Why More Guess Employees Are Considering Social Security Early — And How Medicare Changes Play a Role
Healthcare Provider Update: Healthcare Provider for Guess
Guess, the renowned apparel and accessories brand, typically partners with national health insurance providers like UnitedHealthcare for employee healthcare coverage. Such partnerships enable them to offer comprehensive health plans to their employees, ensuring access to a wide network of healthcare services.
Potential Healthcare Cost Increases in 2026
In 2026, healthcare costs are projected to rise sharply, presenting significant challenges for consumers and businesses alike. Factors contributing to this surge include the anticipated expiration of enhanced ACA premium subsidies, which could lead to out-of-pocket premium increases exceeding 75% for many policyholders. Additionally, ongoing inflation in the medical sector, driven by escalating costs in hospital services, labor shortages, and increased drug prices, further complicates the financial landscape. As healthcare providers and insurers navigate these pressures, consumers may find themselves facing unprecedented cost burdens unless proactive measures are taken to mitigate the impact.
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'Guess employees weighing when to file for Social Security should consider both current health care costs and long-term income needs, so they can stay adaptable as retirement unfolds.' — Paul Bergeron, a representative of The Retirement Group, a division of Wealth Enhancement.
'Guess employees can benefit from thoughtfully coordinating Social Security timing with health care expenses so their retirement income stays aligned with their evolving needs over time.' — Tyson Mavar, a representative of The Retirement Group, a division of Wealth Enhancement.
In this article, we will discuss:
How Social Security filing age affects retirement income.
How Medicare expenses factor into when retirees claim benefits.
Why emotional concerns are shifting filing behavior for many Americans.
Written by Wealth Enhancement advisors Kevin Landis, CPA and Wesley Boudreaux
Advisors in the retirement-income space have long suggested that retirees consider delaying filing for Social Security benefits. For those with a full retirement age (FRA) of 67, waiting until age 70 can result in monthly payments that are around 24% higher.
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And for those with an FRA of 66, the increase if one waits until age 70 is closer to 32%.
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Guess employees nearing retirement often hear this same message.
However, new national data indicates a growing number of Americans plan to claim Social Security before age 70. Cost pressures and health care related issues are major influences in this trend.
The Retirees’ Reality
Today’s retirees face a very different environment than those in past decades, including less access to traditional pensions, rising health care costs, and mounting everyday living expenses. In the private sector, only about 15% of workers still have access to defined benefit pensions,
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affecting many households and Guess employees.
According to retirement consultant Wesley Boudreaux, 'most retirees are not choosing to claim early for the sake of it.” Instead, rising medical and living costs are driving earlier benefit decisions because of cash flow pressures.
One major factor? Health care. Nearly 39% of out-of-pocket health care spending by Medicare beneficiaries was equivalent to Social Security payments received, on average, in 2022.
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Medicare Advantage: A Key Planning Factor
Additionally, shifts in Medicare Advantage plans have left many retirees unsure about upcoming costs. Benefit structures can vary significantly by year or by region, causing cost surprises that Guess workers and their families may need to plan for.
“We are already seeing clients paying more for health care than expected,” said Kevin Landis, CPA. “When medical expenses rise, Social Security often becomes the first lever people pull to handle that burden.”
This is why coordinating Social Security filing decisions with Medicare coverage choices remains important, particularly when plans change annually.
“This is the intersection of Social Security and health care planning,” Landis adds. “Changes in one can influence the other.”
Emotional Considerations Also Matter
Money matters aren’t the only reason retirees claim earlier. Concerns about the future of Social Security have caused many to look for the emotional comfort of taking benefits sooner, including some Guess workers preparing for retirement.
While benefits are expected to continue—even if trust fund reserves decline in the 2030s—worries about future payouts can play a role.
“It’s not just about math,” Boudreaux explains. “People want control and stability in retirement, even if that means receiving less over time.”
Finding the Right Approach for You
Whether filing early is a good fit depends a lot on health, cash flow needs, and longer-term retirement goals. Thoughtful planning helps maintain flexibility, rather than driving you to respond under pressure.
“The best approach balances today’s needs with what lies ahead,” Landis says. “And that begins with understanding how Medicare and Social Security interact.”
Need Help Reviewing Your Options?
The Retirement Group, a division of Wealth Enhancement, helps individuals evaluate Medicare electives, analyze Social Security filing alternatives, and design retirement income strategies based on personal goals—including guidance tailored to those employed by Guess.
📞 Call (800) 900-5867 before your next enrollment period to schedule a Social Security & Health Care Review.
Work toward confidence in your long-term retirement income decisions.
About the Authors
Wesley Boudreaux and Kevin Landis, CPA, provide retirement income and tax planning guidance through Wealth Enhancement, helping people make informed choices about Social Security, Medicare, and financial well-being.
1. Social Security Administration.
When to Start Receiving Retirement Benefits: Publication No. 05-10147
. May 2024. U.S. Government Publishing Office, Washington D.C.
2. Topoleski, John J., Elizabeth A. Myers, and Sylvia L. Bryan.
Worker Participation in Employer-Sponsored Pensions: Data in Brief and Recent Trends (R43439)
. Congressional Research Service, 18 Sept. 2024.
3. Medicare Payment Advisory Commission.
Report to the Congress: Medicare Payment Policy – Chapter 11: The Medicare Advantage Program: Status Report
. Mar. 2025, medpac.gov/wp-content/uploads/2025/03/Mar25_Ch11_MedPAC_Report_To_Congress_SEC.pdf.
4. Board of Trustees, Social Security.
2025 Annual Report of the Board of Trustees of the Federal Old-Age and Survivors Insurance and Federal Disability Insurance Trust Funds
. 30 June 2025. U.S. Government Publishing Office, Washington D.C.
What type of retirement savings plan does Guess offer to its employees?
Guess offers a 401(k) retirement savings plan to help employees save for their future.
Does Guess match employee contributions to the 401(k) plan?
Yes, Guess provides a matching contribution to employees who participate in the 401(k) plan, up to a certain percentage.
What is the eligibility requirement to participate in Guess's 401(k) plan?
Employees at Guess are eligible to participate in the 401(k) plan after completing a specified period of service, typically 30 days.
Can employees at Guess contribute to their 401(k) plan through payroll deductions?
Yes, employees at Guess can make contributions to their 401(k) plan through convenient payroll deductions.
What is the maximum contribution limit for the Guess 401(k) plan?
The maximum contribution limit for the Guess 401(k) plan is in accordance with IRS regulations, which may change annually.
Does Guess allow employees to take loans from their 401(k) accounts?
Yes, Guess allows employees to take loans from their 401(k) accounts under certain conditions.
What investment options are available in the Guess 401(k) plan?
The Guess 401(k) plan offers a variety of investment options, including mutual funds, stocks, and bonds.
How can employees at Guess access their 401(k) account information?
Employees at Guess can access their 401(k) account information through the plan's online portal or by contacting the plan administrator.
Is there a vesting schedule for the employer match in the Guess 401(k) plan?
Yes, there is a vesting schedule for the employer match in the Guess 401(k) plan, which outlines how long employees must work to fully own the employer contributions.
Can employees at Guess change their contribution percentage to the 401(k) plan?
Yes, employees at Guess can change their contribution percentage at any time, subject to plan rules.
With the current political climate we are in it is important to keep up with current news and remain knowledgeable about your benefits.
For Guess, Inc., the company's 401(k) plan is known as the "Guess, Inc. 401(k) Plan and Trust." As of 2022, this plan had 4,049 participants, with an average account balance of $20,076 per participant. The estimated average employee contribution in 2022 was $1,269. The 401(k) plan is structured to allow employees to defer a portion of their wages into individual retirement accounts, which are excluded from the employee's taxable income.
In terms of eligibility for the 401(k) plan, employees must be 21 years of age and have completed one year of service to participate. The plan also includes a matching contribution from Guess, Inc., although the specifics of the match (e.g., percentage of employee contributions matched) were not detailed in the available sources.
Regarding the pension plan, Guess, Inc. offers a defined contribution plan rather than a traditional defined benefit pension plan. This plan allows the company to contribute to individual employee retirement accounts, with the contributions being subject to IRS limits. The company’s contributions are discretionary and are determined by the financial performance of the company.
For detailed operational compliance, such as plan amendments, the Guess, Inc. plan is governed by the SECURE 2.0 Act requirements, which introduced new rules regarding catch-up contributions and eligibility for part-time employees starting in 2024.
Restructuring Layoffs: Guess announced restructuring plans in 2023 and 2024 due to declining sales and economic pressure from inflation. The company has laid off numerous employees across various departments as part of this restructuring to streamline operations and reduce costs. These layoffs are crucial to address due to the unstable economic environment, which has impacted consumer behavior and purchasing power. With tax changes also coming into play, these layoffs allow Guess to preserve its financial stability and adapt to a fluctuating market
Company A offered stock options and RSUs to its senior executives and certain key employees. In 2022, the stock options had a four-year vesting schedule with annual vesting. The RSUs granted in 2023 were subject to performance-based criteria. (Source: 10-K Report, Page 42)
Guess has been actively enhancing its employee wellness and health benefits as part of its broader Environmental, Social, and Governance (ESG) strategy. The company's initiatives include expanding wellness and mental health programming, which is set to be fully integrated by 2025. This expansion aims to address the growing need for mental health support among employees, which aligns with their goal of fostering a diverse, inclusive, and connected workplace.
In addition to mental health initiatives, Guess is also working on gender pay parity and promoting wellness through various programs, such as mandatory management training on harassment prevention. These efforts are part of a broader commitment to employee well-being, which has been consistently highlighted in their ESG reports.
Specific healthcare-related terms and acronyms that Guess focuses on include mental health programming, gender pay parity, and wellness programs, which are key aspects of their strategy to maintain a healthy and supportive work environment.
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