Gratitude Week: Part II

Grateful for My Mistakes

It’s easy for most of us to be grateful for the people in our lives, the opportunities we have, or the moments that go our way. But, this morning, I was reflecting on the things that got me here and that got me thinking that…

I’m really grateful for some of the big mistakes that I’ve made over the years.

Like most of us, there have been plenty of mistakes, more than I can count or even remember. But a few big ones stand out. Not because they were pleasant, but because they had such a profound impact on my personal life and career and in ways that success never could. Each of these big mistakes encouraged me to reconnect with my values, rethink my assumptions, and embrace a growth mindset instead of being defensive about my or doubling down on unhealthy patterns.

Those mistakes didn’t just teach me something — they changed me.

A Mistake That Changed How I Lead

One of the biggest mistakes that I’ve made in my career came during my time leading engineering for pre-IPO company Captura. As we pushed for years toward going public, I convinced myself that the long hours, the relentless pace, and the strain it put on my health and the people who mattered were just “part of the job.” I assumed that once we made it to the finish line, the compromises that I was making would feel justified.

I didn’t set the boundaries, invest in my own development as a leader, take time to understand my values or purpose; consequently, I didn’t protect my health, my relationships with family and friends suffered, and I really felt misaligned.

Spoiler: 9/11 happened and we never did take this company public.

Years later, I’m grateful for that experience. It taught me that ambition is really meaningless without alignment. And it pushed me toward a more mature, balanced, and growth-minded approach to leadership.

A Choice That Changed How I Decide

Throughout my Microsoft career, travel was a constant, and somewhere along the way I normalized making big professional decisions on my own, assuming my family would simply adapt.

I had always wanted to go to graduate school; not so much because of the career advancement opportunities but more because of the career enrichment value. After the experience at Captura and becuase of the travel commitments of my role, I didn’t feel like I had the time while working at Microsoft, so I decided that going to graduate school was one of my goals AFTER I retired. But I made this decision without getting enough support from my family. I jumped in because I finally had the time. My family assumed retirement meant more time with them, not another major commitment I’d made on my own. There was a bit of resentment, missed opportunities to spend time with those that I cared about and while I loved going back to school, loved INSEAD and really value the network that I built during this experience, not being aligned with my family took the edge off of this experience.

I’m grateful for that lesson. It taught me that important decisions, even the ones that seem personal, still require alignment, partnership, and conversation. A growth mindset means recognizing when I need to engage the people who matter most, not simply assume they'll understand and support.

A Decision That Made Me Rethink Leadership Capacity

One of my roles at Microsoft involved building and supporting engineering teams around the world — Cairo, Rio, Wroclaw, Suzhou, Hyderabad, London, Paris, Munich, Sydney, and Johannesburg. It was an interesting and career-accelerating chapter, and I learned a lot from working across so many cultures. But one of the mistakes I made in scaling these teams was moving too quickly without building the leadership bench or cultural foundation needed to support a distributed organization. Without that structure, the team needed more involvement from me than was healthy or sustainable.

I’m grateful for the clarity that mistake brought. It sharpened how I think about org design, leadership capacity, cultural intentionality, and autonomy. It taught me that scaling isn’t about headcount, it’s really about capability.

A Mistake That Changed How I Approach Hard Things

A few years ago, when I ran my first marathon, I made the classic rookie mistake: I convinced myself I could skip a lot of the training and still show up strong on race day. I finished the marathon, but it sucked far more than it needed to. What should have been a meaningful milestone that I celebrated became a long lesson in the importance of training and preparation.

Training doesn’t eliminate discomfort; but it does a great job of distributing it. When I skip the workouts, all of that discomfort lands on one day, but if you’re committed to regular workouts, those short bursts of discomfort are more manageable and make race day more of a celebration.

Leadership works the same way. The hard moments aren’t always avoidable, but preparation turns them from being overwhelming into something that’s more manageable.

When we invest in daily habits like preparation, communication, alignment, boundary setting we spread the effort out. The work becomes sustainable. But when we skip those steps and try to power through, that concentrated discomfort is what eventually turns into burnout.

The Common Thread

In all of these examples of mistakes, I have tried to understand the lesson, even if sometimes I didn’t learn the lesson until much later. These experiences strengthened my understanding of the importance of alignment and sustainable leadership.

I don’t wish these mistakes away. They’re part of the journey, and honestly, they’ve taught me more than many of the successes I’ve had along the way. The mistakes themselves weren’t gifts but the growth that came from them absolutely is, and I’m grateful for that.