Gianna's Gem: Imagine...Your most underrated superpower
/Hi there,
This past weekend, I went on a hike with my family to enjoy the first day of nice weather in a few weeks. No agenda, no deliverables, no Wi-Fi. Just trail, trees, and the three of us.
Somewhere between the first hill and the second water break, we stumbled into one of the most energizing conversations I've had in months… and it started with a single word: imagine.
Here's how it went. I turned to my family and said, "Let's play a game. Everyone has to start their sentence with 'imagine' and finish it however they want. Anything goes."
At first, there was a beat of silence… that slightly skeptical pause you get before someone decides to play along. And then the floodgates opened.
"Imagine if plants could talk… what would they be saying?"
"Imagine if we aged in reverse…so your wisest years were also your youngest."
"Imagine if there were no airplanes… would we still know people from other continents…would we still travel just in super high speed underground tubes?"
"Imagine… what the world will be like in 200 years."
"Imagine… if we had pet dinosaurs"
What followed was one of the richest, most joyful conversations we'd had in a long time. Questions led to theories. Theories led to philosophy. Philosophy led to laughter. We talked about time, about connection, about what we take for granted, about what the world could look like if we just tilted the lens a few degrees.
By the time we finished the hike, we were buzzing and not from caffeine or screens, but from the sheer exhilaration of thinking freely. Of imagining without limits. It was like a “runners high” for the brain.
And I couldn't stop thinking: why don't we do this more? And why aren't we doing this in our events?
Gianna's Gem: Imagination isn't child's play. It's the most powerful tool you have, AND it may be the most underused one in your professional life.
What Imagination Actually Does to Your Brain
Here's what's fascinating: when you engage in imaginative thinking, really letting yourself explore "what if", your brain activates the default mode network, the same neural system linked to creativity, empathy, and problem-solving. It's the opposite of the task-focused, heads-down mode most of us live in all day.
Imagination literally rewires how you see problems. It creates distance between you and your current reality, which is exactly the perspective you need to innovate, to design something new, to ask a question nobody has thought to ask.
Research shows that people who regularly engage in imaginative thinking… daydreaming, hypothetical play, creative exploration… demonstrate higher levels of empathy, resilience, and creative output. They're better at connecting disparate ideas. They're better at reading the room. They're better at solving problems that don't yet have a name.
And yet, most of us leave imagination at the door the moment we open our laptops.
Gianna's Gem: Imagination is not a soft skill. It's a cognitive superpower that sharpens every other skill you have.
Why We've Stopped Imagining
I doubt anyone would argue that we’re living in an era of notifications, to-do lists, back-to-back Zooms, and information that never stops coming like waves infinitely crashing in the ocean. The average adult makes over 35,000 decisions per day. Our brains are running full throttle just to keep up with reality…let alone to imagine a different one.
And then there's the cultural piece. Somewhere along the way, we started equating imagination with impracticality. We stopped asking "what if?" because someone, somewhere, told us it wasn't useful. That we needed to be realistic. That we needed a plan. Compared to the students who were obedient task masters, how often were the daydreamers in class rewarded for thinking creatively, even if at a slower pace?
But here's what I've learned after 23+ years in event planning: the people who create the most extraordinary events, the most innovative companies, the most meaningful lives… they are the ones who never stopped imagining. They just got better at building the bridge between imagination and execution.
My hike this weekend reminded me that imagination doesn't require resources or a strategy deck. It just requires the willingness to start a sentence with "imagine" and see where it takes you.
Gianna's Gem: The gap between a forgettable event and a transformative one is almost always found in the imagination of its creator.
Why I Think Imagination is the Missing Ingredient in Events
Here's something I've been sitting with since that hike: the events that have stayed with me the longes, the ones I still talk about years later, all had one thing in common. Someone, somewhere in the planning process, asked a truly imaginative question.
Not "what worked last year?" But: what if we flipped the whole format?
Not "what's the standard keynote setup?" But: what if the speaker never touched a stage?
Not "how do we make an incremental improvement" But: what if we took a moonshot this year?
Imagination in events shows up at three levels, and most planners only ever touch the first one.
Level One: The Format
This is where imagination is most underused. We default to formats because they're familiar; a welcome reception, a general session, breakout tracks, a closing dinner. And while structure matters, structure without imagination produces events that feel like every other event.
Ask imaginative questions about your format: Imagine if attendees never sat in a row facing a stage. What would they do instead? Imagine if the most important conversation of the event happened not in a session, but in an elevator or on a walking trail. How do we design for that? Imagine if we built the schedule backwards, starting from the feeling we want people to have when they leave and working forward. What would change?
When I was at Airtable, Google, and SoftBank Vision Fund, we radically reimagined what a user conference format could be, and the results were exactly what you'd expect when imagination takes the wheel: sessions that people remember years later, connections that turned into partnerships, and a community that felt genuinely built rather than assembled.
Level Two: The Creative Concepts
This is where most event planners spend their creative energy… and it's important. The theme. The visual identity. The surprise moments. The unexpected delight.
But even here, imagination is often constrained by "what's been done before." We look at Pinterest boards and past events and industry trends, which is useful, but it's also a ceiling.
True imaginative creative concepting starts not with inspiration boards, but with questions. Imagine if every element of this event told the same story. What story would we tell? Imagine if the venue itself was a character. What would it say? Imagine if every attendee left with one image burned into their memory. What would that image be?
Level Three: The Attendee Experience
This is where imagination becomes your greatest differentiator, and where it's most often forgotten.
Most event planners design for the average attendee. But imagination asks: imagine if we designed for the most introverted person in the room. What would change? Imagine if we designed for the person who almost didn't come. What would make them feel it was the best decision they made all year?
When you imagine the full range of human experience in your room, the person who's nervous, the one who's grieving, the one who flew six hours to be there, the one who's skeptical, the one who's desperate for connection, you start designing with a depth that people feel before they can even name it.
I used to plan the Women’s Events for Google and I remember coming up with creative concepts… a menu key for pregnant women (no aged cheese, raw fish, cured meats), a twist on the opening keynote which started in the evening after school duties were finished and featured passed champagne, caviar and chocolate tasting as women headed into the keynote…I even hired a technical crew that was 100% female and one of our performers gave that detail a shout-out during her fireside chat with Google’s CMO! I knew my audience and delighted them by catering to their very specific needs.
Gianna's Gem: Great event design starts with imaginative questions, not logistical answers. What if you spent 30 minutes imagining before you started planning?
How to Bring Imagination Into Your Events
Here are five concrete ways to infuse imagination into your event planning process and the experiences you create for attendees:
1. Start every planning session with an "Imagine" round. Before you open your budget doc or your run-of-show template, gather your team for five minutes of unrestricted imagination. Go around the table (or the Zoom) and have everyone finish the sentence: "Imagine if this event…" No filters, no practicality. Just possibility. You'll be surprised what surfaces.
2. Design at least one "What if" moment into every event. This is a moment that breaks the expected pattern and invites attendees to see something differently. It could be a question posed during a keynote with no answer given, or a session that starts with silence, or an activity that requires people to use their hands instead of their voices. One well-designed moment of imagination can shift the entire energy of a room.
3. Use imaginative prompts to facilitate connection. Take a page from my family hike. Conversation cards, imaginative icebreakers, or even a prompt projected on a screen during a networking reception can open people up far more than "so, what do you do?" Some of my favorites to use at events: Imagine if you could have dinner with any historical figure…who and why? Imagine if your company didn't exist… what problem would go unsolved? Imagine what you'd be doing if money were no object. These prompts create the conditions for real conversation, and real conversation is the whole point.
4. Build "imagine" spaces into your physical environment. Create literal spaces at your event that invite reflection and imagination: i.e. a lego wall where people can build their "imagine if" responses. Give people permission to slow down and think expansively, even in the middle of a packed conference day and in formats that utilize different brain pathways than usual.
5. End with imagination, not logistics. Most events end with "thank you for being here, safe travels." Instead, try closing with an imaginative prompt that sends people home thinking: "Imagine what becomes possible if you implement one thing you learned today. What would that be?" or "Imagine yourself one year from now. What does success look like?" This transforms your closing from a formality into a launchpad for real change.
How to Bring Imagination Into Your Own Life
What happened on that hike wasn't just fun. It was a reminder that imagination is a muscle… and like every muscle, it atrophies when you don't use it.
Here's how to start exercising it:
Play the "Imagine" game. You don't need a trail in the woods. You can do this at the dinner table, on a walk, in the car, or even solo in a journal. Start with "imagine if…" and let yourself go anywhere. The sillier and more unexpected, the better. Imagine if you had to describe your day to someone from 1850. Imagine if your morning routine were broadcast as a TV show. Imagine if your biggest professional challenge were actually a gift in disguise. What comes up?
Give yourself unstructured time. Imagination needs white space. When every minute is scheduled and every thought is task-oriented, there's no room for the creative brain to wander. Protect time, even 20 minutes a day, where you're not producing anything. Walk without a podcast. Sit without your phone. Meditate then visualize for 20 minutes…Let your mind go somewhere unexpected.
Ask "what if" before you ask "how." In our professional lives, we rush to execution. But imagination lives in the "what if" phase. Before you jump to solutions, spend time in the question. What if we approached this completely differently? What if the constraint we think we have isn't actually real? What if the answer is the opposite of what we're assuming?
Surround yourself with imaginative people. My family reminded me this weekend that imagination is contagious. When one person starts a sentence with "imagine," something unlocks for everyone in the room. Seek out conversations with people who think expansively. Read widely. Watch things that challenge your assumptions. Imagination loves company.
Be willing to look a little silly. The reason we stop imagining as adults is often fear…fear of being impractical, of being wrong, of being the only one willing to say something weird. But the most imaginative ideas always sound a little strange at first. Give yourself permission to follow the thought before you judge it.
On that hike, my family and I covered maybe four miles of trail. But imaginatively, we covered light-years. We talked about worlds that don't exist and futures that might. We laughed at absurdities and got unexpectedly philosophical. We connected…and not around logistics or schedules or to-do lists, but around the expansive, joyful act of imagining together.
And when we got back to the car, I had more ideas: for events, for life, for this very Gem… than I'd had all week.
Imagination doesn't require a special location, a big budget, or a lot of time. It just requires the willingness to start with two words: Imagine if.
So here's my challenge to you this week: Start one sentence with "imagine" and see where it takes you. In your next planning session. At your next dinner table. On your next walk.
Because I promise you this: the best events you will ever create, and the most expansive life you will ever live, begin not with a spreadsheet or a strategy deck, but with a simple act of imagination.
You've got this.
XX, Gianna
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Red Bull Showrun San Francisco: This past Saturday, something happened in my backyard that I can't stop sharing with people… and it's the perfect proof of everything I wrote above.
Forty thousand people packed Marina Boulevard as Red Bull transformed one of San Francisco's most serene waterfront stretches into a four-hour wall of engine noise, burnt rubber, and sheer, collective joy. The San Francisco Standard F1 cars ripping down a street where people normally walk their dogs and I normally do my morning jog. Thick tire smoke hanging over the Golden Gate Bridge backdrop. Fans climbing trees and scaling roofs The San Francisco Standard just to catch a glimpse. Free admission. No tickets required. Just pure spectacle.
And here's what struck me most: Yuki Tsunoda, the young Japanese F1 driver behind the wheel, put it perfectly — "Driving an F1 car in San Francisco next to the sea is something that you only imagine. A dream." The San Francisco Standard
Something you only imagine. Yes. Exactly. That's the whole point.
Someone, somewhere, had to first imagine that a quiet Marina street could become a racetrack. That a neighborhood known for brunch and strollers could hold forty thousand screaming fans. That you could give people a world-class motorsport experience for free, on a Saturday afternoon, with the Golden Gate Bridge as your backdrop. The logistics came later. The imagination came first.
This is what I want for all of us, as event creators and as humans. The audacity to imagine something that makes people stop and say: wait, they actually did that? Red Bull didn't ask whether Marina Boulevard was a "realistic" venue. They asked: imagine if it were. And then they built it. That's the whole game. Start with imagination. The rest follows.
Gianna Gaudini is an event strategist, advisor, and author of the Amazon bestselling book "The Art of Event Planning." She's held leadership roles at Google, AWS, SoftBank Vision Fund, and Airtable, creating unforgettable experiences that drive business results. For more insights on creating exceptional events, visit GiannaGaudini.com or connect with her on LinkedIn.
Want to work with Gianna or take her Event Planning Masterclass? Visitgiannagaudini.com/learn-from-me
