When I was eight we took a family trip to Washington DC. I found a book for kids at the library that contained all the museums and monuments that one could visit - a Fodor’s for fourth graders. My little brain fired up its still-developing “make and complete lists” neurons and a few days later, voila, we now had a timetable. We were also going to stick to said timetable whether every last family member liked it or not. I don’t (choose to) remember the exact circumstances but at some point, tears were shed over that list. I do, however, remember the Apollo 11 command module at the National Air and Space museum.
As a slightly older child, my obsession crosshairs shifted to playing Legend of Zelda on Nintendo. Navigating through each new world and solving the various puzzles was a different way of traveling, but entirely safe (minus eyestrain from sitting too close to the TV) and entirely free (minus the opportunity cost of other more economically lucrative activities like mowing the lawn). Zelda, too, had a guidebook at the library. If you were stuck on a puzzle or you missed some of the character dialogue, you could read up on ideas for how to find Saria, the sage of the Forest Temple, in the paperback supplement.
Two decades later, that eight-year-old’s ambition for the perfect itinerary looks positively pedestrian compared to what making and completing lists has morphed into. There are already thousands of perfect itineraries to choose from, replete with Foursquare tips, Yelp reviews, and Pokestops, which I hear is a word now. And like Zelda, the perfect guidebook is always available to you, immediately and for free, if you want it.
For a long time I was heavy on guidebooks, and didn’t see anything wrong with the concept. More information is surely better, right? And how could you possibly make sure you’re having the *most* fun if you aren’t aware of all the other options for other fun you could potentially be having, right this second?
In a move which would surely dismay that eight-year-old version of me, I started to deliberately avoid seeking out counsel on things to do while traveling to new places. Lists were cheating, the equivalent of looking up the answers in the back of the book. I grew more and more accustomed to arriving in a city with no prior knowledge and just going for a walk; in fact, this has become one of my favorite activities.
Having discovered this new favorite activity, I decided, as usual, to overdose on it. “Go for a walk with limited prior knowledge” taken to the next level means it must be a good idea to go for a walk around a mountain with limited knowledge; specifically, Mont Blanc. Surely a one page, high level map without any topography would be sufficient? I have a baguette and some cheese, what could possibly go wrong?
On day three of the hike I made a series of increasingly comically bad route decisions which meant an extra two hours of bushwhacking on what was already the longest day of walking. While I did meet some very nice cows as a result, it meant that on the last day I was exhausted and reverted to being overly conservative in sticking to the known trail - but even that wasn’t as easy a task as it had been previously. After six hours I came to a trail junction at the foot of a glacier, and realized that the deviation I had considered taking earlier would have been both more spectacular and shorter. Any normal person would have planned sufficiently to know this ahead of time. I stood there kicking myself, staring up at the magnificent gorge where I could have spent the last few hours. In a moment of self-pity I caved and bought a tiny cup of artisanal Swiss gelato for six Swiss Francs (we all have our vices).
As I sat there, now high on delicious strawberry flavored sugar, I thought about what kind of planning ruins a trip and what kind enhances it. My former TechCrunch colleague MG Siegler had recently ranted about how movie trailers give away far too much about the actual movie, which I completely agree with. The worst kind of movie trailer shows you all the parts of the movie you’ll probably remember, and also tells how you’re going to feel when you see those parts in the actual film. By definition they’re the points with the most emotion, to the point where sometimes I think they’re included in the movie for the sole purpose of being fodder for the trailer.
Trailers, however, offer a useful analogy for cleaving apart the two types of planning. There is a type of planning that amounts to piecing together a highlight reel from other people’s trips and lives. As you go through the trip, you’ll have in the back of your mind that “this day is the day where I’m supposed to be feeling X, since that’s what I read in the guide where I got the idea for it”. This is not the good type of planning, since you’ve predetermined what you’re going to take from the trip - what your favorite things about it will be, how you’ll feel during different scenes, the type of people you expect to meet. You’ve watched your own trailer already, and it ruins the movie.
Planning that collects objective information about a place (Wikipedia is underrated as a travel guide) is the good type. Purchasing and carrying trail maps comes to mind as another example. Leaning on Foursquare and Yelp in the spur of the moment is also back in the acceptable camp, especially if they’re used for just the facts, ma’am.
Having now overdosed in both directions on the planning spectrum and found what I’ve determined to be a happy medium, I feel qualified to distill those experiences into a pithy, one liner trailer of a title and dole out the full experience to you, dear reader, as life advice. Hopefully the movie lived up to the hype.
 Something of a loose term here. MG mostly wrote about Apple; I mostly tried to keep the site up, with varying degrees of success.
 This may be more of a commentary on given movie itself rather than the trailer.