We called week five the end of this experiment…but it didn’t feel like the end. So we’re back for one more!

Since we last recorded, we flew to Montana and spent two days filming a proof of concept for Matt’s Creative Places – two days of shooting, a hired DP, drone footage, interviews in people’s homes and bookshops, and one terabyte of footage he hasn’t looked at yet.

Lindsey played producer in Montana, and learned that a little distance from the novel gave her a clearer picture of it than immersion had, and she’s landed somewhere slightly unhinged: draft the whole thing by the end of the year. That means outlining, which she has never done, and protecting early-morning writing time through the busiest season of her work year.

As always, this is an unscripted conversation—two people reporting back honestly on a season of creative work.

In this episode

00:00 — Brighter, faster, funnier

We’re trying!

01:38 — Matt’s update: Two days in Montana

Matt hit the ground running in Montana - a hired DP fir two days, interviews lined up, drone work over the river, on-the-street shooting, and a terabyte of footage…and Lindsey unlocks her dream job as producer.

Plus: a lesson from da Vinci’s notebooks, the joy of participating in a creative place (not just documenting one), and next steps for Creative Places.

25:35 — Lindsey’s update: A whole draft by the end of the year?

Lindsey shares her plan for the novel, admitting a little space away was good for it.

Next up: write a first draft, with a loose outline, and being mindful of balancing this with a busy season of work.

35:14 — Borrowing belief and the end of season one

We identify one of the secret sauces to this container: borrowed belief. We’re each able to dream slightly bigger for the other person than we can for ourselves, and that borrowed belief is what carries work into exciting territory.

That’s a wrap on Season 1…but keep a seat warm for us.

Mentioned in this episode

* Walter Isaacson’s Leonardo da Vinci

* Livingston, Montana and its literary community

* 37signals’ six-week cycles

What’s Next

Lindsey: Exhaust the list of scenes, build the timeline into a loose architecture, and start the exploratory draft—with protected early-morning time defended against the busiest stretch of her work year.

Matt: Move into post-production with actual dates on it—storyboard, voiceover, editors—and cut a trailer from the Montana footage before attempting anything longer. Look at grants as the deadline.

The Quest Log

If you’re running a side quest of your own, take a few minutes to consider:

* Over these last 5(ish) weeks: What did you learn? How did you grow? What do you know now that you didn’t know before you started? And what’s next for your creative side quest?

Tell us in the comments. And tell us what you made over these five weeks that didn’t exist before—we want to know whether you’re questing along with us in season two.

Until we quest again,Matt Trinetti & Lindsey Trout Hughes

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit creativesidequests.substack.com

This week’s episode arrived late, and for a good reason! Both of our quests pulled us away from our desks and out into the world.

We each ended up taking the wheel of the other’s side quest—Matt literally, behind the steering wheel on a research trip through Lindsey’s book territory, and Lindsey metaphorically, becoming Matt’s producer on a Creative Places proof of concept shoot.

As always, this is an unscripted conversation—two people reporting back honestly on a week of creative work.

In this episode

00:00 — Taking the wheel

We each took the steering wheel of the other’s side quest, literally and metaphorically.

01:24 — Shout outs

We share a few updates from your quests: a community writing group that nearly ended but didn’t, a screenplay moving from aspiration into actual pages, a new opening taking shape, and a curiosity that led someone out into London. With special thanks to Fran who contributed “grinds my goat” to Matt’s mixed metaphor collection.

06:13 — Lindsey’s check-in: Three pitches and arctic travel?

Lindsey wrote out three possible books over the five weeks and emailed her agent to get a meeting on the books. We muse on the importance and impact of being on location of visiting a place where a novel is set.

21:30 — Matt’s check-in: Planning a shoot and carrying a show?

Matt sent his concept doc to a handful of people and it still didn’t feel real. The only way to make it real is to shoot something – so he (through his new producer, Lindsey) has planned two days of filming in Montana. Cue existential crisis: can I carry a show?

35:58 — What happens after week five

Neither of us think we’d have landed here without the container. Lindsey doesn’t think she’d be pursuing a novel; Matt doesn’t think we’d be shooting in Montana. Have our side quests quietly become a main quests? And what’s next for this show? We’re still thinking about it, but we’d love your feedback.

Mentioned in this episode

* The Audacious Voyage Grant—grants for women whose voyage, literal or metaphoric, is tied to a significant first

* Anthony Bourdain (Parts Unknown) and Stanley Tucci (Tucci in Italy)

* Livingston, Montana

* London Writers’ Salon, on building containers that make the work inevitable

For next week

Lindsey: a mood board for the novel, capturing the images and details from the trip while they’re still fresh, and sketching out what it would take to have a first draft by the end of the year.

Matt: three days in Livingston. One day walking around and talking to people, one day shooting landscape and exteriors, one day of interviews.

The Quest Log

If you’re running a side quest of your own, take a few minutes with these:

* Who can support your quest, and whose quest can you support? Things become more possible with the support of others.

* What are you telling yourself you need before you begin? Name the access you don’t have, then ask what version can be built inside those constraints.

* What would make your project feel real? Put something on the calendar. Tell someone your plan. Take the first step.

This is the last of our five weeks, so we’d especially love to hear from you—whether you’ve commented every week or not at all. How were these five weeks for you? What did you make? What changed? What surprised you? What are you proud of, and what are you carrying forward?

Tell us in the comments. We’ll be gathering your answers into a wrap-up once we’re back from Montana.

Until we quest again,

Matt Trinetti & Lindsey Trout Hughes

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit creativesidequests.substack.com

This week, we explore what it takes to give a project the experience of being trusted. Lindsey named it best—creative self-trust has nothing to do with believing a project will be great. It’s about accumulating evidence that you keep the promises you make to yourself.

As always, this is an unscripted conversation—two people reporting back honestly on a week of creative work, including the homework neither of us quite did.

In this episode

00:00 — Mixed metaphors and giving people grace

Lindsey confesses her favorite thing about Matt is the way he mashes two turns of phrase into one (”now we’re rooting you on”). Which turns into something more useful: how hard it is to say anything perfectly out loud, and how much grace that earns other people when a line gets pulled out of context.

02:12 — Shout outs

Kelli brought her characters together in scenes, drafted working titles, read comps, watched films alongside their scripts, started thinking about the proposal—and applied for two scholarships and got both. She also shared the realization we keep coming back to: stop beating yourself up for not making it ten years ago. You’re a stronger writer making it now.

Jenny’s movie star recipe cards are coming along (photos, please), and she’s watched Listers twice since it came up here. Fran wrote in about how much actually changes in seven days. And Therese, who began on a permission-to-play quest of collage and fragments, found the real work happening in her journal—which led her back to a project she’d let go dormant, and to the fragments she’s been writing for years without knowing what they were for.

05:56 — The document instead of the deck

Matt’s homework was to personalize the pitch deck, have real conversations, and get a camera person booked. He did approximately none of it. What he did instead: made the 16-page concept doc more visual, took about 90% of Lindsey’s line edits, and put it in front of five people—a director, a food writer who’s developed for TV, a novelist friend, his dad and his brother—some sent, some soft-asked first. On choosing the fuller document over the more impressive artifact, and why the deck can wait until somebody actually asks for one.

12:41 — Writing it as if it’s already real

The energetic shift from “here’s something I’m kind of thinking about” to a flat statement of fact. Matt on the feeling of inevitability, and the fear directly underneath it: he still hasn’t touched the actual work. Can he hold it on screen? Will he even enjoy doing it? Plus the thing he’s slowly relinquishing—the belief that he has to be able to do every part of it himself.

19:11 — Montana, and deciding before you’re certain

There’s a window to shoot something in Montana. Rather than wait for the conditions to be right, Lindsey says: commit, I’ll look at flights when we get off this call. Matt sketches three tiers of what a sizzle could be—full concept piece, something smaller, or thirty seconds of B-roll and him walking. Aim for the biggest. Settle for the smallest. Maybe make all three.

23:36 — 100 things (and two books that weren’t the book)

Lindsey did the exercise she gives everyone else and rarely does for herself, and reports it’s the reason she spent the week thinking about her own project in spare two-minute gaps. The list produced scenes, questions, formal constraints, possible structures—and, unexpectedly, two more book ideas. She now has three ideas she’d be genuinely happy to write.

31:01 — Self-trust, and keeping promises to yourself

The realization of the week: early-stage creative work isn’t about making the project cohere. It’s about building a relationship with it strong enough to survive until coherence arrives. Matt on the creative impulse as a voice you either listen to or slowly stop being able to hear. And Lindsey on the screenplay she’s been describing aspirationally for five years, and what it would mean to give that project the experience of being trusted too.

38:41 — Receptivity you can carry

Lindsey traveled this week and skipped the contemplative practice entirely—and found she was no less receptive. Ideas kept arriving. Plus her plan to go and visit the actual world of the book, with a list of questions for the people who live in it.

46:53 — What happens after week five

We’re one week from the end of a five-week experiment, and we’re not sure what happens next. Closing it as a season feels right. Both of us also admit we’d selfishly like to keep the container. We’d genuinely like your opinion on this one.

Mentioned in this episode

* Doireann Ní Ghríofa, Said the Dead

* Lindsey’s conversation with Doireann at London Writers' Salon

* Julia Cameron’s Artist Date

* Steven Pressfield’s Foolscap Method

For next week

Lindsey: write out the three pitches properly—succinct enough to say out loud, clear enough to take to her agent—plus a loose architecture of the novel. Movements, not an outline.

Matt: keep sending the doc to people who might have something to say about it, and make a real plan for Montana. Dates, interviews, a camera person, possibly a drone.

The Quest Log

If you’re running a side quest of your own, take a few minutes with these:

* What did you actually make this week? Not the ambitious version you wrote down last week. The real one.

* Where did you choose the useful thing over the impressive thing? Or where are you still polishing something nobody has asked you for?

* What promise have you made to yourself lately—and did you keep it? Self-trust is built out of evidence, not intention.

* What have you been describing aspirationally for years? What would it take to give that project the experience of being trusted?

* What’s the smallest real version of your project, and what’s the biggest? Aim for the biggest. Commit to the smallest. Tell someone which.

Tell us in the comments. We read all of them, and we’d love to see photos of what you’re making. And one more this week: we’re deciding what happens after week five. Should this stay a five-week season, or would you want an ongoing container? Say so below.

Until we quest again, Matt Trinetti & Lindsey Trout Hughes

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit creativesidequests.substack.com

This week we discussed how letting go of outcome while still wanting something badly are not opposites, and learning to hold both at once might be at the heart of creative work.

Lindsey went into the week wondering whether to keep publishing at all. Somewhere in the middle of it she thought, nobody cares—and it landed as freedom rather than despair. Days later, a book idea arrived.

Matt turned his concept doc into a rough pitch deck and found a hypothesis he believes in, but questions whether he’s only collecting evidence that agrees with him.

As always, this is an unscripted conversation—two people reporting back honestly on a week of creative work, including the parts that didn’t go anywhere.

In this episode

00:00 — Cold open and shout outs

Lindsey shares her old pre-performance acting ritual: lying down, taking a full-body inventory, asking each part what it needed. Matt on talking to his body before three days without food.

Plus – a special shout out to Kelly, Therese, Jenny, SJ, Nanya, Janet and Joan. Thank you for sharing your quests! Treatments and proposals, collage and fragments, Substacks and newsletters, a piece of art for a mum, two years of travel writing bound into hard copy, a nature journal—and a variety of quests in between.

05:41 — Nobody cares (and why that helped)

Lindsey’s doubt turned out to be bigger than the project—she was asking whether to keep publishing at all. She shares the reframe that unlocked it, the distinction between ambition and attachment, and the idea that arrived days after she’d decided she might be done.

22:27 — Lindsey’s contemplative practice

Lindsey shares her contemplative practice for “receiving” images and ideas: A mentor text, fifteen minutes of very close reading, fifteen minutes of meditation. A notebook by the bed for whatever surfaces in the space between waking and sleeping.

39:39 — Matt’s deck becomes a real thing

Matt expands his concept doc for Creative Places and starts to build a rough Canva deck to help visualize the project. He expands on his three-part hypothesis: geography pulls you, an economic ecosystem keeps you there, community sustains you. Matt also recognizes the bias in his research so far.

54:07 — Why your own story belongs in the work.

Lindsey helps Matt see how integral he is to his Creative Places project. Matt shares how he didn’t consider himself creative until he was about 30, and why that might help the project.

01:03:00 — Reflections on the public container of Creative Side Quests

Although we’ve been having this conversation privately on Fridays for a year, three weeks of doing it out loud and the pressure has changed. Both of us admit how much of this week’s progress is simply not wanting to show up empty-handed.

Mentioned in this episode

* Elizabeth Gilbert on hobby vs. job vs. career vs. vocation.

* Matt Bell, Refuse To Be Done

* Joanna Nadin on the “living document”.

* Listers, the birding documentary

* Brian Hastert’s “100 things” method

For next week

Lindsey: a list called 100 Things That Could Happen in This Novel, plus “writing the islands” from Matt Bell’s Refuse To Be Done.

Matt: personalize the deck so it’s shareable, have the first real conversations about it, and try to get a camera person and a date in the diary for a sizzle reel.

The Quest Log

If you’re running a side quest of your own, take a few minutes with these:

* What actually happened this week? Not what you meant to do. What you did.

* What surprised you? The thing you didn’t see coming is usually the thing worth following.

* Where are you rushing toward certainty when you could still be gathering possibilities?

* Is what you’re making a hobby, a job, a career, or a vocation — and have you been confusing one for another?

* What are you committing to before next week? Say it out loud. It’s harder to skip that way.

Tell us in the comments. We read all of them, and we’d love to see photos of what you’re making. And if someone else’s quest sparks something, cheer them on.

Until we quest again,Matt Trinetti & Lindsey Trout Hughes

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit creativesidequests.substack.com

This week, we sit down to reflect on process and progress.

Matt drafted the first concept document for Creative Places, wrestling a years-old idea into something he can finally share with other people.

Lindsey filled notebook pages with images from the edge of sleep, and found herself asking bigger questions than she expected.

As always, this is an unpolished conversation between two collaborators trying to help each other make meaningful progress—one week at a time.

Episode Guide

00:00 — One Week Later

We check in after the first week of our quests and reflect on what it feels like to work toward something publicly. We also talk about why documenting the creative process (not just the finished work) is becoming central to this experiment.

05:00 — Matt’s First Concept Doc

Matt shares the rough two-page concept document for Creative Places—his television series exploring why certain places become magnets for creativity. Together we unpack the logline, central question, “why now,” and what surprised him most while finally gathering years of thinking into a single document.

13:45 — From Idea to Pitch Deck

What’s the next tangible step? Matt commits to making the project visual, and Lindsey nudges him toward introducing more personal storytelling and clarifying the experience he wants viewers to have.

31:40 — Lindsey’s Week of Creative Practice

Lindsey shares her experiment with staying receptive to images emerging between wakefulness and sleep, using them as prompts for daily notebook writing.

36:00 — Following Curiosity Without Losing the Plot

Lindsey reflects on finding the next idea she wants to persue. Together we explore one of the central questions facing many creative people: when do you stay the course, and when do you let a project evolve?

Quest Log

How is your own Creative Side Quest unfolding?

This week’s check-in prompts:

* What did you do this week?

* How did it feel?

* Where do you feel stuck?

* What’s your goal for next week?

Feel free to answer one question or all four.

And if someone else’s update resonates with you, cheer them on. Half the experiment is discovering what becomes possible when creative people keep each other company.

Matt Trinetti & Lindsey Trout Hughes

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit creativesidequests.substack.com

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

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit creativesidequests.substack.com