Some environments teach you to cope with uncertainty better than others. I could insert a long discussion about being "productively lost" in open source communities here, and indeed, it's the framing I expect most people reading the Teaching Open Source Planet or Planet Fedora to have. But I'm in Bangkok right now, so I'm going to talk about arguing with tuktuks (motorcycle taxis) instead, and I'm curious whether folks find anything in here that resonates with them in any other context.
Travel in Southeast Asia is an exercise in coping with chaos. There's no guarantee a taxi driver is going to take you where you want to go, you need to haggle for the fare in advance, and sometimes they'll try to take you to another place (a store or somewhere they'll get a commission for bringing potential customers to) so you need to be Constantly Vigilant, and sometimes you get a good driver and sometimes you get a bad one (at which point you get out), so you just take that into account, haggle, watch where you're going, and know it's all part of the process. Oh, and traffic. Unpredictable traffic is also part of the process. Transit time is plus or minus 80%. Or so. If you're lucky.
But! You can go to offbeat places, ride interesting vehicles (see: jeepney) and the potential for interesting things happening en route is higher - on the way to the temple today, our driver stopped in the middle of a traffic jam, ran into a nearby shop to drop off a bag, and then leapt back on the motorcycle and continued driving as if nothing had happened. If you're a twenty-something on vacation, like my (American) friends and I were today, it's awesome.
However, possibility and uncertainty are hard if you live here and want to make it in time for your dental appointment. Which is why predictable systems are nice; in the States where I typically live, you get in a taxi and it's almost certainly going to get you to your destination in a reasonable amount of time, and the fare is set by the meter. Being able to abstract away the details of "transportation" lets you worry about other things that you might consider more important - you can zone out on the bus and work on your next novel, for instance. The bus is probably not going to kidnap you. Probability of needing Constant Vigilance: lower. Adventure and possibility quotient: also lower, in a way. It's not that one is better than the other; it depends on what you want.
People make trust networks to increase the probability they'll get predictable results. Public infrastructures for transit, food, fire brigades, libraries, etc. are socially constructed in exactly the same way as private ones - they're just country-sized. My transit trust network in the States is public; in the Philippines, it's private, because I may not trust a random taxi driver, but I do trust my aunt. This sometimes leads to the tendency to only roam within that network, because it is (1) safer and (2) more effective that way. You always get picked up by someone you know, you always call ahead to a friend of a relative of a friend to be your guide in a new place, and you watch over your guests with the same sort of Incessant Vigilance given to you as a guest. It's not that there aren't bad eggs within that trust network - but they are exceedingly rare and get rooted out rather quickly. And it's not that there aren't good people outside it, but it's sufficiently hit-and-miss that it's not worth looking; the search time becomes too high an opportunity cost, so why waste your time when you can get the same thing
done more safely and efficiently within your network?
Because sometimes you can't. When you transplant that kind of trust network to a place that does have good public infrastructure, it becomes restrictive - you continue to only see that little subset of the world, but now instead of being significantly safer than the rest of the world (and thus logical to stay within), it makes no difference, and it's better to be able to just trust and wander freely. Again, it's not that one system is inherently better than the other; it's that they evolved within (and are therefore better suited to) different sorts of environments.
It's hard to recognize that context shift, though. My (Filipino-born) parents freaked out when I started using public transit in Boston during college because oh my gosh public transit isn't safe and god forbid I should take a taxi. You can say "well, how will you know if you don't try it?" but it makes sense. if all revolvers in your experience contain a bullet in some chamber, and you know some folks who've lost Russian Roulette, you don't pick up a random gun and hold it to your head; it's uncomfortable even if someone tells you that all the guns in this room are unloaded (how do you know you can trust them?)
And vice versa. Looking for a global order that's not there is just as frustrating and fruitless as not being aware that there is one that you're expected to learn beforehand. If you expect an underlying order and safety, it's disorienting to be plugged into a chaotic world, and you don't even know you need to look for (and be adopted into) one of those "safe networks" in order to really function. If you don't have that sort of personal network nor the time or inclination to build it, you can buy access via someone who does.
Up 'till now I've been speaking as if these things were a binary: order or chaos, trust networks or free wandering. Black and white make for good drama and simple contrast, but the world is closer to a morass of shifting shades of gray; different environments have different degrees and types of chaos and unpredictability and danger, and they change - some faster, some slower, some bigger, some smaller. Stable countries have revolutions; war-torn neighborhoods unite themselves. And so coping mechanisms also need to be a mix that shifts over time.
The tricky thing is that it's hard to tell what mix to use unless you (1) know yourself and (2) know the situation. You can't always know the situation in advance, and "is there a script, or are we improvising - either way is fine, but I'd like to know" won't always get an answer. So if you switch contexts often, you try to know yourself and your own preferences, and the indications you need to personally look for in order to adjust your mix of coping skills and the trust network you're building to give you a risk-reward curve that works for you. I'm a lazy bum who hates advance planning  and has an affinity for improvisation; I think it was Max who once said to me that when your plans run out, all you've got left is improv. When I err in this balance, it's by not having plans to run out of. If I didn't like improvisation (because my life required advance planning and stability for whatever reason), I'd probably not switch contexts so often, or have a network precede me - Mel-proofing the world vs world-proofing the Mel.
I think this is why people say travel broadens the mind; it thrusts you into so many different unfamiliar situations that you stop living situation-to-situation and pull back to see the bigger picture of how you cope with different sorts of structures so you can choose the sorts of structures you function within, and change how you cope with them to better suit you. I'm not sure how to teach this sort of metacognition to students - or perhaps more accurately, how to design experiences so students will be more likely to have that sort of realization for themselves... but that's something I've been thinking about over the past few days of alternating between predictable and chaotic transit systems.
 It's what tour guides do for tourists, they abstract the messiness away, just like open source consultants/companies take on the "community risk" so their clients can be assured of (monetary) input X becoming output Y.
 I also tend to operate in environments that change so quickly that advance planning tends to be useless - grad school will be an interesting paradigm shift here.
 I'm off to Berlin tomorrow, where there will be an unfamiliar underlying transit structure (order, solo - until I meet Sebastian at the train station, at which point it becomes order, guided) - this should be fun after a week of arguing with Thai taxicabs (chaos, solo) which follows a week in the Philippines of only being allowed to sit in cars driven by family members (chaos, guided). Just call me context-switching-girl.