Going with it, being intentional, going with it again?

I had a productive therapy session again yesterday. I've told the story here, but we talked a bit about the pivot point in my life where I stopped letting life happen to me in favor of being intentional. The short version is that, around the time I got divorced, I started being more intentional about life. That's everything, from the professional scene to dating. It was a strange time, because when everything got shook up, I realized that even my successes to that point were largely by accident.

But as we talked, I also realized that there was a certain blissful unawareness that I enjoyed at the time. It's not that I didn't consider potential, it's just that not exercising some intentionality meant there was little consequence to failure. You can't really fail what you haven't tried, if that makes sense. So despite the relationship problems and wandering aimlessly in pointless jobs, I wasn't particularly malcontent. It wasn't until I started setting objectives that life seemed to get harder.

What a weird realization to have. Culturally, we tend to associate achievement with content. There's no danger in just going with it. That got me to wondering if maybe that was a better way to go about life. If I objectively look at the people that I would describe as happiest, they're never the box-checking over-achievers. It's not that the go-with-its settle for mediocrity either. They just don't put all of their value and identity in achievement.

To be honest, I was not without achievement in my pre-crisis life. I mean, I did graduate from college, and navigate a career change. Those count for something. But emerging from the crisis, I landed with an excellent partner (and dated a pretty great then-future DVM). I leveled up my career by going to Microsoft. I moved six times to get it closer to right. That was a lot of deliberate change that has objectively left me in a much better place. But with that, I feel like there's always pressure. Sometimes, that weight gets to me. Was it easier before?

This is another one of those pendulum things, where you go far in one direction, then the other, when you belong somewhere in the middle. It seems most things in life are like that.