We caught up with the brilliant and insightful Jessie May Wolfe a few weeks ago and have shared our conversation below.

Jessie May, appreciate you joining us today. Getting that first client is always an exciting milestone. Can you talk to us about how you got your first customer who wasn’t a friend, family, or acquaintance?

When I left the fashion industry and began stepping into coaching, I had one big fear: charging for something that felt so natural to me.

I’ve always been someone who connects easily with people—on planes, in grocery lines, walking my dog, my uber drivers. Deep conversations have never felt like work.

On a flight from Montreal to Los Angeles, I found myself seated beside a lovely man who gradually began sharing about his life. Over the course of the flight, we talked for hours. I listened, reflected, and offered insights that seemed to deeply resonate with him. I could tell our conversation was moving something important.

At the time, I was making the transition from fashion into coaching, and although I believed in the work, I still felt tremendous hesitation around asking people to pay for it. But I also knew that if I truly wanted to build a new career, I had to be willing to take the leap.

So, before we landed, I gathered my courage and simply said, “If you’d ever like to continue the conversation, I’d be happy to do a coaching session together.”

To my surprise, he immediately said, “I’d love to.”

That became my first paying client.

More importantly, it taught me something that has guided my business ever since: when something comes naturally, we often underestimate its value. What feels effortless to us can be deeply meaningful to someone else.

Nearly everything I’ve built since—from one-on-one coaching to group programs, corporate work, and speaking engagements—has grown in the same way: through authentic conversations, referrals, and a willingness to offer support where I genuinely felt I could make a difference.

Looking back, that chance encounter somewhere between Montreal and Los Angeles wasn’t just where I found my first client. It was where I learned to trust the value of what I had to offer.

Jessie May, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

I’m Jessie May Wolfe, founder of the HeartRise Method, speaker, coach, and host of the Sunny Side Up podcast. But long before any of those titles, I was simply someone captivated by people, stories, creativity, and what helps us come alive.

I studied Communications with a minor in Documentary Film Studies, drawn to understanding the human experience and the power of storytelling. From there, my creative path led me into photography, graphic design, and eventually fashion, where I spent six years building a clothing line sold in more than 400 stores across North America.

Whether behind a camera, creating a collection, or sitting in deep conversation, I’ve always been fascinated by identity, expression, and what makes each of us uniquely who we are.

That curiosity eventually led me into the worlds of human potential, personal growth, healing, and transformation. Over the past two decades, through years of study, practice, and the privilege of working with thousands of individuals, I’ve remained endlessly fascinated by the meeting place between science and spirit, heart and mind, healing and becoming.

Over time, that exploration gave rise to the HeartRise Method—a practice devoted to cultivating emotional intelligence, heart wisdom, and helping people reconnect with themselves and one another from the inside out.

Looking back, I can see that while the forms have changed, the heartbeat has always remained the same. Over the years, the creative, personal, and transformational threads have woven together, shaping the work I now have the privilege of sharing through HeartRise, Radiance Coaching, speaking, podcasting, and community.

Today, I support entrepreneurs, leaders, creatives, and changemakers in navigating life’s transitions, deepening self-awareness, strengthening relationships, and bringing what I call their Signature Power to life—the unique way each of us is meant to love, lead, create, and contribute.

At the heart of everything I do is a simple belief: we all carry a signature song within us.

And the world doesn’t need more perfection or performance.

It needs more people who feel safe enough to trust themselves, honor their gifts, and be fully self-expressed in their own unique way.

I believe we’re longing for places and spaces where we can come home to ourselves, connect more deeply with one another, and remember that we belong.

Creating those spaces—and gathering around what matters most—has become both my deepest joy and life’s dedication.

Because when we have the courage to live the fullness of who we are, we give others permission to do the same.

And one heart on fire has the power to ignite every heart it touches.

Have you ever had to pivot?

People often describe major life and business changes as pivots, but looking back, I see them more as evolutions.

One of the biggest shifts in my own life was moving from the fashion industry into the world of human potential, personal growth, and transformation. At the time, I had spent six years building a clothing line that was sold in more than 400 stores across North America, and from the outside, it looked like I had built something successful.

But inwardly, I felt a growing call toward something deeper.

What I came to realize was that I wasn’t leaving one passion behind for another. The forms were changing, but the heartbeat remained the same. Whether through storytelling, photography, fashion, or eventually coaching and speaking, I had always been fascinated by identity, expression, and what helps people come alive.

Making that transition wasn’t without uncertainty. There were moments when I questioned myself, wondered if I was qualified enough, and wrestled with the vulnerability that comes with beginning again. But I’ve learned that growth often asks us to trust what is quietly calling us, even before we can fully see where it will lead.

Over the past two decades, that curiosity led me into the worlds of healing, emotional intelligence, heart wisdom, and human potential. It ultimately gave rise to the HeartRise Method and the work I now have the privilege of sharing through coaching, speaking, podcasting, and community.

If that experience taught me anything, it’s that sometimes what looks like a pivot is really an invitation to more fully embody who we’ve always been.

The forms may change.

But the heartbeat remains the same.

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?

One of the biggest lessons I’ve had to unlearn is the belief that life unfolds according to a fixed timeline.

For many years, I unconsciously carried the idea that there was a right pace, a right order, and a certain set of milestones I was supposed to achieve by a certain age or stage of life. Like many people, I absorbed cultural expectations around success, productivity, and what it means to be “on track.”

Over time, I’ve come to see that life has its own intelligence.

The ancient Greeks distinguished between Chronos, chronological time, and Kairos, what they understood as sacred or unfolding time. That distinction has profoundly shaped the way I live and work.

I’ve learned that growth can’t be rushed. Healing can’t be forced. And some of the most meaningful chapters of our lives arrive in their own season.

Ironically, many of the things I’m most grateful for today didn’t happen according to my plans or my timeline. They emerged when I learned to soften, trust more deeply, and make peace with the unfolding.

If I’ve had to unlearn anything, it’s the idea that we’re behind.

I don’t believe that anymore.

I believe we each have our own rhythm, our own path, and our own unique timing.

And I’ve found that the more we trust that, the more life has a way of revealing exactly what we’re meant to meet next.

Contact Info:

• Website: jessiemay.com Heartrisemovement.com
• Instagram: @jessiemaywolfe @heartrisemovement

Image Credits

Jess Linderman
Laura Grier