Unobstructed

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...

It’s the beginning of January and I’m sitting on the edge of my bed, staring down at the phone in my...

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. Isobel recently b...

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...

I'm all for simple structure, so long as following it doesn't slow things down.

Bringing my laptop to a bonfire was unexpected. If it sounds unusual, rest assured it feels that way...

I'm sitting at a picnic table next to the ocean. It should be serene. And it is—just not like I'd fi...

I was drinking my coffee by the water this morning. Rocky, coastal shoreline and sun draped across m...

One of my favorite sayings is "everything in moderation, including moderation."

Superhero stories might create aspiration, but humanness creates connection.

Today is day 17 of The MAP Year Project and it's already helped me realize something I hadn't expect...

Formatting is how we know what we're looking at.

I can't pinpoint exactly when, but something in me snapped. It just kind of... broke. And then it be...

At first, my writing might look like self-righteous navel-gazing. I can see why, but that term has n...

I was in line for coffee today when the guy behind the counter got everyone's attention without rais...

I've found one thing consistently changes a shitty situation to a less shitty one. Often, it even sn...

Being okay with restarting your streak at zero is one of the best “growth hacks” of all time. And if...

When I think of endurance, three things come to mind.

Actually doing what you don't want to depends on how you punish and reward yourself. Best-selling au...

I've found that hyper-focusing on the distance between you and your goal only brews resentment and f...

Men don’t know when to quit because they’re told not to.

Sitting by the window, morning rain splattering the glass, I'm thinking a lot about self-doubt. This...

I was thinking back on the week while sitting at my desk this morning. It was still dark out and I w...

I was at my favorite coffee shop today. Sitting at a table by the back wall, I let my mind race. It'...

The Unobstructed Podcast: Episode 30 For as much mental clarity as running gives me, I hadn’t felt d...

Today's an off day for me. I know that's probably not what I'm supposed to say on Day 2 of The MAP Y...

Today's the day! We're officially kicking off The MAP Year Project. Today's post is slightly differe...

Daydreaming about a new life helps make our real one bearable, until it doesn’t. We dream of freedom...

On a walk this morning, I was reminded of the difference between decay and diminishing returns.

I hadn't expected to get hit with such a good reminder this morning. I was catching up on emails whi...

We dream about having more creative freedom. So we keep saying we’ll get to that passion project, bu...

The Unobstructed Podcast: Episode 29 Social media went from shooting the shit online to framing it a...

I was sitting in a local cafe near the window, minding my own business. It was mid-afternoon. Scribb...

Lately I’ve been thinking about how writing online has changed. Not just what gets shared, but how e...

I don’t care how easy social media makes it to keep in touch. A few years ago, I wanted to delete it...

The second arrow theory is a Buddhist concept that describes how we often suffer twice from the same...

Let me see if I have this right— All things analog are on the rise. But AI is making roles redundant...

Lately I’ve felt like my writing is getting better. It's been about a year and a half since I made t...

Landing pages are finicky. I was fine-tuning one for MAP Year Project signups today and hit a snag.

The Unobstructed Podcast: Episode 28 In this episode of The Unobstructed Podcast, Rachael and I have...

Puzzle pieces complete a picture but legos create one. I like to solve puzzles, but build with legos...

Some days I wonder if it'd be easier to quit the internet and just sell physical products in a local...

Six years ago, a traumatic brain injury from a snowboard accident forced me to completely reevaluate...

Instead of “so… what’s new?” or “what’ve you been up to?”, lately I’ve been asking “what are you mos...

If you’re constantly recalibrating, when are you creating? Living a life beyond productivity hacks s...

"Please welcome our next storyteller to the stage—Derek MacDonald!"

The Unobstructed Podcast: Episode 27 Taking Up Space Without Apologizing For Existing by Derek MacDo...

Adding the final touches before kicking off a new chapter.

Perfectionism is poison to your dreams.

The morning air was already thick, promising another hot summer day in Vermont—even though it wasn’t...

There's a hummingbird that stops by in the mornings to check on the flowers.

I slowed to a stop before turning right, driving along the riverside toward the highway. It was mid-...

Some days unfold, others unravel. I wasn't sure which this one would be.

The Unobstructed Podcast: Episode 26 When You're Having An Off Day, Take The Day Off by Derek MacDon...

I was sitting at a table by the window.

I was sitting at my kitchen counter this morning. Like most Mondays, I’d scanned my inbox with a cup...

It feels harder than ever to be seen for who you are.

6 months ago, I started a podcast. Today it crossed 5k downloads.

Over the last year and a half, I've settled into the rhythm of creating, editing, and publishing my ...

Sometimes I wish I was one of those people who didn’t give a shit. Life would be easier. But nope, I...

The Unobstructed Podcast: Episode 25 The Alpha Male Antidote by Derek MacDonald Visible vulnerabilit...

Curiosity helps you think about where you might be right or wrong about people.

It's always worth asking “what is this instead of?” or “ what is this in addition to?”

Imitation is a form of mental magic—you pretend to be the thing you want to become, then you do.

Creative journeys are a slog. When people say following your dreams can be hard, they’re actually sa...

When I was coaching competitive snowboarding, I used to say: “if you’re not having fun, you’re doing...

The Unobstructed Podcast: Episode 24

I was sitting with my partner, Isobel, this afternoon in the screened-in porch of the fenced-in back...

If you only ever try to fix what you’re bad at, you might get better over time… but when you focus o...

The problem with shielding yourself is that you trap your pain inside, with no way out. I’m grateful...

Friendly reminder, the people who say that learning is another way to procrastinate have already rea...

Since I run a weekly newsletter where I publish essays and podcast episodes, I wanted to find a way ...

Daily Emails From The Journey Writing full-time, sharing how I use tech to make space for creativity...

The Unobstructed Podcast: Episode 23 Changing What You Accept For Yourself With A New Type Of Storyt...

The truth I’m beginning to accept is that I’ve always been more afraid of succeeding than failing. A...