For of all sad words of tongue or pen
The saddest are these: ‘It might have been!’
– John Greenleaf Whittier (from the poem “Maud Muller”)
Regret is an unpleasant emotion. It’s that niggling doubt, that suspicion that you should have played your hand differently in a certain situation. By far the biggest regrets I have are for those times when I knew deep down what I should do but ignored that inner voice and did something else. Most often, it’s been because I chose to take the easy road. I did not what I suspected I should do, but what I thought other people—maybe family or friends—would want me to do, or because I was trying to fit in with my peer group or society as a whole. Those are the big regrets.
There are also little regrets, usually for times I held back and did NOT do something. In general, I think it is better to go for the gusto and possibly fail or look foolish than to hold back, trying to maintain a cool detachment. Far too often, I have chosen the latter course.
Here’s a story about a time I did not hold back. I was alone at a bar (always awkward) and I thought I saw a girl I knew from way back in grade school. The bar was dark, and she was on the far side of the room, so I really didn’t get a good look at her. Furthermore, I was sitting at a bar in Boston but had gone to grade school in Des Moines, Iowa. The person I was looking at would have been someone I hadn’t seen in over 10 years, and I had to mentally age the girl I knew in grade school into a young woman. In other words, there was a good deal of imagination at play on my part. Still, she looked attractive and I spent quite a while nursing my drink, wondering if I should approach her.
Eventually I worked up the courage and began making my way across the crowded room to where she and her friend sat. As I neared them, I could plainly see that she was not the person I thought she was. This was not Ellen from Woodlawn Elementary School. I felt powerless to stop myself, though, as if once in motion this body had to complete the task at hand. So I went up to her and said, “Excuse me, are you from Des Moines?” which is probably the only possible pick-up line dumber than, “Hey, baby, what’s your sign?” Happily, she didn’t laugh in my face or throw her drink at me. She just replied, “No.” I apologized for interrupting, forced a smile, and slunk back to my spot. I’m pretty sure I paid my tab and left as quickly as possible.
BUT…do I regret doing it? Not at all. I may have looked foolish, and I certainly gave the woman and her companion some fodder for giggles, but I am glad to this day that I didn’t pass up a chance to connect with someone, even though the someone wasn’t who I originally thought she was and the connection lasted about ten seconds. If I hadn’t gone over to her, I would still have that niggling sense of doubt. This is a small and silly example, but it’s one I need to remind myself of from time to time. Go for it!
“Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.”
– apocryphally attributed to Mark Twain (https://marktwainstudies.com/the-apocryphal-twain-the-things-you-didnt-do/)