A Crossroads After Three Decades

Exploring the space between what has been and what could be.

A Crossroads After Many Years

After nearly thirty years at Microsoft, I am spending more time than I expected thinking about a simple but significant question. I am trying to understand whether I should continue on the path I know or whether it is time to step into something different.

The recent Microsoft Voluntary Retirement Program offer brought this question into sharper focus. It encouraged me to look beyond the practical considerations and think about how I want the next phase of my life to feel. This has become less about career planning and more about the shape of my days and the way I want to use my time.

The Weight of Long Experience

Working at one company for this long creates a relationship that is hard to describe to anyone who has not lived it. Companies change and reorganize, but the years attach themselves to the places where we spend them. My children were born & grew up during this time. Many of my closest friendships began here. My understanding of the world was shaped by the work, the people, and the experiences that filled these decades. Microsoft became the setting for most of my adult life.

The Pull of the Present Moment

This reflection is happening during one of the most interesting periods I have seen in technology. AI is reshaping the industry at a pace that is both exciting and unpredictable. Being inside Microsoft during this transition offers a view into ideas long before they reach the public. I still enjoy the work. I still enjoy the people. I still enjoy learning. These are not small things.

The Possibility of a Pause

Even with all of that, a thought has been growing over the past couple of years. I have been wondering what it would feel like to pause for a while. Not to retire in the traditional sense, but to step away from structure and routine long enough to reset and see what rises to the surface.

For most of my career, responsibility shaped my choices. When my children were young, stability mattered more than risk. Friends approached me with compelling startup ideas, and I stepped away from all of them because consistency for my family felt more important. I still believe those decisions were right.

Life has changed. My children are now adults. The constraints that once guided every major decision no longer feel as fixed. This shift creates room for questions I never explored fully.

Curiosity Without Obligation

I think about building AI and IoT projects simply because they interest me. I think about traveling without fitting everything into short windows between commitments. I think about sailing across an ocean because it has been a personal goal for many years. These ideas matter to me in ways that are not tied to career progress.

I have also found myself drawn toward subjects outside technology. Social anthropology and psychology have become areas of curiosity. I am increasingly interested in how people behave, how culture shapes decisions, and how meaning is formed. Technology moves quickly, but human nature changes slowly, and that contrast has become more compelling with time.

There are days when I imagine a complete reinvention. That could mean co‑founding something with friends. It could mean returning to technology in a different role. It could mean earning a Captain’s License and spending part of my life on the water. These ideas once felt unrealistic. Now they feel like possibilities worth examining.

The Momentum of Identity

One of the challenges of reaching this stage is realizing how easily continuity becomes automatic. You follow the same path because it is familiar. People come to know you through a certain role and a certain identity. Over time, that identity settles around you in a way that is almost invisible.

Then an opportunity appears that allows you to step outside it, and you discover how difficult that step can be.

Part of me feels connected to Microsoft because it has been woven into so much of my life. Another part wonders whether there is value in stepping away while I still have the energy and curiosity to explore new directions.

Where I Stand Now

I do not have an answer yet. Some days staying feels right. Other days the idea of reclaiming time and possibility feels equally right. What I know is that this decision has encouraged me to think carefully about how I want the next chapter to feel, not only how it should look on paper.