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The Unobstructed

The Unobstructed

Written by: Derek MacDonald
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Listen in on big thoughts and small steps for navigating agency, grief, and creativity in daily life. New episodes every month.

explore.theunobstructed.comDMDC Systems, LLC
Philosophy Self-Help Social Sciences Success
Episodes
  • The Other Side Of Shame And Fear
    Nov 26 2025

    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, 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 Becoming Unobstructed at explore.theunobstructed.com/subscribe
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    42 mins
  • The Trouble With Treating Jobs Like Trophies
    Oct 22 2025

    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, 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 Becoming Unobstructed at explore.theunobstructed.com/subscribe
    Show More Show Less
    1 hr and 20 mins
  • Why I Wrote About Male Loneliness
    Sep 4 2025

    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, 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 Becoming Unobstructed at explore.theunobstructed.com/subscribe
    Show More Show Less
    35 mins
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