Tag: Risk Tolerance vs. Capcity

What to Do 4 Years Before Retirement (Tax & Healthcare Prep)

What to Do 4 Years Before Retirement (Tax & Healthcare Prep)

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“I’m going to be in a lower tax bracket when I retire.”

It’s one of the most common statements we hear from folks in their early 60s. But as required minimum distributions (RMDs) kick in around age 73 or 75, many retirees discover that their deferred tax bill has simply ballooned into a future tax trap.

In this episode of Pre-Retirement Navigated, host Will Hoffman dives into Year 4 of the five-year runway to retirement. He explores how to stop thinking merely in terms of account balances and start thinking in terms of tax brackets.

Key Takeaways From This Episode:

  • The Tax Control Triangle: How to balance taxable accounts (capital gains), traditional pre-tax accounts, and tax-free Roth accounts to give yourself maximum spending flexibility.
  • The Hidden Cost of Delaying: How unmanaged traditional IRAs ($19.2 trillion nationally) trigger unintended consequences like IRMAA Medicare surcharges and higher Social Security taxation.
  • Strategic Roth Conversions: Why converting assets pre-retirement requires precision, accountant coordination, and an understanding of your current vs. future income goals.
  • Pre-Medicare Health Insurance Strategy: Why shopping networks and estimating healthcare costs four years early prevents costly, last-minute scrambles when leaving an employer

Whether you are 55 or 65, the decisions you make four years out set the foundation for a flexible, stress-free retirement.

📥 Episode Resources:

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5 Years to Retirement: Key Decisions You Must Make

5 Years to Retirement: Key Decisions You Must Make

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Five years out from retirement sounds like a long time. When you are driving to work every day or grinding through a job you are ready to leave behind, 60 months can feel like an eternity.

Because it feels so far away, Year 5 is the single window on the retirement runway that almost nobody uses well. Most people coast through it, assuming they have plenty of time to figure out the details later. But here is the reality: by Year 3 or Year 2, key strategic doors quietly close.

In this episode of Pre-Retirement Navigated, founder and president Will Hoffman walks through why Year 5 is the ultimate “table-setting” phase. When you tackle the foundational decisions right now, the rest of your transition into retirement becomes far lighter, clearer, and stress-free.

Key Takeaways from This Episode

  • Setting an Exact Exit Date: Why being ambiguous lets you off the hook, and how putting a real date on the calendar keeps you in control before health or employer changes force a decision.

  • The 2-Budget Framework: Why running two separate budgets—what you want to spend vs. what you need to spend—protects your lifestyle against market volatility and sequence-of-returns risk.

  • Running the Projections You’ve Been Avoiding: Why getting “bad news” 5 years before retirement is a gift that gives you time to pivot, save, or adjust your strategy.

  • Risk Tolerance vs. Risk Capacity: Understanding why loving growth isn’t enough when you are 60 months away from withdrawing living expenses from your portfolio.

  • Essential Structural Cleanup: Clearing out potential legal nightmares by auditing beneficiary designations, estate documents, healthcare coverage, and powers of attorney.

📥 Episode Resources:

Podcast: Play in new window | Download