#65: you make the rules, f*ckers
the story behind CANDID and the importance of creative constraints
If you are new here, hi and welcome!! A lot of you are here from the generous recommendation of my dear friend, Maddy of
, so I wanted to take a minute to introduce myself and make sure this newsletter is a good fit for you. I started Caught Up in Char’s Web a couple years ago with the intention of writing one newsletter per week for 52 weeks. I shared them with only my closest friends and family for a good while before getting comfortable extending the invite outwards and I now love having new people here. So let me tell you a bit about my brain and writing…In 2023, I started an event series called Reading Rhythms with a couple of friends. What started as a small gathering on our rooftops in which everyone invited a few new people and brought whatever book they were reading at the time, turned into a viral event series that took us to the Today Show, New York Times, Daily Post, London Times, Rolling Stones, and beyond. The format of the event is 30 mins of silent reading with live music - a 15 min one-on-one in which you are encouraged to talk to someone you’ve never met, using your book as an ice breaker - 30 more mins of reading with music and then a facilitated group discussion with 10-12 people at the end around the WIDE variety of material everyone came with.
There was nothing more exciting to me than getting to sit around at the end and somehow find a connection between an erotic fantasy novel, a corporate finance textbook, and a book of poems. I And that’s what I intend to do here at Char’s Web. I write sporadically about the connections that I see between otherwise disparate things and tie them into a story that hopefully finds its resonance with you or someone you love. Here are a few examples:
#63: what does it mean to be ready?
#60: writing a new os: an evolution of control
If that sounds entertaining to you, welcome!! I am so excited to have you here. And if not, absolutely no worries - freedom is one of my core values. Unsubscribe button is below!
It’s been a few months since I’ve posted on here - between moving back to LA, the loss of my stepdad, my car getting totaled while parked in front of my house in the middle of the night, and the wildfires absolutely devastating the place that me and so many others grew up in, I have not had the time or bandwidth to write. But that is not what this is about!
This is a post that I am very excited to share about the origin story of CANDID - a deck of playing cards and conversation starters - that my boyfriend and I created out of the love and adventures we found in NYC. My intention in sharing this with you is to connect you to the invigorating feeling of getting to know new people or those that you already love with more playfulness, intimacy, and freedom.
Here it goes!
Above is an audio recording of me reading this post for those who prefer listening. Thank you, Philipp Kaspar, for the intro music!
A rat scurried across the subway platform, and without missing a beat, John turned to me and asked, "How did your hamsters die?"
My eyes bulged and my hamsters turned in their small graves. How the hell did he know I had such a story to tell about this? In that moment, standing there waiting for the L train, something clicked. Here was someone who knew exactly how to crack open a conversation – not with small talk about the weather, not with commentary about NYC's rat population, but with a question so specific and yet so universal that it could only lead to intimate storytelling.
This is what I'd been searching for when I moved to NYC – these moments of pure, unfiltered connection that make you feel like your world just got bigger. The kind of connection that reminds you of being a kid playing SIMS, where the only limit was your imagination and the stories you chose to tell.
I grew up building virtual worlds in games like SIMS, Webkinz, and Club Penguin. My favorite game to play IRL was “house” in which we all played different family members - I was always the mom. I also vividly remember a day in kindergarten where we simulated different jobs - ie bank teller, postman, grocery clerk, etc. - and got to role play these real adult-life characters that felt like a far cry from the contrived world of school that we were living in. There was nothing more satisfying than creating characters, making them fall in love, watching them have digital babies, buying virtual puffles, and escaping the confining box of turning in pieces of paper to receive grades that had no tangible merit in the world besides getting you into more prestigious schools in which you continued to turn in more pieces of fabricated paper. From a young age, I gravitated towards the games that gave me the freedom to shape reality however I wanted.
But somewhere along the way, I forgot about these early childhood experiences that made me feel alive and found myself feeling stuck, like I was playing more constraining card games where your sense of humor is limited by the cards in your hand – by someone else's creativity, someone else's rules.
As it happens though, the inertia of playing the wrong games eventually kicked up enough shit in my world to force me to look beyond and I spontaneously decided to move to NYC. Suddenly, I was playing a different kind of game entirely.
This was a game in which public transportation made me feel more autonomous, in which the city itself better-mimicked the games I played growing up - each corner representing more choice, more possibility, greater surface area for spontaneity. But what really changed wasn’t the place – it was the players. The people I met shared this infectious way of viewing life as one big creative experiment. They were constantly optimizing for fun, for novelty, for committing to the bit, for synchronicity, and the electric feeling that accompanies an internal knowing that you will look back on the moment you are experiencing in real time with the fondness and nostalgia that you watch your parents feel when telling stories about their memories of growing up.
Take the Sunday I decided I wanted a better way to consume news. I was exhausted by the pervasive, fear-mongering headlines and the increasingly blurry line between what is real and contrived. So I had this idea: what if I made a ritual out of getting a physical newspaper every Sunday and reading it slowly at a local diner? When I mentioned it to John, he didn't just nod politely – he immediately leveled it up. "Let's do it this weekend," he said. "And let's leave our phones at home, write down the directions on a scrap of paper, grab a newspaper from a bodega along the way, and meet there at noon.”
That's how I found myself walking through Bushwick alone, genuinely alone, without my usual armor of headphones and the reassuring weight of my phone. Six bodegas and one Daily Mail later (not exactly the New York Times, but hey, it was paper), I pushed open the door to Tina's Place feeling like I was on some kind of urban scavenger hunt.
When John walked in a few minutes after me, we shared this look of pure euphoria – like kids who'd successfully pulled off a heist. We ordered blueberry banana pancakes, hash browns, and orange juice and barely touched the newspapers. Instead, we spent hours trading stories about our childhoods, discovering the magical thing that happens when you put creative constraints around otherwise normal plans: everything becomes an adventure.
This became our thing – turning everyday moments into games. That's how our shared Apple Note called "Good Questions" was born. Each notification of – "John Lifrieri edited 'Good Questions'" – excreted a type of dopamine reminiscent to when my mom would say we could pick up a new Webkinz a the post office after school on a random Tuesday, alongside a Tiger’s Milk bar and a strawberry banana smoothie. Each question added to the list became our way of making anyone feel instantly part of the game. No prerequisites for belonging, just an invitation to share – like that moment with the hamster stories on the subway platform.
“Good Questions” not only made me excited to get to know new people in NYC but they also made me eager to discover more about the people that I’d known and loved for my whole life. It’s easy to take the people closest to us for granted, assuming we know their every waking thought because we’ve known them forever. Until you bring a new friend home and listen to their questions and suddenly you’re learning things about your own parents that you never thought to ask. It’s an astounding feeling, which is why having this whole new list of questions that I could spring on my lifelong friends and family excited me deeply.
The list of “Good Questions” kept evolving and so did my relationship with John. After a year of being best friends, novelty-seekers, adventure-creators, and co-founders of Silly Goose Enterprises, we also became lovers. One of my favorite stories to-date, and a newsletter for another time.
Somewhere along the way, we found ourselves in the South of France, having the type of conversation that feels like a cutscene in a video game – the kind where your whole world shifts slightly on its axis and you understand the present moment with the type of clarity that is usually only felt in hindsight. We were talking about the paths we'd chosen that allowed for so much freedom and spontaneity in our lives. And just like we'd committed to the bit of bringing newspapers to diners and eating blueberry pancakes on Sunday mornings, we committed to turning our growing list of questions into something tangible.
That's how CANDID was born – a deck of playing cards in a vintage tin, each one an invitation to the kind of conversations that make you feel seen. In John's eyes, I've never felt more like myself – more playful, intelligent, creative, beautiful, vulnerable, free. He has this gift of wanting to know you without an agenda. He listens. He seeks to understand. He asks great questions. He mirrors back to you the version of yourself that you are most excited to be in every moment. And always grants freedom and grace to change your mind.
And that's really what this is all about. CANDID, like life, is a game with no rules. The quality of your experience depends entirely on who you're playing with and how willing you are to make up your own creative constraints. Some people will trap you in tutorial mode, keeping you stuck in old versions of yourself. Others will invite you to level up, to explore new territories, to remember who you were when the world felt full of possibility.
I watched the movie In and Of Itself recently and there's this moment that captures exactly what I'm trying to say. I’ll spare the details to keep spoilers at bay and instead encourage you to watch it. But the gist is that when we decide who we are in a moment and how we want to be seen, and then someone mirrors it back to us, it feels real. It feels material. It feels like you are being seen as the person that you have always known yourself to be.
That's what happened that summer in NYC. The coexistence of freedom and intimacy created this environment where creativity abounded and empowerment was no longer a scarce resource. You know when someone looks at you a certain way and it immediately makes you feel more confident? It emboldens you to say the thing you'd usually hold back or take the joke just a little bit further? That was pervasive that summer.
And so CANDID became not just a deck of cards, but an invitation to that feeling. A reminder that just like the best games have no rules, the quality of your life depends entirely on the people you're playing with – and how willing you all are to make each moment special.
Char’s Web Song of the Week
Recipes of the Week:
Coconut chicken curry - adapted from Nyssa’s Kitchen recipe
Fudgy pumpkin brownies - adapted from Whole Hanna’s recipe
Xandra’s Curation Corner
Xandra Beverlin is an incredible art curator at Pace Gallery, co-founder of PULSE, and dear friend, who so generously pulls pieces for this newsletter each week. I text her a few short bullets about the main themes of Char’s Web and she replies with the most thoughtful articulations of the artists that come to mind. This is my favorite part of writing my newsletter. Do yourself the favor of reading her curator’s notes!
This letter is partially about the origins of CANDID, but more so about creativity found in the mundane — all under the gentle guise of self-expression. That said, CANDID is in fact a game, and when I think about that, it leads me to modes of strategy and winning, which somehow drives me to repetition, and then lastly, uniquely, to patterns.
Nathalie du Pasquier is an artist who has always found a way to revolutionize patterns: as a way to delineate structure, but also as a mechanism to design a space within a composition. As one of the founders of the Milan-based Memphis Group, she worked with her contemporaries to design not just paintings, but also furniture, lighting, fabrics, carpets, ceramics, and glass. The shapes are proudly asymmetrical, the colors are boldly abstract, and the work itself somehow manages to completely reconstitute how someone thinks of an object that may have been normally looked over. In a sense, I think that’s so much of what Charlotte is getting at here as well, the integration of creative constraints as a type of
“life” practice, even something as simple as reading a newspaper in a bodega, or walking there without phones.
In a world this inundating, tumultuous, and occasionally harrowing as the entry to 2025 has been for many, it seems to be increasingly difficult to set aside time specifically to be systematically creative. Perhaps our way out of this rut is by taking a note from the artists of the Memphis Group and encouraging each other to reimagine the banality of daily life: through poignant questions, recreated activities, and the thoughtful design of the things we see everyday…
— Xandra Beverlin
All past issues of Char’s Web are available for reading here. A few samples below…
#1: A first of many.
love the back story of Candid :) makes me love the cards even more!! and always love your insights and poetic way of sharing with us xx
Smiled the whole way through this! <3