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Jim writes an epic post on working and vacationing in Thailand.

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Hotel Reviews (w/ video): dusit D2, Chiang Mai | Amari Watergate, Bangkok | Amari Vogue, Krabi
Things to do (w/ video): 5 Cool Things To Do in Thailand
Travel homepage: TheHopkinsonReport.com/travel

Walking the walk — on the beach

Today I’m going to talk to you about something cool I just did – work remotely from Thailand. I enjoyed every aspect, from the $2 pad thai lunches to relaxing on the beach with a pina colada.

First let me set the framework, as there are two things I want to avoid (but might not be able to):
1) I don’t want this to come off as me bragging about my trip
2) I don’t want it to be a boring story about someone else’s vacation

The goal of this podcast has always been to walk the walk. Whether it’s getting a book deal, testing and reviewing a product, or building a website in 24 hours that generates income, I’ve always been about researching, doing, and communicating the results to my listeners (readers), vs. claiming to be a “guru” that only talks about goals but never reaches them.

This blog is about entrepreneurship, career development and lifestyle design, so if you aspire to take a trip like this as well, I’m going to try and give you the tips to help make it happen. There were many questions while planning my trip that I couldn’t find the answer to, so hopefully I can save you time and effort by teaching you what I had to find out the hard way.

In this post I’m going to tell you the story behind the story, but definitely go to TheHopkinsonReport.com/Thailand for quick links to my recommendations for hotels, things to do, and more, including videos and photos.

Work now, play later
For me, the long-term plan is to have a ton of money in the bank, so that I can withdraw $10,000 whenever I want and jet off to a foreign country at the drop of a hat. That would be nice right?

But that’s not quite the case yet, and in fact, quite the opposite. After leaving the safety of the corporate world, I’m trying to build and sustain a new business, and it takes a lot of hard work. I’m sure many of you listening (reading) are in the same boat.

In fact, I want to emphasize the three levels of incredibly hard work that needed to be done to make this trip happen.

There will be 7 parts:
Putting in the work
Why Thailand
When to go
Where to go
Planning your itinerary
Where to stay
What to do

1) Putting in the work

Brand building (4 years)
I launched this blog and podcast in 2008, and have been slowly and steadily building my brand ever since. This includes many years of helping people and creating content without any additional compensation at all. I worked on my writing, my speaking, my teaching, and building out a strong personal network, and now years later it has provided a foundation that is paying dividends.

If this seems daunting, don’t let it be. This is something you can start today, and the tools are there to set up a website, promote yourself, and build a business around something you’re passionate about.

Preparation (1 month)
Have you ever been to New York City in August? It’s a very different place. The weather is hot and sunny, tourists roam Central Park, and in many cases, businesses grind to a slowdown as people flee for the beaches and take weeks of vacation.

Not me. I had the anti-vacation. Working from my hot, cramped, studio apartment, I worked my butt off for the month of August. At times I worked late into the night and stayed in on the weekends to get even more work done. I hustled for side projects to have a little more spending money, developing new connections and courses such as my Improv for Business class.

Mostly, I was preparing in advance to make things easier in September. I wrote multiple articles for deadlines that would happen during my trip, and I recorded several podcasts in advance, so that all I would need to do when I was away was press the publish button. That’s the advantage of a digital lifestyle.

Working remotely (10-15 hours)
During the trip, I really tried to enjoy the time off that I had earned. Still, I estimate there was the equivalent of 1-2 full days of work that I put in over my 2 week stay. This included:
– Staying up to date on email
– A 1-hour chat session for an online course that I teach (I couldn’t help but brag on this one, as I did the video chat from the outdoor hotel pool at 7am in Bangkok, 8pm in New York)
– An email thread with a salary negotiation consulting client
– A Skype call with a business partner to try and get future travel consulting work with the country of Panama, including writing up the outline for a proposal
– Publishing 2 podcast episodes, which entailed small edits to WordPress and pushing files live via FTP
– Submitting articles to two companies I write for
– Taking photos and videos for this show, as well as recording video reviews for my hotel sponsors

[I know you feel REALLY bad for me as I work remotely by the pool]

Post-trip (20-40 hours)
Putting together this podcast, as well as a full report for my sponsors takes time and effort. Granted it’s pretty entertaining, sifting through fun photos and making a video review, but still time-consuming. My goal is to go above and beyond for this trip and deliver amazing value in order to build up my portfolio for future clients.

So as you can see, it wasn’t all fun and games, and there’s a lot of work behind the scenes that someone looking at a photo of me on the beach might not see.

2) Why Thailand?

Much like my trip to Buenos Aires back in January, everyone wanted to know why I picked Thailand. It’s actually for different reasons. The BA trip was based on hearing great things from Tim Ferriss and other entrepreneurs, the lifestyle they had there (steak and Malbec), and the time of year (I wanted someplace sunny during the NY winter).

The way this trip evolved was as follows:
– First, I had been invited to a wedding of my friends Jia and Fede in Singapore on September 16. They are the founders of short term apartment rental company Roomorama.com.
– Next, I received dozens of inquiries from people wanting to rent my apartment in NYC, and was able to lock in a couple for a 2 week stay that gave me a pretty significant amount of money to put toward my trip
– Finally, I had heard great things about Thailand, so I started researching flights and was able to piece together my itinerary based around those 2 events

The takeaway here: You need to have awareness in life when circumstances like this start to show themselves. You need to have flexibility, but take advantage and act when forces start to be working in your favor.

There will always be uncertainty in life, and I went through not weeks but months of “I’m THINKING about going to Thailand.” There was a lot of hesitation:

– Should I be going away while still building my business?
– Can I even afford this?
– Which person should I accept to stay in my apartment, and can I trust them?
– Should I go by myself or is there a friend that can come with me?
– Where do I go? When do I go? What cities to see?

Many people get stuck in this uncertainty. For a major decision like this, all of the options can paralyze you, and sadly, many people never pull the trigger, and miss out on some of the most amazing things in life… not just travel, but changing jobs, starting a new business, or getting out of a bad relationship.


But once you COMMIT to something despite uncertainty, your world opens up. It started with me accepting the offer to rent my apartment. Now that someone would be here and I knew the dates, I had no choice but to go. But this made it easier, as I was able to then structure the trip accordingly.

– I had the dates to research the best flights
– 2 friends were able to say they could not go, but 1 said yes
– I was able to sketch out the cities I wanted to see
– I was able to immerse myself in research, and find out the two best things about the area, the food and the diversity of places to go

But again, it was only after making that leap into uncertainty and fear, that things became real and fell into place.

3) When to go

If there was some downside to committing to my plan, it was that I only discovered afterward that September was not the ideal time to visit that part of the world.

Sure, I knew that the peak, driest time was November through February. And the next best time to go is March through May. So what that meant was that from May through October, was the offseason.

I see, the off season, not peak time. Then I started to see it referred to as the rainy season. OK, I get it. It rains more. But then I saw it referred to as the MONSOON season. Hold on a minute.

I really started to freak out a bit. Listen, I’ve lived in Seattle. I can handle some rain. I can handle some wind. And the temps were still going to have a low of about 75, so it wasn’t like it was cold. And when the sun DID come out, it would still be in the high 80s.

But then I started asking some people that had lived there. Was this “it’s going to rain a bit” weather, or am I a total idiot and the only tourist dumb enough to go at this time of year? Is this like going to the beach in the Hamptons or Cape Cod in the middle of winter? I saw some reports that waves could shut down boat service to some of the islands.

Here’s what we experienced: We had some days with glorious sunshine. We had some days of torrential downpours. We had some days where we had both of those within hours of each other. There were days where we got 4 hours of 90 degree weather by the pool, when the forecast predicted a 90% chance of rain. And the weather system in the north mountains is completely different than the southern beaches.

Bottom line… the weather didn’t affect the enjoyment of our trip whatsoever, the off season made things less crowded and cheaper, and trying to predict things was useless. However, if you’re planning a once in a lifetime honeymoon on the beach, yes, you probably want to go during the dry season.

4) Where to go

One of the coolest things about traveling here, were the three diverse experiences that we had.

Bangkok – A big time international city, with all that goes along with it. You’re going to get hustle and bustle, traffic, restaurants, skyscrapers, malls, things to do, and a little bit of craziness. I was blown away by the Grand Palace and the temples, but it was a little overwhelming, even for a New Yorker.

Chiang Mai – Friends raved about this city in the mountains to the north. Not only is the “old city” walled in, it’s surrounded by a moat. It seems like every resident drives a scooter, and while there are parts that can be a little gritty, I wouldn’t say I really ever felt unsafe. If anything, I wish we had more time here to explore.

Krabi and the beaches – When traveling to the south of Thailand, there are many choices and opinions. While Phuket is one of the better known destinations, more than one person I spoke with recommended skipping it, due to the tourist factor and well, let’s say “ickyness” of some of the activities there. I can’t judge because I didn’t go, but I know there are good parts, bad parts, and some great beaches to see. The island of Koh Samui is a popular destination, but I was also warned of overdeveloped tourism. In the end, we made Krabi our home base simply based on the hotel option we received.

[The sunsets cant be beat in Thailand]

5) Planning your itinerary

One of the most difficult things to do with Thailand – or any trip – is to plan the perfect itinerary. I guess it’s a difficult question to answer because there are so many variables, but I found it really really hard to get the answers I wanted.

How much time should I spend in Bangkok? Is 4 nights enough in Chiang Mai? Should we head for the islands in the Gulf of Thailand, which might be more expensive and touristy but have better weather, or opt for the ones in the Andaman Sea? Should we fly from one destination to the next, or is a train, bus, or boat a better option?

In the end, it comes down to three factors:
a) The length of your trip
b) Your budget
c) What you like to do

Obviously my 16 day trip (including Singapore) would be much different than someone staying for 6 weeks. For example, it was a no-brainer to take a $78 1-hour flight from Bangkok to Chiang Mai to save time vs. the 11 hour bus or train (I still don’t understand why it is so long… it’s 1 hour from NY to Boston, yet the bus is only 4 hours).

[When you’re continually killing time in airports, you find fun things to do to entertain yourself with your camera]

Also, a night in a 4- or 5-star hotel room for less than $50 per person seems like pocket change compared to New York rates of $600 per room. However, we met travelers staying in hostels that were only $4 per night, which obviously keeps costs at a bare minimum for a longer trip.

Here’s how I’d break it up:
– Bangkok is a major city, but a bit gritty. If your trip isn’t that long, I’d allocate anywhere from just 2 to 4 days to feel like you got a feel for it.
– We were in Chiang Mai for 4 nights and 3 full days. I wish we had at least 1 more day, but to be honest I feel I could have relaxed and stayed there for weeks. Your dollar goes very far.
– As for the rest, beaches are beaches. I feel that the length of time you could spend on a Thai beach is probably about the same as Miami beach. Are you a sun goddess that can swim every day, relax by the water, and read book after book? Then anywhere from 1 week to a month might work for you. For me, we were there about 4 days, and while I was relaxed, I think I easily could have done 4 more.

What I’ve found out in life are there are generally two types of people:
Person A) Just tell me how much money it will cost and where and when to show up
Person B) I am going to create a logistical plan more detailed than a NASA launch

Generally, the pairing of these two types of people on a trip goes very well. Want to guess which one I am? Here is my itinerary spreadsheet:

[Click the image to see full size]

6) Where to stay

Once again in full disclosure I’ll say that I had a sponsorship agreement with the hotels I am about to mention, but everything I’m about to say is the honest truth based on my experience.

Here’s the problem many people face with trying to choose a hotel in a foreign country. What I’ve found is that when you go on tripadvisor or hotels.com or any of these sites, a lot of the hotels start to look the same, with professional photos of rooms, pools, and restaurants in pristine condition.

So given so many similar choices, I find it assuring to get a second opinion from someone that has actually stayed there. That’s where social media can really shine.

In fact, that’s how I heard about these properties… the Dusit D2 appeared on my radar after TripAdvisor’s integration with Facebook indicated that my friend Cathy (a former Hopkinson Report guest) had stayed there, and I learned about the Amari chain of hotels from Chris Alford, who was on a Facebook group of avid travelers that had attended the World Domination Summit.

Here are three hotel possibilities for you to explore:

Chiang Mai – the Dusit D2
The “D2” designation stands for their second generation of hotels, which combines Thai tradition but for a new modern generation. In a way, this describes Chiang Mai itself… a city rich with Thai tradition, culture, and food, but with elements of the modern world mixed in.Read my full review of the Dusit D2.

Krabi – the Amari Vogue
After more than a week of traveling and exploring, I was more than ready to relax on the beach, and the Amari Vogue hotel did not disappoint. Read my full review of the Amari Vogue.

Bangkok – the Amari Watergate
This is a great, modern hotel in the middle of the action. Read my full review of the Amari Watergate.

7) What to do

There are so many things to do, and it all depends on what you like. For some, a week at the beach is heaven. For others, it’s boredom. The street vendors in Chiang Mai are a far cry from a 5 star restaurant in Bangkok.

Did you know, that according to Wikipedia there are more than 40,000 Buddhist Temples in Thailand?

For the shopper, there are many bargains to be had. For the adventurer, there is hiking, trekking, biking, and more. It all comes down to what you want.

Check out my Top 5 Cool Things to do in Thailand

For me, some of my actvities were Temples, Cooking Classes, Mountain Biking, Island Hopping, and visiting an Elephant Park.

8) Summary

Are you still with me? Or have you already rushed to the web to book your flight?

The bottom line is this… if you ask most people what they would do if they won the lottery and could quit their job and do anything, I think the most popular answer would be to travel the world.

But winning the lottery is just a fantasy. The reality is, if you work hard, build your brand, and put the right processes in place to be able to work remotely, it’s possible to set yourself up with a lifestyle that gives you the freedom to experience more of the world.

I’d love to help you out and show you more. Feel free to email me

Sponsor Message: Freshbooks Fresh Take of the Week:
Working from the cloud: When I was away I backed up my photos 3 ways… they were on my camera’s memory card, I backed them up to my laptop, and then in the event that both of those were lost or stolen, I copied them up to Dropbox in the cloud. Once they were there, I used the cloud even further, copying them to my iMac when I got home, and sharing directories with friends and family. The cloud is good.

Did you know more than 5 million people use Freshbook’s cloud accounting to make billing painless? It’s the service I use to track all my accounting, from billing to expenses, no matter where I am.

Switch to cloud accounting and join over 5 million people using FreshBooks to make billing painless at Freshbooks.com.

Sponsor Message: Amari Hotels.
The Amari hotel chain is a group of 13 full service hotels and resorts covering the leisure and business markets in Thailand. In full disclosure, they have been kind enough to sponsor part of my stay there.

Learn more at Amari.com.

Sponsor Message: dusitD2 Hotels.
Meanwhile in Thailand’s second largest city, Chiang Mai, I stayed at the dusitD2 hotel. Much like the city of Chiang Mai, they blend a great mix of older, traditional Thai culture with a modern twist. Full disclosure: They have been kind enough to sponsor my stay in Chiang Mai, Thailand.

Check them out at dusit.com

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