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I just spent the past few hours, untangling the last 8 years of my business from Kajabi - the platform I used to run everything from my email list to my website, to my checkout pages, my membership and of course, all of my courses.
I’m not sure how I’m feeling right now.
It’s a mix between …
“WOW, you created A LOT”
“You should be proud”
“Look how consistent you were!”
“What amazing value you offered!”
“You really knew your stuff!”
“Look how pretty your hair was”
And …
“Just imagine what you could have created if you actually finished what you started?”
“Gosh, you really over complicated things.”
“Ugh, gag, why did you have to act so rehearsed in your videos?”
“Who would want to watch these?”
“No wonder your business failed, you were so caught up in getting everything perfect that it took you literally YEARS to finish anything.”
Have you ever quit something before it was finished?
Have you ever stayed in a business, a marriage, or something else, long after the voice inside told you it was time to let it go?
Afterall you already invested so much time, money or energy that you couldn’t possibly stop now! Sound familiar?
If you have, or you’re currently in that space, wondering if you can really let the thing go, this post is for you.
And if you have a friend who needs to hear this, please share this post with her. I want as many people as possible to feel less alone as they let go of the thing they thought they couldn’t.
What I’d like to say to that voice now, the one telling me I failed because I let my business go, is this: I hear you, but it depends on how you look at it.
Was hosting over 700 in-person gatherings in Colorado since 2011 a failure?
Were the beautiful connections and life-long friendships that came from the community I built a failure?
Was helping women with big hearts and big dreams create 7-figure brands a failure?
Was supporting hundreds of entrepreneurs in getting to the truth of who they were so they could express that clearly and connect with the people they were meant to serve a failure?
I spent 17 years … 17 years!!! Dedicated to my business. It was my whole life. And I was really, really good at it.
Until perimenopause arrived, catching me completely by surprise and unraveling everything I knew about myself, my work and my life.
At first the symptoms showed up in my business as burn out. The hours and energy I was putting into my done-for-you branding projects with one-on-one clients just wasn’t sustainable.
Sure, I was selling 5-figure packages with the whole shebang - branding, website, copy, coaching, etc. but by the time the project was done, and I paid my team and I clocked all my hours, the time for money exchange just didn’t make sense. I literally had no time for my personal life because I gave all my free time to helping my clients bring their visions to life.
And they had AMAZING visions! I was deeply honored to help them bring their visions to life. When we finished, their brands and websites were out of this world BEAUTIFUL.
Not only that, but the vision we created was built on a deep clarifying process that connected my clients with their truest, most magnetic voice so they could grow businesses that felt deeply aligned and fulfilling. My process was freakin’ awesome and I was proud of the level of detail, depth and quality I brought to my work.
And … I was exhausted.
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The beginning of letting go
I remember being on a walk with my husband one day when I shared the truth I didn’t want to see: I couldn’t go on like this. I was proud of what I created. But I was burned out.
We decided that I would step back from the one-on-one client work (my main source of income) and he would support us financially while I reinvisioned how I wanted my business to look.
That was just the beginning.
Over the next three years everything unraveled. My sense of self, my direction in life, what used to bring me purpose … it all slowly came apart. You can read more about that part of my story here and here.
My patterns and conditioning began to surface, requiring my attention to heal and I went deep into a void. During this time I lost all desire to show up for my business the way I used to.
But nonetheless, I hung on for dear life, because shutting my business down completely after 17 years would have led to a full blown identity crisis.
So instead, I decided to change my business model to something I hoped would be more sustainable.
I’d always loved archetypes and had used them as a tool in branding with my clients for many years. But now, I decided I wanted to create an entire body of work out of them that would allow my business to scale.
So over this time I pulled back from content creation and client work, and together with my amazing team, I worked on creating my branding with archetypes system. Complete with 12 comprehensive Canva brand bundles that included everything someone would need to build a beautiful and professional-looking brand, based on their archetype.
This project took me 3 years to complete. And that was just finishing the brand bundles. That didn’t even include creating the trainings that needed to go with the brand bundles so people would know how to use them and the 12 email funnels that needed to go with the quiz, and the sales pages for each brand bundle, and … 😅
It was a lot.
Ignoring my inner voice
Throughout this time, I remember a little voice in my head would sometimes whisper, “what if we just stopped?” “Do we really have to keep doing this?”
And another little voice would chime in “I want to use my healing to support women in a different capacity … beyond branding and logos … the deep inner work… can we do that instead?”
And the controlling part of me that was running the show would say “shhhhhh! Stop talking. We can’t give up now. Do you even know how many hundreds of hours and thousands of dollars we’ve already invested into this project?”
Not only had I spent the last 3 years creating my branding with archetypes system, but I also spent the last year paying a copywriter, brand photographer and website designer for a complete rebrand.
So I pushed through.
And at the end of 2024 everything was ready to launch. I sent an email announcing my new direction, and then … everything inside me said “nope”.
The final surrender
I was terrified. I didn’t know what to do with that message after investing so much into what I thought my purpose would be in this next chapter.
I reached out to a past client who is a psychic for some advice. She’d become a dear friend so I felt comfortable sharing my predicament with her. She suggested I take two months off to stop forcing clarity and pushing action (very old patterns for me). At first I thought, “Absolutely not. I’ve shown up consistently for my community for 17 years, I can’t just disappear for two months.”
But then… I couldn’t not disappear.
It was like a switch flipped. Something in me just turned off, and I physically, mentally, emotionally and spiritually could not make myself engage with my business.
Inspiration, motivation, drive, direction … it all went away.
Two months became three… then six… then a year.
The first couple of months were really dark as my purpose and identity that had been so wrapped up in my business began to crumble.
But as time moved on, 2025 became the most magical year of my life. A year that connected the dots of my life and gave me answers to questions I’d been searching for forever.
I don’t believe I would have found these answers if I didn’t surrender and create the space that life demanded of me, for them to rise to the surface.
There’s so much I want to share with you about that year, and I’ll share it all in future posts.
But for now, here’s where I’m at:
2025 changed me on a cellular level
I shed old stories, identities, patterns and ways of being that had gotten in my way my entire life.
The way I show up now is more rooted in Self energy and less driven by fear. I’m more at peace and more present with myself and others.
I have so much more capacity now for depth, truth, and the full spectrum of human emotions. To hold more of who I am… and more of who you are. I’m so excited to be connecting with you from this place.
And that little voice, the one that whispered, “can we share our journey through the unraveling so others don’t feel so alone?” I held space for that voice throughout 2025.
I didn’t rush to do something about it, but I just held space and noticed that it didn’t go anywhere.
Re-emergence
By early 2026, creative energy and inspiration started to flow back in until it was like a rushing river that I couldn’t ignore.
But the energy wasn’t flowing toward my branding business or the archetype system I created.
It was flowing toward Alchemy & Ash, a name and idea that came to me 13 months earlier and had been patiently waiting for me to be ready.
And now, here I am.
Half way through 2026, sharing my stories on Substack about perimenopause and the identity unraveling and awakening that came with it. I’m passionate about bringing these stories into the light, so you, if you’re experiencing something similar, don’t have to carry what you’re going through in isolation or shame.
What I’m finding through sharing my stories, is that MANY of us are going through something similar.
It feels SO GOOD to be on this path. So aligned with the next evolution of who I was put on this planet to become. And none of it would be possible if I didn’t surrender and let go of my previous business.
The lesson I had to learn the hard way is that sometimes, most of the time, we have to let go FIRST. Before the next thing is clear. That’s the scary part.
But what I’ve discovered is that surrendering into the void, and sitting in the unknown is actually where the magic lives.
When we have the courage to let go, there’s finally a crack for the truth that’s been trying to reach us to get through.
The perimenopause years have a natural way of asking us to evaluate our life and let go of anything that doesn’t align with who we’re becoming in this next chapter.
So now I’m curious...
What are you still holding onto because you’ve already invested so much into it?
Maybe it is a business or career? Or it could even be a relationship, a dream or a version of yourself that no longer makes sense?
I’d love to hear your story in the comments.
More posts on letting go through the initiation of perimenopause
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.
Subscribe to Alchemy & Ash
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.
I feel like yes this is so common for women as they move into midlife. I share about this too, because no one has talked about it so we go into this, hold tight to the narrative we’ve been taught, feel ashamed, confused and broken when we can’t make it fit anymore. Because as women we aren’t gathering like we need to, we aren’t sharing the stories. I’m determined to share them so the next women know what to expect and perhaps are prepared far better than I was.
Keep sharing!!! And thank you for sharing in such a real vulnerable way.
I really relate to what you shared here. I’m six years into my own purpose-driven business and in a slightly different version of that questioning right now—reevaluating what I want to create, how I want to earn a living, and whether those two things even need to come from the same place. I’ve been noticing how easily the financial pressure, brain fog and exhaustion can start stealing energy away from my creativity and vision, and I don’t want everything I feel called to create to immediately have to become something I sell.
I really liked what you wrote about letting go before you knew what was next. I think there’s so much pressure to have the next plan ready before we loosen our grip on the old one. Reading how much came alive for you once you actually gave yourself that space makes me want to hear more. Please keep writing about it.