The things that we would regret on our deathbed are not the things that we care about day to day.
There is a well-trodden concept of immediate versus long-term pleasure. We realise there are things we could achieve but they necessitate a lot of pain, a lot of sacrifice. Then there are the low hanging fruits of life, things that give us enjoyment in the moment but are quite base and transient, certainly not the stuff of legacy and meaning.
People can be driven by an abstract sense of enjoyment, one where the action itself is unappealing but the idea of being a person who undertook that action is deeply appealing. It’s like the difference between being an “adventurous person” and actually putting in the effort of going on an adventure. It’s unfair to describe this desire as surface-level or shallow, it’s not about appearances (although in some cases it can be), it’s a higher-level desire, something more abstract, more philosophical. These are the thoughts that plague people when reflecting on their lives, their regrets.
“Regret is always about things we did not do; remorse is about things that we actually did.”
To me remorse makes sense but regret seems so irrational because it has too many assumptions built into it. As a piano teacher, I often hear people say that they regret stopping their piano lessons when they were younger because now they wish that they could play. But learning the piano is quite boring and tedious, in fact that applies to many skills beyond that. The vast majority of people would hate learning the piano even though they might like the idea of it.
Similarly, people’s regrets are more about ideas than realities. The tantalising prospect of the roads we didn’t take can haunt us: they offer the promise of who we might have been. Closing the door to these possibilities is tantamount to breaking those promises to ourselves. However, I want to make a defence of the day to day, the simple pleasures and small victories. Those are, after all, the stuff that life is mainly made of. If you’re satisfied at the end of a day then that’s enough and if it’s not enough then it’s a great start. Think of it like a day-to-day deathbed.
For the defence of the day, I agree that we should celebrate each, or almost each, small victory we make every day for journeys are not made in one big leap, but many tiny steps, not necessarily on the same path, because we don't always know we are going in the "right" direction. On the other hand, I do think we should have a long-term goal in mind which helps determine whether we are going in the "right" direction. The reason I put the word right in quotes is because it is relative to where we are going. Otherwise we may end up making a thousand victories every day and still not having any "big" victory because we took a thousand steps in a thousand paths that may not all lead in the same direction. Same contrast you see between being a generalist and a specialist or being a jack of all trades and master of none.