Sometimes things are hard.
Sometimes things are hard, not just hard for you, but just really hard.
And sometimes you can’t always tell which is which, until after the hardship has passed.
This post is something of a personal story, but based on the positive responses I’ve received to my post on being a PM at Microsoft, I suspect that there might be someone out there that might find some lesson or inspiration or something in the story.
In the summer of 2011 I moved my family from upstate New York to Redmond, WA to join the SQL Server Integration Services[1] PM team. I’d been an SSIS MVP before joining Microsoft in 2008, and this felt like a real dream job. I could help the team finish and ship SSIS in SQL Server 2012, and then make the next version of SSIS better than it could otherwise be.
Except it didn’t quite work out that way.
In reality, I was joining a part of Microsoft that was at the forefront of the massive wave of change that transformed the company into the Microsoft we know today. Everything was in flux, from roles and responsibilities to ownership and processes, to the fundamental questions of what products and services we would build and ship. The 18 months that followed was a series of large and small reorgs, and every time I felt like I was getting my feet under me, everything seemed to change again.
People around me seemed to be rolling with it, and adapting to the new reality. For me, it was chaos, and I floundered. Even though I had worked for Microsoft for three years, this was my first technical PM role. I made it through, but it was one of darkest periods on my adult life. It was hard. It almost broke me, and I thought it was me.

Later on in 2014 I was working as a program manager on the first generation of Azure Data Catalog, and I was interviewing a new member of the PM team. For the purposes of this story[2] I’ll call this new PM Rick. Rick was a veteran PM who had shipped multiple major features in SQL Server and the first releases of SQL Azure, so he was interviewing the team as much as we were interviewing him.
During the interview, Rick asked me to tell my story – how did I end up where I was, where had I worked, what did I do, that sort of thing. So I told him my story, and when I got to the summer of 2011, he inhaled so sharply that I paused. I looked at him, and saw a look of surprise and respect[3] on his face. He looked at me, and he said:
Damn. You dove into the fucking blender.
He then went on to talk about how in his experience this time and place was the epicenter of unprecedented change and disruption that saw many veterans struggle – and saw many of them decide to look for opportunities elsewhere.
Rick and I worked together for for the next year and a half, and I learned a lot from him over that time. But I think the most important lesson I learned was that it wasn’t just me. I’d thought I was going for a swim in familiar waters, but I had actually dived into a blender, and I managed to get out with most of my extremities still attached.
That’s the story.
I think there’s a lesson in there somewhere about not giving up, about being true to yourself, and about doing what you think is the right thing to do, even when it feels like nothing you do is making any difference on the world of struggle around you. This would be a great lesson, if it’s actually in there.
The lesson that I know is in there is that sometimes things are really hard, and it’s not just you. This isn’t a nice lesson or an easy one, but that doesn’t make it any less real.
[1] SSIS FTW!!
[2] Also because it is his name.
[3] I’m not the best at reading emption, so I honestly don’t know if there was any respect there, but it sounds good so I’m going to roll with it. Rick can correct me if he needs to. He knows where I live.
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Outstanding, man. Thanks for your story.
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