and I was told that if I brought my grades up to the standard of block 5, I would be moved back up before the end of the year.

So for the better part of second and third quarter, I worked like a demon. Not only was I doing all of the block 7 courses, but I was also doing the harder block 5 math book, as well. Plus I was taking Spanish after school on Wednesdays. And I was still doing the gifted class on Monday afternoons… much to the chagrin of a couple of the students who said, “You really shouldn’t be in here if you’re block 7.”

‘I’ll show them I belong,’ I kept telling myself.

At the end of the 3rd quarter, I had brought every single grade but one up to an A or A+, and the lone B+ was two points shy of an A. I went to my teachers and said, “Okay, you said I’d be moved back up if I got my grades up.”

And then the unthinkable happened: “Well,” said one of them, “the fourth quarter starts next week, and you’ve spent most of your time in block 7 this year, anyway. Let’s just leave things where they are, and you’ll be up in block 1 next year.”

And at that moment… in my heart… I quit school.

I was so down and so resentful that by the end of the year, I’m surprised my grades hadn’t brought me back to 4th grade. And it set off a series of choices that impacted my life going forward.

  • That next year we moved to a new part of town with a new school, and being a blue collar kid in a white collar school did absolutely nothing for my self-esteem or 8th grade GPA. I phoned it in from the word go and earned the worst grades of my life. I missed my old friends and my old house, and for over a year, I just kept saying, “I want to go home.”
  • From the bad habits that I’d cultivated, I was a lousy high school student. I mean, I have no idea how I wasn’t kicked out. I was on academic probation from half-way through freshman year until I graduated.
  • There was not an institution of higher education for which I was qualified, so I didn’t even bother applying.

That’s a lifetime’s worth of regret in the space of less than six years. Had I just buckled down and said, “You’re right. Changing my block doesn’t make sense…”

… but that’s something I’ll never get to ask. And on the surface, it looks like a big-time regret that I should have held close. However, had I not gone my non-traditional route…

  • I probably never would have worked in radio… which is still the subject of my most recurring dreams ever. I haven’t worked in my original chosen profession since 2003, and I still miss it.
  • I would not have left radio to pursue a film school degree in Vancouver.
  • I would probably have migrated away from St. Louis had I gone to a standard university, probably the east coast.
  • I would never have met Stephanie. I would never have met our children.
  • I might not have discovered that I had testicular cancer until it was too late.
  • I’m probably not writing this.

So while, on paper, me giving up on school should be a regret, it led me to exactly where I am… and that’s exactly where I need, want, and am thankful to be. And while I’m disappointed that I never got my four-year piece of paper on the wall from… anywhere… I also know that it’s not what defines me, nor is it any kind of key my happiness.

And you never know what the future holds.

Age does not give you wisdom, because a lot of older people do a lot of stupid things, but it does give you perspective. So while my friend’s kid is regretful at 26, it’s not the end of the story; it’s just the end of the beginning of the story.

Give it time, kid. Give it time.



Dan Duffy

Hi, I’m Dan. I’m a husband, dad, cancer survivor, video producer, author, accidental activist, and fan of all things lovely.