There’s a game I play with myself when I want to explore a city but don’t have a particular destination in mind.

I start walking and I follow the signals and signs provided along the way. I turn left and cross the street because the little glowing walking man indicates that I should. If I encounter an intersection without stoplights, I keep going straight, but at the next such intersection I go right, and at the next I turn left, and continue to circulate between the options at each new opportunity. When I see a coffee shop I’d like to try, or a museum I’d like to explore, or a shop I’d like to peruse, or a park where I’d like to sit and write for a bit, I pull myself from the game, starting again when I’m back on the street.

This is a great way to find new areas of a familiar city or to push yourself out the door in an unfamiliar place. It’s easy to become overwhelmed by options, and this game gives you permission to just go. To discover without planning. To allow chance and circumstance to take the wheel for a while.

It also allows you to get lost. One of the more valuable ways to learn a city, to learn not just the colors and smells and pace and noises, but also how to read them, analyze them, and use them to get where you want to go, is to get lost and then figure out how to get back to your starting position.

It’s difficult to achieve true randomness. Generally when we head off in a ‘random’ direction, what we’re really doing is taking one side street from our usual route to a familiar part of town, or heading in the exact opposite direction from our default path, avoiding anything familiar at all. These can both be useful methods, but the former lacks the potential for extreme new-ness, while the latter eliminates your ability to see the familiar from a different perspective: a landmark from your usual route viewed from across the street, for example.

After years of playing this game, I’ve found that the feeling of being ‘lost’ slowly becomes less of a scary jump into the unknown, and more an intentional reaching out into the world, looking for novel stimuli and finding it. Bringing it home to study in private. Wondering if it’s worth working into your normal routine. Wondering if that normal routine should be shifted in some meaningful way.

That may mean identifying a better way to work. It may mean finding a coffee shop you like better than the one you usually visit. Or it may mean confirming that the commute you currently make and coffee you currently drink are still the best available options, based on your priorities for both.

Consider how getting lost can be about more than just learning your environment. How it can be a means of pulling yourself out of your norms, habits, self-perceptions, and into a space where you’re less certain and more able to explore. More capable of taking a wrong turn and not worrying about it. More able to filter your options and wonder whether this job, this lifestyle, this relationship, this responsibility, this goal, this whatever, is actually what’s best for you and your happiness.

Upon returning ‘home’ to your norm from some great adventure, whether external or internal, you might realize that you’re more at home elsewhere. It could be that getting lost is the only way to find your way to a home, a more ideal life, you didn’t even know existed.

Update: April 19, 2017

I love playing this game. I still do this, and it still confuses the hell out of people when I tell them that I found someplace by walking past it, and that I was in that part of town because I was following the stoplights and pedestrian signs.

Especially in a time in which our lives are so well curated, and our options so immensely filtered through apps and five-star reviews, introducing what amounts of a randomly drawn Chance card, which may be valuable or worthless, can be like opening a mystery gift.