Unobstructed

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 got to share my story on national TV.

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. ...

I keep seeing blue and white VW buses. Over the summer I'd been stuck enough to ask the universe for...

Waiting for the red light of the live video-feed, all I could think of was the intro to The Christma...

I've started to realize the medium matters more than words ever will. I find it both frustrating and...

They're probably thinking "he looks ridiculous! What's he doing anyway?"

I'm tired. Writing and publishing daily is hard. I love it, but that doesn't mean it's always shiny ...

Mick Jagger sees a red door and wants to paint it black. Don’t we all, though?

Things rarely fall into place, but they always come together.

It looked like someone took the world's largest can opener to the top of the truck. I hadn't seen th...

Asking "why" is so important. I see it as the most pivotal piece of our evolutionary puzzle.

I don't know why I'm suddenly resisting innovation. For most of my life, I've been driving it. My fi...

It was an accident. Ok—no it wasn't. But it's not like I went looking for it. It just sort of... hap...

On days when you can't do a lot, try for a little.

I'm listening to a podcast, but all I can think of are Henry David Thoreau's words from Walden, "I w...

My whole life has been shaped by rapid tech innovation. That’s the blessing and the curse of being a...

I don't know when playing got so hard. It didn't used to require so much thinking... and, if anythin...

I've been playing chicken with the line between creating and critiquing for as long as I can remembe...

Before deleting the Substack app, I worried about not finding new stuff to read, but then I realized...

I used to be part of multiple friend groups, but not anymore... not really.

Wipers whipping, rain hammering the windshield, and I'm dumbfounded. Then, I'm both impressed and mi...

The Unobstructed Podcast: Episode 31 This episode of The Unobstructed Podcast is about trade-offs.

Sometimes acceptance looks like inaction, but requires motion.

Mick Jagger sees a red door and wants to paint it black. Don't we all, though?

My whole life has been shaped around tech advancements. That's the blessing and the curse of being a...

"Hey Derek—the usual?", she asked with a smile I wasn't expecting. It's been a long time since someo...

I hate to say it, but I think I need to delete the Substack app.

Today was a "holy shit" moment for me: this has been an 18-month writing journey of nearly 400,000 w...

"Just because your gut told you something was wrong doesn't mean you have to figure out why."

The creator economy is the new “pull yourself up by your bootstraps” fallacy. Isobel’s boiling water...

Finding your rhythm requires some blues. Today was a good day, but I've been in a rut lately.

Productivity feels a bit like pushing peas around on your plate. You might be making space, or just ...

Within six months, he'd have a heart attack at 24 years old.

My relationship with control and capability is a work in progress. As you might know, the idea is to...

I woke up rested, which never happens. I think I forgot what it felt like?

Good things happen to those who participate. But I'd planned on being a spectator, not a participant...

My 93-year-old neighbor forgot, so I let him.

"You looked so locked-in, and we could only see half of your face, so... we weren't sure if it was y...

Do you ever feel like you're trying and failing to resume your normal life after coming back from tr...

Turns out my doctor’s a real person. I spotted him at a local coffee shop today. As in, somewhere ot...

I want to be someone who engages effortlessly online, but I'm not. Maybe you relate?

Productivity for the sake of productivity is dumb, but so is performing your indifference by doing n...

I'm ready to knock something down, but sad to see it go.

Maybe art helps people heal because there’s no right answer.

I finished a book yesterday and I'm pretty mad about it. Not at the book (it was great) but at mysel...

There are two things you should know about getting shit done. I learned about them both as an outdoo...

Thanks for your dedication to finding a way through the shit pits.

Today, for the first time in about six years, I turned on my DSLR camera. I found one of the last ph...

Fear of being "too much" will make you miserable.

Unexpected validation hits different. I don't usually anticipate affirmation in my inbox. But that's...

There's this memory I can't stop thinking about from when I was 13. Laptop in hand, I was sitting in...