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Joanna Douglas

I've spent years helping others navigate the gap between achievement and aliveness and right now, I'm navigating it myself. This newsletter is where that happens in real time: honest writing about the messy middle, the questions worth sitting with, and what it looks like to let life lead when certainty takes a leave of absence. If you're somewhere between who you were and who you're becoming, pull up a chair. Oh, yeah - I am an ICF Certified Coach, a Certified Enneagram Professional, focus on leadership development with a customized path to Emotional Intelligence through the wisdom of the Enneagram and I created the Depletion to Fulfillment framework.

A pair of eyeglasses with dark frames resting on a weathered stone ledge
Featured Post

Wanting what you have (and what the Dalai Lama actually meant)

Hello Reader, Welcome to the conversation. Some people's fulfillment looks like living in a cave on a mountain, meditating in silence all day long. Some people's looks like running a billion-dollar company, or a country. Some people's is a paid-off house and a quiet Tuesday. All of it can be true. All of it can be fulfillment. The only question that actually matters: is it yours, or is it someone else's definition you've been running on autopilot? “ Your time is limited, so don't waste it...

A skier jumping over a snow ramp against a bright sun and mountains

Hello Reader, Welcome to the conversation. The only skiing lesson I ever had was from my cousin, in the parking lot, before we got on the lift. She taught me the snowplow. You see, you point your skis inward, you slow yourself down. That was it. That was the whole curriculum. I didn't ask any follow-up questions. It didn't occur to me to wonder whether there was more I should know. She said that was all I needed, so I got on the chairlift with her and rode it up. What nobody taught me was how...

Pink and yellow plumeria flowers blooming with green leaves.

Hello Reader, Welcome to the conversation. There's a Hawaiian prayer that's been around for centuries. Its name alone tells you everything: Ho'oponopono. It means "to make right." The prayer has four phrases. I'm sorry. Please forgive me. Thank you. I love you. No elaborate ritual. No difficult conversation. Just four phrases spoken inward, to yourself, to the divine, to whatever you believe is listening. In the 1980s, a psychologist named Dr. Ihaleakala Hew Len worked at a psychiatric...

Colorful candles of different shapes arranged in a storage tray.

Hello Reader, Welcome to the conversation. A move from one state to another had been calling us for a while before we actually listened. When we finally said yes to it, the move came together with an ease that surprised us both, like the house already knew its work with us was done and was just waiting for us to catch up. We packed up seven years of a life, sometimes standing in a room wondering where a particular thing had even come from or how long it had been there, and somewhere in the...

A winding road curves through dry hills under sunlight.

Hello Reader, Welcome to the conversation. The Messy Middle, that stretch of change where the old is gone and the new hasn't arrived yet, has a particular cruelty to it. It doesn't just make the path unclear. It hands you a magnifying glass and points it directly at everything that hasn't happened yet. Every gap. Every delay. Every version of the dream that exists only in the future tense. And the longer you look, the tighter you hold. “ It's . — asdf From My Chair to Yours A couple of years...

A rabbit statue is decorated with tea cups.

Hello Reader, Welcome to the conversation. One pill makes you larger, and one pill makes you small. I heard this song recently, "Go Ask Alice," written by Grace Slick, which, according to the internet, is a riff on Lewis Carroll's Alice in Wonderland. A childhood story I'm sure you're familiar with. It's the one with a little girl named Alice who falls down a rabbit hole into a world with no map, no timeline, and no clear way through. A perpetually grinning Cheshire Cat. Flamingo golf clubs....

Woman carrying a suitcase walks away on a country road.

Hello Reader, Welcome to the conversation. In certain personal growth spaces, there's an unwritten agreement: when someone is doing deep work, someone else takes notes. Not because they're asked. Just because that's what you do when you're paying attention. I didn't think to ask before I sat down with my teacher at a recent retreat. I was present, I was in it, and it wasn't until I returned to my seat that I noticed the absence. No paper waiting, no handoff, nothing to help me hold what had...

Teacher standing in a classroom with students and colorful balloons.

Hello Reader, Welcome to the conversation. My preferred Enneagram school, the Chestnut Paes Enneagram Academy, is closing at the end of 2026. I heard it live. From them. At a retreat I almost didn't attend. And in the days since, I've been sitting with a feeling I don't have adequate words for. As it turns out, that is exactly what this newsletter is about. Beatrice Chestnut and Uranio Paes changed the trajectory of my life. My work, my relationships, how I show up in a room, how I understand...

Pink flowers are held in front of "love" sign.

Hello Reader, Welcome to the conversation. I forget sometimes that I am Ahh-Maze-Zing. There. I said it out loud. And I'm guessing I'm not the only one. We live in a world that is constantly offering us new metrics to measure ourselves against. Followers. Revenue. Title. The number on the scale. The square footage of the house. And somewhere in all that measuring, we lose track of something much more fundamental. Who we actually are. Not what we've built. Not what we've proven. Not what we've...

Woman reading a book titled "i am evolving"

Hello Reader, Welcome to the conversation. Somewhere along the way, we decided that verification meant approval. A blue checkmark. A credential. A title. A track record clean enough to display. We built entire identities around being confirmed: by institutions, by audiences, by algorithms that decided we were real enough to matter. And yet. LinkedIn created a verification system to fight fake profiles. The checkmarks appeared. The scams continued. CLEAR scans your iris at the airport to...