Essay 2 min read
Regret Comes With Choosing
On the choices we drift into, what our regrets say we care about, and what to do about it now.
We regret choices we made back when we didn't care. The trouble is, we care now.
Most of us keep a quiet list of the paths we never unlocked.
If only I had taken that class seriously, instead of sleeping through it.
If only I had chosen my major myself, instead of following the crowd.
If only I had applied for the role that felt out of reach, instead of taking the safe next step.
If only I had talked to that person at that random event, instead of letting the moment pass.
Yet at the time, most of these didn't feel like decisions. The class was just something to get through. The major was what everyone else picked. The job was the obvious next step. And the moment was gone before we noticed it was one.
We never noticed we were choosing
Looking back, we didn't weigh these choices badly. We didn't weigh them at all. When we're young, every decision weighs the same. We watch the show, let it unfold, and follow the crowd.
But every choice puts two weights on the scale against its reward:
- The friction of making the choice happen
- The cost of losing another opportunity
In the moment, we only feel the first one. Years later, the second one is all we can feel. That's the lesson regret teaches: even when a choice is hard, make it, because the friction is the trade-off for the reward.
What the ache shows
In The Necessary Ache, an essay in Philosophy Now (the short version in the library), Tara Daneshmand argues that every choice closes other doors, so regret comes with choosing, not with choosing wrong. The ache shows what we cared about.
So it's worth asking what the ache is pointing at. A skill we skipped stings most when the world we now work in prizes it. A path we didn't take stings when we watch the people who took it valued more. A conversation we never started stings when we're still hoping to meet the one.
What we can do now
So soften the blow. Our younger selves couldn't even imagine what they were giving up. Maybe it was the best choice they could make at the time. We can't blame someone who didn't know they were choosing.
But we know now.
So we let the ache point the way: practice the skill, focus on the career and do our best work, build our confidence, dress up a little, take care of ourselves. And when the next chance comes, we do it differently.
We start the conversation.
