After devoting two decades to Microsoft, 62-year-old Joe Friend never imagined his long career at the tech giant would end with a layoff. But in May this year, the veteran manager was abruptly let go — a decision that not only stunned him but also upended his carefully planned retirement.

“It feels like betrayal,” a Friend said in an interview with Business Insider, reflecting on how his 20-year journey at Microsoft came to an unexpected end. “I wasn’t surprised by the layoffs, but I was surprised to be caught up in them.”

When Friend, who worked as a Director of Product Management, first heard whispers of upcoming layoffs at Microsoft, he didn’t think much of it. With a solid track record and a team of nine reporting to him, he felt confident about his position.

But in May 2025, the shocking news came: his role was being terminated, along with 14 others from his department — including four managers. “I wasn’t entirely surprised by the layoffs,” he recalled. “I was surprised to get caught up in them.”

A Double Blow: Career and Retirement Plans Shattered

The layoff hit harder than expected because it forced Friend to rethink his entire retirement strategy. He had planned to continue working until he turned 65 — the milestone at which, under Microsoft’s policy, employees’ unvested stock grants continue to vest even after retirement or termination.

“I planned to figure out what I wanted to do over the next three years,” he said. “Then all of a sudden I’m at the doorstep, and I have to make that decision now.”

From Microsoft Word to Stack Overflow — and Back Again

Friend’s relationship with Microsoft began in 1994, when he joined as a Lead Program Manager on the Microsoft Word team.

After a few years, he took a break from tech to work with an international NGO in Indonesia — a move driven by his desire to live abroad and do meaningful work.

He returned to Microsoft in 2003 and stayed for another 14 years. But by 2017, burnout set in, prompting him to leave Big Tech behind.

For a while, he found solace at Stack Overflow, where the pace was different and the culture refreshing. But in 2018, Microsoft came calling again — and this time, the company seemed transformed.

“I was really impressed with what I saw as significant cultural change at the company,” he said. So, he returned — only to be laid off seven years later.

“It Feels Like the Unspoken Deal Is Broken”

After the layoff, Microsoft continued Friend’s pay through July and gave him what he described as a “very comfortable” severance package — nearly equivalent to his annual earnings. Financially, he says he’s fine. Emotionally, though, the experience has left a mark.

“It feels like a betrayal, and it impacts me financially, but it’s not going to hurt,” he said.

Friend now believes that the sense of loyalty that once defined Microsoft’s culture has faded. “It feels like the unspoken deal is broken,” he said. “If you perform well, you used to be rewarded and secure. I don’t think that’s true anymore.”

“I’d Rather Earn $50,000 Doing Something I Love”

As he plans his next steps, Friend is clear about one thing — he won’t be going back to Big Tech.

“I think I’d rather earn $50,000 a year doing something I’m excited about,” he said. “It doesn’t mean I won’t jump back into a job, but it certainly won’t be Big Tech.”

For someone who once believed in the promise of Microsoft’s culture, the sudden layoff felt less like a professional setback — and more like the end of an era.