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

Hi Anitra, thanks for joining us today. Let’s start with a fun one – what’s something you believe that most people in your industry (or in general) disagree with?

Most career advice treats work and life as two competing forces, something to balance, integrate, or manage against each other. But I reject the idea that work and life are in opposition in the first place.

Think about your body and your health. No one says, “I’m trying to balance my body and my health.” That wouldn’t make sense because your body is part of your health, not something separate from it. If you only focus on physical fitness but ignore mental well-being, finances, or relationships, you won’t actually be healthy. True health requires all of these elements working together.

We make the same mistake when we talk about work and life. The opposite of work isn’t life. It’s rest or play. And the opposite of life isn’t work. It’s death. Work is simply one piece of a fulfilling life, not something separate that needs to be balanced against it.

Instead of asking how to balance work and life, we should be asking how to create a fulfilling life, one that includes fulfilling work and fulfilling play. The goal isn’t balance. It’s wholeness.

When your work aligns with your strengths and values, it becomes a meaningful part of your overall life experience, not something you have to manage separately.

That’s the shift I want more people to make. Not to work harder, but to work in a way that actually supports the life they want.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

About Me
I’m Anitra St. Hilaire, a wife and mother of two who loves to read and learn all the things. My work spans leadership, coaching, and wellness—all connected by a common thread: helping people create lives that actually feel good to live.

As VP of People at ThreeFlow, I focus on building a workplace where people feel valued, supported, and empowered to do their best work.

Through My Authentopia, I help high-achievers, especially women, break free from feeling stuck and build careers that actually feel good to live. My coaching is for those who have followed all the rules of success but still feel unsatisfied, overworked, or unseen. They’re accomplished, driven, and smart—but they find themselves wondering, Is this really it? I help them figure out what they actually want and how to build a career that supports their version of success, not someone else’s.

How I Got Here
For a long time, I was a high achiever trying to fix myself with the next job, the next title, or the next level of success.
Even though I was interested in psychology, I started my career in finance because I thought that’s what successful people did. I hated it. So I went to grad school, still unsure of what I wanted. I became a consultant because that seemed like something successful people did after grad school. I then transitioned into HR and eventually worked my way up to Chief People Officer. On paper, each move looked like progress. But inside, I was restless, drained, and unfulfilled.

I kept thinking that if I just found the right job, the right company, or the right title, everything would finally click. But it never did.

At some point, I had to stop and ask myself: Why do I keep feeling this way? What am I actually chasing?
What I realized changed everything.

I didn’t need a new job. I needed a new approach to how I made career decisions. Instead of looking for external markers of success, I started with what I actually valued—freedom, honesty, and meaningful impact. I stopped trying to fit into careers that looked good on paper and built one that fit me.

Now, my work is a mix of leadership and coaching. But more than anything, it’s a mix of who I actually am.

Who I Help & How
I work with high-performing professionals, often director-level and above, who feel stuck, undervalued, or disconnected from their work. They might:
*Hate their job but feel unsure about quitting or switching careers.
*Feel lost or unfulfilled despite having a strong career.
*Struggle to get promoted despite their achievements.
*Dread meetings, feel unseen, or want more from life than work stress.

My coaching helps them stop spinning in uncertainty and start making clear, intentional decisions. We strip away the noise of what they should do and get to the truth of what they actually want. Then, we create a plan that aligns their career with their values and strengths—so they can move forward with confidence and ease.

What Sets Me Apart
I help my clients:
*Figure out what’s actually making them unhappy (spoiler: it’s usually not just the job).
*Redefine success on their terms instead of chasing promotions that won’t fulfill them.
*Make clear, intentional decisions—whether that means staying, leaving, or reshaping their career.
*Develop deep self-awareness and confidence so they stop second-guessing themselves.

I don’t do quick career hacks or surface-level fixes. I focus on the real work—the deep identity shifts that lead to lasting fulfillment.

What I’m Most Proud Of
The people I work with don’t just walk away with a new job or a clearer career path. They walk away changed. They gain clarity, confidence, and a sense of freedom they didn’t think was possible. They stop forcing themselves into careers that don’t fit and start making decisions from a place of truth. Seeing them step into their power, finally feel at home in their careers, and build lives that energize them? That’s what I’m most proud of.

What I Want You to Know
*You don’t have to settle for feeling unfulfilled just because you’ve invested time in your career.
*Success doesn’t mean sacrificing yourself for work.
*The way forward isn’t just another promotion—it’s understanding what actually matters to you.
*You’re allowed to change your mind, shift your career, and prioritize your happiness.
*You deserve to feel good—mentally, emotionally, and physically.

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

Early in my career, I prided myself on being able to read people. I could usually tell when there was more behind someone’s words: picking up on body language, tone, and subtle cues. And for the most part, this intuition served me well.

But then I learned the hard way that intuition isn’t always right.

Years ago, I had a conversation with a staff member I knew well. We had a solid rapport, and this person seemed frustrated, disengaged, and not in a great place. Based on their behavior and what I thought I was picking up, I asked if I could speak plainly and said:

“Are you thinking about leaving? Because if you are, I’m happy to have an honest conversation about that.”

I genuinely believed I was opening the door for a real conversation. I thought they’d appreciate having a safe space to talk about their options.

That’s not what happened.

Instead, they were taken aback—almost offended. They weren’t thinking about leaving at all. They were struggling, yes, but they wanted support in making things better, not an assumption that they were on their way out. Worse, my question planted doubt where there wasn’t any before. Suddenly, they were worried that others might think they were leaving, that their job security might be questioned, that their struggles had been misread in a way that could hurt them.

It was a tough but necessary lesson: You don’t always know what someone is thinking. No matter how strong your intuition, your job isn’t to assume—it’s to listen and let them tell you.

I had to unlearn my tendency to lead people toward a conclusion I thought was obvious. Yes, intuition is a strength. Yes, gut feelings can be valuable. Yes, being empathetic matters. But the best leaders—and the best coaches—don’t assume. They stay curious. They ask open-ended questions without steering someone toward a particular answer.

This experience made me a better leader, but more than that, it made me a better coach, parent, spouse, and friend. Learning how to really listen, how to create space for people to come to their own realizations rather than rushing to a solution—that’s the work. And it’s a lesson I’m still practicing every day.

Are there any books, videos or other content that you feel have meaningfully impacted your thinking?

Most people turn to business books for insight, but I’ve found some of the most powerful lessons in books written for children. The simplicity of the stories and the way they distill core truths makes them unforgettable.

One of my favorites is “We’re Going on a Bear Hunt” by Michael Rosen. It’s about a family setting off on an adventure to find a bear, but along the way, they run into one obstacle after another—tall grass, a deep river, thick mud. And each time, they repeat the same line:

“We can’t go over it. We can’t go under it. We have to go through it.”

That line has become a mantra for me. It’s exactly how challenges work in real life. Whether it’s a tough leadership moment, a career crisis, or an unexpected detour, there’s no shortcut. You have to go through it.

Another favorite is “The Phantom Tollbooth” by Norton Juster. It’s about a boy, Milo, who feels bored and directionless—until he’s given a new way to see the world. Through his journey, he realizes that meaning, curiosity, and purpose weren’t missing from his life—he just wasn’t looking for them in the right places.

That lesson has stuck with me. So many high-achievers, whether they’re executives, founders, or something else, get caught in a cycle of chasing external success without ever stopping to ask what they actually want. They climb ladders they don’t even care about simply because they believe that’s what they’re supposed to do.

The Phantom Tollbooth is a reminder that the biggest obstacles to fulfillment aren’t external. They’re the assumptions and limitations we don’t even realize we’ve accepted. That shift is powerful—not just for executives and leaders but for anyone trying to create a career and life that actually feel good.

Instead of asking, “What’s the next thing I should achieve?” we should be asking, “What excites me? What kind of work feels meaningful? Where do I actually want to go?”—not just where I can go.

Yes, there are incredible books on business strategy and leadership, and I’ve read many of them. But sometimes, what we really need is a reminder of something simple and true.

Contact Info:

• Website: https://myauthentopia.com
• Facebook: https://www.facebook.com/anitra.sthilaire/
• Linkedin: https://www.linkedin.com/in/anitrasthilaire/