Gratitude Week, Part III
Thankful for Risk
When I look back at the biggest inflection points in my life, many share a common thread: each required taking a significant risk. Those risks didn’t just shape my career and personal life, they reshaped who I became as a leader.
This week, I’m grateful for these risks, below are a few of the more notable risks.
Quitting a Job That Wasn’t Right
Long before Microsoft, I spent a year working in IT inside a cost center. It was the first time I felt genuinely constrained as a software engineer, cost control was more important than innovation. The work wasn’t bad and neither was the culture, but it wasn’t me.
Leaving that job without another one lined up felt reckless at the time. But it taught me something that’s guided every major move since, that a misaligned role is a terrible way to make a living. I took it as a sign to move on, not something to tolerate. Walking away opened the door to better opportunities and gave me the confidence to choose environments where I could grow, contribute, and lead with energy.
Moving Our Family to London
While I was working in Microsoft’s Online Services and as Bing grew, Microsoft made a decision to scale the business outside the U.S., and suddenly there was an opportunity to build and lead a new engineering organization and be based in London, Paris, and Munich. Without much time to analyze the decision, my family and I made the decision to move abroad; from the time that I found out about the role, to relocating to London, it was about 8 weeks.
In many ways, it was a startup inside of a global company, we had to find our own office space, build recruiting systems, and shape culture from the ground up.
That move became a turning point. It expanded my global horizons, stretched me in a lot of different ways, and set the trajectory for the rest of my career at Microsoft. From that moment on, I led international organizations for the remainder of my time at the company. None of that would have happened if I had waited for certainty about this role.
Launching My Own Business
When I launched Milestone Leadership early this year, I didn’t know if I would enjoy all the aspects of leading a business and worse, I didn’t know how I would handle it if I struggled to find clients. Fortunately, I found a colleague who was excited to take on parts of the business that I am not excited about, and I have enough client opportunities so that I have the freedom to choose the work that matters, collaborate with leaders I admire, and decide how much I work and when.
Launching my own business required new levels of clarity, resilience, and trust. It also opened doors I wouldn’t have seen if I had stayed on the safe path.
Each of these decisions came with doubt at the time. None were guaranteed. But each became a catalyst for growth, alignment, opportunity, and purpose.