It is only the result of these choices that they 1) need paychecks and 2) have already spent those paychecks.
I have a friend that works on a fish boat for 4 months out of the year, and spends the rest of the year hiking.
I have a friend that teaches middle school, and spends the summer months travelling.
They probably make less money per year than the paycheck-to-paycheck person you have in mind, yet they have the time to travel because of their lack of obligations.