This Guy Went Around The World In 80 Days The First Time He Travelled 

This Guy Went Around The World In 80 Days The First Time He Travelled 

The death of a close friend rocked Chris Sypolt’s world. So, he did what any logical 44-year-old would do and set out on an an 80-day round-the-world trip. It was the first time he’d ever left the United States. This is what he learnt.

I first learnt of Chris’ story through the ‘How To Travel Internationally For The First Time’ article. So many people never do that, so I was curious how he got the motivation and, well, the balls to do it. Turns out, he’s an interesting guy with an interesting experience, so I asked him to share it with you.

IndefinitelyWild: Why did it take you 44 years to leave the country?

Chris Sypolt: First, I spent 2000 to 2013 at a small dotcom where I was the sole technical guy. I couldn’t be unreachable if the system went down. Second, I love flying, but I hate aeroplanes. Anything over four hours and my legs get ridiculously restless. Third, I’ve finally come to grips and learned to admit this publicly — I am a ridiculously picky eater.

IW: How the hell did you decide to do a round-the-world trip for your first time?

CS: 2012 sucked for me. My best friend was diagnosed with colon cancer in January. She got worse, then she had surgery, then she got better and then she got worse again. She passed away before the end of the year; it was devastating.

At the same time, my company was transitioning to a new financial model. It meant 80 to 90 hour weeks and a new email was arriving, on average, once every 45 seconds around the clock. It was exhausting and, by early January, it was clear that I was simply not capable of upholding the standards that I’d set during the previous 13 years. So I decided to transition out.

My original plan was to head to Hawaii for two weeks, then come back to Seattle and put my life back together. But, during a liquid lunch with my soon-to-be-former business partner, he suggested I take the time to do some real travel. I started looking at maps.

New Zealand seemed manageable, provided that I could talk my Doc into some Ambien. Then I realised that if I stopped there, I would be looking at a long-arse flight back to Seattle. Australia, with its beautiful women and accents was right next door, flight-wise. So I added Australia. But, there was still that flight back to America, so I decided to add Japan too.

At this point in the planning, things kind of took on their own momentum. I didn’t need to be back in Seattle for anything and I found first class ticket from Tokyo to London that I justified because THERE IS A BAR ON THE AEROPLANE. It was downhill from there. It made no sense to head back the way I came, so I decided to hop through Iceland, then to the East Coast, stop in Pittsburgh and eventually head back home.

I was an emotional disaster and I needed to get away from things, so I just decided to head west and inertia took over from there.

IW: Describe the person you were before versus the person you were when you came back.

CS: Before, I was angry and bitter and closed to the world. After, I was grateful I’d had the chance to do something so amazing.

IW: At what point during the trip did you realise your whole life was going to be changed forever?

CS: Day three. I was on a snorkel cruise in Maui and started talking to the captain. I told him about my trip plans and his reaction was, “Ho-ly Shit!” It was the purity of his reaction that did it for me. I’d been given a great gift to be in a position to do something like this. He let me drive the boat for a while.

It helped that, that night, I found a source of weed and spent a lot of time sitting in the dark, very high, looking at the stars.

Yes, they really do sell used panties.

IW: Walk us through the trip.

CS: The itinerary, as originally booked, was: Seattle – Kaanapali – Waikoloa – Waikiki – Auckland – Brisbane – Cairns – Melbourne – Canberra – Sydney – Tokyo – Osaka – London – Paris – Normandy – Bastogne – Amsterdam – Reykjavik – Boston – NYC – Philadelphia – DC – Pittsburgh – Seattle.

I ended up cancelling the Normandy and Bastogne portions, even though I’m a WWII nerd. By then, I’d visited Pearl Harbour, seen MacArthur’s headquarters in Brisbane, swum in the Coral Sea, prayed at the Yasukuni War Memorial, toured Churchill’s wartime bunker and spent a day at Bletchley Park, where Alan Turing broke Enigma while, as a sideline, inventing the computer. I decided I was tired of chasing death and destruction during the Tower of London tour as they described yet another execution. So Bruges replaced Normandy and Bastogne.

What was the trip like? I was terrified at first. At one point, I was actively discussing flying back to Seattle from Honolulu when a friend sent me this note:

“Dear Sypolt: If you need to change your flight to follow Australia and New Zealand, and then you take it, I understand. But God help me, if you don’t go to Oz, and satisfy your accent fetish, I am going to punch you in the dick when you get home.”

That got me over the hump. I was born in 1969 and, when Grease came out in the late ’70s, Olivia Newton-John’s accent happened at just the right time for a prepubescent Sypolt. I wanted to hear it, all the time. Is this a stupid reason to travel outside the US? Probably, but it worked.

Once I’d built up some inertia, things became really easy. I could find my way and get from place to place thanks to the apparent omniscience of Google Maps on my phone. And I revelled in my newfound freedom from schedules. I ate when I was hungry, slept when I was tired and everything was a new experience.

IW: What was the most surprising thing that happened to you?

CS: The twelve-year old in me is screaming to talk about toilet technology in Japan. It makes something that we all do, on a regular basis, into a wonderful experience. But I had been prepared for what to expect there.

Instead of surprising, I think more in terms of things I delighted in: The similarities between Seattle and Auckland; standing in the same room that MacArthur once strode; hugging a koala; snorkelling the Great Barrier Reef and pondering evolution; dealing with hangovers after drinking with Australians; watching baseball in Japan; the smell of trees in Kyoto; the horror I felt in Hiroshima; the sense of permanence you get from really big buildings in London; the decadence of ordering a third croissant in Paris; the first slice of east coast pizza in Boston. I could try to describe those feelings, but I’d fall short.

IW: What was your favourite place?

CS: I’m torn between Bruges and Kyoto.

Bruges was a late addition to the itinerary. Everything there is compact and old. My hotel was built in the 1400s, but had excellent WiFi. Biking the entire area, seeing actual windmills, feeding the ducks in canals; it was more than I ever expected out of life. Plus, I found a restaurant that serves steaks on an actual grill, so the meat stays warm.

In Kyoto, a young couple volunteered to take me to three of the buddhist temples. The husband is actually a buddhist priest, so the last place we went was actually the temple he studied at. The master of that temple invited us in and spent and hour or two with us. I was expecting a dour, Yoda-like person full of solemn life wisdom. He spoke no English, I speak no Japanese. But, he had seen Westerns. Like, all the Westerns. He would talk about the scenes he liked, then make a “Pew, pew, pew” noise with the most gigantic grin on his face and a belly laugh that rumbled throughout the building. I assumed that he had achieve enlightenment, so his reaction and his effervescence while I was still in mourning for my friend was encouraging.

IW: How does America feel now?

CS: I’ve come to the conclusion that, like some tropical tourist locations, America is as much a state of mind as it is a place on a map. We aspire to high ideals, then fail at them on a regular basis. But, for all of our faults (and there are many!), it is the one place in my admittedly limited experience where reevaluation and reinvention is viewed as a virtue.

I also learned that we are not appreciably different from the rest of the world. Despite my ridiculously bad French (three years in high school), I was somehow able to make croissants and coffee appear on my first day in Paris. That might not seem like a major accomplishment to most people, but it was for me. Three days later, the waiter had my order already waiting as I sat down. I was being welcomed, and in the last place I expected that to happen.

You can’t figure out your place in the world until you’ve actually gone out and seen it. Leaving the country of your birth may seem scary. Cancer is scary, getting on an aeroplane for eight hours is not.

IW: What did your friends and family think?

CS: My mum was terrified. She assumed that I would be beset by gangs and ruffians and wind up bleeding and broken in a gutter in Amsterdam. When I got there, I asked for a hit of something and sat in my hotel room watching ice melt for four hours. It was AWESOME.

The vast majority of my friends were jealous. Not in a bad way, which is an important distinction. There was an implied responsibility from that, to do and experience for my friends what they would likely not do and experience for themselves.

Chris ended up writing a book about the experience. He was reluctant to share it, but I insisted.