Trail Financial Planning, LLC is a fee-only financial planning and investment management firm located in Bellingham, WA

How a teacher and small business went with their 2 kids to Asia for 4 months.

How a teacher and small business went with their 2 kids to Asia for 4 months.

Have you ever vaguely thought that financial planning is something you should do, but you weren’t actually sure what it was?  In this post, I tell a story of one facet of financial planning:  setting and achieving goals.  In this case, I will tell the story of how my family spent 4 months travelling through Southeast Asia.  To carry it out, we needed intention, planning, and careful financial management. 

Our story:

In 2017 our family of four spent four months travelling around Southeast Asia.  We called our trip “Four for Four – Cheeseburgers in Asia.”  We communed with elephants, we soared across the Laotian jungle, we licked the most delicious peanut sauce from our fingers, we laughed with faces that spoke no common tongue to ours.  Four months away from work and regular life.  Four months exploring different landscapes and cultures.  Four months of intense togetherness.

Many people have asked us how we did it.

This post is such a description – how we managed our work, our money, the kids’ school, and our attachments back home.  If you want to read more about what we did, I included some links to posts we wrote while travelling on our family blog at the bottom of this post ([1], [2], [3] and [4]).  In this post I will describe how we set a goal, and set about carrying it out.  We needed intention, money, time, and a bunch of logistics planning. 

Disrupting normal life is not easy.  Amy, my wife, and I are about as disruptive as a Sunday afternoon quartet playing Beethoven at the neighborhood Presbyterian Church.  I’d be lying if I said the trip was easy.  But, I’d also be lying if I said I wasn’t proud of us.  Hopefully this post will inspire others to dream, and set a plan to fulfill the dream.   We did it!  Here is how we pulled off “Four for four:”

Step 1 – We built intention

In 2013, Amy and I went out on a dinner date.  Our MO on such occasions is to careen into existential conversation like, “What the hell are we doing with our lives?”  While I was looking at the bill, sipping the last of my wine, we started talking about travel with our kids.  At that time, Mia was in 5th grade, and Porter was in 2nd.  We had several trips we wanted to do, including an extended overseas travel experience.  On the back of the restaurant receipt, we listed the places we wanted to go, and the time available.  

Travel goals – Southeast Asia, Africa, Europe, Mexico, Central America, and a longer travel experience.

Time resources –  Seven summers before Mia would finish high school.

We figured that we could pull off an international trip every other year.  Oh crap.  And what about that longer trip?  

Step 2 – We planned the time

We decided a four month trip made good sense for our family, and for Amy’s business.  She owns a sole proprietor business.  On one hand, she is her own boss with no employees, so she gets to set her own schedule.  On the other had, when she doesn’t work, the business does not operate.  She had a good reputation as a therapist; she gets more referrals than she can handle.  She  wanted to be sure her existing clients would not feel abandoned.  She determined that her practice could undergo a four month “pause” without too much difficulty.  

We identified Mia’s 7th grade year as the right time – after she had a full year start to middle school, but before 8th grade and high school when school might feel more academic.  We circled the year on the receipt, and told the kids about our plans.  They took the news as kids often do about something totally incomprehensible:

Mia, our 11 year old, looked at us thoughtfully, “Uh, ok.”  Then her brow furrowed, “I guess so, but like, when?  Which grade will I be in?  Where will we go?  How will we get there?  What are we going to do?  What would I do for school?  What would I eat?  What about Josie (our dog)?” She is her mother’s daughter.

Our 9 year old boy, Porter, responded with “Uh, sure.”  He is his father’s son.

We started telling others of our plans.  By writing down our goal and saying it out loud,  we gave the trip a certain destiny.  We went back-and-forth about what time of year to travel.  Amy and I decided on December through April, mostly because the window offered the best weather in Southeast Asia.  In addition, we could leverage the kids’ school holidays.

In the Spring of 2016, I wrote a letter to my school district asking for the time off (without pay of course) from my job as a high school teacher.  My principal was completely supportive.  So was the head of human resources.  It was as if these people read my request, and wanted the same thing for themselves.  They enthusiastically endorsed my plan.

Amy’s time off was a bit trickier.  She is a mental health therapist in private practice. Six months out she began telling her clients that she would be gone that winter.  At first, it seemed okay.  But then, the election result came in, and many of her clients seemed to experience re-traumatization.  Challenging.

Nevertheless, we left for the airport on December 11, 2016.

Step 3 – We planned the money

How much?

I did some research.  Major research.  Meaning, I googled “How much does it cost to travel through Southeast Asia with a family?”

Turns out, there are many people who have written about this.  The “Indie Traveler” site was particularly useful (see note [5] for web reference).  Costs were reported as between $30 – $50 per day, per person, depending on the country.   I budgeted about $150/day, or $20,000 total, for our family.   

This turned out to be a pretty close estimate.  At the end of the trip, I totaled our expenses: $19,262 for everything except flights to and from the USA (we used frequent flyer miles for those), or about $156 per day.  Wow, pretty close!

How to pay?

We paid for our trip out of savings.  Since neither of us would earn income while we were gone, we needed to self-fund the trip.  We didn’t have the money saved before “the receipt,” but once we had committed to a dream, it was amazing how good we became at saving.  For about a year and a half before we left, we examined our monthly cash flows, and took a knife to our expenses.  We skipped a couple ski trips, and we cut down on restaurants.  We aimed to save about $1,000/month.  After a year and a half, we had about $25,000 in savings.  We didn’t want to use all of our savings (an emergency fund is important), so we also pulled some money from one of our Roth IRA accounts where some stock investments had done well.  Thanks to Apple and its iPhone!

Our actual travel costs: 

Although we tightened our belts before our trip, as travelers we lived well.  We did everything we wanted to, basically without regard for cost.  Of course, one’s travel style will be important here.  Our style is sort of the Do-It-Yourself, but without the cooking.  The major categories of expenses (listed in order of fun) were activities, food, accommodation and transport.   

Activities and adventures – about one-third of the total cost.  Some adventures were cheap (motor scooter rides, hikes and public museums), while some were expensive – our guided trek in Nepal cost $2,700 for seven days.  I included some links to written up descriptions of our travel at the bottom of this post.

Food – about 20% of the total cost.  We ate good food every day, at restaurants or on the street.  We discovered “the hotter and fresher” was usually the best, and often the cheapest.  Asia is a foodie’s dream.  Food is everywhere, in little street carts, hole-in-the-wall restaurants, and some bigger restaurants.  People seem to be constantly eating what is cooking.  When we would ask for a leftovers box, they looked at us like we were crazy (which makes good sense in a tropical climate where refrigeration is rare!).  We could eat on the street for about $2/meal per person.  Restaurants and cafes were more – around $4-5/meal per person.

Accommodation was about 25% of the cost.  We stayed in lots of different styles of accommodation, from gritty hostels to fancy hotels.  Our favorites were moderately priced home stays, where nice, clean, rooms cost between $30-$50 per night.  We loved the individuality, the people who ran such places, and the other travelers we met there.

Transport was about 25% of the cost.   We traveled by plane, train, bus, taxi, motorbike, tuk-tuk, song taew, long boat, bike, foot, and the back of a few trucks.

How we accessed money overseas

We paid some for some things with a VISA card, but mostly we used cash.   We took out $300 – $500 every few days from an ATM machine; currency was delivered in local Baht, Dong or Rupiah.  The machines were ubiquitous in popular tourist areas.   The fees were modest (1-2%), and worth the low stress of not carrying a lot of cash around.  A few times, we needed a bunch of money at once to pay ahead.  For example, at “BEES Elephant Sanctuary” (see [2] for link), we needed to arrive at a remote location with over $1000 for a several day experience.  We just planned ahead, and hit the ATM a few days in a row, so it worked out.  There were other issues – border crossings usually required US dollars instead of the local currency of the exiting country.  We didn’t bring too much US cash with us, so we had to go to banks to do cash advances.  Cash advances are expensive.  If I did it again, I would have figured out how much US cash we would need, and just brought it in a hidden pocket.  We could have used around $500-$1000 US cash for travel visas and other miscellaneous costs.

At first I kept track of our expenses with a detailed travel budget app.  But after some time, it became annoying.  I just wanted to experience the time and reflect upon it.  At some point even I, a spreadsheet geek, didn’t want to analyze it.  However, I persisted, because I knew I wanted to write this post.

US-based expenses

There were some US expenses that we had to cover, notably our home mortgage and health insurance.  Fortunately, we found a family to live in our house.  They paid for most of the mortgage payment and utilities while we were gone.   Health insurance, on the other hand, was just flat-out expensive.  Travel insurance provides for massive amounts of peace of mind, and is very reasonable.  However, our US-based health insurance was expensive.  We paid nearly $1,200 per month for Amy’s policy and a COBRA policy for the kids and me.  Ouch.  Luckily we didn’t need to use it for any real ouches.  But, peace-of-mind is tough to put a price on.  We did not want to skimp on having access to good health care.  

Here are a few things that I learned about medical care and health insurance. 

Medical care overseas was excellent. We went to a doctor or other medical provider several times on our trip, and we received excellent care each time.  Our needs were minor, so we just paid for it.  Total expenses for three visits:  about $100 including some prescription costs. 

Travel insurance.  Travel insurance was relatively inexpensive – about $150/month for the entire family [6].  We wanted it in case we needed emergency evacuation.  Travel insurance companies specialize in working with systems overseas.  We never needed it, but well worth the peace of mind. 

Our US-based health insurance.  We decided to keep our US-based health insurance while we were gone, in case we needed to come back to the US for care.  Fortunately we never needed to.  Although very expensive (we paid about $1,200/month for our family), we would not have done anything differently.  We wanted to keep access to a medical system we know and trust.  That said, the manner we kept US health insurance was a little clunky, and we probably could have done it better.  Amy has her own plan as a self-employed person.  We just kept paying the ~$350/month.  That was fine.  The kids and I are on a plan offered through my employer (Bellingham School District).  I was informed that I could sign up for COBRA.  I did, and it cost about $900/month.  What I did not realize was the “COBRA” is considered a new plan.  So deductibles and maximum out-of-pocket expenses reset.  Even though the health insurance was the same exact plan, with the same exact benefits, offered through the same exact provider, and I paid the same exact premiums, we ended up with a “reset” on deductibles and maximum out-of-pocket expenses twice in 2017: once when COBRA kicked in, and once when we switched back to my non-COBRA plan (when the 2017-18 school year began).  Grrrrrr.  Next time, I will research this a bit better.  There are bound to be more economical options than what we did.   

Step 4 – We figured out school for the kids

For many families around the world, leaving school for four months is difficult.  Some European citizens told us they get fined for for taking their kids out of school.  As a teacher, I know how difficult it can be for a student to be gone from school for an extended period.  Fortunately for us, the US school system is more lenient.  Officially, we un-enrolled the kids from school.  That turned out to be pretty easy, though Mia lost much of her electronic cloud-based work in OneDrive when her account was deleted.  That was a bummer.

Our kids’ teachers were incredibly supportive.  Porter’s 4th grade teachers, in particular, were hugely helpful.  The amazing Ms. Herndon prepared four months’ worth of math curriculum for us to take as home school along the way, arranged in travel-friendly packets including assessments!

At first, I didn’t intend to do much formal home school.  We used challenges like, “You have $10 US to go buy a gift from this Indonesian market for your secret santa person.  How much Rupiah is that?  Go buy something.  Remember to barter!”  The kids loved that sort of thing.

Here is a youtube link of Porter “Figuring out a currency conversion.”  

After a couple months on the road, we could tell that the kids needed some structure.  So, we designated a couple days a week as “home school days.”  The kids would be required to do some math and some writing, plus another activity they don’t do on their own.   Mia would be required to do some sort of PE, while Porter would read.  We started doing some more formal math lessons and practiced using the supplied curriculum.  I really enjoyed being my own kids’ teacher, and Porter commented that he thought he was learning a lot since there was a single adult holding him accountable.

Arithmetic races at home stay in Vietnam

Step 5 – We planned the logistics

Amy is our travel planner.  I could go on and on about how much work she did.  But, this post is not about that substantial effort.  In short, she planned the first 3 weeks including transport and lodging before we left.  For the rest of the time, we figured it out as we went.  We found out that with kids, we liked having places booked ahead, rather than just showing up and sniffing out housing.  The internet is amazing for research.  There are a myriad of excellent sites to find accommodation and travel.  Trip Advisor and individual blogs gave us lots of third-party reviews.  Generally, once a week we would sit still, preferably near a beach or pool, to plan out the next one or two weeks.     

Reflect, and celebrate

Although $20,000 is a pretty big price tag, in retrospect it seems a bargain.  We experienced so much, yet saw only a few other families traveling with kids.  I kept asking myself, “How many families are at Disneyland right now, and how much would that trip cost?”   A little more Googling finds some answers – about $1100 per day according to Hip Munk [7].  I have nothing against Disneyland, but we saw the Himalayas [1], lived with real elephants [2], ziplined hundreds of feet over the tops of a real Gibbon-inhabited forest [3], and we met real people around the world [4].  And we did it for about one-tenth the price.  Our planning made for some good living. 

Links and web references:

[1]  Nepal trekking.  Blogpost written by John Chesbrough, April 2017.

[2] Bees Elephant Adventure.  Blogpost written by Mia Chesbrough, February 2017.

[3] The Gibbon Experience – ziplining above the jungle in Laos.  Blogpost written by John Chesbrough, February 2017.

[4] People are People.  Blogpost written by John Chesbrough, January 2017.

[5]  “The Indie Traveller” – A good site with lots of detailed information about costs of travel.

[6] World Nomads Travel Insurance.  We never needed to use the services, but they got pretty good reviews.  This company was fine for us, though we never needed to use their services.  

[7]  Hip munk: How much does a Disney vacation cost?

John Chesbrough

John is a financial planner and investment manager. He, along with his business partner Elizabeth Snyder, founded, a fee-only, independent financial advisory firm called Trail Financial Planning (Trail FP) in Bellingham, WA. John and Liz enjoy working with people who care for others and their community – parents, firefighters, therapists, doctors, nurses, and teachers. They work with people by appointment. To learn more, or to schedule some time with John or Liz directly, please visit