Sinclair: What’s your three word bio?

Jillian: Bringing people together

You speak about the loneliness problem in America. What led you to start talking about it?

Jillian: I was really lonely when I moved to NYC. I was working in my apartment, living with roommates who I didn’t have vulnerable conversations with, and my biggest community was within the New York comedy scene. While I love improv and sketch, those crowds are really into making jokes and out-funnying each other. As a result, I was hungry for deeper connection.

One of my biggest turning points was Camp Grounded, a digital detox summer camp for adults. It blew my mind how close I could get to a group of people in 3 days. Looking back, I think it was because the organizers did an amazing job of creating a space that allowed for playfulness, vulnerability, and authentic connection.

After that, I became kind of obsessed with finding spaces where folks were excited to go deep and make new friends. I wanted to share them with the world! That’s how the newsletter started.

Sinclair: What advice would you give the 20-something or 30-something who’s moved to a new town and is desperately seeking to make connections, but doesn’t know where to start?


  1. Find people who are connectors: You know, the people who are genuinely excited to help others find their crew. They will plug you into the right community. Bonus points if you can find some of these people before you move. They’ll make your transition around 42% easier.
  2. Be a gatherer: I hear in NYC all the time, “People are too busy. They won’t come to an event if I invite them.” That’s bullshit! There are SO many people who are waiting to be invited. Even if they can’t go, or are too anxious to attend, they will be so thankful that you thought of them and reached out.

I think that a lot of people are too passive in their social lives. And I get it. The fear of being rejected can prevent us from reaching out. Yet, I’m a firm believer in what Adam “Smiley” Poswolsky, a Camp Grounded counselor, said in a memorial piece to its founder on Medium:

“Some people spend their time living, some people spend their time creating the world they actually want to live in.”

Sinclair: What responses have you had from followers of The Joy List?

Jillian: The responses to The Joy List have completely affirmed my desire to keep the newsletter running. I hear stories all the time like, “I’ve been living in New York City for 4 years. I don’t have a real friend group. I had no idea where to go to connect with people. This newsletter really helped me do that.”

Because I’m “The Joy List woman,” people feel comfortable telling me about their experience with loneliness. I wish everyone could have the blessing of hearing these stories. I genuinely think it would help folks realize that the majority of people feel disconnected in one way or another, and reaching out is the only way to fix that.


“Sometimes I feel guilty for taking time for myself, rather than doing work or “accomplishing” something. But that’s just the patriarchy talking. I deserve to learn as much about myself as I can, because it’s the only relationship I have that is permanent.” – Jillian Richardson


Sinclair: You co-founded NYC Community Builders. Tell us more about this group and its formation.

Jillian: I have a pattern that sometimes leaves me over-committed: If I’m looking for a community, and I can’t find it… I start it. That’s what happened with NYC Community Builders. I was looking for mentorship and companionship in the gathering space. There aren’t that many of us, and I had a gut feeling that we’d be able to help each other a ton if we just got in the same room.

We’ve had two events, one about event planning basics and one about difficult conversations. We also have a Facebook group for people who live in NYC and already run a community, or are looking for help with starting one.

I run the series with Joe Che and Timothy Phillips, the founders of Lightning Society, and Jenn Louie, the founder of Kinvite.

Sinclair: How would a close friend describe you on your best day?

Jillian: “Jillian leads by example. She wants the world to be filled with vulnerable leadership, genuine connection, and people fiercely supporting each other. So that’s how she lives her life. Also, her hair looks really great today.”

Sinclair; On your worst day?

Jillian: Jesus, Jillian is doing eight million things. No wonder she’s so stressed out all the time! That woman really needs to master the art of saying ‘no.’ She’s overcommitted, and her stress levels are affecting the people around her. Also, her hair is poofy as hell.”

Sinclair: What is something we often get wrong when talking about connecting with others?

Jillian: Events are not about lifting up the organizer. They’re about putting the needs and wants of everyone else first. They’re about making the audience feel special, and like their time was valued.

Sinclair: What’s something you wish you could say to your 21-year-old self?

Jillian: “Read The Heroine’s Journey. You’re way too in your masculine. Focus less on achieving, and more on getting to know and love yourself.”

“I create the world that I want to see.” – Jillian Richardson

Sinclair: What’s something you’re working to unlearn?

Jillian: Two big things right now! One, I am learning how to move more comfortably in my body. I didn’t grow up playing sports or dancing. It’s taking a lot of active effort to move with joy, and feel in my body rather than in my head.

The other is to take more time to learn about myself–– to reflect, meditate, journal. Sometimes I feel guilty for taking time for myself, rather than doing work or “accomplishing” something. But that’s just the patriarchy talking. I deserve to learn as much about myself as I can, because it’s the only relationship I have that is permanent.


“There are SO many people who are waiting to be invited. Even if they can’t go, or are too anxious to attend, they will be so thankful that you thought of them and reached out.” – Jillian Richardson


Sinclair: Who do you go to when you’re needing support and guidance?

Jillian: My roommates are a huge source of support for me. They’re totally there on my quest for self-love, and the constant freakouts on my journey into community-building leadership. I am also so grateful to Personal Development Nerds, Medi Club, and The Get Down.

The Joy List community has also been super helpful. I try and share something vulnerable in the intro every week. People always respond to show their support.

Sinclair: What’s one challenge you face in your work that you’re still working on navigating?

Jillian: Saying no. I love getting coffee with anyone and everyone. I have the mindset of, “You never know who’s going to be a person who could totally change your life!” Yet at the same time, I need to take charge of my schedule and prioritize my goals and my mental health first.

Sinclair: When was the last time you practiced self-care? What did you do?

Jillian: I take at least an hour for myself every morning. I write a poem, list what I’m grateful for, write my affirmations, and do a loving-kindness meditation. It’s my sacred space.

Sinclair: What’s something that’s been bringing you joy lately?

Jillian: Talking about the concept of ‘health at every size’ with my roommate, Gaby!

Sinclair: What’s something that’s been pissing you off lately?

Jillian: Diet culture and how deeply it’s lodged into my brain.

Sinclair: When was a time that self-doubt was at its worst for you while on your career and life journey?

Jillian: I was losing my shit when I graduated from college and moved to NYC. I was applying for TV writing jobs and not getting anything. I started applying for jobs that I didn’t even want, just so that I could have something.

When I finally made the decision to do freelance writing full-time, I was filled with doubt. I didn’t know anyone who was a freelancer! I had no community. I just knew it was the only skill that I could confidently get paid for.


Sinclair: What are your unshakable values?


  • Gathering people is sacred
  • Time for myself is non-negotiable
  • I create the world that I want to see
  • Most of the world’s problems stem from a feeling of disconnection

Sinclair: Who are a few amazing people that we should follow and why?


  • Tasha Blank of The Get Down for her badass DJ sets and her ability to create an inclusive dance floor where people get wild while totally sober
  • Lightning Society for being an amazing community hub in Bushwick
  • Jesse Israel of Medi Club and The Big Quiet for his ability to bring mindfulness to the masses
  • Devin Person for being NYC’s #1 wizard
  • Kerri Kelly of CTZNWELL for helping folks take care, organize, and actively protect our people and planet.

Sinclair: What is one piece of advice you’d give to someone struggling with self-doubt and feeling like giving up on their dreams?

Jillian: Read the biography of someone you respect. They failed epically, I promise.

Sinclair: It’s years in the future. You’re on stage to accept an award for your life’s work. What’s your five word acceptance speech?

Jillian: “My community shaped me.”

Sinclair: Imagine that all your life’s work disappeared and you only had 1 minute to tell the world what you truly believe to be true. What would you say?

Jillian: Prioritize human connection over everything else. People deserve to feel respected, appreciated, and loved. If you do that for others, it will return tenfold.


Jillian Richardson is the founder of The Joy List, a weekly newsletter which features events that New Yorkers can go to by themselves and leave with a new friend. She’s also the co-founder of NYC Community Builders, and the author of an upcoming book about the most powerful ways to create connection.

Learn more about Jillian and connect: Instagram | Twitter | Website

Learn more about the Joy List: Instagram | Twitter | Website

Featured awesomeness: Jillian says, “Subscribe to The Joy List here.If you’re feeling really generous, contribute to the Patreon or make a one-time donation.”



This post contains affiliate links. 🎁



Published by Sinclair P Ceasar III

Sinclair Ceasar is a speaker, podcaster, and higher ed professional committed to helping people live a better story, and be more hopeful. He sends weekly inspirational emails to over 1K readers each Monday. Email him at or connect with him via Twitter @Sinclair_Ceasar

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