7 Steps to Becoming a Digital Nomad


In the middle of a 88-temple walking pilgrimage, I found myself talking late into the night with my host in Anan, a small city in Japan, about currency trading and digital nomad life. For me, almost 2 years after I gave up my last apartment lease, I now have remote short-term contracts and the freedom to live wherever I want, whenever I want.

It doesn’t have to be hard if we create our own luck with a bit of planning.

Self-sustaining travel boiled down to a handful of principles. Below, I’ll break it down into approaches to planning, getting the most out of travel, and figuring out a travel-work arrangement that fits you.

1. Want to travel enough to be okay with no income.

This is the essential question that will probably determine the type of traveller you are. If the ultimate answer is no, or ‘yes, only if…’ – which, by the way, is fine – you can read my solutions for people want to keep their jobs at the end of the 7 points. This post (mostly) for people who want to travel long-term and find a great career along the way.

This question is also about having the mindset to enjoy the freedom of setting up your own schedul, and going where you want, rather than worry about your dwindling savings (which is natural for those of us who work!).

A good way to start is to know your monthly expenses. That can become your base for calculating your expenses and how long your savings will last you. If you spend less after giving up your apartment and staying in hostels, even better! You can check out my digital nomad expenses spreadsheet (keep in mind our spending habits may differ). Once you’re on the road, you don’t have to worry as much as long as you know roughly how much you spend on your meals, activities, and accommodation a day.

If you’re already working, it’s like being a university student backpacking. You can give yourself a fixed period of 3, 6, 12 months (or more) before going back to a job if you need to, in the same way school semesters start. It blocks off mental space for you to relax and just soak in the freedom of going where you want to go. In my case, I had a runway of 24-36 months in my bank account, which was plenty of time to figure out my next job.

2. Have a reason before you travel.

Why do you want to travel? Is it because you want to see the world? Is it because you’ve always wanted to live in a particular country?

Knowing your reason for travelling will help you decide on a timeframe I mentioned above. Your reason will also help keep you grounded if you are getting skeptical comments from people around you, or have moments where you’re doubting yourself.

Your reason will also help you find appropriate solutions. Because I really enjoy moving from country to country every few months, I knew I could only accept opportunities that either allowed me to continue to move either because they were short term contracts, remote work, or volunteer in exchange for room and board programs like WWOOF.

3. Make your habits your home.

Once you’re on the road for a while, the excitement will begin to wear off and it becomes a part of life. You’re not going to go on an Amazon river cruise every day, and that won’t get you to self-sustaining income. Instead, you might find yourself sleeping in, puttering around in a rented Airbnb flat, and settling into a routine where you do groceries, go for a walk, maybe go to a Meetup event, and occasionally missing home and friends.

Habits and routines work just as well on the road as they do at home. It might be the gym routine, the cooking at home, the regular music gig. It may be a strict daily schedule or just a weekly list of goals – whatever works.

In all cases, make ‘work’ part of your travel routine. ‘Work’ is anything productive: keeping a regular blog, volunteering in orgnisations or projects that you can relate to, working part-time in a cafe, taking online classes, working on your personal projects. Travelling and only consuming in the long-run numbs us to even the most amazing new places. In contrast, ‘producing’ stimulates, motivates, teaches, and engages us. Ultimately, it allows us to grow and will probably lead to our next job opportunity!

4. Actively look for jobs.

Your dream travel-work arrangement may land on your lap, but it won’t fall out of the sky. As a traveller who wants a job, you are an oddball, so you need to actively pursue and create your own opportunities.

It helps if you know what you want. What industry, job roles, work environments, routines, do you want to work in? Make a list and be creative about where you hunt for them. Apart from job boards like Monster.ca, JobsDB, Glassdoor, Angelist, go after specific companies that you’re interested in. If you use social media, engage with their teams online and get to know them – you have time. If you have technical expertise from your previous industry, write some guest articles in respected websites. Many opportunities come through these informal engagements that build up trust.

5. Practice saying ‘no’ politely to say ‘yes’ instantly.

I was offered various opportunities since I left my last full-time job, and kept politely declining, even though the positions were  interesting and I was anxious about income. This goes back to points #1 and #2, where I had clear goals for travelling in 2014.

I’ve found that being completely clear and honest with your explanations when saying ‘no’ not only gains respect, but sometimes gives the other side an opportunity to give you another offer – and an almost-perfect opportunity becomes the perfect opportunity.

Saying ‘no’ to almost-perfect opportunities made it possible for me to say ‘yes’ to projects that really excited me, such as translating tea ceremony and flower arrangement pieces for 無事姐妹 (Caketrees Studio), building an online presence for 可恩廚坊 (Yan and Coco’s Bakery and Cafe) in the 2 weeks I had in Taipei, doing some groundwork with Cesar Harada on Hong Kong’s first maker space, MakerBay (check their latest Facebook updates!), and working with China’s first educational accelerator 光合空間 (LearnLab), to name a few. Because these projects interested me, the experiences and skills I learned from each of them has helped me in future opportunities.

6. Use numbers for your own projects.

Collaborations are great for learning from others, but it is always good to have a regular project on the side to keep productive in between. Set measurable project goals (daily, weekly, or monthly) to hold yourself accountable, and feel good about when looking back. It could be the hobbies you’ve wanted to try, reading x number of books, or teaching yourself skills to get to your ideal career. In my case, I wanted to work on photography and blogging, so I set myself a goal to write 1-2 short posts a week to get familiar with blogging platforms, used to writing, and also to practice my Chinese. In addition to being able to write about the people I was grateful to, I felt good about producing 50+ posts and improving my Chinese. This first blog, Living off of Kindness, laid foundations for this current blog, and led to other (paid) work offers.

7. Be flexible.

Realistically, the right job might take a while. Try different side jobs before the right one comes, or your startup goes big. Look for part-time / seasonal jobs at cafes, tutoring, or skilled a volunteering opportunities with room and board provided on Jobbatical or Moving Worlds. Alternatively, you could do house-sitting in a country you want to live in to cut living expenses while working on your projects. Be open to trying new things, and if it wasn’t a good fit, just move on.


Travel solutions for people who want to keep steady jobs:

1) Stick to shorter trips that fit your annual leave;
2) take an unpaid leave every few years;
3) Only move when you have secured work in another country. Jobs, especially in Asia, are teaching English programs.

Travel solutions for people who want to have some income along the way:

1) For those under 30, try a youth work abroad program for a year or two. Many European countries, Canada, Australia, Taiwan, and Japan have them.
2) Try Jobbatical or Moving Worlds for room-and-board and a small stipend.

For Digital Nomads:

1) Check Remote OK job directory.
2) Bootstrap and start your own company (check out this article)!

If you liked this post, check out my Freak Japan Travel Expenses and public budget sheet to see what life on the road costs!

One Comment

  1. […] Couchsurfing host in Awa City inspired during our late night conversation. He dreamed of not only becoming a digital nomad, but a digitally nomadic […]


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