Meet Holly Mandel

We’re excited to introduce you to the always interesting and insightful Holly Mandel. We hope you’ll enjoy our conversation with Holly below.

Holly, so great to have you with us and we want to jump right into a really important question. In recent years, it’s become so clear that we’re living through a time where so many folks are lacking self-confidence and self-esteem. So, we’d love to hear about your journey and how you developed your self-confidence and self-esteem.

People would’ve said I was a confident person most of my life, but that wasn’t my experience. It felt more like a façade than something I actually felt in my body. What I’d call real confidence, AUTHENTIC confidence, was something I had to uncover, and develop…or maybe just feel safe enough to finally allow.

I started to notice something deeper taking shape when I began studying and performing improv. At the time, I was working at Walt Disney Studios, my first job after college, and thought I’d found my career path: the fancy studio life, nice expense accounts, surrounded by celebrity, the whole “Hollywood” thing. Then I took a class at The Groundlings in West Hollywood, and something completely shifted. And then, improv wasn’t mainstream like it is now. It was not as well-known. So, I didn’t totally know what I was walking into.

If you’ve never taken an improv class, it’s a very live, interactive, on-your-feet experience. Each game offers something different, and over time, you start to see and think in a whole new way. I learned to listen more deeply, to build on what’s given, and to stop trying to control the outcome. The unknown became more thrilling than scary. The known started to feel flat.

What surprised me most was how much I was changing. I now see this happen with students all the time. To improvise well, you have to use a different GPS: your intuition. Viola Spolin, the mother of improv, said that was the whole point — to strengthen intuition. That was exactly my experience. In improv, there’s no right or wrong, so trying to figure out what you SHOULD do gets you nowhere! You have to go with what you WANT to do, what you FEEL is next. That reconnected me to a part of myself I’d unintentionally cut off.

I had gotten in the habit of questioning everything — what’s pleasing, what’s right, what’s acceptable. That meant I wasn’t asking what I, myself, actually wanted. I grew up in the Midwest. I’m a Gen-X woman. I’m fluent in niceness. Making sure others were comfortable, likable, happy with me…that was the air I breathed. And while I had a strong personality, the confidence was often surface-level. Underneath, I was just trying to fit in and not screw it up.

Improv began to stitch some of that back together and made me look at what I wanted and how I felt. And because it’s rooted in playfulness, I could try on different characters: an uptight landlord, a neurotic travel companion, a giddy co-worker. The masks dropped and I realized how flexible our “self” actually is. It’s not fixed. It’s something we can shape, expand, and reclaim. What started happening in class started happening outside of class too. That’s why I stuck with it. It woke up something real in me.

So when I talk about confidence and self-esteem, this is what I mean. Improv let me try things, say things, do things without judgment. In improv, the rule is “yes, and.” Whatever you contribute becomes fact. You say we’re pirates and we lost our map? That’s the scene! There’s no overthinking, no putting it through the filters of SHOULDS. That gave me a full-body experience of, “This is what I have to say, and I’m not going to worry about how it lands.” It was the opposite of shape-shifting. It was integration.

I once heard someone say the goal of any growth path is wholeness. You show up as the same person wherever you are. That clicked for me. The result of that wholeness, for me, has been real, authentic confidence. There’s a direct line now from what I feel to what I say and do. I speak when I mean it. I do things because I choose to. I trust my gut even if I don’t fully understand why.

True confidence and self-esteem take time. They’re also incredibly personal. Especially for women, these topics touch everything — culture, values, history, identity. So many of us have had to cut off parts of ourselves to survive or succeed. And when you start reconnecting those parts, it’s not always easy. The world rewards us when we play by the rules. But I don’t think real happiness is possible without that reconnection. Self-esteem means knowing your value and walking through the world with it. That’s powerful. And yes, there are forces that would prefer we didn’t. Which is exactly why it’s a — wait for it — bold journey!

Appreciate the insights and wisdom. Before we dig deeper and ask you about the skills that matter and more, maybe you can tell our readers about yourself?

Over the past year, I’ve been in the process of rebranding my company, iMERGENCE, which I founded back in 2011 to bring improvisation to the corporate world. While we’re still focused on leadership development, communication, collaboration, and team dynamics, the bigger shift is this: expanding who we bring improv to and how it can be used. I’m interested in how improv can liberate people — not just make them better presenters or team players, but help them dismantle limiting beliefs, move past fear, and access more creativity, confidence, and presence in their work and lives. It’s improv as transformation, not just performance.

That idea has been at the heart of all the work I do, whether it’s with executives at Fortune 500 companies or artists in the rehearsal room. And it’s led to some exciting new projects. I have a book on improv coming out in the new year that explores these ideas in depth—how the principles of improvisation offer not only a set of tools, but a whole new mindset. I’m also in development on a new kind of improv-based show here in New York, working with some of my favorite improvisers and collaborators. It’s rooted in spontaneity, emotional truth, and the magic of co-creation, and I couldn’t be more excited about it.

A bit about my background: I was a Main Company member at The Groundlings in LA for many years, and I founded the first female-founded improv school in NYC back in 2002. I’ve taught and directed everywhere from corporate boardrooms to college classrooms, and I currently teach at Pace University. I hold degrees in sociology and psychology from UCLA, which probably explains my lifelong obsession with why people do what they do—and how we can do it with more freedom, joy, and awareness.

Across everything I create, teach, and perform, the goal is always the same: to invite people back to themselves: less edited, less afraid, and way more alive.

There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?

Great question. What comes to mind first isn’t really a skill or area of knowledge, but more of a knowing I’ve carried for a long time: that life, at its core, is positive. Every experience — whether it shows up as a challenge, a breakthrough, or something in between — has something to offer. It’s always an invitation to come closer to love. I know that might sound a little out-there to some people, but for me, it’s just true. That perspective helps me loosen my grip on how I think things are supposed to go. It lets me stay curious about what’s actually unfolding, even if it’s not what I planned. When I get too attached or try to control everything, that’s when stress creeps in. But when I step back and let things move, something better usually shows up.

Another thing that’s been essential is humor. It’s saved me more times than I can count. It disarms tension, cuts through the noise, connects people. It can deliver a hard truth in a way that doesn’t make people shut down. It makes space. I’ve always felt that humor lets something land without needing to force it. Someone once said, “Laughter is the shortest distance between two people,” and that feels exactly right to me. Humor gets in where intellect or persuasion sometimes can’t.

And then, following what pulls me. I’ve learned to trust what I’m drawn to, even when I don’t have a solid reason why. If something lights me up or makes me curious, I move toward it. I’m not great with overly rigid plans. I do better when I let action and response show me the next step. I often leap before it’s all mapped out, and figure it out as I go. That’s actually where I do my best work…when I let it be alive and evolving instead of trying to get it perfect first.

If you’re just starting out, I’d say this: get quiet enough to actually hear what’s true for you. Stay open. Be curious. And don’t forget to laugh — especially when things feel messy or uncertain. That’s where the good stuff usually starts.

Is there a particular challenge you are currently facing?

The biggest challenge I’m working on right now is growing my company from a solo-led business into something that can scale and sustain itself with more clarity and ease. For a long time, I wore every hat as every solo-preneaur can relate to — visionary, web designer, facilitator, admin, bookkeeper, you name it. That got me far, but not where I want to go next. And it can burn you out as it was starting to do to me.

I’ve been learning and applying the EOS framework (Entrepreneurial Operating System), which has been really helpful! It’s given me the framework to go to the next level. To grow, I have been learning that the internal structures and systems need to be FIRST, then the external can grow. That felt counter-intuative to me. Now I see how vital it is to pull back and look at the whole picture — what needs to be systemized, what’s worth holding onto, what needs to wait…and as a creative person (Manifesting Generator for all my Human Design people out there!)…I NEVER have an issue creating “one more fun idea!” It’s helping me shift from reacting to everything in real time to actually planning ahead, creating structure, and building a team that can carry the vision forward with me.

This kind of growth also brings up all the classic solo-preneur challenges: learning to delegate, knowing what to invest in, letting go of control, staying focused without doing everything myself and very important: pick the right team. I hadn’t done that very well, I was too trusting and too concerned with FAWNING when things got tough. I’m learning how to balance trust with taking care of business when there’s SMOKE, not a full on BLAZING FIRE. With a great team that may take a bit longer to assemble that I realized, I now can trust the process, trust that I don’t have to have my hands on every detail for it to be done well. It’s uncomfortable sometimes, but it’s also exactly the work I need to be doing if I want this to grow. Which I do!

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