Update 01/26/2026: Due to inclement weather, M365 DC has been postponed. More information will be posted here as soon as it is provided. This post has been updated to reflect the date changes.

I didn’t quite plan this. For the second time in my life, both cities pulled me back.

I’m speaking at M365 Community Days in Washington, DC, and the very next weekend, M365 Miami. Same community. Two cities that shaped my life in very different, very real ways.

Washington, DC first.

DC is where I learned how to survive in this industry.

I was a consultant there, working with international organizations, non-profits, and the federal government. Ask my opinion on GCC. I navigated rooms where you had to be sharp, prepared, and twice as good just to be heard. As a minority in more than one way, DC taught me discipline. You learned how to read the room. You learned how to defend your ideas with facts, not vibes. You learned that credibility is earned, not given. DC didn’t coddle me. It made me better. It could have eaten me alive, but I was way too sour to swallow and too naive to realize. I made it out alive, with battle scars and stories to tell.

DC is also where I first experienced real community in tech. People who shared knowledge instead of hoarding it. People who answered questions without checking your title first. That mattered more than I realized at the time.

Then the follwing weekend, in the city I now call home, Miami…

Miami is where I learned how to breathe again.

I’ll also be sharing the stage with  Pete Simpkins, one of the best people I’ve met in this community. It honestly feels full circle, since the first time we spoke together was in his hometown of Minneapolis, on my birthday.

That’s what this community does. It follows you, city to city.

But back to Miami. That’s where the energy changed. New people, and a local community. A version of myself that finally felt aligned with who I am. Miami gave me room to build. To speak. To create. To show up loudly and unapologetically. After years of being made to feel smaller by rooms that were never built for me, I stopped shrinking. No matter what new challenges the world threw at me. I stopped asking for permission. I started trusting my instincts.

And yes, Miami is where I eventually became a Microsoft MVP. Not because I suddenly got smarter or learned more about SharePoint, but because I channeled everything I had into teaching others, just as much as they taught me over the years. I learned how to surround myself with people who cheered instead of questioned whether I belonged. DC taught me how to endure. Miami taught me how to live. Miami changed everything.

If you’ve read my story, you already know this community didn’t just help my career. It saved my life. That didn’t happen because of a logo, a title, or a badge. It happened because people showed up. Because I stayed present. Over and over again. In cities like these. In rooms like these.

So getting to be in DC and Miami on back to back weekends feels full circle. One city shaped me. The other set me free. Both gave me community. Both made me the Diego that you know today.

One more thing. If you see me at either event, you’re getting a hug. No awkward wave. No LinkedIn reminder. Community is built in human moments, not session decks.

If you’re on the fence about attending, take this as your sign. Come learn something. Come meet someone. Come be part of the thing that actually makes Microsoft 365 worth working in.

See you in DC. See you in Miami. Let’s keep showing up for each other.