I quit my job and spent 18 months traveling by sailboat; here are three things I learned
Update: I wrote this in February 2019. We now live in Milwaukee, Wisconsin. Continue reading for the full story of how we got here.
Two years ago, my wife and I lived in a one-bedroom apartment in San Francisco. We had full-time corporate jobs, a car, and a busy life full of friends and work.
Today, we live on a sailboat. For the past 18 months, we’ve been sailing and traveling in Central America. We’re fully responsible for our health, safety, and comfort. If we don’t feel like cooking dinner, we can’t grab a phone and order delivery. Instead of a paycheck, we live off our investments, supplemented by income from writing and other projects.
A lot of big stuff hasn’t changed. Michelle and I are still happily married. I have the same great friends. I’m still myself, with my same interests and values. But over the past two years, I’ve nearly completely changed the circumstances of my life.
Why? As the decision slips into the past, it becomes harder to say. Here’s my best shot: I wanted a big life reset, a chance to wipe away the accidental habits, commitments, and aspects of my identity that had stuck over the years.
I wasn’t trying to escape. No, life was very good. But I had taken hold of an idea, a dream, a fantasy. After 15 years of “normal,” I yearned for something different.
Since my early twenties, when a friend lent me a book about “cruising” (traveling by sailboat), I was intrigued by the possibilities of living aboard. By our mid-thirties, my wife and I were approaching career plateaus and looking for a change. We were experienced sailors, and despite our travels, we’re homebodies at heart, so the idea of traveling with our home really appealed to us. This idea, this vision of sailing away, seemed to click. After years of planning and saving, in 2017 we gave up our apartment, sold most of our stuff, bought a boat, and sailed out of San Francisco Bay with no particular destination in mind.
The changes I’ve experienced since leaving San Francisco are not good or bad. Some of them led to breakthroughs and new behaviors, while others have simply made me more grateful for the conveniences of 21st century life.
As I look forward, I’m also reflecting, and I’m thinking about three big lessons that will stick with me as I wrap up this life chapter and begin the next.
Rethinking comfort and convenience
Living on a boat has completely changed my perspective on comfort and convenience. I’ve struggled through sleepless nights because the boat is swinging at anchor, blown around by violent winds. We’ve visited Central American towns where a trip to the grocery store involves taking the dinghyashore, landing on the beach in crashing waves, riding a bus, then reversing the process to end up back at the boat four hours later. We’ve found bugs in our food. As I’m writing this, I’ve got just a wisp of 3G internet, and that’s only because I bought a SIM card from a local mobile provider, stuck it in an old iPhone, and poked through the Spanish-only website to purchase a prepaid data plan.
I’m not complaining about any of these experiences, but they have shined a light on the ridiculous ways I used to seek comforts and conveniences. Sometimes I feel ashamed when I think about it. Getting annoyed at a delayed delivery. Optimizing a process instead of doing the work. Adjusting the thermostat one degree, maybe two, because it’s getting just a little bit too warm in here, don’t you think?
Each of these is a payment of our time, money, or energy toward small improvements in our comfort. And then there are the larger “investments” we make in the name of convenience, like smartwatches, first-class airline tickets, or lightbulbs you can control from your smartphone. These conveniences can be fun. They might let us buy back a few minutes from the drudgery of bureaucracy. They can make us think or help us feel special.
But in the developed world, we view the pursuit of comfort and convenience as natural and inevitable. Of course you’ll take the convenient way — it’s faster, you can get more done, you can make more money. If we see a guy sitting in first class, Apple Watch on his wrist, laptop open, fingers flying across the keyboard, we don’t see a person who has chosen to indulge in the luxury of convenience. We see a busy professional, a man who’s got work to do. A hustler. Successful.
Now, I try to view comfort and convenience as a luxury. It’s something I choose, not something I’m entitled to. This perspective has made me grateful for “normal” luxuries like clean drinking water and fast internet.And it’s helped me realize that trading energy and money for convenience rarely pays off. If I pay to skip the line, do I make good use of the time I “saved”? If I order from Amazon because it’s easy, what have I given up? If I configure my home network to automatically turn on the lights when I get home, is that a time-saving convenience or just a novelty?
I know it’s a great privilege to be asking myself these questions. But that doesn’t mean the questions aren’t important. For me, how I spend my precious time, energy, and money might be the most important lessons I’ve learned from my big life reset.
Finding new value in contributing
In our decision to leave San Francisco and go sailing, there was one default I was particularly excited to reset: the disconnection between everyday life and the basics of, well… life. In the 21st century, it’s easy to live a remote control life, where we order food from our smartphones and stay fit with an iPad app. Clean drinking water is always at the tap. If something breaks, we hire someone to fix it. If we need something, we run to the store and grab it. As long as you can make money, everything is easy and perfect.
On the boat, we have direct responsibility for basics like water, food, and safety. In many places, we don’t even have the option to spend money on these things because there’s no one to bring us water or make us dinner. We can’t depend on the power company; we generate electricity with our engine and solar panels and store it in batteries. Our water comes from a desalinator system that we installed on our boat. We’re on our own.
Most of the time, this combination of total responsibility and complete flexibility is very rewarding. It feels great to sail into an unfamiliar bay and drop the anchor in front of an empty beach, knowing that our batteries are charged, our water tanks are full, and our pantry is stocked. I’m not a pioneer. Heck, I’m not even the first visitor to this bay this week. But there’s an innate, deeply human satisfaction that comes from taking care of yourself, your family, and your home.
Taking care of the essentials feels good, but it also takes a lot of time. I estimate that my wife and I spend half of our time dealing with food, water, safety, navigation, and boat maintenance. My sailing interlude has caused me to question the pursuit of convenience, but it has also helped me see the value in it. When convenience transforms our ability to take care of our basic needs, it frees up our time for other pursuits.
I saw this contrast in stark relief during a break from the boat last year. My wife and I spent the summer in Milwaukee, Wisconsin to avoid the topical rainy season and make plans for the next phase of our life. Living in a developed civilization, our time was (mostly) free for projects, work, school, and volunteering. I released my book, Make Time, and got to talk with people who were reading the book and applying the advice. I taught a series of design sprint workshops with hundreds of eager participants. Michelle volunteered with a couple of organizations and took a class at University of Wisconsin-Milwaukee. We moved into a condo building and began the process of building community with our new neighbors.
I felt an incredible surge of energy from contributing to something bigger than myself. It shouldn’t be surprising, but it was. I had become so obsessed with returning to the basics, I forgot how much satisfaction can be found at the top of Maslow’s Hierarchy. The enthusiasm I felt was a good reminder that while we humans can survive by taking care of our basic needs, to thrive we need to invest our time in the well-being of others.
Relearning what it means to belong
On my best days in San Francisco, I felt as if I belonged to wonderful overlapping communities of co-workers, neighbors, and friends. I saw my colleagues at the office, of course, and sometimes ran into friends on the street. I was a regular at cafés, bars, and the dry cleaner, where people knew my name. I had traditions, like short summer sailing trips up the San Joaquin river, that put me and my wife in reliable contact with a group of friends.
But on my worst days, I felt like part of San Francisco’s tech problem, driving up rents, clogging the streets with traffic, and causing established neighborhood businesses to close and be replaced by overpriced restaurants. Each month, friends moved away, in search of affordable housing or better schools for their kids, and a new batch of striving professionals appeared, like I had years earlier. I felt connected, even to these new arrivals, but based on what, exactly? A physical place? Shared ambition? Love of the California lifestyle?
I spent months inside my head, with thoughts of how it’d feel to leave San Francisco—turning those emotions over and around and preparing myself for the separation. At times, I became excited to leave San Francisco, especially the tech part. I decided it’d be okay if I never heard the words “onboarding flow” or “growth hack” at a coffee shop ever again. But no matter how well I prepared my brain, my heart wasn’t ready for its removal from the familiar sense of belonging.
When we sailed under the Golden Gate Bridge and turned south along the coast, I no longer belonged to any of the old groups. I stayed in touch with friends, of course. My wife and I became closer than ever, spending 24 hours a day together, working as a team to solve problems and as best friends on the adventure of a lifetime. We made new friends, fellow sailors who were going in the same direction for similar reasons. But the threads of connection, no matter how strong, can’t replace the fabric of belonging.
During our summer in Milwaukee, I recognized the warm embrace of belonging again. It wasn’t something I engineered or planned, but rather the result of circumstances: Michelle and I grew up in Wisconsin, so we have friends and family nearby. Milwaukee prides itself on community, and there’s at least one organization explicitly working on creating meaningful social connection there. Milwaukee is not a transient city. Most of the residents are longtimers, and many share a vision of post-industrial renaissance for the city.
In Milwaukee, I learned there’s an alchemy of belonging. It’s not a simple recipe, but it helps to have the right ingredients: a base of strong social connections, a swirl of daily routines and rituals to mix the elements, the substance of shared values, and a dash of seasonal traditions that tie the community to the movement of time.
Looking back, I recognize these ingredients in my San Francisco life, although I wasn’t aware of them when I lived there. It’s yet another lesson I learned from resetting the circumstances of my life.
Today, I’m looking forward to the next chapter. In a few months, we’ll conclude our sailing journey and create new roots in Milwaukee. I plan to live a slower life there, writing, speaking, and teaching—with plenty of time for travel.
Seeing for yourself
If you’re planning a big life reset of your own, you might look forward to learning the same lessons. But you probably have your own goals and your own reasons for wanting a reset. Your lessons will be different. You’ll experience your own surprises, new perspectives, and renewed appreciation for feelings that were there all along.
I’ll resist the urge to drive home my lessons and tell you to take my word for it. I can’t tell you how it’s going to end. You’ll need to see for yourself. And that, I’ve learned, is the real lesson from all of this change: seeing. The results and outcomes are less important than what you see along the way.
It’s easy to let our “normal” life slip away with hardly a notice. Sometimes it requires a big change to see what was there all along.