Floating Cloister · A Freelancer's Gathering
Floating, but rooted.
A community for the caregivers of their own work.
Aug 26 · 9:00 AM New York · 10:00 PM Korea · Online · Google Meet
From Dream Job to Lifetime Job
olive
Building my own work system for my lifetime job — with Olive (Marketing Career Since 1998 · Meta, Microsoft & Yahoo).
Register →The freelance internet is loud. Most of us aren't.
- You post less than you produce.
- You use AI without feeling owned by it.
- You've stopped explaining why you're not scaling.
- You want peers — not a coach, not a course.
If that sounds like you, this room was built for you.
Not a course. Not a conference. Not a networking community.
The monthly room
Last Wednesday of every month, starting July 29. 60 minutes online.
One in-person gathering
Brooklyn this year, possibly another city the next.
Long-form letters
Interviews with practitioners we admire, essays on solo work in the AI age.
Members write. Founders curate. The community is the magazine.
Last Wednesdays, July to December.
Six months, one rhythm — themed around work and rest.
- Jul 29Christiana ChaeDesigning Your Own Pace12 PM ET · Closing No.1
- Aug 26Olive (Euna Seo)Building my own work system for my lifetime jobformer Meta marketing lead, author
- Sep 30NextJosiah Forgath × Notion NYCThe System Month Ⅰreal setups, opened live
- Oct 28Notion NYC CommunityThe System Month Ⅱmore systems worth borrowing
- Nov 18*Divya PaiPrompt as Mirror — season finale*moved off Thanksgiving week
- Dec 16*Mini & YoumeAnnual Closing — letters & the year*holiday-week adjustment
*November & December dates adjusted around holiday weeks.
One letter, one December.
At first, this only happened in a room in Brooklyn. Now it's open to everyone. Each month, in the online room, we write toward the same fixed point: a letter to ourselves in December. Seoul, New York, somewhere in between — wherever you are, you write it, and we hold it.
On December 22, the letters come back. Write one, and if enough of us do, it returns not as a screen but as a real envelope in the mail. That return is the heart of the gathering — months from now, when you've forgotten what you were thinking, a version of yourself you'd lost track of arrives at your door.
— held through 2026, returning December 22.Come with us.
The room where the community began. Fifty freelancers, six hours, one letter — and a recording of the day in the letters to come.
Building my own work system for my lifetime job — with Olive (Marketing Career Since 1998 · Meta, Microsoft & Yahoo).
Register →Can't make the room? Subscribe to the letters. We publish slowly — interviews, essays, the occasional reflection — when we have something worth sending.
Subscribe →The small enclosed courtyard. Members-only Slack, two letters rituals a year, auto-eligible for POPOPO Magazine, Q&A priority at monthly meetups.
Either way, we'll be in the same conversation eventually.
