A conversation with my girlfriend has changed my life forever

My girlfriend and I have been together for three years. We’ve talked a great deal over that time, but it’s a conversation we had at the end of last year that’s really made me think. And it’s made me rethink my entire life.<br><br>We’re both freelancers in creative fields who often go weeks or months without any work, so we’d been discussing what to do. The conversation started in our kitchen. We’d had a couple of bottles of wine and were exploring crazy ideas. <br><br>My girlfriend said, “If you had a million dollars, what would you do with it?”<br><br>I didn’t even need to think about it. “I’d buy a small island in the Caribbean, a small house, a boat and spend my days sailing and fishing.”<br><br>My girlfriend said, “That sounds nice. But you’ve always told me you wanted to travel.”<br><br>I agreed. I’ve always wanted to travel. And my girlfriend and I have done a lot of it, but we could never really afford to travel long term. <br><br>Then my girlfriend said, “Imagine if you could, though. Now imagine you had the means to do it, but not the motivation. You have the means but at the same time you don’t really want to do it.”<br><br>I replied, “That would be sad. I guess I’ll just have to live that experience vicariously through other people.”<br><br>Then my girlfriend said, “You don’t have to.”<br><br>I asked her what she meant. <br><br>*What do you mean?*<br><br>She replied, “Anybody can do it. All you have to do is sell your house, buy a boat and set sail.”<br><br>*That sounds ridiculous. Anybody can’t do it.*<br><br>My girlfriend said, “Well, I suppose they can’t, but we can.”<br><br>*How?*<br><br>My girlfriend said, “We both have jobs where we can work remotely. And we have a small house. We can put our entire lives into a storage facility if we want to. We could afford to do it. How? By working remotely on the boat.”<br><br>That conversation went on for a while. Neither of us believed what we were talking about, but we both knew deep down it was possible. And in the end, we agreed. We could afford to buy a sailboat and live on it while sailing around Central America and the Caribbean.<br><br>We also agreed on one more thing. Neither of us would ever have the motivation to do it.<br><br>I asked, “How do you get the motivation to live on a sailboat for several years?”<br><br>My girlfriend replied, “Exactly how do you get the motivation? You just do it. You can’t think about it. If you think about it you’ll chicken out. You just have to go out and do it.”<br><br>We’d had too much to drink that night, so we went to bed and forgot about the conversation.<br><br>It took about a month for that conversation to sink in and for us to realise we’d been serious. So we made a list. <br><br>That list included everything we’d have to do to live on a boat. It’s a lot. We needed training in sailing. Sailing is a highly technical skill. There’s a lot to learn, and it’s not something you can do on your own. And it’s expensive. Sailing lessons aren’t cheap, especially the longer, more advanced courses. But we could afford it. We could also afford to buy a sailboat, and we’d done our research. We knew what kind of sailboat we needed, and we knew we could afford it. But we couldn’t afford the marina fees. <br><br>We were going to have to keep our house. It would be too expensive to live on a boat in a marina. The marina fees would be more than our current rent, especially in San Francisco. It would be way more expensive to live on a boat here than in our current house. We were going to have to keep the house if we wanted to live on a boat.<br><br>We’d already decided on the area we wanted to sail in. The San Francisco Bay is perfect for learning. There is plenty of room to sail, and if you wanted to learn, there are plenty of training courses available, from beginner courses to advanced courses for long distance sailing. <br><br>Once we’d learned, we’d have to figure out how to get the boat to where we’d actually be sailing in - Mexico and Central America. <br><br>Then there’s the boat itself. We needed to find a good sailboat. We were certain that we could afford one with everything built into it. That would save us a lot of hassle. But how do you find a good sailboat in San Francisco? Neither of us knew anything about boats at that time, other than the fact that you needed training. But there’s another thing we’d figured out. There’s a network of people who live on boats. There are marinas everywhere. If you’re living in a marina, you’re in walking distance to thousands of people in the same situation. There are also sailing and boat clubs. And there are sailing schools and training courses. We could ask our instructors. They’d been sailing for years, and maybe they’d know someone selling a boat.<br><br>We’d figured a lot of things out. We’d figured out what needed to be done and how we’d do it. And we’d figured out that we could afford it. But we still didn’t have the motivation. Sure, we wanted to sail the Caribbean and we wanted to live on a boat, but we didn’t have the motivation to actually do it. It was too big of a leap. It was scary and it was a risk. What if we did it and didn’t enjoy it? What if we got bored? We could afford to do it, but what if it didn’t work out? And what if we lost money? We’d have to keep the house and rent it out. We’d have to live on a boat while paying a mortgage on a house. But what if it all worked out? What if we enjoyed it? What if we had the time of our lives? We just didn’t know, but at that time neither of us was willing to take the risk.<br><br>It was a few weeks later that I was on the BART going home from work when I saw it. An advert on the wall of the train car. The headline said, “Volunteer abroad. Travel the world.” <br><br>The advert was for a website, but I didn’t take note of it. Later, I went to my usual job search websites and looked for volunteer work abroad. I scrolled through a few. You can volunteer for anything and everything. There’s animal shelters, conversation projects, schools, hostels, anything. I looked at a lot until I found it. A sailing trip across the Atlantic. <br><br>I couldn’t believe it. There were a few - several different trips doing exactly that - sailing across the Atlantic. I’d always wanted to do that, but at the same time never wanted to do it that much. I didn’t have the motivation or the courage to do it, but there it was - a volunteer opportunity to sail across the Atlantic.<br><br>I scrolled through all of them before picking the one I was most interested in. It was from a person. They weren’t from any kind of organisation - just a person doing it on their own and looking for crew. They were taking their boat across the Atlantic and back and were looking for crew along the way. <br><br>I read the advert carefully. It said they had already set sail, and they’d left from Texas. Now they were in Puerto Rico and getting ready to set sail across the Atlantic. They’d already done most of the journey, but were looking for crew to help sail the boat across the Atlantic and back. <br><br>I scrolled down. There were comments. There were a lot of people interested. I scrolled through them quickly. Some had already spoken with the person. Some had already joined the crew. But one of the comments said there was still room on the boat if you wanted to join. <br><br>There was no contact information in the advert, but the person running it replied to a comment. Their email was in that comment, so I wrote an email to them. <br><br>And I never heard back. <br><br>I sent a few more emails, but I never heard back. And then I forgot about it. Until a few months later. <br><br>I was at home, browsing through some job search websites, when I scrolled by the advert again. This time I didn’t ignore it. This time I looked at it again. <br><br>And I noticed something I didn’t see the first time - where they’d been. They’d sailed along the Gulf Coast. They’d gone through the Panama Canal and up along the coast of Central America. From there they’d island hopped through the Caribbean. And from Puerto Rico they were going to set sail across the Atlantic, then island hop in Europe and eventually cross the Atlantic again to make their way back to the start.<br><br>My girlfriend and I had been talking about something similar. We’d wanted to sail the Caribbean and Central America. That’s where we’d wanted to go. <br><br>So I scrolled through the comments again. There was one I saw the first time, saying there was still room on the boat if you wanted to join. So I wrote an email to the owner. This time, I got a response.<br><br>I was shocked when I got a response to my email, but it made sense. How often do people look at the same advert multiple times? Especially on job search websites. I’d looked at it twice, a few months apart, and the conversation we’d had in the kitchen had been on my mind for months. <br><br>But something was off. The email conversation didn’t feel right. I’d written the email because of the conversation we’d had in our kitchen a few months earlier, but this email felt different. The email conversation didn’t feel right, and the conversation