Why The Radical Life Change?

In early 2006, after our second daughter, Frances, was born, I had the mother of all epiphanies: we should quit our jobs, sell everything, buy a boat, and sail around the world.

March 29, 2012


We have a new blogger! Michael and Windy Robertson are currently cruising aboard their Fuji 40, Del Viento_, in Mexico with their two young daughters. For the next week or so, we will be posting their previous blog entries leading up to where they are today. Enjoy!_

Thursday, November 11, 2010

In early 2006, after our second daughter, Frances, was born, I had the mother of all epiphanies: we should quit our jobs, sell everything, buy a boat, and sail around the world. It took Windy about 2 seconds to agree. Within five minutes, we’d launched the five-year plan that is now wrapping up.


At the time I was reading All in the Same Boat by Tom Neale. In the book he describes the past 20 years of his family’s life, cruising up and down the eastern seaboard, following the seasons from Maine to the Bahamas. Both the Neale girls were raised aboard and seemed to turn out to be respectable young women. I had two girls and I liked boats; it was easy to imagine myself in that life…

Now, to put this into perspective, Windy and I have been cruising before. In fact, it’s how we met. In 1996 I lived aboard a Newport 27 in Ventura, California and signed Windy on as my sole crew for a 7-month trip to Key West, via the Panama Canal (SAIL magazine published an article I wrote about this trip in their November 2007 issue). We had the time of our lives and dreamed of cruising again, someday. Of course, we would first settle down, buy a house, start a family, contribute to IRAs and 401Ks, join the neighborhood association, attend Back-to-School night, and hopefully take two weeks off each of the next twenty years to vacation. Eventually, our kids would get out on their own, we’d help pay for college, maybe a couple of weddings, and then buy a boat to pursue our cruising ambitions. This script was tried and true, the American Dream. So what happened?

On that March day in 2006, I realized an alternative might be more satisfying to us both. We’d grown up, gone to college, found careers, bought our first house, and made a family. All that appeared on the horizon was more of the same. Bigger house? Nicer car? Better vacations? More responsibility at work? For the next 30 years?


1. Wake up.
2. Go to work.
3. Eat dinner.
4. Return to Step 1.

I know that I’m painting a bleak, over-simplified picture, ignoring about a million factors that make our life pretty damn good by conventional measures, but it just isn’t enough. The primary shortcoming is that we are not living together. We are all under the same roof, but pulled in too many directions by economic and societal demands to be really living together.

Until December 2008, we were a two-income family. This meant that we dispersed every morning to live distinct lives. Windy to work, check. Frances down the street to daycare, check. Eleanor to school downtown, check. Michael to work, check. In their early years, most of the impressions that our girls were forming, the synapses they were making, were happening in our absence. Despite the second-mother-like daycare situation for Frances, and a safe, caring school environment for Eleanor, this situation was not sustainable for Windy. Her decision to end her career at National Geographic was an easy one. Because our cruising plans were by then in full swing, I was against her decision. “Stick it out.” I argued, “We are leaving soon.” It did not make financial sense to scrape by on one income at a time when we were trying to save as much as we could.


Since losing that battle, I have seen (in the 5-or-so waking hours I am with my family each day) a steady transformation in her as a parent. Her relationship with our girls and her parenting experiences mean everything to her. I no longer doubt the wisdom of her choice; I am grateful to her for making it. I am grateful for the direct, immediate, and tailored attention she offers Eleanor and Frances, all day long. We are both pleased with this outcome for their sake.

But that still leaves me. While I have a good job and I work with many sharp, interesting people from all over the world, I’m not doing work that interests me. My job is not satisfying physically nor intellectually. I am not driven in any way to do what I do. Rather, it is a well-paying job that I do well, but which keeps me away from my family for the bulk of my waking hours. In fact, whole days go by where I leave for the office before anybody is awake, and return after the girls are back in bed–their little heads filled and expanded with new experiences and associations that do not include me.

Surprisingly, this is not intolerable. Maybe it’s because I am a guy, because I’m wired differently? Maybe it’s because I am not missing what I have not yet been able to know? However tolerable, it seems wrong. Too, it leaves me feeling guilty for those hours I steal away for myself, whether it is work that has to be done on the house or reading and writing that I want to do. How can I have so little time available for my girls and not spend every minute of that time with them? My justification is that they need to see me engaged in my own pursuits. They need parents who attend to self interests and who model the adult behaviors we want them to emulate. Today, Windy is able to offer both. I am not.


It is a problem of lack of time, the bane of families everywhere. My epiphany on that March day suggests a solution to this problem. In cruising, we envision the opportunity to spend nearly all of our time together. We could accomplish the same ends by selling everything and buying outright a small house or trailer in a small town in North Dakota or Mississippi. But in addition to togetherness, cruising offers a rich and varied life for a cost that is less than the U.S. poverty level for a family of four ($22,050 in 2010).

So, we’re trying something new and radical, we’ll see how it goes. We can always come back and rejoin this race, or find yet another path.


_I__n our twenties, we traded our boat for a house and our freedom for careers. In our thirties, we slumbered through the American dream. In our forties, we woke and traded our house for a boat and our careers for freedom. And here we are. Follow along at _


More How To