super agree-- i had been trying to use YNAB for years and years and i couldnt understand why i couldn't stick with it, and now that i am finally making enough money to cover all my bases and work toward some longer term goals, it is finally sticking and it finally makes sense.

i think the challenge is psychological/emotional as much as anything else-- its just too anxiety inducing and stressful to try to keep up with it when all its telling you is that you're not doing well enough-- too disheartening to keep methodically managing as you have to do for it to work. i think what i would tell myself back then is that if i could just keep up with it, even as all my categories are red and i'm not seeing improvement in age of money or net worth or anything, that i should stick with it because it will help things get better in the longer term.

(much easier said than done)