[Figs]

> It probably isn't far off to describe my struggle to manage these as mental illness rather than a productivity hurdle

You might try asking your healthcare provider for help finding a therapist or social worker. They can help you assess the issues you are facing in a way that's different from what you'd get from friends or family (for example such discussions are generally confidential), and they can check-in with you regularly if that's useful for managing your problems.

[rajlego]

I've had a therapist before but they unfortunately didn't help as much as I'd hoped. I can often make systems that last a few weeks but single failure days cascade very easily. My hope is that with external accountability I can bootstrap these systems into working for months and become the kind of person that can reliably manage myself

[Figs]

You might have to try a couple therapists before you find the right one -- I'm on number three personally (with many years and much denial in between) -- but when you find one who you work well with it can be very helpful. Your desire for weekly analysis of your feelings and help debugging motivational issues is generally up their alley; I check-in with my therapist once a week via video call and our sessions often explore what's going on when I have low motivation. You might consider giving it another go, but up to you. Keeping a daily journal -- if you don't already -- may also be useful.

Regardless, I wish you the best of luck with your challenges and hope you find a solution that works for you.