Creativity Connects with Mikki Wilson is a Creative Collective podcast that preserves and shares the stories of remarkable women connected to the North Shore community. Hosted by Mikki Wilson, founder of Dot Connector Consulting. Produced by Randyll Collum for Peabody TV. Sponsored by Jenni Stuart Fine Jewelry.
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Jump to:
- 00:00 Welcome, Katie Kimball Dyer
- 01:48 One person: Auntie Norma
- 02:38 One place: London, unmasked
- 05:09 One thing: learning to sail at 14
- 09:03 Leading at 17
- 12:45 The rubber duck prop: Jeep ducking
- 18:04 Blessing bags and a car ready for anything
- 24:26 Katie Stormborn
- 27:18 Head or heart?
- 32:10 The Heart of Finance and where to find Katie
Little Drops of Happiness: Leading with Heart
Katie Kimball Dyer is a financial advisor and business owner, and one of Mikki’s friends. Mikki makes a promise early on: “We’re not going to talk anything about finance.” Instead, the Peabody TV studio couch gets the stories that explain the person: a nanny who became family, a study abroad without a mask, a teenage sailing instructor making weather calls, and a car full of rubber ducks. What comes through is a woman leading with heart, and doing the preparation that lets her keep doing it.
One person, one place: Auntie Norma and an unmasked London
Mikki’s opening question asks for one person, one place, and one thing. For the person, Katie picks Auntie Norma, who was hired to look after Katie as a child and, when the nannying was done, stayed. “We just kept her.”
The place is London. Katie went on a study abroad by herself, no friend in tow, and made herself a promise: she would not change her personality based on who she was talking to. She calls it, with the language she has now, not masking.
“Not only did I make quite a few lifelong friends, but nobody rejected outright the unmasked version of myself.”
Coming home was a rough landing, she says, back to a world where she had been masking the whole time. She was glad she did it anyway. Mikki names what made it work: giving yourself permission.
Mikki Wilson and Katie Kimball Dyer on the Season 2 set. Photo by Randyll Collum for Creative Collective
Learning to sail, and teaching it the same summer
The thing is sailing. Katie credits the Girl Scouts first: “As the weird kid in school, Girl Scouts gave me a place to land.” A two-week camp taught her to sail a Sunfish, which she describes as basically a surfboard with a sail. She came home at 14, too young for a lifeguard certification, and walked into her local town-funded sailing program to ask about a counselor-in-training spot.
“They’re like, oh, two of our instructors just quit. You’re hired. Perfect timing. I had just learned to sail.”
The yacht club, she explains, was the second floor of what she describes as America’s oldest working fish house, and the sailing school was the attic: old benches and a whiteboard. She stood at the back of the chalk talks learning alongside the kids she was about to teach, and she kept the job every summer until her first job after college.
Seventeen and in charge
When the program launched adult sailing, Katie was the only instructor who volunteered. By 17 or 18 she was running it from the powerboat, with a small fleet and adults who did not always like her calls on the weather.
“And I, a 17-year-old, had to stand up for the choice I made.”
She learned how to hold steady while everyone else panicked, even with tornado clouds rolling in over a fleet of nine-year-olds. “Inside I’m screaming, but I’m like, guys, I got this.” Mikki hears the through-line: “You can teach aspects of leadership in a book, but I think leadership comes through lived experience.” It is the same thread she pulled with her last guest, Creative Collective’s Ainsley Keating. And it changed how Katie treats the people coming up behind her: “I was just as capable as I am now, just with less knowledge. So now I am more likely to trust a younger person out of the gate.” Or, more briefly, “Younger doesn’t mean they don’t know.”
Little drops of happiness
Mikki’s guest prop gives the game away, because the rubber ducks are already scattered around the studio. After a concert in Boston, Mikki spotted a container of them in Katie’s back seat. The explanation is Jeep ducking: if you see a Jeep someone has clearly loved, you leave a duck on the door handle. Katie no longer drives a Jeep, but she ducks them anyway, and has tossed a few through open windows in traffic without losing one to the street.
“Little presents to leave for strangers. Little drops of happiness to drop around the world.”
Not everyone knows what to do with it. One driver left the duck on his car and drove off. “It is hard to accept kindness sometimes,” Mikki says. Katie’s answer is simple: “No, I’m just trying to do something nice for you.”
Seeing the person
Katie does not carry cash (her household even owns the cashless Monopoly), and for a long time that left her with nothing to offer when someone asked for help at an intersection. Rolling down the window empty-handed felt rude; ignoring the person felt worse. So she started keeping blessing bags in the car: socks always, sunscreen and hats in summer, gloves in winter, nonperishable food, a separate version for women, a list of local resources, and a note.
Mikki Wilson and Katie Kimball Dyer after taping Season 2, Episode 3 at Peabody TV. Photo by Randyll Collum for Creative Collective
“I see you, this is a hard time in your life, but you’re still awesome.”
The bag is not the point. “The most important part of the whole thing is the interaction: not ignoring the person, and seeing them.” The car also carries snow treads, a collapsible shovel, a pop-up tent, and a jump starter. Mikki reads it as character: “your level of detail and preparedness and care tells me so much about you.” Katie traces it back to kindergarten fire-safety lessons and a trash bag hidden in her stuffed animals, just in case. “It’s always been a part of who I am.”
Way more heart
Her Instagram handle, Katie Stormborn, is a Game of Thrones reference to a character born in a storm. “It kind of is part of her personality, that she can handle the storm because she was born in it.” Mikki suggests it describes Katie too; Katie had not noticed until Mikki said so.
Then the lightning round: head or heart? “Way more heart.” Leading with heart, she says, still needs a check-in. “I lead with my heart, and then sometimes I have to take a beat, pun intended, and let my brain catch up a little bit.” She has learned to ask whether a pull is meaningful or just the next shiny thing. Mikki, a self-described Capricorn who lives in her head, lands on the episode’s thesis: “We need more heart-centered leaders, heart-centered businesses.”
What makes Katie feel most like herself? “Hanging out with my wife,” she says, the person who helps her find her own instincts again when the noise gets loud. Their first trip together was to London. “She’s my feet on the ground.”
Mikki Wilson and Katie Kimball Dyer at Peabody TV. Photo by Randyll Collum for Creative Collective
Lessons We’re Carrying Forward
- The unmasked version of you is usually the one people were hoping to meet.
- Capability does not wait for age; trust the younger person in the room.
- Small, unexpected kindness travels further than we think.
- Leading with heart works best with a moment for the brain to catch up.
Call to Action
Katie’s rubber ducks cost almost nothing, and a blessing bag is a gallon-sized bag and a note, yet both start with the same decision: to see the person in front of you. Leading with heart is not a personality type so much as a habit of noticing, and it is one we can all practice this week, at an intersection, in a parking lot, or in a meeting where the youngest person has an idea. Find more of these conversations at Creative Collective, come to a Creative Collective gathering, or, if you are not a member yet, learn about membership.
Subscribe to Creativity Connects on Spotify
Join the Conversation
- When have you let people meet the unmasked version of you, and what happened?
- Who trusted you with something big before you felt ready?
- What is your version of a little drop of happiness?
Join the conversation at creativecollectivema.com.
Connect with Katie Kimball Dyer
- The Heart of Finance (Katie’s podcast): heartoffinance.com
- Instagram: @katiestormborn
- LinkedIn: Katie Kimball Dyer
Connect with Creative Collective
- Website: creativecollectivema.com
- Membership: creativecollectivema.com/join
- Instagram: @creativecollectivema · @creativecollectiveexplores
- Facebook: Creative Collective
- TikTok: @creativecollectivema
- LinkedIn: Creative Collective
Mentioned in this episode
- Girl Scouts, “a place to land”: girlscouts.org
- The Heart of Finance, Katie’s podcast, where Mikki has been a guest: heartoffinance.com
- Mikki’s previous guest, Ainsley Keating: A Woman Becoming
- Peabody TV, where the episode was recorded
- Jeep ducking and Game of Thrones (no links needed)
Credits
Creativity Connects with Mikki Wilson is a Creative Collective podcast hosted by Mikki Wilson. Randyll Collum produces this podcast for Peabody TV, your community media center serving the residents and businesses of Peabody and the North Shore area. Sponsored by Jenni Stuart Fine Jewelry.
Episode Description
Mikki is joined by her friend Katie Kimball Dyer, a financial advisor and business owner who also hosts her own podcast, The Heart of Finance. Mikki sets the work aside from the first minute: this conversation is about the stories, experiences, and quirks that shaped who Katie is and how she moves through the world.
Katie talks about Auntie Norma, the childhood nanny her family “just kept”; a solo study abroad in London, where she promised herself she would not mask and found that people liked the unmasked Katie; and a two-week Girl Scout sailing camp at 14 that turned into a job as a sailing instructor the week she got home. By 17 she was directing an adult sailing program and making weather calls the grown-ups did not always agree with, lessons in trusting her own instincts that now make her quicker to trust younger people.
Then Mikki’s guest prop comes out: a rubber duck. Katie explains Jeep ducking and the “little drops of happiness” she leaves for strangers, the blessing bags she keeps in her car for people she meets at intersections, and why seeing the person matters more than anything in the bag. They also cover the Game of Thrones story behind her Instagram handle, whether she is more head or heart (“Way more heart”), and the person who keeps her feet on the ground.
Key Topics Discussed
- Auntie Norma, the childhood nanny who became family
- A solo study abroad in London and the decision not to mask
- Girl Scouts as “a place to land,” and learning to sail on Sunfish boats at 14
- Hired as a sailing instructor the week she learned, and directing an adult program at 17
- Trusting your instincts under pressure, and why she trusts younger people “out of the gate”
- Jeep ducking and little drops of happiness for strangers
- Blessing bags, and why the interaction is the most important part
- The Game of Thrones story behind “Katie Stormborn”
- Head or heart, and the people who keep your feet on the ground
Memorable Quotes
- “It was actually that decision to not mask myself, and learn that people actually liked the unmasked version of Katie.” — Katie
- “And I, a 17-year-old, had to stand up for the choice I made.” — Katie
- “Little presents to leave for strangers. Little drops of happiness to drop around the world.” — Katie
- “The most important part of the whole thing is the interaction: not ignoring the person, and seeing them.” — Katie
- “I lead with my heart, and then sometimes I have to take a beat, pun intended, and let my brain catch up a little bit.” — Katie
About the Guest
Katie Kimball Dyer is a financial advisor and business owner at Gateway Financial Partners and the host of The Heart of Finance podcast, where Mikki has been a guest. A Girl Scout who started teaching sailing at 14 and went on to direct an adult sailing program, Katie brings the same instinct for preparation and care to the rest of her life, from the blessing bags in her car to the rubber ducks she leaves for strangers.
Disclaimer: This episode is a personal conversation shared for general information and entertainment. It is not financial, investment, tax, or legal advice, and nothing in it is an endorsement or recommendation of any financial professional, firm, or service by Creative Collective, Mikki Wilson, or Peabody TV.
About the Host
Mikki Wilson is the host of Creativity Connects with Mikki Wilson and the founder of Dot Connector Consulting. Known as “The Dot Connector,” Mikki brings people, ideas, and communities together through trust‑based connection and human‑centered leadership, cultivating conversations that go beyond the brand to highlight the lived experiences and “messy middles” behind women’s journeys.
About the Podcast
Creativity Connects with Mikki Wilson is a Creative Collective podcast that preserves and shares the stories of remarkable women connected to the North Shore community. Hosted by Mikki Wilson, founder of Dot Connector Consulting. Produced by Randyll Collum for Peabody TV. Sponsored by Jenni Stuart Fine Jewelry.
