Pre Retirement Navigated

Will Hoffman
  • 5.0 (1)
  • Investing
  • Updated Weekly

The rules of money change the day you retire. Is your financial plan ready for the flip? For the last 30 years, you’ve followed a standard wealth accumulation playbook: save more, stay invested, ignore the daily market headlines, and let time do the heavy lifting. And those rules worked—they got you to the finish line. But the five years before you retire require an entirely new operating system. The moment you transition from saving money to living off of it, the playbook completely reverses. Time becomes your biggest constraint, asset growth takes a backseat to strategic tax mitigation, and your investment stance must pivot from pure offense to ironclad defense. Hosted by Will Hoffman, founder and president of Hoffman Wealth Management, Pre-Retirement Navigated draws on 23 years of real-world advisory experience to guide you step-by-step through the critical 5-year countdown to retirement. This isn’t a show about high-level theory or generic numbers. This is a tactical, unscr

Episodes

  1. Jul 29

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

    “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: Download the Free Pre-Retirement Checklist:  — Analyze where you currently stand, where you need to go, and what work still needs to be done. Book a Complimentary Discovery Call: — Schedule a zero-pressure conversation with our team to discuss your specific timeline and see if we’re a fit. Watch the Companion YouTube Video Series: — Prefer a more formal, scripted, and structured video breakdown?

  2. Jul 22

    5 Years to Retirement: Key Decisions You Must Make

    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: Download the Free Pre-Retirement Checklist:  — Analyze where you currently stand, where you need to go, and what work still needs to be done. Book a Complimentary Discovery Call: — Schedule a zero-pressure conversation with our team to discuss your specific timeline and see if we’re a fit. Watch the Companion YouTube Video Series: — Prefer a more formal, scripted, and structured video breakdown?

  3. Jul 15

    The Rules of Money Change the Day You Retire: Here is the New Playbook

    In this episode, Will Hoffman introduces the Pre-Retirement Navigated series, focusing on the six key flips and rule changes in the five years leading up to retirement. He shares insights on planning, decision-making, and emotional control to ensure a smooth transition into retirement.

  • 3 Episodes

About

The rules of money change the day you retire. Is your financial plan ready for the flip? For the last 30 years, you’ve followed a standard wealth accumulation playbook: save more, stay invested, ignore the daily market headlines, and let time do the heavy lifting. And those rules worked—they got you to the finish line. But the five years before you retire require an entirely new operating system. The moment you transition from saving money to living off of it, the playbook completely reverses. Time becomes your biggest constraint, asset growth takes a backseat to strategic tax mitigation, and your investment stance must pivot from pure offense to ironclad defense. Hosted by Will Hoffman, founder and president of Hoffman Wealth Management, Pre-Retirement Navigated draws on 23 years of real-world advisory experience to guide you step-by-step through the critical 5-year countdown to retirement. This isn’t a show about high-level theory or generic numbers. This is a tactical, unscr

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