May 26, 2026

Microsoft's Early Retirement Offer and What It Teaches Everyone Else

Microsoft's Early Retirement Offer and What It Teaches Everyone Else
Microsoft's Early Retirement Offer and What It Teaches Everyone Else
This Time Is Different
Microsoft's Early Retirement Offer and What It Teaches Everyone Else

Malcolm flies solo this week to break down one of the more generous early retirement packages in recent memory, and whether "generous" and "right for you" are actually the same thing. He covers:

- What makes Microsoft's offer different from a typical severance package (hint: five years of health care)

- The three-bucket framework for deciding if you can actually afford to say yes

- Why your RSU vesting window might matter more than the cash payout

- The tax trap hiding inside the year you accept, and how charitable giving can help offset it

- What saying no might actually be signaling about your job security


Host: Malcolm Ethridge

Engineer: Tim Sparks

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