Summary

The author shares their experience of navigating the challenges of finding a fully remote job that allows for travel, despite having less-than-optimal starting conditions and no internal contacts.

Abstract

In 2021, the author decided to quit their job at an intergovernmental organization to pursue a fully remote job that would allow them to travel the world. However, they faced several challenges in securing such a position. The first challenge was finding real remote work, as many job advertisements that claim to be fully remote often have restrictions on working from other countries. To navigate this, the author suggests dissecting job ads, paying special attention to the final paragraphs, and searching for the company online to review their remote work policy.

The second challenge was facing the competition, as very few companies worldwide have a remote work policy that permits employees to spend extended periods abroad. The author suggests bookmarking the career pages of companies with remote work policies that interest you and reviewing them periodically. They also recommend preparing a tailored CV and cover letter, highlighting independence and autonomy.

The third challenge was not having enough skills or work history. The author suggests leveraging the experience you have gained and being open to starting with a less exciting role initially. They also recommend extracting every bit of value from your experiences for your CV, cover letter, and interviews.

Bullet points

The author quit their job to pursue a fully remote job that would allow them to travel the world.
The first challenge was finding real remote work, as many job ads have restrictions on working from other countries.
To navigate this, the author suggests dissecting job ads, paying special attention to the final paragraphs, and searching for the company online to review their remote work policy.
The second challenge was facing the competition, as very few companies worldwide have a remote work policy that permits employees to spend extended periods abroad.
The author suggests bookmarking the career pages of companies with remote work policies that interest you and reviewing them periodically.
They also recommend preparing a tailored CV and cover letter, highlighting independence and autonomy.
The third challenge was not having enough skills or work history.
The author suggests leveraging the experience you have gained and being open to starting with a less exciting role initially.
They also recommend extracting every bit of value from your experiences for your CV, cover letter, and interviews.

How I Navigated The Three Major Challenges Of Landing A Fully Remote Job And Travel The World

Without Internal Contacts And Less-Than-Optimal Starting Conditions

In 2021, I took a leap of faith and decided to quit my position at a highly regarded intergovernmental organization to pursue my dream of finding a fully-remote job that would allow me to travel the world while enjoying the security of a steady salary.

However, my starting conditions were less-than-optimal. You can read about it in Part 1 of this series:

This Is How I Transitioned From Being an Office-Based To a Fully Remote Employee Traveling the…

Without Being a Software Engineer, Data Scientist Or Having Any Particular Hard Skill

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The following is Part 2, where I share an in-depth account of the challenges I faced in securing a fully remote position and how I navigated them.

If you find yourself at a similar crossroads in life, I hope that my experience can provide you with a realistic perspective on this endeavor — and why I still believe it’s one of the best decisions I’ve ever made.

Here’s a list of the challenges I encountered and how I dealt with them:

Struggle 1 — The Challenges of Finding (Real) Remote Work

When embarking on their first remote job search, most people, including myself at the time, may believe that when they come across a fully remote job advertisement, it automatically means they can work from anywhere in the world.

It can be disheartening to discover that even when job ads state “This is a fully remote position”, “Work From Home” or “Work from home (or wherever),” they usually mean you can work remotely… from your country of residence.

In fact, remote jobs are already a minority in the job market, and those that allow you to work from and travel to other countries are even rarer.

How to Deal With It?

To navigate this, you need to dissect the job ads you encounter.

Pay special attention to the final paragraphs of the advertisement where they discuss benefits, such as 401K, as this might be an indicator that they primarily hire in the US and prefer their workforce to remain in the country.

Also, search for the company online and thoroughly review their Careers page, which should clarify their remote work policy and whether they offer benefits allowing employees to work from abroad for a specified period.

If neither of these sources provides clarity, consider reaching out to a recruiter before applying to inquire about their remote work policies.

Struggle 2— Facing the Competition

Struggle number 1 will have already exposed you to the harsh reality that very few companies worldwide have a remote work policy that permits employees to spend extended periods abroad.

This is because enabling employees to work from abroad might give rise to several issues for a company, including including taxation, permanent establishment, and social security matters, which most companies are not willing to dedicate energy to investigate.

However, there are companies that have systems in place (or dedicated departments) to deal with such bureaucratic challenges and allow remote work from abroad for certain periods.

Most likely, you’ll need to come to terms with the fact that there are likely hundreds of other applicants vying for the same position, but be persistent and don’t let this discourage you in the pursuit of your dream — like me, you might be the one selected for the role.

How to Deal With It?

After carrying out the suggestions to navigate Struggle 1, bookmark the career pages of all the companies whose remote work policies interest you and review them periodically (set a reminder on your phone if needed).
If during your search, you run into companies that don’t allow unrestricted global travel but do permit travel within specific regions, such as EMEA, APAC, or LATAM, perhaps due to the presence of their headquarters in those regions and you are comfortable with such traveling policy, consider pursuing such opportunities. It can save you some headaches.
Finally, make sure to prepare a tailored CV and tailored cover letter. There are no shortcuts here, unless you have contacts within the company that you can leverage. For the rest of us, meticulously crafting these documents is the only way to rise through the ranks of potential candidates. Be sure to highlight your independence and autonomy, as when working fully remote, it’s essential to be self-regulating without constant supervision from a boss.

Struggle 3 — I Don’t Have Enough Skills or Work History

I feel you. When I took the leap, I lacked an extensive work history and didn’t have clear or highly competitive “hard skills.”

How to Deal With It?

Even if I didn’t have a long work history and I felt insecure about it, I did have some work experience, including roughly one year after my graduation and several internships during my studies.

In fact, unless I wanted to take years to progressively build my dream role until I could find a fully remote version of it, my only choice was to leverage the experience I had gained up until that moment and start from there.

My desire to travel and work remotely couldn’t wait any longer.

If you are in a similar situation, you should know that:

A crucial element in the pursuit of remote work, especially if you lack substantial expertise, is being open to starting with a less exciting role initially. Securing your dream role right from the start while also pursuing a dream lifestyle is nearly impossible. Be willing to get your foot in the door and, over time, refine your position within the company or explore other remote opportunities.

For this reason, the steps I took were the following:

I made sure to extract every bit of value from my experiences for my CV, cover letter, and interviews. I spent hours thinking about how to best present the knowledge I had and filled in any knowledge gaps by educating myself through online courses and articles.
I applied for remote roles that had something in common with my previous experiences even if they didn’t sound incredibly exciting. My plan was to achieve a fully remote lifestyle first, and refine my job position after that.

Conclusions

Landing a fully remote job that allows you to travel the world for an extended period of time is not a pursuit for the faint of heart. This is mainly due to its non-mainstream nature and the high level of competition.

When, you can’t rely on a lengthy work history, personal contacts, or a highly competitive skillset, achieving this goal can feel daunting and unattainable. I know it because I’ve been there.

Nevertheless, despite these obstacles, I stand as living proof that securing a fully remote job that allows for extended travel is an achievable endeavor.

It certainly requires significant perseverance and discipline, but the effort becomes exceedingly worthwhile when you finally secure such a position and find yourself traveling across different continents while enjoying the security of a steady employee salary.

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PS: Before you leave this page, if working and traveling full-time is what you’re dreaming of, then join my newsletter Freedom Focus. Twice a month, you will receive insights on how I managed to travel and work full-time for the past two years, reflection prompts, and actionable items to start doing the same. Join here.