This is a great tool. One of my goals is to simplify my life by using checklists, schedules, software and other tools to avoid quotidian decision making.

The problem is that many important goals are not easily quantifiable; the partial solution is to reformulate goals in such a way as to admit quantification.

For example, if you want a quantifiable way to improve your math skills, download a formal proof checker and prove the 100 theorems listed here (or find an easier set). Another interesting possibility would be to create a wiki of canonical hard programming problems (e.g write a Lisp interpreter) along with test suites to determine if an implementation is correct. Then you can quantify your progress on the route to hacker nirvana by counting the number of hard problems you've solved. When you've solved all the problems in one language, start over with a new one.