To live like a bum in the US

I kick myself every day for not staying in and making a go of the Army. I went in a 17 also. They offered me flight school because of my placement level on visual acuity test and high score on entrance exam. Being young and Hard Headed cost me dearly, I could be flying some rich idiot around in a personal helicopter, instead I chose to become a forward observer,pretty much the complete opposite.
Hind site is always 20/20. I now own a painting company, not glamorous but its been good to me.
The only problem I see is when he gets tired of drifting, he'll be too old to settle into a career with enough time in, to get him through his old age, which as I know comes on quicker than we think.