7 Realities of Working From A Tropical Island


In 2009 my life sucked, so I did what any clueless 24 year old would do: I quit my job and moved to Thailand.

Dramatic? Perhaps. But something had to change as I could see the next 30 years flashing before my eyes. Cubicles, computers, and absolutely no adventure.

That just wasn’t going to work for me.

Now 4 years later, I run a successful business, and I do it from wherever I please.

For periods during this journey, that has meant running my business from tropical islands such as Bali and Koh Phi Phi, Thailand.

That’s the dream right? Laptop, beach, passive income.

However you may (or may not) be surprised to know, that the dream of working from a tropical island isn’t all it’s cracked up to be…well, except when it is. Today I wanted to share 7 realities of working from a tropical island.

1. You Feel Like an Asshole

Have you ever been to a tropical island outside the United States? Sure the lavish resorts are beautiful, expansive and absolutely worth visiting.

But the rest of the island?

It’s home to people making less in a year than you probably make in a day.

The vast majority of tourists tune the locals out, and instead of tipping extra, become totally cheap, either because the hotel prices are already too expensive, or because they believe they’re in a third world country, where everything should be cheap.

If you want to avoid feeling like aforementioned asshole, don’t be like every other tourist. Get to know the people around you.

2. The Wi-Fi Sucks

Working on a tropical island isn’t like being back home where you migrate from coffee shop to coffee shop, working with ease.

Don’t get me wrong, you’ll still migrate, but it will be because it can take 4 or 5 spots before you find a place that has even moderately acceptable wifi.

Power outages, bandwidth limitations, and proprietors that simply don’t want you camping out could put a huge cramp in your plans for productivity.

In Phi Phi, I got banned from one bar because all I did was work. In Boracay I had to reschedule client calls due to a monsoon and internet being down on the island. In Bali, I even tried to do a video webinar. Ha. Learned my lesson on that one.

Can you make it work? Where there’s a will there’s a way, but don’t count on wifi speeds anywhere close to what you’re used to, and be prepared to plan your heavy usage during off-peak times for the island.

3. No One Else Cares…Unless You’re Selling the Dream

So you finally made it. You cleared your schedule, flew thousands of miles. You’re on the island. You’ve got your computer, and Instagram is good to go.

You’re gonna get all the mad props in the world from your friends and family from your sweet photos on the beach.

Until you don’t.

They’ll just think you’re an asshole, too.

The exception to this is if you’re selling them on the dream. I teach people specifically how to build a business that you can run from anywhere in the world – whether that’s simply working from home, or in some place more exotic.

The people who truly want that will be more engaged and interested than ever.

Everyone else? They’ll go back to checking out funny cat memes.

4. The Food and Drink Usually Suck

This, obviously, is very dependent on where you’re at. If you’re in Thailand for instance, on most of the major islands you can manage to find some pretty good Thai food. The food on just about every other island I’ve been to has been subpar at best.

Even at the big resorts, you’re simply paying 5 star prices for 2 star food much of the time.

Most people forget about this due to the spectacular views…which is probably for the best.

Drinks are even worse. You get the local pilsner, which is the same on every island I go to, and again, unless it’s at a big resort, you order a cocktail at your own peril. In Boracay earlier this year I ordered a margarita that was served warm, with a lemon and looked like yellow gatorade.

Unfortunately that’s often the rule, rather than the exception.

5. If You Want Adventure, You’ll Get It

Island life can get pretty routine.

Wake up, do some work, hit the 3 o’clock happy hour on the beach, drink til the suns down, rinse and repeat.

However, if you can avoid that cycle, adventure is sitting there waiting for you on your doorstep.

Not only, is just about everything an adventure when you’re outside your home country, but the chance to do some seriously cool stuff is all over the place.

Once I got lost on my motorbike on Bali for a couple days. I jumped off a 50 foot cliff in the Philippines. I have a scar on my foot from fire dancing in Thailand.

All of these are great stories, and are the best part of working from an island. However, a surprising amount of people don’t take advantage of these opportunities, and work just like they would if they were at home – albeit with more internet related frustrations.

If you decide island life is for you, don’t be that person.

6. It’s Can Be Way Cheaper Than You Think…Or Way More Expensive

During my time in Bali I learned that the island can be as cheap or as expensive as I want. The local warung by the place I was living had lunch for about $3, and I could get a decent meal for half that if I was willing to venture a little farther away.

Martinis at the W? $18. Rooms? $500+

When you choose to live or travel to a tropical island, it’s a little bit of “choose your own adventure.” I enjoy the $5/night bungalow just as much as a room with a couple extra zeroes tacked on. Each makes for a unique experience, and is one of the most compelling reasons to visit this type of place. The dichotomy between rich and poor, haves and have nots, and a lifestyle completely different than what you’re used to is tough to resist.

7. It’s As Good as You Want it To Be

I’ve always had a spectacular time when I’m working from an island. I prepare for the inevitable wanes in productivity and wifi, I embrace the local restaurants and people, and try and get to know as many of both as I can. I splurge with the occasional trip to a fancy resort – especially if I really do want to live out the dream of working from the beach.

Many people however, hate it.

They show up, and all of the things I’ve come to expect about island life, just piss them off.

And it’s not surprising – living on an island isn’t as glamorous as you might think. Sure, parts of it are, but if you aren’t prepared for the bugs, sunburns, sweat, sand, digestive issues, and sub par internet – you might find yourself extremely disappointed.

Oh, and for all of you thinking it, the sand is not nearly the issue you think it is. You just have to choose your “offices” carefully.