How'd You Learn To

How'd You Learn To

By Kerry O'Brien and Lauren RahamEducationSelf-Improvement
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How'd You Learn To episodes

  • How'd You Learn to Date Online? with Nova Nicole

    Online dating isn't just about finding a match; it's about figuring out how to find one. What signals matter? What stories are people telling in their profiles (intentionally or not)? And how do you stay grounded in what you actually want?

    In this episode, Nova shares what she’s learned about asking better questions, spotting red flags early, and practicing self-awareness every step of the way. It’s a conversation about dating—but really, it’s about learning to pay attention to what matters.

    35 min
  • How'd You Learn to Perform Drag?

    What if becoming your most confident self means bombing—repeatedly—in front of a live audience? Jesse Harink’s drag journey began with passion, questionable makeup, and a lot of lessons learned the hard way. But through failure, community, and pure creative drive, Jesse discovered not just how to command a stage, but how to bring that same power into his everyday life.

    In this episode, Jesse shares how learning to perform drag helped him master audience connection, navigate shame, and build confidence that now powers his work in the corporate world.

    36 min
  • How'd You Learn to Build a Film Festival? with Kasia Smuga

    How do you start a film festival in the middle of a pandemic—with no roadmap, no guarantee of success, and no idea if anyone will show up? Kasia Smuga did just that. As programmer of the Mighty Niagara Film Festival, she’s learned everything from grassroots marketing to website logistics to handling corrupted film files—and found joy in every challenge.

    In this episode, Kasia shares how trusting her instincts, leaning into community, and embracing “learning by doing” helped her turn a one-time outdoor experiment into a five-year tradition.

    25 min
  • How'd You Learn to Be A Caregiver?

    What happens when “learning to be married” is put on hold "learning to advocate for a cancer patient"? Just four months into newlywed life, Jamie Kunkel became a full-time caregiver after her husband was diagnosed with cancer—and had to learn fast.

    From navigating Canada’s hospital system to communicating with medical teams, Jamie shares what it took to become an effective advocate, the skills she had to build on the fly, and how she’s still learning to balance caregiving with self-care. Now, through her podcast We Don’t Say Cancer, she’s helping others do the same.

    Join us for a conversation about learning under pressure, showing up with empathy, and finding strength in community.

    28 min
  • How'd You Learn to Build a Business? with Erika Siegner

    Sometimes you can learn at your own pace...and sometimes you have to learn fast. Erika Siegner has done both over her time opening three very different businesses! Join us as we discuss the importance of community, passion, and growth mindset in learning to be an entrepreneur.

    29 min
  • How'd You Learn to Earthquake-Proof Buildings? with Dr. Lydell Wiebe

    What if your learning community showed support by pointing out flaws...constantly? In the world of earthquake engineering, this is how you build each other up. Lives are on the line! Dr. Lydell Wiebe joins us to talk about how this kind of learning community works, how to deal with critical feedback, and where the joy comes from in earthquake engineering.

    28 min
  • How'd You Learn To Rap? with Peter Joynt a.k.a The Joynt

    This the story of a rapper with a stutter.

    Peter Joynt was a punk rock kid with a speech impediment who discovered hip-hop through his older brother. He quickly realized that his stutter disappeared when he was rapping, and the lessons learned in speech therapy helped him craft thoughtful and engaging rhymes. Today, he's a public speaker and prolific artist who spreads positivity and resilience all over Canada.


    Along the way, he dealt with industry rejection, bullying, and more. Hear how he overcame these and other obstacles on his learning journey on this double-sized episode!

    42 min
  • How'd You Learn To Farm? with Ryan Drudge & Sarah Jones of Easthope Market Garden

    What happens to the learning process when you only evaluate the results...not the process?


    Ryan and Sarah took on farming after a personal health journey helped them realize the benefits of organic food. Since then they've learned that farming isn't just growing veggies; it's carpentry, marketing, finance, and even a little bit of ornithology! Dive in for more on how they measure success in a learning journey, what keeps them motivated, and how their community has helped the gain the skills and knowledge they need to succeed.

    30 min
  • How'd You Learn To Be a Wine Sommelier? with Wes Klassen

    How do you learn a storied craft like wine tasting without losing your unique perspective?


    Wes Klassen learned about wine by necessity, but quickly discovered his passion for making this traditionally stuffy craft accessible to everyone. We talk about what the craft is, how to overcome the fear of it, and the importance of always having something new to learn.

    27 min
  • How'd You Learn to DJ? with Natalie 'NATMAC' McCormack

    Is DJing a creative process...or a technological one?


    It's both, of course. In this episode, you'll hear about how Natalie 'NATMAC" McCormack blended the power of music with a technological fascination. If you've ever felt blocked by uncooperative technology, unsure of whether you should trust your gut, or fatigued by failure, NATMAC's learning journey will give you tips, pointers and encouragement to navigate yours!

    26 min

About How'd You Learn To

From the publisher's feed

Lauren and Kerry were curious: how do experts become experts? Each episode of this podcast features an expert in a unique field -- Beekeeper! Magician! Tea Sommelier! -- discussing the highs and lows…