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The Disorienting Dilemma

by Podstarter

Two longtime friends, both Canadian – one black, one white, and both men – explore what it looks like to adopt the mindset of an inclusive society. Instead of asking, ”How do we get there?”, Jake and Chris discuss what does it look like to act as if we’re there already.

Publisher-supplied feed metadata · PodParley refreshed Jun 30, 2026 · Source feed

Episodes

  1. Bridging Divides: Lessons in Belonging from a Baltimore Neighborhood

    In the heart of West Baltimore, a neighbourhood grapples with the profound impact of systemic inequities that have shaped its trajectory for generations. Amidst the vacant lots and dilapidated houses lies a community striving to reclaim its narrative and forge a path towards resilience and…

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  2. The Complicated Emotions of Leaving People, Places, and Projects

    In this episode, Jake shares a disorienting dilemma he experienced recently when visiting a place that used to hold massive importance to him. The emotions this left him with were unexpected to say the least. Chris joins in on the discussion, connecting Jake's story to one of his own - a camping...

  3. The Pain of Exclusion and the Fragility of Social Identity

    In this deeply personal episode, Chris and Jake explore how even small moments of exclusion can leave lasting scars by threatening our sense of belonging and social identity. They connect a story from Chris' past to the recent Republican response to the State of the Union, showing how identities...

  4. Navigating Meaning in a Changing World: Insights on Language, Identity, and Social Transformation

    In an era marked by rapid change and increasing complexity, the ways we communicate, understand ourselves, and engage with society are constantly evolving. Just as new slang terms like "mewing" and "rizz" can spread like wildfire among younger generations, leaving older folks scratching their...

  5. Cancelling People Doesn’t Make Us Safer - GUEST: Melissa Mackay (REBROADCAST)

    This episode originally aired September 7, 2022. Did this episode get you thinking, or did we miss the mark? Let us know by leaving us a message on SpeakPipe. Good friends will give truthful feedback, even when it’s embarrassing, because they care. It’s the spinach in teeth moment or the toilet...

  6. When Human Suffering Becomes White Noise: Looking Away from Oppression and Finding the Next Outrage

    Shocking images of bloodshed in war-torn regions can spur reactions ranging from momentary sympathy to outrage driving donations or protests. Yet what causes some global crises to utterly capture international attention while others fade into the backdrop of normalcy? The spotlight's fluctuations...

  7. Clashing Perspectives, Shared Humanity: Finding Common Ground in Divided Times

    Conflict seems ubiquitous in modern society, whether simmering tensions around inequality or openly violent clashes rooted in complex geopolitical and historical dynamics. Making sense of these multifaceted disputes requires moving beyond surface-level takes towards more thoughtful examination....

  8. Decoding Disaster: The Mind's Path to Resilience and Response

    When crisis hits, our logical brains often revert back to primeval instincts. But what if we could train our minds to transcend the urge to panic in the face of chaos? That is the premise explored in this episode, as the hosts dive into the human capacity to overcome fear in the most unexpected...

  9. Navigating the “Overwhelm” on the Journey Towards Growth

    We all have moments when things pile up and we feel overwhelmed. Work deadlines collide with personal responsibilities, inbox notifications keep dinging, and our mental bandwidth reaches max capacity. In times like these, it’s easy to shut down or check out from all the pressure. This survival...

  10. The Multifaceted Equation: Busyness, Helping, and Emotional Wellness in Modern Life

    Did this episode get you thinking, or did we miss the mark? Let us know by leaving us a message on SpeakPipe. Introduction In a society where "busy" has become the default response to "How are you?", the latest episode of the "Disorienting Dilemma" podcast offers an insightful deep-dive into the...

  11. Et tu, Jarvis?

    In this episode, Chris and Jake delve into multifaceted aspects of team dynamics and communication nuances. From dissecting the essence of high-performing teams to unravelling the delicate balance between the urgency to say something and the need to shut up. At one point, Chris wonders aloud…

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  12. The Intersections of Faith, Activism, Justice, and Personal Growth

    The intersection of faith, activism, justice, and personal growth is often a complex and nuanced space, where philosophical musings meet the very real challenges of our world. This article delves into these intricate relationships, aiming to provide you with fresh perspectives that are as...

  13. The Inward Journey - Unraveling the Complexities of Personal Transformation

    Today, we're diving deep into an intriguing topic that's been at the heart of our podcast discussions lately. We're shifting gears in our third season, turning the spotlight onto an aspect of personal and societal change that's often overlooked: the inward journey towards becoming more inclusive...

  14. ‘Tis the End of the Season

    Did this episode get you thinking, or did we miss the mark? Let us know by leaving us a message on SpeakPipe. Jake and Chris do a year-end recap of their most notable moments from Season Two. With the links to the referenced episodes below, listeners are encouraged to circle back for another…

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  15. Why Doesn’t America have a State Religion?

    Did this episode get you thinking, or did we miss the mark? Let us know by leaving us a message on SpeakPipe. According to Pew Research, out of 199 countries and territories, “More than 80 countries favour a specific religion, either as an official, government-endorsed religion or by affording…

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  16. Transactional versus Transformative Volunteering: A Tale of Two Jarvises

    Did this episode get you thinking, or did we miss the mark? Let us know by leaving us a message on SpeakPipe. When we first volunteer to help others, most people begin with a desire to ‘make a difference’ or ‘give back’. As we continue in the volunteer journey, we notice a strange phenomenon: the...

  17. The time Jake almost killed his uncle during a Hurricane

    Did this episode get you thinking, or did we miss the mark? Let us know by leaving us a message on SpeakPipe. Jake shares a recent account of being ‘voluntold’ during a hurricane in Nova Scotia earlier this year. Although Jake's poor math skills almost ended in tragedy for his uncle, he gained…

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  18. Our Unhoused Neighbours May Not Be Who You Think They Are - GUEST: Andy Reed

    Did this episode get you thinking, or did we miss the mark? Let us know by leaving us a message on SpeakPipe. Jake and Chris dig a bit deeper on the topic of homelessness and unhoused neighbours. Are the stereotypes society holds about citizens who are unhoused accurate? Or maybe, anyone of us...

  19. Not in My Backyard... or My Community Park, Either!

    Did this episode get you thinking, or did we miss the mark? Let us know by leaving us a message on SpeakPipe. Jake and Chris stare uncomfortably at the privilege they experience every time they leave their houses, never worrying about whether the place will be there when they get back. Far more...

  20. “Becoming a Changemaker” - GUEST: Alex Budak

    Did this episode get you thinking, or did we miss the mark? Let us know by leaving us a message on SpeakPipe. Jake and Chris are joined by the author of “Becoming a Changemaker’, Alex Budak. Together, they explore what it means to be a ‘changemaker’, both in terms of how to make change happen in...

  21. Cancelling People Doesn’t Make Us Safer - GUEST: Melissa Mackay

    Did this episode get you thinking, or did we miss the mark? Let us know by leaving us a message on SpeakPipe. Good friends will give truthful feedback, even when it’s embarrassing, because they care. It’s the spinach in teeth moment or the toilet paper dragging from the shoe. Better to hear it…

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  22. An Unexamined Life – GUEST: Scott Lynch

    Did this episode get you thinking, or did we miss the mark? Let us know by leaving us a message on SpeakPipe. Over 25 years ago, Scott Lynch, along with other local “punks”, participated in a series of grassroots anti-racism efforts in Halifax, Nova Scotia. He sits down in studio with his…

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  23. Too Tired to be Woke

    Did this episode get you thinking, or did we miss the mark? Let us know by leaving us a message on SpeakPipe. Chris and Jake chat through the difference between radicalization and wokeness, and how sometimes they appear to be the same thing from the “outside”. In considering the influences of...

  24. Crumbs in The Butter

    Did this episode get you thinking, or did we miss the mark? Let us know by leaving us a message on SpeakPipe. Chris shares some ‘rules’ he learned as a child that he came to understand (later in life) were not exactly universal, but rather preferences and meanings specific to his family. Jake and...

  25. Feeling Like a Fraud

    Did this episode get you thinking, or did we miss the mark? Let us know by leaving us a message on SpeakPipe. When someone tells you that you don’t belong here, it can hurt – a lot! What happens when that voice comes from inside your head? This week, Chris and Jake take on “Imposter Syndrome” and...

  26. Understanding the Assignment - Sabotage the System.

    Did this episode get you thinking, or did we miss the mark? Let us know by leaving us a message on SpeakPipe. Chris uses his hot question “hall pass” from Jake as he tries to understand a lived experience that he never considered until now. They discuss why going straight to “asking your Black...

  27. Radicalizing Jake's Dad

    Did this episode get you thinking, or did we miss the mark? Let us know by leaving us a message on SpeakPipe. Jake playfully tries to convince his Dad that his conservative and traditional “Canadian” values are under attack and they need defending. Chris worries aloud that he might be oversharing...

  28. Sticks, Stones, Exclusion and Broken Bones

    Did this episode get you thinking, or did we miss the mark? Let us know by leaving us a message on SpeakPipe. TW: Within the first 10 minutes of this episode, Chris and Jake reference in passing an incident of institutionalized sexual abuse and despite having permission have beeped the name of...

  29. Farming Out Your Diversity Training

    Did this episode get you thinking, or did we miss the mark? Let us know by leaving us a message on SpeakPipe. In this episode, Jake reminds Chris of the time some well-intentioned soup kitchen volunteers wanted to help “Billy-bob” change his life by sending him off to the church farm to be...

  30. A Slap Back to Reality

    In this episode, Chris and Jake attempt to dig into what matters most about Will Smith slapping Chris Rock during the 2022 Academy Award show. By interrogating what else was happening in that moment, they discuss how traditional responses to incidents of workplace violence often focus to narrowly...

  31. Are we still monetizing slavery?

    Did this episode get you thinking, or did we miss the mark? Let us know by leaving us a message on SpeakPipe. In this episode, Jake and Chris explore parallels between an Ebony Magazine’s 1950’s marketing campaign ‘‘The Secret of Selling the Negro” and current Diversity, Equity and Inclusion…

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  32. Yes, We Are All Suffering – But I Can’t Help You. You’re Not One Of Us.

    Did this episode get you thinking, or did we miss the mark? Let us know by leaving us a message on SpeakPipe. Even in the most difficult and trying situations, human beings tend to ‘other’ people who may be experiencing the same trauma and difficulties, because ‘they’ are not ‘us’. We see this...

  33. Why Doing The Right Thing Will Feel Bad Sometimes: Your Brain Is Changing

    Did this episode get you thinking, or did we miss the mark? Let us know by leaving us a message on SpeakPipe. In this episode, Jake shares a personal story where doing the right thing left him feeling terrible for weeks. Together, we explore why doing the right thing sometimes makes us feel bad....

  34. Season 2 Trailer

    Chris and Jake are excited to return for a second season to explore the disorienting dilemmas we face as we try to answer the question: How do I think, believe and act in an inclusive world? Stay tuned! Disorienting Dilemma on YouTube https://www.rw.institute/the-disorienting-dilemma

  35. Reverse Day and The Modern Bully

    No longer the 5th grader shoving you into a locker for your lunch money, the bully's tactics have changed, especially in the workplace. Jake and Chris discuss. Click here for more. Heart Politics by Fran Peavey

  36. Bitcoin, Beanie Babies, and Framing the Experience

    What does Bitcoin and Beanie Babies have in common? Not a lot, it turns out, but leave it up to Chris and Jake to connect those dots, which somehow leads to a highly engaging conversation on the importance of framing the volunteer experience. Links and resources.

  37. Chris' Tourette's and Neurodiversity

    In a strikingly personal episode, Chris opens up about his experience with Tourette's Syndrome, to which Jake has had a front row seat since its onset. Along the way they cover microaggressions, neurodiversity in and out of the workplace, and – this may be a new one for some of you –...

  38. The Problem with Helping

    Giving back has a colonialism problem. However in the right place their heart is, the "helper" is often the gatekeeper, delegating resources from a position of power, and in effect othering the "lesser." What if instead they wrote a really terrible Christmas song? Read more on the episode here.

  39. Please Don't Take My Dog, pt. II: Context Matters

    Chris and Jake continue their conversation on restorative justice. David Eagleman - Livewired

  40. Please Don't Take My Dog, pt. I: Restorative Justice

    A woman's dog is taken. Police respond and charges are pressed, but she still doesn't have her dog. What good is a justice system that benefits "the people," but not victims?

  41. Man, I Knew that Guy: On Cancel Culture

    "If we delete it, maybe it didn't happen." Despite the producer's best efforts to, ahem, cancel this episode, Jake and Chris open wide the can of worms known as cancel culture. More resources and links. Brandi Carlile - That Wasn't Me

  42. The One that Caught Fire: Why Do We Help Each Other?

    Jake and Chris reminisce on how they met (though their accounts of the experience vary), leading to a discussion on what may surprise some to be among the most ancient of human behaviors: helping.

  43. Smoke and Mirrors: Performative Allyship and Virtue Signaling in CSR

    Corporations are skilled at presenting comforting statistics that demonstrate their commitment to diversity, equity, and inclusion – and sometimes, they even take a small stand. But are they just virtue signaling? Experts in the field of CSR and Restorative Justice, Chris and Jake dissect the…

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  44. What About Witches and Dracula? Cultural Appropriation

    Jake thinks it's theft, Chris is curious about how cultural appropriation is different from assimilation. Visit The Disorienting Dilemma's website for show notes and more info.

  45. Do You Remember Ever Ever Ever Being Asked to Leave? Unlearning Bias

    Chris and Jake discuss the April 2018 incident where two black men were asked to leave a Philadelphia Starbucks and then arrested for ... being black. What should a corporate response to racism look like? And is one-and-done diversity training even effective? For show notes and more info, click...

  46. What the Hell is Wrong with Chris? Workplace Equity and Power Dynamics

    Chris experiences a disorienting dilemma upon learning that his aggressive, straightforward approach in work meetings does not always translate well. For more info and show notes, click here.

  47. What if No One Listens? A Disorienting Dilemma

    Chris and Jake dive in the deep end as they question their decision to start a podcast, reflect on the relevance of two male voices in the world of inclusivity, and encounter an unexpected disorienting dilemma in the process. Click here or for show notes and resources.

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ABOUT THIS SHOW

Two longtime friends, both Canadian – one black, one white, and both men – explore what it looks like to adopt the mindset of an inclusive society. Instead of asking, ”How do we get there?”, Jake and Chris discuss what does it look like to act as if we’re there already.

HOSTED BY

Podstarter

Frequently Asked Questions

How many episodes does The Disorienting Dilemma have?

The Disorienting Dilemma currently has 47 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.

What is The Disorienting Dilemma about?

Two longtime friends, both Canadian – one black, one white, and both men – explore what it looks like to adopt the mindset of an inclusive society. Instead of asking, ”How do we get there?”, Jake and Chris discuss what does it look like to act as if we’re there already.

How often does The Disorienting Dilemma release new episodes?

The Disorienting Dilemma has 47 episodes. Check the episode list to see recent publication dates and frequency.

Where can I listen to The Disorienting Dilemma?

You can listen to The Disorienting Dilemma on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.

Who hosts The Disorienting Dilemma?

The Disorienting Dilemma is created and hosted by Podstarter.
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