Episode 6: The Lore of The Broken Mirror
desire, broken mirrors and wanting something again
Every week I write about what’s happening in my life: love, work, identity, as I figure out how to be a real person, not just someone chasing the algorithm.
I thought I’d transcended desire, like I was above it. But this weekend at my friend’s 40th birthday, over truffle burgers, a guy touched my knee and I remembered what it felt like to want something. It wasn’t even sexual; it was just human. Like someone reminding me I still had skin. What if, after all my proclamations about not having sex with strangers, I just went crazy for a weekend? Of course, I’d tell you about it, but we’d have to actually be present for that.
The guy was charismatic, outgoing, and actually looked me in the eyes. Turns out I’ve been going for the wrong type this whole time. I don’t need the shy, confused guy lurking in the corner. I need the one who’s confident, talks to everyone, and shows up.
Someone asked me on Wednesday if my column was like Sex and the City. I said it’s more Mental Health in the City. In fact, there’s zero sex. But we remain hopeful.
How do you figure out what you want when you’re not in survival anymore?
I was crying in the empty bath on Friday. I always let the water drain and just lie there, staring at the white tiles. The water dries off my skin until tiny bubbles are left and then nothing, just the heat from where it used to be. The empty bath feels like the safest place I’ve ever been. It’s contained, clean, and quiet. The place I do most of my thinking.
This time, I kept thinking about who I want to step into the world as.
Cynthia says we’re always crying for a reason. There’s a story underneath it. Mine is frustration, the kind that says I’m ready for something new and have no idea what it is. That old narrative that I’m not enough because I’m still here, not somewhere else, not someone else. You know what’s going on work-wise. This column has helped me find my voice again, but I still wonder: what’s my show, what’s my impact, what am I trying to say to the world?
The mirror is the most expensive thing I own. An Ettore Sottsass mirror I fell in love with when everyone discovered Copenhagen style and couldn’t get enough of Pernille Teisbaek. I bought it after I made money in a live-video shopping app I started nine years ago. I told myself I needed to own one nice piece of art, so I bought this goddamn mirror. Two years later it broke. It’s been sitting broken ever since.
I realized how long it’s been since I actually thought about what I wanted. Survival doesn’t leave room for wanting. You just try to make it through the day without breaking more glass.
I’ll never forget when that money hit my bank account. I was in Austin, at a sushi restaurant with my friend Sarah. With a piece of ginger hanging from my chopsticks, I said, “I have negative seventy-five dollars in my account, and in an hour I’ll have a lot more than that.” I’d never made that kind of money before. Startup life is strange. You go into debt chasing something, and then one day you have it all. But what if that one day never comes? It’s funny that the art I chose is a reflection of me. Literally.
Every morning I wake up and see myself through fractured glass, catching flashes of the girl who used to chase everything, the one who thought a good outfit, a good kiss, a good business idea could change her life. I miss her naïveté and pink hair.


My epiphany is this: I haven’t fixed the mirror because I don’t know what I want to see in it yet.
They say it’s bad luck to keep a broken mirror. Maybe it is. But daily tasks like that have always been complicated for me. I can build a company from scratch, but I still forget to buy toothpaste.
In The Game of Life and How to Play It, Florence Scovel Shinn talks about people relying on “lucky monkeys” for prosperity and tells them to throw them away and turn back to faith. I know the mirror is supposed to be bad luck for seven years, but I like to think the universe is bigger than that. So I’m keeping it broken.
We’re living in a time of lucky monkeys: vision boards, manifestation coaches, ice baths, astrology charts, crystals. I do all of it. But deep down, I believe the one thing that actually moves us forward is sitting with ourselves in silence.
On Thursday I went to a founder dinner, the kind you’re supposed to feel proud to be invited to. The lighting was warm, the chicken was perfect, the kind of meal that makes you feel accomplished. All I could think was that I didn’t deserve to be there. I was surrounded by women who have figured it out. I know they’re probably going through it too, or have been through some form of “it”, but from the outside it all looks like a Pinterest board.


Lately I want to do something bad. Not ruin-my-life bad. Just live-a-little bad. Something that reminds me I’m not just a series of lessons learned. I’m actually alive. I haven’t figured out what that is yet, besides accidentally drinking too many martinis.
The mirror is so broken now that if you move it, I’m convinced a piece will fall out. I think I’m waiting for it to completely shatter, to scatter across my floor. Still, I catch myself looking at it, wondering if it broke when I did.
So I guess I’m trying to figure out what I want again. Wanting to be seen. Wanting to put myself out there. Owning my past without letting it define my future.
It’s getting colder in the city. The leaves are moving on, and so should I. Maybe it’s time to go on a date, preferably with someone who owns a toolbox
Somehow, Functioning
Jilly



I relate so much to everything you write! 🩷
Deeply relate to this. Thanks for sharing.