Alright – so today we’ve got the honor of introducing you to Michelle Pollack. We think you’ll enjoy our conversation, we’ve shared it below.

Michelle, thanks for joining us, excited to have you contributing your stories and insights. What do you think matters most in terms of achieving success?

Most of us were handed a definition of success before we were old enough to question it. It started in school where success was getting A’s and getting into the “right school.”

We learned early that success meant figuring out what each teacher wanted and adapting to it. Every class had different standards—so we got good at shape-shifting to meet someone else’s expectations.

So it’s no surprise that when we enter the working world, we keep doing the same thing. We chase promotions, titles, gold stars, and the external validation that we’re doing a good job.

Except I’ve coached enough high-achieving women to know that following that formula often leads to burnout, self-doubt, and a persistent voice whispering, “Is this it?”

What if, instead of learning to conform, we’d been encouraged to challenge a teacher’s perspective? To think for ourselves? To bring something new to the table?

I believe true success is deeply personal and constantly evolving. For a lot of people, success will look totally different at 45 than it did at 25 but it’s rare for people to really allow themselves to explore that.

My client Ruby (name is changed) is a great example. When we started working together, she was the Associate Dean at a medical school in Manhattan. On paper, she had everything she’d worked for—but she was exhausted and disconnected from what had once driven her. She wasn’t even sure she wanted to stay in academia.

As we dug deeper, she realized she’d spent years navigating politics and avoiding conflict, leaving no room for what she truly loved: mentoring students and fighting for equity in medical education. She was making everyone else happy—except herself.

Redefining success meant giving herself permission to imagine something completely different. She explored leaving academia and medicine altogether – and ultimately realized she didn’t want to leave either. She just needed to leave that job.

Ruby took on a new position at one of the top universities in the country, one that allowed her to lead with purpose and impact. She also ran her first marathon and found more time for herself and her family—for the life part of her life.

What changed wasn’t just her job. It was her definition of success. She stopped abandoning herself in the name of getting ahead—and started owning what “success” looked like on her own terms.

I believe that true success is about building a life and career that FEELS good as it looks on your LinkedIn profile. What’s the point of the titles and the money and the accolades if you’re still sitting there thinking, “Is this all there is?”

So what does it take to be successful? It takes courage. It takes the willingness to question the path you’re on, to listen to your gut even when it doesn’t align with what’s expected, and to stop waiting for someone else to give you permission or worrying about what other people think about it. And it requires a willingness to take risks and experiment. You can’t get it right without being willing to risk getting it wrong.

AND success often requires being willing to get support— because it’s really hard to see the label from inside the jar.

So many of the clients think something is wrong with them – they can’t understand why they’re STILL not satisfied after doing everything “right”. And when they try to figure it out themselves, they spiral into self judgement, overwhelm and thinking that keeps them stuck

That spiral isn’t a personal failing—it’s a red flag that it’s time for change. You don’t need to push harder. You need to ask better questions so you can determine what success mean to YOU. That’s where the real work begins.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I’m an Executive Leadership coach. I work with high-achieving women to break through burnout, perfectionism, and second-guessing so they can lead with confidence, clarity, and fulfillment — without sacrificing themselves in the process.

My clients are powerhouses — lawyers, creatives, executives, entrepreneurs — who’ve done everything “right” and still feel stuck. They’re overwhelmed, burned out, and quietly wondering: “Is this really it?”

I know that place. I lived it.

I was the girl who had her entire life planned out straight A student, National Honor Society, competitive dancer, lead in the musical, off to Northwestern for a degree in theatre. From the age of three, I knew I was going to be a Broadway star. But a few years into performing professionally, I found myself cartwheeling across the room at a callback for the national tour of Annie Get Your Gun — and something inside me snapped.

I didn’t want this life anymore. I had no idea what I did want. But I knew I had to figure it out.

That set me on a decades-long journey of reinvention. I went from acting to producing, then became a Creative Executive in television, working on shows like Grease LIVE!, Avenue Q, The New Adventures of Old Christine, and Without a Trace. My career was shiny, impressive… and deeply unfulfilling.

I was miserable. I was climbing a ladder that led me further and further away from myself. I shape-shifted daily to fit into a toxic culture that valued silence over creativity, hierarchy over humanity. I abandoned my voice. I swallowed my instincts. I locked away the bold, creative, connected woman I had once been. I convinced myself this was just how it is.

Then I got laid off when I was eight months pregnant (5 months after a promotion when they DIDN’T know I was pregnant…)
But as angry as I was, I was also forced to confront how far I’d drifted from myself.

Ultimately, that moment cracked something open.

Instead of rushing back to what I knew, I gave myself permission to find what I wanted. That search led me to coaching — and from my very first training, I stopped looking around for what else might be out there. I knew I’d found the thing.

Today, I run a thriving coaching practice where I get to see my clients create the legacies that they truly want to leave.

Through my 1:1 coaching, group programs, workshops and speaking, I guide clients through The Art of Compassionate Command™ — my signature methodology that blends research-backed tools with deep inner work. As a Certified Co-Active Coach (CPCC) with additional certifications in Positive Intelligence and the Playing Big methodology, I bring both extensive training and real-world leadership experience to our work together to help women lead with clarity, confidence, and authenticity. This work isn’t just about hitting goals and surface-level fixes. We’re not just solving for productivity— we’re unlearning perfectionism, people-pleasing, and fear-based leadership so clients can build sustainable success aligned with their core values.

I typically work with three types of clients — maybe you’ll see yourself in one of them:

The Unfulfilled Achiever: You’re successful on paper — impressive title, glowing track record — but inside, you’re quietly wondering, “Is this really it?” Every achievement feels a little more hollow, and you’re craving something with more meaning.

The Self-Doubting Leader: You have the ideas, the vision, and the respect of your peers… but you still second-guess yourself. You reread emails a dozen times. You preface great suggestions with “This might be a bad idea…” You’re poised for more — but afraid to fully own it.

The Stuck High-Performer: You’re the go-to person. Everyone relies on you. You deliver, over and over — but you’re watching others get promoted while you stay stuck. You’re exhausted, frustrated, and ready to figure out what needs to shift.

Sound familiar? You’re not alone.

And here’s something I always tell potential clients: It doesn’t matter whether I’ve worked in your industry. In fact, sometimes it’s better that I haven’t. My job isn’t to give you advice about your business — it’s to ask the right questions that uncover what works for you. Because when someone tells us what to do, we tend to resist and find all the reasons it won’t work. But when WE figure out the answer, we own it.

I’m known for creating a space where radical honesty becomes possible. My clients often describe me as their secret weapon: both their fiercest champion and their most honest mirror. I help them hear the patterns in their stories, reconnect with their inner wisdom, and stop hiding behind outdated definitions of success.

What truly sets my work apart is its depth and holistic impact. Unlike coaching approaches that focus solely on external achievement or workplace dynamics, my methodology addresses the whole person. We examine the patterns that show up across all domains of life, creating shifts that transform not just how you lead at work, but how you show up for yourself, your relationships, and your deeper purpose. My clients don’t just get promoted or build businesses — they transform the way they lead, the way they parent, the way they take up space in the world.

I’m most proud of creating a coaching practice where radical honesty becomes possible. In a world that often asks women to shrink or adapt themselves to fit in, I’ve built a space where my clients can finally put down that exhausting armor. Watching a client reclaim her voice after years of self-censoring or seeing her negotiate confidently for what she deserves after a lifetime of settling — these moments of courage and self-reclamation are what make this work so meaningful.

And this work extends far beyond individual transformation. What I’ve come to understand deeply is that owning who you want to be in the world is a radical act of social justice. Because when you do this work, you begin to model a new way of being for women everywhere. You begin to change the DNA for future generations of women so that they don’t feel the same pressures of perfectionism and people-pleasing that women have lived with for centuries. You start to change the world.

What brings ME fulfillment is watching a woman come home to herself. That moment when she stops asking for permission and starts owning who she is — unapologetically. It’s the text message months after our work together telling me she finally launched the project, or the email about how our work together helped her have a difficult but necessary conversation that changed everything or negotiate the raise that she deserves.

If you’re feeling the weight of achievement that doesn’t fulfill you, or sensing there’s more for you but struggling to find it — I’d love to connect. Breaking through burnout, perfectionism, and self-doubt feels so much simpler when you don’t have to do it alone.

What’s a lesson you had to unlearn and what’s the backstory?

I had to unlearn the idea that being a great coach would be enough to run a sustainable and successful coaching business.

When I started out, I thought I’d spend my days doing deep, transformational work with clients — and I do. But I quickly learned that coaching is only one part of the business. If I wanted to actually have a business, I had to become a CEO. And that meant learning how to sell, market, articulate my value, build offers, set boundaries, create systems — and I had ZERO training in any of these things.

Honestly? I struggled for a while. I found a business coach who helped me with a system for referrals and creating a values-based sales process. That was step one. But the marketing was a WHOLE different ball game. It was excruciating. I’d stare at my calendar blocked for “content creation” and feel completely paralyzed. I’d spend hours drafting a single post, then delete it because it didn’t sound “professional enough.” I kept looking for a “system” that would work, but I couldn’t find one that felt like it worked for me. I just kept saying to myself, “My brain doesn’t work that way.” I couldn’t understand why everyone else had a blueprint that worked and mine was just broken.

And then literally a month ago, I was diagnosed with ADHD. At 49!

The diagnosis was like someone finally handed me the right map after years of trying to navigate with one for a completely different terrain. There was this profound sense of relief, but also grief for all the years I’d spent blaming myself for what I now understand is just how my brain is wired. I realized that I wasn’t “bad at marketing” — I just hadn’t been taught how to do it in a way that worked with my brain. I started finding systems that actually supported the way I process, focus, and create. Now, I batch-create content during my high-energy times, use voice memos instead of writing when I’m feeling stuck, and build in find ways to capture the moments where content ideas come to me in totally random moments. And it’s starting to feel different – sometimes even enjoyable.

That was a massive unlearning for me: not everything people teach you is meant for you. You have to eat the fish and spit out the bones. You have to come back to your gut, again and again, and ask: Does this actually work for me? And you have to keep trying. You have to keep what’s working, look at what’s not and determine how you want to iterate based on what didn’t work before. If you just throw out the way you did it every time it doesn’t work, you’re making things SO much harder for yourself!

This personal journey has deeply informed my coaching methodology. The Art of Compassionate Command™ grew out of my own struggle to lead myself authentically before I could truly help others do the same. It’s why I’m so passionate about helping my clients find approaches that honor their unique wiring and strengths, rather than forcing themselves into someone else’s template for success.

Whether they’re redefining success, navigating a career transition, or stepping into leadership, the work is never about copying someone else’s path. It’s about discovering your own — and building systems, boundaries, and support around that.

So being a great coach wasn’t enough. I had to become a business owner. A leader in my own right. A self-trusting woman who knows how to build something real in a way that’s sustainable, honest, and uniquely mine.

That’s what I unlearned. And it’s what I teach now, too.

How’d you build such a strong reputation within your market?

I built my reputation the same way I coach my clients to lead: with clarity, courage, honesty — and by owning exactly who I am.

When I first started, the challenge wasn’t knowing how to coach – it was finding the courage to be fully myself in a market full of polished, perfect-looking brands. I’m not the executive coach in a power suit who spent years behind a desk. I come from a different world — and owning that is my differentiator, even when it feels vulnerable.

My clients come to me because they’re stuck in cycles of burnout, perfectionism, people-pleasing, and self-doubt — and they stay with me because I don’t try to fix them. I help them see what they’ve been too deep in to name. I listen hard. I hear the patterns in their stories. And I reflect it all back with both compassion and truth.

For example, one leader came to me convinced she needed to be more decisive and authoritative. But through our work together, she realized her natural collaborative style was actually her superpower – she just needed to own it confidently instead of apologizing for not fitting the traditional leadership mold. She got clarity. She started showing up differently. And that shifted everything.

What really helped me build my reputation is my clients. Without them, I wouldn’t have a business. I’ve built this almost entirely through word of mouth. Some of my clients have referred five, six, even seven other women to me. Not because I asked them to — but because the work changed something for them, and they wanted that for the people they care about. That kind of trust is the greatest compliment I could ever receive.

As my practice has grown, I’ve also contributed to my professional community through workshop facilitation, speaking engagements, and collaborations with other women-focused leadership organizations. These connections have expanded my reach while staying true to my core mission.

I’ve built this business to be values-driven — rooted in connection, courage, and what I call spark — that feeling when you’re fully alive and doing the thing you were meant to do. I’ve learned how to lead my business the same way I teach my clients to lead their lives: with intention, boundaries, and integrity. That means growing in ways that are aligned, sustainable, and true to who I am — not just what looks good from the outside.

So what built my reputation? Deep listening, laser-sharp coaching, radical honesty — all delivered with heart. I don’t promise quick fixes. I promise transformation. And I’ve built a business around that promise being kept. At its core, this work isn’t just about methods—it’s about connection. When clients see that I’m willing to bring my whole self to our work together, it creates space for them to do the same. My clients don’t just trust my methods; they trust me because they can feel that I believe in their capacity to transform and they begin to see themselves through that lens as well.

Contact Info:

• Website: https://www.michellepollack.com/
• Instagram: https://www.instagram.com/michelleepollack/
• Linkedin: https://www.linkedin.com/in/michelle-pollack/

Image Credits

Studio 5800
Last photo only – Michael Puck