2 Years to Retirement: How to Turn Your Assets Into a Paycheck

2 Years to Retirement: How to Turn Your Assets Into a Paycheck

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Two years out from retirement is the critical turning point where your financial strategy must transition from a paper model into a real, dependable monthly paycheck. On this episode of Pre-Retirement Navigated, host Will Hoffman, founder and president of Hoffman Wealth Management, breaks down the key steps to moving your retirement income plan off the spreadsheet and into your actual checking account.

Data from the Employee Retirement Income Benefit Research Institute reveals that 54% of retirees are surprised by their actual living costs, while 36% experience major, unexpected spending events shortly after leaving the workforce. In this discussion, Will addresses how to insulate your portfolio against these irregular expenses without putting your long-term income sustainability at risk.

In this episode, we cover:

  • The “Payroll Department” Shift: How your day-to-day dynamic changes when you stop receiving W-2 withholding and become responsible for managing your own retirement tax payments.
  • Mitigating Tax and Penalty Risks: Key strategies to prevent costly IRS underpayment penalties—which totaled over $1.3 billion in 2024—and how to keep income within thresholds to avoid higher Medicare IRMAA surcharges.
  • Smart Account Sequencing: How to thoughtfully coordinate distributions across traditional IRAs, Roth accounts, and taxable brokerage accounts to optimize your tax efficiency.
  • Planning for “Lumpy” Spending: Establishing cash buffer strategies to handle home repairs, health needs, or family support without forcing emergency liquidations during market dips.

Whether you are exactly 24 months away from retiring or preparing for your next financial phase, tune in to learn how to structure a predictable income stream and navigate the transition with confidence.

 

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