Travel stories, pith helmets and proper adventuring

Why every great travel story needs an "oh shit moment"

Every great travel story needs an “oh shit moment.” That moment in time when you wished you never came, when the whole idea just seemed like the dumbest thing ever. Without it, you might have had a great trip, but you will never have a great story.

Cars have an “oh shit handle.” Travel stories should have an “oh shit moment.”

Now, the trick to a good “oh shit moment” is it has to be spontaneous. It can’t be orchestrated or preplanned. It has to happen naturally. But at the same time, you don’t want to be a foolish idiot inviting bad things to happen.

You must be open to an “oh shit moment,” but not expecting one. Otherwise, it’s not really an “oh shit moment.” Now is it?

That puts your adventure on a delicate balance. Therein lies a paradox. Be prepared, be prudent, be safe, but also be a little carefree when the situation allowed. My late friend Neil Zawicki had a term for this. He called it “crackerjack adventuring.”

We published a magazine in college — four issues — called Jaunt: The Journal of the Crackerjack Adventurer. Neil is pictured above wearing a pith helmet typing on a keyboard while speaking on the phone, a very common look for a crackerjack adventuring reporter, indeed.

At the time, we always had difficulty explaining what a crackerjack adventurer meant, especially to advertisers. Reckless but not stupid. Ambitious but ill-equipped. Prepared but haphazard. Well-trained but clumsy. No wonder we didn’t last long.

Neil imagined it as a Brit named Gaston Dilmore and wrote a column in his persona. He had a fine English accent, smoked a pipe and adventured over land or by sea while everything around him was falling apart. Maybe the boat was taking on water or the wheels on his truck were busted, while his clothes tore apart at the seams and he suffered from dysentery. Kind of a poser, who looked great and sounded great, but in reality was a little less capable than people thought.

Maybe it’s not until now that I could properly define a “crackerjack adventurer,” though it’s still not easy. Maybe it’s that thirst for “oh shit moments.” As if that makes it any clearer.

Neil was the one who got me into sailing. He talked it up so much in college that when I got back to California, I learned to sail and bought a Catalina 22.

In sailing there is a common phrase: Calm seas never made a good sailor. In other words, you need some “oh shit moments” if you’re ever going to learn anything valuable. You need some “oh shit moments” in life generally, just not too many.

Unfortunately, in a lot of the “oh shit moments” in my life, I didn’t have the sense to take a picture. Here’s one “oh shit moment” caught on camera on a ledge while climbing Longs Peak in Colorado.

The terrain was steep and bouldery. Someone was airlifted out a few hours earlier. I climbed over a ledge and held onto a flat rock that sloped downward. I began to slide a little, maybe a few inches. It felt like more, but my heart skipped a beat. I held on and pulled myself up, exhausted. “Oh shit,” I thought. Can you see it on my face?

The problem with this theory is you inevitably want to go searching for “oh shit moments.” But you can’t go about adventuring with a cavalier attitude. You are liable to get yourself hurt.

You should be prepared. Plan ahead. Do your homework. But if you want to have a true adventure, you can’t go about planning too much ahead of time.

That’s why I still like to keep a loose itinerary no matter where I go. I want to be open to new adventures, something I learned about from meeting someone on the plane or in a bar, some place that a local told me about that I had to visit.

Maybe it will be a great adventure, filled with new experiences, meeting new people. And it might be a great trip. But if the taxi got a flat tire, or the raft overturned, or you got stranded somewhere, or God forbid you thought you might die, now that would make a great story.

You’ve just got to go about it naturally. Trust me, it will happen.

Thanks for reading.

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