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Gathering Event Calendar

Image by Yianni K.

The Gathering Series: Coffee + Connection

(In-Person)

Casual conversations designed to help women in business connect, collaborate, and refer each other.

 

The Treehouse

1 Riverside Rd, Riverside, IL
Friday, September, 18, 2026

8:30 am -10:00 am
Click image to RSVP

Image by Marcos Paulo Prado

Journaling Club (In-Person)

​Journaling gathering inspired by The Book of Alchemy by Suleika Jaouad. Suleika describes a journaling club as “a gathering that’s equal parts tender and mischievous… to write together. This is a writing-forward experience. Drinks available for purchase.

New Book Joy

3741 Prairie Ave., Brookfield, IL
Thursday, October, 1, 2026

6:00-7:30 pm

$10
Click image to purchase tickets

Image by Viva Luna Studios

Tarot & Moonlit Musings

​Join Carisa and Brittany Caldwell for tarot readings and guided journaling. Limited to 10 people.

The Treehouse

1 Riverside Rd, Riverside, IL

Tuesday, September 29, 2026

7:00-9:00pm

$40

Click image to purchase tickets

The Gathering Series

Spaces for thoughtful conversation, creativity, and connection.
 

Some of the most meaningful conversations happen when there isn’t much structure around them.

Just a welcoming space, a few thoughtful prompts, and people who are open to talking honestly.

Over the past year, I’ve started hosting small gatherings designed to create that kind of room.

They’re simple by design.


No pitches. No pressure to perform. No expectation to “network.”

Just good coffee, thoughtful conversation, and the chance to meet other people who are building interesting things in their lives and work.

These gatherings have taken a few different forms so far, including:

Coffee + Connection mornings for women founders and entrepreneurs
Journaling circles (both in-person & virtual) exploring reflective prompts and creative writing
Creative workshops that combine art, writing, and conversation

Each one is a little different, but the intention is the same:
to create a space where people can slow down, think out loud, and connect in a more real way.

Bringing a Gathering
to Your Community

I also facilitate gatherings for retreats, founder communities, and creative spaces that want something a little different from a typical networking event.

 

These spaces are designed to be warm, relaxed, and thoughtfully held. The goal isn’t to force connection, but to create the kind of room where people can slow down, speak honestly, and have conversations that feel more real.

 

Sometimes this looks like a Coffee + Connection style gathering around a table with a smaller group.

 

Other times it takes the form of a guided conversation, journaling circle, or reflective workshop for a larger room.

 

If you’re planning a retreat, event, or community gathering and would like to create a space like this for your group, I’d love to hear about it.

 

If you’ve ever wished for a room where the conversation feels a little more real, you’ll probably feel at home here.

Connect

© 2026 Carisa Deegan.

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