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The Chelese Perry Group

Discover transformative guidance to navigate leadership challenges and personal growth. True North Insights delivers actionable wisdom to align your decisions with your deepest values and ambitions.

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The counterintuitive secret to sustainable success (it’s not what you think)

September 9th, 2025 The Success-Happiness Paradox: Why High Achievers Are Getting It Backwards Hi, Reader, I spoke with a high-achieving tech executive last week who stopped me in my tracks. Despite reaching senior management and achieving everything on his “success checklist,” he felt empty, disconnected, and questioned whether all the sacrifices were worth it. Sound familiar? Here’s what I’ve discovered working with high achievers like you, reinforced by fascinating research I came across...

March 2026 Why leadership without inner authority no longer works “ “We can’t give what we don’t have. And if our internal wells are dry, no amount of external expertise will quench the thirst.” This week, I opened a box I’d avoided for ten years. It held divorce papers—documents from an earlier version of my life. Feeding them into the shredder, page by page, something loosened. Not dramatically. Quietly. As if each sheet disappearing marked a completion I hadn’t formally acknowledged. The...

February 2026 Hello Reader, What if I told you the issue isn't what you think it is? You've been telling yourself it's the workload. Or the boss. Or the politics. You've adjusted your schedule, set boundaries, and tried switching teams. And still, something feels off. Here's what I've noticed after nearly eight years coaching executives: You don't trust yourself. Not in the vague, motivational-poster way. I mean the daily, practical kind of self-trust that lets you: Make a decision and stand...

January 2026 January Check-In We're a few weeks into the new year, and I've been noticing something in my conversations with leaders: The gap between intention and reality is starting to show up. You started January with clarity. Perhaps you made resolutions, set ambitious goals, or decided what this year would be about. And now? The pace has picked back up. The demands are louder. The familiar patterns are reasserting themselves. And somewhere in the middle of it all, you might be asking:...

January 2025 Happy New Year! As we step into 2026, there's something about this particular moment that invites us to pause, reflect, and remember who we are beneath all that we've become. And lately, I've been hearing a theme from clients, colleagues, and women across every stage of leadership: “ "I'm successful... but I don't always feel like myself anymore." It's something many high-achieving women experience quietly, especially in midlife. When your identity becomes tightly defined by your...

A Note from My Heart: Gratitude, Rest, and Renewal As I sit with my tea this morning, reflecting on the year that's been, I'm struck by how this season always invites us into something we need: the gift of pause. The holidays offer us permission to slow down, to gather with those we love, and to honor everything we've moved through the challenges that stretched us, the moments of grace that surprised us, and all the beautiful, messy in-between. And in this quiet reflection, I keep coming back...

December 1, 2025 What's Waiting for You on the Other Side? Reader, let me be honest about this season. The holidays ask a lot of us. The gatherings, the expectations, the emotional labor of creating magic for everyone else. And if you're like many of the women I work with, part of you genuinely wants to show up fully. To savor these moments. To create something beautiful. And yet, you might already be running on fumes. Between navigating family dynamics, managing expectations, and holding...

November 2nd, 2025 Transforming High Achievers Into Harmonious Leaders Hi Reader, as this year quickly begins to wind down, I want to thank you — truly — for being part of this community. Your commitment to growth, reflection, and conscious leadership is what makes this space so meaningful. Because you’ve been walking this path with me, I wanted you to be the first to know about something special I’ve been quietly creating: ✨ RECLAMATION: Discover Your True North at Midlife ✨ A...

October 25, 2025 High-Achievers Into Harmonious Leaders Hi Reader, You're Not Having a Crisis. You're Having a Reckoning. I read Jessica Grose's piece in The New York Times this week, "American Women Are Leaving the Work Force. Why?"—and had to pause. Not because the numbers surprised me. I'm living them every week in my coaching sessions. 212,000 women left the workforce between January and August 2025. Meanwhile, 44,000 men entered. But here's what those statistics don't capture: the lived...

October 7, 2025 Transforming High-Achievers Into Harmonious Leaders Hi Reader, Have you ever had a conversation with a leader who didn’t try to fix you, offer advice, or fill the silence, but instead asked one question that shifted everything? That’s coaching. In today’s fast-changing, emotionally complex world, coaching is one of the most underutilized leadership skills available, especially for leaders committed to clarity, compassion, and purpose. If you care about building trust,...