Week 1: Welcome to Creative Side Quests!

For the next five weeks, we’re inviting you to join us on a creative side quest—one creative pursuit that’s exciting enough to make room for this summer.

Every week, we’ll sit down for an unscripted conversation about our own quests: the progress, doubts, breakthroughs, false starts, and coaching that happens between two collaborators trying to make something they’re proud of.

We hope you’ll choose a quest of your own and pursue it alongside us.

Episode Guide

00:00 — Welcome to Creative Side Quests

We introduce the experiment: a five-week summer container for pursuing creative work in good company. We talk about why we created Creative Side Quests, what we hope this space becomes, and why supporting other people’s creativity isn’t always enough—we wanted a place to reconnect with our own.

05:50 — Two Types of Creative Side Quests

If you’re still deciding what your own quest might be, we introduce two ways of thinking about it:

* Dream on a Deadline — an ambitious creative goal with a self-imposed five-week finish line.

* Permission to Play — following a creative curiosity simply because it delights you, without worrying where it leads.

We also talk about why neither approach is “better” than the other, and why every quest deserves an artifact or moment of sharing at the end.

11:45 — Why We’re Having These Conversations Publicly

These are unpolished, real conversations between two collaborators trying to help each other make meaningful creative progress. We talk about what we hope you’ll get from watching—and why we hope you’ll become the third person in the room by embarking on a quest of your own.

12:18 — Matt’s Quest: A TV Pitch for Creative Places

Matt shares the project that’s been tugging at him for years: an exploration of the relationship between creativity and place. What makes certain places become magnets for artists? Can creativity itself be designed into a place—or a community?

For his quest, Matt commits to creating a compelling pitch for the tv project, clarifying the heart of the idea, and getting it in front of someone who can take it seriously. We also identify his task for the first week: drafting his 1-page concept doc.

47:03 — Lindsey’s Quest: Exploring Mysticism and Creativity

Lindsey shares a project that’s been calling to her: exploring the intersection of creativity, mysticism, ritual, and artistic practice. Together we wrestle with a familiar creative tension—how to move from years of reading, thinking, and collecting ideas toward actually making the work.

We narrow the focus to a first meaningful step: building a daily practice, following her curiosity with discipline, and beginning to generate a body of work that could eventually become something larger. We end by identifying her first concrete task for the week: draft one essay on mysticism, and write 400 words a day toward a novel.

Join Us!

If you’re taking on a Creative Side Quest this summer, we’d love for you to do it alongside us.

Over the next five weeks, join us in the comments section of each post. Consider it our communal Quest Log:

* Introduce yourself. Tell us about your quest in the comments.

* Check in each week. Let us know what’s working, what’s proving difficult, and what you’re discovering.

* Cheer someone else on. Half the point of this experiment is seeing what happens when creative people make things in good company.

* Share what you’ve made. At the end of these five weeks, we’ll publish a community showcase where everyone can share what they’ve made, learned, or uncovered along the way.

We’re so glad you’re here.

Let’s see where these next five weeks take us!Matt Trinetti & Lindsey Trout Hughes