Can you design for delight & wonder? (Wonder Dispatch)
Part 1: the power of Wonder Gestures in business, leadership, & life
Good morning,
Remember the last time someone surprised you not with a grand gesture, but with a small delight that made you pause, laugh, or feel seen?
What if we could design for those moments?
Sometimes I can creatively obsess over giving delight. Something as simple as finding a new way to grill salmon and veggies in a way that my two food-particular daughters will savor around the dinner table. “Wow!” one of them says, “These grilled vegetables are actually really good,” and delight courses through me, too. Or my efforts can be as complex as facilitating experiences of wonder at in-person retreats, keynotes, or even on virtual events.
Not to impress but to connect or awaken. Or both.
Leaders: Do you want to shake up how your team meets or approach 1:1s with a more elevating mood?
Entrepreneurs: Are you hungering fresh ways to surprise and delight your hero-customers?
Makers: You create for joy and for the spark in someone’s eyes when they receive it, right?
Maybe think of it this way: We still live in what some journalists call the experience economy. More and more, people value experiences over products (74% of Americans according to an Expedia study).
Whether you’re a team leader, entrepreneur, teacher, or artist, one overlooked skill might unlock real engagement and loyalty: Your ability to surprise someone with care. That’s what delight really is. Not flash. Not gimmicks. It’s meaningful surprise rooted in empathy, curiosity, and artistry.
This week, let’s unpack how we can intentionally craft these Wonder Gestures - small acts that bring someone unexpected delight, beauty, or self-recognition. They can foster powerful exchanges of delight that ripple through business, relationships, leadership, and creative work.
In this week’s Wonder Dispatch
This month, we’re sharing strategies, tools, and tips that equip you to hone your creative intelligence and wonder-tracking on behalf of your work, leadership, endeavors, and life. This week:
Main Message: the value of gifting wonder to others
What’s on Jeffrey’s and Team TW’s Radar
Popsicle Hotline
Why is the Magic Castle Hotel the second highest-rated hotel in Los Angeles next to the Four Seasons? The Castle can’t boast award-winning restaurants, or an exclusive spa. So what is their secret?
Popsicles. Mounted on the lemon yellow wall beside the Magic Castle’s pool is a bright red phone. When you pick it up, someone answers, “Popsicle hotline!” And in a matter of minutes, a popsicle will magically appear. No luxury spa. No Michelin restaurant. Just a moment. And yet it’s one of the most beloved hotels in the city. That’s not a gimmick. That’s experience design. That’s delight.
Could you create a “popsicle hotline” in your own way? A surprising, small gesture that makes someone feel remembered, elevated, connected?
The Gift of Wonder
Wonder Gestures disrupt default routines, and they restore connections.
In my work with professionals - be they over-taxed executives, hardworking entrepreneurs, or therapists at a crossroads - I’ve found that transformation rarely happens through spreadsheets or goal-driven sprints alone. It comes more through experience. Designed with care.
Not just when they are on the receiving end of my Wonder Gestures but, more, when they muster the mindset to test out the skills of gifting wonder to their own client-heroes or audiences.
Most of us have the biological urge to offer memorable, surprising experiences and insight to those people whom we love, care about, and serve. We don’t need big budgets to design for delight. We need the willingness to surprise someone with care. What matters is that it wakes someone up—even for a moment.
“The art that matters to us—which moves the heart, or revives the soul, or delights the senses, or offers courage for living, however we choose to describe the experience—that work is received by us as a gift is received.”—Lewis Hyde, The Gift
But where to begin? What’s your “popsicle?” I’ve noticed patterns among what kinds of Wonder Gestures land most meaningfully. Here are three of the six kinds.
Curiosity
Design Curiosity Experiences that spark inquisitiveness, surprise, and delightful uncertainty.
One manager in Austin who had attended one of workshops noticed how his team showed up to meetings dimly lit from the inside. As soon as they walked in, they were ready to leave. So he changed just one thing: the meeting location each week. A closed room. A patio. The kitchen space. Suddenly, energy shifted. Conversations sparked. People woke up.
Wonder doesn’t always require reinvention. Sometimes it just asks you to shift the frame.
At one event that we hosted, we distributed random first names to each participant. Names such as “Hansel,” “Juliet,” “Pooh.” Curiosity piqued. Toward the session’s end, we gave participants the prompt to find their fairytale or literary partner in the group, and then gave them a prompt for conversation. People relaxed as they laughed together in shared curiosity.
Recognition
Recognition Experiences offer opportunities for insight, renewal, and discovery in which people see themselves, other people, a concept, or a situation anew.
In our TW Inner Circle MasterMinds, we have ample opportunities to experience Recognition through spotlights. I openly discuss the value of admiration as the Mirror Facet of Wonder. Admiration can feel like a surprising love for someone’s excellence in character or craft. In strategic coaching and advisory sessions, I also aim for clients to experience much-needed self-recognition and self-admiration.
Sometimes, the greatest Wonder Gesture is helping someone admire their own character and actions.
Emotional Peak Experiences
Build Emotional Peak Experiences that allow people to feel deeply and elevated in surprising ways. Some research shows that people most remember the beginning, middle, and end of experiences. Think, Day One on the job. Onboarding a client. Offboarding a client.
If you host large events or conferences, remember that not everyone is a raging extrovert. You can create hubs for sharing stories or experiences for emotional connection. Your event will be that much more meaningful and memorable.
As a creator, innovator, entrepreneur, or business owner, you can create an emotional customer experience. Your brand is your customers’ total emotional experience, at every touchpoint in your business.
For every long-term private client, we gather soft data - their hobbies, interests, and pastimes outside of work. In passing, one client mentioned an abiding passion for hiphop music. For this client, I would discover, hiphop music also recalls an earlier time before raising children when they used to host spontaneous dance parties in their apartment. So, at a pivotal moment in this client’s work, I found the perfect hiphop book by Questlove and mailed it to them. They loved it! And I loved that they loved the surprise.
No matter how simple or complex your efforts, if you can tap into what sparks wonder for others, you can bring more light and life into the world. Connecting with others in wonder is, I believe, one of the most powerful gestures of love.
Your Turn to Wonder: What’s Your Popsicle?
So this week, I invite you to reflect:
»> Where could you offer someone a Wonder Gesture?
A client. A team member. A friend or partner. Your own sense of self.
What small surprise would bring them joy? What would delight you to give?
These moments say: I see you. I thought of you. You matter.
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Curiosities on Jeffrey’s Wonder Radar
Ribs by Lorde (music) - My teen daughter utterly delights me by sharing new music in our car drives. Like this one. “It feels so scary getting old.”
Imaginal Ecology (Brooke Williams | Orion) - I’m hearing the word “enchantment” again in public conversations. Re-enchantment was a topic I broached in grad school in the ‘90s when there weren’t many of us willing to have the conversation. Maybe I need to revisit this.
2x20 (Jonathan Fields | Awake at the wheel | Substack) - My friend Jonathan unpacks how he’s working with his big life transition. There’s a lot of beautiful overlap with what we’ve been exploring with tracking bewilderment and experimentation.
Radical Listening (with Scott Barry Kaufman | Beautiful Minds | Substack) - My friend Scott chats with positive psychology coaching pioneers Robert Biswas-Diener and Christian van Nieuwerburgh. I’ve been reading this book. Another future topic for us to take up?
This coming week at The Wonder HUB
Premium Content for Paid Members: The Wonder of Radical Openness
The Wonder Dispatch: Risking delight in dark times - Part II
Have questions or observations about this Wonder Dispatch? Suggestions for topics you’d like me to take up?
Comment: If you’re reading this Wonder Dispatch via email, you can click on “Comment” to share in The Wonder HUB or hit reply for a private message.
I appreciate your showing up here for the work that matters in this one beautiful life. I’ll see you soon.
Be well, and thanks for running with me,
