Let's Go Upstate: The First Cohort
Senior higher ed leaders almost never get surprised in a good way at a work thing. But this week, thirty of them walked into a retreat in Saratoga Springs and got surprised.
It struck me because these are people who are almost always responsible for creating the experience for everyone else. They are the ones carrying the pressure, running the room, managing the expectations, solving the problem before anyone else sees it. Very few spaces surprise them in a good way anymore.
Most Professional Development Is Built Around Performance
Higher ed conferences are full of smart people saying smart things. That is not the problem. I love conferences. I’ve helped plan many of them over my career. In fact, I'm on the programming committee for AMA Higher Ed, which I will say without hedging is the single best room our industry gets all year. The programming is sharp, the people are the people, and the energy in that building is unmatched. I leave with a phone full of new contacts and a real sense that the field is moving forward together. Nothing else comes close, and helping shape it is bucket-list.
The problem is that many senior leaders arrive already exhausted by institutional pressure, shrinking teams, enrollment instability, political scrutiny, AI disruption, and the emotional weight of leading through prolonged uncertainty.
You can feel the performance layer almost immediately at many industry events. People stay on message. Conversations stay polished. Vulnerability gets edited down into a leadership anecdote with a clean takeaway and a pretty slide.
What happened at Let's Go Upstate felt fundamentally different because the room stopped performing for each other very quickly.
Why This Model Matters Right Now
Let's Go Upstate is application-based, free for attendees, and intentionally discussion-driven instead of performance-driven.
Senior higher ed marketing, communications, enrollment, and advancement leaders are carrying an extraordinary amount right now. The work itself has become more emotionally complex. Teams are smaller. Expectations are higher. The pace of change around technology and AI is accelerating. Many leaders are trying to hold institutional culture together while simultaneously modernizing it.
And most professional development models have not evolved to meet that reality.
We still confuse access to information with transformation. The internet already gives leaders unlimited access to frameworks, webinars, slide decks, podcasts, and tactical advice. What is increasingly rare is a room where experienced people can think out loud honestly without managing optics every second.
That is the thing I keep returning to after this first cohort.
The value was not just in the programming, it was in the permission structure. Permission to exhale a little and admit uncertainty. Permission to say the difficult thing out loud.
Those conditions change the quality of conversation entirely.
Three Days to Retreat
Three days. A chant of "Kelley! Kelley!" More jaunts than I can count. A cohort that arrived as thirty individuals and left as something else.
Snap, Squiz, and Kanahoma made this cohort free for every leader in the room, and they showed up as participants, not logos. Phil and his 5Tool team captured the memories. Saratoga Arms created a home.
I am writing this in my feels, which is the only honest way to write it.
To the first cohort: thank you. You did the thing we hoped someone would do with the space we made. Ashley and I are still catching our breath.
The fall cohort gathers September 13–16. Same place. Different crew.
If you're reading this and wondering whether to apply, or whether to sponsor, or whether something like this can really be what we're saying it is — it can. And it was.