Why Flourish?

At our core, we all want to show up and make our mark in this beautiful world.


But in the process, we often lose our equilibrium and end up eating ourselves on the inside to contribute “out there.”

We long for more time. More space. More clarity.

To be shown what is ours uniquely to do.

To gift ourselves guilt-free time to recharge and renew. To relax the internal pressure. To feel our own “enoughness” – not as an intellectual idea but as a homecoming in our bodies. To laugh more. To feel present to the people and places we love.

To feel so wholly satisfied in who we are and what we are doing that we lay down the habit of comparing and despairing.

To no longer feel like we are “missing” our right life. Living one lane over from the fullness that is our birthright.

Showing up and making fierce, brave, creative contributions in our communities or work lives and savoring the beauty and humble pleasures of the everyday.

Creating a life that fits us. Not too small. Not too big. Just right.

I See You


Somewhere along the way, you started to believe that it wasn’t safe to stop trying so hard. Or to trust yourself – especially your authentic desires and longings, which can seem silly or superficial to your inner task master. I know the struggle well because I have been there.

Hi I am Courtney

I created the Flourish coaching program because it’s possible to live a life in which you lay down the habit of compartmentalizing and instead feel like you get to show up with your whole, authentic self in every space: work, home and anywhere you feel called to go. I created the Flourish Formula coaching methodology to teach women how to make peace with that part of you that is never satisfied. I’m taking over a decade of professional, academic, and deep personal exploration and making it available to you wherever you live.


If we’re just meeting for the first time, here’s what I want you to know about me and my work:


warrior pose

  • I have long been fascinated by the question of how our inner life shapes our work in the world and spent four years studying the intersection of spirituality and leadership/social entrepreneurship at Harvard, earning dual master’s degrees from the Divinity and Kennedy Schools.
  • I am a certified Life Coach through Martha Beck’s renowned coach training program. (She is a Master, Oprah’s life coach and as fun live as she is in her books.) I am also a certified holistic life coach and have studied the Enneagram extensively from numerous teachers, especially in the Narrative Enneagram Community. I have a special interest in how our personality type is expressed somatically, or in our bodies.
  • I’ve hosted transformative retreats at beautiful venues in the United States and internationally to help women find ease and satisfaction in their personal and professional lives.
  • I am a recovering overachiever who totally knows the pain of getting caught in what I call “the gold-star economy” and pushing and striving your way through life.
  • I believe women living satisfied and spacious lives is a form of leadership with powerful ripple effects that help to create a better world. The kind of world I want for myself and for all of our children.


the Flourish Forumla Program


“Like receiving a massage for your whole life.”

The Flourish Formula program was the reset I truly craved for my mind, body and spirit. It guided me back to a more calming and centered state in which my entire self needed so badly. My outlook and energy are more aligned and in sync. Plus, this was so ENJOYABLE. Each week I could feel my soul crave the new material and excited to put everything into practice even when it was hard at times.
The impact for me personally was extremely high. I can honestly say when I wrapped up the Flourish Formula program, my ROI more than doubled. The content provided specific practices for me to experiment with that aligned with my stress areas. The overall effect was so soothing! I felt like I had received a massage after each call or each time I read a chapter from the book!

—Julie Alison, Dallas, Texas

“One of the best gifts I have ever given myself.”

—Karen Cameron, Quilter + Non-Profit Leader
Katie Wise

“Flourish Formula Coaching Program is life-changing”

As I am reading and soaking in what I learned in your book and program and tweaking my daily life and imagining my Flourish calendar and seeing myself in my Enneagram type and the neglected side of it and having epiphanies….it’s all because YOU WROTE THIS BOOK! This program is awesome, life giving, life changing. And the strange part of that is, in a weird way, it doesn’t seem new or novel or beginner in anyway- it feel ancient… In a sense it seems like it’s been here in the world and it’s a resource that one can build on AS A BASE for a really fulfilling life and THAT is what is so amazing- the flow and the guidance and the language and the care- it is solid like a big sequoia tree. It’s just so integrated and complete that it’s hard to believe you just did this! I don’t know if my words are saying how truly impressed I am by the love and care in which you share your gifts with all of us, and how talented you are at what you do.

—Katie Wise, Martha Beck trained life coach, Chicago Illinois
Katie Crouch

“Coaching with Courtney is a wonderful investment.”

Courtney is natural at integrating so many tools that you can simply relax into the process. It all just flows! I am so grateful that I got connected to her. Coaching with Courtney works and is a wonderful investment in yourself. I’m doing EVERYTHING I set out to do when I started coaching with her: meditating daily, writing/reading daily, exercising 3x/week (including running, yoga, and weight training), getting tons of sleep, taking on little creative projects here and there, and enjoying my work. Lots of plans coming up and feeling content for now. Thank you!!

—Katie Crouch, Writer/Editor, Chicago Illinois

“Coaching with Courtney reduces overwhelm and creates calm”

I feel calmer. I keep thinking through the statement from a couple of times ago: ‘I’m not here to grind through promotions.’ And I remember the first time we talked I was just completely overwhelmed with life. I’m busy right now, have a lot of stuff to do, and am tired from a lot of travel but I don’t feel overwhelmed now. Those are the lessons I’m really hoping to hold onto. I don’t need to grind through life so hard, I don’t need to be so busy, I need calm and quiet. And how can I feel brave, balanced, and boundless? What are my action plans for those?


“Courtney helped me find more happiness + healing.”

Upon completing my coaching experience with Courtney, I am ready to dive into my life again with the confidence I needed to discover within myself. It has been an incredible journey with her and we’ve discussed everything from meditation to life cycles to essential oils to nature therapy. After a year of experiencing trauma and painful relationships, this was the perfect time to search inwards for the answers I had been looking for. She’s been a gift in my life, and I’m so proud of myself for working so hard with her towards happiness and healing.

—Rachel, International Program Administrator at LIU Global

“Coaching with Courtney left me happier + more grounded.”

Coaching with Courtney is like taking a class about You. You find out things you like, and things You don’t like – about yourself, about the world around you, about patterns that You get stuck in. It has been wonderful to talk to someone smart, caring, & thoughtful to work through things, as it is not always so easy from the inside to see how you are stuck. As a result of our coaching sessions I feel more in control of my life. When stressful things happen I now have a very practical toolkit of what to do that works for me. I have also been happier and more grounded. Meditation has been an unexpected and awesome bonus.

—Liena, Publisher, Brooklyn NY

“Courtney makes self-awareness a habit.”

Now I feel better. It is easier to wake up in a better mood. I used to frequently go to bed with a hurt on my heart and now I can process it, with meditation. It is easy to be a snowball rolling down hill. Now I can stop. I recognize when I am spiraling, or being too overbearing and I can push the pause button. These months working together have made self-awareness a habit that I will carry with me into the rest of my life.

—Amy, Urban Farmer, Dallas, Texas
Amy Acosta

“The Flourish Program was a life-changing intervention for me.”

On a personal level, talking about my Enneagram type and working through the guilt and shame I have carried for a long time was a life-changing intervention for me. I still go to that hard place, but I find myself kicking my shoes of, grounding myself, and searching for the beauty within. It has actually been a spiritual change for me. One of surrender and understanding.


“A life coach with a Harvard education and achievement path I can relate to”

I’m a huge fan of yours because your story/delivery/persona are a great fit for me. I’m a bit of an achievement-snob for lack of a better term so a life coach with a Harvard education and achievement path I can relate to is a better fit than someone who for example never left the town she grew up in, was a stay at home mom right out of school, etc. I will reiterate it is SO important in my opinion you are religion-neutral so that both religious and non-religious people can benefit. You do this super well.



  • Custom coaching support with Courtney and a course page of flourishing materials including audio/video mini-modules and written guides which teach powerful mindset and mindbody tools.
  • Guidance in moving consciously through your change process: You are not crazy, you are just growing! Old or stale relationships, concepts of yourself and ways of working may need to shift or fall away to make space for the new.
  • Clarity about next steps (especially in terms of relationships, career and creative choices) and support in taking them.
  • The Creation of your Flourish Formula, a unique template or internal support structure which allows you to step into the next level of your life with confidence and ease.
Program Components


An signed print copy of my book The Flourish Formula


Eight audio modules (one for each step of the FLOURISH process) broken into 10 and 15 minute sections so you can listen on the go at your convenience

written guides

Written guides and deepening questions to help you implement the lessons in your everyday life


One on one coaching calls with Courtney to help you get out of any stuck places right away. These calls are a potent combination of support, encouragement, targeted resources and loving accountability. They help you take inspired action, one step at a time. You also have access to Courtney in between calls via email  so you can reach out with a specific question or challenge or to celebrate! 

figure out the box you are in

F – Figure Out the Box You Are In

This is the foundation of our work together. Without knowing those inner marching orders that keep the pressure high inside you, we cannot begin to form new habits. The Enneagram, an ancient personality map, is the most incisive tool I have discovered for getting clear on your core motivations and most frequent stumbling blocks. There are nine distinct personalities, three of which lead with their head center of intelligence, three which lead with their hearts and three which lead with their gut or body intuition. The Enneagram doesn’t put you in a box. It shows you the box that you are already in.

learn to have a love affair with your work

L – Learn to Have a Love Affair With Your Work

What if your relationship with work was more like a supportive relationship rather than an exhausting to-do list that never seems to shrink? In this step, I help you identify your “original medicine,” those unique qualities and contributions that you are here to share. I also help you release old iterations of yourself or goals that no longer fit, so that you can make space for the priorities which resonate for you in this season of life. If you struggle with work envy (when you find yourself perennially feeling small in the face of others’ accomplishments) I can definitely help you release that habit and build a deep and abiding sense of trust and care for yourself and excitement for your work and/or creative offerings.

overcome your gremlins

O – Overcome Your Gremlins

Gremlins are the playful term I use to describe the inner voices which make you criticize or doubt yourself or which sabotage the growth or changes you truly desire. Based on your Enneagram type you likely struggle with a certain set of inner demons which I can help you heal and integrate. Often just “seeing” the voices for what they are — the ego trying to protect you — can precipitate a powerful shift. Together we help you find growing freedom from gremlins.

understand the language of your body

U – Understand the Language of Your Body

You have to be able to count on your body to support you in accomplishing what you are here to do and you need energy and resiliency to thrive in all aspects of your life. Do you find yourself continuously crashing once a big project or event is done?Or depleted and frustrated by body breakdowns, which keep you from reaching your goals or moving at the pace that you desire?  Every body is distinct. (Something called bio-individualism.) Together we will craft a plan to decode your unique bio needs and to help you take exquisite care of yourself, from food which nourishes you deeply to and movement you enjoy. I can also share with you several easy, DIY methods for keeping the stress in your life and body at a manageable level, as well as help you identify who to recruit to be on your health/wellness team.

reset with meditation

R – Reset With Meditation

This step offers several easy meditation techniques that you can use to reset whenever the pressure builds. Unable to quiet your mind? You have come to the right place! In this step, I unpack some of the most common roadblocks to starting your own meditation practice and introduce a range of meditation options to help you discover one that fits you perfectly in this season of your life.

immerse yourself when stress builds

I – Immerse Yourself When Stress Builds

This step gives you a moment to catch your breath. It is not about introducing a new tool. It is an invitation to resource yourself with a fresh practice the next time you can’t sleep or shut off the hamster wheel in your mind. (Remember step O? Those gremlins get louder when you are growing.) In this chapter, I describe nine centering practices, each of which corresponds with the Enneagram personality of the same number and has been designed to unravel some of the constriction felt by that particular type. However, all of these practices are helpful for anyone to use at any time. While we all have one home base of our personality type, we also experience the whole range of emotions and human struggles. Think of these practices like a menu you can choose from the next time nothing else seems to be working.

schedule your flourish calendar

S – Schedule Your Flourish Calendar

This is where we bring it all together. Imagine waking up feeling present, calm and at peace – and moving through your day, confident that you are focusing on the right things at the right times instead of feeling guilty or distracted. This step is your opportunity to customize a life and schedule that support you rather than the other way around. To do this we need elegant scaffolding: a greenhouse for those tender and beautiful shoots that want to grow in your personal, creative and work lives. This is how we nurture and ultimately share your greatest contributions: The Flourish Calendar. I’ll show you step-by-step how to create your own custom Flourish Schedule.

hold it lightly

H – Hold It Lightly

The way we hold these tools or practices is as important as what we do. If we make personal growth or our goals for our life another metric for evaluating ourselves (and setting ourselves up for failure), we end up adding stress rather than removing it. Hold it lightly reminds you that resiliency lies not in getting it perfect but in your willingness to stretch toward the changes you desire and to begin again.



I’m all about experiential treats. I can tell you everything, because what fun would that be? But I love sharing gifts with clients. 
retreatA beautiful written guide to help you design a custom private retreat for yourself. In this guide, I talk about how to choose a location and prepare your mindset as well as what to pack in terms of clothes, books, and other supplies, plus tips on how to easily prepare nourishing food. It can be a little intimidating to set off on your own for a solo/silent retreat but it doesn’t need to be. Use this guide to get started and to create an experience that renews you deeply: body, mind and spirit.


Courtney Pinkerton
If you are looking for a quick fix or a coach who will collude with your inner task master to force you into new habits or let you hide or slip under the radar, I don’t recommend we work together. You will be disappointed.

However, if you are ready for a significant change in how you live your life (a shift which both opens you up more to daily pleasures and helps extract your most potent gifts), a coach who is both gentle and effective (and who holds you to your highest intentions for this life) plus encourages you to be more brave and compassionate than you ever thought you could be… let’s do it!

The right support can be like a greenhouse for your dreams — protecting them when they are tender shoots and fast-tracking their growth.

The Enneagram and the other Flourish coaching tools are like nutrients in the soil of this new life you are growing. 

I have been a student of the inner life for two decades, and a coach for almost ten years. I have invested tens of thousands of dollars into my own learning. Growth is my thing. I love working one on one and customizing these mindset and mind-body tools and framework to help your create lasting changes in your life.



Have a question about this program? Wondering if it is a good fit for you? The best next step is to book a free half hour call. This will give you a free taste of coaching and an opportunity for us to connect. I get to hear more of your story and share more details about the program and together we discern if it is a good fit. You can book your free flourish coaching call here. Or reach out to team@courtneypinkerton.com with questions and we will get back to you.

What about the cost? Coaching is a financial investment. This is not a generic program but rather a supportive, high-touch relationship to guide you through your own transformational process and the best resources I have discovered to make your growth more comfortable, easier and {hopefully} faster.

Fit really matters in coaching, so a one on one call is the easiest way for each of us to discern if we could work well together. But please know that I am not into pressurized sales conversations. So on our call if I think I could help with your current challenges or goals, I’ll share more details and talk through the price and payment options and answer any questions. My coaching calendar remains fairly full but if I am not taking new clients I will let you know that too and we can decide if you would like to be on the waitlist. I’ll also recommend any other resources or referrals I think could help. 

I love my work and the women (and few inspired men) I coach and would love to connect. I wish we were taught all of these awareness tools and practices (like the Enneagram) in bite-size pieces from grade school on up. But most of us come to recognize the need for a change through the challenges and pains of life. The flourish coaching process is really an inner life or soul curriculum and it can open the door to feeling so much lighter, more satisfied and happy in your life. It is inner work but I think none of us can do it all by ourselves. Or maybe we could but it is so much harder and takes a lot longer.

Flourishing is never a solitary sport. You living fully is a huge gift to those around you. I would love to be on your support team. Let’s do it! #flourishtogether

xo Courtney