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.

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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

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.

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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

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.

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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

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.

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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

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).

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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

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.

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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

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.

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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

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.

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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

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.

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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.

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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

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.

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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.

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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