Packing: What I Bring to Thailand

If you’re moving to Southeast Asia, and especially to Thailand, then you’re going to get a lot from this page.  

There are things that are quite difficult (if not expensive) to get here in Thailand, and then there are other things that were easy to get here in Thailand – that I wasted precious luggage space bringing over from the U.S.  I further ranked these things based on ease/difficulty to find in Thailand as well as storage space.

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Vipassana: What I learned in silent meditation

It’s one thing to meditate daily.  It’s quite another to do vipassana – a silent meditation retreat – for days.  What comes up for you if you cannot be on your phone, cannot speak to another, cannot read or write, cannot exercise – so that you are still – for days?  

This post shares my experiences with two vipassana retreats I did last year, what I learned from them, and some advice on how to plan for and fully experience one yourself.

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Visa: What visa I have in Thailand

VisaWhat visa do you have in Thailand?

My visa is the non-immigrant “O” guardian visa.  It is a long-term visa that allows me to stay in Thailand for one year, as long as my child attends international school here.  Hence, the “guardian” role that I play, parenting my child.  

Technically, the visa allows me (and my child) to stay in Thailand for 90 days, at which point I applied for a visa extension for one year.  Even with the one year extension, though, I have to report to Immigration every 90 days (but I circumvent this by traveling every quarter; more on this below).

This post covers the benefits of a long-term visa, benefits of the non-immigrant “O” guardian visa, and some lessons learned on how I obtained the visa.

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Friends: How I make friends in Thailand

“That’s crazy – you moved to Thailand without knowing anyone?!”

I guess it does sound a little crazy, if not irresponsible, to move half way around the world to a country where I didn’t know anyone.  It’s been over two decades since I lived in Thailand – and suffice it to say, I lost touch with my friends here.  I have met a few people – in my MBA, in my career – who lived in Thailand, but no one who is still living here, let alone in Chiang Mai.

This post is about how an introvert like me has made a conscious effort – and several mistakes along the way – in making friends here.  I’ll organize this post based on the sources (where) I was able to make friends – giving a rating (1 being difficulty for me to find friends; 4 being easy) – and highlighting some advice along the way:

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Therapy: Who I partner with on navigating my mid-life crisis

This post discusses why I believe therapy was critical for me during the past five years – and how my therapists have guided me in making the right life decisions.  I have broken up this post into three parts – one for each therapist and the decision s/he helped me through.

Note: To protect the confidentiality of my therapists, I’m going to use pseudonyms.    

Part 1: Shawn – “Why am I stuck?”
Cognitive behavioral therapy.  Dallas, Texas.  $150 per session (60 min).    

In 2020 – prior to the pandemic – I was feeling stuck in my life.  I felt this lack of meaning in what I did, lack of connection with who I was with, and this sense that I wasn’t on the right path.  I didn’t know what the root cause for my ‘stuckness’ was – my wife?  my job?  myself?  I was contemplating big decisions – separate/divorce my wife, resign from my job, etc. – and I knew that I needed to vet these decisions with a professional before pulling any trigger.  I interviewed several therapists to see if they could help – in search of men, older than me, with a track record of helping other men navigate their mid-life crises.

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Fitness: How I keep fit in Chiang Mai

Being stronger and fitter was one of my priorities during my mini retirement.  And there are a plethora of opportunities to do so in Chiang Mai.  So how did I choose which activities and routines to adopt?  

This post discusses what works/worked for my fitness.  I break up my fitness priorities into three categories: 1) strength, 2) cardio, and 3) mobility.  For each category, I’ll outline what I currently do to stay fit as well as other options I tried out.

Strength

For most of my life, I have been a skinny, lanky guy.  While growing up, my parents would say I didn’t eat enough.  During grade school, I adopted a nickname “stickboy” (for better or worse – I embraced it, using the nickname for my screen name on AOL, eBay, and other platforms).  The mini-retirement afforded me plenty of time to explore whether I can put on more muscle.  While having a healthy, high-caloric diet was critical in muscle gain, I won’t be discussing my diet on this post – but instead where I went for my strength training.

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Happiness: Why I am happier in Chiang Mai

My definition of happiness has changed over the years.  In my 20s, I thought it was “heart beats” – the number of moments I felt alive and present.  In my 30s, I felt it was work success, as well as warmth and security for my family.  Now in my 40s, I agree with what Arthur Brooks talks about in Strength to Strength – that: 

Happiness = Have / Want   

The more I have, the happier I would be.  But the more I want, the less happy I would be.  What I have and what I want go well beyond material possessions.  I measure what I have as:

Have = f (Connections, Purpose, Freedom, Self Love)current

Want = f (Connections, Purpose, Freedom, Self Love)potential

Connections are the depth, not breadth, of my relationships.  Do I have meaningful connections with others grounded in love, truth, and compassion?  Purpose is the fulfillment of how I spend my time.  Do I spend my time that has a positive impact on others and on myself?  Freedom is the ability to control my destiny – doing what I want when I want how I want with whom I want.  Do I have the choice and resources to shape my own future?  And Self Love is how well I take care of myself: physically, intellectually, emotionally, spiritually.  Do I fully accept and love myself, cultivating the best version of myself?

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Day in the Life: How I spend the day in Chiang Mai

“Now that you don’t work, what do you do all day?”

I get this question a lot.  Freedom is a double edged sword.  Yes, I get to do what I want to do.  But it requires some effort to fill all of this newfound time I have gotten back in mini-retirement.  It’s the easiest thing to just fill all of this time with Netflix binging or Thai massages.  And for the few first months, after getting settled in Chiang Mai, there was plenty of time I put in on both Netflix and at various massage places across the city.  But I didn’t get any closer to some of the goals I had, such as learning a new language or becoming healthier.  

Here’s a glimpse of – one and a half years in mini retirement – what the typical day in the life of Lester T is:

5:45am – Wake up: I meditate for 15 min (a habit I picked up from a vipassana retreat).  I journal (blogger).  I listen to a short self-recorded affirmation.  Only after taking medications/vitamins, brushing my teeth, etc. do I check my phone.  Then I prepare a light breakfast at home: oats, peanut butter, cashews, and honey.  

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Quality of Life: How life is better in Chiang Mai

I chose Chiang Mai because of the high quality of life at a low cost.  

In my prior post, I showed how much it costs to live in Chiang Mai – and how the costs are much lower than in the U.S. for the quality of life you have in Thailand.  This post discusses how I define quality of life, and why I think Chiang Mai has the best quality of life I have seen of a city.  

I’ll break up quality of life into separate categories that matter the most to me and my family, in alphabetical order: 1) Climate; 2) Culture; 3) Getting Around; 4) Health Care; 5) Safety; and 6) Schools. For each of these categories, I provide a rating on a scale of 1 to 4, 1 being negative quality of life and 4 being positive quality of life.

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Funding Retirement: How I live on 100% passive income

I pay for my family’s cost of living in Thailand using two sources: 1) deferred compensation from my prior job and 2) cash withdrawals from my investment portfolio.  My 2023 income from deferred compensation actually paid for all of the living expenses in Thailand, while the investment portfolio grew substantially.  In other words, I am actually growing my wealth in mini-retirement!  In this post, I intend to show how I was able to do this with my two sources of income.

First Income Source: Deferred Compensation

Almost a decade ago, I sat down with the Director of Compensation at my prior company.  She described a benefit that I had as an executive: a SERP.  She went on to explain that it’s a way to defer my compensation and reduce my tax exposure.  At the time, I did not enroll in the benefit, thinking, ‘why in the world would I want to defer my pay?  Didn’t Finance 101 say that money now is more valuable than money later?”  But after seeing the effect that taxes had on my take-home pay, I reconsidered.  Now mini-retired in Chiang Mai, I am very thankful for enrolling in this program and saving as much as I did before I resigned from my prior company.  

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