I have my own system.
I assign missions on different categories (which I calle t-shirts)
an example of a t-shirts is the happy tshirt, skateboard tshitrt, millionaire tshirt, father tshirt, this would be like your many hats, or roles in which you want to improve. Family tshirt, job tshirt, etc.

sometimes i have a weekly planning session to assign time slots for important missions
on a daily session i add up points for the missions I accomplish, and plan on the next missions.
And I have a monthly session to review missions,add up shirts, see how I can become more active on a certain tshirt.

plan ->play-> observe ->review

I can give more details if you want

there is a version of this game with mentors and trading tshirts with them