Travel School. What I Learned Homeschooling my Son for Five Months

My wife, son and I just returned from a 5-month trip. We spent most of this time sailing a boat from Grenada to the Virgin Islands. Just the three of us—it was an amazing, inspiring, awesomely fun adventure.

I had several goals for the trip, but now that it’s over, I think one of the best parts of the experience was homeschooling our son, who turned 13 on the trip. With two caveats*, I’m going to try to highlight some of the best parts of that experience, and ways in which any parent can try to achieve some of the same benefits we found without quitting a job or heading out on a sailboat.

Put another way, here is a very big question that every parent should ask: What is the best way to educate my children to maximize the chance that they will be smart, creative, curious, happy adults that make a positive impact on the world? In other words, successful.  

What School Doesn’t Teach

I read a book recently called “How Children Succeed.” In the book, the author bifurcates the skills and capabilities that education teaches our kids into cognitive and non-cognitive groupings. Our current educational system stresses the cognitive. Math skills, reading comprehension—stuff that you can practice through repetition and that can be easily measured and tested. But what about the non-cognitive? Things like persistence, self-control, curiosity, grit, self-confidence and creativity. These are much harder to teach or measure in a standardized setting, but they are highly correlated to success in the real world.  Some people call them character.

What School Teaches That You Shouldn’t Learn

I’m an entrepreneur. I’ve been able to make a great career, despite the fact that I didn’t go to school to study to be an entrepreneur or even learn about business (secret: my math skills weren’t good enough to get into business school). I learned most everything I know about my profession by jumping in and muddling through.

And although my 20 years of traditional education taught me a great deal, I actually had to unlearn a couple of things from school that would have held me back from success. I wrote about these lessons here, but the short version follows. School taught me that my teachers and professors will tell me what I need to know—I could just sit back, memorize what they taught me and wait for their graded approval. School also taught me that in order to be successful, I needed to be good at everything. This meant that I spent the majority of my time devoted to subjects in which I lacked a natural talent. Successful people in the real world do NOT follow these two lessons. In fact, they do the exact opposite. If you want more evidence of how our current educational system is creating generalist followers, this talk by Sir Ken Robinson is worth watching.

Our Travel School Challenge

Thus, we looked at the opportunity to take Jimmy out of his 7th grade classroom for a semester as a challenge. How could we best compliment his ongoing public education? How could we develop those non-cognitive skills and provide him with the best opportunity for adult success?

A Few Things We Did

I’m not an expert in education and I don’t pretend to know all of the answers. But here are a few things that we experimented with that seemed to work.

#1. We put Jimmy in charge of as much as possible.

What do you want to learn? Pick a few things that really interest you. Jimmy picked fishing. He picked learning about sharks and the other creatures that live in the Ocean and on the islands of the Caribbean. He picked investing and the stock market. And we also encouraged him to ask questions about the world around him and we would help him figure out how to answer those questions.

Hidden lesson: don’t wait for others to tell you what is important. Go out and do what interests you. Find out stuff that you have a “knack” for doing. And do more that stuff.

#2. Curiosity meet the Internet.

We have a box of old encyclopedias in the room above our garage. That’s where I was forced to go for answers when I was thirteen. Today, we have the Internet. Anything you want to learn, you can. Never in the history of the world has it been easier to follow your interests to become an expert in something.

Throughout our trip, we researched questions that came up, like tides and weather and Communism and Darwin’s Theory of Evolution. Why does Apple make so much money? Why is the Ocean blue? Why do my ears pop underwater? Those are great questions Jimmy. Let’s figure them out. And we also tried to be proactive in certain subjects rather than just reactive to specific questions. We subscribed to podcasts. Jimmy learned the ukulele from YouTube videos. We signed up for online courses on physics and computer programming. And although we didn’t get around to doing ½ of the stuff I’d hoped to accomplish (like learning to program), I think all of this demonstrated to Jimmy that there is a big, amazing world out there that he can dive into anytime he wants.

#3. Blurring the line between schoolwork and life.

Before this trip, Jimmy’s life was organized into pretty tight segments. School time, homework time, and all that other time when he didn’t have to learn anything and was free to actually have fun. We turned this upside down on our trip. Sure, we had a few set school tasks to keep Jimmy up on his cognitive skills like math, reading comprehension and writing, but we kept scheduled school time to a minimum.

Instead, we tried to weave learning into just a normal part of each day. A great example of this is something that we did for entertainment. Because we didn’t have T.V. or Internet often, I downloaded NPR’s Serial podcast on my phone for us to listen to at night after dinner. The podcast was about the trial and conviction of a teenage kid for the murder of his girlfriend and the lingering questions about his guilt or innocence. And although it entertained us as much as a good television series, it also taught Jimmy a ton about the rule of law, how our courts work, criminal law, debate, and truth and justice. But it never felt like school. This happened over and over as we simply explored the “real world” on our trip and Sarah and I talked about things the world has already taught us.

#4. Experiment with Calculated Risk Taking.

A lot of the things that I’ve achieved in life have been the result of calculated, thoughtful risk taking. I bet you can say the same. Yet why is it that in the U.S. we work so hard to completely take our kids out of managing any risk in their lives? Many of us would put our kid in a giant protective bubble if we could. I think it’s a big mistake. Kids are capable of much more than we sometimes give them credit.

We saw this first hand during our time on the Island of Dominica. Dominican kids are treated like little adults. For example, many of these kids receive a machete before they turn 10. A big, sharp machete. Yet, we didn’t see a single kid missing a finger or hand or worse from this responsibility. They step up to the responsibility and they become very confident in the process. Jimmy took a lot of calculated risks on the trip. He learned to scuba dive. He checked our anchor by himself. He swam in deep water where he couldn’t even see the bottom. We bought him a machete. We made him “captain for the day” at the end of our trip and he was in charge of sailing a 41ft, thirty ton boat from point A to point B. And each time he used his own judgment to manage a risk effectively, he got more and more confident and better able to understand a good risk from a bad one.

#5. We weren’t normal.

To be exceptional at something you must, by definition, be outside the norm. Yet, as social creatures, we feel a tremendous obligation to fit in. To go along. In most professions, just fitting in isn’t going to get you very far. And finding true happiness in life often involves having the guts to write your own script. Our trip was a bit crazy and atypical. It was really different. And not only did it show Jimmy how big the world is, I think it has also given him the permission and freedom to be different when he so chooses. To put another way, Jimmy now views being different as a positive part of his identity. I think this is a tremendous gift to give any teenager.

Empathy—An Unexpected Result

I listened to a podcast interview of Chris Sacca recently. Chris isn’t exactly a household name, but he is one of the best early stage investors on the planet and he has over a billion self-made dollars to prove it. When asked what he viewed as the most undervalued skill in an entrepreneurs skill set, he didn’t hesitate with his answer—Empathy. I couldn’t agree more. It’s hard to make any change in the world without influencing other people. And it’s impossible to influence people unless you understand their worldview. What makes them tick. What they fear and love and hope for. That’s empathy.

We didn’t explicitly set out to try to teach Jimmy empathy on our trip—it just sort of happened. Looking back it makes sense. We met people from all walks of life: All sorts of different ages, income levels, nationalities, ethnic backgrounds, and cultural backgrounds. We ate and drank with them, we worked with them, we hiked and explored with them, we played with them, and we tried to help when the opportunity presented itself. And Jimmy was like a sponge in each of these experiences, soaking up our differences, asking questions, trying to make sense of why all of us do what we do in life. My guess is that this part of our experience will be the most lasting and most impactful part of our road school experiment.

Some Stuff Didn’t Work

I don’t want to paint too rosy of a picture here. Not everything we did worked. Hardly. The best example of this is probably my efforts to instill in Jimmy the value of deferred gratification (doesn’t it feel better to play on your phone after you get some quality work done?). During the trip, we worked with Jimmy to fill out a daily and weekly “sheet of integrity” that listed the things he wanted to accomplish. He did this every week and most days, and even experimented with the format of his lists. I hoped that this would result in an epiphany—it feels better to relax and goof off when I’ve done something worthwhile first. I had visions of Jimmy at home this summer, getting up and independently setting his priorities for the day.

It hasn’t turned out that way. Left to his own devices, I’m pretty sure he would play video games and binge watch Netflix all day. Perhaps I had too high of expectations for a 13 year old. Perhaps I just need to give him the control to be a slacker for a week or two and miss accomplishing things. I’m not sure of the answer, but I wanted to point out that we don’t have one yet. All of this is a work in progress.

Wrap Up—Things you can teach without buying a sailboat or quitting your job

Parents can be divided up many different ways, but here let’s divide them into two groups: those who continually work to become better at the job of parenting, and those who do not. My guess is that any parent reading this post falls into the former camp. And I hope that I’ve inspired you and perhaps given you some new things to try in your quest to give your kid the best chance of being a success.

To that end, here are a few specific ideas.

#1. Explore life together.

Go out and do something with your kid in the real world. Sign up for a volunteer experience. Road trip to a new town for the day. Visit a museum (yawn). Get outside of your day-to-day routine together. Doing this has two huge benefits: a) it shows your child that you care about them with your actions; and, b) it enables them to learn how you navigate and understand the world. You are their most direct and impactful teacher. And if you really want to make it count, do something atypical/weird that gives your kid permission to be unique. Don’t just go to a museum, have a contest to see who can find the ugliest work of art or the most obscure collection of things. Don’t just visit a small town, see if you can find the best piece of pie in your area. Don’t drive through a city. Walk it and see what you find. You get the picture.

I just finished an inspiring book about death. That might sound impossible, but Peter Barton, the former CEO of Liberty Media pulled it off in “Not Fade Away: A Short Life Well Lived.” In the book, Peter approaches his impending death from cancer, and although this guy made gobs of money and rubbed shoulders with the rich and powerful, the thing that he seems most proud of is a series of field trips he designed and took with his kids that he called “Real World Outings.” They learned where things actually go when you flush the toilet. They learned about fast food. They visited an airport and studied luggage handling. Simple stuff, but it had a huge impact on him and his kids.   Most of us have the ability to do these things. They don’t require millions of dollars or weeks of time. Go do something together.

#2. Introduce your kid to risk.

Resist the temptation to put your child in bubble wrap. Seriously. Financial risk, bodily risk, emotional risk. Let them quit something. Buy them a lottery ticket with their piggy bank money if that’s what they want. Do something physically challenging that takes courage. Give them something that they view as dangerous. Take the coffee challenge with them. And most importantly, even if they aren’t really in control and you are supervising the whole thing, let them feel like they are making the decision to take the risk.

#3. Live in an intellectual household.  

We watched an amazing movie the other night called “The Lady in No. 6” about Alice Sommers, the oldest holocaust survivor in the world. It’s a short film and I’d highly recommend it for a number of reasons. But the one I’ll highlight here is what Alice said about her education. According to Alice, the most important form of education anyone can receive is to be brought up in an intellectual household. In fact, she credited it with setting the framework for her amazingly rich life.

Just what does that mean, an intellectual household? To me, it means that as a parent you remain relentlessly curious about the world and that you share this curiousness and what you learn with your kids. Ironically, that is what I was trying to do while watching The Lady in No. 6 with my kids. Learn more about human nature and happiness.

Here’s an easy way to get started. On your way home from work ask yourself, what did I learn today? And then share that with your kids at dinner.

One thing I’m going to do this summer—paint one of our kitchen walls with whiteboard paint. And anytime I learn something new or cool, anytime I have a question or I’m confused, I’m going to whiteboard it. And I hope I can get the rest of my family to play along too. One example: “you are the average of the five people you spend the most time with.” You don’t need a literal whiteboard, but I think the image of your family whiteboard captures what it means to live in an intellectual household. Is your whiteboard empty or full?

In closing, I’ll respond to what many of you are thinking—I don’t have the luxury of time to do all of this stuff. And some of you may not. But I’d challenge you to really think about how you spend the hours of each day. Here’s a personal example. If you are like me, you’ve probably invested a great deal in your kid’s athletic career. You’ve paid for camps. You’ve driven everywhere, even across state lines. You’ve sat on the sidelines. Hours and hours and hours of time. Don’t get me wrong, I love sports and I think they have a lot to teach kids. Athletics and exercise are a huge part of my life. But think about this time and whether you could take just a small portion of it to do some of the things you’ve come up with from this post. And then ask yourself which set of hours will have a bigger long-term impact.

Bottom line, even if everything you try fails miserably, your child will be left with the most important belief of all—that you care deeply about them and tried your best. Anything else is really just extra.



I apologize for doing a humblebrag about my own child. I couldn’t think of a way of talking about how great our travel school experience was without using specific examples of the benefits I’ve seen reflected in Jimmy.

When I criticize our educational system, I’m talking about the system and not the teachers that participate in that system, may of which are wonderful, caring and smart people that make a difference in lots of lives.

3 thoughts on “Travel School. What I Learned Homeschooling my Son for Five Months

  1. No need to build another company, Mark. Your next chapter could be a Youtube channel where you take 13 year old kids on real world adventures to inspire parents and families. I have a couple loaner kids to help you start up…
    In all honesty, this was a wonderful post. My dad was all about the real world outings concept – an excellent teacher of how things worked – and I’ve tried to follow that path with my kids. Thanks for sharing.

  2. Pingback: Why I’m Working at an Insurance Company | Blog of Mark McGuire

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