PODCAST · education
How'd You Learn To
by kerryobrien
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 of their learning journey to mastery.
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11
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.
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10
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.
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9
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.
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8
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.
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7
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.
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6
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.
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5
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!
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4
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.
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3
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.
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2
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!
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1
How'd You Learn To Run? with Lily Gilbert
What do you need to learn to move from hobby to habit? Lily went from running to fill time during the pandemic to running a half-marathon. Along the way, she learned how to hurdle (pun intended) imposter syndrome, sprained ankles, and soggy peach rings. Hear about how to leverage your intrinsic motivation, the importance of goals, and more here!
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0
How'd You Learn to Facilitate? with Catarina Haber
How do you learn a skill without practicing? Facilitation is a unique craft that you have to learn as you do it. Join Business Casual's Catarina Haber as she talks about her journey working without a net, finding out what facilitation is all about, and some of the key practices that have made her an in-demand facilitator.
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How'd You Learn to Meditate? with Nova Nicole
Unlike other skills we’ve talked about, people tend to seek out meditation when things aren’t going well. Nova Nicole was no different. The high-pressure world of hip hop had led her to therapy, which led her to formal meditation…which she thought would require her to change everything about herself. Join us to learn how meditation integrated with her life, how to embrace a beginner’s mindset, and the secret to overcoming your “mind monkey”.
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How'd You Learn to Perform Magic? with Ademola Adelakun
Have you ever made a mistake in front of a crowd? Do you think about it all the time? Ademola learned magic because he wanted an easy way to build connections with other people. And while he certainly got that, he also learned the value of improvisation, the necessity of persistence, and that we remember our mistakes much longer than others do. If you’ve got a mistake that’s been burning up your memory for months, or even years, that memory is keeping you from learning; this episode is a must-listen for you.
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How'd You Learn To Design Experiences? with Jordan Mandel
What do DJing, onboarding new employees, and corporate offsites have in common? They're experiences...and they require deep thought and skill to create. Jordan Mandel has done all these things, and he's begun to define what Experience Design is. Come learn how he's pulled from other disciplines like user experience and event planning (and also psycho-magic...don't worry, he explains it) to create and deploy this unique discipline.
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How'd You Learn To Breakdance? with Brandon Grant
What happens when you're the best breaker in your friend group...and then realize you're basic by any other standard? Brandon Grant takes us inside his journey of pushing through failure and earning confidence as a breakdancer, only to crash hard into the next level and start failing (and earning!) all over again. In between he finds community, willpower, and lessons about how to learn that translate into every other part of his life.
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How'd You Learn To Cosplay? with Jill Danaitis
Finn from Adventure Time, Jubilee of the X-Men, and Skeletor walk into a bar…and they’re all Jill Danaitis! Jill was cosplaying before she knew what cosplaying was. From making a niche Pokemon costume as a child to investing in a flocking machine (gotta get that facial fur just right!), hear about her journey to realize her vision, find her community, and maintain her joy in the face of roadblocks.
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How'd You Learn To Storytell? with Jonathan Barrie
What happens when a theater kid leaves the stage after high school? That passion goes dormant…until the chance to take a public speaking course at Second City pops up. Jonathan Barrie's passion for the stage in adolescence has translated to a passion for communicating with his audience with deeply personal stories. Hear all about how he’s learned to intentionally craft stories for maximum influence and impact.
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-7
How'd You Learn to Beekeep? with Chris Inch
Like many hobbies, beekeeping in Ontario has a high barrier to entry: climate, bylaws, not liking being stung, and more. None of these deterred Chris Inch from not only becoming a beekeeper, but becoming a resource for others looking to get into the hobby. If you need inspiration on creative ways to learn and grow in your passions, this is the episode for you.
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-8
How'd You Learn To Network? with Tobi Oluwole
What happens when a little kid moves countries over and over and over again? If you're Tobi Oluwole, you learn how to quickly build connections with others...and that lays the foundation for becoming a master networker. As of this writing, Tobi has almost 200K followers on LinkedIn (and will likely have more by the time you finish listening). Check out this conversation to discover the difference between audience and community, and how that understanding will help you expand your personal and professional networks.
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-9
How'd You Learn To Podcast? with Justine Yang
Justine Yang was travelling and finding it tough to keep her friends and family updated on what she was doing. So naturally, she started a podcast! And through that, she learned how to bring her authentic voice, how to know when you're ready to go public with your authentic voice, and how to leverage early wins as momentum to keep going. Check out this podcast (and hers!) to learn more!
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How'd You Learn To Be a Tea Sommelier? with Sheena Brady
Sheena Brady was a rising star in the hospitality industry when she was given an assignment: learn everything she could about traditional tea services. Today, she's a certified Tea Sommelier with a thriving tea business. But what does it mean to be a Tea Sommelier? What do you have to learn? Lauren and Kerry sit down with Sheena to hear about how she went from trying to detect hints of pencil shavings in wine to creating her own tea blends.
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Welcome to How'd You Learn To!
This quick intro tells you everything you need to know about why we started the show. Looking forward to journeying with you!
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ABOUT THIS SHOW
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 of their learning journey to mastery.
HOSTED BY
kerryobrien
CATEGORIES
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