How Finding the Nerve to Abandon Your "Plan A" Might Be the Secret to Happiness
It's not a one size fits all world
Hello shipmates,
Yesterday evening, we arrived in Newport, Rhode Island! This is likely as far north as we’ll go before the prevailing winds change in September. Then, the plan is to head back south to the Chesapeake Bay. We have a new mainsail waiting for us in Deltaville, Virginia. That stop will likely be accompanied by a long list of boat projects. Then, as hurricane season winds down, we’ll make our way to the Caribbean, Latin America, and beyond.
We have big plans over the next 6 months!
But, of course, the plans I laid out above can change at any moment. If the prevailing winds don’t shift until late September, that means we can head further north. If we learn about some new island somewhere that we must check out, we’ll do it. As sailors, our Plan A rarely works out. So, we must learn to pursue Plan B with just as much gusto.
I wrote the essay below while reflecting on my pre-sailing life and how many times I’ve needed to abandon my Plan A. I’d get new info, so I’d change my mind. But I had a surprising take-home: Plan B always worked out better.
Later this weekend, I’ll publish a new Logbook about our journey sailing to Newport. It’ll include details of our 33-hour, overnight sail from Long Island to Block Island — a beautiful paradise about 40 miles off the coast of Newport. I’ll also dig into what it’s like being a frugal sailor in a vacation town while not being on vacation, and how I’m adjusting to that reality.
I hope you enjoy it all!
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How Finding the Nerve to Abandon Your “Plan A” Might Be the Secret to Happiness
It’s not a one size fits all world
A few years ago, my husband and I were working our 9–5 jobs and dreaming of adopting a kid. That was our Plan A. We talked to an adoption agency and other parents. We learned everything we could. We thought it through like our lives and a child’s life depended on it, because it did. When it came time to make the decision about whether to move forward, we knew in our hearts that it wasn’t for us.
It would’ve been so easy to do it anyway. What else were we going to do with our lives? We already told people we were planning to adopt! They all told us, “You’ll never feel ready!” But we each listened to our inner voices, then we discussed it over weeks and months, and we decided that choice wasn’t right for us.
The good news was we’d get to find another path to make our lives fulfilling and worthwhile.
I used to wish that I could live 10 lives simultaneously. But since I cannot, I deeply consider the pros and cons at each juncture before taking a big step. After weighing all the factors involved in parenthood, major career decisions, and what I want to do with the rest of my life, I’ve learned that most of the time I prefer the less obvious path. My first idea is usually not the best fit given my unique personality and situation.
I need to embrace Plan B, which only materializes when I stop and think. But I always find something better.
If we had become parents back in 2023, I wouldn’t be writing this from a small sailboat with our sights on a circumnavigation. I’ll get back to that.
We get to explore all options at a crossroads
At 18, I briefly considered moving to San Francisco to attend film school. I toured my prospective campus. I put an application together. But I knew in my heart that film school wasn’t a good idea for me.
The reason I really wanted to go was because I felt like I needed to do something. At that age, the most obvious next move was going to school and, back then, I wasn’t interested in anything else other than film. But I’d need to go tens of thousands of dollars in debt in pursuit of this idea. Upon further reflection, I realized I didn’t really want to work in the cutthroat film industry. So, I changed my mind.
But I stayed on the lookout for some other inspiration to strike.
A year later, one of my coworkers at Starbucks had just gotten back from living abroad. She taught me the ins and outs of how to get a working holiday visa in English-speaking countries. I treated her like a prophet. Then, I saved up all the money I could and I moved to Australia. I worked odd jobs in multiple cities and met dozens of inspiring foreigners who offered me new perspectives on my life and country.
It was the most formative experience of my life up until that point. It’s where I learned that I could live according to my own metrics of success. It’s how I discovered that saying no to one path wasn’t the end of the story. It taught me that Plan B could lead to a more fulfilling life.
Most paths we consider to be “Plan A” are imposed by outside forces.
Our society presents a default track that may work for us, but it may not. We’ll get strong suggestions that we should simply do well in school, get a job, settle down with a traditional family, and be grateful if we can pay our bills or go on vacation once in a while. But it’s a statistical certainty that some subset of people will be outliers and will not be satisfied with the predetermined path. Still, too many of us never push back or ask questions. It seems easier to assume that following what others did will work for us, too. Then, we keep pushing forward for years or decades like there’s no offramp. And we blame ourselves if we’re unhappy.
There is always a Plan B
When we decided no to becoming parents, we looked for some other path that would suit us better. We entered exploration mode. We would finally end up finding an option we didn’t know was out there.
We found examples of adventurous people who had totally uprooted their lives. We discovered folks on YouTube who were living off the grid. We identified blogs about families that moved into a van and explored their country. Our gears were spinning, excited about what else might be possible for us, and we kept looking for the right idea to strike.
Then, we discovered examples of seemingly normal people who had left their careers to live on sailboats and explore the world’s oceans. We investigated it, we asked questions of people who had done it, and we weighed it against our principles. It felt exciting. We were so curious about how it would turn out if we joined them. And so, last year, we decided to quit our careers to sail around the world.
We always have the ability to change our minds
Before we gave up everything and chose sailing, we tried to make little changes to see if they would keep us fulfilled. We didn’t want to do anything too radical. So, I applied for a promotion at work. We tried to go on more interesting vacations when our jobs approved our leave time. I believed that if we personalized our house more to our liking, maybe that would make me happier. But it wasn’t enough. That’s because I wasn’t yet willing to reevaluate the fundamentals my life was built upon.
Plan A wasn’t working, but that didn’t mean I didn’t try my best.
We got a mix of reactions when we broke the news to family and friends that we were going to live on a small sailboat. Some people were confused because they thought they had us figured out. But the people who knew us best weren’t shocked. They knew we were the type of people who routinely reevaluated our trajectories and would make new choices based on ever-changing wants and needs.
It can be hard to accept that you’re an outlier who is not happy following the set of options that might make other people happy. You look around and see everyone either looking satisfied, or at least accepting ambivalence, and it can make you feel like there’s something wrong with you.
But when we start looking beyond our immediate surroundings, we discover that 1000s of people — including families and folks from all backgrounds, generations, classes, and abilities — are living every conceivable life imaginable. Many of their lifestyles are more desirable than what we’ve been doing.
We still faced doubts even after deciding to explore a different option. We knew we wanted to live on a sailboat but we couldn’t afford the most glamorous of the options — like a huge catamaran. We weren’t millionaires. But these hesitations were the result of us still treating a specific type of sailboat life as Plan A.
We soon discovered examples of sailors who had limited cash to get started and figured out how to make money while they were on their adventure. They would buy small vessels, do all the boat projects themselves, park their boat at anchor for free while exploring new destinations, and perform whatever sorts of jobs they needed to make ends meet. We followed their lead.
Plan B has been a dream come true
It’s been 15 months since making the decision to leap and we now live on our sailboat full-time. We’ve sailed nearly 1,000 miles from the American South to the Northeast to learn everything about our boat and this life. Next month, as hurricane season winds down, we’re heading south to the Caribbean, Latin America, and beyond.
We have dreams of sailing for many years, but the truth is that we are going to reevaluate everything after 1 year. We’ve never explored on a sailboat before. It’s going to take awhile before we have fully investigated this path and would consider looking at a Plan B. But if we hate sailing, we’re tired of the cramped spaces, or our financial situation changes, we’re not going to stay miserable forever.
As we try new options in life, we’ll always discover new insights about ourselves, including what we want and need. Our priorities will become clearer or shift. Our worlds change and we need to adapt accordingly. But that’s the point.
I may not be able to live 10 simultaneous lives, but if I live 80 years, I can live 10 consecutive ones that reflect careful consideration based on what’s important to me. And that’s how I’m building an authentic and full life.
Until next time,
—Cory Vinny
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I didn't realize until I left America has overwhelming its "message" is: Work your ass off to get really rich, and buy lots of things which will give you status and make you happy. It seems fairly ridiculous now. But I don't think the leap is NEARLY as dramatic as most people think, at least if you've never really fit in in America. I keep saying, "My life is FAR less stressful than it was before." Then again, I'm not living on a sailboat!
You touched on something really powerful when you said, "It can be hard to accept that you’re an outlier who is not happy following the set of options that might make other people happy."
To me, there’s a quiet courage required to stand in that truth, especially when it feels like everyone else is marching to the same beat. It's a journey of self-acceptance, learning to trust our inner compass even when it points in a direction few others are taking. This recognition that our unique journey isn't a flaw, but rather a profound strength, is truly empowering. It gives us permission to design a life that genuinely fits us, rather than trying to fit ourselves into a life that doesn't.
Thank you for sharing 🩵