What makes a person who they are?
Is it the experiences they go through? The relationships in their life?
Or is it the astrology they’re born with, their Human design, or the soul that inhabits their body?
The past few years of my life have been a deep excavation into these questions.
When I was younger, in my 20s and 30s, I had this idea that by the time I reached 40, I’d have the mysteries of my life figured out. Like finally everything about why I am the way I am would finally make sense, tied off with a pretty little bow.
I had no idea what was coming.
No one told me that with perimenopause the questions would just get louder.
That perimenopause isn’t just a physical transition, but it’s an emotional and spiritual one too that brings all our unresolved shit to the surface to be looked at and sorted through.
And OMG have I been looking and sorting. Going into the depths of my psyche through medicine journeys, therapy, group work, solo travel, books and podcasts. I’ve really been digging.
For a while, the digging mostly brought up childhood wounds and stories around my parents, particularly my mom. I’ve been working through resentment, grief, frustration, loneliness and anger. And during this time I’ve been focused on what went wrong, how things weren’t fair and what I absorbed that wasn’t mine. It’s been a lot of untangling to figure out who I really am underneath it all.
And while the dots I’ve connected over the past few years have felt revelatory, bringing me peace and closure around some very hard things, something cracked open for me while I was writing this post that I want to share with you.
At first I thought I was just putting together a timeline of my life, but instead, creating this post uncovered a new layer of healing.
As I was looking through boxes of old family photos, so many memories came rushing back in. What I saw in the photos wasn’t pain, what I saw was a beautiful, free-spirited little girl with parents who loved her.
I had a good cry soaking in all the memories, really seeing and feeling how much my parents cherished me and created beautiful experiences for me.
I saw their humanity and the spark in their eyes when life was fresh and exciting. When they were still dreaming about what was possible and the life they wanted to build together.
For the first time in quite a while, I felt a softening around the memories I’ve been carrying. It’s not that the memories aren’t real, but what I was reminded of while looking at those photos, is that they aren’t the whole picture.
And so, going back to my questions at the beginning, what I believe, is that what makes a person who they are is a dance.
It’s a dance between their essence, spirit, soul, astrology or whatever we want to attribute it to and the experiences and people in their life.
It’s not nature OR nurture. It’s nature AND nurture.
Because a different person could have had the same parents, gone through the same experiences, and come away with a completely different collection of patterns and stories of their own to untangle.
The point of this post isn’t to analyze why I am the way I am (although you’ll see that my Gemini Moon sometimes couldn’t help herself).
It’s simply a timeline of some of the memories that have stayed with me over the past 42 years and contributed to shaping who I am today. And it’s the beginning of seeing them through a softer lens.
The very beginning
I was born off interstate 76, in the tiny town of Rootstown Ohio, on August 31st, 1983. It’s the kind of town you’d stop over to get gas on a road trip, but not think much of if you were just passing through. I was born at home on my grandma’s living room floor to my 24 year old mom and 26 year old dad who had gotten married (also in my grandma’s living room) a few months prior while my mom was pregnant with me.
My parents were hippies. For my first birthday, my mom made me a cake made out of beans and tofu frosting, decorated with grapes and raisins. YUM! LOL. My Ohio relatives thought we were weirdos.
For the first few years of my life, we lived at my grandma’s house.
I remember making lots of friends in the neighborhood. Those were the days when you’d show up at your friend’s door and ask “can so-and-so come out and play?”
I remember one day, me and my friends were visiting a neighbor lady who was handing out candy. She handed candy to all of my friends, and I turned around and ran home crying because I knew I wasn’t allowed to have any.
I was a fiery kid.
Which makes sense because beside being a Virgo Sun I have a bazillion fire signs in my chart. I threw tantrums a lot.
One day when my dad was driving me to preschool, I somehow escaped the car at a stop sign and started running down the street. He got out to chase after me and got the cops called on him because someone thought he was trying to kidnap me.
Another day when I was playing at a friend’s house, my mom was late to pick me up. I remember feeling terrified that she’d gotten abducted in a mall parking lot. I was literally sick over it. I imagined her being shoved into the trunk of a car and driven away into the woods where bad people were doing terrible things to her.
Well, none of that actually happened and she finally did come to pick me up, she was just late, which I would come to realize later in life was just how she rolled.
But looking back, I can’t help but think - why would a 5 year old even have that kind of thing in her head? After hours of excavating my deepest darkest shadows as an adult and turning over every rock of my childhood experience, I finally figured it out, but I’m going to save that story for a different post.
The first move
When I was 6 years old, my parents packed up our brown Ford pickup truck and moved us to Chestnut Ridge, New York where I started kindergarten at Green Meadow Waldorf School and my dad started teacher training to become a Waldorf teacher (which he never became, but I know the philosophy resonated deeply with him because he still references Rudolf Steiner to this day).
We lived in a Waldorf community called Threefold, that included the school, a teacher training institute, a home for the elderly, a local co-op, a farm, and many Waldorf-inspired homes, one of which we ended up living in for the next 4 years.
My childhood in New York was magical. Full of connection with nature, art, music, theater, seasonal fairs and festivals and a close circle of friends that felt like family.
I’m an only child, and when I wasn’t on play dates with friends, I would spend hours in the woods in our backyard, acting out solo performances for the fairies and gnomes.
But I always, always, longed for a brother or sister.
It was my biggest wish of all wishes and I would ask my mom and dad every day when I would get one. When I got older (after a brother or sister never came) I remember crying during movies with sibling story lines, always feeling an empty place in my heart where I wished a sibling would be.
A few more memories I have of that time …
The food
I’m realizing that I have a lot of food memories from my early childhood days. Ha!
My parents followed the macrobiotic diet and I remember sitting down to plates of steamed kale, acorn squash and quinoa (that we pronounced “quin-oah” until I discovered later in life that it’s actually pronounced “keen-wa”).
Although I’m grateful for the healthy food I was given, these meals were really hard for me to stomach as a little kid. I loved eating dinner at my friend’s houses because they would have “normal” food like macaroni casserole.
Becoming the responsible one
When I was in second grade, my mom went back to Ohio to live with my grandma for a few months … or was it years? I can’t remember how long it actually was. I just remember that she was struggling with her mental health and unresolved trauma that I didn’t find out about until she dropped me off at my college dorm 10 years later. During that time, it was just me and my dad.
My dad worked on the maintenance crew in our Waldorf neighborhood. I loved waking up early on snowy mornings with him to plough the streets. When we were out, we’d stop at the maple trees to collect sap from the buckets we set up weeks earlier. When we got home, we’d boil it down into the most delicious homemade maple syrup.
One day, my dad got really sick. He was so sick, he told me he needed to go to the emergency room. I was 8. But I figured it out. I called his friend and asked if he could come take my dad to the hospital.
My dad ended up being ok, but that’s just one small way that I became a responsible little kid.
Cleaning, cleaning, cleaning
As a little Virgo child, I didn’t like how messy our house was. I remember one day, inviting my friends over to play and standing in our kitchen, my face flushed with embarrassment at how the sink and countertops were piled high with dirty dishes.
Once I got old enough to stay home alone, I’d surprise my parents upon their return with a sparkling deep-cleaned kitchen I spent hours on. It felt so satisfying to my little Virgo soul and I felt like such a good daughter to be able to give this gift to my parents.
Yes, I became the ultimate good girl. But we’ll get to more about that in a moment.
The big move
When I was 9 years old my parents told me we were moving to Eugene, Oregon. So once again we packed up our brown Ford pickup truck and drove across the country. My parents didn’t have jobs set up or even a house for that matter, so we stayed in a tent in a campground for the first few weeks while they figured things out.
I was not happy. Not because of the tent. But because if you know anything about Waldorf school, you know that kids stay with the same class and teacher from 1st through 8th grade. My class had become like family to me and being stripped away from them was the hardest thing ever.
I started at a new Waldorf School in Eugene, but the school was a hot mess compared to the school I went to in New York. I was miserable. I desperately wanted to go back to New York and spent months planning my escape. Even if it meant running away and living with my friends. I was willing.
Eventually I did return. And it was great that I did because I realized life had moved on without me, and I didn’t really feel at home there anymore. It was sad. But it also freed me from the pain of my memories and allowed me to find happiness and be present in my life back in Eugene.
I quit going to that hot mess Waldorf school and homeschooled for a year before starting public school in 6th grade.
Middle and high school
Middle school was when the high-achieving good girl in me really started to shine.
On top of getting straight A’s, I rocked 1st base on the softball team, did my best to play basketball even though I’m only 5’2”, excelled at playing the cello and trumpet with solo performances in front of my band and orchestra, learned piano, competed in dance competitions, performed in theater and starred in a traveling production company.
In high school it continued, although I became more preoccupied with being “cool” so the cello and trumpet had to go, along with theater. But my inner “good girl” still found many outlets to do her thing. I sang in choir, was a peer group leader and sex educator, played volleyball, dated the star of the football team (lovingly called “Beast” by all his friends) and graduated earning my International Baccalaureate Degree.
But grades and extra curriculars aside, my inner good girl really took center stage when it came to the rules I created for myself: No drinking, no drugs, no sex (even though I had 3 different long term boyfriends).
And all for what?
As an adult through many years of therapy, I often asked, why? Why did I always feel the need to be so perfect and accomplished? To be so “good”? To always be responsible and do everything right?
Why didn’t I rebel like most teenagers do?
It’s not like I had super strict parents who pushed me to do more.
But for some reason, I set high standards and never questioned them. That is, until I was in my late 30s and I started questioning my entire life (but more on those discoveries another time because I did eventually figure out why - luckily we have lots of time and space on Substack to get to know each other!).
Oh, there’s one really big thing that I forgot to mention
My family didn’t have a lot of money. My dad was a carpenter and my mom cleaned houses for a living. And I was able to participate in all of the extra curriculars I did through scholarships and good old fashioned elbow grease from my parents (thank you mom and dad!).
We lived on the poor side of town across the railroad tracks, but I went to school with all the wealthy kids in the hills on the rich side of town. And I carried a lot of shame about that growing up.
Like literal nightmares about being “found out” kinda shame.
I remember dating a boy in 7th and 8th grade whose dad was a doctor and they lived in a fancy house on top of the hill across town. I dated him for two years. Two years!!! And I never let him see where I lived.
One night, I was watching a movie with him in his home theater and afterward, his mom offered to drive me home. All the blood left my face and my hands went cold. I panicked and thought of an excuse as fast as I could - that my mom was already doing errands nearby and needed to pick me up or something like that. Whatever I said, somehow I managed to get myself out of that situation.
I learned to hide the shameful parts of myself really young. I became responsible and put together making sure everything looked perfect on the outside so people would think I was cool and … I don’t know … worthy. That’s it. WORTHY.
Carrying my mom’s pain
When I was in 11th grade, I decided I wanted to go to college to become a therapist. Partly because I'd always been fascinated by why people are the way they are, but mostly because I wanted to help people live lives they felt good about.
My entire childhood I carried the weight of my mom’s regrets, unhealed trauma and cognitive differences, without even knowing that’s what I was carrying at the time.
Throughout childhood and most of my adult life (until literally last November 2025 when I went through a spiritual awakening and release) I made it my responsibility to make her happy. It never worked and I always felt like a failure.
I’m not going to get into all of those details here because I’m still figuring out how to share this part.
Let’s just say that my 20’s, 30’s and first couple years of my 40s were an unconscious reaction to “trying not to become my mom” while also trying to save her.
Leaving home
I moved to Boulder Colorado when I was 18 years old to study psychology at Naropa University - a Buddhist-inspired liberal arts school that integrated meditation and eastern philosophy into their education.
While I loved my education at Naropa, by the time I graduated, I didn’t want to be a therapist any more.
I didn’t want to wallow with people in their pain (no shade to therapy, I’ve literally done years of it myself and have gained a lot!). I wanted to help them achieve their goals and live lives they wouldn’t regret on their death beds.
That’s when I discovered this thing called life coaching. And I felt like I’d found the missing piece! I immediately enrolled in The Coaches Training Institute, got certified and started my business at 24 years old.
Business, marriage and the motherhood decision
For the next 15 years my business became my life. My purpose and identity were completely wrapped up in it, and not in a healthy way. You can read more about that story here and what happened to my identity when I finally let my business go in 2025.
After college I met my husband and spent at least 10 years agonizing over the decision whether or not to have kids. I say “agonizing” because it literally felt like agony.
I had so many fears and complicated feelings around the idea of becoming a mom. I couldn’t find clarity or peace or enjoy my life in the present moment for a very long time because the motherhood question was always looming over me.
When I was 39, I decided that it was time to get off the fence and finally decide, and that’s when I found out it was too late. You can read more about that story here and here, and how it sent me into the darkest void of my life that I’m just coming out of now at almost 43 years old.
So … that’s my life up to this point.
The long, yet oh so condensed version of who I am and where I’ve been.
As I’m writing this, I notice so many little pieces and stories that still want to come out, like …
how my marriage has been one of the greatest teachers of my life (and how did I marry someone who triggered the exact patterns I have with my mom and not realize it for the first 15 years!?) and …
how I, the ultimate Good Girl, found psychedelics when I was 39 and they changed my life (and no, they are not just for bad girls like I was trained to believe in the 90s, LOL), and …
how I developed a chronic pattern of second-guessing everything I say and do, how I finally figured out where it came from at 42 years old and what I’ve been doing to unwind it so I show up in my unfiltered truth, and …
SO MANY MORE.
One thing I know now that I didn’t know when I started writing this post is that our stories keep changing.
We remember new things and see old things differently.
I have a feeling there are still so many layers of my story waiting to unfold and I want to stay curious and open to seeing things in new ways (without abandoning myself in the process of course!) .
I want to share the unfolding with you and all of my stories, lessons and growth in hopes that something I say helps you feel a little less alone in this crazy adventure we call life.
And I’m reminding myself that we have time to go slow and really get to know each other. That’s what Substack is for. So yay!
If you’re new here (or even if you’re not) I’d love to get to know you in the comments.
Invitation to share:
Where are you writing from and what inspired you to start sharing your stories on Substack?
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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I appreciate your stories so much. And I got to really savor reading this one, which is a rare treat. This line got me big in the feels: "Let’s just say that my 20’s, 30’s and first couple years of my 40s were an unconscious reaction to “trying not to become my mom” while also trying to save her." That sums up my last 2 decades too. ❤️
I see so many parallels to my own upbringing. 1983, hippie mom, only and eldest daughter disguised as a middle child (between brothers), super strict with me, not with my brothers, caretaker, the one who figured it out, hyper vigilant to all emotions in the room, keep the peace, I can do it myself kid/adult that I am unlearning thanks to perimenopause. And my dad literally still says every time we say bye, “always be a good girl.”