Today we’d like to introduce you to Kristen Chimack.
Hi Kristen, it’s an honor to have you on the platform. Thanks for taking the time to share your story with us – to start maybe you can share some of your backstory with our readers?
I had what most would consider the ultimate success story. For 30 years, I worked my way up from an entry-level payment clerk to an executive role at a Fortune 50 company. But my favorite role came from running what my family playfully dubbed ‘Aunt Kristen’s Leadership Academy’ – where playing, hanging out, and claw machine strategies were just as important as business decisions.
While climbing the corporate ladder, I started a tradition that became legendary in our family – the ‘5-year-old trips.’ Each niece and nephew gets to choose their own US adventure when they turn five. From riding Space Mountain six times in a row to creating stories at the American Girl store in New York City, these adventures became lessons in courage and curiosity. Between arcade challenges (we’re slightly obsessed with claw machines), bowling tournaments, and impromptu dinner conversations, I got to be fully present in their lives in ways that transcended traditional mentorship. When my teenage niece and nephew turned their bracelet-making hobby into a $1,000 business, or when my college-aged nephew texts about how our Washington D.C. adventure sparked his interest in public service, I’m reminded that leadership isn’t just about corporate achievements – it’s about nurturing potential in all its forms.
When I left my corporate role, I made a conscious choice to build a life that aligned completely with my values. Instead of following the traditional path of focusing on just one thing, I chose to embrace all my passions. Because true success, I discovered, isn’t about fitting into someone else’s mold – it’s about having the courage to create your own definition.
This journey led me to embrace multiple roles that allow me to serve others authentically. As ‘The Hotel Whisperer,’ I help clients source worldwide hotels for their events, turning their dreams into reality without adding to their costs. It’s a unique blend of my corporate negotiation skills and my love for crafting meaningful moments – whether I’m securing a beachfront resort for a CEO’s staff retreat, coordinating hotels for a large conference, or finding the perfect venue for a client’s destination wedding.
Through Down-To-Earth Insights, my coaching practice, I’ve guided many women in supervisor, manager, director, and senior leadership roles to navigate their careers without compromising their authentic selves. My approach combines hard-won corporate wisdom with unexpected lessons from my role as Chief Adventure Officer of the Aunt Kristen Leadership Academy. My book, ‘The Cost of Staying,’ explores the real price of remaining in situations that don’t align with our authentic selves, drawing from both boardroom insights and the profound wisdom gained from watching young minds embrace their potential without fear of judgment.
Today, whether I’m coaching a leader through a company transition, sourcing the perfect venue for a client’s dream event, or planning next summer’s adventure with my youngest niece, I’m living proof that true leadership isn’t about choosing between professional success and personal fulfillment – it’s about having the courage to bring your whole self to everything you do.
We all face challenges, but looking back would you describe it as a relatively smooth road?
Like any journey worth taking, mine has had its share of challenging terrain. The decision to leave a secure executive position at a Fortune 50 company wasn’t easy. There were sleepless nights wondering if I was making the biggest mistake of my life, and plenty of well-meaning colleagues who questioned why I would walk away from such a ‘successful’ position.
One of the biggest challenges was recognizing that my own success in the corporate world came at a cost—one that many women in leadership positions silently bear. I had to confront the reality that the traditional metrics of success I’d achieved had required compromises I wasn’t willing to make anymore. Starting over as an entrepreneur in my 50s meant not just a career change, but a complete paradigm shift in how I defined success.
The transition brought practical challenges – learning to market myself after years of letting my corporate work speak for itself, building a coaching practice that required personal vulnerability, and establishing The Hotel Whisperer business from scratch with no guaranteed clients. But perhaps more challenging was developing an approach that honored both professional excellence and personal authenticity.
These struggles have become the foundation of my work today. They’ve shaped how I help other high-achieving women break free from burnout and realign their careers with who they truly are. Through my coaching practice, I’ve developed a deeply personal, experience-driven approach that goes beyond traditional executive-level strategies or generic corporate advice.
However, these challenges taught me invaluable lessons that I now share with my clients. They showed me that our greatest growth often comes from embracing uncertainty, and that what looks like a setback can actually be a setup for something better. Most importantly, they reinforced that authenticity – while not always the easiest path – is always the right one.
Appreciate you sharing that. What should we know about Down-To-Earth Insights, L?
Through Down-to-Earth Insights, I help high-achieving women in leadership break free from burnout and realign their careers with who they truly are. After experiencing firsthand the challenges that ambitious women face in corporate leadership roles, I developed an approach that goes beyond traditional executive coaching. Unlike conventional leadership coaches who focus solely on strategy or generic corporate advice, I bring a deeply personal, experience-driven methodology rooted in both my 30-year corporate journey and my decision to redefine success on my own terms.
What sets my practice apart is the recognition that leadership development isn’t just about acquiring new skills—it’s about reconnecting with your authentic self. I work primarily with women in director and senior leadership roles who appear to ‘have it all together’ on the outside, but privately struggle with constant pressure, endless meetings, and the exhausting challenge of proving themselves while managing teams and navigating office politics.
My coaching approach acknowledges both the external challenges these women face and the internal questions they’re grappling with. We move beyond surface-level solutions to address the deeper questions: Is this all there is? Have I outgrown this role, or is it me? How can I lead authentically without burning out?
I’m particularly proud of how this work is expanding through my newly released book, ‘The Cost of Staying,’ which explores the real price of remaining in situations that don’t align with our authentic selves. The book draws from both my executive experience and the countless conversations I’ve had with women leaders who are ready to redefine success on their own terms.
Additionally, I serve as ‘The Hotel Whisperer,’ helping clients source worldwide hotels for their events at no additional cost, leveraging my corporate negotiation experience to turn their vision into reality. This complementary service reflects my belief that success should be accessible and that great leadership includes knowing how to create meaningful experiences for others.
What truly sets my brand apart is its foundation in lived experience. Every service I offer—from one-on-one coaching to corporate workshops—is designed to help women lead with authenticity, confidence, and purpose, without having to choose between success and personal fulfillment. I’m proud that my work creates a space where ambitious women can be both highly successful and deeply authentic.
We’d be interested to hear your thoughts on luck and what role, if any, you feel it’s played for you?
I have an interesting perspective on luck, shaped by both my corporate years and my entrepreneurial journey. While I believe in creating your own opportunities through hard work and preparation, I can’t deny that certain pivotal moments in my life came from what others might call ‘luck.’
I was lucky to start my corporate career at a time when companies were beginning to recognize the importance of diverse leadership, though it still meant being one of very few women in many rooms. But what really matters is what you do with those opportunities. Any ‘luck’ I experienced was amplified by preparation and persistence.
Some of my greatest ‘lucky breaks’ actually came disguised as setbacks. When I faced particularly challenging situations in my corporate role, these experiences gave me the insights and empathy that now help me connect deeply with my coaching clients. The timing of my decision to leave my executive position – which felt terrifying at the moment – turned out to be oddly fortunate, as it positioned me to help other leaders navigate their own transitions.
Perhaps my luckiest break was growing up in a family that valued both ambition and authenticity. Those childhood adventures with my nieces and nephews weren’t just fun – they kept me grounded and reminded me that success comes in many forms. This perspective now influences how I help other women leaders define success on their own terms.
What I’ve learned is that luck isn’t just about good things happening to you – it’s about being prepared to recognize opportunities and having the courage to act on them, even when they don’t look like opportunities at first. Every ‘unlucky’ moment that pushed me out of my comfort zone ultimately led to growth that serves my clients today.
Contact Info:
- Website: www..kristenchimack.com
- Facebook: https://www.facebook.com/ksligar
- LinkedIn: https://www.linkedin.com/in/kristen-chimack/
- Other: https://calendly.com/kchimack/virtualdietcoke
