As Optometric Physician nears our 20th year, you and I have spent many Saturday mornings together connected by Off the Cuff. You’ve often agreed with my thoughts and sometimes not, but over these long years of writing to you almost every week, I feel that many of you have become friends, real friends, who know me.

The other day I was talking to Shannon about regrets—those moments in life when a wrong choice is made or a wrong path is taken. All of us have these turning points in the course of our lives. Some are relatively minor while others have the gravity to influence every aspect of who we are and what we ultimately become. Shannon asked me what my greatest regrets were. Since we’re friends, I thought I’d share them with you.

Like many of you, my parents had plans for me and my brother from an early age. I had other plans. My parents wanted me to attend the Bronx High School of Science, one of the most prestigious high school programs in the country. I wanted to go to DeWitt Clinton High, a large, tough, all-boys high school in New York City. So, I intentionally messed up the Science High admission test (which I never told my parents).

Clinton turned out to be even tougher than I imagined. My first day I ran a gauntlet of student criminals selling Converse All Star sneakers stolen from gym lockers. Tempting, but, no thanks. I was placed in the Scholarship Program for gifted kids, which wasn’t really that difficult or my classmates that gifted. At the end of the year my high 90s grades and Iowa Test scores landed me in Mr. Joe Prezioso’s office. Prezioso was a legendary Clinton football coach and, oddly, also the freshman guidance counselor. I was scared when I got the call, thinking I had done something wrong, but Prezioso smiled and told me that I, and one other kid from the scholarship class were being offered direct transfer to Science High. He said this had never ever been done before and that I needed to think carefully about it. I did, and made perhaps the worst mistake of my life. I decided to stay at Clinton and hang with my new stoner friends. I realized my mistake soon after. Science had one thing that Clinton did not. Girls, and intelligent ones at that.

I was always industrious and after school worked as a stock boy at Alexander’s, a legendary department store of that period. I was really into rock music like Hendrix and Clapton and saved my meager wages to buy my dream guitar, a brand new 1969 Les Paul standard gold top. I don’t recall how much I paid, but it was absolutely gorgeous and perfect with soap bar P-90 pickups and incredible tone. I had it professionally set up in Manhattan and played it for more hours than I can count. When I got married at the end of my first year of optometry school there was little time for playing and money was tight so I sold it. I can still recall how it felt to play it. Last I checked, had I not sold it, it would have been worth close to $30,000 today. Sigh.

My final regret has to do with flying. Although I’ve flown more than five million miles, there are some planes I’ve never flown and wished I did (and a few I did and wished I hadn’t). When I lived in NYC, I was among Delta’s most valued fliers back when fliers were actually valued. With a trip planned to the BCLA in England in 2000, I decided to use 240,000 of my frequent flier miles for a roundtrip flight on the Concorde through Paris connecting to Birmingham. I booked the trip, but idiotically decided that a direct flight from Newark made more sense, thinking that I would fly the Concorde at a later date. The Concorde stopped flying in 2003, and it will forever remain one of the planes I wish I had flown.

It feels oddly good sharing these regrets. If you would like to share yours, I’d love to hear them. Just shoot me an email. If I get deluged, I may not be able to answer all, but I promise I will read every one of them. See you next week.

Arthur B. Epstein, OD, FAAO Chief Medical Editor artepstein@optometricphysician.com