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by Ousman Diallo
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The most dangerous kind of procrastination doesn't look like procrastination. It looks like ambition. You're building, preparing, grinding, sacrificing now for later. But what if the life you're waiting to start is the one you're already living?Franz Kafka spent his days at a workers' accident insurance office in Prague and wrote at night, convinced his real life was happening somewhere else. He asked his friend Max Brod to destroy much of his work after his death. Brod didn't, and the writing Kafka squeezed into the margins became the work that defined him. Fernando Pessoa went further. Through Bernardo Soares, the Lisbon bookkeeper of The Book of Disquiet, he turned postponement into an identity: "I've always lived on the edge of things."In this episode, I look at what Carl Jung called the provisional life:- why ambitious people give waiting respectable names: focus, discipline, sacrifice- how keeping every possible life open becomes a way to avoid choosing one- the Harvard study that found our minds wander 46.9% of the time, and the "end of history illusion"- Kafka's parable Before the Law, and a door built for only one manYou can build an audience while waiting to feel legitimate. You can make art while waiting to feel like an artist. So what part of your life have you decided doesn't count yet?If you're a designer, creator or builder who keeps telling yourself the real thing starts after the next launch, this one's for you.
What if some of the greatest work of the 20th century was made for no one?For about forty years, Vivian Maier worked as a nanny, most of that time in Chicago. On her days off she walked the streets with a Rolleiflex around her neck and photographed strangers, children,shop windows and her own shadow. She took more than 100,000 photographs and showed almost none of them to anyone. Thousands of rolls were never even developed. In 2007, a box of her negatives sold at a Chicago storage auction. Two years later she died, unknown, just before the world started calling her one of the great street photographers.In this episode, I look at what Maier's life says about why we make things:- the difference between making work and building an audience- what it means to have an eye with no one watching- why the habit of seeing might matter more than being seenIt's an uncomfortable question for anyone creating in public today. If no one had seen it, would it still have been great?If you're a designer, creator, builder or creative who has ever wondered whether your work counts without likes, followers or a byline, this one's for you.
Listeners Preferred the AI Song… Rithik Kundu on What a Blind Test Reveals About Taste, Originality & the Future of MusicWhat happens when listeners don't know which song was made by a human and which was made by AI?Rithik Kundu is a Brooklyn-based music-tech researcher, producer, and investor working where generative audio, AI, and music rights meet. He founded NYU Generative Audio & AI, is a managing partner at Joker Deck Ventures, and contributes to the World Intellectual Property Organization's technical network on AI and copyright. His blind listening study — human-made tracks from Grammy-winning producer Mr. Sonic set against AI-generated parallels made in Suno — has been presented at Sony.In this conversation, Rithik and I dig into what that study found: across 95 listeners and four genres, the human-made music won in reggaeton and cumbia norteña, while the AI tracks were often preferred in the more Western-leaning genres, even as listeners described them as familiar and generic. We talk about why familiarity drives taste in a world of more than 100,000 new uploads a day, why training data is the "fruit in the blender" behind every AI song, and what happens to genres that barely exist in that data.We also get into the fear of the "death of the process," why the major labels may want their own AI more than they want to stop it, and what fair compensation could look like, from attribution technology to royalties for the artists whose work trains the models. Then we zoom out: open-sourcing training data, the Napster parallel, synthetic data, spoken-word poetry, and what young creators lose if they skip the fundamentals and go straight to the prompt.If you're a musician, designer, or builder trying to figure out where human craft still matters in the age of generative AI, this one's for you.
Up until about ten years ago, reaching a hundred million people would have cost you millions upon millions of dollars. Today it's free — it fits in your pocket. So why do most creators still stay invisible?Jake Isham is a Los Angeles–area filmmaker-turned-brand strategist and the Founder & CEO of Creative Minds. With over 1 billion views generated and more than 150 brands served, his work spans names like Callaway Golf, Grant Cardone, 5.11 Tactical, TravisMathew, Marshall Faulk, and Chloe Fineman. Instead of chasing vanity metrics, Jake uses cinematic storytelling structure to turn lived experience into lasting credibility and influence.In this conversation, Jake and I dig into what it means that anyone can now reach an audience once reserved for the biggest ad budgets — and why the difference between building a business and becoming an entertainer changes everything about how you should use it. We talk about why the biggest companies still have a face, how Matthew McConaughey walked away from a $10 million rom-com to rebuild his personal brand, and what Jake has learned from watching famous clients once the cameras stop rolling: the ultra-successful love hard work the way athletes love the game.We also get into the long road to craft — his father's advice to "keep a camera in your hand," why Christopher Nolan and Michael Bay were directing corporate videos and commercials before their first features, and why an artist selling their work is running a business whether they like it or not. Then comes the uncomfortable math: unless you're a one-in-a-million outlier, you have to out-create the market. Three posts a day, on five platforms, for a year — five thousand posts. Be willing to suck. Grit, not genius, is the determining factor.If you're a creator, artist, or founder who's been waiting for permission — or for the algorithm to find you — this one's for you.
For most of software’s history, designers could assume that an input would produce a predictable output. AI is changing that.In this episode, Ousman speaks with Tammy Coombs, a product designer and design engineer with more than 15 years of experience building complex tools for security, reliability, and operations teams. Her work has included leading UX initiatives at Palo Alto Networks and designing AI systems for security researchers, Site Reliability Engineers, and other expert users working in high-stakes environments.Tammy explains how product design must evolve as software moves from deterministic workflows toward probabilistic systems that interpret human intent—and sometimes get it wrong.They discuss the growing overlap between design and engineering, the role of Figma in an AI-assisted workflow, designing guardrails around natural-language interfaces, and why AI should support human judgment rather than quietly replace it.The conversation also explores what remains unchanged: understanding users, learning the language of a complex domain, experiencing failure firsthand, and knowing when technology should simply get out of the way.
AI Can Generate. Can You Judge? Boris Eldagsen & the New Rules of Knowledge WorkIn 2023, Boris Eldagsen won the Creative Open category of the Sony World Photography Awards with an AI-generated image—and then refused the prize.The experiment exposed a larger problem: technology was moving faster than the institutions responsible for evaluating, regulating, and governing it.Boris Eldagsen is a Berlin-based artist, philosopher, educator, consultant, and early practitioner of generative AI. He works directly with emerging models, tests new systems, teaches AI workflows, and advises organizations navigating the shift from traditional production to human–AI collaboration.In this episode, we move beyond the question of whether AI-generated images qualify as photography.Instead, we examine what happens when producing an answer, image, strategy, or piece of work becomes nearly effortless.What becomes more valuable when output becomes abundant?Boris argues that AI is a knowledge amplifier. It rewards people who understand their domain, can provide useful context, recognize weak output, and make deliberate decisions about what happens next.
Why Building Anything Beats Waiting for Permission — The Optionality Argument Nobody Makes (Part 2)Last episode we did the hard half — the broken promise, the 41.5% underemployment, the grief a generation isn't allowed to name. This is the other half. Because while institutions take their time catching up, you still have to wake up tomorrow and decide what to do with the day in front of you.So we change the question: forget what society owes you for a moment — what does the practice of building actually offer you, sitting where you sit, with the life you actually have? The answer is not what most people tell you, and once you see it framed correctly, you can't unsee it.We start with Jevons Paradox — a 160-year-old principle that explains why making coal more efficient made Britain burn more of it, and why the printing press, the automobile, and the internet each created entire worlds nobody could have predicted. Then we get honest about the uncertainty, because the historical pattern is encouraging, not guaranteed.And then the spine of the episode: the real case for building. Most people frame it as a bet on success — build the thing, hope it grows. That framing is wrong, and it's why building feels demoralizing. The actual case is this: building is not a bet on outcomes. It's the construction of optionality. You're not building because the thing will save you. You're building because every node you put into the world becomes a door — and in a world where the doors you were promised are closing, the person with the most doors wins. We take the survivorship-bias objection head on, and show why it actually strengthens the argument.We close with two honest tracks — one for the listener with stability, one for the listener in survival mode — because they are not having the same conversation, and pretending they are is why this kind of advice usually rings hollow.Both truths, held at once: the structural critique is real, and it doesn't get to stop you from building. The roads you were promised are closing. The doors you make are the doors you keep.
The Career Ladder Was Invented in 1911 — And It's Being Dismantled While You're Still Climbing It41.5% of recent U.S. college graduates are underemployed. In China, 97,000 new PhDs are competing for jobs that don't exist — some applying to be rural clerks or hotel kitchen interns. These are the people who did everything right. So what do we actually owe them?This is Part 1 of a two-part conversation almost nobody is having honestly. Most takes on the death of the career ladder collapse two separate questions into one — the systemic question (what did society break, and what does it owe the people who held up their end?) and the individual question (what do you do, sitting where you sit, with the life you have?). Conflating them is how we end up telling debt-drowned graduates to "just start a podcast."So today we do the systemic conversation properly — no rushing to the inspiring part. We trace the corporate ladder back to Frederick Taylor's 1911 Principles of Scientific Management and show how an entire civilization built itself around one management invention. We look at what's happening to real graduates in real time. We name the grief — and the Northwestern research on narrative identity that proves it's a real psychological injury, not weakness. And we ask the question missing from public discourse: what would an honest societal response actually look like?This episode won't tell you creative thinkers will inherit the earth. It also won't tell you the system failed and nothing can be done. Both are too easy. The truth is harder — and more useful.
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