You Were Never Meant to Fit In
I’d like to tell you about the time my son made Gingerbread Jesus.
It was a Catholic preschool open house around Christmastime. The room was full of adorable, festive gingerbread people made with googly eyes, yarn hair, red outfits scrawled in crayon. Adorable, classic four-year-old art. And then there was my son Will's contribution: a gingerbread man wearing the biggest frown you've ever seen, with dark red scribbles on both hands.
Confused and mortified, I asked Will why he made a sad gingerbread man. Will looked at me like I should have obviously known.
"Mommy, he's Gingerbread Jesus. He's nailed to the cross, and there is blood coming out of his hands. Wouldn't you be sad, too?"
I did not know whether to laugh, cry, or slowly back away from the bulletin board. What in the actual fuck?
The following year, my younger son Gavin's gingerbread person was a radiant, glitter-covered drag queen. Not kidding. So much glitter and hair and pizzazz.
Two years. Two gingerbread assignments. Two children who decided, completely independently, that fitting in was overrated.
At four years old they were already further along than I was in my thirties.
The ‘Should’ That Keeps You Small
Here's what I spent most of my life believing without ever consciously choosing to believe it:
"I should make others feel comfortable. I should fit in."
This is one of the sneakiest Sabotaging Shoulds of all, because it doesn't announce itself the way the others do. It doesn't scream loudly in your head like "don't disappoint anyone" or "put everyone else first." It operates more quietly, in the way you soften your opinion during a controversial conversation, laugh along with a joke that bothers you, or walk into a room and immediately start scanning for what version of yourself will be most acceptable.
For people pleasers, fitting in is a strategy and at some point, it worked. Being palatable, agreeable, and easy to be around kept you safe, kept the peace, or kept you feeling loved. So you learned it well.
Except the cost is huge. You sacrifice your authenticity, your actual self.
What My Kid Taught Me About Authenticity
Of my two children, my youngest has always had the most expansive way of being in the world. By three years old, he was begging for Barbies in Walmart and casually informing me that he had a boy's body and a girl's brain. And at preschool, he spent most of his time in the dress-up bin, twirling in tutus, and styling all the little girls hair.
I wish I could tell you that I immediately, instinctively, let him be completely free. The truth is messier than that.
There were plenty of mornings I asked Gavin to take off the sparkly princess dress before we left the house because I was worried about what other people would think (about him and my parenting). There were times I made him leave his Elsa dolls in the car when we went to the park. And small, daily moments where my fear of other people's discomfort outweighed my child's right to just be who he wanted to be.
I thought I was protecting him. I was actually teaching him that his authentic self needed to be hidden.
When he was four years old, I posted something honest on social media - a collage of him in all his glittery, feminine glory, with a caption that said he was happiest in dresses, hiked in headbands, and was brave enough to bring his My Little Pony to show and tell. When I hit publish, my chest tightened. I braced for judgment but I also felt like I needed to share a small piece of our truth and experiences.
What I got instead was grace. Comments from strangers who felt seen. A message from a high school friend (a sports-loving guy I never would have expected) who told me he'd read the post multiple times and gotten teary-eyed. Who admitted that before reading it, he would have taught his daughter to laugh at a kid like mine.
One honest post, but one moment of refusing to shrink or perform for comfort.
It opened a heart.
I get emotional every single time I re-tell that story because in sharing his truth, maybe just maybe, it made someone be a little more open-minded and accepting.
That's what authenticity does.
What This Has to Do With Your People-Pleasing
Your story is likely not my story. And I’m sure you do not have a gender non-conforming child. But I'd be willing to bet you know exactly what it feels like to hide a piece of yourself to make someone else more comfortable.
Maybe it's the spiritual beliefs you keep quiet at family gatherings. The career change you're afraid to announce. The relationship that isn't working, the boundaries you haven't set, the dream you've never said out loud because you're not sure people will understand.
But hiding your true self and living inauthentically is exhausting. It's a deeper fatigue than just being tired from working hard. It's the tiredness of constantly smoothing, softening, adjusting, and shrinking so that the version of you who shows up never requires anything from anyone.
Here's what I know: the world doesn't actually need the version of you that everyone is comfortable with.
It needs the actual you. The unique you. The authentic YOU.
What Is a Sabotaging Should? (A Note on This Series)
If this is your first time here, welcome😊 and let me give you a little context.
Confessions of a People Pleaser is my book about the beliefs and behaviors that quietly keep people pleasers stuck. Part memoir, part roadmap, it's organized around a framework I call The Sabotaging Shoulds, which are six deeply-held beliefs that most people pleasers have absorbed so completely they don't even recognize them as beliefs anymore. They just feel like their reality.
Each ‘Should’ sounds reasonable on the surface. But underneath, it's running a slow drain on your energy, your confidence, relationships, and your sense of self.
We've been exploring each one in this blog series:
Sabotaging Should #1: "I should put others' needs before my own" → Read it here
Sabotaging Should #2: "I should be happy all the time" → Read it here
Sabotaging Should #3 (this post): "I should make others feel comfortable. I should fit in."
You don't have to read them in order, but they build on each other. If one resonates, I'd start there.
Authenticity Is a Minute-by-Minute Practice
JFK once said that "conformity is the jailer of freedom and the enemy of growth." I think about that often when I think about Gavin, who before ten years old had already broken more barriers and opened more hearts than most people do in a lifetime - simply by insisting on being exactly who he was meant here to be.
Authenticity isn't a destination. It's not a bold announcement or a once-in-a-lifetime decision. It's the small, daily choice to stay true to yourself even when fitting in would be easier. t’s letting your gingerbread person be whoever they actually are, even if it's a little weird, a little bold, or a little more than some people were ready for.
The definition of authenticity is being true to your own personality, spirit, and character. That's it. Not performing. Not curating a version of yourself for external approval. It’s just being who you actually are, in all your messy, beautiful, unrepeatable magic.
If you needed the reminder: You are allowed to take up space! You are allowed to be someone people have to adjust to, rather than someone who constantly adjusts.
Questions for Your Journal
These come directly from Confessions of a People Pleaser:
What would my gingerbread person look like?
What did my family or culture teach me to believe about fitting in and being different?
Did I ever feel like I had to hide who I am to be accepted?
What kind of support do I need to be my authentic self?
Ready to Go Deeper?
My book, Confessions of a People Pleaser, walks you through all six Sabotaging Shoulds and gives you the tools to start breaking them down. You can find it on Amazon.
And if you're ready to do this work in a supported, one-on-one space, my Choose Yourself coaching program combines deep inner work with energy healing to help you get to the root of why you stay small — and finally, genuinely, start to live differently.
You were never meant to fit in. You were meant to show up fully.
And there's a profound difference.
Lisa Kern is a Reiki Master, transformational coach, and author of Confessions of a People Pleaser. She works with women who feel anxious, overwhelmed, and unfulfilled — helping them get to the root of why and reclaim themselves in the process. Find her at lisakern.com.