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NerdWallet's Smart Money Podcast
NerdWallet's Smart Money Podcast•November 3, 2025

Healthcare Open Enrollment Tips for 2026 and a Catch-Up Plan for Retirement

A comprehensive guide to navigating healthcare open enrollment for 2026, covering health plan selection strategies, retirement planning tips for Gen X, and key considerations for choosing the right insurance coverage based on individual health needs and financial situations.
Career Transitions
Frugal Living & FIRE Movement
Burnout & Work-Life Balance
Habit Building
Remote Work
Sean Piles
Elizabeth Aiola
Kate Ashford

Summary Sections

  • Podcast Summary
  • Speakers
  • Key Takeaways
  • Statistics & Facts
  • Compelling StoriesPremium
  • Thought-Provoking QuotesPremium
  • Strategies & FrameworksPremium
  • Similar StrategiesPlus
  • Additional ContextPremium
  • Key Takeaways TablePlus
  • Critical AnalysisPlus
  • Books & Articles MentionedPlus
  • Products, Tools & Software MentionedPlus
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Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.

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Podcast Summary

This Smart Money podcast episode kicks off a two-part series on navigating open enrollment season. The first half features a book club discussion with authors Kerry Hannon and Janna Herron about "Retirement Bites: A Gen X Guide to Securing Your Financial Future," exploring how Generation X can overcome their retirement savings challenges. (02:30) The second half dives into healthcare plan selection during open enrollment, with NerdWallet writer Kate Ashford explaining the differences between premiums, deductibles, HMOs, PPOs, and high-deductible health plans (HDHPs).

  • Main theme: Empowering listeners to make informed financial decisions during open enrollment season while addressing Gen X's unique retirement planning challenges through practical strategies and healthcare optimization.

Speakers

Kerry Hannon

Kerry Hannon is a co-author of "Retirement Bites: A Gen X Guide to Securing Your Financial Future" and an expert on retirement planning and career transitions. She brings extensive experience helping professionals navigate late-stage career planning and retirement security challenges.

Janna Herron

Janna Herron is a co-author of "Retirement Bites: A Gen X Guide to Securing Your Financial Future" and specializes in personal finance and retirement planning. She provides research-backed insights into the unique financial obstacles facing Generation X.

Kate Ashford

Kate Ashford is a NerdWallet writer who specializes in health insurance and employee benefits. She has extensive experience writing about health insurance complexities and helps consumers navigate open enrollment decisions with practical, accessible advice.

Key Takeaways

Don't Panic About Late-Stage Retirement Planning

Gen X faces unique retirement challenges, with the typical household having only $40,000 in retirement savings. (02:30) However, the key is to avoid panic and take systematic action. Authors Kerry Hannon and Janna Herron emphasize that it's never too late to take control of your financial future. The first step involves conducting a thorough financial inventory - understanding your cash flow, identifying where money is going, and recognizing areas of lifestyle creep that may have occurred as income increased. This foundational assessment allows you to redirect resources toward retirement savings and debt reduction.

Tackle High-Interest Debt as Your Top Priority

Debt elimination emerges as the most critical obstacle to overcome for financial security. (14:03) As Hannon states, "debt is a dream killer" and represents the biggest barrier to future financial security. High-interest credit card debt and student loans significantly impact Gen X's ability to save for retirement. The speakers recommend getting serious about debt reduction strategies, whether through consolidation, aggressive payment plans, or lifestyle adjustments. Becoming debt-free creates breathing room in your budget and allows you to redirect those payments toward retirement savings and other financial goals.

Consider Extended Working Years as a Strategic Choice

Rather than viewing extended working years as a failure, reframe it as a strategic financial decision. (11:11) Hannon suggests that stretching out working years can significantly improve financial security, especially with remote work opportunities creating more flexible arrangements. This doesn't mean grinding at a stressful job forever, but rather finding ways to use your skills in consulting, part-time roles, or passion projects that generate income. The key is finding work that makes a difference while providing financial support during the transition to full retirement.

Match Your Health Plan to Your Healthcare Usage Patterns

When selecting health insurance during open enrollment, your decision should be based on realistic assessment of your healthcare needs. (22:45) Kate Ashford explains that you need to become a "healthcare fortune teller" by analyzing your typical medical usage. If you have chronic conditions, are pregnant, or frequently see doctors, higher premium plans with lower copays and deductibles make sense. However, if you're generally healthy and only need annual checkups and occasional care, high-deductible health plans (HDHPs) with lower premiums can be more cost-effective, especially when paired with Health Savings Accounts (HSAs).

Leverage HSAs as a Triple Tax-Advantaged Investment Vehicle

Health Savings Accounts offer an unmatched triple tax advantage that makes them powerful wealth-building tools. (28:15) Money goes in pre-tax, grows tax-free through investments, and comes out tax-free when used for medical expenses. Unlike Flexible Spending Accounts (FSAs) which are "use it or lose it," HSAs roll over year to year and can function as additional retirement accounts. This is particularly valuable since healthcare costs in retirement are substantial and predictable, making HSAs an ideal vehicle for both current medical expenses and long-term retirement healthcare planning.

Statistics & Facts

  1. The typical Gen X household has just $40,000 in retirement savings, despite the oldest members of this generation turning 60. (02:22) This statistic was cited by the book authors to illustrate how unprepared this generation is for retirement compared to their needs.
  2. About four million people are projected to lose their health coverage and become uninsured if enhanced ACA subsidies expire, according to the Congressional Budget Office. (31:04) This represents a significant impact on healthcare accessibility for marketplace participants.
  3. Health care premiums are expected to increase by about 20% on average if ACA subsidies are not renewed, with some people potentially seeing their insurance costs double or more. (31:25) This dramatic increase could force many to go without coverage.

Compelling Stories

Available with a Premium subscription

Thought-Provoking Quotes

Available with a Premium subscription

Strategies & Frameworks

Available with a Premium subscription

Similar Strategies

Available with a Plus subscription

Additional Context

Available with a Premium subscription

Key Takeaways Table

Available with a Plus subscription

Critical Analysis

Available with a Plus subscription

Books & Articles Mentioned

Available with a Plus subscription

Products, Tools & Software Mentioned

Available with a Plus subscription

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