How I Learned That

What it is about

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’s own description, taken unchanged from the podcast feed.
Dr. Deena Kara Shaffer

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Apple Podcasts

Latest episodes

How I Learned That Dead Ends Teach You the Shape of the Maze

2026-11-09 · 50 min · Season 1, episode 7

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,…
How I Learned That All of This Is Made Up

2026-11-02 · 37 min · Season 1, episode 6

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…
How I Learned That Schooling and Learning Are Not the Same Thing

2026-10-25 · 1 hr 4 min · Season 1, episode 5

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…
How I Learned That Nobody's Thinking About You That Much

2026-10-18 · 34 min · Season 1, episode 4

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…
How I Learned To See the Whole Before the Parts

2026-10-11 · 33 min · Season 1, episode 3

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…
How I Learned That the No's Are Redirects

2026-10-04 · 43 min · Season 1, episode 2

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…
How I Learned That Life Was Hard

2026-09-27 · 37 min · Season 1, episode 1

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…
Welcome from Dr. Deena

2026-08-26 · 3 min

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…

Episode details from the publisher’s feed. Playback happens at the publisher.

Publisher details

Oldest episode in feed: 08/2026
Typical length: 20 min
Format: Episodic Newest first, episodes stand alone

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