Every time I describe my hobopoet lifestyle to someone in the "mainstream".... they inevitably bring up the topic of retirement. "But what will you do when you want to retire"?, they ask... usually with an expression of fear mixed with horror and contempt.
I never know how to answer that question. My most flippant response is, "I'm already retired". By which I mean, I'm already doing exactly what I want to do. I already feel free. I already have plenty of leisure and contemplation time.
Another answer that pops to mind is, in fact, the opposite, "I will never retire". Did Alan Ginsberg "retire" from writing poetry? Did Stanley Kubrick retire from making films? Hell, has Arnold Palmer "retired" from playing golf? When you are following your bliss there is no reason to retire. What would you retire to? Think of Timothy Leary. His bliss was to blow people's minds and turn people on and question consensus reality. Did he retire from that? Hell no. Not even on his deathbed. He turned his death into a final glorious piece of art.... his last challenge to the status quo (Read his book "Design for Dying".. written while he was dying).
Retirement is a hoax designed to help people endure a lifetime of degradation and monotony. Like "paradise" or "heaven", the poor drudging worker bees are assured a happy time of freedom at the end of their "careers". But if you spend 40-50 years doing drudgery, you become lobotomized. What do most retirees do? Play golf. Watch TV. Yipee, what a reward.
Hobopoets don't have careers. Their life is their career and they live it to the last breath. Retirement is for people who have wasted their lives doing other people's work... neglecting their own work... neglecting their genius.... neglecting their bliss.