- 8
- Episodes
- Weekly
- Cadence
- 2026
- First episode
About How I Learned That
How I Learned That is a podcast about the kind of learning nobody put on your report card, but that ended up mattering most. Each episode, learning strategist Dr. Deena Kara Shaffer sits down with someone who’s created success in their lives and asks the question we rarely think to ask: how did you actually learn to become yourself? It's an honest, human show for parents who are worried about their kids and for the teenagers who feel that worry too. Made for the car ride home from sports practice or tutoring, and useful for a lifetime.
- Publisher
- Dr. Deena Kara Shaffer
- Category
- education
- Language
- en
- Explicit
- No
- First episode
- 26 Aug 2026
- Latest episode
- 9 Nov 2026
Latest episodes
8 episodes in the feed.
9 Nov 2026
How I Learned That Dead Ends Teach You the Shape of the Maze
Alan Smith is the co-founder of Strategyzer and co-creator of the Value Proposition Canvas, frameworks that have reorganized how millions of people think about building things in the world. But long before any of that, he was the kid in grade one breaking pencil tips on purpose so he could get up and sharpen them, and the kid in the schoolyard driving a cardboard race car with an old steering wheel, cheerfully unconcerned that nobody else got it. In this conversation, Alan traces a school journey made of three distinct loves, the auto shop, the computer lab, the art class, and a guidance counsellor who was the first to put words to what those three things had in common. He talks about the mentor who could smell his portfolio's concept before Alan could explain it, the coach who helped him find the thing underneath the thing, and the hardest lesson he has ever had to learn: one that had nothing to do with business models and everything to do with what you see when you look in the mirror. An episode for anyone who loves making things, and suspects the making might be the point. Guest Bio Alan Smith is a design-trained entrepreneur, visual thinker, and the co-founder of Strategyzer. Integrating design principles into business strategy, he co-created the globally recognized Value Proposition Canvas. He also visually structured and co-authored the international bestseller Business Model Generation, alongside Alex Osterwalder and Yves Pigneur. This framework revolutionized corporate innovation and is used by millions worldwide. Alan now applies his venture development expertise as the VP of Venture Development at FutureSight, helping early-stage entrepreneurs build successful software startups. https://www.linkedin.com/in/thinksmith/ (https://www.linkedin.com/in/thinksmith/) Resources + Referenced Links Alan Smith: LinkedIn and YouTube as @ThinkSmith Alan Smith (@thinksmith) • Instagram photos and videos (https://www.instagram.com/thinksmith/) Business Model Generation (book, Strategyzer (https://www.strategyzer.com/) series) Value Proposition Design (book, Strategyzer (https://www.strategyzer.com/) series) The Invincible Company (book, Strategyzer (https://www.strategyzer.com/) series) Testing Business Ideas (book, Strategyzer (https://www.strategyzer.com/) series) High Impact Tools for Teams (book, Strategyzer (https://www.strategyzer.com/) series) Business Model You (book, co-authored with Tim Clark) FutureSight (Alan's current venture, early-stage startup development) The Creative Act by Rick Rubin (referenced) Gratitudes Thank you, Alan, for making time from a cottage in Tiny, Ontario, for this conversation. For the stop sign and the cardboard race car and the dead ends and the mirror. And for getting just a little emotional about the book you wished you could read, and then writing it anyway. Interested in being on the podcast? Know of someone who might be a good fit? Email podcast@awakenedlearning.ca (mailto:podcast@awakenedlearning.ca) and let us know! For more on Learning Strategies: Awakened Learning, The Learning Strategy Studio (http://www.awakenedlearning.ca/about-lss) For a Talk / Learning Strategy Training: DKS (http://www.deenakarashaffer.com) For our multi-solving anti-procrastination app: paced.school (http://paced.school) Keep in touch: Newsletter (https://www.awakenedlearning.ca/newsletter)
2 Nov 2026
How I Learned That All of This Is Made Up
Rachel Molenda, known on dance floors as DJ Rae, has spent years helping people come home to themselves. First as a holistic nutritionist, then as a mindset coach, and now as a DJ and the creator of Reunion: an alcohol-free, all-the-way-awake, love-filled dance party movement for women that leaves participants remembering who they really are. At the centre of her work, and of this conversation, is a single idea: self-trust. What it is, how we lose it, and, with attention and a little courage, how we get it back. It turns out the answer is simpler than almost anything we've been sold. Guest Bio Rachel Molenda (@rachelmmolenda), also known as DJ RAE, is a Mindset Coach turned DJ and the creator of REUNION (@thereuniondanceparty) – a fast-growing, alcohol-free party movement and event series for women. Known for her groovy, melodic house sound layered with hints of disco and funk and wickedly contagious energy, DJ RAE creates sets that are both euphoric and leave you remembering who you are. DJ RAE has quickly made her mark, performing at notable events including Daybreaker, Othership, Sonic Springs Festival, ROM After Dark, Chocolate Groove, Floorplay and Secret Society, as well as a range of brand events, conferences, and festivals. Resources + Referenced Links @RachelMMolenda on Instagram rachelmolenda.com (http://rachelmolenda.com/) Reunion Dance Party: thereunionDanceParty.com | @thereunionDanceParty Daybreaker, Othership, Sonic Springs Festival, ROM After Dark (venues and events referenced) Any upcoming REUNION events or to follow Rachel Molenda + REUNION @rachelmmolenda & @thereuniondanceparty on IG Gratitudes Rachel, you brought radiant, honest, unoptimized, and alive energy to this show. Thank you for your stories, your openness, and your reminder that we come into this world with our magic intact. Some of us just needed to hear it. We're so glad you were here to say it. Interested in being on the podcast? Know of someone who might be a good fit? Email podcast@awakenedlearning.ca (mailto:podcast@awakenedlearning.ca) and let us know! For more on Learning Strategies: Awakened Learning, The Learning Strategy Studio (http://www.awakenedlearning.ca/about-lss) For a Talk / Learning Strategy Training: DKS (http://www.deenakarashaffer.com) For our multi-solving anti-procrastination app: paced.school (http://paced.school) Keep in touch: Newsletter (https://www.awakenedlearning.ca/newsletter)
25 Oct 2026
How I Learned That Schooling and Learning Are Not the Same Thing
Dwayne Matthews grew up on a small island in Trinidad, navigating a school system where an 11-year-old's exam results were published in the newspaper, corporal punishment was a daily reality, and you traveled to school alone through streets that required alertness just to survive. By the time he arrived in Canada at 16, he had already learned something most of his schoolmates hadn't: that schooling and learning are not the same thing. In this conversation, he takes us through a winding path from social work to sociology to a chance romantic encounter that led him to Teachers College, and then two years in Peru that changed everything. He shares the Trinidadian concept of liming, a kind of sanctioned, purposeful doing-nothing, and the practice his family has built around it. And he asks what may become the most important educational question of this generation: in a world where information is everywhere and abundant, what is actually scarce? His answer is as practical as it is radical. Guest Bio Dwayne Matthews is a Future Strategist and Innovation Evangelist helping audiences bridge technology and human potential in the AI era. With 20 years spanning education, AI, neuroscience, and human performance, he created the HumanOS framework for leading confidently amid disruption. He has advised Fortune 500 leaders (Barrick Gold, Suncor, P&G, DuPont), addressed the United Nations, and served as an XPRIZE Advisor. As President of NeuroEdX, he trained elite performers including Air Force pilots and Navy SEALs using neurotechnology. Author of three books, including HumanOS: The Critical Update, Matthews is a regular on CTV's Your Morning, helping people stay clear, focused, and human in the age of AI. Resources + Referenced Links Dwayne Matthews (https://dwaynematthews.life); LinkedIn (@DwayneMatthewsOCT), Substack (Dwayne Matthews), website (dwaynematthews.life) Dwayne Matthews (@tomorrownow.io_) • Instagram photos and videos (https://www.instagram.com/tomorrownow.io_/) Human OS: The Critical Update (https://dwaynematthews.life/) (book by Dwayne Matthews) Human OS cohort programme (four in-person sessions over one year; details coming soon at his website and Substack) Dwayne Matthews O.C.T - The Keynote Speaker after the AI speaker | Author of HumanOS: The Critical Update | CEO TomorrowNow.io | LinkedIn (https://www.linkedin.com/in/dwayne-matthews-o-c-t-b134447/) The Tao of Pooh by Benjamin Hoff (referenced) Irreducible by Federico Fagin, inventor of the microprocessor (referenced; Fagin's book on consciousness theory) Sir Roger Penrose, Nobel laureate physicist (referenced on consciousness) Dr. Jocelyn Faubert, University of Montreal, creator of the 3D MOT (three-dimensional motion object tracking) paradigm for measuring and training selective and sustained attention Khan Academy (referenced as a tool for finding and filling knowledge gaps) Gratitudes Thank you, Dwayne, for your generosity with your story, your time, and your thinking. You introduced us to liming, and we haven't quite been the same about Saturday afternoons since. We're so glad you said yes. Interested in being on the podcast? Know of someone who might be a good fit? Email podcast@awakenedlearning.ca (mailto:podcast@awakenedlearning.ca) and let us know! (www.awakenedlearning.ca/about-lss) (www.deenakarashaffer.com) (paced.school) (https://www.awakenedlearning.ca/newsletter)
18 Oct 2026
How I Learned That Nobody's Thinking About You That Much
Takara Small has spent her career in the business of telling other people's stories. As a technology journalist — at Fortune, CTV, CBC, Metro Morning, the BBC, and beyond — she asks the questions. Today, she's the one being asked. What she shares is honest, warm, and quietly powerful: a conversation about growing up between cities and classrooms, navigating spaces that weren't built with her in mind, and the understanding — hard-won — that the room doesn't get to decide if you belong. You do. Guest Bio Takara Small is a Toronto-based technology journalist, entrepreneur and developer. She’s also the technology columnist for Metro Morning (Toronto’s top-rated morning radio show), host and producer of the Globe and Mail startup podcast ‘I’ll Go First’ as well as on-air tech expert for CBC and CTV. Her journalism work has been featured in news outlets around the world. Meanwhile as a sought-after and renowned public speaker, she’s often invited to share her insights about entrepreneurship and innovation with international audiences at festivals, like Deloitte’s DisruptionByDesign summit, Collision conference, Elevate, CIX and Social Media Week. As the founder of VentureKids Canada (a Toronto-based nonprofit) she and her team provide free coding classes, programming workshops, food and computer supplies to students living in the city’s underserved communities. The organization works in partnership with Toronto Community Housing Corporation (Canada’s largest public housing agency and second biggest in North America), Toronto Public Library (Canada’s largest public library system) and more to boost diversity in the city’s growing technology sector. Resources + Referenced Links @TakaraSmall on all platforms Secret Canadians (https://open.spotify.com/show/0CaSTE0s2fvSImHfYq07EJ) Metro Morning, CBC Radio Globe and Mail Startup Podcast: All Go First For more info on Learning Strategies: Awakened Learning (https://www.awakenedlearning.ca/) For a talk on Learning Strategies: DKS (https://deenakarashaffer.com/) For our multisolving anti-procrastination app: paced (https://paced.school/) The Learning Strategy Studio (https://www.awakenedlearning.ca/about-lss) Newsletter (https://www.awakenedlearning.ca/newsletter) & Blog (https://www.awakenedlearning.ca/blog) Interested in being on the podcast? Know of someone who might be a good fit? Email podcast@awakenedlearning.ca (mailto:podcast@awakenedlearning.ca) and let us know!
11 Oct 2026
How I Learned To See the Whole Before the Parts
Dr. Tanya Harrison has spent her career working on Mars rovers, and she'll be the first to tell you that what got her there had less to do with being brilliant at school than with being relentlessly curious and willing to figure things out sideways. In this conversation, she takes us back to being the kid in three band classes a day who hand-wrote Star Trek sheet music because nobody told her she shouldn't. She talks about navigating a physical disability, learning to self-promote as a scientist (a skill she had to watch others struggle without, too), and the learning strategy that has served her throughout: always see the whole before you try to understand the parts. She makes a quietly radical argument for centering curiosity and the lineage of human knowledge at the heart of education, rather than facts and scores. And in her closing answer, she turns the conversation toward something she is genuinely still figuring out: how to be a person in the world beyond the identity of a planetary scientist. A generous, wry, and clear-eyed conversation. Guest Bio Dr. Tanya Harrison is a planetary scientist, future-focused science strategist, and one of the world’s go-to voices on space exploration. She is currently a Fellow of the Outer Space Institute and the Director of Earth and Space Science at Mission Control in Ottawa, Canada. She is also the author of "For All Humankind" and "Mia and the Martians". Resources + Referenced Links Dr. Tanya Harrison: "Tanya of Mars" on Instagram and YouTube, Substack as Tanya Harrison @tanyaofmars / Tanya Harrison Substack www.tanyaharrison.com (https://www.tanyaharrison.com/) For All Humankind (book by Dr. Tanya Harrison) forallhumankind.space Mia and the Martians (book by Dr. Tanya Harrison) miaexplores.com (http://miaexplores.com) Mission Control, Ottawa Outer Space Institute (Tanya is a fellow) NASA Mars Millennium Project, 1999 (the project that launched her Mars obsession) Mariner missions, 1960s–70s (the original Mars discovery papers Tanya's first boss gave her to read) Invitations For more on Learning Strategies: Awakened Learning, The Learning Strategy Studio (http://www.awakenedlearning.ca/about-lss) For a Talk / Learning Strategy Training: DKS (http://www.deenakarashaffer.com) For our multi-solving anti-procrastination app: paced.school (http://paced.school) Keep in touch: Newsletter (https://www.awakenedlearning.ca/newsletter) Interested in being on the podcast? Know of someone who might be a good fit? Email podcast@awakenedlearning.ca (mailto:podcast@awakenedlearning.ca) and let us know!
4 Oct 2026
How I Learned That the No's Are Redirects
Esie Mensah is one of the most sought-after choreographers and directors in Canada, with work spanning Soulpepper, Crow's Theatre, the Stratford Festival, and stages far beyond our borders. But her path to that work was full of closed doors, redirects, and moments where the conventional script said stop. In this conversation, she takes us back to growing up in Hamilton, dancing her way through school without anyone calling it a career, and eventually leaving McMaster University to pursue what she knew in her body long before she could say it out loud. What she discovered along the way was a kind of learning that reaches far beyond any classroom: a connection to her Ghanaian and Ewe ancestors that taught her who she was, and a quiet understanding that the no's were never the end of the story. This is an episode for anyone who has ever felt like they were going in circles, and wondered whether the circle itself might be the point. Guest Bio Esie Mensah is a luminous, visionary, award-winning choreographer, director, and creative leader whose work sits at the meeting place of dance, theatre, and cultural storytelling. A Dora-nominated artist and TEDx speaker, she has choreographed and directed for major Canadian theatres including Soulpepper, Crow's Theatre, and the Stratford Festival, and has collaborated with icons like Rihanna and Drake, as well as the Toronto Raptors. Esie's portfolio spans large-scale productions and international touring across Ghana, Nigeria, France, Italy, the UK, the US, and beyond. Her original production ZAYO premiered in Toronto before touring to Milan, and her latest work continues to center African diasporic storytelling on global stages. Resources + Referenced Links Esie Mensah, choreographer and director: @esiemensah // www.esiemensah.com (http://www.esiemensah.com) ZAIO (https://www.esiemensah.com/projects-work/zayo-2024-esiemensah-creations), Esie's original production, which premiered in Toronto and toured internationally including Milan Fall for Dance North festival, Toronto George Brown College, Commercial Dance Studies programme Canada's National Ballet School Soulpepper Theatre, Crow's Theatre, Stratford Festival T.D. Jakes and Steven Furtick interview referenced (the story of the granddaughter who wanted to hold the light) Contact — Esie Mensah (https://www.esiemensah.com/get-in-contact-with-esie) Afrofuturism: Reimagining a Career in Dance with Esie Mensah | ONsite (https://www.youtube.com/watch?v=sZaSCv10NZg&t=446s) LEGACY REEL ESIE MENSAH (https://www.youtube.com/watch?v=cyiNsEM6p-E&t=15s) My skin was "too dark" for my profession, so I changed the story | Esie Mensah | TEDxToronto (https://www.youtube.com/watch?v=dgGQv4efnI8&t=5s) Back to the future: artists driven by stories of the past | Exhibitionists S04E23 full episode (https://www.youtube.com/watch?v=Hx4sLTOiKCI&t=965s) Invitations For more on Learning Strategies: Awakened Learning, The Learning Strategy Studio (http://www.awakenedlearning.ca/about-lss) For a Talk / Learning Strategy Training: DKS (http://www.deenakarashaffer.com) For our multi-solving anti-procrastination app: paced.school (http://paced.school) Keep in touch: Newsletter (https://www.awakenedlearning.ca/newsletter) Interested in being on the podcast? Know of someone who might be a good fit? Email podcast@awakenedlearning.ca (mailto:podcast@awakenedlearning.ca) and let us know!
27 Sept 2026
How I Learned That Life Was Hard
Jeff Warren is one of the most accessible meditation teachers working today, and he is very much the person you'd least expect. ADHD diagnosed in adulthood, broken neck at 20, years of flailing through what he thought creative work was supposed to look like before discovering that his exact style of mind was never the problem — it was the gift. In this conversation, Jeff takes us through a school journey that moved from French Immersion confusion to literary revelation to social recalibration, and eventually to something much harder: learning, after a serious injury changed everything, how to learn all over again. He talks about what it means to stop performing being a human, why nobody ever told him that life was actually hard, and what a school built around knowing yourself might do to every other subject in the curriculum. A warm, funny, philosophical, and deeply honest conversation with someone who has spent decades making space for other people to slow down. Guest Bio Jeff Warren is a meditation teacher and writer, known for his fun and accessible style of teaching. He is the co-author of The New York Times best-selling Meditation for Fidgety Skeptics and co-host of the Mind Bod Adventure Pod. Jeff’s Do Nothing Project streams for free every Sunday night; his guided meditations reach millions through the Happier and Calm apps, as well as through his Substack, Home Base. Resources + Referenced Links Jeff Warren: Substack, "Homebase with Jeff (https://www.homebasewithjeff.com/)" (free weekly meditation, community) Calm app: Jeff's 30-day "How to Meditate (https://www.calm.com/app/program/mVcvqWcR8C)" programme (10 minutes a day, listened to millions of times) Do Nothing Project (https://jeffwarren.org/the-do-nothing-project): free Sunday night meditation broadcast (access through Jeff's Substack or social links) Consciousness Explorers Club (https://cecmeditate.com/) (Jeff's Toronto-based meditation community) MindBod Adventure Pod (https://www.mindbodpod.com/) (Jeff's co-hosted podcast) Meditation for Fidgety Skeptics (https://jeffwarren.org/books/meditation-fidgety-skeptics/) (book co-authored with Dan Harris, New York Times bestseller) Lord of the Flies by William Golding (referenced as a formative school read) The Chrysalids by John Wyndham (referenced as a formative school read; note: the title Jeff recalled as "The Chrysalis" is actually The Chrysalids) Jeff Warren (http://jeffwarren.org/) Jeff Warren | Meditation Teacher (@_jeffwarren_) • Instagram photos and videos (https://www.instagram.com/_jeffwarren_/) https://www.facebook.com/jeffwarren.org (https://www.facebook.com/jeffwarren.org) Meditation Events | Jeff Warren (https://jeffwarren.org/events) Meditation Party at Omega, Rhinebeck, NY, October 16-18, 2026. Details here: https://jeffwarren.org/meditation-party-new-york (https://jeffwarren.org/meditation-party-new-york) Being Human Takes Practice at Art of Living, North Carolina, October 23-25, 2026. Details here: https://jeffwarren.org/being-human-takes-practice-north-carolina (https://jeffwarren.org/being-human-takes-practice-north-carolina) Interested in being on the podcast? Know of someone who might be a good fit? Email podcast@awakenedlearning.ca (mailto:podcast@awakenedlearning.ca) and let us know! For more on Learning Strategies: Awakened Learning, The Learning Strategy Studio (http://www.awakenedlearning.ca/about-lss) For a Talk / Learning Strategy Training: DKS (http://www.deenakarashaffer.com) For our multi-solving anti-procrastination app: paced.school (http://paced.school) Keep in touch: Newsletter (https://www.awakenedlearning.ca/newsletter)
26 Aug 2026
Welcome from Dr. Deena
We are very good, as a culture, at celebrating where people end up. We are much less honest about how they actually got there. “How I Learned That” is a podcast for parents who lie awake wondering if their child is going to be okay, and for the teenagers who can already feel that they don't quite fit the mold school was built for. It is a show that believes both of them deserve better than the stories we usually tell about learning and success. Host Dr. Deena Kara Shaffer is one of Canada's leading learning strategists. Her work lives underneath the subjects, courses, and years, in the how of learning. In each episode, she sits down with someone who has done something remarkable and asks the questions that rarely get asked: what was your relationship with school? What is the hardest thing you have ever had to learn, and how did you learn it? Was there a moment when you finally understood how you learn, and what did it change? Every guest brings a different answer, and every answer holds an offering of truth: you are far more capable of learning than any institution ever told you. “How I Learned That” is not a show about exceptional people who made it despite the odds. It is a show about ordinary, extraordinary human beings who figured out how to learn, and what happened when they did. Short episodes, generous conversations, real people, and the real stories underneath their lives.
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