The Unobstructed Podcast

Derek MacDonald
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  • Philosophy
  • Updated Monthly

Listen in on conversations about navigating daily life with more agency and clarity. Sometimes, a new way of seeing things is all it takes to get unstuck. New episodes every month. explore.theunobstructed.com

  1. Jul 10

    Auditioning For The Wrong Roles In Life

    This episode of The Unobstructed Podcast is about “leveling up” in life by collecting skills and experiences. In this conversation, Caleb framed skill-building like role-playing. Once upon a time, he was a football player. Then he found theater. He still carries lessons he learned from both, but says he’s come to look at the chapters of his life as time invested in playing a role. That’s also the lens through which he decides what to do next—the role(s) to audition for so to speak. To me, that’s like stacking transferable skills. I didn’t really expect us to get into social masking or code switching, but I’m psyched we did. A lot of how we learn to navigate the world comes from stuff that shaped us during childhood. It seems like that’s when we experience being beginners the most. Then, somewhere along the way, we tend to stop trying new things. Caleb brought up the concept of being a “jack of all trades,” which is how we got to talking about the role of observation, impersonation, and leveling up… a powerful equation, so long as you also remember to get rid of what no longer serves you. Auditioning for the wrong roles in life is how you get good enough to actually land the ones you want. *** The Unobstructed Podcast: Listen in on big thoughts and small steps for navigating agency, grief, and creativity in daily life. New episodes every month. About the hosts: Derek MacDonald — writer and systems consultant who likes building websites, running, and getting lost in a good book with a strong cup of coffee. You can learn more about Derek, his writing, and his live storytelling at derekmacdonald.com. Caleb Walker — digital marketer by trade, outdoorsman, hobbyist chef, and avid reader who just likes hanging out with his family and spending time outside. Read the latest from Derek and Caleb at theunobstructed.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

  2. Jan 28

    Rediscovering Analog Joy

    This episode of The Unobstructed Podcast is about rediscovering joy. It's a topic that friend of the pod, Caleb Walker, brought up recently. Specifically, he’s seeing an uptick in a trend called “kidulting,” where people are returning to hobbies they loved and found joy in as kids, but that they’ve left behind in adulthood. We both come from a background in marketing where, by day, we’re forced to be very digitally integrated. Likely as a result of that, we’ve been trying to find ways of distancing ourselves from an “always on” vibe when not working. Frankly, it’s hard. It’s also become impossible to ignore the growing connectivity-fatigue that’s showing up, online of all places. So, at least we know we’re not the only ones wrestling with it? The part of our conversation I loved most was talking about how social media skews self-worth. It took a very different turn from the somewhat normally discussed side-effects of comparison culture. Instead, we dug deeper into what we’re seeing this pattern do to the ways we look for affirmation (online and in real life). Caleb surprised me with a few of the ways he’s making space for analog and low-tech joy. Music and mountain biking, I’d expected; but some of the other things he’s getting into got my own wheels turning on how I can tap back into joy beyond digital. We talk about all of this and more in the episode. *** The Unobstructed Podcast: Listen in on big thoughts and small steps for navigating agency, grief, and creativity in daily life. New episodes every month. About the hosts: Derek MacDonald — writer and systems consultant who likes building websites, running, and getting lost in a good book with a strong cup of coffee. You can learn more about Derek, his writing, and his live storytelling at derekmacdonald.com. Caleb Walker — digital marketer by trade, outdoorsman, hobbyist chef, and avid reader who just likes hanging out with his family and spending time outside. Read the latest from Derek and Caleb at theunobstructed.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

  3. 11/26/2025

    The Other Side Of Shame And Fear

    This episode of The Unobstructed Podcast is about getting out of your own way—about being caught between shame, fear, and the path to finally feeling clear. The same week I got sober I also started a new job, went through a breakup, and moved across the country. That was almost four and a half years ago. All of that kinda, sorta, really, definitely sucked… but it was also one of the biggest (and most positive) turning points in my life. Sobriety reshaped my approach to creativity and stability, but only because of what it exposed. This is at the heart of what we talk about in the episode. onward. -dmac *** The Unobstructed Podcast: Listen in on big thoughts and small steps for navigating agency, grief, and creativity in daily life. New episodes every month. About the hosts: Derek MacDonald — writer and systems consultant who likes building websites, running, and getting lost in a good book with a strong cup of coffee. You can learn more about Derek, his writing, and his live storytelling at derekmacdonald.com. Caleb Walker — digital marketer by trade, outdoorsman, hobbyist chef, and avid reader who just likes hanging out with his family and spending time outside. Read the latest from Derek and Caleb at theunobstructed.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

  4. 10/22/2025

    The Trouble With Treating Jobs Like Trophies

    This episode of The Unobstructed Podcast is about trade-offs. Caleb Walker and I recently chatted about the pitfalls of polished social media profiles (he's the Managing Director of Digital Strategy for an agency). Part of that conversation touched on how our digital presence can impact job opportunities. We felt there was more to talk about, so we got together to keep digging. This time, we wanted to understand what it’s like to bust your ass to get a job, only for the reality of the role to be completely different than you’d expected. It’s hard to come to terms with the gap between where you are and where you want to be. I’ve always believed I could do something about that, but I wasn’t always as clear on how. It wasn’t until my twenties that I felt like I’d started to figure it out. And it wasn’t until my thirties that I realized I was wrong. *** The Unobstructed Podcast: Listen in on big thoughts and small steps for navigating agency, grief, and creativity in daily life. New episodes every month. About the hosts: Derek MacDonald — writer and systems consultant who likes building websites, running, and getting lost in a good book with a strong cup of coffee. You can learn more about Derek, his writing, and his live storytelling at derekmacdonald.com. Caleb Walker — digital marketer by trade, outdoorsman, hobbyist chef, and avid reader who just likes hanging out with his family and spending time outside. Read the latest from Derek and Caleb at theunobstructed.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

  5. 09/04/2025

    Why I Wrote About Male Loneliness

    This episode of The Unobstructed Podcast is a personal reflection from Derek MacDonald on self-discovery, communication, and personal growth. I get into my self-inflicted social isolation as well as my changed relationship with the outdoors. I used to be very active… and I’m not anymore. Before my traumatic brain injury, I worked, lived, and socialized in the world of outdoor sports. Then, after the accident, I’d hoped I could love the outdoors again in ways where my livelihood wasn’t attached to it. And I haven’t been able to recover that, which is hard. Repercussions hit my social life too. Which is why I’m so focused on becoming better at communicating. I try to share things in ways that allow people to grab on and join in. I recently wrote an essay about male loneliness, admitting that I’m lonely in my social life, and that essay took off on Substack. People really latched on. In under a week, it got more views than anything I’ve written in the last year—more likes, comments, shares. Part of my loneliness came from a self-imposed isolation over the last few years. And it was intentional in order to work on myself. Everything I’ve been working on lately has been in service of finding my voice again and feeling good about using it. *** The Unobstructed Podcast: Listen in on big thoughts and small steps for navigating agency, grief, and creativity in daily life. New episodes every month. About the hosts: Derek MacDonald — writer and systems consultant who likes building websites, running, and getting lost in a good book with a strong cup of coffee. You can learn more about Derek, his writing, and his live storytelling at derekmacdonald.com. Caleb Walker — digital marketer by trade, outdoorsman, hobbyist chef, and avid reader who just likes hanging out with his family and spending time outside. Read the latest from Derek and Caleb at theunobstructed.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

  6. 08/28/2025

    Pitfalls Of A Polished Social Media Profile

    In this episode of The Unobstructed Podcast, Caleb Walker and I chat about the crotchety complexities of social media. Specifically, with regard to personal identity. His perspective was especially interesting, given his close-knit relationship with social media as the Managing Director of Digital Strategy at his agency. This conversation hit home for me, as I’ve often found myself wrestling with how to present my true self in a world that seems to prioritize professional titles over personal stories. One of my favorite parts of our discussion was talking about the pressure to maintain a polished online persona. Caleb and I covered the growing demand for authenticity, both from individuals and brands, and how he balances his personal and professional identity. In lieu of promoting himself, Caleb would like you to read these books: All the Truth is Out, by Matt BaiThe Nature Fix, by Florence WilliamsThe Chaos Machine, by Max Fischer *** The Unobstructed Podcast: Listen in on big thoughts and small steps for navigating agency, grief, and creativity in daily life. New episodes every month. About the hosts: Derek MacDonald — writer and systems consultant who likes building websites, running, and getting lost in a good book with a strong cup of coffee. You can learn more about Derek, his writing, and his live storytelling at derekmacdonald.com. Caleb Walker — digital marketer by trade, outdoorsman, hobbyist chef, and avid reader who just likes hanging out with his family and spending time outside. Read the latest from Derek and Caleb at theunobstructed.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

  7. 08/25/2025

    The Unobstructed Podcast

    Listen in on conversations about navigating daily life with more agency and clarity. Sometimes, a new way of seeing things is all it takes to get unstuck. New episodes every month. About the hosts: Derek MacDonald — writer and systems consultant who likes building websites, running, and getting lost in a good book with a strong cup of coffee. You can learn more about Derek, his writing, and his live storytelling at derekmacdonald.com. Caleb Walker — digital marketer by trade, outdoorsman, hobbyist chef, and avid reader who just likes hanging out with his family and spending time outside. Read the latest from Derek and Caleb at theunobstructed.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

  8. 08/20/2025

    Talking About Suicide Saves Lives

    In this episode of The Unobstructed Podcast, Derek and Rachael have an important conversation about mental health and substance abuse. More specifically, we talk openly about the stigma surrounding suicide and addiction. This episode is about creating empathy, understanding, and support for those struggling, with ways of recognizing and responding to mental health crises. If you or someone you know is struggling or in crisis, help is available. Call or text 988 or go to 988lifeline.org to chat with the 988 Suicide & Crisis Lifeline. *** The Unobstructed Podcast: Listen in on big thoughts and small steps for navigating agency, grief, and creativity in daily life. New episodes every month. About the hosts: Derek MacDonald — writer, thinker, coffee drinker. Started Becoming Unobstructed after 15+ years in marketing, software systems, outdoor education, and leadership development to share what he's learned with others. Rachael Sink — owner and business consultant at Rachael's Ink, LLC, a HubSpot Gold Solutions Partner agency. Visit Derek’s website: theunobstructed.com Visit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

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About

Listen in on conversations about navigating daily life with more agency and clarity. Sometimes, a new way of seeing things is all it takes to get unstuck. New episodes every month. explore.theunobstructed.com

Information

  • Creator
    Derek MacDonald
  • Years Active
    2025 - 2026
  • Episodes
    36
  • Rating
    Explicit
  • Copyright
    © Unobstructed
  • Show Website
    The Unobstructed Podcast