Risking delight in dark times (The Wonder Dispatch)
Part 2: The power of Wonder Gestures in business, leadership, & life
Good morning,
In dark times, the last thing many people think of is gifting delight and wonder. And yet that just might be what we need more of.
These days I keep returning to Jack Glibert’s poem “A Brief for the Defense”:
“Sorrow everywhere. Slaughter everywhere.…
…There is laughter
every day in the terrible streets of Calcutta,
and the women laugh in the cages of Bombay.
If we deny our happiness, resist our satisfaction,
we lessen the importance of their deprivation.
We must risk delight.”
I must take a deep breath each time I read these lines and wonder.
How must I risk delight? And how could I risk delight with people I care about and work with?
What about you?
Leaders & directors: How can you risk delight for your team or direct reports?
Entrepreneurs and owners: How can you risk delight for your
Writers & creatives: How can you risk delight for your readers and audience?
Parents: How can you risk delight for your troubled teen?
In the previous Wonder Dispatch, we explored an overlooked skill that could 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.
In this week’s Wonder Dispatch
Main Message: In this Wonder Dispatch, we explore the final three of six types of Wonder Gestures that ripple delight through relationships and culture:
C.R.E.A.T.E. — Curiosity, Recognition, Emotional Peak, Afterglow, Transcendent, and Expansion.
Destination Delight
During the pandemic, many of us heard about the toll it took on many teenagers’ mental health. I often wonder what I would have tried if one of my daughters spiraled into a dark place.
I want to tell you a story of two parents I admire who did risk delight.
Hollye Dexter, a mom to three and a creative writer in Los Angeles, noticed her 14-year-old son slipping into depression during lockdown. They were supposed to have spent spring break in New York City, seeing Broadway shows and indulging in the big city’s delights. But just because they were stuck at home didn’t mean they had to completely miss out on New York.
Hollye and Troy decided to make a destination dinner for their son. “Don’t come out of your room until dinner,” they told him. They transformed their living space into a version of Times Square, using upcycled carboard and basement supplies to make skyscrapers and landmarks. They made a playlist of New York tunes. They ordered Domino’s Pizza but then changed the box with the label of a famous Manhattan pizzeria.
When their son emerged, his sullen face lit up. He couldn’t believe what his parents had done.
Hollye said his true self returned. They relished feeling as if they were transported to their destination for the whole evening. They sang, played games, and delighted in the wonder of an evening away. At the end of the night, her son said, “OK, where are we going tomorrow night?”
That question launched ta family ritual: over forty destination dinners from Tokyo to outer space. “I spent hours crafting a didgeridoo for our Australia night,” Hollye said, “and I knew it would only be used for this one occasion, but it gave me so much joy to throw myself into this project, it was like therapy for me. I don’t know how we would have gotten through the quarantine without our destination dinners.”
What began as one act of wonder turned into a tradition that nourished everyone’s spirit. Wonder, when given freely, has a way of feeding everyone involved.
And here’s the thing: You don’t need elaborate props to risk delight for your hero-clients, team, or loved ones. Sometimes the most important gifts we give emerge from everyday materials, born of empathy and a desire to elevate by meaningful surprise.
In the previous Wonder Dispatch, we unpacked Curiosity, Recognition, and Emotional Peak Experiences and Gesture. Let’s unpack the other three.
Afterglow
Every August, my family retreats to a remote Maine island for seven unplugged days of biking, swimming, and simply being together. Each evening, we walk to Sunset Bay to watch the sun melt into the horizon.
One night, the sunset caught fire in a pulsing orange that drenched the sky. But here’s what struck me: Most people walked away too soon like leaving before the credits roll. Funny thing, they missed the astonishing awe
How many times have you rushed to the next thing not to allow for a moment to really settle into your cells?
With almost every passing ten seconds, as the sun vanished from sight, the sunset’s afterglow continued to transform the clouds and sky into something no master painter could capture. My camera couldn’t even capture the experience, but I tried.
That sunset’s afterglow lingered with me for days. A month later, as we all resumed work and school schedules, I created a slide show of our island experience, including shots of that emergent sunset after glow. The slide show - cast with Max Richter music - was my way to extend the emotional experience for all of us.
Afterglow Experiences deepen a meaningful memory after the experience has passed. At the close of our events, we’ve done things like dash to a building roof in SoHo, New York. to huddle in the rain and howl.
»> What small ritual, gift, or reflection could you create to let someone relive a peak moment you shared?
»> You might create a simple ceremony or ritual to make an experience’s wonder linger - whether it’s a retreat or the close of a client engagement.
You can make a simple memento of a wondrous moment you had with a client and send it to them. After a meaningful experience with other people, ask each person or participant to pause and reflect on one personal sensory highlight from the experience.
Transcendent
Transcendent Experiences of full immersion & flow let us be at our genius best and allow us to move beyond our perceived limitations. A father in California I know builds backyard obstacle courses for his daughters not just to entertain them, but to help them feel courageous.
»> How might you help someone face a fear and develop a strength?
»> How could you invite someone to move beyond their comfort zone into a brave zone?
Expansion
Expansion Experiences help us feel bonded and connected to something, someone, or to a group beyond our self and our self-limitations. They can fulfill the core human need to belong and feel connected to a greater purpose.
Since 2018, I’ve studied ways to foster belonging in our retreats and MasterMinds. I’ve looked deeply into The Belonging Gap, and here’s what works:
» You could create experiments that require people to collaborate and create something together.
»> Provide moments for people to show that they understand and care about one another.
»> Facilitate moments of shared values, dreams, and vision.
C.R.E.A.T.E. Wonder with Rippling Effects
When you weave all six Wonder Gestures together—Curiosity, Recognition, Emotional Peak, Afterglow, Transcendence, Expansion—you get a powerful acronym: C.R.E.A.T.E.
You really don’t know how a gift of wonder will ripple.
When 11-year-old Amy Sherald visited a museum in Georgia, she didn’t expect to be given a gift that would last a lifetime, but that is how she describes it. The artist told a New York Times reporter that at that museum she saw the black painter Bo Bartlett’s self-portrait “Object Permanence.”
For the first time she says she “experienced the power of seeing a painting of a person who looked like me. It was the first time she’d seen a painting of someone who looked like her. That moment stayed with her for life.
She said, “I essentially built my career around that moment.”
“I want to explore,” she says, “the wonder of what it is to be a black American. And the complexity of that identity. I want the everydayness of the people to psychologically stay with you and change how you interact with others.”
Sherald says she wants her work to be “a gift” to the black public because of the moment that seeing Bartlett’s painting gifted her.
Sherald’s wish came true. Years later, Sherald was chosen to paint Michelle Obama’s official portrait. When a two-year-old Black girl named Parker Curry saw that portrait at the National Gallery, she stood still in silent awe. Her body froze. She refused to look away.
One witness said, “She had this wonder that was silent and yet seemed to be saying something very big at the same time.”
That’s how wonder ripples.
No matter how simple or elaborate, when you spark delight for someone else, you just might alter the way they see themselves—and the world.
And that, I believe, is among the most powerful gesture of love.
Your Turn to Wonder
» What’s one gesture you could offer this week that might bring a little light or surprise to someone else’s life?
Share your response with me by commenting in the Substack Wonder HUB box among other members, replying to this Dispatch email, or tagging me on social. I’d love to hear what you come up with.
Have questions or observations about this Wonder Dispatch? Suggestions for topics you’d like me to take up?
I appreciate your showing up here for the work that matters in this one beautiful life. It’s an honor to quest with you. I’ll see you soon.
Be well, and thanks for running with me,
Jeffrey
Coming Up at The Wonder HUB
The next Wonder Dispatch: The intelligence of not-knowing and tracking insights
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“Exquisitely curated” sounds like someone designed for delight, wonder, and connection. I’m so glad you let yourself be delighted. I used to live there.
I recently attended an exquisitely curated and beautifully presented event in Woodstock, NY, and it was so restorative. I hadn’t done anything to nourish my spirit like that in a long time. Not too far from you, I imagine!