You are invited… to the Flourish Holiday Playshop!


Imagine feeling easeful, satisfied and nourished while you engage all the aspects of the holiday season:

🎁 gift-buying
🥧 family meals/gatherings (or not)
😷 navigating COVID challenges + choices
🎄holiday decorating
🕯spiritual practices
That is what the Playshop is all about! 
There is no one way to navigate the holidays* but forced cheer NEVER feels good.

The holidays are an opportunity to look lovingly at any inherited traditions, and give ourselves permission to claim what fits AND to shake things up and recreate what will best serve and nourish us now.

That kind of inner rummage sale is especially needed after all the changes and disruption of the last couple of years.

I am hosting a A Flourish Holiday Playshop on Friday Nov 19 and Sat Nov 20th at 1PM EST and it is going to be a GOOD time. You + me + 2 hours to dream/map/play with your holiday season, enrich your family culture, and nourish your inner life so you feel resourced and ready for the festivities.

Pay-from-the-heart pricing 💗 available and I’m planting a tree with Tree Sisters in honor of each Playshop participant! 🌳🌲🌳

The Playshop will be hosted over Zoom and includes LOTS of inner life resources plus a luscious written guide 📔 and journal prompts.

All the details are below! Space is limited so this is an intimate, small group experience. So please reserve your spot today. 
Warmly, Courtney

What is a Playshop?

A playshop is like a workshop, only fun.

Because y’all, we need some fun. The last few years have been a wild ride. Bringing a playful spirit to our yearning for joy and hope this holiday season will help us find it. 

We turned our living room upside down for a playshop photoshoot and had a really good time. My husband Rich was the photographer and my kids popped in and out making me laugh. I even opened a bottle of wine at 11AM because we thought it would be funny to put on my “holiday cocktail party” attire and pretend I was at one.

I am still wearing my cozy pants from Target on the bottom, which weren’t supposed to be in the shot! This picture for me captures the vibe of this unusual holiday season, as Covid restrictions relax for some of us and we try to find our way forward into new experiences (and remember how to wear something other than our home clothes!).

I invite you to nurture your holiday season with a little time and intention and join in the playshop fun, from my couch to yours. 

And feel free to wear your holiday fancies, on top at least! 🙂

What Your Flourish Holiday Playshop Journey Includes

Participation in a Flourish Holiday Playshop

Fresh teaching and tips to help you design your conscious holiday season so you enter this season feeling resourced and ready. 

My teaching will be recorded but the live small-group discussion and Q & A will not be — so that everyone feels encouraged to share what is on their hearts and minds. Choose whichever date works best for you, November 19th or 20th at 1PM EST. Playshop with be two hours with a short break. 

Newly-Designed Written Guide

Time and space to map out a gentle, supportive (even playful?) plan for you and your beloveds for the holidays and journal prompts to help you navigate the season and nurture your inner life.


I love gifts so I have curated several complementary resources to support your holiday planning and pleasure! 🎁🎁🎁

Navigating Holiday Gatherings + Family Relationships Using the Enneagram

This is a recording from a workshop I hosted last year on how to navigate relational challenges over the holiday season using the tool of the Enneagram to support yourself and to better understand your beloveds. I also answer some questions which came in about the holidays and grief, relationship frustration, and gift-giving.

Flourish Resource Library 📚 

Enjoy a curated digital library full of resources including mini teaching videos, guided meditations and written guides with journaling prompts. I’ve selected resources which will nourish you this holiday season and beyond, including excerpts from my Flourish coaching program on the Enneagram, meditation, and embodied practices which help you metabolize stress. I’m also tucking in additional resources to support your holiday traditions or help you design a new one, including how-to guides on creating a giving portfolio, a nature-infused advent wreath, and designing a solo retreat. 

*Navigating the Holidays

Let’s say a little something about the “holidays” or the time period covering late November through December and ending in the new year.

Depending on your culture and traditions, this time includes Winter Solstice, Christmas, Hannakah, Kwanzaa, Diwali and other holidays – or none at all.

Increasingly people are fed by more than one tradition or are holding different traditions in the same family. As for me, I call myself a “Buddheo-Christian.” I grew up Methodist, a protestant denomination, and have been meditating since I learned how at the Homeopathic Hospital in London during my year abroad. I weave both of these loves together in ways that delight me — think garden Buddha and Day of the Dead altar with all my favorite mystics. I love the Desert Mothers and Fathers of the Christian tradition, who may have had a hand in creating the Enneagram, and the liturgical year, with all its myriad feasts and fasts. And I love my husband who is trained in ecology and whose patron saint could probably best be described as Jane Goodall.

But beyond all these elements of my story is this: I LOVE holding space for people to examine what they belove and I am super comfortable with all the traditions or none at all. (This is why I went to Harvard Divinity school and studied alongside such a diverse crew. We laughingly said the only thing we could all agree on is sitting in silence).

It brings me a lot of joy to venture into these waters with you. And if you think some reflection on YOUR holiday season, whatever that means to you, could potentially be helpful or fun, I hope you will join me!

Warmly, Courtney

Pay-From-the-Heart Pricing 💗

I wanted to make this playshop as accessible as possible and to offer a discount for anyone affected by COVID or navigating other financial stress. There are three options. Click on the one below that resonates with your heart:

$127 Generosity Pricing       

$97 Gift-exchange Pricing      

$67 Support Pricing 

How this works:

Generosity price: helps me offer this playshop to more people, invest in my own learning and the growth of my business, and be generous with charitable gifts. 

Gift-exchange price: nourishes me and my family so that my coaching business is energetically sustainable and allows me to make charitable gifts.

Support price: available for anyone who needs more accessible pricing, especially because of COVID or other financial hardship. This price is also a way for new people to “taste” coaching at a lower investment, so it opens this healing work to more people.      

With EVERY purchase, no matter what price:

We are going to plant a tree in gratitude with TreeSisters. 

One of my favorite things about designing a new learning offer, like the playshop, is to link it with a charitable gift. As I reflected on the Holiday playshop I thought it would be meaningful to plant a tree with Tree Sisters for each participant. For those of us in the Christian tradition, bringing a tree indoors is one of the most central and potent expressions of the holiday season. (I love how wild it is! Coming inside with the hint of cool still between its branches. I feel such gratitude for the life of the tree.) Through making this donation we are actually going to be planting tropical trees, which sequester three times the carbon as deciduous trees. So we are really giving back into the earth to nourish and sustain her, as we are nourished by our holiday traditions. 

Questions? Read on. Or email me at

If I attending last year can I participate again? Absolutely! I’ll be bringing fresh teaching and the discussion is never the same twice. Plus the written guide will include new elements and we will plant more trees together! (You might even think of the Playshop as a holiday tradition to get you ready for your holiday traditions ;))

Will it be recorded? The teaching portion of the playshop will be recorded and provided for you in your digital library. The discussion and Q and A portion will NOT be recorded to create an atmosphere of ease and intimacy.

How will I access the resource library? After you register I’ll send you details with the Zoom link for the Playshop and the link for the resource library. It is housed in a program called Thinkific which you can easily access on your phone, tablet or computer. 

About Courtney Pinkerton, MDiv & MPP

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 Enneagram mentor. She helps conscious women (and a few amazing men!) to pursue their most salient creative, professional and personal dreams and to discover more pleasure in their everyday.

She has dual master’s degrees from Harvard Divinity School and Harvard Kennedy School, is a certified Wayfinder life coach and has been studying the Enneagram with master teachers for over a decade. After selling their house and all their belongings and spending a year 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 home in a co-housing community in Asheville, North Carolina.