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Working remotely in 15 countries over 7 years while helping high performers land remote jobs

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Jordan Carroll

Co-Founder and Director of Creative - Unlocked Authority

Published on Tue Aug 27 2024

Introduction 

Hey, can you please introduce yourself?

I’m Jordan Carroll, aka The Remote Job Coach & I’ve worked remotely, consistently,
upwards of 7 years, for:
↳ A global Fortune 50 tech company with over 400k employees (IBM)
↳ A fully distributed, remote-first travel company with 150 employees (Remote Year)
↳ Multiple other startups with a range of 2-50 employees as well as my own businesses

I’ve lived in 15 countries on 5 continents in the past 3 years and am a member of the Forbes Coaches Council. I create content, courses, and coaching programs to help high performers learn a process to land legitimate remote jobs and gain freedom and flexibility in their lives. Thousands of remote job seekers have used my methodologies to find success in their search. I write blogs and create videos on YouTube about the nomadic lifestyle and remote work. I’m also currently working on my book, “Remote For Life: How to Find a Flexible Job and Fast Forward to Freedom” (Launch early 2022), and a coworking subscription service called CoWorkClub.io.


Motivation for Remote Work 

What motivated you to choose remote working?

A snow day! I was working at a Fortune 50 company in 2013 and commuted 1.5 hrs each way living in Boston, MA. During the winter we got hit with a ton of snow and I woke up one day to an email that seemed like a message from God… “today you can work from home.” At the time it was really just a buffer for my hangover and I slept in until about 5 minutes before my meetings… I ended up negotiating work to be remote one day a week after the snow season, and then ultimately worked fully remote for that company. Over the course of years of working remotely, I realized it wasn’t just a helpful buffer for more sleep, it was actually my biggest opportunity for self-growth and actualization. I used the time I got back to go to the gym, make my own food, read, and try new hobbies. It was a blessing.

Initial Months and Expectations

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

I found my first remote job on Craigslist as a telemarketer in 2013 while I was still in university. Being a remote telemarketer in 2013 was about as glorious as it seems. I would squeeze in hour-long “call-blitzes” in between a full-time university course load &two other part-time jobs. Little did I know, that the remote work movement would become the most impactful cultural phenomenon in my life moving forward. For my first corporate job at IBM, I negotiated my work to be remote one day a week after the snow in Boston also gave me some WFH days. I didn’t really know what to expect and back then it wasn’t as big of a thing as it is now. I mostly just used it to sleep in later 😂 Then at some point I started using it to accelerate my own personal growth.

Time flies! That day marked 3 years of my journey living #alcoholfree

Finding Remote Work Roles 

How did you find remote working roles?

My network! That’s why I teach people how to do this: Many people are just applying to remote job boards online and making awful first impressions. I noticed I was inherently using a strategy to become close in proximity to decision-makers at remote organizations and opportunities, and that was giving me options. After getting a lot of questions about ‘how’ I was able to work remotely and travel the world, I started teaching my methods.

These pics from a month before my operation serve as a reminder of how quickly things can change, and how important it is to have people around me who care.⁣


The Good, Bad and Ugly of Remote Work 

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

Best:
It feels like we live in a world that’s limiting our choices. 2020 left people jobless, governments shut down entire cities and countries, and economies came crashing down. One movement stands as a unique symbol of choice:

In January 2020, before I could’ve known what was about to happen, I permanently moved to Mexico. After living in 15 countries since early 2018, living here is more normal to me than in the US (where I’m from). And after 7 years of working remotely, I’ve fully realized its potential as far more than “working away from an office.” It’s afforded me amazing privileges and given me the choice to build work around my lifestyle goals. It's the movement of choice.
Good:
I genuinely feel like remote work saved my life. It was the greatest vehicle for my self-development. Remote work fundamentally changed what was possible for me:
↳ Lifestyle
It allowed me to build work around a life of travel, inhabiting 15 different countries in 3 years, ultimately moving to Mexico. It gave me time to pursue hobbies like video production, Spanish, & stand-up comedy.

↳ Health
It gave me the flexibility to prioritize health. I lost 40 lbs & 15% BF in 90 days, quit cigarettes, drugs, and alcohol, and started competing in Spartan Races, Tough Mudders, & international marathons.

↳ Relationships
It gave me the freedom to meet hundreds of connections on LinkedIn IRL & join communities: Nomad Cruise, Remote Year, Running Remote, Nomads Giving Back, Remote Tools & more.

These pics from a month before my operation serve as a reminder of how quickly things can change, and how important it is to have people around me who care.⁣

Worst:

I awoke one winter morning almost 7 years ago to an email that felt like a message sent from God. I wiped the crust out of my eyes, read it slowly, and then did a double-take:
“Snowed in. Work from home today.”


I reset my alarm, rolled over, and quietly rejoiced. It certainly beat bundling up in 4layers, trudging downstairs, and unenthusiastically scraping ice off my windshield before a 1.5-hour commute (remember that @Liz and @Andrew)? Boston winter was the coldest and snowiest it had been in a decade, and many work-from-home days followed.
However, at the time I didn’t realize that working remotely could also be the “noose that me.”
Sometimes I’d sleep in longer, waking up just before calls, even choosing Netflix instead of emails. My natural reaction was to choose less resistant activities, ultimately becoming a lower version of myself.
I’m not proud of it. But it taught me:

You don’t just flip a switch, and all of a sudden work from home productively if you haven’t before. There’s a learning curve.

5 MISTAKES I MADE:
1. Not Creating a Schedule
2. Not Optimizing My Environment
3. Under-Communicating
4. Too Many Distractions
5. Not Being Honest With Myself

(Bonus): Not Investing In My Growth

No matter the stresses or emotions or extra bullshit I’m carrying from my day, once we check Ball it’s all gone from my head.

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

I once won a dance contest I didn’t realize I was being entered into on a random cruise in Santa Marta, Colombia. I didn’t speak Spanish at the time so when they volunteered me I stood up and walked over not knowing what was happening. Then the emcee with the microphone was standing next to 3 other guys and asking them questions in Spanish and Creole and having them introduce themselves. I had no idea what he was saying, so when he got to me and asked me questions I just said “Mi nombre es Jordan” and “si,” to some other random question and the 100+ people watching erupted in laughter (still not sure what he said). We had the dance and I ended up winning (the bar was low). I received a returned reggaeton CD, a bandana, and two coupons for scuba diving 😂.

Remote Work Tech Stack 

What tools do you swear by while working remotely?

Find my list on my site here: https://theremotejobcoach.com/apps-and-subs

And some of them written out:

  • Slack
  • Zoom
  • Google Suite (Drive, Docs, Sheets etc)
  • LastPass
  • Loom
  • Evernote
  • Things
  • Bitly
  • Kartra


Advice for Remote Workers

What is your golden advice to a new remote worker?

Don’t skimp on investing in your environment to help you be successful! Here’s what I tell people who are ‘aspiring’ remote workers, which somewhat overlaps: Don’t wait to work remotely until you’re working remotely.⁣

There’s something about bali that brings out the inner basic in anyone that goes…whether a new crippling addiction to acai bowls, accidentally eating vegan every meal, or even taking pre-meditated sunset pictures

Huh?⁣

If you have a goal of working remotely for a company, do everything you can to prepare yourself to become a remote, capable worker before you’re ever hired.

Don’t wait to invest in the proper equipment once you’re hired… it’s the preparation before you get the job that has a huge influence on whether or not you get the job.⁣

And if you’re budget-conscious, it doesn’t mean it has to be expensive. ⁣

Go for quality and value, not just the most expensive things you can find.⁣

Here’s why…⁣

Imagine you finally land an interview with your dream remote company.⁣

Your interview with them is a PREVIEW of what it’s like to work with you.⁣

⛔️ Now imagine the perception you give off if your webcam looks like you’re filming out of a potato, your audio sounds like you’re underwater, the lighting in the room makes you look like a silhouette, and you’re holding your computer in your lap so the camera is looking straight up your nose.⁣

✅ Change the perception. What if you’re sitting there in a comfortable chair and desk with great lighting and the camera looks straight at your face at eye level, you’ve got clear and crisp audio and a natural swagger that comes with being confident in your system.⁣

In order to be what you want to be, you have to be that person before you’re “ready.”Start now, and watch not only the way others react to you differently but observe how great you feel with the right equipment.⁣

Looking Ahead

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

I see myself as a leading voice in the remote work community and the #1, premier voice for remote job seekers. I believe I’m already there, but there are so many fun projects I am working on. I’m writing a book that will be widely available in early 2022 (forwardwritten by Darren Murph and blurbs from Goncalo Hall, Tarek Kholoussey, Madeline Mann, and Olumide Gbenro — all superstars!) and I’m working on a coworking club subscription service to help bring virtual coworking to the masses. Goals tend to shift so my main focus is just listening to my intention and being open to what the universe brings. Working on the things that light me up in the meantime is the best way to live!


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

A borderless society, companies removing hiring restrictions, countries welcoming remote workers, governments adapting to technology, and remote first as the default. So many great things have come from the acceleration of remote work. I’m excited for a place where there is a country on the internet (like what Plumia.Country) is trying to accomplish, and where people all over the world can work online and have access.


Where can we follow you?

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