The Sober Creative Podcast

with Josh Woll
  • 5.0 (3)
  • Health & Fitness
  • Updated Weekly

In this live Substack series, I explore intimate conversations with people navigating their sobriety journeys. Each episode highlights personal transformations, practical strategies, and the unexpected creative advantages of clear-minded living. These uplifting discussions reveal how sobriety enhances artistic expression, business success, and personal fulfillment. Join us to discover how these individuals are finding greater authenticity, purpose, and creative power through sobriety. newsletter.thesobercreative.com

  1. 2d ago

    Episode 067 - The Part Sobriety Didn't Touch

    Steve [Sage-Outlaw-Caregiver] on the crash that came six years after he quit, and finding out at 40 that he was creative Steve didn’t take a drink until he was 21. He calls it a reverse Benjamin Button. Most people get their worst drinking out of the way young. His started late, got heavier every year, and by the back half of his 30s it was every single day. He stopped on August 4th, 2018, after his drinking got him sent home from a post in South Africa. There was no program and no meetings. He was so depressed he couldn’t leave his room, which broke the habit before he ever decided to break it. Then nothing was fixed. Six years later, still sober, he was diagnosed with ADHD, watched two decades of near-perfect performance reviews collapse, went through termination proceedings, and checked himself into inpatient care in the Colorado mountains because he couldn’t guarantee his own safety. Almost none of what he found there had to do with alcohol. It had to do with a man who had spent his entire adult life believing he was his job. What he built on the other side of it is a dog wellness company and a world of corvid characters he draws with AI, which is not where a career foreign aid officer expects to end up. A note before you read on: Steve speaks openly about depression and two suicidal episodes. He gave his full blessing to share it. If any of this hits close to home for you, please reach out to someone you trust. Show Notes [02:36] A Late Start That Got Worse With Age * Steve went to Tulane in New Orleans, a heavy drinking town, and mostly ran with the engineering and finance crowd. He barely drank in college and never blacked out there. * After graduation he took an internship with the Department of the Army and landed in a cohort with a real drinking culture. Classes ended at three and the group went straight to margaritas. * He moved every two years, served overseas with soldiers, and drank his way into every new room. He describes himself as a chameleon during those years. * By the second half of his 30s, it was daily. Key Insights “It seemed like a shortcut. So that’s how I kind of just got sucked into it.” [11:15] When Drinking Flipped From Fun to Function * Steve rose fast, three years with the Army and then 17 at USAID. Every promotion brought a fresh wave of imposter syndrome. * He was moved from Washington, D.C. to South Africa to run a large office. He remembers blacking out one night because he had to fire somebody the next morning. * The circle kept shrinking. Five people at the bar became three, then two, then just him. * Drinking stopped being about having no responsibilities and started being about having too many. Key Insights “It becomes less of a social thing and more of a, this is just something I need to do.” [14:26] August 4th, 2018 * His drinking started affecting his work. He was sent back to the United States from South Africa. * The depression that followed was so heavy he couldn’t get out of his room, so he stopped drinking without ever making a plan to. * He had to leave his dogs behind in South Africa for two months and wasn’t allowed to visit them. * He never went to AA. He just stopped. Key Insights “August 4th is the day I returned to the United States and I thought my life was over.” [17:45] COVID, ADHD, and the Loss of Structure * Working from home stripped away the outside structure that had been holding him together. His ratings dropped from an average of 4.5 out of 5 down to threes, twos and ones. * He wanted to start drinking again. He went to therapy instead and came out with a diagnosis of ADHD and major depressive disorder. * Leadership gave him no coaching and no useful feedback, and he couldn’t work out what was happening to him. * Between 2020 and 2024 it built into a crash, and a second suicidal episode. Key Insights “What I found out is the lack of structure was killing me and I couldn’t figure out what was wrong with me.” [21:26] Losing the Job That Was His Whole Identity * Bad reviews turned into termination proceedings. He believed it was all his fault. * He checked into inpatient care in Colorado expecting a short stay. He thought he was better, wasn’t, and stayed a second month. * In 2025, USAID was dismantled and his 17-year career ended outright. Having the job taken from him did what he couldn’t do himself. * He had stayed off social media for 20 years. Substack is where he landed after. Key Insights “I was finally able to break Steve away from Steve, the USAID worker.” [23:07] The Depression Equation * Steve built himself a simple formula for what was happening to him, and then built his day around beating it. * His answer was to get outside, so he started walking dogs. It slowly dawned on him that this could be an actual life. * Buddhist teachings on attachment had been floating around his life for years without landing. They landed now. * He got obsessed with space, and found the scale of it comforting rather than frightening. Key Insights “Depression equals being at home. Being alone and in your own head. So at home plus alone plus in your own head equals depression. It’s just an equation.” [26:02] Finding Out He Was Creative After All * Steve was a numbers guy and a spreadsheet guy who was certain he had no creativity in him at all. * Art therapy in Colorado cracked it open. He drew stick figures and it felt good anyway. * AI became the tool that closed the distance between what he could picture and what he could make. * He learned he wasn’t a burden on the people around him, a belief that had shaped how he lived for decades. Key Insights “Didn’t think I had any artistic bones in my body or any kind of creativity ever.” [33:15] Outside Feet, Artificial Idiocracy, and What Creativity Actually Is * “Outside feet” is what Steve says to his own dogs when he’s putting his shoes on. He built the company name around that instead of a pet pun. * Artificial Idiocracy started as a joke about being the average person stuck between the pro-AI and anti-AI camps. * He’s building a Renaissance-punk world of corvid characters modeled on writers he admires on Substack, studying their sites, words and mannerisms before he designs each one. * He now makes less money than he did at USAID and says he’s happier. Key Insights “It’s just being open and being honest is what I think creativity really is.” [39:07] The Dossier About forty minutes in, Steve shared his screen and showed me the character he’d made for me. I’m a rook. He picked it on purpose. Ravens are loud and shouting all the time, and as he put it, “the rooks are a little bit more introspective.” He called the character a sober artigiano, a working artisan, and drew me as a stone sculptor. His description: “creating something out of something very raw, but you’re shaping it into something beautiful.” He gave it a full dossier. Species, publication, class, a list of traits. Stone Sculptor: shapes new form by refusal. Radical Honesty: drops the alibi. Clear Hour: makes in the empty hour. Creative Reset: builds what sobriety gives back. He’d read enough of my work to pull The Alibis into a panel of its own, put the arm tattoo on the sleeve, and put me sitting in meditation at sunrise. Along the bottom it reads: Perfection isn’t the goal. Presence is. This is what he does now. He studies a creator’s work, their words and their mannerisms, and builds them a character in a Renaissance-punk world of corvids. “I studied their sights, I studied their words, I studied their mannerisms.” Then he gives it away. A man who spent 40 years certain he had no creativity in him made this. That’s the whole episode in one image. Key Quotes “For me, my entire life, my identity, my worth was tied up with my job.” — Steve “I just decided I needed to go to inpatient because I couldn’t guarantee my own safety.” — Steve “I’m not a burden to anybody. In fact, people like helping other people.” — Steve “The materialism is not the key to happiness. It is something within you and the community around you that has that happiness.” — Steve “I’m not here to promote anything. I’m just here to be myself. And that’s the greatest thing I can pick up right now.” — Steve Resources Mentioned * Art therapy — where Steve first drew anything as an adult, during his inpatient stay. * Buddhist teachings on attachment — ideas that had been around his life for years and finally took hold after he lost his job. * Corvids and the Renaissance — the two sources behind his Renaissance-punk character world. Ravens, crows, jackdaws, nutcrackers, rooks and jays. * The Clear Hour — my free monthly gathering. A short guided practice, then everyone works, then we come back and share. Where to Find Steve * Outside Feet: outside-feet.com — daily dog wellness in D.C. and Montgomery County * Artificial Idiocracy on Substack, where the corvid characters live * Mostly, he’s in the notes. In his words: “Always happy to talk with people.” What Steve’s Story Says About Structure Steve quit drinking in 2018 and stayed sober. Six years later he still crashed. What took him down was the loss of structure. No outside scaffolding, no daily contact, no one checking in on how he was actually doing. He said it plainly: the lack of structure was killing him and he couldn’t figure out what was wrong. That's the piece most people skip. They stop drinking and leave everything around it exactly as it was. The Sober Creative Reset is 30 days of structure while you take alcohol out. Four weekly 60-minute sessions with me one-on-one, daily email check-ins with a reflection prompt, trigger and pattern mapping, and tools to steady your nervous system when it gets loud. When you slip, we adjust the plan instead of starting over. It’s $497 for the 30 days, about $124 a session, and you can cancel anytime. It isn’t therapy, rehab, or A

  2. Aug 21

    Episode 066 - Walking Away From Normal

    Erin Gregory Creative did not hit rock bottom. That’s part of why her story is worth sitting with. She grew up Irish Catholic, in a family where a drink was how you celebrated and how you grieved. She was a scholarship swimmer in college, where work hard, play hard was simply the culture. She married Mike, whose family operated the same way. Nobody in her orbit thought twice about it. Then in 2018, Mike’s father died of cancer after a six-year battle, and two social drinkers with young kids at home found out what happens when grief lands on top of a habit nobody questions. Two drinks a day became three. More tired, more agitated, less motivated. Mike quit first, went to therapy, left his job, got his master’s, and started rebuilding. Erin watched that happen and asked herself a question she’d been avoiding for years. There was no dramatic moment. She just finally committed to something she’d already wanted. By 2020 they were both done. What came after took time. Mike went back to his music and now works for Habitat for Humanity. Erin built a consultancy that lets her be present for her three girls. They moved states, changed jobs, and started over in nearly every sense. In this conversation she walks through how they did it, what replaced the ritual, and why she now looks at the alcohol industry the same way she looks at tobacco. Show Notes [02:03] Where “Normal” Came From * Erin describes growing up “a good old Irish Catholic girl,” in a culture where alcohol was never discussed but always present. * In her family it was how they celebrated and how they grieved, and she never saw it as harmful. * As a young adult it became “the forbidden fruit,” then college and competitive swimming folded it into a work hard, play hard identity. Key Insight: The habits hardest to see are the ones your whole community shares. “It was really just a part of the society that I grew up in. And I never saw it as something bad or harmful.” [03:35] You Don’t Have to Hit Rock Bottom * Erin names a gray area most conversations skip past entirely. * When Mike’s father died in 2018, they were social drinkers with two young girls. Two drinks a day quietly became three. * The physical toll compounded the grief: more tired, more agitated, less motivated. Key Insight: You can be functioning and still be held back by something. “You don’t have to be a full functioning alcoholic to admit that you’ve got a problem, that something is inhibiting your life.” This is the exact gray area The Sober Creative Reset was built for. You don't need a label or a bottom to decide something's costing you more than it gives. [04:41] Mike Quit First * Mike made the decision first, and it became the start of his healing process. He went to therapy, quit his job, and got his master’s degree. * Erin had tried to eliminate it before, driven by her own guilt, but found it nearly impossible while surrounded by people who drank. * Watching Mike rebuild gave her the push. She and Mike cut it out entirely rather than saving it for special occasions. Key Insight: A moderation plan can keep the story alive. Cutting it out ends the negotiation. “I was like, why am I still holding on to this? There’s nothing in it for me. I’m literally drinking with my children.” [05:41] Seeing the Marketing for What It Is * They both read a book on alcohol, one edition written for men and one for women, and the contrast opened their eyes. * They drew a direct line between the alcohol industry and tobacco, the industry Mike had been supporting at work and hated. * From there they started looking at fast food the same way, and noticed how much of what they consumed had been sold to them as fun and celebratory. Key Insight: The advertising is designed to attach a numbing agent to your proudest moments. “All of the advertisement is like, this is a celebration. You should have something that basically numbs you from the reward that you just earned through your hard work. It’s so backwards.” [08:05] The Ritual Is What You Miss * Erin says what you actually lose is the end-of-day marker, the signal that you’re allowed to relax. * They had to build other things into that space. * At parties they bring their own fizzy water, mostly because their not drinking tends to bother other people more than it bothers them. * Since the pandemic she’s watched sober initiatives grow and the narrative start to shift. Key Insight: Replace the ritual, not just the drink. “They say it’s not like the alcohol itself you miss. It’s the ritual.” [11:10] Raising Kids Around It * Their kids were eight, five, and two when they stopped, around 2020. * Erin and Mike deliberately keep alcohol from becoming taboo in their house. Extended family still drinks on occasion, and the girls see it. * The goal is informed choice at 21 rather than a forbidden thing that gets unlocked on a birthday. Key Insight: Kids don’t need a rule. They need to watch you make a decision you can explain. “We don’t want it to seem like this forbidden fruit or like you turn 21 and you get to have it. You’ll have the freedom to make that choice when you’re of age and I hope you make the choice that is best for you.” [14:32] What Actually Changed at Home * Erin is clear that the alcohol never caused bad behavior. What it caused was guilt, the kind you carry around doing something you can’t explain to your kids. * Removing it meant they stopped hiding and stopped masking. * The relationships got better because she and Mike simply felt better about themselves. Key Insight: Guilt sits heavier on a household than the drink itself. “I think our relationships with them are better because we just feel better about ourselves. We’re living more honestly. There’s not trying to hide things or mask things.” [15:42] The Third Space * Erin defines a third space as somewhere you go that belongs only to you and your own well-being. * Hers used to be marathon running. Injuries pushed her to evolve it into gardening and walking. She dug up half her backyard after a hard family stretch and now has more than 300 plants in the house. * She points to the YMCA and group fitness as accessible options, and to community service as the other half of the equation. Mike works for Habitat for Humanity and volunteers on an arts board. * Her reasoning: depression tends to grow when you’re stuck inside your own world. Key Insight: Pick coping tools that pay you back instead of charging interest. “Addressing life’s challenges with something that is going to better you in the end, instead of make it harder to deal with.” [24:59] Advice for Anyone Making the Decision * Erin is direct about the trap of tapering. A drink on Friday becomes a drink on Saturday, then Sunday, then a fresh restart on Monday. * Find your resource. For them it was the books plus each other for accountability. She notes friends who’ve found real success in AA, including one who introduces herself as a recovering alcoholic in every new room so the boundary is set from the start. * Josh shares his own turning point at [28:04]: stopping mid-workout at Orange Theory, out of breath, and telling the coach he’d drunk too much the night before. It took two more years of tracking and research before he committed on August 19, 2020. * Erin’s larger point is that the motivation has to be yours. Theirs was their kids. Key Insight: Make one clean decision instead of a hundred small ones. “Whatever that motivation needs to be for you, figure it out and then just make that decision and don’t look back.” Key Quotes “You don’t have to be a full functioning alcoholic to admit that you’ve got a problem, that something is inhibiting your life.” — Erin Gregory “It still felt like we were treating it like a reward or a healing mechanism when we knew it was anything but.” — Erin Gregory “The last answer I wanted to get them was, Mommy, why are you drinking that? Because there’s no good answer for it.” — Erin Gregory “It’s not even that the alcohol caused bad behavior. It was just the guilt that you kind of carry along with it.” — Erin Gregory “We just built a life with intention instead of subscribing to what we had been exposed to in the past.” — Erin Gregory Resources Mentioned * This Naked Mind by Annie Grace — the book that helped Josh transition * Allen Carr's Easy Way to Control Alcohol — Erin and Mike each read an edition written for their own gender * The third space — Erin’s framework for a place free of responsibility to anyone but yourself * The YMCA and group fitness classes as accessible community * Habitat for Humanity — where Mike works now * AA and Recovery Dharma — Josh facilitated a Recovery Dharma meeting for several years * Erin’s forthcoming memoir and companion workbook, distilling the work she does with clients on building income in the margins Where to Find Erin Erin Gregory writes The Self-Led Life on Substack, where she covers workforce structure, meaningful work, and building a career around your life instead of the reverse. She runs a brand consultancy supporting mission-driven organizations, plus a personal branding and coaching practice for people who want to restructure the work they’re in or build something with more room in it. She’s also delivering workshops and keynotes to college students and recent graduates. “My mission, is to bring awareness to the possibility that is out there if you can think strategically and creatively about your career journey and not just accept what’s on paper.” — Erin Gregory Ready to Find Out What’s Underneath? Erin’s story lands because nothing had fallen apart. She was functioning. Two social drinkers, three kids, jobs handled. And underneath it, something was inhibiting her life. She also named the loop exactly: a drink on Friday becomes a drink on Saturday, becomes a drink on Sunday, then Mo

  3. Aug 14

    Episode 065 - What Recovery Gives You Back: A Conversation with Hunter Biden

    In this episode, Josh sits down with Hunter Biden, a painter and writer based in Los Angeles who built a first career in law and business long before most people knew his name for anything else. Then one October, a laptop turned his private life into public property overnight. Every family photo, every relapse, and every unfinished thought got picked up by strangers and rearranged into a story he never wrote. What makes this conversation stand out is how plainly Hunter talks about the parts most people would keep hidden. He calls addiction “never an excuse,” but insists it can be an explanation. He traces almost every bad decision he’s made back to fear. He talks about the accident that killed his mother and sister when he was three years old, the decade of relapse that followed his first stint in rehab, and the moment a total loss of privacy left him with what he calls a binary choice: get up and live, or find a way to die. By the end of the conversation, Hunter has moved past the scandal. He talks about a paintbrush his wife Melissa bought him at a used furniture shop, about finding purpose in a single afternoon of painting, and about why being of service to other people secures his sobriety more than anything else. This is a conversation about what happens after the worst thing you can imagine happens to you, and what you build with what’s left. Show Notes [00:00] Meet Hunter: From Scandal to the Studio * Josh introduces Hunter as someone whose entire digital life was leaked from a laptop one October, turning private photos, relapses, and unfinished thoughts into a story other people wrote for him. * Seven years ago, at a point where Hunter says he could no longer trust his own mind, he picked up a paintbrush and started working in alcohol ink, acrylic, and Pointillism. * Hunter now paints in Los Angeles and writes about his experience on Substack, correcting himself in public when his memory proves him wrong. Key Insight: “That was the most beautiful introduction I’ve ever gotten.” - Hunter [02:08] A Beautiful Childhood, Filled With Trauma * When Hunter was about three, he and his older brother Beau were in a violent car accident with their mom and little sister. Rescue workers used the jaws of life to free them. * Hunter’s mother and sister died in that accident. He and his brother spent a month or more in the hospital together afterward. * His Aunt Valerie, Uncle Jimmy, and the rest of his family rushed in to rebuild their lives, and Hunter calls his dad “the best dad I know.” * For years, Hunter didn’t let himself believe that early trauma played a role in what came next. Key Insight: “I had an incredibly beautiful childhood filled with trauma.” - Hunter [05:01] The First Drink and the Cycle of Shame * Hunter remembers his first sip of alcohol at age eight, sneaking a champagne flute at a party and feeling like everything missing in him had suddenly been filled. * His drinking progressed through high school and college, and he went on to graduate from Yale Law School. * By his early thirties, Hunter knew his drinking wasn’t normal. He made himself promises: only drink on weekends, only drink beer, no Jack Daniels. He broke every one of them. * Breaking those promises started a cycle of shame that became, in his words, the thing that locked him into relapse. Key Insight: “When I would break that promise, I decided it was easier to hide that and lie about it than be honest with myself or anybody around me.” - Hunter [07:42] Rehab, Relapse, and the Ten-Year Spiral * On September 12, 2003, Hunter’s brother told him he needed to do something about his drinking. Hunter went to rehab and stayed sober for close to seven years. * After his first relapse, Hunter entered a ten-year cycle that got progressively worse, moving through rehab, short stretches of sobriety, and binges. * The spiral ended in a serious addiction to crack cocaine alongside daily heavy vodka drinking, which continued for about two years before Hunter got sober in June 2019. * He’s careful with his language today. He calls himself “substance free and sober,” not “clean.” Key Insight: “More than anything, though, what I learned is that I wasn’t alone.” - Hunter [13:56] Radical Honesty Requires Radical Self-Love * Hunter talks openly about the parts of his story most people keep private, including smoking crack and being in situations involving prostitutes. * He believes addiction is never an excuse for behavior, but it can be an explanation, both to other people and to yourself. * He credits an idea from Chase Hughes: real healing takes being “almost delusional in your self-forgiveness,” without giving up accountability or the work of making amends. Key Insight: “Until you can truly love yourself, it is almost impossible to truly accept and receive love.” - Hunter [15:43] Seen and Not Abandoned: How Love Rebuilt Him * Hunter says his healing began when he let one person, his wife Melissa, see every part of him, and she didn’t run. * Melissa helped him detox at home instead of going back to rehab. Hunter describes her as becoming his “jailer” for a period of time, a role he says was painful for her to take on. * His family, especially his daughters and his dad, never closed the door on him, which is what let him find a moment of clarity and walk through it. * He’s clear that unconditional love isn’t love without accountability. It still requires making amends. Key Insight: “Unconditional love does not mean love without consequences. It does not mean love without accountability.” - Hunter [21:39] Fear, the Leak, and the Greatest Gift He Ever Received * Hunter says nearly every bad decision he’s made, sober or using, came from fear: fear of being found out, fear of underperforming, fear of not being lovable. * In October, someone stole 20 years of his digital footprint and presented the most damaging images and words to the world without context, stripping away his privacy completely. * That total loss of privacy left him with what he calls a binary choice: get up and live, or find a way to die. He says he knew he didn’t have another relapse left in him. * Today, Hunter says he doesn’t fear anything or anyone, because there’s no secret left that hasn’t already been exposed. Key Insight: “The thing that people believe was the most humiliating, and it was, and the most devastating, in many ways it was, and the most destructive, in many ways it was, was also the greatest gift that I ever received in my life.” - Hunter [28:04] The Paintbrush, the Purpose, and Peak Path Health * After detoxing at home, Melissa bought Hunter a used table, a roll of Yupo paper, alcohol inks, and acrylics from a furniture shop, and told him he needed to paint. * Hunter says having his hands occupied for hours at a time gave him something the ritual of using had trained into him: focus, and a way to get out of his own head. * He believes art only becomes art once it’s shared with another person, and that finding a small, “lowercase p” purpose in each day matters more than chasing one big Purpose. * He’s now building Peak Path Health, a recovery organization focused on the continuity of care people need after the first 30 days of treatment, alongside his Substack writing. Key Insight: “There’s nothing that secures my sobriety more wholly and completely than being in service to somebody else.” - Hunter Key Quotes “I had an incredibly beautiful childhood filled with trauma.” - Hunter “When I would break that promise, I decided it was easier to hide that and lie about it than be honest with myself or anybody around me.” - Hunter “Until you can truly love yourself, it is almost impossible to truly accept and receive love.” - Hunter “The thing that people believe was the most humiliating, and it was, and the most devastating, in many ways it was, and the most destructive, in many ways it was, was also the greatest gift that I ever received in my life.” - Hunter “It’s a practice until you share it.” - Hunter Resources Mentioned * Alcohol ink, acrylic, and Pointillism — the materials and techniques Hunter uses in his large-scale paintings * Yupo paper — the material Melissa first bought him to start painting * Peak Path Health (peakpathhealthfoundation.org) — the recovery organization Hunter is helping build, focused on continuity of care after the first 30 days of treatment * HunterBiden.com/recovery — an anonymous space where people can share their own experience, strength, and hope with addiction * Chase Hughes — referenced for the idea of being “almost delusional in your self-forgiveness,” and for the observation that “do not be afraid” is the most repeated phrase across Scripture Where to Find Hunter * Peak Path Health: peakpathhealthfoundation.org * HunterBiden.com/recovery Thank You A heartfelt thank you to everyone who joined us live for this conversation, and to Hunter for his extraordinary honesty and courage. Your presence and engagement make these conversations possible. Closer Than It Looks Hunter’s story played out in public, but the shape of it is familiar to a lot of us: broken promises, shame that keeps you hiding instead of asking for help, the day you finally decide to get up and live instead of just get through it. I knew my mornings were getting harder to show up for, and I was tired of pretending that was normal. If that’s where you are, The Sober Creative Reset is built for exactly this moment. It’s a guided 30-day alcohol-free reset with one-on-one coaching from the first session, four sessions a month, plus daily support in between. The goal is simple: give yourself a real chance to feel like you again. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit newsletter.thesobercreative.com/subscribe

  4. Aug 8

    Episode 064 - The Second Time It Stuck: Dana Kay on Becoming a New Person, Not Just Stopping a Behavior

    Dana Kay’s first memory of alcohol is from a dinner party when she was five or six years old. She spent the night sneaking sips while the adults were turned away in conversation, and by the end of the night she’d passed out on a beanbag in the middle of the room. Nobody worried. Everybody laughed. It became a family story people told for years, and it planted something in her that took over four decades to undo. By the time she reached her late 30s and early 40s, that early fascination had turned into two DUIs, years of drinking vodka out of water bottles during real estate inspections, and a daily system so precise she could stay “sober” for the school bus pickup every single day. She went to treatment twice in 2016. The first stay didn’t hold. The second one did, and it changed the entire direction of her life. In this conversation, Dana walks through what actually separated her two attempts. It wasn’t willpower, and it wasn’t a stronger program. It was the difference between trying to stop a behavior and committing to becoming a completely different person. As she approaches her ten-year sobriety anniversary on September 1st, she shares what that shift required, what she had to grieve along the way, and why she stopped trying to fit her writing into one tidy niche. Show Notes [00:00] Welcome and Introduction Josh introduces Dana Kay as a writer, connector, and nurturer who’s been alcohol-free for over nine years, and the two immediately find common ground. * Dana has been alcohol-free for nearly a decade, with her ten-year mark landing on September 1st * Josh and Dana discover they’ve both had a DUI, and neither of them remembers much of the night it happened * The tone is set early: honest, unpolished, and willing to go straight into hard material Key Insights: “I got the police report in the mail... and I was reading the police report going, that happened? I didn’t remember.” - Dana Kay [02:11] Growing Up “Cute Little Dana” Dana traces her drinking back to childhood, growing up the youngest of eight (two big brothers, five step-siblings) between two very different father figures after her parents’ divorce. * She had a well-provided-for upbringing but didn’t recognize it until she started paying her own bills * She followed “the expected track”: graduated high school at 17, college at 21, became an elementary teacher, then moved into real estate in 2006 * She names her own talent and ability to always get hired as a “double-edged sword” that fed her drinking later on Key Insights: “You can over-rely on your achievements and your talents... and that definitely played into my alcohol use for sure.” - Dana Kay [04:43] The Beanbag Story Dana describes her first conscious memory of alcohol in detail: sneaking sips at her parents’ dinner parties around age five or six, and passing out on a beanbag while the adults laughed above her. * Her parents didn’t send her to bed during parties; instead they gave her small jobs, like bringing guests drinks, which kept her in the room * She picked up early that drinking was “the absolute cool thing,” because she saw adults enjoying it and wanted to feel what they felt * Looking back as a mother herself, she’s had to reckon with recreating some of the same environments for her own kids without realizing it at the time Key Insights: “Instead of worrying or being sad, they were laughing. And they thought it was really cute.” - Dana Kay [09:22] College and the Double Life At UC Davis, Dana joined a Christian youth group (originally because the boys were cute) and found faith on a retreat at 18. But she kept a second, separate version of herself for home. * Her day-to-day life revolved around a sober Christian friend group, while trips back to her hometown meant drinking, flirting, and partying * She describes the pull of that split identity as its own addiction: “The complete rush was, what can I get away with?” * After friends celebrated that she’d “never party again,” she made a conscious decision in the car to keep that part of her life hidden from them going forward Key Insights: “It was a complete rush, more than alcohol itself. The complete rush was, what can I get away with?” - Dana Kay [15:00] The Rock Bottom Years By her late 30s, working in real estate, Dana’s drinking became a fully hidden system built around her family’s schedule. * She lied to her husband about needing to “drop off flyers” or run open houses so she could go drink, and he had no way to track her irregular real estate hours * She drank vodka out of water bottles during home inspections for over a decade, including with an inspector she’d known for 15 years who never suspected a thing * She built a daily rhythm: sober and present for morning drop-off, drinking through the day, then timing a nap so she’d appear sober again by the time her sons got off the bus * One morning in late August, her organs seized and she couldn’t move out of bed; she still told her husband she “just had a tummy ache” before he left for work Key Insights: “That energy of wanting to get away with it, and fooling everyone, lived more in me than the substance did.” - Dana Kay [17:49] First Treatment vs. Second Treatment Dana explains the moment that sent her to treatment the first time, the relapse that followed, and the deeper shift that made the second stay permanent. * Her therapist stopped a session mid-conversation and said, “we can’t get any further until you’re honest about alcohol,” which Dana had been carefully avoiding * That night she Googled “how do you know if you’re an alcoholic” and discovered she’d searched the exact same thing on Christmas Eve, in a blackout she had no memory of * After four sober months following her first treatment, she relapsed on a trip to Europe with her son, telling herself a little drinking wouldn’t turn permanent * The second time she got sober, a therapist helped her see the real difference: the first attempt focused on stopping a behavior, while the second required building an entirely new identity Key Insights: “If you’re going to be successful at this, you have to have an entirely new identity.” - Dana Kay [34:29] Building the New Identity Dana describes the practical, unglamorous work of rebuilding her life around the new identity, not just the absence of alcohol. * She had to consciously change her driving routes because her car would automatically head toward familiar bars * She built accountability into her schedule by not leaving gaps between appointments, and leaned on close friends and her husband to hold her to it * She started a morning journaling practice, writing down small changes so she could reread her own words later, on the days she felt weak * She noticed real physical changes, like hitting new personal records at the gym, and had to stop denying that sobriety was the reason Key Insights: “No, Dana, you know that this is going to lead to that. This feels so much better. You wrote it right here.” - Dana Kay [38:07] Noticing, Grief, and the Sunrise Dana connects her recovery to a growing capacity to actually notice her life, and the grief that came with realizing how much she’d missed. * She began noticing details on ordinary drives, like trees, mountains, an eagle, or a deer, that she says she never used to see * She describes a memory of watching a sunrise in Mexico while drinking, and realizing only in hindsight that it was really “a place to go hide and drink” * She’s come to believe that grieving what was missed isn’t just okay, it’s a necessary part of the process * She also became more honest in her business relationships, without the manipulation she now recognizes she’d been running for years Key Insights: “Not only is it okay to grieve that, it’s important to grieve that.” - Dana Kay [41:11] Family Roots, What She Writes Now, and Where to Find Her Dana closes by connecting her story to her family’s long history with alcoholism, and explains what she writes about today. * Her grandparents were pillars of the local AA and Al-Anon community, and she grew up helping serve pie and coffee at their meetings, even while her own aunt struggled with alcoholism without full openness from the family * After years of trying to force her writing into one niche, she’s landed on a simple framework: Connection, Acceptance, and Noticing (C-A-N) * She writes about sobriety, motherhood of older kids, being single in your 50s, and starting over later in life, all under what she calls the umbrella of love * She’s active on Substack and Instagram as Dana Kay, offers one-on-one calls, and leads gratitude and connection sessions at retreats she’s invited to Key Insights: “There is no saying no to whatever your dreams are, whatever you want to do with your life. There’s just no no.” - Dana Kay Key Quotes “The complete rush was, what can I get away with?” - Dana Kay “If you’re going to be successful at this, you have to have an entirely new identity.” - Dana Kay “My identity took me into relapse because I still wanted to be the pretty, fun, cool girl, mom, friend, daughter.” - Dana Kay “Not only is it okay to grieve that, it’s important to grieve that.” - Dana Kay “There is no saying no to whatever your dreams are, whatever you want to do with your life. There’s just no no.” - Dana Kay Resources Mentioned * Gabor Maté’s approach to addiction — Dana references his idea that instead of asking “where’s the addiction,” you ask “where’s the pain” * AA (Alcoholics Anonymous) and Al-Anon — the community Dana’s grandparents helped lead, which shaped her early exposure to recovery * Dana’s C-A-N framework — Connection, Acceptance, and Noticing, the three principles she now writes and coaches around Where to Find Dana Kay * Instagram: Dana Kay * 1:1 Calls: Dana offers personal calls for a

  5. Aug 2

    Episode 063 - Jomo the Meditating Monkey: Stillness, Sobriety, and the Busy Mind

    Most guests on this show are people who found their way to sobriety and creativity through hard-won trial and error. This week’s guest is a small golden monkey in a patchwork waistcoat who has never had a drink in his life. His name is Jomo, and he teaches meditation to millions of people on TikTok alongside his human, Jason, at The Monkeymind Meditation Club. Jomo’s origin story starts with Jason hitting a wall. He liked to drink and party until, as Jomo put it, “the bottom of the barrel was in sight.” Meditation pulled him out of it, and it worked so well that Jason wanted to teach it to others. The problem was that meditation looked strange and unapproachable to most beginners. So Jason built a version anyone could try, and gave it a monkey mascot to make the whole thing feel less intimidating and more human. What Jomo shared in this conversation goes far beyond breathing techniques. He talked about why the mind is the most important tool we have, why meditation is less about being calm and more about clearing the noise so calm can show up, and why he believes people who choose sobriety are some of the bravest people alive. If you have ever avoided sitting with your own thoughts, this one is for you. [00:50] Meet Jomo, the Meditation-Teaching Monkey * Jomo is the mascot and co-teacher behind Monkey Mind Meditation, run alongside his human, Jason. * The name plays on “monkey mind,” a term meditation teachers use for the constant jostling of thoughts and feelings we all deal with. * Jomo’s approach centers on making meditation feel ordinary instead of mystical or hard to access. Key Insight: “Hello, it’s lovely to be here.”— Jomo [03:05] From Rock Bottom to Monkey Mind: How the Journey Began * Jason struggled with drinking and partying before finding meditation as a way out. * Learning to meditate changed his life enough that he wanted to teach it to others. * Early students were put off because meditation online looked strange — people in odd positions, dramatic backdrops, nothing relatable. * Jason built a simpler, friendlier version of meditation and gave it a monkey mascot to make it approachable. Key Insight: “He liked to drink and he liked to party. And he realized that the bottom of the barrel was in sight.”— Jomo [05:55] Two Million Meditators: Growing an Audience on TikTok * The show started rough. Early viewers were confused and sometimes rude about what they were watching. * Growth was slow at first, then it exploded into hundreds of new viewers every week. * They’ve now done over 600 live sessions and reached more than 2 million people through TikTok. * New viewers tend to follow the same pattern: confusion, then curiosity, then commitment. Key Insight: “When they first come on, they think to themselves, what is this? And then they put the little acronym, WTF, which is a bit rude. But we stick with it. And then a few minutes later, they may say, oh, this is actually quite calming. And then a few minutes later, they’ll say, this is actually working. And then a few minutes later after that, they say, when are you next on? And then they’re a fan.”— Jomo [09:05] Why Your Mind Is the Most Important Tool You Own * Jomo argues the mind shapes the quality of everything else in life, including how we experience reality itself. * He points out that nobody gets a manual for how their brain works. * He describes meditation as a kind of daily software upgrade for the brain. * He calls the practice “a force field for good mental health” that needs to be recharged regularly, since life keeps throwing things at us. Key Insight: “I call it a force field for good mental health. Every time we meditate, we recharge that force field.”— Jomo [11:10] Sitting With the Monsters: Meditation and Sobriety * Jomo believes people on a sober journey are some of the bravest people around. * He connects addictive behavior to an unwillingness or inability to face what’s going on inside our own heads. * Meditation, in his view, is a way to sit with the parts of ourselves we normally avoid or numb. * He argues meditation doesn’t create calm directly. It removes noise, and calm follows from that. Key Insight: “Meditation helps us look inside. And sit with the monsters. And then when you sit with the monsters, you realize that the monsters just want to be heard. And when the monsters are heard, they go away.”— Jomo [13:32] Think Away: Making Meditation Approachable for Everyone * Jomo teaches people that trying to stop thinking is impossible, and fighting that fact just creates frustration. * Instead of suppressing thoughts, his method is to notice them and gently return to the breath or a mantra. * He reframes a common complaint — “I can’t meditate because my mind is too busy” — as the exact reason meditation is needed. * The format is deliberately ritualized (three deep breaths to start, a wriggle and stretch to close), which he says works especially well for their autistic community. Key Insight: “We teach people that you can’t stop thinking. That’s impossible. It’s like saying, don’t think of a pink elephant. And the first thing you do is you think of a pink elephant. So what we say is, think away. That’s okay. We’re not going to thought shame you here.”— Jomo [16:56] A Live Guided Meditation With Jomo * Jomo led a short mindfulness meditation live on the show, starting with three deep breaths. * The meditation focused on noticing thoughts without following them, comparing them to leaves floating past on a river. * He guided listeners toward the idea that we are the awareness watching our thoughts, not the thoughts themselves. * Several listeners in the chat reported feeling calmer immediately afterward. Key Insight: “And begin to sense that this breath is not something you’re doing, but something that’s happening to you.”— Jomo [26:03] Beyond TikTok: Variety, Reactions, and Where to Find Jomo Next * TikTok’s algorithm reportedly struggles with their content because viewers stop interacting while meditating. * Jomo shared a story about teaching meditation to someone with road rage, who learned to notice his anger instead of being swept up in it. * Their live sessions mix different formats: mindfulness meditations, Zen stories, visualization journeys (Peru, Morocco, even an imagined “Land of Cake”), and a loving kindness meditation to close things out. * They go live on TikTok Mondays, Wednesdays, and Fridays, and have recently started YouTube lives on Sundays at 9pm, with all past sessions archived on YouTube. Key Insight: “We start with a mindfulness-based meditation, then quite often we’ll have a little bit of a Zen story, and then after that we have a visualization meditation, so we go to ancient Peru, Morocco, or the Land of Cake we did the other day. And then we finally give people a taste of a loving kindness meditation at the end so that they go away feeling full of good vibes.”— Jomo Key Quotes “When you sit with the monsters, you realize that the monsters just want to be heard. And when the monsters are heard, they go away.”— Jomo “It doesn’t make you calmer. It just takes away the noise. Calm follows.”— Jomo “And people say, I can’t meditate because my mind is too busy. To which we say, that’s like saying, I can’t go to the gym because I’m too unfit.”— Jomo “There’s nothing to achieve here. Nothing to get right. Just a soft arriving into this moment.”— Jomo “You’re not the passing thought. You’re the awareness that sees it. You’re not the changing story. You’re the space in which it appears.”— Jomo Resources Mentioned * Monkey Mind Meditation — Jomo and Jason’s meditation practice, live on TikTok and YouTube * Transcendental Meditation — the practice mentioned as Josh’s own current meditation approach * Vedic meditation — the tradition Jason teaches, described as closely related to Transcendental Meditation Where to Find Jomo * TikTok: Live sessions Monday, Wednesday, and Friday * YouTube: Live sessions Sunday at 9pm, with all past recordings archived Thank You A heartfelt thank you to everyone who joined us live for this conversation, and to Jomo for his humor, warmth, and unexpected wisdom on what it actually takes to sit still. Your presence and engagement make these conversations possible. A Natural Bridge Jomo’s whole philosophy comes down to one idea: meditation doesn’t hand you calm directly, it clears the noise, and calm shows up on its own once the noise is gone. That’s the same principle behind alcohol and creativity. Alcohol is often the tool people reach for to avoid sitting with what’s actually happening in their heads. Removing it doesn’t hand you clarity right away either. It clears space, and clarity tends to follow from there. If this episode stirred something for you and you're ready to do that work with support instead of alone, I coach a small number of people 1:1 through exactly this process. Send me a message at and let's talk about what that could look like for you. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit newsletter.thesobercreative.com/subscribe

  6. Jul 24

    Episode 062 - Music Is The Centerpiece Of My Life, Alcohol Is Not

    Jeff “H” Harrington has been playing bass and writing songs for close to 40 years. He grew up in Milwaukee, a city he describes as one of the heaviest drinking cultures in the country, and spent his 20s and 30s using alcohol to manage a shyness he calls “criminally vulgar.” Nine years ago he left a career in medical physics to chase music full time. Five years ago, he stopped drinking almost entirely. What makes Jeff’s story worth sitting with is what he found on the other side. He didn’t just give up alcohol. He learned he’s deeply introverted, sensitive to noise and to the energy of a crowded room, and far less interested in big social gatherings than he ever realized while drinking. He also traded songwriting as an emotional release valve for something different: chant music built on ancient mantras, made to help people feel calm and present rather than to process pain. In this conversation, Jeff talks about growing up in a drinking culture so strong it shaped an entire state’s identity, why his own drinking nearly disappeared the moment he lived somewhere else, and how a stomach problem sealed a decision his body had already started making on its own. He also shares a theory about sad music that’s worth thinking about, whether you drink or not. [1:36] Meet Jeff Harrington: Musician, Nine Years Removed From a Left-Brain Career * Jeff is a singer, songwriter, producer, and bass player who’s been gigging for close to 40 years, much of it in the blues scene. * Nine years ago he left his career as a medical physicist to focus on music, even though it’s never been his main income. * He’s five years sober and has pulled back from playing out live, a shift he traces directly to sobriety. Key Insight: “We’re supposed to do what we’re really terrified of, aren’t we?” [3:03] Growing Up in Wisconsin’s Drinking Culture * Jeff grew up in Milwaukee, which he says ranks nationally for excessive drinking, DUIs per capita, and bars per capita. * College at Madison took that culture to another level. He describes drinking at least 12 beers a night as normal for everyone around him. * He used alcohol to manage deep shyness and social anxiety, comparing it to an athlete numbing an injury just to get through the game. Key Insight: “I think I was literally, my growth was stunted for at least five or 10 years looking back.” [7:07] The Cleveland Contrast * When Jeff moved to Cleveland for his first job, he expected a similar drinking culture to Wisconsin. Instead, he found people drank far less, and so did he. * Looking back, this showed him how much of his drinking had been shaped by the environment around him, not by who he actually was. * When he moved back to Wisconsin, he eventually fell back into the same heavy drinking patterns. Key Insight: “I didn’t drink that much when I was in Cleveland. So looking back, I see that that’s who I really was.” [13:48] Discovering He’s an Introvert * After quitting drinking, Jeff realized he’s extremely introverted and sensitive to noise and to the energy of the people around him. * He’s meditated for about 15 years, which he thinks has made him more attuned to these subtler energies. * His social life shifted from crowds to small, comfortable gatherings that don’t leave him exhausted the next day. Key Insight: “I’m not somebody who’s going to want to go to a party at this point or any place that’s loud and crowded.” [15:54] A Stomach Issue Sealed What Had Already Begun * About 10 years ago, Jeff and his then-girlfriend already cut back on drinking a lot as they got more into health. * About five years ago, a stomach issue made alcohol physically intolerable, arriving right as he was already drinking less. * Today he has maybe three or four drinks a year, and calls it fully intentional rather than something he misses. Key Insight: “If my stomach magically healed, I wouldn’t be drinking at all. I don’t like it in my life anymore.” [17:09] From Songwriting as Therapy to Chant Music as Calm * In his 20s and 30s, Jeff used songwriting as one of his only tools for processing intense emotion, since he felt culture raised men to stay disconnected from their feelings. * Today he writes mostly chant music on his Substack, Inside Sky Chant, built around ancient mantras rather than English lyrics. * The purpose of his music has shifted from emotional catharsis to something more utilitarian: helping listeners feel calm and present. Key Insight: “The ultimate goal would be it’s music that would be used to help people just be more calm and maybe present.” [22:50] A New Earth: Spiritual Growth and Sobriety Growing Together * About 15 years ago, Jeff read Eckhart Tolle’s A New Earth, which he says completely changed his life after years of searching without finding a way in. * That book led him toward chant music, sound baths, and a spiritual practice he sees as deeply tied to his relationship with alcohol. * He’s careful to say this isn’t about judging people who drink. For him personally, alcohol just no longer serves what he’s trying to build. Key Insight: “I think the spiritual growth and the alcohol are very interconnected.” [28:23] The Hangover, the Brain, and a Theory About Sad Music * Jeff and Josh discuss how alcohol triggers inflammation in the body, which is part of what a hangover actually is. * They talk through how alcohol can worsen depression and how the brain’s negativity bias, combined with modern stressors like social media, feeds a cycle of using alcohol to regulate the nervous system. * Jeff shares a personal theory that he became addicted to sad music the same way people get dependent on alcohol, reaching for it out of habit rather than need. Key Insight: “I think if people are listening to sad music every day, I really would suggest trying to step back and take a look at that.” Key Quotes “I think that’s like a perfect analog to someone who’s shy and they’re drinking.” - Jeff Harrington “I was someone who didn’t even really want to drink that much. I was probably very influenced by the culture around me.” - Jeff Harrington “I found out so clearly that I’m extremely introverted and sensitive to all the noise.” - Jeff Harrington “If my stomach magically healed, I wouldn’t be drinking at all. I don’t like it in my life anymore.” - Jeff Harrington “I really feel more and more, I feel like people really underestimate how powerful music is.” - Jeff Harrington Resources Mentioned * A New Earth by Eckhart Tolle * Release Your Song (Jeff’s Substack on music and creativity) * Inside Sky Chant (Jeff’s Substack for his chant music) * Handpan (the instrument Jeff and Josh discuss in relation to nervous system regulation) * Sound baths (a guided meditation practice using instruments like handpans) Where to Find Jeff Thank You A heartfelt thank you to Florence Acosta, Noelle Richards, Peter, and many others who joined us live for this conversation, and to Jeff for his openness and generosity in sharing his story. Your presence and engagement make these conversations possible. What This Conversation Points To Jeff and Josh spent a good chunk of this episode on something worth pulling out on its own: the cycle of reaching for alcohol the moment an uncomfortable feeling shows up, because it soothes that feeling within minutes. Jeff broke that cycle on his own timeline, over years, without a program or a guide walking alongside him. That’s exactly where 1:1 coaching comes in. If you’re recognizing that same cycle in your own life and you’re ready to shorten the timeline, let’s talk. No pitch, no commitment. Just a conversation about where you’re at and what might be possible. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit newsletter.thesobercreative.com/subscribe

  7. Jul 17

    Episode 061 - It’s Getting in My Way Now: Gary Allen on Slow Change and Building a Second Act After 45

    Gary Allen had his first drink at 19, a pint of Harp he didn’t even like. He kept drinking it anyway, because for the first time, he felt like everybody else. Gary grew up in rural Ireland, the oldest of three, and has used a wheelchair full-time since he was 13. Alcohol became the thing that closed the distance between him and the room. He didn’t fully realize that’s what it was doing until decades later. For 26 years, drinking looked completely normal. Nights out with his brothers turned into nearly 20 years of sharing wine on the couch with his wife. Nothing about his life looked broken. He had a steady IT career, a mortgage, and a stable home. At 45, he just noticed something simple: it was getting in his way now. That one observation, made on a flight home from Barcelona in January 2018, led him to commit to 100 alcohol-free days. He hasn’t had a drink since. Within weeks, he stumbled onto a coaching course and knew almost instantly it was where he belonged. Nearly nine years later, at 54, Gary runs his own practice, the Life Design Collective, helping people in midlife ask the same question he once asked himself: is this it, or is there something else? [03:06] Growing Up Different in Rural Ireland * Gary was born and raised in rural Ireland and has used a wheelchair full-time since age 13. * He didn’t have his first drink until 19, well past the age most of his peers started. * Drinking made him feel like part of the group in a way he hadn’t before, since he grew up looking different from everyone around him. Key Insight: “It just made me feel like everybody else.” [07:04] The Wake-Up Call at 45 * His drinking shifted over time: nights out with his brothers in his 20s, then almost 20 years of sharing wine with his wife on the couch. * Nothing about his life looked dramatic. He had a steady job, paid his bills, and everything seemed fine on the surface. * At 45, he simply noticed alcohol was in his way and decided to see what life looked like without it. Key Insight: “It’s getting in my way now.” [07:46] From IT Career to Full-Time Coach * On a flight home from Barcelona in January 2018, Gary committed to 100 alcohol-free days. He never had another drink after that. * Within about two months, he found a coaching course and knew right away it was what he wanted to do. * He ran two full workloads at once (coaching and his IT job) for years before finally leaving tech in 2023 to coach full-time. Key Insight: “I didn’t actually go, okay, I’m quitting my job and I’m going to sell a house and move to Bali.” [10:57] The Pattern Behind Change That Sticks * Most people start by naming what they don’t want: hangovers, health problems, tension at work or at home. * Once that clears, the real work begins, which is figuring out what you’re actually moving toward. * Change rarely works on the first try. Every attempt adds information, and the streaks get longer as people learn instead of judging themselves for slipping. Key Insight: “It doesn’t ever really work the first time.” [13:04] Curiosity Over Judgment * Gary calls curiosity, instead of self-judgment, the biggest shift he sees in people who make change last. * Instead of asking why they failed, the useful question becomes what they could try differently next time. * This mindset reaches far beyond drinking. It’s the difference between staying stuck in a cycle and actually moving forward. Key Insight: “If you can treat it with curiosity and not judgment, that’s the real game changer.” [17:00] Creativity, Clarity, and Finding Substack * Gary spent almost 30 years in software, which he describes as genuinely creative work, even though it was never quite the right fit for him. * About six weeks into sobriety, he experienced a level of energy and clarity he’d never felt before. * That clarity opened the door to writing. He’s been on Substack for close to two years and is nearing one full year of his weekly newsletter, Second Act Sunday. Key Insight: “Creativity almost by default jumps in.” [21:02] What Happens When the Numbing Stops * Removing alcohol doesn’t remove hard feelings. It just means you feel all of them, not only the ones you’d pick. * Gary resisted gratitude journaling at first. “Thank you very much, I’ll pass,” he says of being told to write down three things he was grateful for. * The practice ended up helping him see what he already had and who he already was, built by parents who raised him to believe he could do anything. Key Insight: “It did allow me to kind of see what I have and see who I am.” [29:19] Building a Second Act After 40 * Gary pushes back on the idea that life needs to be fully figured out by 40, and that any change after that is too hard or too late. * His program, the Second Act Blueprint, is a seven-week experience helping people mostly between 40 and 60 design what comes next. The sixth cohort starts next Tuesday, with two spots still open. * He didn’t blow up his life to make his own change. He changed slowly, over eight years, while keeping his job, his house, and his marriage intact. He’s now compiling a year of his newsletter with an eye toward turning it into a book. Key Insight: “It took me, really, eight years of slow change.” Key Quotes “It just made me feel like everybody else.” — Gary Allen “It’s getting in my way now.” — Gary Allen “If you can treat it with curiosity and not judgment, that’s the real game changer.” — Gary Allen “I didn’t actually go, okay, I’m quitting my job and I’m going to sell a house and move to Bali.” — Gary Allen “It took me, really, eight years of slow change.” — Gary Allen Resources Mentioned * Life Design Collective — Gary’s own coaching practice, built around midlife redesign * The Second Act Blueprint — Gary’s seven-week program helping people in their 40s, 50s, and 60s design what comes next (Next Cohort Starting on Tuesday July 21) * Second Act Sunday — Gary’s weekly Substack newsletter, closing in on its first full year * Richard Rohr and Arthur C. Brooks — authors Gary reads on the idea of a second act in midlife Where to Find Gary Email: hello@garyallen.ie Website: https://garyallen.ie/ Thank You A heartfelt thank you to everyone who joined us live for this conversation, and to Gary Allen for his openness and wisdom. Your presence and engagement make these conversations possible. Building Your Own Second Act Gary’s story keeps coming back to one idea: change that lasts doesn’t come from a dramatic overhaul. It comes from removing the thing that’s been quietly draining your energy and clarity, then giving yourself time to rebuild from there. That’s the same work at the center of The Sober Creative Method™, my 90-day, 1:1 coaching experience for people who want to remove alcohol as the barrier to their full creative capacity. No labels, no rock bottom required, just a structured path back to the energy and clarity that’s already yours. If this episode resonated, send me a message and tell me where you’re at. I read every one. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit newsletter.thesobercreative.com/subscribe

  8. Jul 11

    Episode 060 - Chasing Curiosity Instead of Chasing Quiet: Bob Mathers Found There Was No Ceiling Once He Stopped Drinking

    Bob Mathers spent 35 years being “Bobby Good Times.” He was the guy other people kept on speed dial for a good night out, the one always up for an extra day of drinking when everyone else had called it quits. He built a career as a speaker and coach. He raised two sons. From the outside, it looked like a full life. On the inside, he was running on a weekly cycle of shame and recovery that had become so normal, he stopped questioning it. In this conversation, Bob sits down to talk about what it actually took to break that cycle. He walks through the rules he tried and failed to follow, the Monday-morning mood he lived in for years, and the night he finally collapsed into his wife’s arms and said he had to stop. He also talks about a health scare with his son that reframed everything, and about a discovery he made once alcohol was out of the picture: a version of creativity he’d spent his whole life insisting he didn’t have. What makes this one land isn’t just the honesty. It’s the specificity. Bob doesn’t talk about sobriety in abstractions. He talks about counting bottles in a fridge at 17, a mood scale that ran from a two on Monday to a nine on Friday, and writing his first song at 55, in a single day, about a drive with his mother. If you’ve wondered what’s actually on the other side of quitting, this conversation gives you a real answer. Show Notes [02:45] The First Drink and Decades of “Bobby Good Times” * Bob’s first drink was a stolen Labatt Blue from his dad’s fridge at 17. His mom counted 23 missing bottles because he was acting strange. * The taste was awful, but the feeling hooked him. It became, in his words, the answer to being the person he wanted to be. * From 17 to 52, drinking anchored his life. Friday and Saturday nights were automatic, and he was often the one pushing for a Thursday or Sunday too. * He could count on one hand how many weekends he took off in 35 years. Key Insights: “It was actually really gross, but I loved the way it made me feel. It just seemed like the answer to being the person that I wanted to be.” [09:38] When It Stopped Being Fun * Watching his own sons go through hangovers, Bob now recognizes the anxiety he felt in his 20s and 30s but never had words for. Nobody talked about anxiety in the 80s. * The real darkness set in during the five years before he quit, at 52. * Drinking that once made him feel social and connected started making him feel isolated. He was hiding it and lying more. * COVID sped everything up. The backyard parties were fun in the moment, but when life went back to normal, the drinking never slowed back down. Key Insights: “It just felt like this thing that used to make me more social and more fun, and make me feel like a part of a group, was increasingly isolating.” [12:13] The Rules That Never Worked * Bob negotiated with himself constantly: no beers over 5%, no mixing beer and wine, no drinking on Sunday, no drinking before 4pm. * Every rule bought him about two weeks before it collapsed. * He kept waking up next to his wife, unable to remember the night before, promising things would change. * Eventually he realized the rules were never going to hold, because he was powerless the moment he took the first drink. Key Insights: “I had tried everything, and the only thing left was: I’ve got to stop. I’m powerless as soon as I have one drink.” [14:02] Living the Monday-to-Friday Mood Cycle * For two to three years before quitting, Bob’s whole life ran on a weekly mood cycle. * Monday mornings he’d cancel meetings and take long walks alone, timed so his family wouldn’t see him. * By Thursday he’d start to feel human again. By Friday he was ready to go out and do it all over. * Looking back, he realized that cycle wasn’t rest and recovery. It was survival on repeat. Key Insights: “Monday I’m a two. Wednesday I’m still pretty low, I’m a five. But by Thursday I’m a seven, and Friday morning I’m a nine.” [17:19] Two Wake-Up Calls: Quitting and a Health Scare * Bob quit on the Monday after Easter Sunday in 2022, following a messy family dinner the night before. * He came home from a walk, collapsed into his wife’s arms, and said he had to stop. That became day one. * Less than a year into sobriety, a second wake-up call hit: his son collapsed at a restaurant, and doctors found a bacterial mass pressing on his brain. He was rushed into emergency surgery and fully recovered. * Bob credits being a couple years sober for how he and his wife handled it. If he’d still been drinking, he says he doesn’t know what would have happened. Key Insights: “Life just gets really simple, really fast. I just didn’t want to waste a single day.” [21:53] Three Years to “This Is Actually Better” * Bob describes his first year sober as white-knuckling through every first: his birthday, Christmas, New Year’s, a boys’ trip, a wedding. * Year two, he started testing whether he could actually enjoy himself sober instead of just proving he could survive it. * It took a third year before he believed the people who’d told him you could have fun without drinking. * Losing his friends scared him most. His phone did stop ringing for some things, but the friendships that mattered stayed intact. He’s the only one in his friend group who’s sober. Key Insights: “Everyone quits, whether you quit 10 minutes before you take your last breath or 10 years before you die, or 20, or 30. Everyone quits. I’m just the one that went first.” [28:04] Writing His First Song at 55 * Bob spent his whole life telling himself he wasn’t a creative person, even while building a career around surrounding himself with creative people. * Songwriting eluded him for years. He’d write a couple of lines, decide they were garbage, and quit before finishing a verse. * A guest on his own podcast, singer-songwriter Peter Katz, mentioned a songwriting retreat. Bob went: Friday for writing, Saturday for recording, Sunday for listening back to a fully produced song. * The song is about driving his mother to her new retirement home. He played it for his family, and they cried. Key Insights: “Creativity is inside all of us. It’s just buried under self-doubt and imposter syndrome and fear of judgment. And it’s there.” Key Quotes “I had tried everything, and the only thing left was: I’ve got to stop. I’m powerless as soon as I have one drink.” - Bob Mathers “Monday I’m a two. Wednesday I’m still pretty low, I’m a five. But by Thursday I’m a seven, and Friday morning I’m a nine.” - Bob Mathers “I’ve realized that eight was actually a six, because I found a 12 and a 13, and I think I found a 15 and a 16. Who’s to say there is a limit on this?” - Bob Mathers “Everyone quits, whether you quit 10 minutes before you take your last breath or 10 years before you die, or 20, or 30. Everyone quits. I’m just the one that went first.” - Bob Mathers “Creativity is inside all of us. It’s just buried under self-doubt and imposter syndrome and fear of judgment. And it’s there.” - Bob Mathers Resources Mentioned * The Growth Mixtape — Bob’s podcast, with new episodes every other Thursday * The Restless Leader — Bob’s Substack, written for people who built a successful career and now feel restless * Peter Katz — singer-songwriter and speaker from Toronto who hosts songwriting retreats * Rob Zabo — the award-winning producer who produced Bob’s song, and an upcoming guest on The Growth Mixtape Where to Find Bob * LinkedIn: search Bob Mathers * Podcast: The Growth Mixtape, wherever you listen, new episodes every other Thursday Thank You A heartfelt thank you to everyone who joined us live for this conversation, and to Bob Mathers for his honesty and generosity in sharing his story. Your presence and engagement make these conversations possible. Your Next Step Bob spent decades telling himself he wasn’t creative. It took removing alcohol, and a lot of honesty about what he was actually afraid of, to find out that wasn’t true. What he found waiting on the other side wasn’t a smaller life. It was a bigger one, with no ceiling he could find yet. If any part of his story landed for you, that’s worth paying attention to. You don’t need a plan figured out right now. A quick conversation to feel seen and discuss where you are is a great start. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit newsletter.thesobercreative.com/subscribe

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About

In this live Substack series, I explore intimate conversations with people navigating their sobriety journeys. Each episode highlights personal transformations, practical strategies, and the unexpected creative advantages of clear-minded living. These uplifting discussions reveal how sobriety enhances artistic expression, business success, and personal fulfillment. Join us to discover how these individuals are finding greater authenticity, purpose, and creative power through sobriety. newsletter.thesobercreative.com

Information

  • Creator
    with Josh Woll
  • Years Active
    2025 - 2026
  • Episodes
    64
  • Rating
    Explicit
  • Copyright
    © Josh Woll
  • Show Website
    The Sober Creative Podcast

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