Why travel now?

We’ve wanted to do some extensive travel for a while now, but until last year had really thought about it as a long-term goal: maybe after Jamie graduates high school or later. The more we thought about it, however, the more we felt that now was the time. As I mention on the ABOUT page, we were working too much and not spending enough time together. Moreover, we realized that for a variety of reasons, we really weren’t going to move any further up the ladders of our respective companies. Then Keiko was laid off. So was her boss. So was her boss’s boss and dozens of others. About that time we went to Oaxaca, Mexico for my sister’s wedding. That was the nail in the coffin of our salaryman lives.


What about your kids’ education? Isn’t this child abuse or something?

No, not really. We are homeschooling the kids as we go. I know the word “homeschool” conjures up lots of connotations, but I really believe that this could be the best way for our family: more time together, the kids can learn at their own pace and we can teach them other skills that I believe aren’t emphasized enough in schools: computers, writing, the arts, history, critical thinking, etc. This will also allow us more time to foster their bilingual abilities — not just speaking but reading, writing and listening. The kids will be required to keep journals, and eventually maintain blogs with reports, movies and photos that they edit and produce themselves.


Shouldn’t your kids be around friends their own age?

This is one of my biggest concerns on the trip: playtime with peers. I do not, however, believe that conventional school — where children spend the entire day with children their own age — is the only way, either. Kids also need to be around people much older and younger than them, I believe. But kids certainly benefit from long-term relationships with friends their own age, so it will be our duty to seek them out. I am looking for clubs and classes that we can join in each country we visit, and one of the first tasks in every new apartment we move to will be locating the nearest parks. I’m sure I will be writing more about this, as it is a crucial component to keeping our family happy.


Who made you an authority on parenting, traveling or anything else?

I’m not an authority on anything, really. But I’m traveling, remote working and homeschooling my kids, so I thought I’d document my experience so that people can learn from any successes and failures I stumble into. You’ll probably learn more from my mistakes than anything. They’ll probably be hilarious. But hey, if you know something that I don’t, TELL ME! I’m learning how to do this as I go along and welcome your input. So if you have tips or advice on anything I write about — homeschooling on the road, remote working, parenting, traveling as a family or any technology that helps with these — I’d love to hear from you, and would be happy to give you a shoutout for your help.


Wait a minute. Jason: I knew you when you were a [kid/high school student/college student]. Why in the HELL would I follow your advice on parenting or anything else associated with responsible adults?

Oh right…Fair point. Uhm…


How can you afford this?

I still do freelance work for the ad agency I’ve worked for since 2002, and I occasionally write for the Japan Times, CNN Travel, Bon Appetit and a few others. I also plan to explore other ways to make money on the web — particularly eBooks — as long as they don’t make me feel like a salesman or a sleazebag.