I have a bad to-do habit. I make big ambitious lists of things I want to do, then let them pile up in my to-do app until I’m so scared that I quit the app and start a new one. (I, like several Lifehacker commenters, don’t know how I got a job at a productivity site.) But I’ve found a way out of my to-do debt.
The Shape of Design author Frank Chimero keeps a sophisticated to-do list. He estimates the difficulty of each item, so he doesn’t overload any one day.