If you are ready to rise up to the next level of your life and dreams by releasing yourself from old looping patterns or Ennea Type trance and awakening to new reservoirs of energy in your inner eco-system, I invite you to read the details below and join me!

🌿✨ Courtney

You are invited into an experience of:

🍋 CONNECTION: Enjoy learning with a small group of conscious women.

🍋 CAPACITY: Deepen your Enneagram knowledge and skills and increase your vibrancy and resiliency by mapping the inner negative voices that block your growth and learning effective strategies to handle each one.

🍋 CLARITY: Discern what is and isn’t your priority for this next season of life and tools that support your consistent, inspired action (including new ways to relate to your calendar) so that you gain real traction toward your hopes and goals.  


Dates: 3 month program starts May 17

Choose Your Payment Option + Join Today!

Garden Party enrollment is currently full. But I will DEFINITELY be hosting it again — it has been really fun. Please enter your email here to stay connected and be the first to know when I’m offering it again. *I’ll also share with you a free copy of my book, The Flourish Formula. 

Testimonials for Coaching with Courtney

Katie Crouch“Courtney is a wonderful coach. As soon as we connect, I instantly start to relax and breathe as she has coached me to do so many times at the beginnings of calls. After coaching me through a cross-country move and then a decision to have another baby, I started working with her most recently on my dream of starting a copywriting business. Over the course of the past year, I went from buying a notebook and a file folder to organize my thoughts all the way to taking an online course, building my website, and beginning to work with clients! Courtney always supplies me with amazing tools when I need them, helps me get clear on my priorities, and encourages me to celebrate the small (and big) victories. She’s so clearly energized by her work and brings so much passion to the process!”
Katie Crouch, Copywriter + Owner, www.katiekcrouch.com

“What have I gained working with Courtney and the flourish coaching process and community? Here are some of the benefits: learning how to slow down and reflect. Meditation (before this program I had not meditated.) An introduction to labyrinths. Learning how to do vision boards (another thing I had seen but never created myself.) Giving myself permission to rest and be compassionate with myself. Learning to give myself permission to be OK with whatever is happening at any given moment. Through our work with the Enneagram I have a better understanding of my innate drivers and how they shape what I do, how I feel, and how I respond to situations.” 

Jennifer Miller, San Francisco, CA

What are we exploring together in this Garden Party?

Step One: Identify The Weeds in Your Inner Life AKA INNER FREEDOM WITH THE ENNEAGRAM. 

In month one we are going to really build the capacities of your compassionate Inner Observer and deepen with the Enneagram at every level. If you are new to this tool, I will help you identify your type and identify those key type-specific practices that are your next step to cultivate awareness and find relief from the particular habitual trance that goes with your personality type. If you have been working with the Enneagram for a while, I’ll be sharing some next level guidance and teaching to help you utilize this tool to bring more of your subconscious/habitual patterns up into consciousness so you can more easily able to make the changes and growth you desire.

(I have been studying and personally working with the Enneagram for a dozen years. There is no end to the Enneagram. It is one of my teachers for this lifetime. It is a guide you can trust. Wherever you are on your Ennea journey, I would love to help you live even more connected to the freedom this tool offers.)

In this first month I will be teaching the Enneagram in a whole new way, emphasizing the relationship of this personality pattern with nature, and specifically suggesting healing plant allies for each type and how to use them to both understand yourself and your needs, and resource yourself more wholly.

Garden metaphor 🌿 Invasive weeds grow in disturbed soil. They aren’t bad themselves, and in a way even serve a function in that they grow where nothing else can grow. But they have a tendency to take over. They hog the sunlight and crowd out the native plants thus creating and maintaining a disequilibrium in the eco-system. Similarly, your Ennea type habits and inner negative voices internalized from society serve a function. They are your ego trying to keep you safe. However, they choke your native goals from really being able to grow. The focus for this month is to get the inner voices/energetic Type habits from overwhelming or undermining your deeper desires for your life. As we identify and remove some of these voices/type habits then there will be more sunlight and breathing room for YOU and your hopes for your life to grow. {Also some weeds turn out to bring you medicine!}

Step Two: Nourish the Native Plants AKA FEEL MORE RESOURCED, CLEAR + RESILIENT

How do we have the fuel to keep weeding and nurturing this inner garden?

By helping you identify the voice of your Enneagram essence. This is where we learn to hear and give ourselves what we most need/desire/require. In this month we will be talking about diversifying your pleasure portfolio and I’ll share some really helpful teaching about the shadow side of pleasure including numbing and overdoing pleasure until it turns into pain. We will also talk about the best posture to adopt during growth, which helps keep you from tipping into overwhelm. (Good things, when they feel new or out of our comfort zone, can actually trip our stress response! So I’ll share strategies for expanding the good in your life in a gentle, sustainable way.)

Garden metaphor🌿 This month is about nourishing your native plants. Trust me this is FUN and helps you access untapped reservoirs of energy. 


This month is all about specific TOOLS that help us connect our inner life into our daily experience in real and concrete ways.  I am a resource to person matchmaker and I’ve got a big garden toolshed so I’ll be bringing forward the best tools for the specific small group of women in Garden Party. In addition, one set of tools we are going to focus on in this month are those that help us in the Life Garden of Time, including strategies for creating a flow and rhythm to your calendar so that you feel peaceful, like you are waking up and in the exact right space doing the right things, each day. 

Garden Metaphor 🌿 Gloves, sharp snippers, strong trowel and a pretty garden hat. All of these make a real difference in how easy it is to make progress in your garden. If you are working with outdated or old or rusty tools, it is going to make the process more arduous. With fresh tools we can really make progress toward your priorities, with more ease. 

You want to live connected to your heart/soul’s truth/essence but the translation into schedules can be really tricky. Especially because many of us live between two worlds:

A new paradigm which is rooted in creating relationships and systems that are more just, generative, and mutually beneficial.

And an old paradigm or approach to life which is rooted in extractive or “power over” practices, like companies extracting hours from employees and an economy that extracts from the earth, and entrepreneurs taking something from clients through pushy sales techniques or children in really tight educational systems or schedules. So all that stirs up the inner static.

The tools I’ll share this month help bridge the world from the inner life into REGULAR life and real world schedules, so you can have the experience of enjoying the fruits you have cultivated in your inner garden.

How all of this will be delivered:

🌿 Each month I will host one teaching class on that month’s theme, which will be recorded.

🌿 I will also create a written guide for you with notes, journaling prompts and resources.

🌿 Each month I will offer two drop in Q and A coaching/community calls. I think I’m calling these sessions “Champagne and Questions” and I hope they have the vibe of a garden party. You can send your questions ahead of time and these will also be recorded.

🌿 Each month I’ll also offer a green tip for bringing more Vitamin N or nature into everyday life.

🌿 The calls will be hosted on Fridays at 1PM Eastern. To start your weekend off on a buoyant note! 

🌿 We start gently on Monday May 17th with some reflection questions to seed our time together and our first call is Friday May 21.

Gentle, consistent support is one of the most powerful ways to nurture growth. That is true in “regular” life but even more true now given the intensity of the past year.

This coaching container is a great fit for women who want to go deeper with the Enneagram and other inner life tools that cultivate courage, resiliency, and clarity but who want to learn in a playful way.

I call this approach a “deep dive with a light touch!” 

You have two options for joining. Garden Party membership is $100/month for three months and includes everything I’ve described in this invitation page. {Space is limited to ensure an intimate learning community.}

You can also opt for Garden Party membership + Private Coaching. This includes an additional 60 minute private coaching call with me each month where I can make custom recommendations for based on your current goals and your Enneagram Type. This option also includes private support in between the private calls and group sessions, via email or voice note, because sometimes you just have a quick question or could use a dose of real-time encouragement. {Space for this option is limited to 3 people}

If you are feeling curious or drawn toward this coaching container and learning opportunity but not sure reach out to me at cp@courtneypinkerton.com and I can help you discern if it is the right fit for you.



“Through working with Courtney and deepening in my Enneagram journey I am no longer constantly exhausted by my inner critic’s running diatribe. Embracing kindness and compassion allowed me to tend and befriend this inner critic. Instead of constantly wrestling with an unceasing loop of negative self talk I am now able to embrace my inner resources and appreciate my strengths in a new light. This challenging inner work created capacity for me to tackle significant challenges in both my leadership at work and also my leadership of self in my personal life. One of my goals in my work with Courtney was to explore a new framework for change. Instead of the mentality of “before and after” when “before” represented everything that was wrong and “after” represents everything that is now fixed and right in my life I have discovered a new way to embrace change. By incorporating kindness in little ways on a daily basis I am able to open myself to significant change that can only happen by being kind to myself on a large scale. This includes seeking and embracing joy in new ways. In the past I struggled to find a way to incorporate regular physical exercise into my life. I heard the advice over and over again, “just find a form of exercise you love.” But I wasn’t able to ever find that on my own, so I relied on my friends to provide the motivation needed by making plans to work out together. Now, I am pleasantly surprised to be wrapping up my second year of hula dancing classes with a newfound love of exercise through dance. Learning to embrace kindness towards all parts of myself is leading me into a more sustainable and pleasurable way of life.”   

Sarah H.



Courtney Pinkerton is a certified life coach and the author of the Amazon bestseller, The Flourish Formula: An Overachiever’s Guide to Slowing Down & Accomplishing More. Courtney is an inner life coach and a lover and a teacher of the Enneagram. She has helped hundreds of conscious women pursue their most salient goals and discover more pleasure in the everyday. She has dual master’s degrees from Harvard Divinity School and Harvard Kennedy School, is a certified Wayfinder life coach and the creator of the flourish coaching method. After selling their house and all their belongings and spending a year adventuring in Nicaragua tutored by their neighbors in the art of slowing down and living more, Courtney and her husband and their three children now make their new home in a co-housing community in Asheville, North Carolina.