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    Meet Kristen

    “What if every choice to choose yourself, hard goodbye, and brave new beginning led you home? This isn’t about becoming someone new—it’s about remembering who you’ve been all along.”

    Kristen Chimack, a former Fortune 50 executive, embodies the courage to choose oneself. Over her 30-year career, she rose from payment clerk to executive, navigating diverse roles in finance, HR, sales, and more. Despite her success, Kristen felt the pull for something more authentic, leading her to leave a six-figure role to found Down-to-Earth Insights LLC.

    At Down-to-Earth Insights, Kristen’s mission is to empower individuals to choose themselves with courage and authenticity. Through coaching, speaking, and writing, she helps others transform their definition of success from fitting someone else’s mold to being exactly who they are meant to be. She offers individual coaching, an online course called     Permission to Shine, and hosts a free community called The Courage Collective, where individuals can connect, grow, and support one another.

    While Kristen loved her path after leaving Corporate America, she missed the world of events. In the spring of 2024, she began her work as The Hotel Whisperer. As an independent licensee for HelmsBriscoe, Kristen helps businesses, associations, and individuals find the perfect hotel or resort for their meetings. By removing the legwork involved in city and hotel research, writing RFPs, organizing responses, and negotiating contracts, Kristen ensures her clients can focus on their event’s success without the stress of venue logistics. Her services are designed to save clients time, money, and hassle—all at no cost to them.

    When she’s not transforming lives through her work, you might find Kristen enjoying a Law and Order: SVU marathon, creating memorable experiences with her nieces and nephews, or cheering on Chicago sports teams alongside her husband, Mike.

    Are you hearing the whispers or feeling the pull to something more? Kristen is ready to support you on your journey.

    Coaching Philosophy

    My approach is to offer relatable, practical coaching that empowers you to unlock your full potential in every aspect of life. My journey from a Fortune 40 corporate executive to an independent business owner and coach has been a path of discovery, resilience, and growth.

    Throughout my career, I’ve navigated complex challenges, including leading turnarounds, spearheading startups, and thriving in demanding environments. These experiences have profoundly shaped my coaching style and my commitment to making coaching accessible to everyone, not just executives. In transforming my career, defining my personal brand, networking effectively, and building a strong presence on LinkedIn were pivotal steps. These are skills and insights I now passionately share with others.

    As your coach, I aim to empower you with practical, authentic, and relatable guidance. Whether you’re at the beginning of your career, contemplating a change, or striving to improve your leadership skills, I’m here to support you in realizing your full potential.

    The Hotel Whisperer

    Kristen joined HelmsBriscoe as an independent agent and Manager, Global Accounts in March of 2024. Based in Bloomington, Illinois, she stands ready to serve as an invaluable extension of your team.She is committed to closely collaborating with you to thoroughly understand your meeting requirements before providing comprehensive services. These services include site selection, contract negotiations, and mitigating risks, thereby allowing you to concentrate on the strategic imperatives of your meetings.She is driven by her passion for crafting unique and memorable experiences for everyone around her and is eager to extend this passion to assisting you in planning unforgettable events.

    Personally

    On a personal note, my life is enriched by a supportive husband, two stepchildren, and a large, loving extended family of nine nieces and nephews, plus two great-nieces/nephews.

    My passions include the thrill of live sports, exploring new countries, and savoring quiet evenings at home with a glass of wine and a game of Skip-Bo.

    Together, we can transform your aspirations into achievements. My commitment is to guide you through every twist and turn of your professional path, ensuring that each step is a stride towards fulfillment and success. Let’s begin this journey with a shared vision and a promise of continuous growth and discovery.

    Speaking & Podcasts

    Why Interview Kristen?

    Are you standing at a career crossroads? Feeling trapped in a toxic environment? Wondering if there’s more to life than climbing the corporate ladder?

    You’re not alone. After 30 years in corporate America, I realized that choosing yourself isn’t selfish—it’s essential.

    Through my book, speaking engagements, and coaching, I share practical strategies for navigating life’s transitions with authenticity and courage. I know firsthand what it’s like to feel stuck, unsure of what’s next, and overwhelmed by the fear of leaving what’s familiar.

    Whether your audience is questioning their career path, feeling the strain of burnout, or seeking permission to choose themselves, I offer     real talk, relatable stories, and actionable insights — all delivered with warmth, honesty, and maybe even a little humor (Diet Coke optional but highly recommended!).

    If you’re looking for a guest who can inspire your audience while providing tangible steps to help them move forward, let’s connect. I’d love to bring authentic insights and transformative strategies to your next event.

    SPEAKER

    Are you looking for a speaker who combines corporate experience with authentic truth-telling? As a former Fortune 50 executive who chose to rewrite her own success story, I share practical wisdom wrapped in real-life stories that resonate with audiences ready for change.

    Popular Discussion Topics Include:


    ●   The Cost of Choosing You: Making Peace with Big Transitions – Discover how to recognize when it’s time for change, navigate the emotions of major transitions, and find the courage to choose yourself – even when it means walking away from the “sure thing.” Using my Growth Through Grief Spiral framework, I’ll show your audience how to turn career transitions into opportunities for authentic growth. (And yes, sometimes that growth comes with a side of tears in your car – been there!)


    ●   From Whispers to Roars: Learning to Trust Your Inner Wisdom Ever ignored that quiet voice telling you something needs to change? Through stories from my journey, I share how to recognize and trust your body’s early warning signals before they become screams. Discover practical tools for tuning into your inner wisdom and finding the courage to act on it.


    ●   Exit Interviews Are Too Late: Creating Cultures Where People Choose to Stay When’s the best time to retain an employee? Long before they start updating their LinkedIn profile. Through candid stories and proven strategies from my 30-year corporate journey, I’ll show you how to identify the whispers of disengagement before they become resignation letters. Learn how to create meaningful “stay conversations,” develop early warning systems that actually work, and build a culture where choosing to stay feels as intentional as choosing to leave. Your organization will gain practical tools for transforming standard retention practices into authentic connection points that honor both your business goals and your people’s humanity.


    ●   Values Beyond the Wall Art: Building Cultures of Authentic Alignment Ever walked into an office with “Integrity” beautifully painted on the wall while witnessing the exact opposite in action? Through compelling stories and practical frameworks, I reveal the true cost of the gap between stated values and lived experiences. Learn how to conduct a “values reality check,” create feedback systems that surface truth without fear, and develop leadership practices that bring your values off the wall and into your daily operations. You’ll walk away with concrete strategies for building a culture where people don’t just recite your values in onboarding—they actually experience them every day. (And no, the solution isn’t redesigning your values wall with better fonts!)

    Article Links

    TESTIMONIALS

    Kristen’s session was a standout—engaging, fresh, and filled with real-world advice. Her ability to connect with the crowd and deliver value made her one of our most talked-about speakers. Laurel, Conference Event Planner

    Laurel
    Conference Event Planner

    Kristen was an amazing guest with profound insights.

    Elisha
    Podcast Host

    Kristen Chimack was a truly inspiring guest on The Inspired Choice podcast. With heart, clarity, and hard-earned wisdom, she shared her powerful journey from corporate executive to courageous entrepreneur, offering deep insights on authenticity, reinvention, and choosing yourself. Kristen’s presence was both grounding and energizing, and her storytelling resonated with listeners navigating their own life transitions. She’s a voice of empowerment and realness—an unforgettable guest.

    Caroline
    Podcast Host

    Questions?

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