What they did
A parent (u/Worldly_Beautiful557) designed an executive-function coaching setup for their son, who has ADHD and had recently moved out, running on his own ChatGPT Plus subscription. It used one main chat for schedule, email, goals and check-ins, plus dedicated Projects for bigger tasks so context carried over. Custom instructions told ChatGPT to ask one question at a time, work around his actual schedule, and give a single manageable next action with a clear endpoint. For a room he couldn't face clearing, the son took a video of the mess and asked ChatGPT in a Project to build a plan.
How it went
The son worked with ChatGPT to produce a room-cleaning plan with a completion date, time around his work schedule, and stages for sorting, packing, cleaning and moving furniture. The parent says it is early but working well: he now uses it on his own to plan and research his goals, tells them in advance when he will work on the room and what the outcome will be, and the excuses about not having time have stopped.
Worth knowing
The parent added automated, humorous email nudges from their own assistant until the son's ChatGPT emailed back to confirm the plan was made. The instructions also handle getting stuck: identify the obstacle, make the step smaller, and restart after a missed day without piling on extra work. The poster discloses that ChatGPT wrote most of the Reddit post itself, and a commenter questioned whether the approach truly fits executive dysfunction.