Solutions to Life's Dumb Problems (Part 2)
How do I set Goals and Improve my Mental Circumstance? How do I Not Procrastinate?
How do I Set Goals, Think About the World or Improve my Mental Circumstance?
First, take a look at Stoicism - yes, I mean the ancient Greek/Roman school of philosophy. Chances are good that what you think you know about it is wrong. It isn't about abstaining from all pleasure, sleeping on beds of nails, or some kind of unwholesome elevation of suffering to an art form. Instead, it offers a suite of surprisingly practical and pragmatic ways for maintaining a productive, optimistic, and healthy state of mind. I see it as the Western tradition's version of Zen.
I also find there is incredible profundity and value in the Tao Te Ching and the writing of Nietzsche (worth the price of admission for the mustache alone), however these are works for musing deeply, not practical guidebooks like Stoicism.
I Seem to Flail Around and Procrastinate - How do I Get Things Done?
Timeboxing offers a bevvy of non-obvious benefits for personal projects. First it tends to feel surprisingly liberating, rather than constraining. Procrastination is often a defensive mechanism: by not starting you can't fail to live up to your own expectations. If the task is poorly defined or you aren't entirely confident in your ability to complete it "well enough", this risk is likely. Timeboxing helps address both issues at once: you are no longer comparing your results with your Platonic Ideal result, but with the best you can get done in the next 25 minutes. This more reasonable expectation will make you naturally prioritize, and judge your own results more fairly. As a bonus, timeboxing can sharpen your estimation skills as you see how many boxes it takes to finish different tasks.
A good way to get started with the Pomodoro technique & timeboxing in general is to try it out on straightforward chores. Have a room you need to clean that you've been putting off? A car to wash? A letter to write? Set the timer and get crackin'. You'll look forward to the well earned break and probably make a lot more headway than you expect you will in a short amount of time.