In May of 2025, Brandi and I were in Fiji celebrating our 25th wedding anniversary. Twenty five years will make you think differently. It has a way of turning down the noise and turning up the truth. You start thinking less about titles and more about peace. Less about what something used to be and more about what it actually is now. Less about hanging on and more about making sure you haven’t undermined your next adventure, wherever that may be.
While we were there, we talked about the future. Not in some big corporate strategy kind of way. Not with charts, roadmaps, or polished language. Just two people who have been through enough life together to know when something feels off. I told Brandi what I had been carrying. I talked about leadership, the challenges, and the strange weight of still caring about the work while knowing something had shifted.
Maybe it had shifted in the organization. Maybe it had shifted in leadership. Maybe it had shifted in me. The honest answer is probably all of it.
When I got back, I started what I now think of as the long kiss goodbye. I was not looking for some dramatic exit. I was looking for a reset. A new room. A new team. A chance to build again inside the same house. Sometimes you are not ready to leave the whole place. Sometimes you just need a different hallway.
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 what else are you going to do? Sometimes life has a sense of humor, and sometimes that humor shows up wearing a benefits packet.
At first, I looked at the offer through the practical lens. What does it provide? What does it protect? What does it make possible? The offer included continued healthcare access, with year one subsidized and years two through five available with a monthly premium. It included a cash lump sum based on continuous service. It included six months of continued scheduled vesting for unvested stock awards.
Was it everything I would have wanted after being connected to Microsoft for over 20 years, with a gap in the middle? No. But at some point you stop trying to make the offer carry the full weight of the story. The offer is one piece. The timing is another. And the timing was impossible to ignore.
The writing was on the wall.
For a while, I thought maybe the next part of the story was staying and proving a point. Stay and win. Stay and build. Stay and make sure the wrong people did not get the last word. And honestly, there is still a version of me that likes that idea. I am wired that way. Tell me I am done and I will probably find another gear just out of spite.
But the more I sat with it, the more I realized I do not have to stay to prove anything to anyone.
That is a pretty freeing sentence.
Microsoft has been a major part of my life. It shaped how I think, how I troubleshoot, how I communicate, and how I solve problems. It gave me hard problems, smart people, stressful moments, great lessons, and stories I will carry with me for the rest of my life. There are people and customers who made the chapter matter. There are moments I am proud of. There are lessons I earned the hard way.
I am grateful for all of that.
But gratitude does not mean you have to stay past the ending.
You can appreciate a chapter and still turn the page. You can respect the work and still choose a new direction. You can be thankful for the opportunity and still know when it is time to take the exit ramp.
So I am taking the offer.
Not because I am defeated. Not because I am scared. Not because AI came along and suddenly I forgot how to adapt. That is not my story. Technology changing the work has basically been the work my entire career. Change does not scare me. I have been rebuilding, relearning, retooling, and figuring it out for years.
I am taking the offer because I can read the room. I can read the wall. And maybe more importantly, I can read myself.
This is not really about AI. That is the easy headline right now, but it is not mine. For me, this has been more about understanding the difference between the value an individual contributor brings and how that value is sometimes viewed from above.
As an IC, you live close to the work. You know the customers, the systems, the risks, the weird history, and the problems hiding behind the clean slide deck. You know the outage that did not happen because someone saw the problem early. You know the escalation that never became a crisis because someone knew exactly where to look. You know the kind of value that is very real, even when it is not always visible.
And after enough years, you learn something important. You do not always need the system to see your full value before you are allowed to believe it yourself.
That is not bitterness. That is clarity.
And clarity is a gift.
There is a difference between leaving angry and leaving awake. I am choosing awake. I am choosing grateful. I am choosing excited. I am choosing the part of the story where the road opens up and I get to decide what I build next.
That is where resilience comes in.
Resilience is not pretending the hard parts did not happen. It is not acting like every ending feels good. Resilience is taking the lessons, the scars, the frustration, the gratitude, and the fire, and turning all of it into forward motion.
That is a big part of why I wrote Undermined. That book is about pressure, loss, survival, betrayal, grit, and the part of a person that refuses to disappear just because life tried to bury them. Different season. Same lesson.
You can find Undermined here: https://undermined.com
This moment feels different, but the theme is familiar. You do not always get to choose what happens. But you do get to choose what it means.
For me, this means opportunity.
It means space. It means freedom. It means time to breathe, build, write, create, and chase the things that have been sitting in the back of my mind waiting for their turn. It means taking everything I have learned and pointing it toward something new. Maybe something mine. Maybe something unexpected. Maybe something I have not even seen clearly yet.
And that part excites me.
The old version of me might have needed to stay and fight the ending. This version of me is starting to understand that not every ending needs to be fought. Some endings need to be recognized. Some doors need to be walked through. Some exit ramps are not a punishment. They are timing.
Maybe the rest of the story is not that I stayed to prove a point.
Maybe the rest of the story is that I finally understood I no longer needed to.
The writing was on the wall. The offer was on the table. The timing was loud enough that even I could not ignore it.
So I am choosing the exit.
I will take the lessons. I will take the stories. I will take the friendships. I will take the hard-earned experience. I will take the scars and the gratitude with me.
Then I will do what I have always done.
Start again. Build again. Figure it out again.
On to the next adventure.
