What do you do when the room you need doesn’t exist?

You build it.

In this episode of The Awkward Handshake, Mary and Megan sit down with author, storyteller, and ghostwriter Jessie Kwak to talk about what it looks like to create the kind of community you wish you could find.

Jessie shares how she built a thriving writers’ community in Portland — one that started small, grew through trust and referrals, and now includes both a real-life backyard gathering and an active online Slack space. Along the way, she offers a thoughtful look at what makes communities work, why curated spaces matter, and how good people really do know other good people.

This conversation goes far beyond “start a Facebook group and hope for the best.”

It’s about intention.
It’s about trust.
And it’s about realizing that if the space you need isn’t out there yet… you may be the one meant to build it.

In this episode, we talk about:

• Why curated communities often feel safer and more useful
• How Jessie’s writers’ group evolved from an in-person meetup into a larger Slack community
• What it takes to maintain trust in both physical and online spaces
• Why strong communities grow best through referrals and real relationships
• The difference between shallow promotion and meaningful collaboration
• How collaboration often takes longer than people expect
• Why networking can lead to friendships first and opportunities later
• The hidden labor of being the “mother hen” of a community
• What happens when you can’t find the room you need

Our Guest

Jessie Kwak is an author, storyteller, and business book ghostwriter based in Portland, Oregon. She writes thriller novels, science fiction, and nonfiction, and helps other writers bring their books to life through coaching and ghostwriting. She also hosts a vibrant writing community in Portland that has grown into a larger Pacific Northwest writers network.

https://www.jessiekwak.com/

Why this episode matters

If you’ve been waiting for the perfect room, the perfect group, or the perfect invitation… this episode is your reminder that sometimes the strongest move is to stop waiting.

Build the thing.
Invite the good people.
Let it grow from there.

Keep in touch!

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