#89: Sarah Detweiler — Redefining Success, Maintaining Creative Freedom, and Unmasking Your Authentic Self

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

What does it take to see the world around you the way an artist sees it? In this episode of Always Choose Orange, I chat with visual artist Nasir Young about how skateboarding transformed the way he moves through cityscapes and how that way of seeing laid the groundwork for his detailed oil paintings. His work documents the small, often overlooked wonders of urban life, including brick walls, corner stores, and gas stations.We talk about:Always having a handful of projects to work onHow to tell intriguing visual stories without including a single personTitling your work to evoke curiosity and meaningStudio routines (including scheduling time to read manga)Oh, and by the end of the episode, don’t be surprised if you never look at vans the same way again.Website: http://www.nasiryoungart.com    Instagram: https://www.instagram.com/nasiryoungart/

With 2025 behind us, my brother Andrew and I check in with each other to talk about some of the most powerful, entertaining, and interesting books we read in the second half of the year. Between the two of us, we read a lot of books (probably too many) so these were, for us, the best of the best.We 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? As we answer these six questions, we venture down a few side streets and touch on a variety of topics such as goal setting, purple prose, contemplative prayer, and even Count Dooku's journey to the Dark Side. If you enjoy the written word and enjoy stumbling across new books, chances are, you'll find something here you'll love!

What does it actually take to build a sound slowly and deliberately? In this episode of Always Choose Orange, I talk with electronic music producer and multi-instrumentalist Ankurana about the long, unglamorous reality of developing a musical voice — years of experimentation, hundreds of abandoned ideas, and learning when to stop adding and start listening.We talk about:Learning music production the hard way (after years of trial and error)Using nature and field recordings as musical materialWhen to strip ideas back instead of adding moreThe subtle details most listeners never consciously noticeWe discuss the value of building cohesive bodies of work in a time when music is often consumed in fragments, as well as why Ankurana still thinks in terms of albums, arcs, and emotional continuity rather than isolated tracks. Bandcamp: https://ankurana.bandcamp.com/YouTube: https://www.youtube.com/@ankuranamusicInstagram: https://www.instagram.com/_ankurana_/SoundCloud: https://www.soundcloud.com/ankurana

Any Austin changed the rules of gaming content on YouTube. So what happens after that?In his return to Always Choose Orange, Austin reflects on the growth and influence of his channel over the past year. We talk about the benefits and challenges of bringing on additional team members, the one thing he believes should be the true goal of time management, and how he uses the rise of imitators as competitive fuel rather than a distraction.During the second half of our conversation, I ask Austin a series of questions submitted by his audience. We examine how his videos evolve from draft to draft, a specific moment in Mega Man 2 that has stuck with him since childhood, and the likelihood of ever seeing another episode of Eggbusters.To wrap things up, we do a career retrospective using the presidents on Mount Rushmore as a loose metaphor for key milestones in his YouTube journey. YouTube: https://www.youtube.com/@any_austinInstagram: https://www.instagram.com/any_austin/Patreon: https://www.patreon.com/any_austinTikTok: https://www.tiktok.com/@any_austin

How do cultural values shape narrative structure?This is one of the main questions in author Henry Lien's most recent book, Spring, Summer, Asteroid, Bird: The Art of Eastern Storytelling. After leaping headfirst into writing at age 42 and spending some formative time at the Clarion Workshop learning from George R.R. Martin, Kelly Link, and Chuck Palahniuk, Henry developed a fascination with form which eventually led him to kishōtenketsu (East Asian four-act structure).In this episode of Always Choose Orange, Henry and I talk about:The differences between a typical Eastern story and a typical Western storyWhy Disney's version of Mulan strayed from the original source materialHow newer writers can steer clear of cultural appropriationThe use of circular narrative structure in the level design of the Metroid games Website: https://henrylien.comInstagram: https://www.instagram.com/henrylienauthor/Facebook: https://www.facebook.com/HenryLienAuthor Resources mentioned by Henry:Powers of Ten™ (1977)https://writingtheother.comWriting the Other by Nisi Shawl & Cynthia Ward

You know what they say, “you can’t spell artificial without art!” …What? What do you mean you haven't heard that? I'm sure someone, somewhere has said it… Anyway, in today's episode, we explore a provocative idea put forth in Carl Wilson’s book Celine Dion’s Let’s Talk About Love: A Journey To The End of Taste that in a sense, all authenticity in art is a kind of performance. If we adopt that perspective, it raises a lot of questions, including: how do I make art with conviction while simultaneously making it for an audience? Using examples from punk and emo concerts I went to in high school and college, as well as my personal experience making music of my own, we stumble through some possible answers.

Have you ever been in a meeting that just as easily could have been an email? Have you slogged through a personal development book only to realize that the whole thing could've been summed up in a few tidy bullet points? With the advent of LLMs such as ChatGPT, Copilot, and Gemini, it's easier than ever before to access information in a fraction of the time. And many times, that's a great thing. But everything comes with a cost. In today's episode, we examine that cost and segue into a set of practical questions you can ask yourself whenever you're struggling to bring a creative project to life.