The Unobstructed Podcast

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 — Editorial leader sharing the small, but meaningful, moments of daily life. Started Unobstructed after a 15+ year journey in marketing, outdoor education, and leadership development.Rachael Sink — owner and business consultant at Rachael's Ink, LLC, a HubSpot Gold Solutions Partner agency.Visit Derek’s website: derekmacdonald.comVisit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

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 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 — Editorial leader sharing the small, but meaningful, moments of daily life. Started Unobstructed after a 15+ year journey in marketing, outdoor education, and leadership development.Rachael Sink — owner and business consultant at Rachael's Ink, LLC, a HubSpot Gold Solutions Partner agency.Visit Derek’s website: derekmacdonald.comVisit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

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 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 — Editorial leader sharing the small, but meaningful, moments of daily life. Started Unobstructed after a 15+ year journey in marketing, outdoor education, and leadership development.Rachael Sink — owner and business consultant at Rachael's Ink, LLC, a HubSpot Gold Solutions Partner agency.Visit Derek’s website: derekmacdonald.comVisit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

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 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 — Editorial leader sharing the small, but meaningful, moments of daily life. Started Unobstructed after a 15+ year journey in marketing, outdoor education, and leadership development.Rachael Sink — owner and business consultant at Rachael's Ink, LLC, a HubSpot Gold Solutions Partner agency.Visit Derek’s website: derekmacdonald.comVisit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

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 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 — Editorial leader sharing the small, but meaningful, moments of daily life. Started Unobstructed after a 15+ year journey in marketing, outdoor education, and leadership development.Rachael Sink — owner and business consultant at Rachael's Ink, LLC, a HubSpot Gold Solutions Partner agency.Visit Derek’s website: derekmacdonald.comVisit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

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.comVisit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

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.comVisit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

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.comVisit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

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.comVisit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

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.comVisit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

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.comVisit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

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 storytelling.Together, they discuss the pressures of choosing a career path, the unexpected turns life can take, and the value of non-traditional learning experiences. This episode is a heartfelt exploration of ambition, growth, and the importance of following one's true calling. Tune in to discover how childhood dreams can shape who we become and the lessons learned along the way.***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.comVisit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

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 long struggled with. My hope was to reclaim a bit more of myself while offering thoughts from what I’ve learned by working through things along the way. As expected, some readers and clients showed themselves the door.Trying to force this newsletter and podcast to neatly overlap with my business failed. So I’m letting it break.***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.comVisit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

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 in the chatter of your own inner monologues.***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.comVisit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

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 reprimand.Oh, and the problem with meeting confusion with aggression.***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.comVisit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

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 an engrained personality trait (a la yours truly).***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.comVisit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

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 everything down for all of us. On many, many platforms, but especially on LinkedIn.Bella’s a RevOps consultant, Hubspot Admin, and all-around systems badass. She also has a background in snow science. Which turned out to be a pretty fitting metaphor for the ol’ avalanche of thought leadership on LinkedIn.Aside from sharing a lot of laughter, she offered some very unique insight. It was really interesting to see how she thinks about posting online. She’s refreshingly honest. And it helped us get to the bottom of some hidden, but pretty big, contributing factors to the LinkedIn content mess.You can find Bella (ironically) on LinkedIn and also on her website.***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.comVisit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

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 strategic and technical work at extreme levels.As your tech chops improve, it gets harder to explain what you actually do to those who can’t see behind the curtain.We talk about what it actually takes to show the value of invisible systems, and why it’s easy to get stuck between all tools that don’t talk to each other. That’s where I also share the lovely story of how I accidentally broke this very podcast’s RSS feed.***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.comVisit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

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 intensity.Why visibility matters when your energy is low.How I built a system that helped me feel like myself again.What “cognitive idling” is and why it drains your motivation.***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.comVisit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

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, Drugs and Alcohol Are Fun, But For Me it Was Darker by Paddy O’Connell.Rachael and I also talk about becoming “sober curious” in the first place. We also discuss seeing others do the damn thing and finding the courage to ask them how they did it.Oh, and navigating the workplace stigma of telling people you don’t drink.***If you or someone you know is struggling with addiction or looking for resources to help get sober, aa.org is a place you can visit to learn more about getting support.***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.comVisit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

This is Part 2 of our conversation on sobriety in the workplace.Sometimes staying sober means saying no to the invite.This one’s not about quitting so much as it’s about the stuff that happens once you do. Like, after you’ve made a decision to stop drinking… but people keep asking why.We talk about the new realities of sobriety and work life: from happy hour and ordering dinner to wondering if kombucha or tiramisu counts.***If you or someone you know is struggling with addiction or looking for resources to help get sober, aa.org is a place you can visit to learn more about getting support.***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.comVisit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

You might not recognize your rock bottom until later. Sometimes you know quick. But other times, it’s a quiet realization. One that unfolds slower, like pulling the bandaid instead of ripping it off.And we wanted to talk about that. The parts of getting sober that don’t have a manual.No, this isn’t an AA meeting. We’re not sharing inventories or waxing poetic about the ways we’ve done wrong. We’re just two people who both pulled out of relapses and had to figure out a new “normal” while keeping shit together at work.Things like: How sobriety impacts your career—good and bad, what changes at work events and in friendships, and why relapse is a shitty word that sounds shitty.***If you or someone you know is struggling with addiction or looking for resources to help get sober, aa.org is a place you can visit to learn more about getting support.***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.comVisit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

You don’t need to be more intuitive, you need to stop ignoring the intuition you already have.At least, that’s what Rachael and I uncovered in this episode. We talked about the very real gap that appears between when your gut speaks up and when you actually listen to it.When someone’s tone doesn’t match their words, your nervous system knows before your brain does.***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.comVisit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

In this episode of The Unobstructed Podcast, Rachael and I talk about emotional endurance vs. resilience—and why most people confuse the two.Because they’re definitely not the same.And conflating them is a big part of why burnout sneaks up on so many of us.We chat a lot about how learned helplessness encourages us to tolerate bad conditions instead of navigating to better ones.We also get get into:Learned helplessness and why it isn’t laziness.How to use evidence to challenge your own assumptions.What happens when intuition shows up… and when we ignore itThe difference between emotional endurance and resilience.Embracing conflict and leaning into fear of change.***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.comVisit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

In this episode of The Unobstructed Podcast, Rachael and I traced the root of neurodiverse confidence, and what it looks like when you grow up feeling like the problem.We talk about school, labels, work, parenting, and a lot more. Like the invisible cost of teaching kids to “be good” instead of honest.It starts with a conversation about neurodiversity.Ok, no. Not it doesn’t. It starts off with a conversation about placebo and marketing manipulation—but ADHD took the wheel.And honestly? I’m glad it did.Because wow….I love where this went.***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.comVisit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

In this episode of The Unobstructed Podcast, Rachael and I talk about misaligned expectations. We share personal stories about burnout, being vulnerable with managers, and feeling pressure to say “i’m fine” when you’re not.What starts as a conversation about mental health in the workplace quickly opens into something bigger:The invisible penalties of full honesty at work and why post-COVID “flexibility” was pretty much just an act.The conversation also steers into how childhood anxiety connects to the rise of the attention economy and the myth that addiction is the problem (spoiler: it’s not).Emotional regulation is the survival skill no one taught us. A new class of “mental wealth” is taking shape.***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.comVisit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

In this episode of The Unobstructed Podcast, Derek and Rachael untangle the evolving role of AI in day-to-day work life.AI is changing the way you can do business, but it can't sidestep bad data.***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.comVisit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

What separates those who shape their path and those who wait for direction? Creativity, communication, and self-discovery...agency plays a role in all of it.We get into the "how" of adopting new ideas, embracing technology, and taking ownership of our personal and professional growth.***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.comVisit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

Why is workload visibility is so broken—especially in remote and hybrid work?Things like untracked work and why it leads to burnout, misaligned tools that make work way harder than it needs to be, and task lists beyond what’s assigned—the things that pile in from email and Slack.Work is measured in output, not hours. But if nobody knows what’s actually on your plate, how do you set expectations. And, you know, not drown?***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.comVisit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

The shift to solo work isn’t just about work. It’s changing how we save, invest, and plan for the future.In this conversation, we cover morning routines, hustle culture’s war on mental health, and what happens when employment isn’t connected to retirement planning. And why this leads to fewer workers, fewer retirement plans, and fewer returns—for everyone.So, if AI agents and solo work are the future, how do we make sure financial security isn’t left behind?***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.comVisit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

Let's talk about the importance of creating space get work done (ya know, instead of just talking about doing the work in back-to-back meetings). Derek and Rachael also share openly about navigating workplace conflicts, building psychological safety, and what the real impact of culture does to productivity.As someone with ADHD, Derek has tried a million of those time management “hacks”…and says that, while there’s a lot of fluff, there are actually some ways that do work (no, not just hoping to fit everything in).***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.comVisit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

Who’s responsible for work-life balance—companies or individuals? Derek and Rachael discuss the role of personal boundaries in the workplace, being intentional about taking time off, and the ways routines impact our perception of time.***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.comVisit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

The biggest barriers to growth are the assumptions we don’t question.In this episode, Derek and Rachael chat about how vulnerability enhances leadership. We also dive into the dynamics of managing up, the nuances of adult learning theory, and the significance of understanding the "why" behind a person's actions in the workplace.***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.comVisit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe

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.comVisit Rachael’s website: rachaelsink.com Get full access to Unobstructed at explore.theunobstructed.com/subscribe