The Things That Go Wrong Make the Best Memories

A lesson from life, adventure, and travel.

I’m not sure if something went terribly wrong here (hopefully not), but I liked the photo. 📷

I had a guilty secret about my quest to go to every country in the world: much of it was boring. 

A great deal of time was spent in transit. Frequent backtracking became a necessary evil, but it was never my favorite activity. Moving forward and making progress felt great. Turning around and going back the way I came, over and over again, not so much. 

I also spent a lot of time sitting around.

Consider a typical twelve-hour bus ride through Albania. Such an adventure does contain a few notable moments: in my case there was the bottle of vodka passed around the bus, right on cue. There was the border check when I held everyone up, being the only traveler with a U.S. passport. And then there were the other eleven hours. 

That’s how so much of the quest went: pockets of adventure interspersed in hours upon hours and day after day of routine. 

I didn’t actually mind it most of the time. I learned that I thrive on routine. 

But just as I can still remember the vodka bottle and the customs interrogation of that bus ride (and almost nothing else) from a trip long ago, that’s how I recall most other parts of the eleven-year process. Selectively, in other words.

Much of it was boring, uneventful, and repetitive. 

What I remember far more than the repetition are all the things that didn’t go well.  In an earlier book, The Happiness of Pursuit, I went so far as to catalog a number of what I called “misadventures.”

One time I drove off the road in Italy, damaging my rental car. Another time, I was deported in the middle of the night from Eritrea, leading to a vigorous online debate as to whether my visit “counted” due to its lack of a passport stamp.

It wasn’t that any of those things were particularly pleasant at the time—but they also aren’t terribly unpleasant to remember now. I began to feel a sense of pride in making mistakes, then recovering.

It was as if I were testing limits. I’d show up perilously late to the airport. I’d arrive in cities without a reservation or a plan. Sometimes I’d even arrive in countries without a visa—which I wouldn’t recommend, but I was only deported that one time. 

I think it was Gretchen Rubin who first said, “The things that go wrong often make the best memories.”

The concept applies to a lot more than just travel. Many times when something has gone wrong in my life, I often end up in a better place on the other side of it. Then I look back and think, wow, that was a tough challenge! But here I am, stronger for it, so I’m grateful. 

(Note that Gretchen uses the qualifier “often,” meaning that not everything that goes wrong makes for a great memory. I think that’s important to note.)

When we encounter obstacles and overcome them, we often find ourselves in a better position, looking back with a mixture of pride and amazement. Something went wrong—and it turned out okay!

Consider your own experiences. How often have your most compelling stories stemmed from situations where everything went according to plan? It's rare, right?

The narratives that captivate us, the ones we share with enthusiasm, typically involve unexpected turns and a sense of rising to the challenge. 

It’s not that you should try to fail, or deliberately seek out misadventures. It’s that you should regularly place yourself in situations in which something could go wrong. 

If you find your life becoming routine or monotonous, ask yourself—what am I risking? When was the last time I engaged in an activity that made me slightly nervous? 

Or maybe: How am I allowing myself to fail, or at least get into trouble somehow? 

(If you're struggling to remember, it may be a sign that you're playing it too safe.) 🫣

See also

Adventure Is Worthwhile In Itself