My take on your case @reewritesthings is that we all have tendencies to plan and anticipate what lies ahead. This might be an effect of our obsession to make things go according to our plan. We are so afraid of failures and mishaps. While it's not really a bad thing, if this goes out of hand, we tend to overthink and stress ourselves over things we don't have control.

I was like you before. I am borderline OCD, I guess. I grew up as an achiever, so I always see failure differently. I want to be in control of everything.

Everything changed when I tried things I'm not comfortable doing. They're not bad things though. I hang out with easy-go-lucky people. We adopted a "no cancellation of laags" mindset. We tried hiking or mountain climbing even if it was raining so hard.

You just have to loosen up a little and you'll be amazed of how adaptive you are.