This serendipitous wandering approach has its limits, though. It's not hard to end up quite far from home as the sun is going down! If I can keep track of the general direction in which I have been heading, and I know what time I left and what time the sun goes down, I can just keep an eye on the time and turn around to head home so I get there before dark. I can avoid busy streets unless I know a turn comes soon onto a quieter road. I can keep a weather eye out so I carry a jacket if rain looks likely. A water bottle is a necessity on a ride of any length, but then I should be setting out with some idea of how long I will be riding. Well, too, I need to be telling my wife how long I expect to be gone, so she doesn't get to worrying. There is a place for pure serendipity, but more commonly some rough sort of plan is needed.
Plans are good, but they often need to be flexible. There are many situations that can come up along a ride that indicate a change in plans is called for. A change in plans can be a shift into a more serendipitous mode, but I can also set out with a sort of network of route possibilities and criteria for deciding which to take as the ride proceeds. I might plan to ride to the grocery store to see whether they've got a particular product in stock. If I can get some there, then perhaps I will just head back home. If they're out at that shop, then I will head over to the next shop to try my luck there. Unless those rain clouds intensify, in which case I might head home anyway and try again tomorrow, assuming the weather clears up. This sort of network of plan fragments is a strategy, as the term is used in game theory. I don't know exactly what moves I will make, because I am not in total control of the situation. But I know what sorts of situations I might encounter along the way, and I know how I will respond for each of these possiblities.
To know all the different sorts of situations that might arise, that's a tall order! The world is full of surprises! One way to avoid surprises to to delay action until all the reasonable possibilities are understood... but that might be a very long delay, long enough to make whatever goal unachievable! Another way to avoid surprises is simply to be blind to them. One might manage to blunder through despite all, but more often this kind of blindness results in disaster. One can take a purely serendipitous approach to surprises, but that is not necessary. The unknowns are not all unknown. One can plan to learn. One can structure a journey using a variety of shorter explorations. These shorter explorations can limit the risk, so disaster is not so likely. But these explorations let us learn more about what situations can arise. Part of the journey is learning how to make the journey. The lessons shape the strategy, the strategy shapes the plans, the plans shape the lessons.
Why have we set out on such an expedition? Do we just want to see what we can see? Or do I need to get from point A to point B? I could be exploring for a place to engage in some profitable activity, for a forest were I can forage for mushrooms, for a farmer's market where I can busk, etc. Along my journey, though, my ideas of what I want might well change. My plan was to ride from Los Angeles to New York, but I discovered a violin maker in Des Moines and decided that an apprenticeship was my real way forward! My plan was to climb a Himalayan Peak but I became a tea merchant in Darjeeling! My plan was to sail around the world, but now I am working to protect lemur habitat in Madagascar! The goal shapes the journey; the journey shapes the goal!
It's not just that my journey involves discovering new goals. My journey makes me who I am. I am not the same person that I was when I set out! I am wearing clothes that I found along my way. I am telling the stories that I have heard along the way. The very shape of my body, my muscles, callouses, scars, etc. are the product of my journey. The I that started with one goal is not the same I that now has a different goal!
It's possible to resist this kind of fluidity. Once I have my made my mind up about something, I can just hold on and refuse to change. None of us lives so very long, after all! Holding on doesn't have to be forever, but just long enough. Ah, but even by holding on, that rigidity itself evolves. Our bones change their shape in response to habitual muscle tension! So in the end we cannot avoid a kind of serendipitous wandering approach to life. We can accept our own fluidity or we can refuse it, but that refusal is just another form of wandering.
We have come full circle, from serendipitous wandering back to serendipitous wandering. It's not a closure - it's an opening! This fluidity of my own evolution... I can start looking at ways to steer it toward more interesting neighborhoods, and ways to avoid the nastier surprises like getting caught in storms. This whole structure is a sort of helix, plans, strategies, lessons, evaluations... like a spiral staircase connecting level to level... the levels guiding and informing each other. What our lives are... incomprehensibly vast!

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