In every interesting life, there are moments of sheer absurdity. How, for example, do I find myself at age 24, in a Kentucky Fried Chicken drive-thru at 10pm at night, in rural Saga City Japan, on a bicycle, wearing a samurai mask (complete with bald head and top knot)? Absurd! How do I find myself embarking on a 21-day trek around the Annapurna mountains in Nepal – with no guide, no hiking experience, and no boots? (I did have tennis shoes, but still!) Absurd! How do find myself starting a teambuilding company (Dr. Clue Treasure Hunts) in 1995 with $500 in the bank and ZERO business experience? Absurd! Now, I’d love to proclaim that I’m “one of those guys” who likes to live on the edge, take life by the horns, blah, blah, blah. In fact, I’m just an ordinary guy who keeps stumbling into absurd situations which, at the time, sound like perfectly sane decisions, at least to me.

The Million Dollar Cowboy Bar in Jackson, Wyoming is most definitely an absurd place — one in a long line of ridiculous places I’ve been lucky enough to stumble upon in my journeys. When I walk into the bar, I’m struck by the sheer volume of western memorabilia lining the walls, from cowboy murals to animal mounts to authentic knobbled-pine architecture. What leaps to my attention, however, are the bar stools which are actual horse saddles. That’s right, you sit on a saddle while sipping your Miller Lite, swinging your legs playfully and occasionally jabbing your spurs into your mount and yelling “Hi-yo Silver!” Established in 1937, The Million Dollar Cowboy Bar is something of a Jackson institution. A posse of country stars got their start singing here, including Hank Williams Jr., Hoyt Axton, Tanya Tucker and Willie Nelson. Needless to say, there’s a steakhouse below the bar: the Million Dollar Cowboy Steakhouse.

In a perfect world, there would be a shady card game happening in the corner. A cowboy would push his way past the swinging doors and say, “I’m here to see a man about a horse.” A young cowpoke would throw a drink into his neighbor’s face, igniting a raucous (and picturesque) bar fight, with bodies flying through the window and landing in a horse trough. Sadly, nothing particularly absurd happens to me while I’m at the bar. I have a drink, soak in the atmosphere, strike up a conversation with the bartender. That’s about it. Is the bar a little cheesy, a little over-the-top? Absolutely! But I love it! The great thing about a place like this is, for all its attempts to recapture the old west, it still feels authentic somehow. Wyoming is cowboy country after all. Those folks a few saddles down from me, decked out in cowboy hats, boots and over-sized belt buckles, aren’t necessarily movie extras here for the next Quentin Tarantino movie; they’re just locals, enjoying libations in a comfortable, neighborhood tavern. The fact that a tenderfoot like me from the San Francisco suburbs is sitting here in this crazy cowboy setting is absolutely absurd, but the folks around me most certainly are not, and that’s what makes it special.

(There’s a fine line between absurdity and craziness. It’s absurd to bungee jump. It’s absurd to sky dive. It’s absurd to travel alone to someplace like India (at age 25) – but that absurdity is more about perceived risk than actual risk. All of those activities are actually pretty safe as long as you do your research and your due diligence. Crazy is when you do something that is out-and-out dangerous, like following a tout at the train station to his cousin’s premium hotel. Except even that can work out sometimes, like the time I found the most amazing place to stay, overlooking a lake in rural Turkey, by following a train station tout. In other words, you never know which decisions will kill you, and which ones will lead to an indelible memory. In short, trust your head, trust your gut, and remember: what doesn’t kill you makes you interesting.)