Becoming Unobstructed

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...

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...

The Unobstructed Podcast: Episode 22 How Childhood Dreams Predict The Person You Become by Derek Mac...

The Unobstructed Podcast: Episode 21 On Letting Things Break by Derek MacDonald Making a hard choice...

Being honest with yourself means acting like your own best friend. There’s nobody in this life you’l...

The Unobstructed Podcast: Episode 20 The Most Important Skill For Becoming A Better Collaborator by ...

We need to teach people that collaboration earns approval instead of teaching them that conquering d...

The Unobstructed Podcast: Episode 19 The Overlooked Half Of 'The Let Them Theory' by Derek MacDonald...

The Unobstructed Podcast: Episode 18 Learning How To Be Yourself Instead Of Staying Quiet by Derek M...

So when you’re scared of the unknown? Connect with others by sharing your experiences. Don’t fall ba...

The Unobstructed Podcast: Episode 17 Digging Out Of Content Fatigue With A Different Approach To Pos...

Gaining competence is good if you intend to go use it in response to lived experiences. But it can e...

The Unobstructed Podcast: Episode 16 The Invisible Tech Tax On Solopreneurs by Derek MacDonald Makin...

Confidence doesn’t come from knowing where to go. It comes from knowing you can keep going, even wit...

The Unobstructed Podcast: Episode 15 The Art and Science of Becoming Happier by Derek MacDonald How ...

I kept seeing other people trapped in the same invisible quicksand time and time again, but no one w...

When Dan Harris referenced The Red Wheelbarrow in a podcast conversation with Rich Roll, I was gifte...

The Unobstructed Podcast: Episode 14 Part 3 - What They Don't Tell You About Sobriety In The Workpla...

The choice is yours: you can be interpreted or you can be understood.

The Unobstructed Podcast: Episode 13 Part 2 - What They Don't Tell You About Sobriety In The Workpla...

Being prepared isn’t about being able to control what happens. Being prepared is about being able to...

The Unobstructed Podcast: Episode 12 Part 1 - What They Don't Tell You About Sobriety In The Workpla...

Planting your feet firmly enough to be stable, but lightly enough to take another step. Because you ...

The Unobstructed Podcast: Episode 11 The Reason You Don't Listen To Your Gut (and what to do about i...

If what they said didn’t match how it made you feel when they said it… Go with your gut. That’s a to...

The Unobstructed Podcast: Episode 10 From Tolerating Bad Conditions To Navigating Better Circumstanc...

Learning happens on the edge of our comfort zone. Growth happens outside of it. Want to grow? Take t...

The Unobstructed Podcast: Episode 09 Neurodiverse Confidence And How To Destroy It by Derek MacDonal...

Problems That Solve Themselves When You're Not Looking by Derek MacDonald Sometimes focusing on some...

The Unobstructed Podcast: Episode 08 Your Mental Wealth Is Your Best Investment by Derek MacDonald U...

Focusing on doing it faster makes a mess. Focusing on doing it well makes progress.

The Unobstructed Podcast: Episode 07 If Your Data's A Mess, Your Results Will Be Too—Even With AI by...

“But how do you find your competitive advantage?” It was a good question. Especially since I’d said:...

The Unobstructed Podcast: Episode 06 Why Some People Shape Their Future While Others Wait For It by ...

The Unobstructed Podcast: Episode 05 Your Workload Is A Mess—And What To Do About It by Derek MacDon...

“Work harder” used to sound like “move faster” in order to get more done. Intentional velocity is wh...

The Unobstructed Podcast: Episode 04 Solopreneurs and The End Of Employer-Sponsored Retirement Plans...

The Unobstructed Podcast: Episode 03 Time Management Isn't Your Problem by Derek MacDonald Fitting m...

The Unobstructed Podcast: Episode 02 Use This Skill For More Work-Life Balance by Derek MacDonald Re...

Resisting new and innovative ways to navigate causes more discomfort than it avoids. That’s why help...

The Unobstructed Podcast: Episode 01 How to Manage Expectations Without Stifling Growth by Derek Mac...

Engaging with failure as a puzzle rather than a punishment is how we can create resilience that endu...

Teaching people to use curiosity to help others feel seen—enough so that we feel safe being seen as ...

The holidays and I, historically, don’t get along so good. Oh I enjoy them just fine, but like many,...

Game-Changing Gifts for the Procrastinators in Your Life ($45 and Under) by Derek MacDonald Gifts th...

Dry Wit, Charismatic Charm, and...Unabashed Vulnerability? by Derek MacDonald Leaning into change in...

Why Jon Brosio is Using Lessons From Food Service to Build Digital Trust by Derek MacDonald How leve...

Your Ability To Make Progress Is Directly Tied To Your Relationship With Avoidance by Derek MacDonal...

Relatable Blind Spots, Limiting Beliefs, And Coaching Yourself by Derek MacDonald Finding the refram...

1 Goal, 2 Milestones, 3 Tasks To Do Today by Derek MacDonald A traumatic brain injury changed how I ...

Here's How Artificial Intelligence Will Wreck the Economy by Derek MacDonald What happens when produ...

The Overlap Between Therapy, Sobriety, Stoicism, And Mindfulness by Derek MacDonald Do we really "fi...

What Mass-Casualty Medicine Teaches You About Decision-Making by Derek MacDonald Plan for the worst ...

It's Not Always About Fighting For What You Want by Derek MacDonald The path of least resistance—fou...

Your Progress Depends On What You Document by Derek MacDonald How records help you spot patterns, tr...

What Overcoming Limiting Beliefs Really Looks Like by Derek MacDonald Tom Matousek didn't start "goi...

How To Keep Calm In The Middle Of Chaos by Derek MacDonald Wining the crowd, setting your standard, ...

Only Pain Will Change It by Derek MacDonald The hard truth about turning awareness into action.Read ...

Driving Sales with Functional File Sharing by Derek MacDonald Better operations are the key to unloc...

Finding Clarity With Fear And Transparency by Derek MacDonald When feeling small leads to going big....

Relatable Inner Critics For Reducing Stress by Derek MacDonald How Fredrik Backman makes the charact...

Lord of the Files: The Solvable Practice Creating Uncertainty in the Workforce. by Derek MacDonald A...

The Struggle For Happiness No One Will Talk About by Derek MacDonald Do emotional intelligence and h...

AI and the Biggest Workforce Threat That No One is Talking About by Derek MacDonald Transitioning fr...

Understanding Motivators, Strengths, And Blind Spots by Derek MacDonald Starting on Substack, focusi...

Escaping The Chaos While The World Sleeps by Derek MacDonald A story of connecting purpose with proc...

Embracing Structured Imperfection for Getting Work Done by Derek MacDonald When good is "good enough...

Goal Setting, Redefining Success, And Better Planning Resources by Derek MacDonald How will you know...

The Phases Of Lasting Change by Derek MacDonald Productivity gets mistaken for the goal, but account...

Making it to a Million by Derek MacDonald In a room of 100 people, 7 are likely to be millionaires—b...

Stories On Personal Growth, Leadership, And Building Mental Wealth by Derek MacDonald Introducing 'B...

If You Give a Moose a Mindset by Derek MacDonald Read on Substack

Go From Overwhelm to Organized with this Simple Task Triage System by Derek MacDonald Learn to prior...

5 Pillars of Performance that Every Leader Can Use. by Derek MacDonald Read on Substack

How to Coach Yourself Through the Worst Weeks (and what it really sounds like). by Derek MacDonald 5...

Paving A Path by Derek MacDonald Randy Strand builds community through snowboarding.Read on Substack

Powerful Community by Derek MacDonald Local nonprofits strive to provide outdoor opportunities for J...

10 Barrel Brewing Emerges in Snow Markets by Derek MacDonald Read on Substack

Does Your Work Shape Your Life or Does Your Life Shape Your Work? by Derek MacDonald The time you sp...

Meet The Digital Nomad Who Ditched His Dream To Find A New Life by Derek MacDonald A destination he ...

Wilderness First Responder: What It's Like To Use It by Derek MacDonald How a snowboard trip in July...