From Denver to Living and Working Remotely across 50 Countries

1. Hey, can you please introduce yourself?

I’m Reid! I was born in Denver, Colorado in the USA but I no longer feel like much of an American because for the past four years I’ve been living and working internationally, remotely across 50 countries. I’m happiest when I’m barefoot, ignorant of US media, politics and culture, eating watermelon, or on a plane flying to somewhere I’ve never been before 😃

During this time I have been working as a Voodoo Sorcerer for an international logistics company based in Denver Colorado. I created that professional title myself because people who do not make software, unfortunately, see the process as rather boring. However, making software is really interesting and creative! So a Voodoo Sorcerer is one of those people delving into those mysterious arts of computorial prestidigitation that most people would rather not. It is a fun way to start a conversation with someone who has already decided (historically) that what I do for work is boring; otherwise, that conversation would never start.

2. What motivated you to choose remote working?

Prior to 2015 I had spent 12 years working in office cubicles during which work and life was a repetitive routine that felt unfulfilling.

Would this be my life for the next 30 years until I could finally begin living it on my terms, post-retirement? No way I could last that long.

Five years ago I stumbled upon a startup company named Remote Year, which was the catalyst that launched my remote life. The company functions as a concierge service to handle the burdens of locating accommodation, booking flights and securing workspaces in an effort to help transition on-site workers to becoming location independent while travelling the world.

The cost each month was less expensive than living my regular, conventional life and on top of that it came with the benefit of living in international destinations. At that point in my life I had traveled to 23 countries – but being able to travel while working – I knew I had to do it. I joined Remote Year’s initial program to travel, live and work for a year across 12 countries with 70 other people. Since then Remote Year has launched over 50 programs and I’ve continued to travel and work remotely, albeit solo.

3. What were your initial months like? Did it live up to your expectations?

When I first left my on-site life, I owned a house, two cars and a dog . Ironically, the process of transitioning from that life to become remote-friendly was much more difficult than actually living and working internationally and remotely 🙄.

It took a while to realize that comforts (aka stuff) I had previously surrounded myself with were also barriers to my freedom.

The increasing trend of minimalism sweeping the world is well learned by living and working as a nomad. I still own the home, but rent it out fully furnished. My dog, Rodeo, lives with my Dad now and I kept one of the cars in storage because, well I guess I’m not completely a minimalist yet – I really love that car.

The new patterns of remote life and work are easy to learn with tools like Google Maps, Google Translate, Skype, Airbnb, ATMs, credit cards that facilitate foreign transactions, email and web chat – it is really simple to travel, live and work outside of your home country these days. Most domestic mobile phone carriers support international calling, wifi is everywhere and videoconferencing has been around long enough that it isn’t weird anymore. Public transportation and Uber with urban living absolve you the obligation of owning a car, which to me, a Denverite, was perhaps my favorite part. I didn’t realize that needing a car to live in America is really a pain until I didn’t need one anymore.

The challenging parts of transitioning were really just annoyances: finding a gym to use each time I switched cities, knowing what and what not to pack, requisite kitchen shopping subsequent to each arrival (I have abandoned a lot of half-empty bottles of olive oil over the years) – annoying. Adjusting to local cultures and idiosyncrasies was both challenging and fun (this is a reason we love travel, right?).

4. How did you find remote working roles?

Prior to going remote, I had been at my current company for a year and a half. During that time I drove processes and tooling to support remote collaboration, management and transparency; my co-workers trusted me and things worked great. Our team and deliverables didn’t miss a beat, as expected 😎.

One thing that I was proud of is that a team member who was onsite moved to a different state and began working fully remote after I did. I think it’s testament to the fact that I was working for the right company; they trusted us and valued our skills and were open-minded to testing the theory that remote work could be effective.

I often hear stories of companies that decline an employee’s request to be remote. In such cases it is clear to me that that company does not value the employee or their skills. To be clear, it is a reflection that the company has not learned to effectively utilize a valuable employee from beyond a grabbable distance.

5. What have been the best, good and worst aspects of remote working for you?

Freedom, of course, is the best. In July and August I was in Ukraine, Serbia, Poland and Latvia. I’m in Croatia now, on the Dalmatian coast writing from the workspace that I use here. I walked here barefoot after swimming in the sea (the water is 20 Celsius here in late October) and taking a nap in the sunshine. I suppose I should mention that today is a Sunday.

I leave to go to Seoul, South Korea in a week where the weather is cold, I will be taking the subway every day and I will be eating copious amounts of barbeque. It can feel at times that I live multiple lives within one. 

Another benefit over a conventional life is I remember being so drained from the work week that I had little energy or desire to live my life. All of a sudden ten years of my life vanished. Breaking that cycle has been immensely cathartic.

A negative aspect is that while I find myself in some amazing places when I’m not on vacation – I’m working. However, this is a great motivator to be productive so that I can get the work done and go enjoy what the destination has to offer. Earlier this year I was working from French Polynesia – the islands of Tahiti, Moorea and Bora Bora. Because of the time difference, my workday started each morning at 3:30 AM with a 4:15 AM conference call. The good news is that I was finished by lunch and would walk to the beach to snorkel with schools of fish among brightly colored coral in the most beautiful water I have ever seen. Really, I felt very privileged to wake up at 3:30 AM. 

You also learn to maximize your weekends. While I was living in Santiago, Chile, I did a three-day trip to Easter Island. Being able to check off bucket list items while living a normal life feels like a video-game cheat code to life.

6. What tools do you swear by while working remotely?

I’ll speak on physical tools first. I have a Roost laptop stand which I never am not using – it helps keep my posture upright while working and has a very elegant design that collapses in between home and office. Along with that I have a wireless keyboard and mouse that are so small and light that it feels like I have the world’s most efficient, lightweight digital workstation in my backpack. As for my backpack, I love my Timbuk2 brand bag 😍. There are a lot of very dorky digital nomad backpacks out there, the size of carry on luggage, and I like mine because it is a normal backpack that fits my gear well.

One digital service I get value out of is Travelling Mailbox – it provides a conventional mailing address that accepts incoming mail in your name and then scans it to the cloud. From there you can read it, download it and even forward the mail anywhere in the world.

A tax accountant is very handy. As American expats, we have the privilege of qualifying for both federal and state Foreign Earned Income Exclusion (FEIE) tax benefits.

Essentially this allows the first $100,000 you earn to be tax-free if you remain out of the USA for 330/365 days of the year. I love my CPA and he facilitates my simple quarterly and EOY tax filing; so if you would like a referral, please reach out to me.

A tool I do not recommend: I started travelling with additional, portable monitors because I thought I needed them (previously I worked with three screens on a desktop computer). After a couple of months though I found myself adjusting and preferring a single laptop display — the additional monitors were a crutch and a burden to travel with. Nomadic travel is a skill, like any other, and as you improve it you learn to do more with less. I generally live by the axiom that the ideal is achieved where nothing remains to be removed.

As for software tools I use VSCode, Visual Studio, SQL Server 2018, Notepad++, Azure dev Ops do get most of my work done. My team uses Skype for business, Office365, Zoom and Slack for internal communication. There are so many tools out there these days and they are all fine. The tools stopped being a limiting factor to enable remote work years ago — now it is the actual communication.

7. Your most exciting/ hilarious experience since you started working remotely.

This would have to be the three months in the winter of 2017 when two other digital nomad friends and I rented a ski chalet in the Swiss Alps for the winter ski season. The chalet was ski-in, ski-out which means from the doorstep we could access the slopes. It also had a hot tub and sauna. There was an 8-hour time difference between the US time zone I work with so that my friends and I could ski during the morning and early afternoon before returning home for work and meetings. We had other digital nomad friends visiting us throughout the winter to ski and work. It was a great winter.

Something a traveller will often advise is to avoid setting expectations – it usually leads to disappointment. Well, I broke this modus operandi here in Croatia just last week. I was in need of some pants for my next destination, so I went to a local mall and bought two pairs of Levis. Back in the US these are some of the least expensive pants you can buy; but here in Croatia they are a luxury item — two pairs costing $225 USD. So now I am the not-so-proud owner of some fancy pants. Sure I could have NOT bought them, or returned them. But then I’d still have to shop for pants. And I hate shopping. These fancy pants will serve as a reminder to myself not to set expectations and also that I hate shopping. I often make mistakes while travelling – but never the same one twice 😤.

8. What is your golden advice to a new remote worker?

I’ll speak also to those attempting to become remote because it is a difficult transition and I find they often appreciate encouragement. Very few people are born into an environment that suits them best; some people never realize where they live inhibits their happiness. Zebras don’t belong in zoos and I believe humans don’t belong in offices. Finding places that energize, excite and promote your happiness and productivity is a key ingredient to any recipe of a life well-lived 😌

If you already have the privilege to work from home, kick it up a notch. Work from anywhere. Challenge your comfort zone to discover possibilities you haven’t yet explored. What do you think it would be like to visit and work from a different city for a week? Or a month? What about a new country? Or twelve? 

Imagine the version of yourself that lives such a life. What will that person be like in one year? Will have experienced, learned and grown more? I know for myself the answer continues to be a “yes.”

9. How do you see your career shaping up and your goals?

Travel is a growth catalyst. Over the past four years my photography has improved, I started learning Spanish, I’ve hand-written multiple travel journals, developed a website to catalog the destinations that I visit and even developed my own startup. I have made many friends and discovered aspects of my personality I didn’t know existed; I have improved the person that I am.

I believe a career should also be a growth catalyst; thus travel and work complement each other very nicely. My career will continue to follow a path towards growth. When that path ends then I will find a new path or clear my own.

10. How do you expect remote working to evolve in the future?

Technical limitations of remote collaboration have been largely eradicated; however, there remain management paradigms, guided by mistrust, fear and inability to effectively manage without physical control, which are strained when employees are beyond arms-length. 

Such paradigms will need to change to embrace an expanding workforce which is agile and productive outside those office cubicles they have been historically herded into. Are so many meetings required? Is the best work done by everyone between 8AM and 5PM? Can an office environment actually inhibit productivity? Do we enjoy commuting in traffic? These are questions many remote companies and employees have already answered for themselves – more will do so in the future.

11. Where can we follow you on?

I post photos and thoughts on the destinations I visit @ reidperyam.com. I’m also on instagram @reidperyam sans hashtags & selfies. Please connect on LinkedIn if anything written here resonates with you on a professional level. Also feel free to email me – my contact information is on my website.

Are you a remote worker too?
Would you like to share you story?
Just reach us at hrishikesh@remote.tools!

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