Work with Cheryl

Speaking, Connection Experiences & Media Conversations

Speaker Cheryl Dillon delivers engaging talks and interactive experiences that help audiences rediscover the joy of genuine human connection.

Helping People Rediscover The Joy of Genuine Connection in a Disconnected World

Organizations, communities, and media partners invite Cheryl Dillon to speak, facilitate engaging group experiences, and share insights on friendship, human connection, and navigating life’s transitions.

Speaking

Cheryl’s talks are engaging, interactive, and tailored to each audience, blending storytelling with practical insights participants can apply right away.

Featured Talks:

  • The Power of Genuine Connection

    (Ideal for conferences and general audiences)

  • Beyond the Business Card: How Genuine Connection Strengthens Relationships, Referrals, and Results

    (Ideal for networking groups, chambers of commerce, and business audiences)

  • Belonging Is the Engine: How Genuine Connection Strengthens Membership Communities

    (Ideal for associations, nonprofit organizations, and membership communities)

  • Connection Starts Here: Becoming Your Own Best Friend

    (Ideal for women’s groups, personal development audiences, and wellness communities)

  • The Energy You Bring: What You Focus on Grows

    (Ideal for leadership groups, personal development audiences, and organizations navigating change)

  • The Gift of Going First: How Small Acts of Courage Create Connection

    (Ideal for personal development audiences, women’s groups, and communities focused on friendship and connection)

What Audiences are Saying

Cheryl’s talk on the Power of Genuine Connection was one of the most fun and interactive presentations we’ve had at Rotary. She has a rare ability to speak straight to the heart – her humor, authenticity, and practical wisdom left me with a new perspective on how I show up in my conversations. I’d recommend her to any group looking for a speaker who helps people truly connect while having fun doing it.
Gayle Tweedy, Rotary Club of Carlsbad
I’ll be honest, when Cheryl started leading us through some of the exercises, I wasn’t sure what to expect. It felt a little outside my comfort zone at first. But once we got into it, the value became crystal clear. Two months later, I’m still using what I learned that day in my conversations.

Cheryl has a gift for making practical, meaningful skills genuinely accessible, and even fun. I’d recommend her to any group that wants to walk away with tools they’ll actually use.

Brian Crumbaker, Rotary Club of Carlsbad

Connection Experiences

Many events bring people into the same room, but meaningful interaction rarely happens on its own. Guests often stay with people they already know, exchange a few polite words, and leave without ever interacting with anyone new.

Cheryl designs and facilitates engaging experiences that change that dynamic, helping guests genuinely connect with one another.

The result is a more memorable event – one that keeps guests engaged and leaves a lasting positive impression of the host, organization, or brand behind it.

These experiences work especially well for:

  • Conferences and professional gatherings
  • Networking events
  • Corporate retreats and team gatherings
  • Community gatherings
  • Business or brand launches
  • Member-based organizations
  • Parties, galas, and social events

Podcast Interviews & Conversations

As a speaker on genuine connection and friendship, Cheryl enjoys thoughtful conversations about how we build meaningful relationships – with ourselves and with others – during life’s many transitions.

Her warm, relatable storytelling and practical insights resonate with audiences navigating changing priorities, evolving identities, and the question many midlife women quietly ask themselves, “What’s next?”

Topics often explored include:

  • The power of genuine connection
  • Cultivating real friendship in adulthood
  • Becoming your own best friend
  • Navigating life transitions and identity shifts
  • Living intentionally and redefining what matters in midlife
  • Creating a vibrant, Funderful midlife

Featured Conversations

The Midsters

Cultivating a Joyful, Funderful Life

Reinvention Real Talk

Choosing Yourself in Midlife

Radiantly Rooted with Rachel

The Secret to Deeper Connection in Midlife, Starting with You

Her Comeback

Transforming Your Life After 50

Not Your Mother’s Midlife Crisis

Key Points in the Divorce Process Through Mediation & Coaching With Cheryl Dillon

Carlsbad Chamber of Commerce: People, Purpose and Impact

Coming Soon

Book Cheryl

Connection doesn’t happen by accident – it happens when someone intentionally creates space for it.

If you’re planning a conference, community gathering, or podcast interview and want your audience to leave feeling energized, inspired, and genuinely connected, Cheryl would love to be part of the conversation.