“Not all those who wander are lost.”
J.R.R. Tolkien

If you are looking for a way to spice up your next date night, I have a great suggestion. It is fun. It is an exercise that helps to eliminate expectations and is fantastic practice for letting go of control. You can do this with almost zero effort or planning. In fact, not planning is one of the basic requirements in order for this to work.

So what is it?

Getting lost.

Go through your own personal rolodex of memories. Which ones stick out to you? What stories do you find yourself telling time and again? Is it the story about the Friday night when you researched a restaurant online, made a reservation, showed up on time, had a pleasant meal and then went home?


Some of my favorite memories, and almost all of my go-to traveling stories, stem from times when things went to absolute shit. When I was lost, or a bus broke down or a boat ride was cancelled or I was stranded with friends in a small town in the middle of nowhere.

I do not tell people the story about my overnight bus ride from Chiang-Mai to Bangkok that left on time, met all of it’s scheduled stops and arrived at it’s destination.

Who would?

No I would prefer to tell the story of my bus ride from Cusco, Peru to Lima, Peru. The bus broke down several times. There was one running start where we had to catch up to the bus and hop on. After the bus broke down for the fifth time, we had to pile in the back of a closed semi-trailer for almost 90 minutes:

One visit to the national police office, two buses and fifteen hours later we arrived in Lima. The trip took more than 36 hours in total. It was the worst bus ride of my life. But it is also the most memorable. I will always remember being packed in the back of a semi-truck in complete darkness for two hours. I can still remember looking up at the Andes as myself and two French travelers sat sharing cigarettes and coffee while fourteen Peruvian men argued about how to fix our bus. I finally got to ride in the back of a semi-trailer.

The average person’s life, on the whole, tends to be rather regulated. It is routines and work and pre-arranged get-togethers. Most of the time, we organize our life to avoid surprises. Which is why stories about random encounters or getting lost or having things go hilariously wrong stand out. They are a break from the mundane.

So why not get lost?

Why not purposefully put yourself into a situation where you do not know where you are or what you will do next? If you are on vacation in a new place, this is easy.

Traveling, essentially, is getting lost.

On your next trip, do yourself a favor and ditch the guide. Ask around about neighborhoods that are safe and pleasant to walk in and go wander. Do not research restaurants or things to do. Just go and see what you find.

You can get lost close to home as well. Pick a neighborhood you know nothing about and go for a walk. Or go ride bikes. For all my homies in Wisconsin who are thinking that it is often too cold for either of those activities, I say this. Bundle up. Or drive. Or wait until spring. If you know your hometown too well and cannot think of a neighborhood that would surprise you, go for a drive. Get on the open road and start taking random turns as often as you would like.

I feel compelled to say that getting lost has to be done with reason. Do not do this on a night when you do not want to walk a lot. Do not do this is in neighborhoods that are known to be dangerous. If you start to wander into a neighborhood that may not be a bad neighborhood but has the familiar trappings of a bad neighborhood; gun store, liquor store, gun store, bail bondsmen; turn around.

I am suggesting you get lost for a few hours, not forever.

All disclaimers aside, here is why getting lost on purpose is a good idea:

1) Firstly, and most importantly, you will learn to roll with things.

Getting lost is kind of fun. Hilariously strange stories come from it. I once got lost in Parque Arvi, a national park outside of Medellin, Colombia. You have to ride a cable car over the city to get to the park. The cable cars stop at 6:00PM. We got back to the station at 7PM. A misinterpreted message to two Colombian friends put us on the radar of the National Police, who thought we were still lost in the park. While drinking beers at a tienda, waiting for the next bus, we noticed an increase in police activity. We were the cause of the activity.

A short explanation of the mistake…

Led us to befriending a local Colombian family, who invited us to their home for a bonfire….

And then allowed us to spend the night. A sunrise shot…

Give it a solid two hours and see what happens. Trust yourself, you are smart. You, better than anyone, know what you like. Look for that. You might be amazed at how well things turn out. At the very least, you be reminded that at the end of the day, regardless of your plan, things tend to usually turn out all right.

2) All expectations are out the window.

There is a famous saying, “Plans are invitation to disappointment.”

If you are lost, everything becomes a weird, pleasant surprise.

If you go to someplace you don’t like, just leave. You’ll likely laugh about it later. I do not mean to say to purposely search for a bad time. If you find someplace you love, it is an even better story. But by starting with no plan or expectations, you are immediately eliminating the opportunity for any expectations. You have absolutely zero chance to be disappointed because you have zero idea where you are or what you will do.

In college, my friends and I were consistently amused at how our random nights out seemed to turn out better than our planned get-togethers. The interesting thing was that we often went to similar places with similar groups of people. So what was the difference? On the random nights out, we had no expectations. Things would sort of just happen. By having no plan, and no expectations, we became more open. This openness did not create more opportunities for us. It simply made us more aware of them.

3) It pushes you outside of your comfort zone.

Getting lost is like one big trust fall. Feeling lost is not a natural feeling. We like knowing where we are. We like knowing where we are going. The unknown, as much as anything, scares us.

If you really try to get lost, phones should not be used. You are not lost if you are looking at your GPS location on your iPhone with a series of Yelp reviews alongside. You will have to ask people for directions or recommendations. You will have to use your intuition a bit.

4) It is good training for L-I-F-E.

While we all would like to think that we are in control, in reality we are not. The world operates largely at random. Our lives and the worlds that we create for ourselves are thin pieces of glass that can shatter at any point in time. One thing happens and BAM, the whole picture changes. Practicing letting go of control and learning to adapt to life as it comes to you is fantastic practice for when things do go wrong and we are left to pick up the pieces.

5) You will wake the fuck up.

Apologies for the language, but it adds a certain level of effect. I try to limit my indulgences.

I am as guilty of the zombie walk as anyone. No phone means no GPS means you will actually have to look at street signs and remember landmarks.

No online reviews means that you will need to pop your head in somewhere and follow your gut. You will have to talk to other people. Most likely ones you don’t know. You will be forced to actually look at random strangers and assess who seems like a good person to ask for recommendations. Learn to smile and trust people. Most people are kind and willing to help.

Life is not always meant to be structured. The world we live in is random. Who we meet, how we meet them, where we end up.

While plans may be comforting, and even helpful, they almost always end up changing. Try wingin’ it. Take life as it comes at you, on it’s terms, not yours.

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