How do I plan ahead?

Late night contemplating and reflecting is how I operate. It's when the world and by extension my brain is the most calm and actually able to collect thoughts. I don't know if this is normal or if there's something wrong up there, but that's how it is and has been as long as I can remember.

Most if not all of my big project plans from the last decade stem from late night thinking sessions (often during sudoku or something else automatic). One thing that has always been hard and still is, is actually thinking about my life and my future. I don't think I really know how to do that. I can do it with projects and hobbies, just not life.

I make a point of keeping moving forward in life whether it slows down or speeds up at times, but I'm not sure if I'm living life or just staying alive or if there's even a difference.

I've never been a socially outgoing person, I don't seek out relationships or reconnect with friends, hell, I have trouble keeping up with the few friends and family I do keep in touch with, let alone seeing them and I don't feel a need to change that. This makes hanging out with myself my favorite pastime and boy does time pass, especially when working on my various little projects.

Project/hobby wise I have a pretty good list in my brain of where I want to focus, what I want to learn, etc. But as soon as it becomes something big like thinking about a career/stabler income or "life" my brain tends to either lose interest or lock down even if I'm trying.

I've talked about this with a few people and have gathered advice from some people I look up to or who seems to have things more figured out and I'll be trying some of that (basic exercising that isn't for a reason/going somewhere, journaling, meditation, reading or simply going outside for no reason), but even with that it just seems to come more naturally to other people to think about big questions and take actions towards their answers.

I've had a bit of therapy as well, but that was to deal with some things in the past, anxiety around medical stuff and ironically, overthinking. Whenever we got to the bigger stuff, it was of no help because my brain simply tuned out at that point.

Don't get me wrong, I think I'm pretty content with life right now, but at the same time there's nothing really ahead of me outside of uncertainty and the feeling of time passing me by.

Either way, it's almost 6 AM and I should really be asleep, so to sum up:

How do people make life decisions? Is everyone just going with the flow? How do you plan your future? I genuinely don't understand and am genuinely asking. How do you do it? Do you even do it or am I describing a shared experience?