That’s something that’s stuck with me over the years. And since gratitude is a muscle that needs regular exercise like any other, finding an excuse to celebrate something is decidedly good for your health.

So if you, like me, need that reminder from time to time, let this be it.

If you missed it, here’s the last one.

What’s happening?

June 2026 edition:

1. A cause for celebration.

2. The latest from Unobstructed.

3. MAP Year Project updates.

1. A cause for celebration.

June is LGBTQ+ Pride Month and Men’s Mental Health Awareness Month!

In the spirit of renowned philosopher, Garth Algar, and his famous words, “Party on, Wayne,” here’s a mix of favorites—new and old—from Unobstructed in celebration of both Pride and Men’s Mental Health!

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2. The latest from Unobstructed.

From Kickturn, a daily column on pivots and new perspectives:

“Damage Control”

Brakes! The brakes!! HIT THE BRAKES!

I’m sitting in a general store in small-town Vermont today, eating lunch and taking in the stillness. There’s a few other people in the log-cabin-like building, but everyone’s moving slow. Calm. The vibe here is “unhurried.”

Not mine; not when I’d first walked in, anyway.

Keep reading.

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From Unobstructed Weekly, the flagship column on finding clarity:

"Please Make Time For Keith And Charlie"

For years, I felt like I was surrounded by people who didn’t want the same kind of life that I did. Folks in my hometown seemed to spend each day commuting to an office job in rush-hour traffic only to then hustle home and hurry off to [insert kid’s extracurricular sport or activity here]. Mornings were a mad-dash-frenzy of trying to catch the bus to go do it all again. Weekends were for yard work and living out blue-collar fantasies through home-improvement projects.

Everyone seemed happy to keep repeating the cycle.

I didn’t get it.

Keep reading.

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From Breaking Trail, a monthly column on trying new things:

"Another Level To Explore"

10,000 hours; that’s the benchmark that has entered the cultural zeitgeist from Malcom Gladwell’s seminal work, Outliers. Hell, it even made it into a Macklemore song literally called Ten Thousand Hours. Yet, we all are shown “experts” constantly in a myriad of forms — from professional career coaches to influencers with TikTok crafting tips. Are these people actually experts? Why am I never watching people in progress?

Keep reading.

3. Updates from The MAP Year Project.

Each night, I sit down to write my daily column after working on other stuff all day. Recently, I went through my writing from the past 10 months of The MAP Year Project to help organize things as I move toward manuscript editing.

From my spot at the dining room table, I scrolled to the top of the doc I’d been working in and I felt my eyebrows climb up my forehead. My head shook back and forth and, before I knew it, I was smiling and nodding in disbelief.

• 158,457 words so far.

• 303 days in a row.

• Two months left.

You can learn more about The MAP Year Project, and how to follow along, here.

An attitude of gratitude.

If you’re reading this, I want you know just how grateful I am.

Seriously, it means a lot.

I appreciate you.

onward.

Subscribe now

Thinking about my thinking is something I’ve done since I was little. Plenty of us do, to some extent, and it’s unfortunately easy for that to keep us from showing up and sharing ourselves fully. We are the stories we tell ourselves, after all... So, throughout the month of May, we uncovered a bunch of ways of reframing those stories and surfacing ways to feel less stuck.

If you missed it, here's April's recap.

What’s happening?

May 2026 edition:

1. Return of the pod.

2. The latest from Unobstructed.

3. Friendly reminder: composure ≠ currency.

1. Return of the pod.

Caleb and I have been having a blast working on new episodes of The Unobstructed Podcast. We’ve got some fun ones coming up this month, including guest appearances that we’re downright stoked about.

Here’s a quick teaser.

2. The latest from Unobstructed.

From Kickturn, a daily column on pivots and new perspectives:

“With No Ulterior Motive”

Being the last person standing is not the only strategy for becoming successful, but it certainly has a high hit-rate.

Keep reading.

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From Unobstructed Weekly, the flagship column on finding clarity:

“Retracing Your Steps In The Alpenglow”

There’s a gap between what we notice and what we share, and I never felt like I was very good at sharing in ways that other people understood.

Maybe I played too much Mario Party as a kid, but I always thought about it like trying to find a trap-door. I’ve spent the better part of 15 years mulling that over while watching sunsets by this lake.

And I finally found a trap-door.

Keep reading.

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From Breaking Trail, a monthly column on trying new things:

“Comfort In Consistency”

The two hardest things I’ve done so far in this life were both lessons in consistency:

1. Thru-hiking

2. Parenting.

They are also strikingly similar.

Keep reading.

Even more to explore:

3. Friendly reminder: composure ≠ currency.

My episode of Stories From The Stage recently aired on national TV!

I told the story of a lesson I learned from my grandfather about keeping your composure, and was totally unprepared for how much it would resonate with people.

Showing up and sharing yourself can be scary, especially when you’re worried about pushing through that fear and ending up feeling misunderstood. But... if you don’t show up at all, you’ll end up feeling misunderstood anyway.

So, you might as well try.

Besides, what if it all works out?

onward.

Subscribe now

In the modern era, that used to look like quick accompaniments to longer-form newspapers. And, in the advent of all things digital, that originally meant emails that linked out to longer, web-based content.

Recently, I realized I’d been accidentally muddying things. Plenty of other folks are doing that, too... calling things newsletters that aren’t. And while that doesn’t make it better, it does help me understand why it happened.

What’s happening?

April 2026 edition:

1. An update on this newsletter.

2. The latest from Unobstructed.

3. Welcoming a new monthly columnist.

4. Announcing The Unobstructed Podcast 2.0

5. Sharing the process instead of just the product.

1. First and foremost, an update on this “newsletter.”

Over the past two years, the weekly newsletter I publish went from sharing stuff I found interesting in the mental health and wellbeing space to something... well, completely different.

Whoops.

At first, it began shape-shifting slowly. Then, things kind of compounded pretty rapidly. Originally, I’d write a couple of blogs per month and post them on my website. It was a project I thought would help me reclaim my writing voice. I’d then send out a monthly email with a short recap and some links for those who were interested in reading more.

You know... like a newsletter.

After a while, I began writing quite a bit more than two blogs per month, though. Truthfully, I think it happened when I made the jump from Mailchimp to Substack. While I was just looking for an easier way to automate and manage things, I think the cultural influence of the platform played a role in morphing my once newsletter into long-form essays, delivered via email.

Look, I like writing. A lot. I’m glad those dominos fell how they did. And, at the same time, inbox oversaturation is no fun—I’m a subscriber who reads stuff from plenty of writers I like, too.

So, when it comes to Unobstructed, I want to take a second and clarify a couple things.

1. Unobstructed is a multimedia publication made up of several different columns. You can think of it (structurally at least) like The Atlantic, Granta, The New York Times etc...

2. I’ve re-organized Unobstructed such that you can simply opt-in to the stuff you want to receive, at the pace you want to receive it. For example, you might want to receive all the long-form content we publish via email directly... or, maybe you only want an occasional recap.

With that in mind, I’ve decided to reintroduce a real newsletter, in the truest sense of the word: this one... The Unobstructed Monthly Dispatch.

It’s a monthly newsletter, from me, Derek, that recaps the latest goings-on and links out to the recently published longer-form, web-based stuff from Unobstructed.

Columns within this publication include:

• Kickturn — a daily column.

• Unobstructed — a weekly column.

• The Unobstructed Podcast — monthly conversations.

• NEW: Breaking Trail — a monthly column on trying new things.

• NEW: The Monthly Dispatch — this thing you’re reading right now.

And, since you’re reading this, you are already subscribed to The Monthly Dispatch. But if that’s *not* something you’re interested in, you can update your subscription preferences here.

2. The latest from Unobstructed.

From Kickturn, the daily column:

Out Of A Fog And Into Focus

Following autopilot.

I hadn’t planned on sitting down at my typewriter. When I walked into my office, I set down my coffee like I was about to sit at my computer, but then just... didn’t?

Keep reading.

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From Unobstructed, the flagship weekly column:

Willpower Is A Scam

On rigging the odds in your favor.

For the past few years, I’ve dreamt of finally getting back in shape. Winning the never ending game of tug-of-war by visualizing the type of person who can do it and just… willing myself to do what they’d do.

The want was there, I just couldn’t find my way to the actions that would actually make those things, ya know, real. Until now.

Keep reading.

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From The Unobstructed Podcast:

Rediscovering Analog Joy

Resurrecting your low-tech childhood hobbies with Caleb Walker.

It feels like there’s this widespread expectation to be available all the time, and not just at work. I’ve noticed that when people text me, it feels like they’re awaiting an immediate response. Consciously or not, that’s how my brain seems to react to new texts, emails, and messages now. You know what I mean?

Keep reading.

3. Welcoming a new monthly columnist.

I’m excited to officially welcome Caleb Walker to the Unobstructed team!

Caleb’s taking on a new monthly column, called Breaking Trail, where he’ll be sharing essays on venturing into the unknown and using agency to test what’s possible. His first edition of Breaking Trail comes out this Sunday April 5th.

4. An announcement about The Unobstructed Podcast.

At the beginning of 2025, Rachael Sink and I started a podcast... and it became a top 10% most shared show on Spotify in its first year!!!

While you’ll still hear from Rachael on some episodes going forward, she’s decided to step back a bit so she can give herself more fully to other parts of her life. So, in addition to writing his new monthly column for the publication, we’re excited to share that Caleb Walker’s also stepping in as the new co-host of The Unobstructed Podcast!

You’ve likely had the chance to get to know him through his multiple guest appearances, but be sure to tune in to the next episode so we can properly welcome him aboard.

I also want to thank everyone who’s listened and supported our journey so far. We’re so excited to see what year two has in store for us—especially with Caleb joining the crew!

5. Sharing the process AND the product.

I’ve been trying to be better about sharing both the process and the product, rather than just the product. So, going forward, my hope is that this monthly dispatch will help me do that.

I’m really glad you’re here and I’m psyched for what’s ahead!

Happy April.

onward.

Subscribe now