Sears Holdings Employees: The Real Costs and Risks of Retiring Abroad

Healthcare Provider Update: Healthcare Provider for Sears Holdings Sears Holdings typically provides healthcare benefits to its employees through various insurance plans, often with national insurers such as Aetna, UnitedHealthcare, or Anthem Blue Cross Blue Shield being among the health carriers they have partnered with. The specific providers can vary by location and employee selection during open enrollment periods. Potential Healthcare Cost Increases in 2026 As we progress into 2026, the healthcare landscape is expected to face significant challenges, particularly for employees of Sears Holdings. Forecasts indicate steep premium hikes, with some states imposing increases of over 60%, largely influenced by rising medical costs and the potential expiration of enhanced ACA premium subsidies. The Kaiser Family Foundation highlights that without congressional intervention, millions of marketplace enrollees could see their out-of-pocket costs surge by more than 75%. This convergence of factors threatens to impose a substantial financial burden on both individuals and employers, necessitating proactive strategies to mitigate rising expenses. Click here to learn more

'Retiring overseas can be rewarding, but Sears Holdings employees must stress-test their income, health care access, and contingency plans against geopolitical and currency risks before making a decades-long commitment. Sears Holdings employees to approach this decision with disciplined planning and professional guidance to preserve flexibility and long-term stability.' – Paul Bergeron, a representative of The Retirement Group, a division of Wealth Enhancement.

'Retiring abroad may offer lifestyle appeal, but Sears Holdings employees should evaluate long-term income durability, health care access, and cross-border complexities before relocating. I believe Sears Holdings employees can benefit most from building flexible strategies that balance opportunity with prudent risk management.' – Tyson Mavar, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article, we will discuss:

1. The practical appeal of retiring abroad and why it may be tempting for high-earning professionals.

2. The core risks that can disrupt long-term retirement income and access to care.

3. The planning steps that can help you prepare for volatility while preserving flexibility.

by Neva Bradley, CFP®, Wealth Enhancement

For many people, retiring abroad can seem like a fantasy. Reduced living expenses. Views of the ocean. Warm temperatures. A life that moves more slowly. For many Sears Holdings employees who have built substantial retirement savings, the idea of enjoying those rewards overseas can feel well-earned after decades of dedicated service. The experience has long appealed to American retirees, particularly during extended periods of political and economic stability in their destination of choice.

However, conditions can shift quickly, even in places that have historically appeared steady. For Sears Holdings professionals over 55 who have accumulated $2 million or more, retiring abroad involves more than a lifestyle discussion—it calls for a thorough evaluation of potential risks.

There is never a lasting promise of stability.

Numerous locations that are favored by American seniors have long been considered hospitable. But conditions can change in any nation. Retirement planning should not only focus on positive scenarios, but also on low-probability, high-impact events that could potentially disrupt income, access to assets, or long-term stability.

The choice to retire is not made in five years. This approach spans several decades. Potential interruptions and evolving circumstances should be taken into consideration during planning, especially for Sears Holdings employees who may rely on a combination of pension benefits, 401(k) savings, and taxable investment accounts to fund their retirement.

Health Care Considerations in Foreign Countries

Even before leaving the United States, one of the largest risks in retirement is health care. There are restrictions on Original Medicare coverage outside of the U.S. Except in extremely rare and limited instances, it generally does not cover care received overseas. As a result, retirees who live abroad frequently arrange private international health insurance or other types of coverage to bridge the gap.

Returning to the United States for emergency medical treatment can be very expensive, particularly if evacuation is required. Depending on the location and physical condition, air ambulance evacuation can cost between $20,000 and $200,000, according to U.S. State Department guidance. ¹

For Sears Holdings retirees accustomed to robust employer-sponsored health care during their careers, understanding these limitations is critical before relocating abroad.

Retirement may last 25 to 30 years for individuals with longer life expectancy trends. According to the Social Security Administration, a 65-year-old today has a significant likelihood of living into their 80s, and many will live longer. ²

Access to treatment remains a major factor, even as medical needs and related expenses may rise over time.

Risks That May Be Outside Your Control

Retiring abroad can introduce additional uncertainties, such as:

- Currency fluctuations that affect income

- Foreign tax policy changes

- Limitations on property ownership

- Changes to residency or visa requirements

- Political unrest in the region

These are variables retirees do not influence directly.

Asking what to do if stability shifts is part of prudent retirement preparation. Sears Holdings employees who have worked globally may be familiar with geopolitical changes, but personal retirement exposure differs from corporate exposure.

Planning With Clear Perspective

This does not mean retiring overseas is inappropriate. To preserve flexibility, many individuals establish adaptable arrangements—spending part of the year abroad and part in the United States, maintaining liquidity reserves, and keeping strong U.S.-based financial relationships.

The objective is not to pass on opportunities. The objective is to prepare thoughtfully for volatility. Retirement should feel steady rather than uncertain.

It is important to stress-test your income strategy, review health care coverage options, maintain accessible cash reserves, and understand the tax implications that may apply across different countries if you are considering retiring abroad.

How The Retirement Group Assists Sears Holdings Employees

The Retirement Group works with Sears Holdings employees to help evaluate geopolitical, health care, and financial factors that may influence a long-term retirement strategy. Our team reviews pension options, 401(k) strategies, tax considerations, and global retirement exposures in a coordinated manner.

You can reach our team by calling (800) 900-5867 if you would like help building a retirement plan that accounts for both opportunity and risk.

Featured Video

Articles you may find interesting:

Sources:

1. U.S. Department of State, Bureau of Consular Affairs. “ Medicine and Health. ”  Travel.State.Gov , 11 Aug. 2025.

2. Social Security Administration. ' Actuarial Life Table ,' 2025 Trustees Report. 2025.

Other Resources: 

1. Centers for Medicare & Medicaid Services.  Medicare Coverage Outside the United States . CMS Product No. 11037, Dec. 2024,  www.medicare.gov/publications/11037-medicare-coverage-outside-the-united-states.pdf .

3. Social Security Administration.  Retirement Information for Medicare Beneficiaries . Publication No. 05-10529, Jan. 2026,  www.ssa.gov/pubs/EN-05-10529.pdf . 

4. Internal Revenue Service.  Tax Guide for U.S. Citizens and Resident Aliens Abroad . Publication 54, Jan. 2025,  www.irs.gov/pub/irs-pdf/p54.pdf .