Everyone seems to be throwing me the question: “What have you been up to, Kaylie?”
I usually throw back an answer that feels alive for me in that moment, and framed in a way that would make sense to whoever is asking me. This isn’t intentional, and I’m trying to answer genuinely when asked. Yet it’s been an interesting process to bring awareness to how scattered my brain is when receiving this question, and it always sparks a moment of inner reflection. What am I doing?
The best answer I can give is actually quite simple: I’m learning how to be a human again. I’m focusing on constructing a life where I can better live to my values. And I’m using my intuition and the flow of life to bring me where I’m supposed to go.
Have no idea what that means? Well, it’s looked different every day. Let me dive deep into what it’s been like to be me the past couple of months.
I attended a Sleepawake Immersive
Sleepawake is a week-long emotional and relational wellness retreat. It focuses on the intelligence of our emotions and how to connect to our deepest sense of purpose. Basically everything needed to be a happy and healthy person.
The biggest thing I learned from this experience is that I don’t have to do it alone. In the past year or so, I’ve been doing a lot of self-development work. Solo-traveling, journalling, silent meditation retreats, reading self-help books, etc. While it’s been incredibly empowering and I’d do it all again if I could, it’s been quite lonely.
Of course you meet friends along the way as you dive deep into these experiences, and that is such a joyful thing. But the beautiful thing about the Sleepawake experience is that you are able to do incredible inner work with the support of those around you. You are in a space where all of your messy being is welcomed with a community to hug you through it.
The amount of love that was cultivated in a week hanging out with strangers was truly incredible. I was able to see and be seen in new dimensions, and it’s made it so much easier for me to connect with others.
I left the retreat with a new intention to bring more people along for my chaotic, messy, human experience. And hopes to open my heart for more people to bring me along theirs.
I quit my job at Duolingo
This felt like an impossible decision to make. It seemed as though I had everything I had ever wanted. A dream job in NYC with benefits galore and genuine work friends. It wasn’t until I cut ties that I could put to words why it needed to happen.
I started the job last fall with a lot of energy. I was expecting a similar experience to my internship, where I was being inspired to grow as an engineer and given opportunities for social impact in the education space. And I’m not saying this was no longer possible at the company. I just found it too difficult given the circumstances and pressure I experienced in my couple of months.
The team I was put on was the definition of ‘AI-first”. We were experimentally constructing a system to have LLMs generate a math course on the mobile application. It was a new team that worked fast, and there was a lot of movement within the team. Within the first month, my manager and mentor switched teams, and they had fired someone for not meeting expectations.
I was putting all my energy into a role that was entirely new to me and not receiving much help. I would reach out to teammates for support, and would be redirected to ask AI. The work I was given was small bugs that were often fixed by editing simple sentences in LLM prompts. So I was there, spending my entire workday struggling through the work no one else wanted to do and not talking to a single soul. Where is the humanity in that?
I fought hard to find meaning in the role. I tried to connect to the social impact work, but it was mostly based in Pittsburgh. I asked to be in more product discussions, but engineers weren’t invited to those meetings. I asked to switch into a PM role, and was thrown into these 1:1 meetings with other employees where they tried to convince me that I’m asking for too much.
The biggest problem I had was that I wasn’t growing towards where I want to be in the future. I want to be a leader. And it started to get clearer that it would take a lot of time to get there as a new grad at a corporate company with over 1,000 employees.
So I left.
I went to a Vipassana Retreat
Yes. I meditated in silence for 10 days. Again.
This was my second vipassana retreat, and it’s true that you have a different experience every time you do it. So many things come up in your consciousness when you are in silence for that long. It’s impossible to remember them all when you walk out. I’d say the big takeaways this time were to continue following my intuition, structure is nice, and I’m way more content with silence now. It’s actually quite enjoyable, when in the past it was severely uncomfortable.
I went into it this time with a slight craving that I would come out with clarity on next steps. And of course, I didn’t get a lot of that. Instead, I got validation to go out and try things without so much fear of failure. The idea that my next move must be perfect was leaving me anxious and doing nothing. I’m learning how to permission myself to shoot crazy long shots, and be okay if they miss.
The biggest highlight of the experience was on the 10th day, where I got to break the silence with my roommate. It’s arguably a crazy way to meet someone for the first time. Living with them in silence for over a week and then finally getting the opportunity to talk to each other. And it turned out to be one of those special miracles of connection, where souls feel connected. We stayed up all night talking about life, love, the pursuit of happiness, all of it. I laughed so hard as we shared our crazy life memories, and I teared up while hearing her story of incredible resilience. In no time at all, I developed so much love for this human named Aida.
I went to Love Burn
Love Burn is a 4-day camping festival in Miami, recognized as a regional Burning Man event. It’s a space of builders, artists, and volunteers who build incredible art installations and gather around themed camps offering music, workshops, and communal experiences.
I decided to go to this event the day it started. My friend Tim had an extra ticket, and called me asking if I wanted to join. At the time, I was in Tahoe on a ski trip with old coworkers. I took this as an opportunity to move on from my past, and start saying yes to new experiences.
So I booked the next flight to Miami.
With no time to set expectations, I was genuinely blown away. The community was so welcoming and giving. The art installations were incredible. And I got to dance my little heart away on the beach with my friend. What else can you ask for?
I helped produce the play LIFESTYLES
I worked as a production coordinator for the first showcase of the play LIFESTYLES (written and directed by Charlie Rinehart-Jones). It was a story of sharp tensions between friends in their late-twenties on a weekend trip in Alaska.
This being my first experience backstage at a show in New York, there was a lot to absorb. My role mostly involved running the light/sound board for the shows and being a helping hand for the production team as they brought the art piece to life.
It was such a joyful experience for me. The entire time, I felt immensely grateful to be working alongside such determined artists. The ambition of everyone involved was genuinely contagious.
I was most impressed by the amount of love and care put into showcasing a piece never been performed before. A writer had a dream, and incredible friends to help bring it to reality. It was spaces like this that ignited my love for humanity, and gave me permission to dream myself.
How I even got involved in this play in the first place was a beautiful story. A couple of months before, I had met a lovely girl named Sophia working at a flower shop. We got talking while she made me a bouquet, and I found out she was an actress. I was inspired and told her I would love to do that one day. One thing led to another, she called me looking for help on a play she was producing.
Ever since this interaction, I’ve been trying to talk to more strangers in the city. There are such beautiful souls out there, and you genuinely never know where a conversation might take you.
I’m volunteering at Three Jewels and homeless shelters
A struggle I’ve experienced since moving to NYC is feeling like I’m not doing enough to support those that need it most. I’m sharing a home with the richest of the rich and the poorest of the poor. It’s forcing me to reflect on what kind of community member I want to be while I live here.
It’s brought ease of mind to jump on opportunities to serve others. I’m currently volunteering as a barista at Three Jewels, a nonprofit aimed at providing access to yoga and meditation for everyone, regardless of their ability to pay. My passion for serving as a volunteer at Three Jewels continues to grow as I continue to experience the benefits myself. It’s my first meditation community that I’ve been able to connect with, and is filled with an incredible amount of compassionate souls with so much wisdom to share. Words don’t quite describe my love for this place.
I’m also volunteering at local soup kitchens that focus on providing meals, shelter, and clothing to those in need. And I keep $1 in my jacket pocket in the case I walk by someone who needs it.
I’m choosing to take some responsibility for the fact that not everyone has everything they need to flourish in this world. I care a lot, and I’m learning how to take action on that care.
I’m creating art
I believe the best artists are the ones who have lived crazy lives. They use art as a tool to express their most intimate moments with the world. So others can experience it with them.
I wish we all were creating more art. Using our creative outlets to share our human experience. Bringing more connection in a world full of loneliness.
So here I am, being the change I want to see. I’m writing on substack. I’m doodling in my free time. I’m mailing love letters to friends. I’m making up my own moves on the dance floor. I’m writing monologues and acting them out.
The biggest thing I've learned so far is to not take it so seriously. My perfectionism has been stopping me from making things and sharing them. It feels vulnerable in ways I'm not used to. But I'm experimenting, and slowly figuring out which forms speak to me most.
I’m choosing the path less taken
I’ve spent too long chasing what others have defined as success, making decisions out of fear, and slowly forgetting who I was.
I resist.
I’m done losing myself to a life that wasn’t mine.
I’m choosing to be alive and move from a place of love.
I’m in pursuit of being human. <3
