Exploring Retirement Destinations: Where Should Overstock.com Employees Consider Living Abroad?

Healthcare Provider Update: Healthcare Provider for Overstock.com Overstock.com provides its employees with health insurance options through major insurers offering Affordable Care Act (ACA) plans, including well-known providers like UnitedHealthcare and Anthem. Potential Healthcare Cost Increases in 2026 In 2026, employees at Overstock.com are expected to face significant increases in healthcare costs, driven by anticipated premium hikes in the ACA marketplace. Projections indicate that some states might see premium increases exceeding 60%, exacerbated by the potential expiration of enhanced federal premium subsidies. As many employees may bear a larger share of healthcare expenses, it is crucial for Overstock.com workers to stay informed about their benefits and explore strategies to manage rising costs. The combination of inflated medical expenses and changing employer strategies could lead to a challenging healthcare landscape, stressing the importance of proactive financial planning. Click here to learn more

Overstock.com employees who are planning to change their lifestyle and work abroad are advised to start planning early to ensure that their lifestyle and career fit the foreign country,' advises Paul Bergeron, a representative of The Retirement Group at Wealth Enhancement Group.

Tyson Mavar of The Retirement Group, a division of Wealth Enhancement Group, explains the legal and tax consequences of leaving the country for Overstock.com employees.

In this article we will discuss:

1. Trends and Motivations for Relocation: Examining the reasons behind it Overstock.com employees and other Americans are leaving the country for, including political climate and lifestyle issues.

2. Practical Aspects of Immigration: Exploring, Looking at different immigration paths and procedures to different countries like Canada, Mexico, and some countries in Europe and the differences between them.

3. Benefits and Challenges of Living Abroad: Exploring the financial and social implications of moving, the taxes, health care, and society, to help people who want to become expats make the right decision.

The idea of living abroad has always been attractive to many people, including the Overstock.com employees who are interested in the changed political systems, better health care, and affordable retirement options that lead to a better quality of life. Jean-Francois Harvey is a Miami-based attorney who notes that more than political reasons, more Americans are considering life abroad. Harvey's experience in immigration is particularly valuable for those who are planning to make some major changes.

Although political events such as Supreme Court hearings and presidential debates can lead to a revision of the quality of life one wishes to lead, the underlying motive is often a desire to live a better life. Harvey says, “The vast majority of people who are interested in changing the game in the United States require a Plan B as elections draw near.” It is not always necessary to have a country nearby as the choice of destination.

While Mexico and Canada are the favorite neighboring nations for the Overstock.com employees due to their proximity, some of them also have eyes on European countries like Spain and France due to the linguistic familiarity and easy visa procedures.

The process of moving is different and depends on the country. Using the Express Entry system, Canada has a process in place to quickly move skilled workers through a simplified process that could take as long as two years. This is because family ties in Canada can fast track this process. However, Mexico offers a retirement scheme that is suitable for those who want to spend their latter years in a tropical climate and must show proof of financial stability through their savings or regular income.

Mexico does not allow direct real estate purchases by foreigners but there are legal ways of making such acquisitions through existing entities. Europe presents a variety of immigration options, and laying claim to citizenship through parents or ancestry is still valid in many countries, including Portugal, Spain, France, and Italy. Also, the new digital nomad visas are a modern approach for professionals who want to live in Europe and continue working remotely abroad, not only benefiting the applicants but also their families.

Moving is a process that is accompanied by legal and tax consequences that occur when moving to another country and the treaties that prevent the double taxation of the same income when working there. This makes it easier to go back to the U.S. when needed. If you are a Overstock.com employee thinking about moving, you must consider the legal, administrative, and living conditions that accompany moving to another country.

Social infrastructure, healthcare, cost of living, and cultural considerations are important to think about in order to ensure that the move will help to meet personal and professional goals. In general, moving abroad is a complex process of assessing one’s lifestyle, career, and life situation. It is crucial to know the immigration laws and advantages of living in different countries. Although it is difficult to get permanent residency, it is worth it for financial and personal growth. A 2021 Expat Insider survey revealed that more than 80% of American expatriates 60 and older are better off financially since moving abroad.

Retirement is especially attractive in countries like Portugal and Mexico due to the low costs of living and the favorable tax treatments for retirees, which make the option of living abroad more appealing for people who want to stretch their retirement budget and quality of life. Leaving the United States for another country is like setting course on a ship. Just as a seasoned navigator picks a destination according to weather, cultural richness, and good ports, so should expatriates pick factors like quality of life and healthcare.

When you know how to avoid the pitfalls when it comes to immigration laws, then your transition to your new life abroad will be as smooth as sailing in calm waters.

Featured Video

Articles you may find interesting:

Sources:

1. Expat.com. 'Retirement Abroad: Trends and Top Destinations in 2025.' Expat.com, 2025. In this article, the role of retirees is seen as balancing lifestyle adjustments with financial needs through part-time work, consulting or business ownership while moving abroad, with the focus being on the semi-retirement lifestyle.

2. PlanWell Financial Planners. 'Expat Retiring Abroad? Rules on Taxes, Social Security, and Benefits.' PlanWell Financial Planners, 2024. The source outlines tax obligations, the Foreign Earned Income Exclusion (FEIE), and potential tax pitfalls of retiring abroad, which are crucial for retirees' financial planning.

3. van Sambeck, Becca. 'The Pros and Cons of Retiring Abroad.' Kiplinger, 22 Oct. 2023. According to Kiplinger, the advantages of retiring abroad include lower living costs and new cultural experiences; however, challenges such as cultural adaptation and complicated taxation affect U.S. retirees living abroad.

4. TrueNorth Wealth. 'Retiring Abroad: Pros, Cons, and Considerations.' TrueNorth Wealth, 2024. TrueNorth Wealth offers advice on financial, legal, and personal planning for retiring abroad, with a focus on how complex international tax laws, healthcare, and social environments affect retirees.

5. International Living. '2025's Best Countries to Retire.' International Living, 2025. In this article, the best retirement destinations are evaluated based on cost of living, healthcare, and overall quality of life, which can help retirees determine where they can best stretch their retirement dollars and enjoy a better standard of living.