want to find YOUR personal or professional summit?

Here in east Tennessee, we get to hike and share our beloved AT (Appalachian Trail). We locals can also be counted on to transport weary through-hikers to the closest hostel for a hot shower, package pick-up, and a meal that does not include trail mix. 

This is also what I do in my work. I help fellow trekkers and wayfarers when their vision and map has gotten muddy, their equipment needs upgraded,  or they need a complete base camp overhaul. 

My pivot from years of clinical work to speaking, training, coaching and consulting started from my own desire for a personal and professional HIGHER. I realized that supporting high-impact professionals translates to farther-reaching influence and healthier workplaces for people at all levels. I saw the ripple effect of individuals, teams, leaders and organizations committed to the actionable authentic, wholehearted real life and serve-first living, leading, and teaming for flourishing. 

And having trekked some miles with these inspiring people to their next summits- well, those sunrises are uniquely breathtaking.  


Because they FEEL and SEE and KNOW the mission and vision is being lived out, really happening, in conversations, projects, team dynamics and performance day-to-day.

They can confidently ask anyone in the  organization, “What do you like about your job?” and not feel anxious about the response. 

Their confidence in their own approach to resilient leading and teaming and living becomes positively contagious. 

My unique and time-tested Deeper to Higher© approach informs my workshops, keynotes, and retreat intensives. It incorporates the Enneagram, my clinical background and expertise, and thousands of hours of conversations with leaders and professionals just like you.  If it sounds a little scary and uncomfortable but intriguing and exciting at the same time, we are probably a great fit!  Sometimes new heights come from challenge or crisis. Sometimes they come from a long season of success that just doesn’t feel fun anymore. Sometimes, others have to help us recognize we’re stuck or struggling. Or we don’t know why but we know we need  a new trail, new boots, and a fresh set of eyes on the map and compass (that’s me!)

I facilitate clarity of vision, increased awareness, resilience and transformation – big ideas that translate to big impact and big return on investment. I’m a trek guide—resourcing, equipping, and encouraging deeper understanding of motivations, agility, and aptitude for self and others.

The result?

Personal and professional satisfaction, effectiveness and engagement that come from living and leading authentically. 

Bottom line?

Your summit at sunrise is waiting!

Dr. Natalie CUPPLES Pickering (trail name: edna) is your trek guide. here's the bio in brief.
and you'll have to reach out to get the story behind my trail name.

Dr. Natalie Cupples Pickering, PhD, BCC, ACC is a licensed psychologist and board-certified coach with 20 years of clinical, coaching and consulting experience across a wide range of settings, including international. Her careers in education and the fitness industry complement her whole-person approach to supporting  well-being in life, work and leadership. Through her unique individual retreat programs, workshops, and coaching, Natalie shows you how to leverage your strengths, recognize blind spots, and build an individual, team or organizational resilience plan. 

Natalie is genuine, honest (she’s an Enneagram 1 after all), creative and committed. You can read it from others below. But be assured, her knowledge of the terrain will help you and your team  reevaluate what you are carrying in your trek “pack”, why you chose it, what may no longer be useful and what new gear is needed for this stage of the climb.

You will be wholly prepared to discover your view of the summit at sunrise.

Read more about her EXPERIENCE and APPROACH.

How We Help


Personal and Professional Coaching via coaching packages or the High Places Coaching Trek Intensive model.


Dr. Pickering speaks on a range of leadership and development topics to audiences large and small.


Team and leadership development consultation services specializing in emotional intelligence, conflict resolution,  and organizational culture and resilience.

summit 9

Enneagram training, workshops, courses to support individuals, teams and organizational EQ at any stage of their Enneagram journey.

What Clients Say

I have helped many people in many places on many paths towards their personalized deeper and higher best… in their work, relationships, personal growth, leadership, effectiveness and performance. I coach with genuine, focused commitment to your vision resulting in clarity of direction, self confidence, enhanced sense of personal meaning and purpose.

For many, this is akin to offloading unnecessary items in your pack -items that could be useful to someone, may have been useful to you on a particular trail section but are no longer helpful or needed for this stage of your climb!


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FREE “UNBURNOUT BASICS: A Personalized Guidebook”



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