This paragraph reminds me of two book titles:
1. How to Fail at Almost Everything and Still Win Big
2. How do you measure your life
I have not read, just selected excerpts.
Is this paragraph of yours, synthesized out of these two books?
By the way, your post resonated a lot with me. We have similar tastes :)

Productivity is My Passion | Programmer | I Read Obsessively, Experiment Like a Maniac, And Write What Actually Works in Here.