A woman I didn’t know came up to me at a conference last weekend.
“You’re Jessie May!” she said.
“Yeah,” I said smiling. “How do we know each other?
“We don’t. But I used to come to your events.” She paused. “I wanted to tell you how much I appreciate the way you always showed up so real and vulnerable.”
I stood there for a second. Because she didn’t even know how much I needed to hear that.
Meeting Lisa was synchronistic in so many ways. I’m so grateful for a new soul sister and can’t wait to see the magic that unfolds from this connection.
Since I started my first business in 2011, I’ve carried a story about myself that I come across as too put together and polished. For years, I told myself that my perfectionism gets in the way of people being able to relate and connect with me.
And to be fair, that story didn’t come from nowhere.
I grew up without very much money. And I was terrified of my friends finding me out. I mean terrified - like, I had literal nightmares about it. So I learned to look the part. I hung out with kids who had more than we did and I made myself look like I belonged. It was a survival mechanism to keep me safe.
On top of that, I took responsibility for other people’s mental health and happiness at a very young age. I was the emotional rock, the one who kept it together so the people around me could be ok. It was a lot of weight to carry into adulthood without realizing I was carrying it.
When I started my first business in 2011, I carried that fear of being “found out” and the need to be seen as “put together” with me into how I showed up for my community. I wanted to be seen as successful and responsible and the one who had all the right answers. I feared that if I didn’t, no one would respect or want to work with me and my business would fail. That I would fail. And I was determined to prove to myself and the world that I would create a different story than the one I’d been handed. But underneath the polished outer layer, my inside world was filled with self doubt and feelings of not enoughness.
Eventually I began to realize that it’s actually through vulnerability that we create connection and trust. This even became the foundational message in my personal branding business that I ran for 10+ years. The more of your truth you can bring into your brand, the more successful your business will be. The more you allow people to see you and know you, the more clients you’ll attract and greater impact you’ll be able to make.
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This made sense to me. I know it’s how I felt about other people and brands. I loved when I saw their messy, vulnerable sides. I felt more connection and more trust, and was more likely to work with them when I did.
And even though I was teaching this, it was a constant edge to show up that way myself. To be seen in my vulnerability was scary and there was still a part of me that believed I’d be rejected if I did.
But they say we teach what we need to learn. And so I gave myself constant opportunities to practice what I needed to learn the most. I challenged myself to share openly, to be vulnerable and to even let people see my messiness sometimes.
And then I closed that business and discovered there was a lot more here for me to unpack.
When perimenopause arrived it brought me face to face with the places that being the “put together perfectionist” were still getting in my way. All the places in my life where I was still holding it together unraveled fast. This was next-level falling apart, and I’m honestly glad that I gave myself the privacy to go through this without feeling like I had to make it relatable in my newsletter or social media.
While I didn’t share the depths of my process publicly, I did share my experience with a women’s medicine circle I was part of that held me and loved me through it. It was the most healing experience because finally, that part of me that still believed that if I really showed up in all of my mess, that I would surely lose connection got proven wrong. I completely fell apart and was loved even more.
And in a different way, Lisa, the woman I met at the conference gave me evidence of that too.
Another reminder that the story I’d been carrying about myself wasn’t the whole picture.
The truth is that there was a part of me that believed I had to hold it all together to be loved and respected. Those were survival strategies that came from my childhood experiences and nervous system trying to protect me the best way it knew how.
But what I’m realizing now is that even when I was still afraid of being fully seen, I was showing up in a way that could be felt. Enough that someone remembered it and came up to me 3 years later to tell me about it.
So instead of being critical of my past self for not being further along, I want to acknowledge her for doing better than I gave her credit for. She was doing better than she realized.
And maybe the gift that this healing journey has given me is the realization that love and connection have been available to me all along.
That we don’t have to be perfect and get everything right to still leave an impression.
And I’ll be honest with you, stepping into Alchemy & Ash is bringing up all of this again, that old fear of being seen before I’m ready and the part of me that still wants to have all the answers before I move forward.
Healing doesn’t mean we never have to look at the thing again. It just means we recognize it faster. And we have more choice about what we do with it.
Invitation to share:
Is there a story you’ve been carrying about yourself that might only be part of the picture?
Hey , I’m Jessie May!
At 39, perimenopause turned my life upside down and eventually became an awakening I never saw coming. Now I guide women through the whole arc of this initiation, from sitting in the void of not knowing what’s next, to finding our voices as we emerge into who we’re becoming.
I love creating spaces where we can talk about what this time feels like with people who understand. Thanks for being here, I can’t wait to get to know you!
Ways I can help
✨ Substack Coaching - For women who want to turn the experiences they’ve lived through into a meaningful Substack publication that helps others feel less alone.
✨ Perimenopause Initiation Coaching - For women waking up to themselves through the initiation of perimenopause.
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A space for women unraveling and recreating their lives during the perimenopause years. Pivots, purpose, identity, patterns and turning our experiences into meaningful work … those are just some of the things we explore together here.
Love this so much and can relate. I’ve started writing based upon the foundation of the stories we tell ourselves and how they shape our lives, until they don’t.
When you spoke of being 'found out', I felt that in my bones. I'm making a practice of leaning into vulnerability, and in doing so, each time it's a little bit easier. Fear is still present, sweaty palms, and a gnawing in my stomach. But I'm choosing not to read those as signs to constrict, but as opportunities to expand. Laid bare, I won't be for everyone, and that's ok. More than ok. It just means that ultimately I'll be surrounded by my authentic people.✨