In May of 2025, Brandi and I were in Fiji celebrating our 25th wedding anniversary. Twenty five years has a way of making you look at life differently. You start thinking less about noise and more about direction. Less about titles and more about peace. Less about what something used to be and more about what it actually is now. Sometimes in that reflection, we realise the undermined resilience value in our own stories and experiences.
While we were there, we talked about the future. I told her what I had been feeling about leadership, the challenges, and the strange weight of still caring deeply about the work while feeling like something had shifted. Maybe it was the organization. Maybe it was leadership. Maybe it was me. The honest answer is probably all three.
When I got back, I started what I now think of as the long kiss goodbye. I began trying to move to another team, not because I wanted a dramatic exit, but because I wanted a reset. A new room. New problems to solve. A chance to build again inside the same house.
Just under a year later, I finally moved. New team. New work. New people. A new chapter.
Then four days later, Microsoft announced the retirement offer.
Four days.
You almost have to laugh at the timing because the alternative is staring at the wall like it owes you an explanation.
At first, I tried to look at the offer fairly. I tried to separate emotion from math. I tried to ask the practical questions. What does this actually provide? What does it protect? What does it make possible?
Then I read the actual terms.
The healthcare piece offered up to five years of continued access to Microsoft medical, dental, vision, and wellbeing coverage. But only year one is subsidized. Years two through five require a monthly premium. So yes, there is access, but access is not the same thing as security.
The cash lump sum was up to ten weeks of base pay. The formula was one week of base pay for every six months of continuous service, with a minimum of eight weeks and a maximum of thirty nine weeks. That word matters. Continuous.
I have been connected to Microsoft for over 20 years, with a gap in the middle. That history matters to me. It shaped my career. It shaped how I think. It shaped how I work, troubleshoot, lead through problems, and show up when things are broken and people need answers. But because the service was not continuous, the offer does not honor the full story. It only counts the most recent stretch.
Then there is the stock piece. Six months of continued scheduled vesting for unvested stock awards. Again, something is better than nothing. But six months is not a grand gesture. It is not a bridge to a new life. It is a limited extension wrapped in corporate language.
So when I add it all up, the conclusion is simple.
There was nothing generous about the offer.
It was not generous for the years invested. It was not generous for the experience carried. It was not generous for the institutional knowledge built. It was not generous for the late nights, the escalations, the customers, the lessons, or the value still on the table.
It felt less like honoring a career and more like calculating a clean exit.
And that changed something in me.
Before reading the terms, I was wondering whether the writing on the wall meant it was time to leave. After reading the terms, I realized the offer was not worthy of my exit.
So I am staying.
Not because I missed the signal. I saw it.
Not because the offer was good. It was not.
Not because everything suddenly feels fine. It does not.
I am staying because the math did not match the moment. I am staying because my value is still greater than what was put on paper. I am staying because bad leadership does not get to write the final paragraph of my story.
This is where resilience stops being a motivational word and becomes a decision.
Resilience is not pretending something did not bother you. It is not smiling through disrespect and calling it growth. It is not accepting less than you are worth just because someone packaged it nicely. Sometimes resilience is looking at the situation clearly, admitting it was insulting, taking the hit, and then deciding that it still does not get to define you.
That is a big part of why I wrote Undermined. The book is about pressure, survival, betrayal, grit, and the part of a person that refuses to disappear just because the world tries to bury them. That theme feels very real to me right now. Not in a fictional way. In a lived way.
You can find Undermined here: www.undermined.com
This is not about being replaced by AI. That is the easy headline right now, but it is not my headline. I have spent my career adapting to technology. Change does not scare me. What bothers me is the gap between the value individual contributors bring and how that value is sometimes viewed from above.
As an IC, you know the work at ground level. You know the customers, the systems, the history, the risk, and the problems hiding behind the clean slide deck. You know the outages that did not happen because someone saw the issue early. You know the customer escalation that never became a crisis because someone knew exactly where to look.
That is the disconnect.
The better you are at preventing fires, the less visible your work can become. The more useful you are, the easier it becomes for the system to consume your value without truly protecting it.
And this offer made that clear.
So yes, I read the writing on the wall. But I also read the offer. And the offer was not enough.
It did not create enough safety. It did not create enough runway. It did not honor the full story. It did not make walking away the right decision for my family.
So now I am fired up.
I am staying to win. I am staying to build. I am staying to prove that a bad management chapter does not define the whole book. I am staying because the new team deserves the best of what I bring, and because I am not handing over the ending to people who never fully understood the story.
Maybe the rest of the story is not that I left.
Maybe the rest of the story is that I looked at the offer, saw it for what it was, and decided my story was worth more than that.
The writing may be on the wall, but that does not mean I have to accept the first exit ramp offered.
So I will keep showing up. I will keep solving problems. I will keep learning the new room I fought to get into. And I will do it with my eyes open.
Because sometimes the next adventure is not walking away.
Sometimes the next adventure is staying, winning, and making damn sure the wrong people do not get the last word.
That is resilience.
That is the next chapter.
And if there is one thing I know from life, work, marriage, and even writing Undermined, it is this: being underestimated is not the end of the story.
Sometimes it is the fuel.
