Sailing Across An Ocean Will Change Your Life — Here’s What To Know Before You Go

Life Writer
05.16.16 16 Comments

I remember the first conversation I ever had with Anna. We were sitting in a wood-paneled teacher’s lounge in Moscow, and everyone was telling stories about what brought them to Russia. I said that I was there because I’d studied the country’s history. Anna was there to travel. We both wanted to take the Trans-Mongolian Railway to Beijing when our contracts were up. It was one of those conversations that you have a million times. They seem inconsequential… until they don’t. That little bit of idle chit-chat changed the course of both our lives.

Six-months later, we were engaged and living in Phuket, Thailand (after having taken the Trans-Mongolian Railway as a couple). We’d found a brand new apartment building just outside of Phuket City — it was empty except for us. About two months before we arrived, a tsunami hit Thailand, devastating the local economy. We found ourselves living in a village brimming with out-of-work chefs from all the resorts in the area. Every night we’d stroll the main drag — inhaling the smells of frying chilis and fresh basil and listening to the buzz of passing tuk-tuks. Over and over we were treated to food from some of the best chefs in the country, who had little choice but to set up shop on the roadside to try and make ends meet. We shared Thai whiskey with them and they shared the secrets of the wok with us.

Trying to find a job in post-tsunami Thailand was tough. Many of the ex-pats had moved on. Tourism was at an all time low. We’d gone to support the economy, but didn’t have the money to loaf forever; teaching opportunities were scarce. After about two months without work, serendipity struck. While sitting at a burger bar in Chalong Bay, Anna and I were having one of those not-so-pleasant conversations about running out of money. We both had differing opinions about the way to move forward. Then I spotted a xeroxed 8×11 on the beer refrigerator next to the bar:




I jumped up and grabbed the flyer. I showed it to Anna. She looked it over and dropped it on the table. She looked at me like I’d gone mad.

“What exactly are we supposed to do with this?”

“Call him! Let’s get the job!” I said.

“I don’t know anything about sailing. I’ve never even been on a sailboat.”

“It’s not that hard! You can learn as you go.”

“It’s sailing across AN OCEAN.”

“I grew up on a boat, practically. It’ll be — ”

“No,” Anna said.

Her tone dealt an uppercut to the conversation. We ate our cheeseburgers and drank our Chang Beer in silence. The bartender took away our empty plates and brought back two more beers.

“So…?” I tried again after a few minutes.

“WHY…WOULD…I…CALL?” Anna said, exasperated. “They aren’t going to hire me to crew a sailboat when I’ve never sailed in my life!”

“Everyone learns to sail by actually sailing. It’s the boredom that you have most to worry about. The rest is easy!”

“What if there’s a storm? I have no idea how to handle that.”

“Hey, if something is going to happen, it’s going to happen out there…not sitting here.”

I’d just quoted Captain Ron to my future wife.


“Call him!”

Around The Web

UPROXX Travel Instagram