Hey, I’m Sheila.

I’m a storyteller who believes love and laughter are the best strategy of all. I’m also a mom of three, a wife, a creative, and a strategist—most days doing small-church work that somehow requires big vision, a calm nervous system, and a sense of humor.

For over a decade, my husband and I lived in the long shadow of infertility. It was brutal—on our marriage, on my mental health, on our hope. But somehow, we made it through. We adopted two incredible children through domestic infant adoption, and—after years of appointments, procedures, and prayers—we welcomed a biological child through IVF. That journey shaped every corner of my life. It forced me to grieve what I couldn’t control, and it grew my capacity for empathy, honesty, and humor in the middle of hard things.

Somehow, in the mix of it all, I’ve become a comedian.

Not because my life is easy—because it isn’t. Because my life is a stage. And I belong on a stage where I can bring what’s real to the surface. When I’m onstage (or behind a mic), I’m not just chasing laughs. I’m guiding emotion to the forefront—laughter, sadness, anger, fear, tenderness, hope. All of it. Comedy is the doorway. The point is connection. The point is relief. The point is remembering we’re human—together.

My personal mission is to be light and laughter in people’s lives, and to bring our emotions back into the room. My presence is rooted in authenticity—what you see is what you get—and if you want a life that feels more awake, more honest, and more human… I’m here to bring you along for the ride.

Out of this work came Raising Grace, a podcast I created during one of the wildest times in modern parenting—pandemic years, political polarization, and digital overload. For one full year, I interviewed 25+ parents with real stories: divorced, married, stay-at-home, career-driven, city dwellers and small-town survivors. We talked about raising kids in chaos with compassion, intention, and (hopefully) a little grace. That podcast was a lifeline—for me and, I hope, for others. I still carry those lessons into my own parenting every day. I mess up constantly. I apologize a lot. I worry I’m screwing it all up. But I keep showing up—with love, humility, and a healthy sense of humor.

These days, I work at a progressive Presbyterian church where I lead music, build community, and create worship experiences that stretch across generations and denominations. I’m currently co-authoring a book with my spiritual mentor called The Roots of Heaven, a deep and beautiful story about faith, healing, and spiritual wholeness.

I’m also growing a new worshiping community called Good Company, designed for spiritually curious professionals who want something deeper—without the dogma. Think of it as a place for the soul to breathe, grow, and laugh a little too.

I write about all of it—faith, parenting, work, wholeness, and the absurdity of being alive—on Substack. If you’re looking for some sacred sanity in your inbox, you can follow along there.

I’ve done a lot. I continue to do… a lot. Some might say too much, but I say I’m just getting warmed up. People keep trying to give me titles—singer, speaker, strategist, spiritual coach—but I’m not interested. Titles are for name tags at awkward conferences.

I’m Sheila Chester. A connoisseur of all. A storyteller in every way, shape, and form. If it involves people, purpose, or a good plot twist, I’m probably in the middle of it.