The Right Regrets

When you get to be middle-aged (and admittedly, beyond), the topic of regrets comes up a lot. I’m pretty lucky. As Frank Sinatra sang in “My Way,” I’ve only had a few.

Regret #1: Travel. A couple of months ago, I wrote about how I never got to attend my first choice of colleges, Emerson in Boston. That’s one regret, but another collegiate one is never spending a semester overseas. Stanford had wonderful campuses in Cliveden and Florence, among other places, but the idea of going to another country – even though I’d traveled all over the U.S. – petrified the emotionally immature me. (So what turned out to be the first country I visited outside of North America? Morocco!)

Regret #2: Quitting. Another of my college faux pas related to the school newspaper. I was a prolific writer in the entertainment section, writing dozens of movie reviews and other articles, so it seemed only logical to promote me to editor of the department the following year. What a disaster. I was way out of my depth; I once cut inches off a review of a Journey concert to keep my own review of Gone In 60 Seconds intact (much to my embarrassment now). Worse, my schoolwork started to suffer, so I quit after only a few weeks.

The paper’s editor begged me to reconsider, and in retrospect, I wished I’d figured out a way to make it work. Especially since the guy who replaced me now works at the New York Times.

Regret #3: Athletic Events. On October 17, 1989, thanks to the largesse of the publisher of the magazine I worked for at the time, I was sitting in Candlestick Park waiting for game 3 of the World Series to begin. There was a slight interruption, which we know refer to as the Loma Prieta earthquake, which rendered Candlestick temporarily unusable not only for the Giants-A’s game but for the 49ers-Patriots game the following weekend.

The latter game was moved to Stanford Stadium, and a friend of mine offered me tickets. What did I do instead? I went to the office, having missed work both the day of the World Series and the following day while we waited for the office to be declared safe. You know how they say no one ever sat up on their death bed and said they wished they’d spent more time at the office? I am the idiot who spent more time at the office.

Regret #4: Philandering. For most of my dating years, I seemed to be under the impression that monogamy was actually spelled m-o-n-o-t-o-n-y, and I hurt a lot of women when that particular illiteracy – spelled i-d-i-o-c-y – came to light. I’ll just chalk that up to the aforementioned emotional immaturity and be thankful that my spelling improved when I got married.

Regret #5: Trusting the Future. My friend Andrew frequently reminds me that the philosophy of mine that he loves the most is “live life according to a theory of abundance.” I didn’t always have this philosophy, unfortunately. In 2002, just after the storied technology downturn, I was out of work and collecting unemployment insurance (and damn happy to have it). It was a gloomy time, but a medical-school friend of Monica’s had taken a fellowship in New Zealand. I have always regretted – especially in light of the way my career subsequently improved – not just putting that very expensive jaunt on a credit card and heading south to see them.

Dear Abby once said that you can measure a man’s character by the things he’s ashamed of. I don’t know if regret and shame are the same, but they’re pretty close. Playwright Arthur Miller once wrote, “Maybe all one can do is hope to end up with the right regrets.” I hope these are the right ones, because they’re sure the ones I’ve learn from.


About middleagecranky

The Middle-Age Cranky blog is written by baby boomer Howard Baldwin, who finds the world, while occasionally wondrous, increasingly aggravating.
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7 Responses to The Right Regrets

  1. Bill Roberts says:

    There’s a decision point behind each regret. I decided this, not that. I chose door No. 1, not No. 2. Then as life plays out and I look back I begin to understand the path not taking might have been the better one — that’s the “regret.” Every important decision I make has a “price” and a “payoff.” Sometimes with the passing of time we forget to remember the payoff. Thinking this way doesn’t help me change the past but does help me understand the choices I have to make in the present, making me ultra-aware that any important decision I make today has a price and a payoff.

  2. Bob James says:

    When she worked years ago in one of Apple’s stores, my wife could have bought Apple’s stock for $6 a share; but instead spent the money on computer accessories. When I was admitted to Notre Dame University, I was invited to a private lunch in New York City with the then-leader of the “Irish Mafia” (the Catholic equivalent of Yale’s Skull and Bones, the club for the “masters of the universe”). I blew it off, because he was a “capitalist pig” (the man was the CEO of Exxon at the time). Our regrets could fill more blog posts than all the servers in the world could host.

    Wonderful post!

    • When I was working at Macworld, and Apple was about $18 a share, I advised a reader to sell when it reached $25. I just hope (1) he didn’t or if he did, (2) he can’t remember me or (3) he can’t find me.

  3. Good stuff, but I’m confused by #5. Do you mean NOT “just putting that very expensive jaunt on a credit card …”

  4. southseattle says:

    Quote from a movie The Ice something or other: “Everybody has regrets; men our age, that’s all that’s left.”

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