Microsoft’s Great Flattening: 62-Year-Old Gets Flatter Than Org Chart

Meet Joe Friend: a 62-year-old Microsoft lifer with three separate stints since 1994, who just got booted in May 2025 during the 'Great Flattening'—Microsoft's polite way of saying 'we cut 15 managers including him and 14 others like a bad Netflix series renewal.' Joe, who had a sacred retirement plan hinging on making it to 65 for prolonged stock vesting, now suddenly can’t even snooze his alarm for that three-year countdown. After 30 years toggling between Microsoft, nonprofits in Indonesia, and Stack Overflow, he got surprise-dumped with a 'very comfortable' severance. Now he’s 'semi-retired,' supporting a young entrepreneur instead of coddling corporate suits—as he famously puts it, opting for $50K doing something fun over Big Tech money betrayals.

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Source: Businessinsider | Published: 10/25/2025 | Author: Jacob Zinkula