The Unobstructed

By 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.

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FAQs about The Unobstructed:

How many episodes does The Unobstructed have?

The podcast currently has 33 episodes available.

The Unobstructed episodes:

November 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, 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
...more
42min
October 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, 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
...more
1h 21min
September 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, 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
...more
35min
August 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, 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
...more
55min
August 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
...more
54min
August 13, 2025 Taking Up Space Without Apologizing For Existing
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: 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
...more
42min
August 06, 2025 When You're Having An Off Day, Take The Day Off
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 like we thought they would. So of course we’re not fully keeping pace like we feel we should, either.
Rachael thinks AI agents will alleviate this burden from people. She’s become pretty good at building them herself. Most people don’t know how to do this yet. They’re stuck with the added pressure it’s creating, though.
So when Rachael said “I was having a shitty day yesterday,” I loved hearing about how she handled 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 Unobstructed at explore.theunobstructed.com/subscribe
...more
46min
July 30, 2025 The Alpha Male Antidote
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 expression.
***
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
...more
38min
July 23, 2025 Pay Off Your Time Debt Using A Simple Reframe
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: 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
...more
45min
July 16, 2025 Changing What You Accept For Yourself With A New Type Of Storytelling
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 what we believe is possible?
***
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
...more
37min

FAQs about The Unobstructed:

How many episodes does The Unobstructed have?

The podcast currently has 33 episodes available.