What I’ve Learned from Family Travel: 15 Insights From a Traveling Dad

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People sometimes ask me what I’ve learned from family travel. After our first full year on the road, I tried to express how I felt. Interestingly enough, much of what I wrote then still rings true with us today, but there is more to the story.

Jamie hiking in Bukit Lawang — An Epic Education

What I’ve Learned from Family Travel

If I’ve learned anything during from family travel the last twelve months, it’s that school and work can be wherever you want them to be. That means that they’re often where you don’t want them, as well.

I walked around the other night, pondering what I’ve learned over the past year, and many things bubbled to the surface. I’ve listed them out for you below. Some are completely new insights for me, but most of them are simply confirmations (or reconfirmations) of beliefs that I have long felt to be true, but couldn’t affirm through personal experience until now.

I returned to Gary Arndt’s similar (and exceptional) list, and I encourage you to read (or re-read) that list because he covers a lot.

With those in mind, here are an additional fifteen items I’ve ruminated on after a year of full-time family travel:

#1) There Are Great Dads Everywhere

No matter where we go, I see fathers doing right by their kids, whether it’s teaching them to build a fire in Sumatra or cheering them on at soccer practice in Penang. I know that this is all anecdotal, but I simply wanted to say how nice it’s been relating to men — to fathers — in every country we visit.

We’ve seen a multitude of cultures and income levels — from dads stepping out of straw huts to those stepping into white Porsches — and in each of those situations, I’ve seen dads actively engaged with their children.

#2) 24/7 with my kids is as fantastic and horrible as anticipated

I asked for it. I left my job for it. “More time with my kids!” I said, and I got it. It’s been a trial, to be sure, adjusting to working, teaching and learning all in the same space, and sometimes we drive each other to tears (for real), but it’s only drawn us closer.

Having said that, I also realize that I need more one-on-one time with each of them. All four of us — mother, father, son, and daughter — are together, like, all the damn time, and it’s the same when we go out. In the next six months, I need to switch it up: more father-son time, as well as more daddy-daughter days.

#3) Kids Need Friends

Family time is great and all, but there are some things that Keiko and I cannot be for our kids. We cannot be a group of giggling, gossiping girls. We cannot be a soccer team. What we can do, however, is seek out people like this for them (and we’re trying). We’ve had some good experiences so far, but it takes time for relationships to build, at least for a tween like ours: some kid you swim with at the beach one afternoon doesn’t become a “friend” until many texts, fart jokes and soccer matches later.

You sometimes hear about how hard it is traveling with babies and toddlers, and to be sure, it is. But I would do anything if we could go back and start this trip when our kids were younger. Oh to go back to when we were who they really wanted to play with! Back then, Keiko and I were enough for them. Now, however, the desire for peers is growing.

#4) Soccer (Football) is universal

For many in my home country, soccer is for little kids. Sure, this year’s World Cup in Brazil may have shifted the American mindset a bit, but they say that every year. For most of my countrymen, soccer is something they use to tire their kids out with on Saturdays.

It certainly is a big part of my own son’s life, but the sport has been much more for us. It’s been a way to connect with people in every country we’ve stayed. Whether you’re in a cafe, an airport or a jungle bungalow, you can find someone to talk football with you. It is very much a religion. And speaking of religion…

#5) Muslims are (really nice) people, too.

You already know this, but sometimes television and action movies can taint your mindset without you even knowing it. If you went through life simply by watching the news and TV dramas, then it’d be easy to believe that all Islam practitioners have a visceral hatred of the West, its people, and everything they stand for.

Not true. Living in Malaysia and traveling in Indonesia has really brought it all home to me: most practicing Muslims are kind, caring and generous people. Sure, there are genuine nut-cases out there (and the media loves to cover them incessantly), but that small minority of psychopaths makes many Westerners afraid — and hateful — of nearly 1.6 BILLION people. Now that’s crazy for you.

I certainly wish that the mosques nearby didn’t have loudspeakers (hearing prayers five times a day gets old after a few months), but we have had nothing but pleasant experiences here. It’s possible that I would sing a different tune if we moved to, say, Yemen or Mauritania, but what I have seen with my own eyes here strengthens my faith in humanity, not weakens it.

Girl on scooter with ice cream Chiang Mai — An Epic Education

#6) (Nearly) everything can seem relative

Comfort, safety, wealth and class — all of these things depend on the people around you and the situation you’re in. When I fiddle with my iPhone in a Sumatran jungle town, I feel like a first-world bon vivant. Now move me and my device onto the International School campus where our kids join after-school kickball and poetry clubs (I can’t actually afford the school), and suddenly I look like some dirty hippie sending selfies to his yogi.

As for safety, I remember when we first started driving in Malaysia, and how we held our breath, white-knuckling around town like an outtake from Mad Max. Traffic’s no different now, but it barely registers a yawn today. Fear is a choice, they say.

#7) I have so, so, so much to learn

I knew I wasn’t a digital native when I took this leap, but what I didn’t realize was just how much I didn’t know how to make a living off a laptop. “Hey, I’ve blogged before,” I thought, “and well, I know my way around Facebook and Instagram, right? How hard can it be?”

Cue the derisive laughter.

My list of study material continues to grow. I have countless articles, PDFs, webinars and how-to style blog posts lined up to consume, and there will never be enough time. I want to study SEO, movie editing, Youtube marketing, e-publishing, podcasting, photo editing software…the list goes on and on. And I need this stuff. Well, some of it anyway, but I want to learn it all.

But before I can get to it, I still have to figure out lots of the basics, all while keeping up with my day jobs and writing a post for you here each week. Oh, and there are two kids in this house that need some learnin’ put into their heads. Did I mention that I have to teach myself how to teach them? We’ve made some strides forward, but figuring out a basic systemfinding them a soccer team and firing up some apps is a good start, not a mission accomplished. There is much, much more to do.

#8) Getting this life right takes time…LOTS of time

Working remotely? Piece of cake. Supporting a family of four while working remotely? Ouch, that’s gonna be tough. How about while traveling every few months? Are you nuts? Oh, and why not try to homeschool your kids at the same time?

Man-o-man, I really didn’t have a clue. This has been the most difficult time of my life, with one meltdown to remember. But we’ve learned it early and often: perseverance is what’s going to make all of this payoff.

#9) Other travelers’ opinions are not facts

Everyone has their view on where to travel and where to avoid. These should invariably be considered subjective and based on one person’s expectations and experiences at a very specific place and time.

We’ve read people gush over a particular place to eat, then we try it and wonder what the hell they were thinking. Conversely, we’ve been warned to stay away from certain hotels, yet we went anyway and had a great time.

Our experience and our perspective are the only ones that matter. Any time that someone declares that “you shouldn’t go there because I had a terrible time,” view that statement with caution.

Scooter in Bali — An Epic Education

#10) Traveling does NOT equal healthy lifestyle

Business travelers have known this for decades, yet I just figure it out now. I sit in front of a laptop more now than I ever did as a cubicle dweller. And because I’m out of an office environment, I slouch more (when Keiko’s not looking, anyway), and I lounge more on the sofa — yes, I’m working, but I’m sprawled out like a sultan on methadone.

In Tokyo, I was always walking or biking somewhere. I’d pedal my daughter to daycare, then trot to the subway, ascending and descending countless flights of stairs every day. In Penang, we have a car, which means we now get around American style: from sofa to driver’s seat and back again.

Even when we travel outside of Malaysia, we’re often on scooters, and not walking around all day unless it’s part of a planned hike. And when I’m working with the kids at home, it usually involves reading on the couch or writing at the dining room table.

I’m aware that it is me making these bad choices — all I need to do is stand up, stretch and do a few squats every so often and achieve bare minimum — but I can’t seem to snap out of it. This has to change soon, or my quickly-middle-aging body will be permanently screwed. Speaking of which…

Anping tree house, Tainan Taiwan — An Epic Education

#11) I am not a kid anymore

The last time I did this kind of travel, I was in my late 20’s and considered myself indestructible. I drank until dawn, rode motorcycles without a helmet and barged through snake-infested jungles like a steel-plated honey badger.

A small mishap on a waterfall last year made me realize I am, in fact, very destructible. My body is older and not as resilient as before. On top of that, I now have a responsibility to stay healthy and sharp in order to do what I need to do every day: work, learn, teach my kids and model a responsible way of life.

All we own in Taipei — An Epic Education

#12) Living with less is easy — living with a LOT less is…not as easy

Not yet anyway. Last year, it was surprisingly painless shedding a decade-plus of possessions that had accumulated in our Tokyo apartment. Furniture and appliances: gone. Clothes, books, and CDs: easy-peasy.

We trimmed down to just a handful of luggage. Over the course of the past year, we shed two more suitcases full of stuff we didn’t need anymore. That’s two fewer suitcases than you see in the pic above. And the four of us will shed much more once we leave our home base in Penang.

But I’m still attached to things — many things. I cling to my laptops, smart devices, and other electronics. I’m perfectly happy with own five shirts and four pairs of shorts now. However, I refuse to let go of my cameras, lenses and hard drives full of music and pictures.

I love my gear.

What’s more, I still turn to my iTunes account and torrent software to watch movies and TV shows when I need a break. Many traveling families and digital-nomad types have turned their back on more worldly possessions than I have. However, the nature of our life now often requires the use of at least some of these gadgets. That’s my excuse, anyway.

#13) We’re not alone

I’m a social guy, and one of my concerns setting out was not having friends around. This has been a challenge occasionally — sometimes it’d be nice to have my old drinking buddies around to blow off some steam  — but overall, it’s been much more manageable than I’d suspected. However, a more pressing concern than someone to drink with was having someone to relate to — when we left, we knew no one living or traveling like we planned to do.

I discovered quickly that there are many others out there like us. We have met so many amazing families as we’ve traveled. Few of them fit the same mold, but they are all out traveling permanently or semi-permanently with their children.

We’ve met a single mom, traversing Indonesia with her son, island-by-island, on a shoestring. We had a blast with a gap-year family who mixed budget and luxury accommodations and discovered that the kids were adept at both. I’ve spent time with travel junkies, motivational bloggers, vegan unschoolers and a congressional candidate turned ski bum entrepreneur. We’ve splashed around with a family who’ve lived on a boat for the past 13 years and rode into the mountains with a pair of environmental consultants and their sons, who, after enjoying their year abroad so much, decided to move to Bangkok.

And these are just some of the people that we’ve met in person. There are dozens more that I’ve interacted with virtually. Thanks to places like the Families on the Move group on Facebook, I’ve had a forum to discuss what few other people relate to. Here I’ve found people who live nomadically outside their home country and all the epiphanies and pitfalls that come with it. There are many different travel and educational predilections in the group, but the support we’ve received (and hopefully given in return) has been of immeasurable benefit.

#14) There are many ways to do what we’re doing

As you may have surmised by the cross-section of people above, there is no one way to finance your family’s travels. Some people save for a long time and live off the savings, while some sell all their possessions and make their living off the web. Others keep the house and live off the rent. And then there are those like me, who work remotely or have established online businesses. These are just a few ways to do it. Knowing this, nearly every family we’ve met had their own unique style of navigating the world.

#15) Facebook is more helpful/frightening than I could have imagined

When we left  Japan, I used Facebook like everyone does: posting the occasional comment or interesting article I’ve read, maybe a humble-brag here and there, or a cool picture of somewhere I’ve been or something I’m doing. Facebook was important to me already. You see, when you live abroad and your friends are all over the globe, Facebook becomes a go-to place to see people you might not meet face-to-face for quite some time (if ever).

The traveling family groups became so important to me that I joined other groups that shared my interests: homeschooling, traveling and parenting. All of a sudden, the time I spent on Facebook tripled. I was hooked. Well, maybe I was before, but now it was serious.

Then something really began to agitate me. As I would be working on something else — a blog post, web research for work, whatever — I started to see the exact same products I was looking at on Google show up in my Facebook feed. Again and again. This was no surprise, of course. However, it became so persistent that it drove me away from the site a little. Then a little more. I still use Facebook, of course — more than I should, actually. But I now look at it with the caution and skepticism it deserves.

Keiko and I in Cameron Highlands — An Epic Education

BONUS (#16) I would have failed a long time ago without my wife’s support

Well duh…This fact is not news to anyone who knows Keiko. She is the love of my life and the engine that keeps our family moving. This trip was not her idea, it was mine. I am the dreamer and she is the banker in this relationship. She keeps us grounded in reality, but she chose to take this leap because she believed in me. Keiko runs nearly everything so that I can stay chained to the laptop and bang out a living while we’re stationed in Penang.

Being a full-time housewife is not what she was born to do, and I will have to pull my weight again domestically very soon so that she can realize her potential. But if she had not supported me this past year as she has, everything would have fallen apart. I love her for many, many reasons. But the gratitude I feel for what she’s done and who she’s been this past 12 months is something that cannot be expressed in words. I hope everyone can find a partner like that.

This seems like just the beginning  — just the broad-brush concepts off the top of my head. Yet there is much more I’ve learned. Just contemplating the level of privilege I have and was cluelessly unaware of in life has been incredibly humbling to consider. It will certainly be something I will need to unpack and write more. I am an incredibly fortunate person, and I am grateful for everything I’ve learned.

I’m also grateful that you’ve taken the time to read this. Have you come to any realizations in your own life? What have you learned about yourself or the world at large?


  1. This is just a fantastic post. #2.Definitely. Could not have said it better myself.

  2. Pride Hawkins says

    I never thought I would believe a day would come where Jason Jenkins wrote about wanting to learn more about computers. I used to room with a very very funny fellow that liked to sleep a little too much and was too “relaxed” for a person to be (turned out he had some herbal help) but really enjoyed the web site and am so blown away by how great your site is. And how much of a slob I am for not traveling more and staying in touch! So great job Mr Jenkins and hope you are well!


    • Thanks Pride! Ah yes: the hazy daze of a college freshman with no curfew. How I (barely) remember those days. That seems like a hundred years ago. Wish I’d slept a little less back then and got something done. Live and learn I guess!I appreciate your kind words. Hope all is well with you, too!

  3. Thanks for this article, I will now be reading all your tips on Tokyo where we are headed next week!

  4. Great read, thank you for sharing your thoughts. 🙂 We still hope to meet you somewhere along the way!

  5. I am just learning about your journey here. Do I understand correctly in that you and your family have been traveling for a year? Wow. Where have you been? Do you move often? I can’t imagine doing such a thing. Very interesting!

    • HI Larry. Yes, we lived in Tokyo for close to 13 years. My kids (now 11 and 8) were born and grew up there until 1 year ago. At first we spent 2 months each in Taiwan, Malaysia and Thailand, then came back to Penang, Malaysia because that’s where the kids like best. We based ourselves here for a year, but take 2-3 week trips in the region every month or two (Southeast Asia is great with kids). Leaving for Vietnam in the morning. We’ve met so many families doing this, and in a myriad of different ways. Really been an eye-opener of a year!

  6. 2-5 man, especially 2, forever. Love this list, Jason.

    • Thanks Drew. I know you must have contemplated some/all of these. Probably more. I actually thought of y’all while writing #3 — still remember one of Christine’s posts where y’all went around “stalking” children for Cole to play with, and I totally relate to that feeling.

  7. Hope you get this!

  8. Jason, I have written only one facebook reply in my life. Here is number two. I rarely use fb, but when I do, I try to catch up on your travels. Blessings to you and your family as you begin year 2 of your adventure. I am into year 30 of my adventure in Panama. Signed, Uncle Rhett

    • HEY Rhett! Great to hear from you! I’ve thought of you often, man, and I appreciate you reaching out. Perhaps we’ll see you next year or soon after, as Central America is on our agenda next!

  9. Awesome stuff man. Love that picture of you under #9. Good to see you documenting what looks like a great year!