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Laptops in Paradise

How to Work from the Beach

Last week I found myself sitting on a remote island in Indonesia fixing some code before an afternoon of scuba diving. I've been doing projects remotely for many years, and many wonder how it's possible. Here are my tips to get there.

Before I can explain how you too can work from a remote beach at the end of the world, let’s start with some general ‘work from home’ guidance.

In most modern companies you’ll find people in a variety of roles where ongoing face-to-face collaboration isn’t really required: software development, design, writing, accounting, sales, etc. With modern communication tools like Slack and VOIP conferencing, it is now easy to stay in touch from anywhere. At times, meeting online is easier than talking IRL. I’ve frequently found myself text-messaging colleagues who sit across from me in the office, even though it’d be just as easy to talk. People join video conferences from their desks rather than get together in a conference room. There comes a point where you start to wonder whether the hour each way to commute into an office is worth the effort.

A few companies have embraced this new reality with fully distributed workforces. Automattic is one that comes to mind, and the lessons they’ve learned are well documented in Scott Berkun’s ‘A Year without Pants.’ But these companies are the still the exception rather than the rule.

The reality is that most companies still want their employees to come into an office. For good reason too; there’s a momentum that develops when a group of people come together to work on the same project. There’s also a matter of effectiveness. The reality is that when given the opportunity to work from home, most people are poorly equipped to maintain their productivity. They slip into bad habits. They check facebook more, they get caught up looking after the family, take longer lunches and so on. When left unchecked you find situations like Marissa Mayer found at Yahoo where productivity had plummeted and many people were taking advantage of the privilege.

Who Works Remotely?

Most successful examples I’ve seen of people working from home within traditional companies, are from people who’ve worked full time for a while, who’ve developed a reputation of trust, and then transition to a more remote stance. Once you can prove you get the work done from home on Fridays, you can expand from there.

There are also legions of independent contractors and online entrepreneurs who have untethered themselves from an office. Some do better than others. There are roles which are more suited to remote work, such as financial planners, legal advisors, programmers, authors, are all well suited to remote work. I even have a friend who is a medical doctor doing telemedicine from Paris. Sales and support roles, which are typically external facing, are also role that lend themselves to being remote.

But to make it work, you need to keep your momentum, and you still need to build trust, and most importantly, you need to get the work done.

Good Habits Make it Work

As a digital strategist who also codes and builds prototypes, I go through phases where I need to be collaborative, but also times when I just need to be creative, and/or get stuff done. When I’m in ‘work mode’, I really just need a quiet place without interruptions, and that might as well be anywhere. But when I need to work as part of a team then there really is nothing better than being in the same room with others.

For times when I just need to get the work done, the office can actually be a difficult place. Offices are configured for distractions. You get pulled into meetings, caught up in office politics, invited out for mid-morning coffees. And then there is the wasted time every day just commuting back and forth.

But home has it’s distractions too. There’s the laundry, grocery runs, there’s family and friends passing by and worst of all, there’s less schedule and framework to your day.

In this environment, it’s important to have good habits so you can maintain structure. Self-discipline doesn’t work. Habits do.

Plan Your Day

I try and plan my day the night before. I try to start work every day at roughly the same time – usually around 8:30am, and I try and follow a regular schedule. For me, a method I’ve found that works is to break the day up into four chunks of roughly an hour and a half. I have an idea of what I hope to achieve in each of those blocks, and I keep my eye on the one thing that is most important for the day.

Dress Up

I dress more smartly on work days, even when I’m not going anywhere. I have a separate office in my home to work from and I never work from bed. I’ll also take a morning walk to get some fresh air before I start my day. (It turns out a commute has it’s benefits, even if you return to where you start)

Enjoy an Afternoon Nap

Then there are aspects of working remotely that are absolutely productivity improvements. For me, I’ve found an afternoon nap to be a tremendous boost to my second half productivity and well being. After lunch, I often feel tired. Sometimes, my head just feels full. It’s really wonderful to have the flexibility and freedom from judgement to be able to lie on the couch and close my eyes for 30 minutes.


One important lesson I’ve learned again recently is the importance of over-communicating with your clients (or your boss). When you’re working from home, no-one can see you working, and they can’t see what you’re doing. This can feel like a good thing at the time, but it opens up room for distrust, and worse still, it opens up room for errors. The regular ‘peek over the shoulder’ is a healthy activity; it’s important not to go too far without feedback, and as a remote worker, it’s essential to check in frequently and often, ask questions – even when you don’t really need too, and demonstrate small wins along the way.

Messaging tools, skype, google chat, slack, all make this easier. There’s also nothing better than a video chat. I like to launch these quickly and often and use them liberally in place of a conversation. Start with some messaging back and forth, and if you’re discussing something meaningful, hit the call button.

Working from the beach?

Let me stress this. The secret to being able to work from the beach is being able to work productively from home first. Once you get on a plane to somewhere new, things get much, much more complicated. Your schedule gets thrown off, your routine becomes interrupted, you’re in a different time zone, your healthy breakfast with fresh roasted coffee is no longer available, and the wi-fi signal is spotty. Even your habit of dressing up in the morning is no longer appropriate.

And no matter how you frame it, the perception of your colleagues is liable to change from ‘working from home’, to ‘being on vacation’. If you take a week off and go to Hawaii with a plan to work too, everyone is going to assume you’re really just on holiday – even if you bust it out while you’re there. (I tried this once, and it was the most frustrating week ever.)

But if you follow a few principles, it is possible.

First and most importantly, you have to slow your travel waaaay down. You can’t go to Europe for a couple weeks, and expect you’ll be able to crank out good work in the evenings and take train rides between cities and go sightseeing. It just doesn’t work like that. Travel planning takes a huge amount of time. Flights, trains and buses all take time and tremendous mental bandwidth. There’s just not enough time to be moving around, doing things, and working in one day.

But I have found it is possible to go somewhere new, hole up in a quiet AirBnB for a week, and take few hours off each day to do something new and interesting. You can do this at the beach, or you can do this in a city. The key is in not planning too much.

Case in point: I’m writing this from Surabaya in Indonesia. My goal this week is to make improvements to my personal website. I have a room at a 3-star hotel with a breakfast buffet. I’ve found a nearby swimming pool and have gone there for my morning workouts. I get stuff done early in the morning, and by 4pm, I shut down and head out to walk around. Today my only travel plan is to find a post office so I can mail a letter. Maybe I’ll see a few interesting things along the way. Tomorrow, I plan to find a co-working space. I’ll leave at the end of the week, and I won’t have ‘seen’ the sights of Surabaya, but I will have ‘experienced’ a side of it.

Even better is to go somewhere for a full month and stay there long enough to make a few friends and become familiar with the place. Even after a month you’ll only have scratched the surface, but it’s long enough to start the transition from vacationing while working, to living somewhere new and working.

I find it’s also critical that you don’t travel with a friend or significant other unless they’re working too. I’ve found it impossible to be productive when you also have a friend who wants to get out and explore. Again, know when you’re on holiday, and know when you’re working, and don’t try and do them both at the same time.

When you’re traveling, the good habits you developed at home will become even more valuable. Seeking out exercise, planning your day, setting aside time are all essential. If I’m moving to someplace new, I’ll aim to travel on weekends, and be in one place during the week. The 5 day work week is a good model, and it gives a couple days off for doing fun things too. Over the course of a month this gives you at least 8 days of vacation someplace new, as I did working remotely from the middle east in 2008

I spent an enjoyable couple weeks working from Cairo before the Arab Spring. Every day, I would get out for a few hours and explore a new part of the city. I found a local hangout, made friends, and saw some amazing things. And I got the work done.

For some people, being a ‘tech-nomad’ is a full-time thing, but it doesn’t have to be. For me it’s a twice a year thing…. I’ll combine a couple weeks working remotely with a little bit of holiday. It’s nice to have the flexibility to experience ‘living‘ in a few new places for a while, but there’s no place like home.


After all this, there comes some a few practicalities to make it work.

Internet Access.

For me, internet is like water. Without it, I can’t do any work. I’ve found it to be a nightmare to rely on coffee shops and hotels to get you access. Fortunately in 2020 with 4G data, you never have to. At almost any airport around the world, you can buy a local SIM card the minute you arrive. In Europe and across Asia, it’s easy to get a local phone number with 10-20GB of data for around $20. This is much more affordable to roaming on your home number, especially if you’re from the US. It also gets you a local number for communicating with people you meet.

Internet connectivity is now widely available even in remote places, but check before you go. Last week I was in Western Papua where the cover photo was taken, line of sight to a cell tower, getting 16Mbps downloads.

Phone Calls and Text

I usually travel with two phones. One I’ll leave with my US number, and enable wi-fi calling. I’ll tether that to my local phone with its affordable data plan. Text-messages and phone calls are still the default medium for a lot of people from home to reach you, but data connections are now good enough for great phone calls. I’ll often sound better calling in over IP from the Philippines than I would over the phone system at home.


Let’s be honest. Coffee shops aren’t the best. When I want to get stuff done, I find an obscure hotel or AirBnB and hole up there for a week. I sometimes think I should seek out co-working spaces more, but when I want to get work done, I’m trying to avoid distractions, not add to them.

Time Zones

Time zones can play to your advantage, or they can catch you out. Figuring them out is part of the game. I find it’s important to be available to co-workers when they’re around. Working on the east coast or Europe, I’ll aim to have my fun in the morning, and be working by noon, knowing that I won’t be finished until late. On my trips to Asia, I’ll take drastic steps to alter my schedule aiming to be in bed by 7pm so I can be up at 2am…. this is really easy to do if you start when you get off the plane, but it’s a bear if you have to back into it after you’re acclimatized.

When I’m in Hawaii, it always feels like I’m playing catch up. In Europe I’m often lulled into complacency knowing that it’s 8 hours before everyone else wakes up.

Is it worth it?

The freedom to travel while working is one of the reasons I continue to do what I do and live how I live. I love experiencing new places and cultures, and I wouldn’t get to do this if I could only do it on vacation. I also find being in new places provides me with inspiration and opens me to new ideas. It makes me a better person to experience things from new perspectives, and to be forced into new routines. Funnily enough, I also find being disconnected from the distractions of home to be quite liberating too. Without having to fix my car, meet up with friends, take the dog for a walk, there are many new hours in my week.

Working remotely can be done, and it can be done well. It’s well worth the effort if you can master it.

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