The Clarity of Hindsight


Ol’ Blue Eyes had a few, and I’ll wager that you do too.

While certainly not part of a traditional genealogy, writing about your regrets – whether missed opportunities or how you would do something differently – makes for a rich family history worth reading.

By their nature, regrets tend not to be pleasant memories to reminisce about around the dinner table. They can, however, serve as powerful stories to pass along warnings, encouragement, or merely understanding of a complex personality.

Now, I’m not talking about momentary regrets, as in “I shouldn’t have had that third margarita after eating the entire plate of nachos.” If we’re going to craft a narrative around regret, we need to be able to draw a larger lesson out of it, to give it the perspective that typically only comes with a few years’ hindsight.
For me, two major regrets stand out. While in college, I participated in a Study Abroad program to Costa Rica. Because I was on scholarship, the out-of-pocket costs to me were minimal. My experience proved to be wonderfully unique and one of the biggest things I had ever done up to that point. There is very little I regret about that trip. My regret is not taking advantage of another trip offered by my school.

During my time in college, the study abroad program sponsored a wildlife photography trip to Antarctica. I don’t remember which term the trip was held, but it must have been prior to my Costa Rica trip. If I had known that I could apply scholarship funds to a Study Abroad trip, I would have been on the next boat to the bottom of the world – wouldn’t you?

Antarctica Trip 2001 by John Lester CC BY 2.0

I am fortunate that my college years allowed me a variety of experiences I otherwise wouldn’t have enjoyed. The hindsight of a decade and a half of adult responsibilities, however, makes me wish I would have traveled more during college when I had the opportunities to do so.

My second regret also involves travel, but this time a bit less costly. In early 2005, I was in my last semester of graduate school and living on my own. A number of my classes were in the Art & Architecture building, thereby exposing me to more experimental sketches, paintings, models, and exhibits than I had ever seen before. That year, word spread through the college that Christo and Jeanne-Claude were working on a new art installation; this was The Gates project, a series of saffron-colored archways draped with billowing fabric and lining the pathways of Central Park in New York City.

The project ran for two weeks in February of that year and photos of the orange structures against the browns, grays, and whites of a New York winter captured the attention of people worldwide, including me. I can recall at the time wanting to see The Gates in person, but I settled for simply scrolling through pictures online and changing my laptop’s wallpaper to a wide angle shot of the installation. Whether finances, classes, or fear kept me from traveling from Michigan to New York that winter, I can’t remember, but again the wisdom of hindsight tells me I should have bitten the bullet and gone. I was relatively free to come and go as I pleased, travel by train to New York City would have been simple, and I am sure that I would have enjoyed the experience.

The Gates: Two paths from a west entrance by Aaron G. Stock CC BY-SA 2.0

I draw multiple lessons from these tales of regret. First, take advantage of the freedom of youth. It will certainly be many years before I am able to travel as freely as I could in the period between leaving home and starting a new family. The image of a young adult backpacking through Europe may be trite, but there is a certain truth in the freedom displayed there.
Second, consider carefully the future implications of an offered opportunity. In the case of Antarctica, I will likely visit the continent someday, but who knows when that will be (probably on a birding trip when I’m old and bald). I continually regret not taking the chance in college to travel to a place so few get to experience in person.

In the case of The Gates, the place itself was not so important – I could hypothetically hop in my car tonight and drive to Central Park – but the transience of the experience was the primary loss. To have the chance to see something that existed only for two weeks’ time, and to look back a decade later to realize that whatever costs of money or time that I may have considered barriers then were insignificant across the scope of years, in some ways I regret not traveling to New York more than I regret missing out on the Antarctic expedition.

Third, learning proper financial management at an early age is critical to living the life you desire. As I mentioned earlier, I am sure that costs played a significant part in my missing out on both of these travel opportunities. Expenses aside, I may have not wanted to miss earning the few dollars I did in my student jobs so that I could make payments on my credit cards. If I had come out of high school and college with sound money skills (and no debt!), I likely could have easily budgeted for the travel that my flexible schedule would have permitted.

So, what big regrets do you carry with you? What stories of missed opportunities will you pass down to your children’s children? How will you advise them to make different choices in their lives? Feel free to contribute in the comments below, but most importantly, write it down and hand it down!

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