Working Remotely From Colombia – A Perspective From A New Expat

In this guest post, Daniel Arthur shares his journey from office job to remote worker, which allows him to live his Unconventional Life in Colombia. Here is his story…

My remote work journey began long ago, several years into my career, and shortly after graduating from college. I’ve been working remotely for over twenty years, long before it became popular.

Back then, there were only three options for folks who wanted to work from home. They consisted of people who owned their businesses or were self-employed, freelancers, or W-2 wage-earning employees who worked for companies who valued their employee’s contributions to the company, invested in their success and career trajectory, and were sensitive to their employee’s overall quality of life.

I was very fortunate to convince my employer back in 2007 to agree to this arrangement. My experience could be a model for current and future expats wishing to work abroad.

This article consists of my experiences (and success) in approaching my employer with a solid business and action plan to grant my request to work remotely 100% of the time.

Establish Location Independence Before Moving Abroad

Medellin ParkI have worked remotely since 2007 in the U.S. and now in Medellín.

My professional career has lent itself to “remotability” while not tying me to a particular location, even in the finance and banking profession, where customer relationship management and interaction primarily represent 80% of one’s daily job function and duties.

I never liked going to the office and only did it for the first ten years of my career. I dreaded the Southern California commuter freeway and traffic, the stress associated with getting out of bed three hours before my start time, rushing out the door, the office politics, the “cliques” that were in the office, having my boss or others standing over my shoulder while I worked, etc.

Over a long holiday weekend back at the end of 2006 as I sat on the sofa watching TV – dreading going to work the following Tuesday. I knew I had to begin developing a plan to present to my leadership that would allow me to work from home 100% of the time.

Establishing location independence as early as possible in your tenure with a company is the key for many expats desiring to work remotely abroad.

Furthermore, domestic stateside employees can benefit too from approaching their employer and manager about flexible work arrangements as soon as the right opportunity presents itself (no later than a year into your employment with the company –I waited for nine to do so –but I believe more employers are open to at least entertaining a conversation now about the topic of remote work).

Find or Have Your Employer Support Before You Move

Remote work in a cafeEngaging your employer in an initial discussion before committing to expat life is critical.

If you intend to keep your current job and be successful, you want their support and agreement, and this might involve a difficult discussion with your direct manager, who may or may not be willing to work with you.

Working for finance banking remotely was virtually unheard of, and management’s primary concern was it involved adverse risk to the company, especially in handling and potential exposure of customer information that I had access to.

It took me over a year of planning and creating a proposal with my manager and over nine months later for risk management, legal, and human resources to convince my company to approve my remote work arrangements.

I worked with my manager in drafting my proposal because involving them, in the beginning, was critically important. You want your manager to be your ally and advocate because they will directly evaluate your work and performance off-site.

Suppose you don’t believe your manager will support your desire for permanent remote work arrangements and location independence. In that case, you should strengthen your relationship with your manager and leadership team before moving abroad.

Engage The Assistance of A Legal and Tax Professional

TaxesBefore moving to Medellín late last year, I engaged a competent immigration attorney and tax professional.

While not required, hiring dual-licensed professionals in both your home country and your intended destination country is highly encouraged.

I lived in Florida before moving to Colombia, so running a Google search for local professionals in my area was a relatively simple process.

I shared my long-term goals and plans with the professionals I hired and sought their advice on remote work, nomad life, and the appropriate legal and tax strategies I needed to have in place before boarding the plane.

While my situation was pretty straightforward (being married to a Colombian national), both professionals recommended that I maintain tax residency in the U.S.

My tax advisor, in particular, noted that both countries tax worldwide income, both countries require personal income tax returns filings with the IRS and DIAN, and both allow deductions for foreign income earned abroad; I would still maintain my eligibility to collect Social Security upon retirement in the U.S.

Plan For The Unexpected To Happen At Any Time With Your Remote Job

I don’t have the same remote job as when I moved to Medellín last year. This past April, I became the latest victim of corporate downsizing and was told over a Zoom call that my job was now redundant.

I had anticipated this scenario could happen several years before I decided to move abroad. Given in the last year that many companies were downsizing, this became even more relevant. Despite the current state of the economy, I was confident I had built up my skills and abilities over the years into new possibilities.

The next day after that Zoom call, I immediately began seeking freelance opportunities by contacting my network and offering my service. I pitched several consulting gigs and received two offers, which I immediately accepted.

Years prior, I had implemented a solid savings and investments strategy that was firmly in place. I turned to other ideas to generate income should I ever become unemployed at any point in my career (i.e., backup plan, savings, investments, passive income streams, etc.).

Final Thoughts

I’m blessed beyond measure to be able to work remotely for over ten years. At age 47, I’m proud of my professional accomplishments, and a large part of my success is directly related to the opportunity and confidence of my leader to work remotely many moons ago.

Despite being laid off within a short time of moving abroad, I’m confident that the time I invested in the above long-term strategies has helped me tremendously.

I would encourage anyone who has ever dreamed of moving abroad to forge ahead and turn their dream into a reality. With the proper support in place, anything is possible.

You can read about my transition from Orlando to Medellín, living abroad for the first time, and find out more about me by visiting my Medium page by clicking here.

I’m Daniel, an “unconventional” living in Medellín, Colombia, with my Colombian partner. I was born and raised in Southern California. I have a Bachelor of Arts from California State University, Long Beach (1995) and a Master of Science in Higher Education from the University of Miami (2000). I am a former “corporate worker” with 25+ years of experience in finance, banking, wealth planning, and tax.

2 replies
  1. Paul Snyder
    Paul Snyder says:

    This was a good read. Thanks!
    Do you feel that being released was to any degree influenced by you going offshore?

    • Daniel Arthur
      Daniel Arthur says:

      Hi Paul, thanks for the comment! My former employer has been doing several layoffs in the last two years (beginning in January 2021). They seemed focused on cutting “all remote employees across the U.S.” The problem with them is that they overhired during the pandemic, and when business slowed down, they needed to be more staffed. The company is a global company with offices on four continents, so moving abroad did not affect their decision. Interestingly enough, if you look at their career openings today, remote jobs have yet to be posted. It makes one wonder, though!


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