Why 27 Feels So Weird
As Britney Spears once said "I'm not a girl, not yet a woman"
This week on my podcast, Define Normal, I posted a solo episode reflecting on what it feels like to be in your late 20s—a time when growth can feel exciting and terrifying. A friend’s text sparked the episode and sent me down memory lane to the year I turned 27.
I turned 27 in 2020. We were in a global pandemic, and I temporarily lived with my parents in the suburbs of Dayton, Ohio. I traded my adult life in Manhattan—where I went to the office, took workout classes with friends, attended happy hours, and lived alone in a one-bedroom apartment—for my lime-green childhood bedroom, where my mom asked who I was giggling with on FaceTime.
The pandemic likely heightened how strange it felt to be 27, but it also forced me into deep self-reflection. The life I loved was on pause. Suddenly, all that mattered was my and my family’s health.
By the time I emerged from my late 20s, my life had significantly changed. I quit my job at Meta, realizing I valued the friendships formed with colleagues and the in-office culture more than my role. Without the office environment, it was time to move on. I also discovered that, while I loved being close to my family after spending time in Dayton and Chicago, I wasn’t ready to settle down in the Midwest. So, I moved back to New York.
My annual “Should I Move Back to Chicago?” conversation still happens. It’s a recurring debate with myself. But I’m grateful I lived there for a few months—it solidified my decision to move elsewhere.
In this episode, I explore why 27 often feels like an emotional turning point. It’s an age when you begin asking bigger questions about your life: What do I value? Who do I want to be? What’s holding me back from getting there? I share what I learned during that transformative year and how it shaped my perspective on growth, transitions, and the pressure to “have it all figured out.”
The response to the episode has been incredible. Earlier today, a listener sent me her story about navigating 27. Her words felt so relatable that I couldn’t help but share them (with her permission, of course).
A Listener’s Story
“27 for me started on April 30, 2023. I had just returned from living with my mom for six weeks in Ohio, subletting my NYC apartment to save money and pay down the credit card debt I had quickly accumulated. That debt came from a whirlwind of going out, moving after a four-year relationship, and working remotely while living in different countries. I traded my apartment with other travelers to live in Switzerland and Canada.
This lifestyle shift was sparked by the realization that I had never taken a real break after graduation. I graduated early, packed up, moved to New York City within a week, and started my ‘big girl job’ three days later. Looking back, that quote about being ‘somewhere between a teenager and an adult’ perfectly describes how I felt at the time.
I spent part of 27 dating seriously—or at least trying to. I bent over backward for men who wouldn’t even make me a top-five priority. One, in particular, was sweet but too busy and private to give me the relationship I was looking for. I stayed in it longer than I should have because I felt I needed to be in a serious relationship. But he wasn’t the right person to start that journey with.
I also left my job to follow an old boss I admired, who promised to champion me at a large company. Suddenly, I was living in Manhattan but working in New Jersey—a strange divide between two worlds. In the city, I was living like a teenager: partying, blacking out occasionally, and embracing the chaos of ‘America’s playground.’ At work, I was surrounded by people with families, mortgages, and a sense of stability I couldn’t relate to. I felt stuck between two identities.
Towards the end of 27, I started to get sick of it. I was nearing 30, still blacking out occasionally, had a series of failed situationships, and was in a shitty financial place. I felt like I had failed. I started to force myself to look within. What did I want? What made me happy? What is stressing me out? What is sabotaging me from living the way I want to? The more layers I peeled back and the reflection I did, the more I realized it was my environment. I lived in New York City, a playground for billionaires, trust fund kids, and playboys. None of this was getting me where I wanted.
I began to inquire more about moving across the river. I grilled my coworkers on their favorite neighborhoods and took days to wander around the area and look at apartments to get a feel for it. I finally settled on moving to Jersey City. My apartment felt adult, and the people I met acted like adults. I was surrounding myself with what I wanted to be in hopes that it would help me progress to where I wanted to be.
While I am only 1 year out from 27, I know this was the right move. People close to me comment on how much lighter and happier I seem to be here, and I even notice a physical difference in my body (more snatched and less anxiety? Worth its weight in gold). While I’m nowhere near where I want to be, I sit comfortably, knowing I am in the right place to make the right moves towards that.
I have given myself an environment that reflects where I want to be at 90,40, and beyond here in Jersey. I think back to if I had stayed in Manhattan, and I would not have been able to say the same thing. So thanks, 27. You were a mess, but you gave me the gift of progress for years to come, and I can’t thank you enough.
Her story showcases some of the questions I was also asking at 27. That year forces you to confront discomfort—whether in your relationships, career, or environment—and use it as an opportunity for growth.
I'd love to hear your story if you’ve lived through 27 or are navigating it now. Drop it in the comments or DM me—I might feature it in a future post. And don’t forget to listen to the episode. Maybe it’ll remind you, as it did me, that growth is a process and taking your time is okay.
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