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How We Made the Decision to Quit Our Jobs to Travel and Sail the World

“Twenty years from now you will be more disappointed by the things that you didn't do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.”—Mark Twain

A few days ago I announced that Garrett and I quit our jobs to be able to travel and sail around the world full-time. I’m here today to talk about how we came up with this plan almost five years ago.

We were walking home from a yoga class, bracing ourselves against the fog rolling in over the city. It was a November evening, I think—though without four distinct seasons here, I never really know. It was 2014, and Garrett and I had lived in San Francisco for a year.

Earlier in the week Garrett came home from work with an idea.

“Kadecia and her wife did this thing,” he said, referring to his coworker, “they each wrote down the 5 most important things to them individually and then talked through them together. We should do that.”

I readily agreed.

We took the next few days to mull over what was really important to each of us, and on that chilly evening walk home from yoga, we started to discuss what each of those things were, and what we were going to do about them.

These were my five: Relationships, Community, Travel, Health, and Creativity

These were Garrett’s: Water, Freedom, Stability, Celebration, and Relationships

From that conversation we learned two things big about each other: I really wanted to travel and Garrett really wanted to get out on the water. And so, our dream was born: we were going to travel the world by boat.

At first we imagined traveling by a motorized boat, like a Grand Banks 32. But then we started to calculate the cost of fuel and well…we decided that we needed to learn how to sail.

We jumped to it. Because we believe in the power of saying things out loud, we started to tell a few close family and friends about our dream. Nick Parham and Jimmy Martin, two men who helped me so much in finding a career when I first moved to San Francisco, helped me once again by introducing us to Marc and Doreen, friends of theirs that had spent five years circumnavigating the globe.

We met Marc and Doreen for tea one afternoon in the settee of their catamaran in Sausalito’s Galilee Harbor and asked them about their experiences traveling the world by boat. Their words only made our dreams bigger. Marc connected Garrett with a non-profit sailing organization in San Francisco, and a week later Garrett was leaving work early on Tuesdays to volunteer with them as crew.

Later, a couple of other friends of ours, Lauren and Paul, connected Garrett to their friend’s cousin Nick upon hearing our plans. Nick was about to do something similar to what we wanted—he was quitting his job and leaving in a year or so to cross the Pacific. Garrett met Nick for coffee one afternoon, a list of handwritten questions in tow, and a quick friendship ensued. We started sailing with Nick on his boat Wedimynd shortly after.

It seemed the more we spoke about our dream, the more it was facilitated. We had to be careful, of course, and not scream it from the rooftops because, well, we needed to keep our jobs. And we still had so much to learn—and save—to make it all come true.

In my next post, I’ll share how we saved, bought a boat, saved some more, and prepared to travel and sail around the world. But for now, I’d like to thank a few people. Kadecia, wherever you are, thank you for inspiring Garrett and I to communicate in a way that so richly changed our lives. Nick and Jim, thank you for connecting us to the people in the Bay Area who have been instrumental to our success—in our careers and in our dreams. Lauren and Paul, thank you for introducing us to Nick (AKA Nico). We swear we’ll all go sailing together one day. Nico, thank you for leading the way and having such a positive influence on our sailing experience. And to all of our family and friends who have known about our plan, kept it quiet, and supported us from the sidelines, thank you for believing in us.

Before I go, let me encourage you to write down the five things you hold most important in life right now. And then ask yourself, are you making room for them? If you’re not, how will you?