Gone Learning

6 Steps to Successfully Work and Travel

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Kat Smith
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Working remotely has honestly been a dream come true. The moment you get a job that allows you to work from everywhere- and you actually take advantage of it- it’ll be hard to go back to office life.

Making the transition to remote work does come with some hurdles, don’t worry though, keep reading and I’ll help you jump right over them. It takes patience and effort to make a smooth transition and figure out how exactly it will work for you.

Just like most lifestyles, the work and travel one looks a little bit different to each person and that’s the beauty of it.

You can adjust the lifestyle to fit your wants, needs, and job to make a perfect match. Some people prefer to work and travel from a van, others only want the ability to work from a different country than their employers or clients. For some, they’ll work only a few hours in the morning or late at night and others might even work more hours than before but from coffee shops and coworking spaces scattered around the world.

Whatever personal preferences you might have, I’m going to walk you through the 6 basic steps that will help you successfully work and travel. From there, feel free to adjust it to you. 

TL:DR? Don’t worry, my husband and I combined our years of experience working and traveling into an hour-long course on Skillshare. Get this information plus way more in video format so you can sit back, relax and let us guide you through the process from your sofa. If you’ve never used Skillshare before, you can watch our course plus any other on the platform for free for 2 months!
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Step 1. Get a remote job

Let’s get the elephant in the room out of the way first- you’ll need to figure out the “work” part to go along with “and travel.” If you already have a remote job, go ahead and skip to Step 2.

For the rest of us, these days, more and more jobs can be done remotely than ever before. You’ll first need to decide if you want to work remotely from an established company as a full-time employee, work as a freelancer or start your own business, as I did with Girls Gone Working all thanks to Wired Creatives (check out their review here!).

If you’d prefer something more stable, I’d first check with your boss to see if it’s possible for you to do your current job remotely. From there, based on your qualifications and skills, it’s time to hit the job search! Check out these 7 platforms to find remote work.

For freelancers, it’s first important that you have a skill that can be delivered digitally. My husband is a UI/UX designer and has been embracing the work and travel lifestyle for the past 6 years. He finds most of his clients through word of mouth and websites like LinkedIn, Dribbble and WeWorkRemotely

If you’re still trying to find out what job might suit you, check out these guides about becoming a remote video editor, managing podcasts from anywhere, teaching English online or working as a life coach.

A woman working on a laptop in front of a window displaying a street in Da Nang, Vietnam
Sometimes I keep my setup simple to pop around to cafes

Step 2. Decide where you want to go

Here’s where your freedom of choice really comes into play.

As a remote worker, you have full control over your lifestyle, so long as you have internet! You could choose to live in a van and travel around your home country or buy a sailboat and live marina to marina. You could embrace the nomad lifestyle and hop from one country to another at your own pace or you could pick a city on the map that you’ve always been curious about and settle down there.

Each one of these options comes with pros and cons so it’s up to you to decide which excites you the most.

If you choose to live and work from a van or a sailboat, you’ll have complete freedom of where you go next but you’ll have to sacrifice things like the perfect workspace. Most likely you’ll be working from your bed or a smaller space than maybe you’d prefer.

As a jet setting nomad, you’ll get to see a lot more of the world than most but balancing work and travel while on a limited time span in each country can be exhausting. From experience, if you want this one to work, I’d suggest staying for a few weeks or months in each stop to give yourself plenty of time.

Check out this list of 18 best countries to live and work from to get some inspiration.

Or you can do what I prefer, picking a city to build a home base from for a year or longer. Personally, I love staying in 1 place for a long period of time to really get to know it beyond the surface level. I tend to choose cities with airports so we can still go on weekend or month-long getaways to neighboring countries. The con of this lifestyle is figuring out visas that will allow you to stay.

Step 3. Make a plan

Honestly, I’m quite OCD and love a good plan, at least when it comes to work. I’m a notoriously terrible planner when it comes to trips!

Having a work plan will keep you focused and might help you decide where you want to go if you’re having trouble deciding.

Based on your job, you might have the freedom to make your own schedule or you could be locked into certain hours throughout the day. If you’re locked in, keep in mind time zones when planning where you go so you don’t end up working all night, unless you’re into that.

If you have the freedom to create your own schedule, here’s where planning really comes into play. You first need to decide what time of the day you work best. No need to commit to typical working hours if it doesn’t work for you. Personally, I’m most motivated in the mornings. I like to wake up early, get some exercise in and a filling breakfast and start working with my morning cup of coffee.

My husband though, is most focused at nights. He likes to have slow mornings and really gets going after lunch. At that time though, I’m usually pretty tired and prefer doing small, mundane tasks.

A smiling woman in a coffee shop with a closed computer in front of her getting ready to start her day of remote work
Getting ready to start a busy day of remote work



If you don’t know yet what time of the day you’re most productive, test out different schedules for a week or two at a time and take notes as to how you feel and when you get your best work done.

Once you’ve decided what hours you prefer to work, stick with it! Have a clear start and stop time because now that you don’t work from an office, there is no one holding you accountable for your time. It’s really easy to get lazy and not start on time or equally, get in the zone and not turn off until hours past your cut off time.

A comfortable balance is key to get you to enjoy the work and travel sides of the coin.

Step 4. Invest in some work gear

A big part of setting yourself up for remote success is getting the right gear to keep you comfortable and working efficiently.

Here’s a list of products we personally use and love:

  1. A lightweight computer. I use the Surface Pro and Raf, my husband, loves his Surface Book.
  2. A laptop stand (keep in mind this won’t work with the Surface Pro)
  3. An ergonomic mouse and keyboard.
  4. Noise cancelling headphones. I like these from TaoTronics but Raf prefers Sony's for ultimate noise cancellation.
  5. A phone stand.
  6. A good carry-on backpack that fits everything. I couldn't find my exact bag but this one is pretty close and looks even better!
  7. If you really want to get fancy, you can even get a portable second screen to boost productivity on the go.

Step 5. 5 best practices for working remotely

Using these best practices every day while working remotely will keep you focused, motivated and finishing your to-do list to give you the time to enjoy your new city.

1. Time block your day with the Pomodoro Method

The Pomodoro Method is a technique all about utilizing short bursts of highly focused work. In the traditional method, you'd set a timer for 25 minutes, set a specific goal that can be completed in that time frame, remove all distractions, set the timer and get it done. When the timer rings you drop the pencil and take a 5 minute break. You continue to do this throughout your day.

Personally, 25 minutes is too short a time span for me so I like to set my timer to 50 minutes instead and take closer to 7-10 minute breaks.

2. Be comfortable at your work space

Know who you are and what environment you feel more comfortable and productive at.

Do you prefer to work from home (or your hotel)? Or would you rather get out of the house and go to a coffee shop or coworking space?

Personally, I like getting out and going to coffee shops but Raf works his best from home. Neither answer is correct, it'll depend completely on you!

If you prefer to stay home, designate a place where you're going to work. And yes, I know not everyone can afford to rent an AirBnB with an office but if you can, think no more. Do it. But if you can't, make sure you choose accommodation that gives you somewhere to work other than the bed or sofa. This will help you get in the mindset of "When I'm here, I'm working".

3. Send your team 2 daily reports (if working with others)

Over-communication is key to successfully working with a remote team. It’s easy to completely disappear from the radar when working from home or any other remote place, so you have to actively fight against it as efficiently as possible. Simply make it a habit to send this message everyday at the start of your day:

"Hey team, today I’m going to work on X, just FYI."

And at the end of the day, send over a quick report. This shouldn't take more than 2 minutes for you to write.

"This is what I did today: Bam. This is what I plan to do tomorrow: Bam. This I need help with: Bam."

 Make this a routine and if you do this right, everything else will follow and you and your team won't waste time chasing each other.

4. Make daily and weekly to-do lists on Sunday evenings (especially if working for yourself)

There are a million different apps these days to make a virtual to-do but personally, I'm old fashion and prefer using pen and paper. There's something a bit more concrete when writing a task down and even more rewarding when you physically cross it off your list. Also, a physical list you can keep right in front of you so it's harder to ignore than a virtual one.

I like to write a big to-do list of things I'd like to accomplish each week or month and then break each goal down into smaller actionable tasks. I use those small tasks to fill up my daily to-do lists. It can get overwhelming deciding what to do each day if you only have big goals in front of you.

Lastly, I suggest only giving yourself 2-3 tasks to finish each day to keep it more realistic. You can have a "bonus" list on the side if you have time but make those 2-3 things your priority.

5. Build a routine to get your day started off right

Having a (morning) routine makes all the difference for starting my day off on the right foot. You no longer have that commute time to get yourself going but instead of rolling over and opening up your computer, build yourself a new commute, if you will.

  1. Set your alarm and listen to it.
  2. Move your body- anything to actively wake you up!
  3. Set a time to start working and stick to it.
  4. Have your designated workspace clear (or plan what coffee shop you'd like to go to the night before).
  5. Eat a filling breakfast.
  6. Make that coffee and get going!
A woman at a coffee shop using her phone with her computer open in front of her and a coffee
Running Girls Gone Working typically means balancing a lot at once

Step 6. Don’t forget about money!

Although I’m putting this at Step 6, I’d suggest incorporating this at all the steps along the way. If you’re working full-time with a company, you’ll know your monthly and yearly salary. This cuts out of the guessing game and will help you when deciding your “where” based on what kind of lifestyle you can afford.

For those of us that work freelance or are entrepreneurs, saving will be your best friend. With this kind of work, it’s really hard to know exactly how much money you’ll make each month, especially in the beginning. You’ll want to have money in the bank to help get you through those slow months without having to worry.

Plus, being smart about savings can also mean a lot more travel throughout the year!

And don’t forget about all adults worst enemy- taxes. Again, if you work for a company as a full-time employee, not much about your tax situation will change but if you’re switching to self-employed, the taxes (at least for American citizens) are more comprehensive. I’d suggest Greenback Expat Tax Services for any American living abroad to file your taxes, stress free.

Want more? We've got you covered! Get this info plus way more in video format on Skillshare. If you’ve never used Skillshare before, you can watch our course plus any other on the platform for free for 2 months! In this course, we walk you through way more details about making the transition to remote work. We cover the expectations, challenges and far more best practices for you to fully embrace your new lifestyle!

And lastly, don't forget, you're fully capable of living the work and travel lifestyle. Shake off the doubts, put in the work and get after it!


xx,
Kat

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