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It all started when I spent the summer as a camp counselor on an island west of Seattle. One of the core activities that I led was called a “solo hike” where kiddos would follow a trail of quotes alone. The kiddos would discuss the experience at the end and I was constantly blown away by the deeper conversations that quotes sparked—hearing third graders talk about gender stereotypes or fifth graders reflecting upon grief. I realized the power of quotes leading to deeper conversations—and that epiphany has grown into a business, a product and a mission: 365 Meaningful Conversations.

I’ll admit my love of quotes started from an early age: I’m an idealist at heart who loves how a quote wraps up lofty ideas into a concise structure. I’ll also admit that I’m an avid doodler. If you look at my notebooks from elementary school throughout college—you’ll find that doodles are the bulk of my notes.

woman drawing in a notebook

I didn’t start combining my two passions of quotes and doodling until I decided make my own set of quote cards—and little did I know, that would lead to hours hunched over drawing at coffee shops, buying hundreds of Sharpies, and scouring the Internet for quotes. Over two years, I accidentally drew 200 quote cards. I didn’t mean to, but I just kept finding quotes and wanting to bring them to life and once I’d drawn 200, I said, “Well, might as well make one for each day.” The final product: a box of 365 quote cards each hand illustrated with love.

I decided to take copies of my quote cards on the ultimate hiking test: a fifty day wilderness course. Each night, without fail, I’d pull out my quote cards and read them aloud. The conversations grew like the fire we sat beside and by the end of the trip I’d jotted down my own questions on the backs of each quote card. Suddenly, I’d created 365 quote cards with related questions—all by accident.

I started hauling my cards all over: coffee shops, into work, to family dinners…because I wanted to spark meaningful conversations. I hate small talk. I’m the type of person that when asked, “How are you?” I’ll actually respond with exactly how I am doing instead of the societally accepted, “Good! You?” Small talk frustrates me because it blockades the road to connecting with others.

group of people chatting

I started to realize that my meaningful conversation starting cards actually spark connection. When people are asked, “What’s the biggest mistake of your life?” you cannot help but feel connected after hearing a response. Why? People being vulnerable is the key to connection. As my hero, Brene Brown, says, “Staying vulnerable is a risk we have to take if we want to experience connection.”

And let me tell you: sharing vulnerably is a scary risk. It’s a palms-sweating, heart-booming kind of risk. Why? Sharing vulnerably means showing up just as you are—without wearing a mask to cover up your imperfections or messy parts. I can speak from experience that the moments before are scary, but as soon as you’ve tapped into vulnerability, the gift is feeling completely seen and heard.

Let me give you the most salient example in my life of sharing vulnerably. I was sexually assaulted before going to college and no one knew that part of me—I felt shameful, embarrassed and uncomfortable about that messy part of myself, so I let my experience sit in silence. Four years later, (long before the #metoo movement) I decided to speak out. My campus was in uproar about sexual assault and I wanted to give a face to a statistic being thrown around, 1 in 5 women. So, I wrote an article for my college newspaper. I slept maybe twenty-minutes the night before it was published as my mind spun-out thinking, “I’m so weak for sharing this part of myself…no one will understand it…”

meaningful conversations cards

My world was flipped upside down the next morning. My inbox and phone was filled with people commending my bravery and courage, confiding in me about their experiences with sexual trauma, and thanking me. The messages brought me to tears in an instant. I felt seen, heard, and accepted. The lesson I was given that day: the path to connection requires vulnerability, which requires courage. Courage to show up just as you are.

I’ve now sparked a mission with my box of 365 Meaningful Conversation cards: to create spaces for people to share vulnerably. I host a weekly group called “Meaningful Conversations” through a website called MeetUp in Boulder, CO. Each week a group of around 20 strangers show up at a coffee shop, we gather around a table, and take turns sharing our answers to the meaningful conversation starters. The event is supposed to run 7pm till 9pm, but we easily stay until closing time because connection is something people crave deeply.

It all started with a bunch of elementary school kids following a path of quotes through the forest—and it’s grown into a movement to cut the small talk, be vulnerable, and connect deeply, because that’s what we all crave as humans.


audrey phillipsAbout Audrey Phillips
I’m Audrey Phillips born in Seattle, WA and living in Boulder, CO. I studied Geology & Education at Bowdoin College in Maine and have worked as a wilderness guide since graduating in 2016. I am the founder of 365 Meaningful Conversations and enjoy having deep conversations, running & backpacking long distances, and eating ice cream on sunny days. 
You can buy my box of 365 Meaningful Conversations: https://365meaningfulconversations.com/purchase/