According to Business Insider, Mike Kostersitz spent 31 years at Microsoft before being laid off in May at age 60. He was among 120 people cut from his Azure team in a single meeting, part of broader Microsoft layoffs affecting about 6,000 workers. Despite landing interviews with companies like Nvidia and Nike over five months, he still hasn’t secured a job. Microsoft’s “55 and 15” policy allows his stock to continue vesting, giving him financial runway, but he estimates only about two years before needing to tap retirement funds. His experience mirrors thousands of tech workers facing an industry-wide hiring slowdown despite overall low unemployment.
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The brutal reality for experienced tech workers
Here’s the thing that really stands out about Kostersitz’s story – this isn’t some junior employee who got caught in restructuring. We’re talking about someone with three decades of institutional knowledge who was building Microsoft‘s cloud future. And he still got the impersonal Zoom firing along with 120 “anonymous faces.” That tells you everything about how corporate America views loyalty today.
His struggle to find new work despite that experience reveals something deeper happening in tech. Companies say they want experienced leaders, but when someone actually has that experience, they get penalized for it. Kostersitz had to “de-age” his resume by cutting everything before 2003. Basically, 20 years of his career became unmentionable because it might make him seem too old.
The interview experience puzzle
This part really hits home – Kostersitz describes getting “tell me about a time when” questions and having 30 years of stories to choose from. But that’s actually a disadvantage in today’s standardized interview processes. When you’ve seen everything, how do you pick the one anecdote that will resonate with someone half your age conducting the interview?
And think about this: he spent years on the other side of the table making hiring decisions. Now he’s discovering that being qualified doesn’t necessarily mean you can navigate the modern job search gauntlet. He actually hired a career coach to help with basics like LinkedIn and cover letters. After 31 years at one of the world’s most successful companies, he needed professional help to market himself.
The privileged but precarious position
Let’s be real – Kostersitz is in a much better position than most laid-off workers. Microsoft’s retention policies and his savings give him a two-year cushion. But that safety net creates its own psychological pressure. He’s basically watching his financial runway shrink every month he’s unemployed.
The retirement question looms large too. At 60, he’s caught between wanting to work and facing the reality that retiring now would mean a “huge change of lifestyle.” So he’s stuck in this purgatory – too experienced for many roles, not quite ready to retire, and competing in a market that’s increasingly hostile to older tech workers.
It’s an endurance game now
The most telling advice he got from his Microsoft-provided career advisor? “It’s a game of chicken right now. The person who has the longer breath and can stick it out longer will get the job.” That’s a pretty bleak assessment of today’s job market – it’s not about qualifications or fit, but about who can withstand the psychological toll longest.
Kostersitz’s story should worry anyone in tech, regardless of age. If someone with his credentials and experience struggles this much, what does that say about the industry’s commitment to its workforce? And what happens when the next wave of AI-driven efficiency cuts comes? The rules have changed, and even three decades at Microsoft doesn’t guarantee you understand how to play the new game.
