Answering 2 Bold Questions Created the Courage to Radically Change Our Lives
This is how we chose to leave our careers & sail indefinitely
It was a month into our global sailing adventure when I noticed something inside of me shifted.
I was at the helm of our sailboat, Chérie, fighting heavy swells slapping us in the other direction. Everything that wasn’t bolted down or tucked away below deck was hitting the floor. I heard our cat, Pineapple, howling. I yelled down to her to console her, “Hang in there, baby! We’ll get through it!”
My husband, Corey, did his best to strategize what direction to aim the boat so we could limit our pain while still making forward progress to our destination.
Then, it started getting super hairy. The gusts & swells got much stronger. Our sails weren’t properly setup for these conditions anymore, so we adjusted them to gain back some control. We’d be OK as long as things didn’t get any worse.
But we saw dark clouds heading our way. The forecasts now told us we were heading straight into thunder & lightning within the hour, accompanied by even more powerful gusts.
We didn’t have a lot of options left. We could either keep heading toward our destination and brave the storm, or we’d need to figure something else out.
But I had no time for worry. There was only time for action.
About 15 months before this particularly intense day on the water, we were living in Denver, Colorado, going through the motions.
Corey and I both worked professional, white-collar jobs Monday through Friday. We paid our bills on time and put a bit aside each month for a rainy day. We had as much fun as possible in the evenings, on weekends, and during our few weeks of yearly vacation. But those other 50ish weeks each year were getting pretty damn predictable.
I liked my job decently, though the idea that I’d be doing it for decades longer made my skin crawl. I just didn’t think I had any other options.
Then, disaster struck. Or, rather, what I thought was a disaster.
Corey suddenly lost his job. This was a worst-case scenario for us financially. We had a certain “quality of life” in Denver. Our lifestyle demanded that we made two good incomes.
I’ve described what happened next as a comet that totally shook our world. But the comet wasn’t the job loss — it was the brief opportunity this created to ask ourselves a simple question: Is this even the life we want?
We both answered No. Then, we did some deep soul searching.
We’ve had many people call us “courageous” for the decisions we made next, but I’ve never felt like we were doing anything that no one else could do.
We spent weeks wrestling with these two questions:
What do we need?
What is a reasonable path to make it happen?
And once we answered these questions honestly & thoroughly, we were only left with one choice.
We didn’t yet have the confidence that we’d find a viable path that was much different. But confidence wasn’t necessary yet. We were able to generate something else that would get us started: some curiosity, some excitement, and, then, courage.
The first time Corey floated the idea of leaving Denver, I was opposed to it. I thought, “I finally have friends and a life here that I enjoy. We have a spare bedroom for when my mom visits. I like my boss. It’s a fine life!”
But he planted a seed.
Then, a couple days later, I went back to him and asked him, “So what’d you have in mind?”
We thought about maybe starting over in some cheaper American city. We could move to Detroit or Pittsburgh — two places we’d long been fascinated with because of their unique beauty, emerging art & food scene, and relative affordability. We could lower our household spending. Perhaps we’d take jobs making less money that we were more passionate about.
But this still felt too predictable.
I became so open to the idea of leaving Denver because I could picture everything that would happen over the next decade if we stayed. By many measures, it would’ve been good stuff! We weren’t having kids, so it would’ve just been us and Pineapple, for as long as she kept purring. We could’ve renovated our home, got some promotions, and gone on cool vacations once per year. But going through this list of likely possibilities, it felt like I had already lived it.
We decided we’d need something more mysterious, not simply copy and paste what we had already been doing somewhere new. We suspected we’d just be bored again in 6 months — or worse, we’d still wake up years later and regret not doing something bigger when we had the chance.
We needed a huge adventure with an undetermined destination.
We needed opportunities to explore our endless questions about the world & what we were capable of achieving next.
We needed more vitality in our day-to-day, not just sitting in work meetings wishing we were somewhere else.
I needed to write.
None of our needs included a “big house,” “cushy job,” “power & prestige,” or “lots of money.”
These were our particular needs we discovered through self-reflection, discussion, and tons of research.
And the courage to act kept building.
Once we discovered what we needed, we generated a plan to make it real.
The idea of sailing came up after we had been searching around for alternative lifestyles and we discovered budget cruisers on YouTube. Normal people were living on small sailboats, spending minimal cash, and exploring new places in every corner of the planet. These people weren’t always retirement age and didn’t have millions of dollars. Some had worked & saved long enough to buy a practical boat, pay off their most egregious debts, and then use the remaining cash to start a new life on the water. And many of them still worked as they needed to along the way.
Given our finite money supply, we’d need a very simple boat, fix it up completely by ourselves, and be super frugal. But I wondered, “Could we make that work?”
I didn’t know a thing about sailing and Corey had only sailed small boats years earlier. I asked myself, “Would I like it and could we learn together?”
I worried that my families and colleagues may not understand or they’re think we were nuts. I pondered, “Could we overcome this disapproval?”
We’d need to transit through potentially hostile regions of the country and, eventually, the world. I reflected, “Could we do it as a same-sex couple?”
The answers needed to be Yes.
We needed to walk through our fears that we didn’t have enough and that the world was unsafe. We needed to believe we’d figure it all out.
The only remaining question was — Did we want to do this? Yes or no?
We decided Yes.
In July 2024, 3 months after discovering the concept of budget cruising, we had moved out of Denver, sold everything we could, and loaded up our one remaining car to drive to the U.S. southern coast.
We landed in the cheapest coastal city we could find that had a decent sailing culture, bought the best-yet-affordable sailboat that could eventually cross oceans, and we did all the boat work ourselves.
Though my employer would’ve preferred I lived in Denver, or some city where they had offices, I asked if I could work remotely in a different place for “maybe a year max.” I did good work and they liked me. They agreed. I could then save half my income because our rent was so low in New Bern, North Carolina. Plus, we had gotten rid of most our bills. I’d sock away as much cash as possible while we fixed up the boat and then I’d quit my job.
It took close to a year working in that boatyard everyday. But we would’ve done it for another year if we needed to. We had decided this was what we needed to do, and we’d put in as much work as long as it took.
Once we knew what we needed, had a plan, and generated enough curiosity & excitement, the rest was pretty straightforward. Some days, particularly after setbacks in the boatyard, we would doubt all of it. I remember considering the idea that my life would feel “much less difficult” if we simply quit this sailboat idea. But the decision had already been made. And a bad day wasn’t big enough to destroy our goals.
After close to a year of working in the boatyard replacing every major system, we finally had a seaworthy boat. Then, we taught ourselves how to sail it reasonably well. And a couple months ago, it was time for me to quit my job.
It was scary to give up the stable, good career I had spent years building. I felt fortunate to have it. I was really good at it. And I was proud of my work. But quitting this job was aligned with our new needs and plans, and therefore the courage was accessible. And plus, I was so curious & excited about what would happen when I finally made the leap.
I needed to keep believing that whatever happened next would work out.
Some people asked me, “Can’t you just work from the boat?” but the answer was an emphatic No.
I knew I’d need to pour my entire body, mind, & spirit into sailing life if it was going to work. I couldn’t be straddling our old worlds & new worlds if I was going to create this new life and be successful.
Throughout this entire journey, we needed to make the decisions that were best for us and not lose sight of our goals.
This also meant we couldn’t worry about what other people might think about it, including family, colleagues, or anyone else.
From the beginning, I knew my mom would hate the idea of us sailing around the world, but that didn’t affect our decision to do it. She was pretty worried when I first told her. Her worries made me worried. And it felt like my duty to console her. So, I did what I could to answer her questions over time. She became more encouraging when she saw our progress in the boatyard. She finally told me she was happy for us. And I believe her. But even if she had never come around, it wouldn’t have made a difference in our decision.
Our decision was for us. This was our life. We only got one and so we’d need to live it accordingly.
I was also worried that my boss and coworkers wouldn’t approve of my decision to leave my job. I thought my boss would say, “You’re making a mistake.” And I thought my coworkers might feel like my decision to leave implied some judgment on their decisions to stay. But I was dead wrong. Everyone at work was so supportive. My boss even told me that she would do her best to get me hired back after my amazing adventure.
Considering your most radical decisions in life, what did it take for you to generate that courage? I’d love to know!
Some people might look at the big changes we made and think, “You’re so confident!” — but that’s not true. For me, courage preceded confidence. And courage came from understanding my needs, finding a viable plan to achieve them, and getting a really clear view of what might be possible with total commitment. We all need a future that generates immense curiosity & excitement, and even if it takes months or years to build toward it, we can all access the courage to chip away at it and keep going until we grab it.
We could’ve easily talked ourselves out of our wild dreams at just about any juncture, but this is where the planning phase was so beneficial. We had not only done an evaluation of the costs and charted out a rough timeline that might work. We had found so many examples of others with much less money & experience who had figured it out.
For example, Wind Hippie had $2000 and only sailed solo a few times before she took off south from Maine to the Caribbean. She was a young person who faced insecurities about safety and more, and she has made it work now for 7 years.
Courage isn’t something that some people have and others don’t. People who do courageous things still see the risks and feel fear. But we can all move through it if we have a little spark in us that knows, “This other amazing path is available, too.” For us, that spark led to an overpowering curiosity & excitement for what else was possible. And I’m here to tell you: something else is always possible.
As the winds & water continued to roar around Chérie, we calmly assessed our options. We’d need to handle whatever came up and we knew enough fundamentals to do it. We’d need to come up with solutions instead of wallowing in self-pity. We’d need to be more courageous.
We decided that we needed to abort our original trip and aim the boat to an improvised anchorage about 3 miles away to hunker down before the thunder & lightening came our way. And if that didn’t work, we’d figure it out from there.
I noticed I was approaching this much differently than just weeks earlier. When we were only days into our adventure, we had been in a situation so hairy that I texted my mom saying, “I want you to know that there’s nothing I’d rather be doing with my life.” I said this because I thought I might not survive.
But this time, I didn’t spend a second worrying.
We got to a spot we thought might shield the wind & waves a bit. We still had enough time to set our anchor, tidy up above deck, and heat up some chicken dumpling soup for dinner. Then, the thunder & lightning rolled in.
It would be a rough night, but still, we both felt good about our decisions. Just like everything that brought us to that point, we had done all in our control and then needed to trust our future selves to act, as necessary.
And in those moments, we finally found our confidence.
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Once again masterful story telling on a level rarely seen. What most resonated with me in this story was how the courage displayed in your actions seems large on the outside looking in, but in reality was a series of steps. Courage didn't come roaring in, it was the slow gradual realization that something was more important, and then taking just one step forward. Every step that followed was hard, but each one was met with the courage needed in the moment. You prepared and planned and stepped out taking the next step. That is all we can ever do.
Such a great read. I think this sounds like such an amazing adventure, that storm though, would probably have me sailing back for land indefinitely! 🤣