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PODCAST

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

society & culture philosophy

All Episodes

58:33

Rediscovering Non-Digital Joy

The Unobstructed Podcast ·

2026/01/28

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

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41:39

The Other Side Of Shame And Fear

The Unobstructed Podcast ·

2025/12/03

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

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80:04

The Trouble With Treating Jobs Like Trophies

The Unobstructed Podcast ·

2025/10/22

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

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34:47

Why I Wrote About Male Loneliness

The Unobstructed Podcast ·

2025/09/04

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

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54:28

Pitfalls Of A Polished Social Media Profile

The Unobstructed Podcast ·

2025/08/28

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

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53:30

Talking About Suicide Saves Lives

The Unobstructed Podcast ·

2025/08/20

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

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41:57

Taking Up Space Without Apologizing For Existing

The Unobstructed Podcast ·

2025/08/13

In this episode of The Unobstructed Podcast, Rachael and Derek talk about how words like "whatever" and "sorry" impact relationships. The conversation looks closely at the role of gender and societal expectations on our communication styles. But the biggest thing that comes up is the discussion about taking up space and setting personal boundaries.***The Unobstructed Podcast is for honest conversations about personal growth. Think of episodes like coffee talks about personal growth that reframe

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45:25

When You're Having An Off Day, Take The Day Off

The Unobstructed Podcast ·

2025/08/06

In this episode of The Unobstructed Podcast, Rachael and Derek chit chat about the cultural imbalance of personal and professional lives.The big question: can we cool it with the rush to add more just because we can?We do this thing where we feel the need to pretend we’re keeping up—even on normal days, where things go somewhat according to plan. Why do we do that, anyway? And wasn’t AI supposed to simplify day-to-day life instead of jamming more into it?You and I both know things never play out

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37:44

The Alpha Male Antidote

The Unobstructed Podcast ·

2025/07/30

This episode dives deep into emotional vulnerability, the societal expectations of masculinity, and how suppressing ourselves impacts our personal and professional lives. The conversation explores the challenges of expressing emotions, particularly for men, and the cultural norms that discourage vulnerability.It also touches on the importance of emotional intelligence, the need for authenticity in both personal and professional settings, and the evolving understanding of gender roles and emotional

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44:34

Pay Off Your Time Debt Using A Simple Reframe

The Unobstructed Podcast ·

2025/07/23

In our latest episode of the Unobstructed Podcast, we dive into the relationship between time management, productivity, and personal identity.If you only ever try to fix what you’re bad at, you might get better over time… but when you focus on what you’re already good at, you’ll make a lot more progress now.Understanding your character leads to better time management—and a more fulfilling life.***The Unobstructed Podcast is for honest conversations about personal growth. Think of episodes like

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36:34

Changing What You Accept For Yourself With A New Type...

The Unobstructed Podcast ·

2025/07/16

Instead of living the lives we want, we end up doing what we think we should. In this episode of the Unobstructed Podcast, Derek and Rachael dive into the power of overcoming the limits you give yourself. And then break down the idea of embracing the “why not?” mindset.Most of the limits we run into in life are ones that we place on ourselves. We become so sure about how the world works that we never stop to ask if we’re wrong. What if there’s an alternative to how we see things that might reshape

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46:49

How Childhood Dreams Predict The Person You Become

The Unobstructed Podcast ·

2025/07/09

In this episode of the Unobstructed Podcast, hosts Derek and Rachael take a nostalgic journey back to their childhood dreams and explore how those early aspirations have influenced their career paths. Rachael shares her story of wanting to become a lawyer, shaped by her role as the eldest sibling and her natural talent for debate. Meanwhile, Derek reflects on his love for acting and performance, inspired by iconic comedians, and how it evolved into a passion for communication strategy and

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20:47

On Letting Things Break

The Unobstructed Podcast ·

2025/06/25

I knew unsubscribes and lost clients would come with sharing more of my true self online. But it was a necessary step toward removing the many masks I’d picked up and glued onto myself over the years. Like many kids trying to blend in who grow into adults that feel left out.And let’s be clear… I’m not talking about fraud, here. I’m talking about diverting attention from things like: my sobriety, my queerness, my neurodivergence.So, I’ve been doing the scary thing and opening up about some stuff I’d

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43:04

The Most Important Skill For Becoming A Better...

The Unobstructed Podcast ·

2025/06/18

The difference between trying to be funny and opting to be vulnerable is a super fine line. And humor is a defense mechanism at its core.In this episode, Rachael and I talk about the improv rule of “yes, and.”In improv, “yes, and” is a way to expand a scene and make things more fun for the audience. In the workplace, it’s a tool for listening, growing, and co-creating without getting defensive.We chat about how it can change the way you show up on teams, in conversations with close friends, and even

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43:22

The Overlooked Half Of 'The Let Them Theory'

The Unobstructed Podcast ·

2025/06/11

Friction is the best teacher we’ll ever have, but the hardest to accept. It acts like a mirror. And our level of growth depends on our willingness to look at our own reflection. The Let Them Theory certainly helps to reframe how you can approach the unknown—specifically with empowered decision-making. Where it falls short is in accountability. This is the “Let Me” part of the theory, where you can decide what to do after you’ve let them be.We also talk about power, authority, and the ability to

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50:05

Learning How To Be Yourself Instead Of Staying Quiet

The Unobstructed Podcast ·

2025/06/04

It’s not your responsibility to manage how others perceive you.Most people won’t realize how much you filter yourself. At least, I’d hoped they wouldn’t. And it worked for a while. They might not always notice when you swap out your words mid sentence. Or when you redirect conversations away from personal details.But they will when you do it all the time. Even if it comes from a good place, like not wanting to be abrasive.In this episode, Rachael and I talk about what happens when filtering becomes

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47:16

Digging Out Of Content Fatigue With A Different...

The Unobstructed Podcast ·

2025/05/28

There’s a kind of exhaustion that comes from pretending to show up. You post because you’re “supposed to.” You rearrange your words to be seen a certain way. You aim for engagement, but not connection.But if you stop, your career suffers.People want a stamp of approval before they make a decision about you. And we’ve all collectively, stupidly, agreed to hawk our ideas to the highest bidder in exchange for that stamp.Bella Cowdin joins us to talk about the over saturation of content that’s watering

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45:45

The Invisible Tech Tax On Solopreneurs

The Unobstructed Podcast ·

2025/05/21

Before I ever made a dollar as a solopreneur, I’d spent hundreds and hundreds of hours breaking things in tech tool settings.No, not on purpose?Ok, that’s not entirely true…I definitely do like to take stuff apart to see how it works. And to test something I know won’t work, just to verify exactly what’ll happen when it fails.But this time was an accident, I pinky promise!!In this episode, Rachael and I dive into the reality of running a solo business and what you need to know about tools for

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30:44

The Art and Science of Becoming Happier

The Unobstructed Podcast ·

2025/05/14

It started with building a simple spreadsheet. It wasn’t fancy or complicated (ok, that’s not entirely true. But it doesn’t need to be… I just had fun building it that way). Truly I just wanted a way to gamify my way out of depression.What I discovered was that I almost always reported feeling great on the days I’d expect to feel terrible—huh?And the thing that surprised me most?I actually became three times happier.We also talk about:Why consistency is kinder than intensityWhy visibility matters

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33:38

Part 3 - What They Don't Tell You About Sobriety In...

The Unobstructed Podcast ·

2025/05/07

This is Part 3 of our conversation on sobriety in the workplace.Sober-curious conversations don’t always take place with bold bravado. Actually, I can say with a lot of confidence that they don’t. Often, they start quietly… through a throwaway comment.Or a casual text.Maybe an unassuming DM.Because I don’t know that I’d have gotten and stayed sober if I hadn’t read these two pieces of writing and had the conversations that followed:1. Sixty Meters to Anywhere by Brendan Leonard. 2. For Some Skiers,

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34 results

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