You seem to have it cracked, EndlessJourney. Perhaps I can persuade myself to have faith in my future self?!
Well, to be honest, I don't think the way we do things works for everyone. Especially amongst FIRE folks. I find myself disagreeing with a lot of opinions on this forum, so I know my views are definitely in the minority.
IMO, you've got to make retirement work for your personality. If your comfort zone is to think and plan and overthink and overplan, then don't fight your nature. I don't think it's possible to transform yourself into a Type-B personality if you're naturally a Type-A, which most people that aspire and achieve FIRE are.
Again, this may be an unpopular opinion, but I say lean into it!
Create a plan. Think of every possibility. And then every contingency if those plans don't work out. And then continue refining the plan as you're going along, when you have more experience or after bouncing your thoughts off others. You may even find an odd comfort in the midst of the process of thinking and planning.
I think the worse thing you can tell a worrier is, "Don't worry so much!" Utterly unhelpful.
It's just like telling an angry person, "Calm down, buddy"... Cause that works *so* well...
Except, being a "Type-A" person as a professional does not mean that someone *is* a "Type-A" person.
In fact, I despise those designations, as they are behaviours, not identities, and the more someone identifies themselves according to their own behavioural patterns, the more they corner themselves into those patterns.
There's a difference between being someone who really enjoys planning and micromanaging, and being someone who has an ingrained habit of planning and micromanaging because of a long professional history of needing to do so to thrive.
OP sounds stressed by the urge to try and plan, it sounds more like a discomfort with the unknown rather than a joyous anticipation of options.
It's like the difference of really enjoying the planning phase of a vacation, vs people here who stress endlessly about their WR and try to anticipate every financial risk that could befall them.
Are both "Type A"???
Who knows, who cares?
Behaviours are all manageable. If the behaviour is enriching your life, then foster it, if it isn't, then modulate it.
Lastly, just because a pattern of behaviour is ingrained and automatic, doesn't make it who the person is.
I thought I knew who I was based on my behaviours, but it turns out those behaviours were entirely context driven. I'm not competitive, I'm not performance driven, I'm not all of those things I believed I was for years. What I was, was highly motivated to be competitive and outcome-driven because my goals at the time required that behaviour.
Now they don't, and now I'm not.
The crux of my advice rests on OP giving their future self the space to figure out who they are, what their motivations are in the absence of the pressures and motivations that came from career goals.
Who knows, OP may become far more micro-manage-y if that's what future self truly enjoys.
Hell, I had no clue I was a neat freak. No clue. Not until I had the free time to keep my house absolutely spotless because what the hell else am I going to do with my ample time at home?