I don’t think there has been any point in my life when I had open-ended time to myself. That is to say, a period where I could have gone and done anything without eventually violating somebody’s expectation that I would be in a particular place at a particular time.
As a child, nobody is in a position to determine the shape of their life (those who are forced to do so early are forced early into adulthood). In high school and university, there are breaks with defined endings. While working, I have applied for and received defined periods of vacation. I accepted a university position before finishing high school, accepted a grad school position before finishing my undergraduate degree, and accepted a job before finishing grad school. Now, I expect to accept a new job before reaching the defined endpoint of my current one. My calendars – literal or figurative – have always included a “first day at X” entry, somewhere out in the future.
I suppose the logical opposite of all that structure is the life of the aimless wanderer: the protagonist from On The Road or The Adventures of Huckleberry Finn. In addition to lacking obligations to appear at such-a-place and such-a-time, such characters tend to be unencumbered by burdensome possessions. Making the transition from one of those states to the other – in either direction – seems daunting. Both transitions highlight the limits of human freedom. Going from an unscheduled life to one filled with obligations involves accepting the restrictions that the expectations and actions of other place upon each of us, as individuals. The universe simply will not provide for us to do whatever we wish indefinitely. More grimly, the transition from structure to an open-ended existence seems inevitably bound to the idea of mortality, and the certainty that there will be a definite end to freedom as some unknown time in the future. Being cast into that expanse, without the benefit of near-term signposts to distract from the dire conclusion, seems likely to be frightening and macabre. Perhaps that perspective shows how I am more concerned about risk than excited about opportunity.
All told, certainty is a valuable thing. Similarly, if one wishes to influence the world, it seems promising when there are expectations about where one will be in the future, and what one will be doing. Still, it could be an interesting experience to face the unknown span of all of one’s remaining life without seeing significant set markers.