You seem to be more self-aware, more reflective, and more at peace with yourself than the average person - less anguished by desire. Being zenlike is a skill. If your profile picture is anything to go by, you may have more philosophical knowledge than average.
My coping mechanism as a lazy slacker is telling myself that no matter how good I'll get at something, I'll always be plagued by the desire to get better in that area and in something else. It's also why I can't really answer the question of "what is your dream life" because I know I would always get bored and want something else. I cheat and say "living in an advanced virtual simulator that would allow me to experience anything to my heart's content, and periodically mind wiping myself so I wouldn't get bored after experiencing so much". The other idea is just wishing for eternal peace in the void. It's a constant clash of desires.
I don't know much about Diogenes, but I've wondered what if he were born in this age, and I have this amusing picture of him living as a homeless person, leeching off Mcdonald's wifi on a stolen netbook with pirated Windows OS to shitpost on the internet. Or maybe as a van dweller, or a truck driver that makes their truck their home.
