D27 – Deepest Regret

Dear J-

The “thing I most regret” mostly reduces down to the one thing I wish I had more of: self-esteem (though you may now say I’ve flipped to the other side of the coin), which in turn leads to courage and all those good things. Honestly, I don’t do much regret in my life; regret means that I wish things were different now, and I by no means want change at this point. Yes, I know it sounds complacent and lazy, but that’s also the border between satisfied and whining.

We can always head back to high school to uncover those regrets stemming from not believing in me: not fast enough, not good-looking enough, not popular enough, why isn’t it enough? I used to (and I’m sure still do) tend to wait for things to happen, rather than going out and making them happen, afraid of rejection or worse failure. But now, you try, you try again if it’s not enough. It’s immensely liberating to try things while taking a reasonable eye to caution, rather than sit and worry through five different paths to failure before even starting.

I wish that I’d had the courage to do what I wanted to do, that I’d been able to make more decisions selfishly. There were weeks on end that I thought through all the people who’d end up hating me because of what I wanted, and why it wasn’t enough justification. You know, J-, I never asked you out the thousands of times I thought I would or should have because the timing was off, dating back all the way to eighth grade. Or the distance was too far. Or I was afraid of making enemies of exes. Or or or … it all boiled down to not wanting to make a fuss, not wanting to fail. But not wanting to fail made me never want to try in the first place; it wasn’t until halfway through college that I realized failure wasn’t the worst fate in the world.

Even though failing might mean that something ends, it inevitably signals the start of something else. And without that impulse to try better, try harder, it’s all to easy to slip back into our comfortable soft lives. Perversely, I look forward to hearing folks around work pointing out where I’ve screwed up; it means I’m doing something, that I’m active in this world. The simplest way to be perfect, after all, is to do nothing, to risk nothing and perhaps gain only the serene smugness of inaction.

Mike

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