What is it about me that keeps people at a distance?

Any guesses where this photo was taken?

There's this video that's been in my "watch later" queue on YouTube for... I don't even know how lon...

It's summer here in New England, which means longer days and (hopefully) more leisure.

That hollow, echoey, slapping noise sounded very much like a bone breaking.

Avoiding grief only makes things worse.

We took an excel class in sixth grade and I had no idea it'd be such a big part of my adult life.

Today was a build day for me.

Ever catch yourself after saying something and think "Wait; who was that? Did... did I just... is th...

In less than a second, all the confidence I had vanished.

I'm not convinced that my default level of self-awareness is a good thing. I get in my own head a lo...

I recently read a quick, update-style piece from Maggie Rogers and it got me thinking about accessib...

“I’m sick of following my dreams. I’m just going to ask them where they’re going and hook up with th...

I will not absorb the responsibility of regulating other people on their behalf.

We were the last house before the cul de sac and our yard was part of its perimeter.

Ok, interesting...

"If you could've been born with elite-level proficiency in one skill, what would you have wanted it ...

On any given day, I’m caught somewhere between wanting to take a trip with no return ticket and want...

Sometimes people articulate my own ideas much better than I'm able to.

Well, I'll be damned—they changed it.

With a huge exhale, I dare a glance at the timestamp.

One year ago today, after tearing apart and rebuilding one of my websites, I published a piece about...

Well that's... odd.

I'm blinking through a bleary fog that won't clear.

I grew up believing that I had to come up with a really, really great idea and then protect it like ...

This hill's 1,000 feet and I'm at the bottom of it, making my way back up after reaching the midway ...

My eyes are unfocused, staring out the window at... I don’t know what.

Ava woke me up this morning with an unassuming nudge. That's not the abnormal part, though.

I'm sitting by the back windows as the storm clouds roll in.

Aaaaaand we’re back!

"Yeah, I don't know... I try not to think about it."

When Isobel asked if I wanted to bike down to the water to watch the sunset, I hesitated. Doing some...

Sure, I'd been nervous... but this is happening.

BURLINGTON, Vt., July 5 — After seven years on the run, one very sweaty and disheveled man on a moun...

My eyes are closed but I can still see the sun.

We're heading back from the lake; walking through the woods in the dark.

I keep meaning to put some music on, but I've been wearing my headphones in silence for ages.

It's going better than expected.

Since I've been trying to be better about sharing the process instead of just the product, here's my...

I'm watching Hidden Figures and I can't shake the skin-crawly feeling on the back of my neck. There ...

You find what you look for.

Sometimes it feels like I've been living out of a suitcase for my entire life.

The mental gymnastics of modern self-help truly baffle me.

I'm outside, tucked under a canopy of trees, sitting along the river by the bridge.

It’s dark but not black.

Why did the gamer take a ladder to school?

I'm watching Noah Kahan's new documentary, Out of Body, and it feels like I just got slapped in the ...

Figures, the parking lot's full.

Brakes! The brakes!! HIT THE BRAKES!

I don't want to talk about AI anymore.

Ducks in a row are not the same as ducks on the go.

There’s a dad with two young daughters at a table nearby and when he bends down to help retrieve a d...

I'm searching for something to watch and it's making me more and more frustrated.

The flustered flapping of feathers catches me off guard.

I'm walking around the block this morning, testing my sprained ankle that I just freshly reaggravate...

Henrik Karlsson writes stuff that makes me start speculating wildly about "what if?"

I was an avid reader when I was a kid, and I can pinpoint the exact moment when that stopped being t...

It's always the palette cleanser that does it.

Photo of Derek MacDonald and the 2026 HOBY junior staff team by Andres Tejeda.

I shouldn't have come here.

I'm sweating profusely; let's... um, ok how about we just leave it at that?

I went running today but I probably shouldn't have.

Last night Isobel and I were talking about my comfort with public speaking.

The table I like was open, so I snagged it.

I did not have “hibachi chicken” or the memories tied to it on my bingo card for today.

It's not often that I get stage fright.

The expression across from me looks hurt more than frustrated.

I'm traveling for a conference this week and it almost ruined my daily writing streak.

Delayed gratification is cool and it's not that hard to pull off.

I thought it might be sore but I didn't expect it to hurt.

I don't know why I never thought of it like that.

Since I've been trying to be better about sharing the process instead of just the product, here's my...

I've been feeling like a shitty friend lately.

Trying to stay in-the-loop perpetually leaves me feeling exhausted and worse off.

Today, I'm celebrating 5 years of sobriety.

It's nearing the end of the work day and I'm in my kitchen.

If you've ever asked yourself "why—WHY—did I say that??" after an especially awkward interaction, co...

Ever heard of the meditation app Headspace?

Being the last person standing is not the only strategy for becoming successful, but it certainly ha...

Lately, I’m seeing a lot of cultural commentary about how things like "taste" and "discernment" have...

Sometimes, relatability's the best medicine.

I live near a lake that seems to have all the answers.

I'm so glad Isobel and I decided to come home last night instead of staying, and camping, like we'd ...

Today's day 265 of this year-long challenge.

One of my favorite things to do is to try and notice the things that other people notice.

For someone so highly attuned to the people and places around him, there's one area of social discou...

I know the question's coming and I'm braced for impact.

I'm running by the water just absolutely drenched with sweat, head-to-toe. Sorry. There's really no ...

I got dressed to go running today, but never went.

Maybe it won’t look catastrophic from the outside. You might not even see it coming, either, but the...

Ok, but what if it works out?

It's five past eight, I'm late, and I don't even want to go, anyway.

I'm rounding the corner on my bike and looking over my shoulder in the opposite direction. No cars i...

You know, how certain smells remind you of a distinct memory of your grandmother? Or, how a certain ...

I was dripping sweat, but refusing to slow down.

This angry voice was the same one from before, so what happened?

I'm about to head to the register when I double-back.

One day you’re going about your daily life, just as you normally do, when, seemingly out of nowhere,...

I'm zoning out with the water running.

Instinctively, I start turning the volume down immediately.

I feel smoke rising from my ears.

Why did the metronome get promoted?

I got a new basketball, but I hadn't played since I was a kid.

I hadn't realized I was stuck until I found myself scrolling on Substack.

Thunder boomed and lightning struck.

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.

Newsletters were intended to be roundups; short-form updates about the goings-on.

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.

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.

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

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.