Creating the Conditions to See What’s Coming Next

It happens every year. It’s late in the evening at the Jump Offsite, and more than a few of us have decided to stay up later than we should. The air has cooled off after a warm day in Napa Valley. We’re surrounded by the vineyards as we sit around a fire pit with a glass of wine in hand. We talk about a provocative idea we heard earlier in the day. We reflect on the amazing people we’ve gotten to know. That’s when someone turns to me.

“You know,” they say with a sheepish grin, “You’ve been bugging me to come to this thing for years. And every year I put it off. Don’t get me wrong—I love you guys—but I assumed this was just another conference. I really had no idea. This is something else entirely…” 

We both laugh because it’s a completely reasonable reaction. Some things just need to be experienced.

Take a Breath

We’re about six months out from this year’s Offsite, and I find myself thinking about conversations like that one by the fire. It’s a reminder to me of what we’re working to create. If we do the careful work of bringing the right group together and designing the right experience for them, we’ll all come away with something valuable.
 
Our clients have their work cut out for them. It’s a unique position to spend your days focused on issues of strategy and innovation. You’re expected to have a point of view on what’s coming next, even as the ground keeps shifting under your feet. You’re asked to make decisions that carry real consequences without the luxury of certainty. And you’re doing that work inside organizations that are still largely optimized for the present.
 
It’s easy to get buried in the day-to-day. Most people around you are doing exactly that. The near-term pressures have a way of pulling your attention inward. You can spend weeks or even months without lifting your head to take in what’s changing more broadly.
 
For instance, everyone knows that AI is huge. Most leaders have already made significant bets to leverage AI’s potential or forestall its threats. What’s less clear is what might happen. Will large language models get displaced by physical AI? Will agents completely disintermediate our business? The headlines come fast, but they rarely help you make sense of what matters most. At a certain point, you need to step back and create the conditions where you can see things more clearly.

We’ve been gathering people together at the Jump Offsite for over twenty-five years. Somewhere along the way, we stumbled into something special, and we learned a thing or two about what makes for a great experience. Here’s some of what we’re thinking for this year.

Create an Environment

Your perspective changes when you step away from the day-to-day and enter a place that invites reflection. The rhythm of the day shifts in subtle ways, and you find yourself lingering for a moment, perhaps paying attention to things you might otherwise rush past. Over time, your thoughts begin to quiet, and questions that felt tangled and blurry begin to unwind and come into focus.

That’s why we have the Offsite at the Carneros in Napa. I’ve stayed in hundreds of places, but very few have the energy that the Carneros does. Maybe it’s the little cottages. Maybe it’s the vineyards. This year, we’ve intentionally limited the size of the group to fifty participants, along with their spouses and partners. That’s not to be exclusive, but to ensure the experience remains intimate and personal.
 
We’ve been working on new elements as well. Our team is designing a new stage that will allow us to use technology in a way that changes how ideas are experienced in the room. Even the wine list has been tuned with care, because those shared moments in the evening matter more than people might expect. The goal is continuity with last year, with a steady push to make each element just a bit better. Over a few days, all of that care adds up in ways you can feel.

Gather Your Tribe

What gives the experience its real weight is the quality of the conversations. Each afternoon, we move into small deep dives with just five or six people in a closed-door setting. There are no recordings, and what’s said in the room stays in the room.

Something profound seems to happen in those conversations. People begin to speak more plainly about what they’re dealing with. A leader might talk about trying to shift an organization that isn’t ready to move. Someone else might describe the challenge of pushing their CEO to see further than they’re used to seeing. You hear stories about bets that haven’t paid off yet and the quiet doubts that come with carrying responsibility for the future of a business.

There’s a kind of relief in those conversations. You recognize pieces of your own experience in what someone else is saying. You realize you’re not the only one navigating these tensions, and the dialogue deepens from there. People listen more closely and respond from experience, and the work starts to feel shared.
 
That kind of exchange depends on who’s in the room. We put a great deal of care into bringing together the right group of participants. This year, we have a mix of long-time attendees and people joining for the first time. The industries range from consumer products to entertainment to technology and financial services. The titles vary—CTOs, CMOs, Chief Growth Officers—but the underlying responsibility is similar. These are people who are expected to help their organizations see what’s coming next and prepare for it.

The people who are most transformed by the experience are often the folks who most commit to the premise. They’re the ones who make it a true gathering of peers. They ask the most probing questions. They share their challenges most honestly. The people who are most surprised by what they experience are the ones who have most helped to make it so special.

Bring Big Ideas

And then there are the big ideas. Each morning, we hear from thinkers who have spent years working at the edge of what’s coming next. These are people who have been living deep inside a set of questions and have something real to say. The trick is to find people with particular relevance to the jobs we do.
 
I’m particularly excited about this year’s slate of speakers. Michael Pollan will be with us, exploring the nature of consciousness and what it means to expand the way we experience the world. His work brings together neuroscience, psychology, and lived experience in a way that challenges some of our most basic assumptions about how we perceive reality.

Michio Kaku will join us to talk about what’s unfolding at the intersection of quantum computing and artificial intelligence. He has a way of connecting ideas that can feel distant to the practical shifts they’ll drive across industries in the coming years.
 
Jamil Zaki will share his work on cynicism and empathy. While some people believe that a certain level of cynicism is always necessary, his research shows the opposite. Cynics lose out more than idealists. That has enormous implications for how we lead teams and make decisions under pressure.
 
We’ll also hear from a few operating CEOs, the folks I like to call frackers. These are leaders who are actively reshaping their industries. They’re building businesses that shift the ground under everyone else and force competitors to respond, whether they’re ready or not.

There’s a particular feeling that comes out of these sessions. It’s the moment when something clicks, and you realize that the frame you’ve been using may be too narrow for what’s actually coming. You begin to see your own context differently, and with that shift comes a sense that it may be time to move with more urgency than you had planned.

Preparing to Shift

Over the course of a few days, you start to notice things connecting that didn’t seem related at first. You take in new ideas and test them in conversation with peers, and you start to see patterns that weren’t visible before. Gradually, a sense of direction emerges. Not a fully formed plan, but a clearer understanding of what matters and how you want to show up when you return to your work.

And somewhere along the way, you let go a little. There are long dinners and conversations that stretch later than expected. People find themselves laughing more easily, continuing exchanges that feel worth having. Their spouses are right there with them. At one point or another, you end up on a dance floor, moving with a kind of abandon that doesn’t always make it into the workday. It’s a reminder that the work we do is serious, and that it helps to carry some lightness with it.
 
Because the Jump Offsite is a small gathering by design, many of the people reading this won’t be in the room this year. That’s simply a function of keeping the experience intimate enough for it to work. At the same time, the ideas and the shifts that come out of those few days have a way of traveling. They show up in the decisions people make, in the strategies they pursue, and in the organizations that get shaped over time.
 
In the next few weeks, we’ll finalize our participant list and turn our attention to tailoring the conversations. If you’ve been meaning to join us, this is the moment to act. We’d love to have you, but we’re nearly full.

Either way, the work continues. The future doesn’t slow down. It asks us to pay attention, to make sense of what we’re seeing, and to act with intention. For a few days in Napa, we’ll be doing that work together. At the main stage, in the deep dives, at the spa party, and at a firepit with glasses of wine in our hands.