I also don’t think homeschooling has anything to do with it. My daughter went to public school and had terrible exec functioning skills. (While my other daughter is super organized.)
We didn’t realize it until about 8th grade when the workload got heavier and harder. And each year the kids were supposed to be a little more self sufficient.
She was diagnosed ADHD-PI in 8th grade (she was so NOT hyperactive, that it never occurred to me. She is “PI” predominately inattentive). I remember a big thing was “slow working memory”.
She is just like her dad (my husband) and they are just wired differently. And it is hard for an organized person to understand - why, exactly do you need to keep a toothbrush in the kitchen?? (It makes sense in their mind.)
Learning about ADHD has helped me with my husband. For example, I don’t ask either of them to put away their X. They take that as I want them to do it immediately and get flustered. Now I say, can you put away X this week?
After accepting it, DD tried various meds and found what worked for her . But she was still a mess through most of high school.
She started working her senior year of high school, which really helped her time management skills.
And I let her be in charge - of school, talking with the doc about her meds, etc. I intervened less and less.
She decided to stay home and go to a local community college and boy, did things turn around! I think part of it was maturity (ok, I do have this issue and general maturity) and part “I am in college now and have to do this on my own”.
She kept her job, working about 12 hours a week and takes about 10 or 11 credits a semester. It is a good combination for her. She has asked us for advice on which classes to take and the like, but otherwise, she has done it all on her own, meeting deadlines, getting her accommodations, meeting with her advisor, stalking professors, etc.
She has been at her comm college 3 years and loves it. She is finishing up this year and transferring to a state school near us. She is going to commute there, so she can have the flexibility to go less than full time if she feels she needs to (she can’t live on campus unless full time).
She got a book on her own, “Learning Outside the Lines”. I can’t vouch for it, but I came across it the other day and it is full of post it flags!
She also uses a big day planner. And I think it has been helpful that in college, all her class stuff is online, so she can check due dates, if she turned in assignments, etc. (Teachers were much It was less consistent in high school.)
Good luck! He will get there. He just needs to take his own pathway and do it on his schedule.