The Unobstructed Podcast

Derek MacDonald

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 31

    Facing Death And Embracing Grief With Michaela Kellogg

    This episode of The Unobstructed Podcast is about grief, empathy, and learning how to talk about death instead of tiptoeing around it. Michaela Kellogg is a creative director and writer. And she’s also the voice behind The Near Death Project, a publication exploring death and grief. It started as a way to feature conversations with people who live and work near death—religious leaders, hospice workers, doctors, mediums—as well as those who have nearly died or are nearing the end of life themselves. Tragically, the project became far more personal following the unexpected death of her nine-year-old son, Ben. In this conversation, Michaela talked a whole lot about paying attention to the “little things” in life. So I really wanted to dig into where that came from. Did she always do that? Or was it something she learned along the way? After Ben’s death, Michaela had to figure out how to live a life that made space for gratitude and grief at the same time. So, a lot of her writing now reads as a collection of thank you letters that focus on the surprising and generous ways people show up for one another during the tragic, most brutally uncomfortable moments in life. Since there are no clear instructions for navigating stuff like that, she hopes all she’s come to understand about her own grief can help others to do the same. This conversation was both difficult and immensely heartwarming. While we planned to talk about grief, we actually spent a surprising amount of time discussing the stories we tell ourselves and why they influence our wellbeing so much. In the lead-up to recording this episode, I didn’t expect self-talk to come up nearly as much as it did. Turns out that Michaela talks to herself like a coach, which Caleb and I each do, too. Her new children’s book, Buds, aims to help folks take that a step further by introducing themes of life and loss to talk about with one another in more approachable ways. One thing that stuck with me was how Michaela advocated for directly acknowledging our discomfort rather than ignoring it. And that lines up with something I’ve been working on for years: the idea that we don’t always need to fix things (or cheer people up), and that being present is usually enough. *** 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. 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

  3. 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

  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

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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