Connected Hearts in Carlsbad: Creating Deep Friendships in Midlife with Cheryl Dillon

Bret:
Welcome to Carlsbad: People, Purpose and Impact—an essential podcast for those who live, work, visit, and play in Carlsbad. Good afternoon, everyone. I’m Bret Schanzenbach, President and CEO of the Carlsbad Chamber of Commerce, and your host. I’m pleased to have with me Cheryl Dillon, founder and CEO of Fundable Experiences. Good afternoon, Cheryl.
Cheryl:
Good afternoon, Bret. Thanks for having me.
Bret:
As I was preparing for our time together, I noticed you were originally an East Coast gal. New Jersey, right? And you made your way out here—Chicago, then Southern California. Walk us through that journey.
Cheryl:
Yes—New Jersey through and through. All the stereotypes are probably me: fast-talking, direct, and driving fast. I lived in Chicago for five years, and fortunately it was when the Cubs won the World Series. My husband and I lived right in Wrigleyville, so it was magical. I’m a Cubs fan through and through.
We moved here almost eight years ago. In high school I had this vision that I always wanted to live in San Diego. I’d never been here before—I don’t know where it came from—but I imagined the weather, and it absolutely delivered. I waited until I was about 49 or 50 and finally made that intention come true.
Bret:
So you’re living the dream now.
Cheryl:
I love it here. I’ll never go anywhere else.
Bret:
You earned your psychology degree at the University of Connecticut. After that, what was your first chapter professionally?
Cheryl:
When I first got out of college, we were in a recession. My mom said, “Just get any job.” I had taught aerobics in high school and worked at Jenny Craig as a weight loss counselor. I also had a camp counselor background.
My first “real” job was at Johnson & Johnson—back then the title was “secretary,” not admin assistant. I was the secretary to the secretary to a vice president of IT. I was also teaching in the corporate fitness center.
It was a great experience because even temps were treated like employees. We could attend workshops and seminars, and they invested in us. That’s where I learned computers—WordPerfect for DOS, then Windows. I even taught people how to use a mouse.
From there, I began teaching computer skills, which segued into sales for IT training classes. Then I got into IT recruiting. This was mid-to-late 90s—Y2K was approaching, and demand for IT consultants was huge.
Looking back, you can connect the dots. Those early experiences really mattered.
Bret:
Then it sounds like you realized you weren’t corporate employee material.
Cheryl:
Exactly. I lived in New Jersey where big pharma was everywhere. Pharmaceutical companies started hiring recruiters directly as 1099 contractors to sit “in-house.” I created my own company—Job Opportunities—and did executive recruiting contracts at major pharma companies. That was the beginning of my self-employed path.
Bret:
And then you and your husband took a big pivot into a totally different business.
Cheryl:
Yes—my husband Joe has a finance and negotiation background, very complementary to my sales, marketing, and HR experience. We had the makings of our own business.
A colleague’s father owned a children’s cooking school franchise called Young Chefs Academy. We checked it out and ended up buying three licenses. We left Johnson & Johnson and started a cooking school for kids—teaching cooking and baking, running birthday parties, hiring high school students. It was our second business and the first time we worked together as a couple.
Bret:
And then the financial crisis changed the picture.
Cheryl:
Right around 2007–2008, gas and food prices rose. Food was our core cost. There was a ceiling on what we could charge for parties and classes, and it became harder to make the numbers work. We made the hard decision to sell. It was painful because we had so many dreams wrapped up in it.
I went back into my network and returned to HR/recruiting to pay the bills. Joe had a harder time figuring out his next step. It was a grieving process.
Bret:
That led into mediation and divorce work.
Cheryl:
Joe talked to a friend of my mom who was a mediator for police unions. He found it fascinating—it used his negotiation and analysis skills. His parents divorced when he was a kid and it was really ugly. And I’m divorced and remarried; I used mediation myself. Everything aligned.
Joe did a 40-hour mediation program and we opened Equitable Mediation in 2008. At first I was still corporate, but I wanted out. I learned about coaching, went to coaching school, and specialized in divorce. People told me to pick a niche, because if you’re everything to everybody, you’re nothing to nobody.
One day I left my contract, joined Joe, and we’ve been working together ever since—going into year 18 now.
Bret:
It’s meaningful work—but emotionally heavy.
Cheryl:
Very. We help people divorce without lawyers, but it’s still painful. You’re helping them through one of life’s most significant events besides the death of a spouse. It’s gratifying to support them with resilience and compassion, and help them protect their children and finances.
But lately I’ve felt a pull toward more joy. I’m in midlife, the news is heavy, and I miss face-to-face connection. I’m old school—I want meaningful, in-person friendships and experiences.
Bret:
And that’s where Wonderful Experiences comes in.
Cheryl:
Yes. We were reading an article about how midlife and older Americans are shifting from status and things to meaningful experiences. That phrase stuck with me.
I was doing a jigsaw puzzle one day and thought: “Wonderful Experiences.” I had the name before I had the company.
I realized I’m good at throwing parties and connecting people—bringing them together, finding shared interests, helping them leave as friends. I went back to school at SDSU for event planning and got a certificate last year.
Wonderful Experiences has been around for about a year. The core offering is called Connected Hearts—a membership community for women in their 50s and 60s, North County and Carlsbad-based.
It’s a blend of personal growth conversations that go deeper than surface-level, plus fun and whimsy. It’s the community I always wished I had but couldn’t find—so I built it.
The most gratifying part is that women are coming. We’ve had gatherings, guests, and many are joining.
Bret:
On your website, one phrase stood out: a midlife that feels purposeful and connected. What does that mean to you?
Cheryl:
Connected is connecting to others—but it starts with connecting to yourself.
My husband has different friends for different parts of his life. I’m the opposite—I want friendships with depth, where you can laugh, have real conversations, and truly show up for each other.
I realized I wasn’t attracting that because I wasn’t connected to myself. I had low self-esteem. I attracted people who mirrored how I treated myself.
I did a lot of reflection and intentional work to cultivate a better relationship with myself—how I talk to myself, treat myself, think about myself. When you’re connected to yourself, you can connect more beautifully with others. That’s what we cultivate in the group.
Bret:
You also have the Uplift Newsletter. Tell us about that.
Cheryl:
When I started, I needed a way for people to learn who I am. I’m not a celebrity and I haven’t been in Carlsbad my whole life. So I started a free newsletter as a low-pressure way for people to see if they resonate.
I’m around 30 weeks in now. I share personal, vulnerable stories about midlife—things many women think about but don’t say out loud. I normalize it, share how I’m working through it, and offer a reflection question for readers.
It’s meant to inspire and help women connect with themselves, and if they’re local, encourage them to come to a gathering.
Bret:
If someone wants to try Connected Hearts, can they test-drive it?
Cheryl:
Yes. I require women to attend first on a one-time guest pass. I don’t want someone joining and then realizing it’s not for them, because we go deeper than some people are comfortable with.
We have community guidelines and confidentiality. Nobody has to share anything they don’t want to, but it is a safe space.
We gather three times a month:
• A signature in-person gathering once a month for two hours on a Tuesday night (personal growth, meaningful conversation, games, gratitude).
• A virtual connection call once a month to celebrate wins and support each other.
• A casual “just for fun” meetup once a month (coffee, beach walk, etc.) for friendship-building.
Bret:
Are you still doing divorce coaching as well?
Cheryl:
Yes. I’m still co-owner of Equitable Mediation and still coach clients who want emotional support during the process and tips for co-parenting. I’ve automated a lot of our back-end systems, which frees up time, and Joe is incredibly supportive of my new endeavor.
Bret:
If someone wants to learn more, what should they do?
Cheryl:
Start with the website. There’s a button at the top right: “Get the Uplift” to subscribe to the free Thursday newsletter. There’s also a Membership tab for Connected Hearts and the guest pass information. I also offer some private coaching.
Bret:
And outside of work—what do you and Joe enjoy?
Cheryl:
Joe decided to become a sommelier—wine is his hobby. I love to sing and take lessons at Moonlight Studios in Vista. I love gardening and fruit trees—citrus, peaches, figs—and growing food year-round.
And we love hanging out with our rescue dog, Wrigley, from Rancho Coastal. We don’t have human kids—just fur kids.
Bret:
Thank you for sharing your story and for building this community in Carlsbad. And you teased something interesting—there might be a men’s version coming?
Cheryl:
Yes, I’ve had inquiries. We’ll see—maybe that’s the next expansion.
Bret:
Thanks for joining us today on Carlsbad: People, Purpose and Impact. If you got value out of this episode, hit follow on your favorite podcast app and tell a friend. See you next time.