feedback please . . .

Hypothetical situation. Let's say there is this guy, about to turn 50, not sure what he's seeking, but let's say 'experiences to bring him nearer to discovering his authentic self'. Let's describe his personality as: quiet, easy-going, non-judgmental, open-minded, introspective, somewhat naive (okay, gullible when it comes to trusting the 'good' intentions of others), timid in new situations, likes people but likes solitude as well, and somewhat ill-at-ease with the mechanics of living in a day-to-day work-a-day world for any sustained length of time. . . . Let's say his current situation is: unattached to any particular location, lacking any marketable skill for income above minimum wage, zero net worth or financial means (voluntarily surrendered a comfortable lifestyle and meaningless sheltered existence), very few possessions (a modest-sized duffle bag would do it), unencumbered by commitment, responsibility or emotional ties. And, for shits and giggles, let's just say he has a propensity for haiku/tanka/senryu and photography. Now . . . the hypothetical question . . . This guy would like to travel about, seeking new experiences, meeting new people (to touch and be touched by joyful lives) and to blog these experiences with haiga. But he doesn't want to go so far as to find himself as a wandering-beggar-monk (at least not yet), doesn't want to find himself in a homeless shelter, sleeping on the street or stranded in some unbearable situation. How does one begin? What kind of choices/opportunities/paths are available? Please! all input welcome!