#94: For the Love of the Game

Have you ever grabbed your phone to respond to a text message, only to look up an hour later after getting swept into a hazy deluge of political arguments, LLM-written articles about the future of AI, and cringey videos of people dancing?In today’s episode, we explore the idea of “analogue doomscrolling,” an alternative to the algorithmically-determined torrent of information and negativity that’s magnanimously provided to us by news sites and social media feeds at any given moment. What if, instead of endlessly scrolling through a screen, we redirected that urge to wander toward the physical world? If you’re looking for a way to satisfy your curiosity, get creatively inspired, escape the algorithm, and remain rooted in the world around you, this brief odyssey into the wide world of knowledge may be exactly what you’re looking for. The inspiration for this episode: https://youtu.be/e41DYhnA2_A?si=96lYW9myRU_AaMsN

Around 50 minutes into the 2024 animated film Flow, something completely unexpected happens. I won’t tell you what it is (I don’t want to spoil the movie for anyone who hasn’t seen it) but it serves as a fascinating reminder of why, as creatives, we need to pay close attention to the expectations we’re setting and the way we’re preparing our audience for what they’re about to experience. In this episode, we’ll examine that moment, explore how it changes the experience of the film as a whole, and consider one simple question that can help us avoid making the same mistake in our own art.

My brother Andrew is in the house and (of course) we’re talking about books! In this episode, the two of us reflect back on what we’ve read so far in 2026 and use the following questions as a guide:Which book surprised you the most?What is the most ambitious book you read this year?Which book had the best prose?What is one book that made you cry?Which book impacted your life the most?What was your personal favorite? Throughout the 1.5 hour conversation, we venture off the beaten path and explore a variety of topics including mystery, meditation, neuroscience, fish tank design, the key to reading old books, minimalism, empathy, and a fascinating A.I. prompt we used to learn more about our individual writing style preferences.You can purchase Andrew’s book, Just Simply Sitting, here: https://www.amazon.com/Just-Simply-Sitting-Andrew-Drake/dp/B0GVZ94VS3

What in the world is a “clearness committee” and what could it possibly have to do with our creativity? In today’s episode, we make a few observations about a short excerpt from Parker J. Palmer’s book Let Your Life Speak: Listening for the Voice of Vocation and examine the relationship between feedback, question-asking, and increased clarity when it comes to our art and purpose. We also talk about the unique roles that critique and encouragement play at different stages of our creative process.If you want to learn more about the use of clearness committees in Quaker spirituality, here's a solid resource: https://www.fgcquaker.org/fgcresources/spiritual-practices/clearness-committees/

Do you ever want to quit working on a creative project because it feels like a slog? Or find yourself saying that you just need to get it done as fast as you can so you can move onto something else? If that sounds familiar, number one: you're not alone, and number two: thankfully, there are some tools for that. This episode of Always Choose Orange uses a clip from a recent J. Cole interview to give you a few powerful questions to ask when your art-making feels dull and uninspired.

How do songs actually come into being?In this episode of Always Choose Orange, Mat Charley (co-founder, lyricist, and producer of Raynes) and I talk about the craft and obsession behind his songwriting.After more than 30,000 hours spent writing music, Mat has learned that songs rarely emerge from force alone. Instead, they reveal themselves gradually through melody, iteration, and careful attention to language. As he puts it: a song wants what it wants.In our conversation, we explore:How and why Mat spends 10–16 hours a day writing music without burning outHis “melody first” approach to building songsHow he uses literary devices and poetic structure in his lyricsWhat it’s like writing deeply personal songs for someone else to singHow Raynes organizes ideas, images, and fragments into larger musical projects We also talk about artistic obsession, creative discipline, and why, after writing nearly 1,000 songs, Mat still wakes up excited to make the next one. Website: http://raynesmusic.comInstagram: http://instagram.com/raynesmusicYouTube: https://youtube.com/@raynesmusicBandcamp: https://raynes.bandcamp.comFacebook: http://www.facebook.com/raynesmusicDiscord: https://discord.gg/venx9Mg7zG

Have you ever looked into your closet thinking, “None of this feels right?”In this episode of Always Choose Orange, I talk with stylist Ellie Richards about how clothing can act as a mirror for how clearly we understand ourselves.Drawing from fashion psychology, Ellie explains why developing a personal style starts internally rather than with aesthetics or trends. Instead of copying influencers or chasing the latest look, she encourages people to understand their lifestyle, preferences, and identity first, and then build a wardrobe that reflects those things.In our conversation we discuss:Why clothing influences how we think, feel, and behaveHow “self-concept clarity” affects personal styleWhy copying aesthetics from influencers often falls flatThe minimalist wardrobe pyramid and dopamine dressingHow to identify your contrast level and seasonal color paletteWhat to look for when buying ethical and sustainable clothing Along the way, Ellie also shares insights from her experience running a sustainable fashion boutique and explains why she sees herself as an educator rather than an influencer.Website: https://www.nuude-studio.comYouTube: https://youtube.com/@ellie.richardsInstagram: https://www.instagram.com/ellierichards.intelTikTok: https://www.tiktok.com/@ellie.richards

How do you design an experience or piece of art that transforms someone rather than simply giving them more information? In this thought-provoking episode of Always Choose Orange, author and philosopher Peter Rollins and I talk about how he's spent the last 20+ years of his life plumbing the depths of some of the deepest philosophical and theological questions. From his early days creating "transformance art" through his (in)famous Ikon gatherings to the powerful new communities he's building around a sense of shared lack, Peter has dedicated his life to helping people come face to face with the universal human experience of loss. The two of us explore a bunch of fascinating ideas, including:The role of discomfort in making space for transformationHow he built his legendary Atheism for Lent practiceHow, in some ways, many great artists spend their whole career circling a single questionWhy reimagined forms of community are more important than ever Website: https://peterrollins.comYouTube: https://www.youtube.com/channel/UCweF6BScvFnbsymouI-znDAInstagram: http://instagram.com/peter_rollinsFacebook: http://www.facebook.com/orthodoxheretic  Soundcloud: http://soundcloud.com/peter-rollins

In March of 2024, Coulou sat down in the bedroom of his Brooklyn apartment with his guitar, some effects pedals, and a trumpet. What happened next was something special. He set up a camera, strummed his guitar, found some chords he liked, looped them, grabbed his trumpet, sounded the first note, and Coulou’s Cafe Trumpet Meditations were born.Now, two years later, Coulou has released more than 65 of his twenty-minute meditations and learned a number of powerful lessons along the way.In this episode of Always Choose Orange, we talk about: Why Coulou almost scrapped the meditation that became his most viewed video on YouTubeHow long-form improvisation has impacted his songwriting (including the heartfelt story behind his song “Joe”)The difference between improvising with a band and improvising by yourselfHow he selects his recording locations and the painstaking process he goes through to make sure he creates the right atmosphere for his viewers  Website: https://www.couloumusic.comBandcamp: https://coulou.bandcamp.comInstagram: http://instagram.com/coulou__Facebook: http://facebook.com/C0ULOU

How do you keep moving forward once your work begins to resonate with people on a larger scale?In this episode of Always Choose Orange, I talk with mixed media painter Sarah Detweiler about the quieter, more complicated season that follows increased public recognition.While Sarah’s Hidden Mother series helped her understand herself more deeply as an artist, this conversation focuses on what came with that realization: the decision to keep evolving, to follow curiosity rather than expectation, and to make work that remains honest even when it's moving in fresh and unexpected ways.We talk about art as a way of processing internal experience, the freedom that comes from letting go of external metrics, and how Sarah thinks about authenticity, attention, and care as she builds new bodies of work.Along the way, we explore:Using art to process things that are difficult to name with wordsLetting curiosity (and not audience response) guide the workMaking art with ADHD and embracing experimentation over cohesionThe tension between visibility and freedomBuilding solo exhibitions and knowing when a body of work is finishedFeedback, inner critics, and learning which voices to trustParenting, time constraints, and how limitation clarifies valuesWhy authenticity requires not thinking about how the work will be receivedAt its core, this conversation is about staying honest with yourself as your work changes and about trusting process over performance as you continue to grow as an artist.Website: https://www.sarahdetweiler.comInstagram: https://www.instagram.com/sd_artifacts