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What You Need to Know About Open Enrollment

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November 25, 2024

TLDR: This podcast discusses when a Health Savings Account (HSA) with a high deductible plan might not be ideal, as well as factors to consider when deciding between such a plan and one with lower monthly premiums but higher deductibles.

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Open enrollment is upon us, and understanding your health insurance options can feel overwhelming, especially when it comes to high deductible plans and Health Savings Accounts (HSAs). This recent episode of The Money Guy Show delves into key questions, considerations, and strategies to help you navigate this critical time of year successfully.

Understanding HSAs and High Deductible Plans

While HSAs offer several tax advantages—such as tax deductions when contributing, tax-deferred growth, and tax-free withdrawals for qualified medical expenses—they're not a one-size-fits-all solution. Here are some essential factors to consider when deciding if a high deductible plan is right for you:

  • Employer Coverage: If your employer offers highly subsidized health insurance with low premiums and out-of-pocket costs, opting for a high deductible plan might not be beneficial.
  • Medical Needs: Assess your projected healthcare usage for the upcoming year. If you expect to require frequent medical services, a high deductible plan may lead to higher out-of-pocket costs compared to a lower deductible plan.
  • Cash Flow and Emergency Funds: Make sure your cash reserves can cover the higher deductible should you need to utilize your health insurance. Having an emergency fund that covers 12-18 months of living expenses is recommended for financial peace of mind.

How to Approach Open Enrollment Decisions

The episode emphasizes the importance of evaluating your healthcare needs and financial situation during open enrollment season. Here are key steps to take:

  1. Evaluate Past Costs: Review your previous year's healthcare expenses to gauge your medical needs.
  2. Compare Plans: Create a matrix comparing premiums, deductibles, and out-of-pocket maximums for each plan.
  3. Consider Tax Benefits: Analyze the potential tax benefits of HSAs. Determine how much can be contributed and factor in any employer contributions.
  4. Project Future Needs: Think ahead about possible medical expenses, including routine care or planned surgeries.
  5. Consult with Financial Advisors: If uncertain, consider seeking advice from a financial planner to help clarify the best decision for you.

Living Off Investments Before Retirement

In a separate segment, the podcast tackled a listener's query on utilizing stock investments during a temporary phase of no income while attending graduate school.

Key Considerations:

  • Withdrawal Strategy: Should you sell investments all at once or gradually? Selling gradually might let you exploit favorable market conditions.
  • Liquidity Needs: Ensure you have liquid cash on hand (12-18 months of living expenses) to avoid selling investments during market downturns.
  • Asset Allocation: Maintaining a healthy mixture of cash, equities, and possibly fixed income securities is vital for risk management in case of market volatility.

When relying on investments, especially in early retirement or during career breaks, consider your overall financial situation, tax implications, and the long-term impact of your withdrawals on future growth.

Emergency Funds for Dual-Income Households

Guests also discussed emergency fund adequacy for dual-income households, emphasizing that:

  • The baseline should generally be at least 3-6 months of living expenses, but this can vary based on income disparity among partners and any obligations from property ownership.
  • Separate emergency funds for shared expenses and personal needs might be beneficial to maintain transparency and reduce potential power dynamics regarding finances within relationships.

Investing in Employer Ownership

Another question tackled the opportunity of investing in company ownership shares. It’s essential to be cautious and ensure you:

  • Have a Solid Financial Foundation: This means addressing emergency funds and retirement savings before investing heavily in employee stock.
  • Manage Illiquidity Risks: Understand that investing in your employer can be illiquid—meaning it may not be easy to access funds if needed, impacting your financial security.

Conclusion: Make Informed Decisions

As open enrollment approaches, it’s essential to reassess your financial and health care needs critically. Remember, taking a proactive approach and making informed decisions can greatly affect your overall financial health and security. For more great insights and information about managing your finances, visit The Money Guy Show for our other episodes and resources.


In summary, engaging with your open enrollment choices, planning for emergencies, understanding how to manage investments, and being intentional with your financial decisions will set you up for success. Being financially proactive contributes to a fulfilled, less stressful life, enabling you to prioritize what truly matters.

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