Since the beginning of our journey, we have kept a watchful eye on digital, income-earning opportunities.  We accepted the risk of going an entire year without income but always intended on finding jobs on the road.  Finding remote work would not only support our travel but our long-term goal of location independence.  At the same time, spending all of our time working was not an option either. We need ample time to EXPLORE!  Needless to say, we knew that finding part-time, flexible, timezone-independent, remote work opportunities in our fields of expertise would not be a daily occurrence.  For one of us to find a job like this seemed like finding a needle in a haystack, but we both managed to find work! For personal details on our jobs, head over to our last Shanahan Quarterly, this post will focus more on the process of getting a remote job.
In this post, I want to outline everything we experienced in our journey to remote jobs. I’ll start with my personal journey, going all the way back to when I began building the skills that allowed me to get my new job.  Next, I’ll share our strategies for remote job hunting as well as links to any resources that we used. I’ll discuss our experiences interviewing for jobs remotely and end with how we balance work and travel.

Going Digital

If you seek a location independent lifestyle, you’ll need a digital job.  For some, this transition may be just a location change but I am most excited about my new job because it is my first job in this industry.  I did not go to school for programming or transition from a similar, fixed-location job. In fact, when Stef and I got married, I had pretty much no knowledge of programming at all.  Whether you desire to be location independent or not, I believe that everyone is capable of learning something new and benefitting from that knowledge. I hope my story may inspire you to start learning something new, that could help your dreams come true.  If you don’t need the inspiration and want to head straight to our job hunting experience, click here.

Getting Started

I started to teach myself computer programming about three years ago.  I had just left my job as a commodities trader and started working on some basic Python coding tutorials that my brother suggested.  A few days a week, I would sit in his living room (while he worked from home as a software developer) and work through these tutorials. When I got stuck (which was often), I’d ask him for help.  But soon Stef moved from Calgary to Denver, I got another job, and these sessions stopped. Then I got into a graduate school program for teaching.  Over the school year, school work monopolized most of my time.  However, I used the site (again suggested by my brother) as a fun escape from my school work.  This had the added benefit of continuing to build my computer programming skills.
As luck would have it, the school I would be working the following year also needed someone to teach a middle school computer science class.  Teaching the class even included a five-day programming training over the summer. This turned out to be my favorite class to teach.  In addition to teaching my students some useful skills (I hope), my own skills and enjoyment of computer programming continued to grow.  As the school year came to an end, Stef and I were already beginning to throw around the idea of traveling and location independence.

Getting Serious

Data science is currently one of the most in-demand jobs and one that can be done remotely. That summer, I decided to expand upon my Python programming skills and start an online data science program, Dataquest.  I committed all of my time to complete that course (and one other). I continued to learn more and more every day.  This lead to an “internship” opportunity with a company in India that I could do remotely while we traveled.
After six weeks in India, I can say that I absolutely love the country, but not this particular business’s practices.  Many details of the “internship” turned out to be false. The biggest of which being that it was a paid internship.  Despite never receiving any money for my work, I got the opportunity to work on some really cool projects with some awesome people from all over the world.  One of which we visited in Bengaluru, and two others we met in Delhi!

Getting a Job

Most importantly, my time teaching myself and my students, playing coding games, and the “internship” helped me land an actual paying remote job! I wanted to share this, not to boast about my accomplishments, but to share what is possible for anyone.  Three years ago, I started learning something from scratch.  I knew nothing about it. The simplest things, the things I do every day now without thinking, were confusing.  I wrote code after code that failed but just kept trying.  It was not a natural gift that I had for programming, just a commitment to learning.  Most of all, I enjoyed it.  It challenged and frustrated me, but I kept coming back to it.  Everyone can do the same. Find something you enjoy and keep working to get better at it. Like me, you’ll be shocked by your accomplishments and where you find yourself a few years down the road.

The Job Hunt

Where We Looked

Many companies, especially startups, have realized the benefits of taking their teams remote.  We did not dedicate ourselves to finding jobs when we began, but we searched the job boards on a semi-regular basis.  Our two go-to sites for remote work were RemoteOK and  These sites provide mostly startup opportunities, but larger companies will post as well. Sites like LinkedIn and Indeed work too, but more often their companies restrict remote jobs to smaller geographic areas.  We also created UpWork accounts, thinking we may be able to find some opportunities there as well. Upwork and other freelance sites typically offer shorter term, contract jobs.  This would allow us to work occasionally if we had time available. We did not ever end up working through Upwork, but my friends in India use it and Fiverr for their freelance work.
With my background as a teacher, we also strongly considered many online teaching opportunities.  Teaching English as a foreign language online continues to grow in popularity.  We have even heard other travelers teaching from adjoining rooms.  The downside to these positions for us was the hours. We were looking for opportunities with flexible hours and these typically lock you into to certain windows of time.

Unexpected Opportunities

My first money-making opportunity actually came from an unexpected source.  Amidst the plethora of junk in my email inbox, one of the weekly blasts that I rarely open had an opportunity.  It was from an online learning website, called Dataquest, and they were looking for users to write tutorials for a new side-project, Armed with the knowledge I gained from their site and writing experience from blogging here at Remote Roots, I applied. Suddenly I was spending my days exploring southern Thailand and my free time writing a tutorial. It was perfect, as I could work around our schedule. One tutorial turned to two as someone else backed out and in the end, I recouped the money I had spent on the site and put a few dollars back into our travel budget.
Stef’s skill set ended up being a perfect addition to the company her sister works for in Canada. The company was growing and not happy with the quality of candidates from their current recruiter. Stef had been recruiting people nationwide at her last job, essentially working remotely, but from her cubicle in the Denver headquarters. Stef never thought she and her sister would be conquering the real estate appraisal world together, but you just never know when and where you might add value to a company.

Interviewing for Remote Jobs

Getting an Interview

Our interview experiences have varied widely and really depend on the type of job.  Stef had the benefit of an established track record of proven performance in her industry so that really spoke for itself. Her job is also completely commission-based. Basically, a résumé and the recommendation of her sister provided all she needed to get a contract with the company. For my tutorial writing job, verifying that I had completed the companies lessons and providing a writing sample were enough to get offered a contract.  These type of jobs offer little risk to the companies since we only get paid if and when we deliver.  These typically require minimal interviewing but also do not always provide a consistent income.

Expect the interview process for hourly or salaried jobs to be much more involved.  These jobs offer considerable risk to companies, so they need to ensure they are hiring the best candidate.  I applied to many jobs via the resources above and rarely heard back. Competition is tough in the remote work world so be prepared to be rejected often.  I quickly discovered that I could not rely on my limited résumé to even get me in the door.  I found success where I had the opportunity to showcase my abilities up front.  For my software engineering job, the company required candidates to pass two online tests before considering an interview or even asking for a résumé.  This provided an opportunity to show that I could do the work, regardless of the experience on my résumé.

The Interview

After two difficult, online tests for the software engineering job, I was not sure what to expect for the phone interview. I prepared for anything but hoped I had already completed the most difficult part. No such luck! My interview took just over one grueling hour and tested all of my abilities.  It covered everything from technical topics to personality and work style.  I did my best with the technical content but did not always have an answer.  I also chose not to go into too much into detail about our travels. It is a remote job, but moving around a lot could be seen as a negative for an interviewer.  Despite the difficulty, I thought the interview went well overall. Eventually, the company decided they would feel more comfortable hiring me after a trial project.  The project was paid, so I at least was guaranteed some income at that point. Fortunately, that went well too and I began putting in my 30 hours each week starting at the end of March.

Communication, Communication, Communication

Stef and I both agree that communication comes first when trying to get a remote job. Stef now recruits specifically for remote jobs with her new company and often knows how she feels about a potential candidate long before they talk on the phone. The interview process really starts with the first written contact. Interviewers need to see you can provide concise, clear and organized information in a timely manner. Most remote jobs rely heavily on written communication, so shining here can begin to set you apart from the field. To be clear, I am not advocating that you respond to emails at any hour the night, just try to reply within 24 hours. Companies know there will likely be a delay due to time differences, so the quality of the content is most important.
The phone interview also reveals a lot about an applicant’s ability to communicate.  Communicating about work topics can be difficult over the phone. Speaking clearly about complicated topics can provide a big leg up against the competition. As I said before, I definitely did not have all the answers. Being honest and asking good questions about new topics shows an interviewer a lot.  It also gives the interviewer an opportunity to test how teachable you are. My interviewer guided me through a couple of topics, which provided an opportunity to prove that I could understand new concepts quickly.  Good communication skills for remote jobs can be even more valuable than having all the answers.

The Working Life

If you have been following along, you have probably noticed by now that Stef has been the one authoring the amazing posts of late. Due to my job requiring at least thirty hours per week, I have unfortunately needed to step back a bit. In fact, I started this post in India and I’m finally posting it five countries later.  Stef often relies on responses from others before she can begin working and has stepped up to keep the blog up to date during her free time.
Thus far, we have both adopted a much different work schedule than we had at home. We prefer to put in a few hours in the morning, then break from work and return to our work for another couple hours in the evening. This gives us most of the day to do what we want. On a typical day, I’ll log 3-4 hours when I wake up, while Stef works or blogs as well. Then we break to workout, shower, eat, and start exploring. Luckily, we have adjusted to the heat since we start wandering the wild streets of India during the hottest parts of the day. When we return, we relax (and cool off) then fire up laptops for another couple hours. I also enjoy the midday break because it allows my brain time to work through anything that had me stumped that morning.
Of course, every day is different. Some days we designate more time for work and look for a nice (aka air-conditioned) place to work. Other days we plan on exploring early to beat the heat. We absolutely love having control over our schedules. I actually worked every single day in the first two months, yet every day feels like a weekend (or at least a half day).

Making Work Work on the Road

Finding accommodations with good wifi is more important now than ever.  With our jobs, we now need a reliable connection around the clock, not just during daytime hours in our current timezone. We have found wifi available everywhere, but reliability can vary.  To assure a great connection, we consistently lean on reviews. rates the wifi at each place, which is really convenient.  For AirBnB, we dive into the personal reviews, looking for comments specifically regarding the wifi. We have our issues from time to time, I had Stef climbing the wall outside to reset our router at 5:30 am in New Delhi, but overall we have avoided any major issues.
Though we set out to see as much of the world as we could, we also appreciate spending multiple days in each location. Constant travel can be draining. Having a job has encouraged us to put more time between our travel days. Ideally, we prefer to spend four or more days in each place. This provides enough time balance seeing the sights and completing our work.  We also feel more connected to each place as we get a little more entrenched in the culture.
It can be a lot on our plates from time to time, but we would not have it any other way.  This post marks a milestone for us as well. We have meticulously tracked our finances and after seven months of travel, we made it into the black. Our income has covered the cost of all our travels and our recurring costs back home (phone, storage, etc.). We celebrated by promptly booking the next few months of our trip and plummeting back into the red, but it is nice to know that thanks to our new jobs that gap will slowly close again.

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