The Unmistakable Creative Podcast

Donny Jackson, poet and psychologist, reflects on growing up as a working-class black kid in Pittsburgh where his father was a postal worker for 35 years and his mother was a nurse's aide—parents who instilled work ethic, integrity, and honor while navigating a world not built for young black children. Jackson traces the roots of American racism to the legacy of slavery where black people started as chattel on unequal footing and never shed that history, creating an internalized stain on both sides of the racial fence. He explains how separate but equal was never true, how tribalism prevents empathy development because it is much harder to oppress someone whose feelings you have taken into account, and why redlining and subtle discrimination in apartment rentals remain part of the disease of living a racialized life. Drawing from Isabel Wilkerson's research, Jackson highlights how FDR-era policies designed to improve American life excluded black people, creating structural racism that takes a toll. He warns that 70 million Trump voters represent at least 70 million reasons to remain fearful even after Biden's election.

Bjorn Ryan-Gorman, professional snowskater and LGBTQ+ advocate, shares his journey from hiding his sexuality behind aggressive board sports to building a life of authenticity in Portland. Growing up in Montana as a sponsored snow athlete, Ryan-Gorman used snowboarding and skateboarding as outlets for self-hatred and denial, pushing himself to dangerous extremes before hearing a podcast that changed everything. He reveals the complex reactions from family—his mom's unexpected resistance, his dad's surprising embrace, and grandparents who rejected him entirely. Ryan-Gorman explores masculine drag within the bear community, the importance of diverse LGBTQ+ representation beyond stereotypes, and the persistent question that haunts him in rural spaces: Am I safe here? This conversation challenges assumptions about what gay men look like, explores how coming out should be celebrated but not sensationalized, and offers insight into the ongoing struggle of navigating safety, identity, and belonging in America.

David Sax, author of The Future Is Analog and The Revenge of Analog, shares how his first job photocopying newsletters in a windowless room reeking of toner during the summer of Living La Vida Loca revealed something profound about office culture: even the worst environments create friendships, energy, and human relationships that working from home cannot replicate. Drawing from a Microsoft study of 60,000 employees during the pandemic, Sax explains how remote work maintained task completion but siloed communication, preventing the embodied cognition that happens when you bump into colleagues and see project models on desks—passive knowledge transfer impossible to replicate through PDFs and PowerPoints. He argues that Y Combinator consistently found remote teams had higher failure rates because creativity and innovation, the currency of the modern economy, require human connection in shared physical spaces. Sax challenges the wrong conversation about how many days to go into the office, arguing the right conversation is redefining productivity beyond the 19th-century model that equates time with money.

David Epstein, author of Range: Why Generalists Triumph in a Specialized World, dismantles the myth that early specialization is the only path to excellence. Drawing from research on elite athletes, musicians, and scientists, David reveals how individual variability in learning means there is no one-size-fits-all approach to skill development. He reframes the Tiger Woods and Mozart narratives, showing how their success came from internal drive, not just parental pressure. From his own journey—leaving Sports Illustrated to investigate drug cartels—David demonstrates why sampling periods, lateral thinking, and diverse experiences create more adaptable, innovative problem-solvers than narrow expertise alone.

Ayelet Fishbach, motivation researcher at University of Chicago, dismantles the fantasy-driven approach to New Year's resolutions and goal-setting. Drawing from data spanning multiple years, she reveals that while temporal landmarks like New Year work for initiating goals, only 20% of people still pursue them by November—the difference comes down to whether you're fantasizing or planning. Fishbach explains how fantasies (envisioning yourself already achieving the goal) actually decrease motivation to send job applications or take action, whereas concrete plans ("I will call my connections, work on my resume, here are the steps") drive execution. She introduces the critical balance between "why" questions (abstract purpose that prevents you from giving up) and "how" questions (concrete steps that enable execution), warning that goals become too abstract when they reach "I want to be happy" and too concrete when you lose sight of why you're doing them. The conversation explores Michael Phelps' visualization strategy (preparing for goggles filling with water, not just winning gold) and why optimism without planning is just delusional fantasy masquerading as motivation.

Daniel Stillman, author of Good Talk: How to Design Conversations That Matter, reveals how conversations are designed—whether we realize it or not. Drawing from his background in design thinking and facilitation, Daniel breaks down the components of conversational architecture: openings, turns, power dynamics, and interfaces. He explains why physical and digital spaces fundamentally alter what conversations are possible, how to slow down heated exchanges through pacing and tone, and why the most important conversations we design might be the ones we have with ourselves. From boardrooms to Zoom rooms, Daniel shows how small changes to conversational structure can unlock radically different outcomes.

Dandapani, former Hindu monk who lived monastically for 10 years, shares teachings from his guru on treating the mind as an operating system that must be understood before it can be mastered. He explains the critical distinction between a focused life (giving undivided attention to whoever/whatever you're engaged with) and a purpose-focused life (where your life's purpose defines priorities that drive what you focus on). Drawing from Napoleon Hill and his guru's book *Merging with Siva*, Dandapani unpacks sexual energy transmutation—asking: if one sperm created a person who could change the world, what could a million create if that energy were harnessed instead of wasted? He reveals monastic teachings rarely shared: how to sleep, wake, eat, breathe, sit, and shower to put energy back into your body. Dandapani argues that without understanding how your mind works, you can't focus long enough on yourself to achieve self-reflection and discover what you truly want—making intentionality impossible before mastering the fundamental operating system we all carry but were never taught to use.

Fred Dust, former global managing partner at IDEO and author of *Making Conversation*, shares a vulnerable and deeply insightful look into the role conversation plays in healing, connection, and societal progress. Drawing from personal experience — coming out, losing his brother, working with the Obama administration, and navigating complex emotional terrain — Dust lays out the foundations for transformative dialogue. Through themes like courage, creative listening, boundaries, and space design, he explores how to structure environments (physical and emotional) that encourage openness and empathy. Whether discussing Zoom conversations, conflict triggers, or everyday bravery, Dust presents a powerful case for approaching even the hardest topics with intentional design, presence, and care. This conversation is a masterclass in humanizing our interactions — and learning to talk in ways that move us, rather than divide us.

Cal Newport unpacks his framework for Slow Productivity, built on three core principles: doing fewer things, working at a natural pace, and obsessing over quality. He introduces "pseudo productivity"—the toxic heuristic that emerged in mid-20th century knowledge work when visible activity became a proxy for useful effort because traditional productivity metrics (Model Ts per hour, bushels per acre) no longer applied. Newport argues that pseudo productivity was tolerable until the digital office revolution—email, Slack, mobile computing—enabled visible activity to be demonstrated at incredibly high frequency, anywhere, anytime, creating a performance theater that drains actual productive capacity. The conversation explores how to build custom AI systems for daily planning (using GPT models trained on transcripts and book notes), the three levels of working with large language models (training from scratch, fine-tuning, and software intermediaries), and why specialized vertical AI will dominate the next wave of innovation. Newport makes the case for abandoning industrial-era proxies and reclaiming knowledge work as a craft that requires depth, patience, and quality over constant performative busyness.