Transformational Coach | Digital Mental Health Strategist | Keynote Speaker | Founder of the T.R.A.I.L. Method™
Reinvention For The Restless And Ready
BIO
Kali is a transformational coach strategist, a digital mental health strategist, and the founder of The Earthy Executive, a dynamic coaching and consulting platform. With a background that spans continents and industries—from tracking poachers in Costa Rica to singing in a gold-record German girl band—Kali brings a rare blend of adventure, mindfulness, and strategic insight to her work with purpose-driven professionals and startups.
Her expertise was sharpened and spotlighted during her time at Headspace, a global leader in mindfulness and digital mental health. There, Kali helped pioneer and scale the standard for virtual behavioral health coaching, first as a coach and later as a senior leader. She helped shape the coaching model that has since supported millions of users worldwide, led a team of professional coach managers, and worked cross-functionally to build emotionally intelligent cultures inside fast-paced startups and enterprise clients alike.
With a master’s in Counseling Psychology from Columbia University and a career rooted in transformation, Kali blends the depth of mental health expertise with the clarity and momentum of coaching. Her signature T.R.A.I.L. Framework (Try, Reflect, Align, Integrate, Lead) guides individuals and organizations through moments of reinvention with grounded courage and intention.
Whether supporting startup founders, executive leaders, or women rewriting the second half of their story, Kali is known for helping people return to what matters most—so they can lead with clarity, communicate with heart, and live in alignment with their values.
She is the author of the upcoming book The Inner Trail to Outer Freedom and a speaker on reinvention, mindful workplace, and women's empowerment.
The Earthy Executive Coaching & Consulting, LLC
The Earthy Executive is a coaching and consulting practice for high achievers navigating change and seeking alignment. Through personalized coaching, strategic advisory, and immersive retreats, Kali helps individuals and organizations:
Clarify their next chapter
Align leadership with values
Build emotionally intelligent teams
Navigate pivots with confidence and courage
At the heart of the work is a belief: Reinvention is the art of becoming whole.
Grounded - Magnetic - Unforgettable
Grounded - Magnetic - Unforgettable
Speaker
Kali is available for keynotes, panels, and podcasts, ERGs and wherever people talk. Her most requested topics include:
Reinventing Yourself Without Burning It All Down
Mindful Leadership in a World on Fire
The T.R.A.I.L. Framework: A Map for Purposeful Reinvention
The Inner Trail: Lessons from Nature, Motherhood, and the Boardroom
How High Achievers Can Reconnect with Their Purpose and People
Books
Coming Fall 2025!!
A bold and heartfelt guide for those ready to rewrite their next chapter—with purpose, adventure, and soul. This book offers personal stories, coaching prompts, and insights to help readers navigate quarter/mid/late life transitions, burnout, and the longing for reinvention.
Sample Interview Questions For The Media
You’ve lived many lives—pop star, rainforest protector, therapist, coach. What thread connects all these chapters for you?
How did your upbringing shape the way you see the world today?
What moment in your life felt like the biggest “pivot,” and how did you find your footing again?
Can you share a time when you felt completely lost—and what helped you find your way back?
What does “freedom” mean to you now, compared to when you were in your twenties?
What exactly is The Earthy Executive—and how did the idea come to life?
You’ve worked in mental health, mindfulness, and leadership—where do you see the biggest gaps in how we support people at work?
What’s one common myth about career success that you love to challenge?
Can you explain the T.R.A.I.L. Framework you use in your coaching practice?
How do you help high-functioning individuals slow down enough to rediscover what matters?
Tell us about your upcoming book The Inner Trail to Outer Freedom—who is it for, and what do you hope readers take away?
How did your podcast The Inner Trail begin, and how has it evolved with you?
You’ve delivered dozens of workshops—what makes a truly transformative workshop experience in your view?
As a mother, entrepreneur, and speaker—how do you stay grounded when life pulls you in different directions?
What’s the next personal or professional trail you’re excited to explore?
Kali On The Trail
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Contact Us
Interested in working together? Fill out some info and we will be in touch shortly. Look forward to hearing from you!
Email: contact@kalifieldswilliamsmedia.com
LinkedIn:
Website: www.theearthyexecutive.com