I quit my job to sail around the world and so should you

‘I don’t want to be stuck in a cubicle working when I could be sailing to some unknown land’


After Andrew Stephens graduated college, he was faced with a tedious future working in finance – so he quit, bought a boat and set off to sail around the world. A year and 10,000 miles later, he's still going. When we spoke yesterday, he was anchored off the coast of Singapore (Burma next, followed by India, the Seychelles and Africa). Here he explains why ditching the nine to five was the best decision he ever made.

How did you start on your journey?

I was working in finance. I found the whole industry to be so unethical. The company I was working for offered me this huge bonus and wanted me to sign a contract. I walked in the next day and said: "I'm going to sail the world instead." They looked so shocked. They didn't believe me and I didn't believe me either! But that's what I told them, and now I'm doing it. It wasn't a right fit for me.

What was day one of sailing away like?

It was absolutely frightening! I hadn't had that much experience sailing. I taught myself, I never had a great mentor or anything. I had never had an overnight experience, I would always anchor. So when I pointed the bow out west, I was terrified. When the sun sets it's a whole new world sailing at nighttime.

Tell me about your journey.

I left from Seattle to Hawaii. And then from Hawaii, I went 2000 miles through Micronesia. Nobody knows about it! Thousands of miles of uncut Polynesian culture. It's like what you see in the movies – people wearing grass skirts. It's another world. I spent six months in the Pacific. I just left Borneo and went through the South China Sea. Now I'm close to mainland Malaysia. Next I'm headed to Burma, and I'll jump onto Sri Lanka, then India, the Seychelles, and then Africa. Depending on the weather, maybe Madagascar. With sailing there's always a hurricane season that's active in the northern or southern hemisphere so you're trying to switch hemispheres. So I want to leave Africa and sail across the Atlantic in our springtime.

What's been the highlight so far?

This island I visited in Micronesia called Woleai, it was utopia. It had no money, no internet, no power. Everybody worked in this big socialist community. It was amazing – the people were beautiful and friendly. I had never experienced anything like that. Seeing that made me think that this whole trip had paid for itself. It was all worth it just to visit that island, this spec of earth in the middle of the Pacific.

Otherwise just sitting out on the deck in the sunset, hundreds of miles from anywhere. It's one of those surreal moments, but it happens every day. You can't believe you're doing it.

How did your friends and family react?

Nobody actually believed me! I told them two years before I even left. It was two weeks after I graduated that I was telling people – I'm leaving next week. I held off on telling them I was sailing the world, just in case I never even made it to California and think: "Hey man, this is not for me!" So I just said I'm going to Hawaii. My family has been really supportive – of course my mom is constantly worried. Messages from random people are incredible – when you're out there and it gets a little shitty, someone saying: "Hey, what you're doing is amazing," I really appreciate that.

How does it feel to leave the daily grind behind you?

To be honest, sometimes those societal pressures are still with me. You open up Facebook and see a stream of people getting married, having kids and all that. Hear you are with no shirt on, sitting on a beach, thinking about getting to the next island. You realize: "Man, I've got to get my shit together! Get a job or something!"

Your situation definitely seems better.

Yeah, I had this epiphany – I'm starting to appreciate so much more what I have, living in the present moment. This sounds sappy so bear with me, but when I was in Seattle, you just get caught up in the next car, the next job, the next house. It's part of the culture. You have to do that. It's like living in this subdued competition. I noticed after being away for a year on the boat, all that is just gone. I don't need anything new – what I have is fine. I'm not looking for that next job, I'm just living my life. As long as I have food, I'm happy. I was sitting on my boat watching the sunset yesterday and thinking: "Right now, in this moment, it's pretty perfect." It's one of those things you never notice when you're caught up in the 9 to 5. And it's alright – when I go back I have no qualms about working for the Man, but I'm definitely going to be happier with what I've got.

I'm not stopping just yet. I don't want to be stuck in a cubicle working while my boat is waiting in the dock and I could be sailing to some unknown land.

What do you miss?

I miss showers. Here on a boat, you're so filthy and dirty all the time. When I get to a place and find a shower, it's the greatest. You can't take a proper shower for weeks on the boat – the clean water's too scarce. I can shower or drink water for a week.

Andy says if you have any questions for him or are looking for advice on sailing around the world, go ahead and contact him here.