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Planning Season Looks Different After ESTO

By Kristen Gray
September 18, 2026
Photo collage from ESTO 2026 in Philadelphia, with a large red ESTO letter sculpture in the center, a keynote session on screens reading "Ideas That Travel," a group selfie, a slide reading "Change is inevitable but our growth is optional" and a selfie in front of the Rocky statue.

Three weeks out from ESTO and I am still thinking about it.

The Grand Ballroom at the Philadelphia Marriott Downtown was packed with the people who run destination marketing for states and cities across the country. What got me, right from the start, was watching everybody scribbling down notes. 

It’s easy to forget that for a lot of these teams, this is their ideation time. It’s a time of inspiration when the rest of the year they might just be reacting to fires and to whatever is next on the calendar. 

So people were using every minute of it, and you could feel that energy in the room.

That is kind of the whole heartbeat of this event for me. It brings the entire travel and tourism marketing industry into one room for three days so we can make the meaningful connections we don’t get to make from our desks, trade ideas about what is actually working, and figure out how to be better at this together.

I didn’t expect how many ideas from that week would still be with me three weeks later. It started, of all places, with a book that was just sitting out on the tables.

The More We Know, the Less We Question

Diana Kander gave the Monday keynote, “Unleash Your Curiosity,” and her book, Get Curious and Grow, was sitting out as we entered the room. I grabbed one and was hooked almost immediately. Honestly, the talk could be this whole post, there were that many nuggets packed into it.

Her big idea, and this is the one that has stuck with me the most, is that the more we know, the less we question. It makes sense once you sit with it. 

The longer you run a destination or a brand or a team, the more your own hard-earned expertise ends up building blind spots you cannot see from the inside, because you already know how this works, so there is no need to question it.

She told a story about an accounting firm that had a name for the blind spot. SALY stands for Same As Last Year, and everyone in the office referred to it as “Sally.”

SALY is the cozy blanket you reach for every time planning season rolls around; we did (x) last year, so sticking with the same thing is comfortable, safe, and low risk.

I have not stopped thinking about SALY since.

From there, she addressed “organizational zombies,” which is basically the same idea applied to your actual workload. Projects, meetings, processes, the things that keep shuffling forward year after year because nobody has stopped long enough to ask if the value they create is actually worth the effort they take. If it is not, it is a zombie. Kill it.

And then additive bias, which might be the one I think about the most day-to-day. 

We have this weird idea that if we keep adding to our plate, we are being more productive, when honestly it is usually the opposite. So the better question is not what else should I take on, but what can I take away? What can I declutter?

Out of the key takeaways, the one that still lives with me the most is her question about heads in beds. Are we running this because we have always run it, or because it will put heads in beds? In other words, what’s running on autopilot and what’s actually creating value and impact? 

Photo collage from ESTO 2026 showing the awards ceremony stage reading "Cheers to Travel's Best," a group photo with awards finalists, a selfie outside Reading Terminal Market, a Rocky mural reading "Yo Philly, Keep Punching," a view down the Philadelphia parkway and a photo at the Rocky statue.

The Sessions I Got the Most Out of Were the Ones We Worked Through Together

A lot of the program ran on roundtables, and those ended up being my favorite part. We took a topic to our table, workshopped it, and if we landed on something good, we raised our hands and shared our findings with the rest of the room.

AI was everywhere. I counted eight sessions with AI in the title across three days, plus a whole track just on discoverability and where search is headed. If you’ve been wondering whether you’re behind on it, you’re not, because everybody in that building was asking the same questions you are.

Social media came up constantly, mostly as a wish. A lot of people I talked to want a dedicated social media marketer on their team, and in the meantime, it is the director or whoever else actually posting. The same was true with budget and approvals. Most of what I heard was not really about what people cannot do, it was about what they would move on tomorrow if the yes came a little easier.

What made those tables worth it, though, was people actually bringing the real stuff: 

“I hit a wall on this.” 

“Here is what we tried.” 

“Here is what worked.” 

You leave knowing you are not alone in it.

Photo collage from ESTO 2026 with a "Welcome to Philadelphia" sign, a panel session on stage under a screen reading "Innovate, Collaborate, Celebrate," a stained glass window inside the venue, a slide reading "Never Goal Alone," a photo of Dolly Parton on a video screen and a bar decorated with baseball memorabilia.

Unplanned Meaningful Connections

Monday was the one night everyone was free, so we had dinner with the team from Travel Nevada. Small Mexican spot, chips and guac, a few empanadas, actual conversation, the kind you do not get on Zoom. It turned out to be some of the best hours of the whole trip.

And then it just kept going. 

We kept ending up together after that, lunch, breaks, the same faces in the lobby so often that  it stopped feeling like networking and started feeling like friendship. By Wednesday, I had stopped thinking about who I should talk to. I was just glad to see them.

It was my first trip to Philadelphia, and the city surprised me. It is actually laid out in these little pods. One block is a full stretch of restaurants, shops, a coffee spot, and then two streets over you are somewhere else entirely, a different name, a different feel, like its own small neighborhood. I loved that you could walk fifteen minutes and feel like you had traveled somewhere new.

None of those adventures were on the agenda. But that is the part I keep coming back to, the people you get closer to just by being in the same room for three days. You never know what comes out of that.

What I’m Taking Into Planning Season

Before I get into what is next, I have to say it: the ESTO planning team put together an incredible event, and it does not happen by accident. The U.S. Travel Association pulls this whole industry into one room every year, and that is not a small lift. So thank you to that team and to USTA for building something worth flying across the country for.

Now. SALY is coming for me this fall, same as she is coming for you.

I keep thinking about every program we ran last year, and every meeting still on the calendar because it has always been there. Kander’s question is the one I cannot shake: is this actually worth the effort it takes, or are we just comfortable?

I am picking one thing to run that question on. Not the whole plan, just the one I already suspect is a zombie.

I already know which one it is. I will let you know how it goes.

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