Unobstructed

I'm on my fake, morning commute as a remote worker (aka a walk around the block) when the podcast I'...

I'm thinking about whether or not balance is actually achievable while sitting at my analog desk.

I'm waiting patiently to pay for my coffee while the cashier's chatting with the guy in front of me.

I'm walking through the grocery store and I hear "dad, you gotta use your brain here."

Today's not off to a great start, so I skip my morning pages and try something different.

I was sitting in a local cafe and found myself tearing up.

When the timer went off, I couldn't resist saying "pencils down."

I'm fairly certain my neighbor's not a lunatic. And if they are, perhaps they're benign enough...

We teach boys to hide their shame, and then wonder why men struggle with loneliness.

I'm just focused on getting us there in time for sunset.

This is a pretty inconvenient intersection and the light just turned red.

It makes sense in my mind but... now I need to figure out how to explain it.

I could feel it when I opened the door.

I used to jump off these cliffs and into the water 60 feet below.

I’m watching myself perform on national television... this is WILD.

I'm going to tell you a secret.

We desperately need role models of healthy, secure masculinity. I can’t believe it’s controversial t...

I'm writing an email to a friend when I start to wonder if I actually sound like myself.

The sun finally shows up in full force, and I've been couch-bound for two days now.

Yesterday I encountered a river otter while running by the lake.

I'm eating lunch today when I get a taste of my own medicine.

Apparently, most people don’t think about their thinking quite like this.

You know that feeling where it seems like the world values something completely different than you d...

It was the sticker by the register that got me.

Today I turned 32 and I never expected to make it this far.

I'm staring intently at the lead guitarist. At least, at first.

Before I know it, I'm parsing 25 years worth of memories to find an answer.

I'm sitting in my reading chair by the window, evening light traipsing across the glass and then spi...

The sun's finally out.

I sat down to write this and couldn't.

I didn't want to believe it.

Hey, I’m Caleb. Welcome to my new column, Breaking Trail.

One of my favorite quotes comes from a movie it wasn't even supposed to be in.

I hadn't planned on staying up so late.

The notification said I'd been tagged in a post, which was intriguing at first.

I hadn't planned on sitting down at my typewriter.

I recently started posting a monthly "what I'm up to" blurb on my personal website.

I can't stop thinking about something I read yesterday.

Halfway through today's run, I got an idea.

The sun on my face felt fantastic, even with the swarm of people enveloping us.

As I climbed into my truck, I reached for the seatbelt and wondered if maybe I should've gotten up a...

While plodding along on my run, I clocked the dog up ahead.

I'd been pacing through the living room of the Airbnb until a voice cut me off.

For the past few years, I’ve dreamt of finally getting back in shape. Winning the never ending game ...

Over the speakers, I heard my name get called to go on stage.

"I can't do this anymore."

Wherever you go, there you are.

I used to carry a fake ID in my wallet.

There's a drill we used to do in high school football that I only now realize applies to life.

When I started my daily column, it was a course-correction and I didn't fully understand the downstr...

Right there in the middle of the coffee shop, my mouth actually fell open.

I didn't have time to write a story today, so I wrote an insight instead.

6am, my alarm goes off and I hit snooze. Suddenly, it's 7am.

Today's one of those days that isn't necessarily good or bad, but feels like something's just not qu...

On my run today, I realized something about the state of humanity.

Consuming art is one thing, digesting it is another. Creating depends on both, and all of that requi...

I hadn't expected a stranger to make me reconsider how we put ourselves back together.

Today's Isobel and my anniversary, so we got coffee at the place where we (accidentally) first met.

Today, I was proven right.

Every year around this time, I face a serious moment of reckoning.

Today I made myself a new bookmark.

This morning started with a flashback, and not a good one.

My health wasn't all that suffered from my multi-year career sprint.

On this day two years ago, I published my first newsletter and it caused my life to start shifting.

When I was a teenager working as a camp counselor, the parent of one of my campers once told me how ...

You give hope a chance the moment you admit why you’re scared.

In 2017, I was at a trade show with some of the world's top outdoor athletes.

I'd been focused on not wiping out.

I’m rewatching the Ted Lasso series right now, and it got me thinking about recognition and response...

I've tried a lot of morning routine variations, and my biggest hurdle has always been fitting in all...

How people respond tells you a lot about what they've been through.

Believe it or not, we're half-way there.

Someone recommended a book to me today because, in their words, it was similar to my writing style.

I listen to a lot of podcasts, but I hadn't expected an interview with a comedian to change how I se...

"Clear is kind. Unclear is unkind."

Days like this make it hard to write.

The price of existing is going up and I’m not convinced keeping up is worth it.

We had a handheld label maker when I was a kid that stressed me out a ton.

You know when you can feel yourself grinning like an idiot?

I saw myself in someone at a coffee shop today and I hated it.

Today, I crashed a zoom call by accident.

The price of existing is going up and I don't know what to do about it.

When I was 16, I fired my driving instructor before testing for my license.

Years ago, I gave an unorthodox talk to an auditorium full of high school students.

Photo of Derek MacDonald by Steve Gregory

Whatever I was expecting, it wasn't that.

"Ready, set, GO!"

I tried something different and now I don't think I'll do it any other way.

Pen held firmly between my fingers, but suspended loosely in mid-air, I noticed in real-time how muc...

Yesterday, I did something I don't normally do after someone commented on an essay I wrote...

Ok, fine—most of the time I'm not excited about catching up on email.

As a writer I've never really dealt with writer's block in the way I've seen it described by others.

When I looked up, I was surprised to see the crowd had disappeared entirely.

The snow was starting to pick up. Wind, too.

Ski lodges have such a distinct smell.

Most days I wake up in a fog of confusion, but not today.

It was late, but my brain would simply not wind down for bed.

The sun was setting but I barely noticed the light being siphoned from the walls.

Last night, Isobel came over and sat down next to me on the couch. I pushed my laptop aside and she ...

You know when someone does something that immediately makes you feel stupid for not thinking of it? ...

A friend and I'd gotten together for coffee this morning, as we sometimes do, but it devolved into s...

Sitting in my chair by the window this morning, I put down my book and looked up. Tilting my head an...

I usually make coffee first thing in the morning. The caffeine's great but, honestly, I do it for th...

Lately, my mind's felt a bit like a tangled pair of headphones, and I've been thinking a lot about t...

I noticed two interesting things when reading this morning.

The Unobstructed Podcast: Episode 33 This episode of The Unobstructed Podcast is about rediscovering...

As I walked into the kitchen this morning to make coffee, I spotted my neighbor in their driveway.

On the scariest drive I’ve ever done, I'd been pulling a U-hual trailer through a mountain pass duri...

I grew up in the aftermath of 9/11. As an American, I watched on TV as men marched through the stree...

This morning I could see the cold before I could feel it. Outside, the air was dull but the trees we...

Let me ask you something. Think of your favorite movie for a second... once you've got it, I want yo...

I was scrolling and had to laugh at the contrast of what I saw.

When we first started dating, my partner mentioned I'd seemed unenthused at times or that I didn't h...

I stared at my phone completely dumbfounded last night while getting ready for bed.

On any given day, I’m somewhere between deleting myself from the internet and knowing that I’ll show...

Today I did two things I never really do anymore. One kind of led to the other. I don't know what ma...

I'm proud of myself. That's not something I say very often. In fact, I couldn't remember the last ti...

I've been thinking a lot about how people used to tell stories and how that's changed. How all of us...

Every day, I start my morning pages the same way.

Some days, you discover you're still cradling a coffee mug that's gone cold.

Chicken fried rice has such a consistent, distinct smell—for the most part. That peppery, garlicky, ...

Daylight soaked through the window by my shoulder. With a book laying open in my lap, I looked up to...

Other than the podcast I was listening to, the only sound I heard came from tires sloshing through t...

I used to dream of hitting a big, fat pause button that could stop time. Those dreams offered little...

Today while food shopping, I watched as someone got into position and blocked the doorway.

Last night I logged into Instagram and had an identity crisis.

After recovering from a mental health crisis about 10 years ago, running became a staple in how I le...

The past few days have been downright frigid. Single digits, windy, snowy, blustery—all of it.

When I started writing this daily email series, I hoped it would make me a better writer and communi...

On the TV screen, I watched as one person after another grappled with what to say.

On the other end of the phone, my mom was aghast. "You sound terrible" she'd said. Laying on the cou...

It's cold outside; snowing, even. According to the thermostat on the wall, my spot on the couch is w...

On the TV screen, I watched as one person after another grappled with what to say.

Last night, a couple hundred of us held our collective breath while staring at someone in a dimly li...

Everything's either covered in black ice or white salt residue. Today I watched a postal worker wipe...

All I know is that I see things differently. I have my whole life, but I've finally learned how to s...

This morning was full of rain, but yesterday was frigid. Which means every square-inch of ground out...

Almost 10 years ago, I woke up at 4am on Christmas morning to hike up a mountain in the dark. I stop...

Last night was cold and dark; fitting for the end of December. Outside, the wind was howling—streaki...

This week every year, like clockwork, I get sick.

It's been snowing for days at this point. A soft, knee-deep blanket of the stuff means it comes all ...

I used to worry about which parts of myself to share. The whole thing felt risky.

'Twas the night before Christmas—and I, myself, lost in thought—pondered writing a poem, but then op...

When I was a kid, a barred owl lived in the tree outside of my bedroom window. Until one day, it van...

Something about seeing a collection of letters all jumbled together makes me want to solve the puzzl...

Fear of letting people down is a hell of a way to move through the world. While drinking my morning ...

I keep learning new versions of acceptance.

I made an absolute mess and it made things so much more clear.

It's nice to know that real people and real writing can still fuck you up.

I used to do the post-it notes thing but it always messed me up.

There was a chapter of my life where kids running around would've made me angry. Even though they we...

I daydream about what it'd be like to freeze time.

I still remember the look on his face when I’d said, “Alright, give it a shot.”

Convincing others to see the world as you do is a great way to ensure they won’t. And it’ll drive yo...

I froze when I'd heard it. It'd been a total fluke—I hadn't meant to eavesdrop. Still, out of nowher...

I'm becoming more and more aware of the difference between creation and commentary. Maybe that's som...

It'd been my fault. That much was clear. I remember feeling angry and upset. Then, just... sad.

Years ago during a mountain-guiding clinic, I learned a lesson on throttling my potential I'll never...

Mean it like you say it... that just sounds better to me. Say it like you mean it always felt like d...

I've been thinking about how knowing stuff and putting it into practice are two different things—thr...

Your whole direction in life can change in a single week, if you let it.

Cold, dark mornings make me feel the most like myself. Yes, I realize that could use a bit of clarif...

Getting a pocket notebook and a pen was the second-best thing I ever did for my ADHD… the first was ...

At the doctor's yesterday, he'd looked at me with inquisitive eyes when I floated a pretty big thoug...

Today, I sat at my desk in disbelief. With the wind howling and snow spraying across the windows of ...

I've noticed a shift happening in how we communicate. All of us. I don't fully know what that means ...

I don't know what it is about falling snowflakes that makes silence sound so good, but it's always b...

The first time I called 911 I could barely speak.

I took this photo on a day when, like today, life seemed to snap into focus. I’d been tired a lot ba...

It wasn't even light out yet, but somehow we'd fully opened this can of worms. In a rare role revers...

Let me say up front that this feels silly, but I'm doing it anyway... giving myself a performance re...

I've gone back and forth with how I feel about novelty. Variety can be a good thing when it's an add...

I don't particularly like Thanksgiving. It's not so much that I dislike it, it's that it just always...

The Unobstructed Podcast: Episode 32 This episode of The Unobstructed Podcast is about getting out o...

Today, while sitting in a coffee shop with rain splattering the windows, I thought back on this past...

I'm tired, but invigorated, by a string of life-shifts lately. So today, I'm switching things up.

Things feel lighter today than they have in a while. My mom and I were sitting in my living room, ca...

All I could think about was acceptance while driving home from a Friendsgiving weekend in Massachuse...

Avoidance caught up with me today, but not quite how I'd expected.

Something's changing. I don't fully know what it is yet but maybe that's my problem; always trying t...

I'm usually very aware of my surroundings, but I'm not even sure if that's helpful anymore.

81 days in a row of writing these (126 including the pre-MAP Year test phase) and I almost skipped t...

I think my life is just a growth spiral. It wasn't always, but it is now. I'm moving forward, while ...

Something you should know about me is that I wasn't always like this.

Choice of perspective. That's what I'm thinking about today.

I used to move through life like a rubber band wrapped around a watermelon. I don’t know if you’ve e...

All I could think about was acceptance while driving home from Friendsgiving weekend in Massachusett...

The start and stop of the sink was nothing compared to the clinking and clanking of the dishes. I'd ...

It's not like I needed a reminder. I was well aware I'd been spreading myself thin again. That reali...

Today marks a whole month without the Substack app. In its absence, one thing has become supremely c...

I wrote my morning pages on my typewriter for the first (and maybe last) time. I've been typing shor...

I'd felt it as soon as I woke up. The snow outside made things warm and cozy rather than dark and dr...

It snowed the first real snow of the season today. There's been spits and spurts, but today it's rig...

It was my English teachers who pushed me to think critically.

You don't realize how much your environment influences you until it changes. Mine's shifting pretty ...

I'm a tangled ball of tension today with nowhere to let it come undone. My nervous system is fried. ...