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

Then I’m aware that I’m braced for impact and, since I’m trying to do less of that these days, I take what I hope is a subtle deep breath.

“So, what do you do?”

We’re at a brewery for a casual, happy-hour style baby shower for our friends. I’m standing at a hightop along the wall with a few familiar faces. And, while I’m soothing the “brace-for-impact muscle,” I find it fitting that, of course, I wound up positioned along the wall in the corner.

Woooooof.

Ok, this is a place of mixed emotions for me. Truthfully, this whole town is. It’s the place where my life fell apart, more than once, and where I returned to put things back together (eventually). For a while, I think things would’ve been too fresh, anyway. There needed to be enough distance to where repair could be possible, so leaving in between was the right move. That’s only something I learned in hindsight, though.

“I work in marketing” I finally replied.

“That’s probably the easiest way to say it, anyway” I added.

I hate that question less than I used to, but it still ruffles my feathers. It took a long time to realize that the problem was my own insecurity with how to present myself. Answering the question got easier when I thought about what they were really asking, which has nothing to do with work or jobs.

More often than not, people ask that question because they want something to talk to you about. Especially if you’re at a social gathering to celebrate your mutual friends. Usually, it’s not an indictment of who you are.

I’ve spent the last 15 years calling myself a marketer.

Only recently did I realize I’d been lying.

Sure, it may have been true once, but what I’ve actually been doing is identifying certain behavior patterns and coming up with ways to elevate them—again and again, for people and for companies. I mean, that’s even what this thing is; what you’re reading right now. It’s a place where storytelling connects ideas to make you reflect on the behavior patterns in your own life. And I’m still working on how to say that plainly when someone asks, “so what do you do?”

But I no longer feel the need to prove my worth in my response.

So that’s something... Actually, that’s a pretty cool realization to stumble across. Especially while you’re at a brewery with the same friends who were there when your life fell apart, and who cheered you on when you pieced it back together.

Our Daily MAP Year Prompt
262/365

What happens in your head when someone asks what you do?

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I’m running by the water just absolutely drenched with sweat, head-to-toe. Sorry. There’s really no other way to say that.

It’s bright and beautiful, so I’m trying to remind myself to look up.

There’s this one stretch of the path where I run that’s a straightaway along the shore between two mini peninsulas. It creates a sort of cove. Instead of sand, it’s lined with these thick, square-ish rocks, so it’s not beachy and people don’t congregate there. So it’s just me on this two-lane bike path, shuffling my way toward the far end of the “cove,” remembering to look up at the lake and the Adirondacks along the opposite shore.

Views like this really do something magical to my nervous system. Mountains, too. But lakes have a special place in my heart. And alpine lakes are on another level entirely. I have this theory about why I’m so drawn to these views, and that’s what I’m thinking about as I trot along in the heat. But first, some context.

While I’m running, I’m doing a version of 4-7-8 breathing that I’ve adapted slightly. It’s an exercise where you inhale for four seconds, hold for seven, and exhale for eight. I usually do it while walking, at the beginning of my run, but every now and again I use it along the way, too. It shifts your body out of the sympathetic nervous system (fight-or-flight mode) and into the parasympathetic nervous system (aka rest-and-digest mode). I do it because it lowers my heart rate, and deactivates the hypervigilant thoughts my brain loves to focus on. Same with playing Eye Spy with my peripheral vision when I’m stressed, or pulling up my hoodie when I want to focus.

Science is cool.

I’m past the straightaway and into the trees beyond it. I’m still huffing and puffing, dripping and dropping, but this short stretch of shade is fantastic.

Now I’m wishing I’d known more about this kind of stuff as a kid. I’ve picked up a lot of helpful tidbits about nervous system regulation over the years since then. Some from the sports I played and from coaching athletes at a high level, some from crisis intervention and therapy, and tons more just from being interested in it. Seriously, my podcast queue is full of the stuff... I even keep a spreadsheet of past episodes I’ve listened to that stuck with me.

Anyway... this is all connected to my theory for why I’m drawn to certain naturescapes more than others.

It’s the peripheral vision thing.

Expansive landscapes create an openness that makes me incredibly calm. I’m pretty sure it’s why I loved living in Wyoming so much. I mean, there are plenty of other reasons, too, but the Tetons and greater Rocky Mountain West are this far-away-backdrop to a ton of wide open, tundra-like flatland. It becomes extremely apparent when you’re up on top of any of those peaks. Having grown up in New England, where the mountains are hills and the neighborhoods weave between trees that block the big-picture view, living out west was a literal breath of fresh air. It calmed my nervous system and helped me move through life at a calmer baseline.

The sun hits me full in the face as I pop out of the tree-cover. For the rest of my run, I keep looking out over the water and, even though I’m absolutely drenched with sweat, I’m not huffing and puffing so much.

Things feel lighter.

Our Daily MAP Year Prompt
261/365

Do you use any tricks to help yourself calm down when needed?

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

I’m looking at the clock this afternoon and playing imaginary tetris with blocks of time. Like if my Google calendar was 4D and I could drag and drop things in the air in front of me. It’s hot. Sweaty and stuffy come to mind as words to describe it, but not sweltering. Let’s just say it’s gorgeous out and I’m happy to enjoy it from this side of the windows for now. So, I figure if I time it right, I can catch the evening cool-down on my run and avoid the midday melt.

I know if I change into my running stuff now I’m more likely to just get up and go later. So I do. And when I walk back to my desk to do just one more thing, I blink and suddenly I’m out of time. No more running for me. Today’s imaginary tetris blocks no longer fit in their invisible floating container. I barely have time to change and get out the door for dinner.

The best laid plans of mice and men often go awry, as they say.

And, regardless of whether the credit goes Robert Burns for his poem or to John Steinbeck for his book, the meaning here remains the same—

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

Our Daily MAP Year Prompt
260/365

When you can't fit everything in, how do you choose? No seriously, I'm asking...

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Ok, but what if it works out?

And, what if it goes even better than expected?

Those are questions I don’t automatically think to ask. I need to be reminded to consider them more than I care to admit. Focusing on the stuff that can go right is a muscle I’ve had to train after a lifetime of contingency planning. Sometimes I feel like I’m just an amalgam of contradictions.

Life as an athlete taught me “the best defense is a good offense,” but life as an outdoor guide proved that “anything that can go wrong, will go wrong.” That, and there’s no such thing as bad weather if you have the right clothing. So, learning to expect the best hasn’t come easy. I quite admire the folks who do it well, though I admit I used to think them incredibly naive. I’ve always rooted for them, but I sort of secretly thought they’d learn the hard way, sooner or later.

I’m ready to say I was wrong about that.

Time and again, I’ve watched things work out for folks who thought they’d work out, just as I’ve watched things repeatedly fall apart for the folks who expected disaster to strike. Myself included.

We find what we look for. All we can really do is prime our autopilot to look for the good stuff. That way, even when things go wrong, which they will, you’ll find the good thread.

Make sure you follow that one.

Our Daily MAP Year Prompt
259/365

So... what if it works out? And, what if it goes even better than expected?

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

UGH.

Ok, fine. Yes, I do.

But I’m in my kitchen, still trying to finalize a game plan.

My friend called last night after a multi-week game of phone tag. It just restarts once we inevitably connect anyway, which is kind of the whole point, but this had been a particularly impressive back-n-forth. “What are you doing tomorrow?” he’d asked, without preamble. It was the way he asked it. That’s what always gives him away...

He already has plans for us. I’m sure of it. I’ve known him for almost 15 years, so I was well aware that I’d just been ensnared in what would probably turn out to be an incredibly fun last minute plan. That’s his specialty. For a guy who lives and breathes procedural integrity as a med school student, he does incredibly well with spontaneity.

“Wanna go skiing?”

Um, what?

My mind starts racing. I know he means snowboarding, but that hadn’t been what I was expecting at all. Truthfully I’d already accepted the end of the snow season and was actually excited to go for a longer run in the sun by the lake. But then I realize we never got to go together this season. I thought about countering with a proposal to grab coffee instead, but then did some quick math: car ride there, gearing up in the lot, time on the chairlift, car ride home. That’d be a lot more time to chat and catch up.

So here I am, running late and scrambling between the closet and the kitchen while getting ready to go. It’s a stunningly beautiful morning. The sun’s out, and I already know I’m going to be dripping sweat if I wear my hoodie. And yet, I slept like shit, I’m irritable, and I’m seriously considering just un-making the bed and crawling back into it. But the coffee’s brewing, which is good; I’ll be needing that if I’m going to find enough energy to hop over patches of rocks and grass while sliding downhill through some slush on May 16th. I still need to fish my boots out of the closet, and I should probably grab my board while I’m thinking about it so I don’t forget that either...

He’s lucky I love him.

On second thought, I’m the lucky one.

I know it’ll be fun. Pushing myself to get my things and get my ass out the door is the right move today. Especially because he and I don’t get to see as much of each other as we used to. Sure, I’m tired, but the thing I’m actually worried about is that snowboarding will stir up a bunch of messy shit for me. Sometimes I tell myself I’m supposed to love it because I always have, but making it my job ruined it for me and I’ve never quite been able to get it back. So in recent years when I’ve gone, I feel this gap between how much I’m supposed to love it and how much I actually do. And that has a tendency to, well... make me sad. Since I’m aware of this phenomenon, I sometimes resist opportunities to go at all. Like I’m doing right now.

Climbing into my truck to go meet my friend, I realize I’ve already done the hardest part. There’s no more decision; I’m out the door and on the road. I’m past the point of no return on bailing, and that makes things so much easier. Maybe I don’t actually have a fear of not liking snowboarding enough anymore.

Maybe this has just become a fear of... fear.

Our Daily MAP Year Prompt
258/365

What’s something you built up in your head so much that building it up became the problem?

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I’m rounding the corner on my bike and looking over my shoulder in the opposite direction. No cars is a good sign since I’m coming up on the intersection and I need to cross.

It’s a cool day; damp but not wet from yesterday’s rain. It looks like it might again, but I chose to bike anyway. I figured the worst that happens is that I get wet. Realistically, I’d just wait it out at the coffee place if I had to.

I look up at the light and wait for the walk sign. Across the street, I notice a guy pushing a stroller and holding a cup of coffee. He’s waiting to cross, but I can’t see his face now because he’s bent down behind the stroller. Still, I’m thinking he looks a lot like my neighbor. Then the light changes. We each start to cross and, sure enough, it’s him.

“oh hey!”

I see the flash of recognition and his face bursts into a smile.

It was a quick encounter; it’s not like we could stop and chat in the middle of the road, but it was truly a pleasant surprise. I’m smiling now, too, pedaling onward toward the coffee shop, and I’m betting that’s where he just came from.

I used to run into people I knew everywhere.

It was sort of a running joke among my friends—if we went out somewhere, they’d place bets on how long it’d be until I bumped into some I knew that they didn’t. Then, they’d try to guess how many other times it would happen the same day. I was involved in a lot of stuff across many social groups back then. And I never sat still—I was always bopping between them.

As I’m walking into the coffee shop, it dawns on me that I went through a bit of a self-inflicted dry-spell there. About five years’ worth, actually... give or take. My spirits lift on my way to order when I realize I’ve been running into folks again quite a bit. I literally ran into someone I went to high school with last week on the sidewalk while I was out jogging. And another friend from college biked past me by the water a few days ago. I even ran into an old coworker at a concert recently that I haven’t seen since leaving that company.

Settling into a table along the brick wall, I’m feeling like I’m “back.” Back to being the me without the social training-wheels from before I got sober. And I’m thinking it’s time to tell my friends to start placing bets again.

Our Daily MAP Year Prompt
257/365

When’s the last time you realized you’d changed seemingly overnight?

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You know, how certain smells remind you of a distinct memory of your grandmother? Or, how a certain song makes you feel like you’re back in the life-changing moment you associate with it?

I’m sitting in a crowded cafe doing some research while rain’s pelting the window. There are a few groups among the tables who are chatting, and plenty of folks throughout the room looking at their phones. My laptop’s in front of me, and I’m combing through my “saved” section of Substack to get a feel for something. I’m looking at how other authors are creating their titles, because it’s something I feel like I really have to work on. Based on a tip from , I’m starting with the ones that caught my attention—the stuff that got me to click.

A few catch me by surprise, but most hold up. Honestly, I’m shocked to see a couple of them have so much engagement with titles that just feel really clunky. Then I start clicking through the top posts of some bestsellers... and my heart drops. More accurately, though, my jaw clenches.

The yelp of screeching wooden chairs on the floor perfectly punctuates my frustration. Everywhere I look, there seems to be a growing compulsion to over-explain things, and under-experience them. I don’t know about you, but I’d love to see more folks sharing their experiences instead of just their takeaways… people sharing with their senses instead of just trying to make sense—

To cut to the chase.

​To reveal a concealed truth.

To hit people over the head with an answer.

Frankly, I’m fucking sick of it. I’m scrolling through clickbait listicles about nothing that went mega viral. Hot takes that contradict themselves without resolving any claims within that have thousands of shares.

What the hell?

I’m sitting there trying to figure out what happened to us, collectively. Very likely, it seems this has to do with the polarization (and infamy) of AI. That, and people look to be latching on to a more surface-level type of communication in an attempt to fit in and be heard. The irony is deafening. Because, at the same time, I’m seeing posts and posts about the collective exhaustion brewing with regard to these quick-hit, condensed, and flattened “after the fact” synopses.

I’m the kind of person who wants to know what happened. There’s a reason why smells, sounds, sights, and frights stick with us. They have everything to do with how we experienced the thing. Happiness, surprise, fear, anger, sadness… that’s what gets left out when you cut to the chase. Yet, it’s the very stuff we’re all searching for when connecting with others.

Glancing around the cafe, I’m watching people sitting across from each other and... emoting. In person. Smiles, furrowed brows, raised eyebrows. There’s folks sitting upright with anticipation, and others leaning in with curiosity. The ones who aren’t on their phones, anyway.

Stories matter—

They bring us together.

Don’t forget to share yours.

Our Daily MAP Year Prompt
256/365

When someone asks you what happened, do you start at the beginning? Or do you edit, clip, and zip to the end?

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I was dripping sweat, but refusing to slow down.

I’m in my office, and Isobel’s just gently suggested that I need a break—some time away from screens. She’s right, of course, but it’s got me thinking wayyy back to my first backcountry ski trip where I was the only snowboarder. For some reason, that always sort of seems to be the case...

The memory comes flooding in, and suddenly I’m in college, it’s spring break, and a group of us are in Idaho, spending the week camping in the mountains. Our university offered an avalanche safety course, and a few friends and I had signed up, claiming a majority of the available spots in the limited group. We’d hiked in carrying our 50-pound backpacks, stuffed with everything from ski clothes and sleeping bags, to pots to cook with and food to eat, but each of us had also brought smaller packs to use for day trips. And I don’t think any of us were really prepared for just how much it was going to snow, anyway... Getting up in the middle of the night to the bathroom meant swimming through belly-button deep piles of the stuff.

One day, we’re out on a ridge, nearby to where we’re camping, and snow is falling in a flurry of fat, fluffy, flakes. We’d just ridden one of the deepest runs of our lives to date and, collectively, decided to hike back up and do it again. So, after grabbing some water and shedding a couple of layers, we began climbing.

It was my turn to go first.

As the only snowboarder, I’m hyper-aware of not doing anything that could slow the group down—snowboarders have enough of a PR problem as it is without giving folks more reasons to be prejudiced against us. So I’m hauling ass up this ridge, keeping an extremely quick pace, and my lungs are on fire but I’m trying my hardest to hide it. I didn’t have to worry, no one was close enough for it to be an issue. Which is good, because sweat’s pouring down my back and soaking through my shirt under the pressure of my pack.

Once I hit the top of the ridge, I didn’t rest.

I grabbed my layers from my bag, flipped my board and bindings from hiking mode to riding mode, and was ready to go by the time the last person in the group popped through the trees and plopped down on the ground next to us.

That’s when I rested; while they were getting ready to go.

Back in my office, I’m wondering why I still do that.

Our Daily MAP Year Prompt
255/365

When do you rest—before you need it, or after you’re cooked?

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

I’m sitting in the waiting room at the dentist. Among the high-pitched buzzing, ringing phones, and low murmurs, the receptionist’s voice jumps an octave when leaving a voicemail. I listen to voicemails, but I know plenty of people who don’t. And while I do check them before calling back, I don’t leave any of my own.

Just about every seat is full.

The guy next to me was here when I showed up. We were the first two people through the door when they unlocked it for us. He’d even cracked a joke with the staff person on his way through. His voice was lighthearted, if just a bit coy. Now, we’re both done with our appointments and waiting to check out.

Out of the corner of my eye, I see his foot’s tapping and gaining speed. I’m replying to some emails on my phone, but he’s staring at the floor like it just swore at him for no apparent reason. I’m looking down with my brow furrowed when I hear the explosion.

“UM, CAN I CHECK OUT SO I CAN LEAVE?! PLEASE??”

The background noise continues without interruption.

“Sure thing, I can help you right over here” someone says a little too cheerfully.

Wow, ok...

So, does this happen a lot?

I’m sitting there trying to process what just happened... I just watched a business take their first customer of the day, who’d walked in joking with the staff, and send him on his way, absolutely fuming.

And no one batted an eye.

Our Daily MAP Year Prompt
254/365

What would you have done?

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

Isobel’s still tending to her coffee. Done stirring, she secures the lid and looks up at me before breaking out into an expression full of shock.

“A small?? Is that a SMALL?!”

I don’t need to glance down at the cup in my hand to know the answer, but I do anyway, and then I make a show of holding it up toward her.

“Yep” I say with just a hint of pride.

I go on to tell her I’ve been doing it for a while; opting for a small instead of the largest size I can find. Pretty much since the doctor told me to, actually. Which is why a grin emerges on my face. One or two small cups a day is a massive reduction for me. And the achievement feels good.

So, turning toward the register together, I remind myself to enjoy it.

Our Daily MAP Year Prompt
253/365

What small victory are you celebrating today?

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I’m zoning out with the water running.

It’s mid-morning and I’m doing the dishes. Isobel swears by doing them at night, but the tactile nature of it just does something for me when done in the morning. Much like coffee, it’s one of many things that help to jump-start my system. You know, stuff like doing the wordle, connections, or the crossword. When I face the puzzle of doing the dishes in the morning, it makes for a day that starts well and just keeps building from there. And I find that incredibly ironic.

Truth be told, I actually hate doing the dishes.

Can’t stand it.

Peeling my eyes from the window in front of me, I make a mental note to close it before I leave. Then I put down the knife I’m holding on a dish towel to my right, and reach through the much-too-hot-but-not-quite-burning water for the faucet beyond. With the water finally off, I take in the silence for a minute.

Maybe I hate doing the dishes because I worked the dish pit in the service industry once upon a time and it’s the worst job I’ve ever had. Though, it’s also the job that probably taught me the most about life. That’s crazy to think about.

Doing the dishes is one of life’s certainties, even though everyone only mentions death and taxes when they talk about stuff like that. There’s no getting out of it. I mean, I guess you could hire people to do the dishes for you, but then something else would just become your new “doing the dishes” and you’d hate that, too. And as much as I hate doing them, I’m not sure I’ll ever outsource it for that very reason (if given the chance).

The drain seems to gurgle its approval.

Our Daily MAP Year Prompt
252/365

Are you a dishes at night or dishes in the morning kind of person? Why?

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Instinctively, I start turning the volume down immediately.

At first I’d hit pause, but I’m trying to be better about withstanding awkward, embarrassing, or otherwise confrontational social situations when depicted on screen. I’m watching “Gary,” an unannounced episode of The Bear. Apparently, it got released as a surprise ahead of the show’s upcoming fifth and final season.

It’d taken a second to register what I was looking at when I first opened Hulu. Seeing the name “Gary” didn’t make me think of The Bear, and it wasn’t until I saw Jon Bernthal and Ebon Moss-Bachrach pictured side-by-side that I even thought to connect those dots.

Did they star in something else together?

Wait...

Hold on, is this a spinoff?

Reddit solved the mystery for me. “Gary” is a flashback episode, referencing a roadtrip to Gary, Indiana, involving Mikey and Richie (Jon and Ebon). Honestly, it could be a standalone short film. Maybe that’s why they listed it as a different show? I think that, after the marketing splash subsides, that choice will be incredibly clunky.

Talk about confusing for a first-time viewer. AND, even if they wanted to change it later, it’s not like they could just transfer it into an existing show-listing without losing all the streaming data...

I catch myself.

What kind of dork starts thinking about software system governance when faced with a new, surprise episode of a show they love, anyway? Not my problem... So I’m sitting there on my couch, leaning forward with my arms in my lap, and I’m cradling the remote while toggling mute on and off. Jon Bernthal’s character, Mikey, is just completely zooted and being an asshole to his best friend.

I’m watching his facial expression dip in and out of vulnerability and fear. I see self-protection flash across his eyes, disguising itself through hatred and animosity.

My heart’s racing now and I’m squeezing my thumbs between my pointer fingers and middle fingers on each hand like I’d do as a kid before I ever had this stupid fidget ring. Somehow, my chest is hollow and tight all at once. For a guy who can’t make it through five minutes of The Office without cringing, I’m thinking I’m doing pretty good.

It’s just a TV show.

It’s not real.

It’s not yours to hold.

This show has spent four seasons making us fall in love with Mikey. We knew going in that the entire premise of The Bear is Mikey committing suicide and leaving his just-about-bankrupt Chicago restaurant to his younger brother, Carmen (Jeremy Allen White). Season after season, we’ve been given breadcrumbs of an abusive family environment and moderate glimpses into the insufficient coping mechanisms of everyone involved.

So I’m staring at the TV and I’m grinding my teeth, trying to remember to take deep breaths. I knew Mikey was an addict. I knew he was sweet and kind, and deeply troubled. I love The Bear for making him so undeniably human.

And I hate how much of it I recognize.

Our Daily MAP Year Prompt
251/365

Are you someone who feels what the characters feel when you watch TV or movies?

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I feel smoke rising from my ears.

I’m sitting in a coffee shop, hunched over my laptop, and every time I go to take a sip from my mug, it only makes it about half-way to my lips before I set it back down.

My laptop screen is either goading me or encouraging me, but I can’t tell which. I can almost picture the cogs of my cognition working through this puzzle. 15+ years of building resilient marketing operations and enablement teams had, ironically, left me feeling like I’d completely and utterly lost my voice. So when I started my newsletter just over two years ago, I’d hoped it would help me find it again by forcing me to write regularly.

And it did—that’s exactly what I’ve been doing.

Sitting back in frustration, I finally do take a sip of coffee but it turns into more of a gulp. I’m facing a problem with brand consistency; specifically, with publishing through Substack. But, I notice I’m not dismayed in the slightest... I’m fully engrossed in finding a way to make it work.

The issue is with the email header/banner image. It’s the thing that shows up above everything else in the email—title, subtitle, name, any featured image(s) in the body etc. I’ve been using a wordmark with just “Unobstructed” in black text on a white background, which I like, because it kind of gives newspaper vibes.

There’s a slight hiccup, though.

Initially, I’m stuck because you can’t set different email headers for different sections of a Substack publication (aka each of the columns within Unobstructed). Having recently introduced a new monthly column, “Breaking Trail,” written by a new contributor, Caleb Walker, I want to differentiate it (slightly), but without confusing people. Even though I announced and promoted it, some folks only skim and/or don’t fully comprehend updates until they’re directly face-to-face with them.

Especially since it’s still new, I don’t want the column name + Caleb’s name to catch people by surprise, you know like, “what is this? I never subscribed to something called “Breaking Trail”? And who’s Caleb?”

And I think I finally figured out what to do about it.

But first, some context:

I send the email version of this daily column, “Kickturn,” via an automated trigger on my own website, which is hosted through HubSpot. I also make it available on Substack, but it doesn’t get sent via email through Substack, therefore it doesn’t inherit Substack’s email header settings (that can’t be customized by column within a publication, which is dumb). So, instead I use a wordmark as an image in the body text that reads “Kickturn” so it shows up at the top of the page like a column header.

And, I use the same typeface as the newspaper-vibed wordmark of the whole Unobstructed publication. Like this—here’s an example of my daily column, Kickturn, sent via email, from my website/HubSpot:

And here’s that same example, but from the desktop view via Substack:

See the difference?

I do.

It actually bugs the hell out of me that I can’t get them even more congruent... But I’ve put countless hours into coding and tweaking the template files of the site itself to get it to where it is now, and I feel good enough about it to point my energy elsewhere.

My coffee’s cold, but I’m still tinkering with how best to format this new column, “Breaking Trail” in the text editor itself. This gets published both via email through Substack—where the publication’s universal header settings are in effect—and online through Substack, where those header settings don’t apply.

Wanting to maintain consistency with the other columns of the publication, I’m thinking it’s best to try for something that incorporates visual hierarchy, while following the naming conventions and guidelines I already use everywhere else. So I opt for keeping the universal email header, and then add a column-specific wordmark below a brief block of introduction text. That way, it acts as the preview text displayed in readers’ email inbox, its branding is recognizable once opened, and the transition into the new column is distinct, without feeling disruptive.

Doing that makes it look like this via email sent from Substack:

And like this online, where it’s web-hosted via Substack:

As always, this is a work-in-progress. But small steps stack up, and tiny tweaks become big accomplishments... Like, starting a newsletter two years ago to find my voice, and growing it into a publication with five different columns.

• Kickturn — a daily column on pivots and new perspectives.

• Unobstructed Weekly — a weekly column on rethinking your next step.

• The Unobstructed Podcast — monthly conversations on navigating daily life.

• Breaking Trail — a monthly column on trying new things.

• The Monthly Dispatch — a monthly roundup of what’s new from Unobstructed.

Placing my coffee mug in the bus tub, I head to the door while trying to process how this writing thing led me to compete in The Moth’s StorySLAM competitions and get featured on GBH’s Stories From The Stage, too.

Our Daily MAP Year Prompt
250/365

What’s something you’ve been working on where, eventually, the hurdles feel fun?

onward.

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

I’m on the court in the park near my house, and I’m going back-n-forth between wondering what I’m even doing here, and feeling like I’m actually not doing so bad. You know, but for a guy who hasn’t really played since he was a teenager.

It’s cloudy, but bright enough that sunglasses help. There’s a chill, but I’m fine in my shorts and T-shirt so long as I keep moving. I was wearing a hoodie, too, but I took it off after it was messing with my shot by tugging on my arm. Which, yes, is embarrassing; especially since I started shooting better without it.

Right now, though, I’m taking my layup for having missed my last shot. I’m playing “Around The World.” At least, I think that’s what it’s called. I’m taking a shot from each hash mark around the paint, in order, and only moving on to the next one if I make the last one. Miss, and I take my layup and start from the beginning. Just like back in the driveway as a kid.

As I’m going for my layup, I’m picturing my step-brother, Danny, and the one-on-one games we played growing up. He was on defense, and, in a rare moment of graciousness, trying to teach me something instead of just kicking my ass. He was working on getting me to drive to the hoop and finish strong, rather than drifting off at the last second for a fade-away shot, like I’d been prone to doing. I was short by basketball standards (and all standards, really). In any case, I was a guard—shooting threes was kind of my thing... I was perfectly happy not driving to the hoop for a layup. Danny was older, taller, and unequivocally more skilled than any peer I’d play against in a game with guys my own age. And I’m still not convinced he wasn’t just doing this with me because it let him body me back and swat every shot I’d take.

Backyard sports was just what we did. We’d start with basketball, then switch to lacrosse, maybe to soccer, over to football, back to basketball—again, and again, and again. If it rained, we played Madden. It was definitely an “entertain yourself” kind of vibe, but it worked for the most part.

So I’m on the court today, dribbling toward the hoop for my layup after a miss, and I hear him taunt me “to go up strong.” And then I do. Somehow, my body still remembers how to do that, even after all these years. Basketball wasn’t even my sport—football was. I played lacrosse, too, but I dropped it in high school after a couple shoulder surgeries. Speaking of... that was the strangest part of this whole basketball excursion today: shooting with adult muscles and limited shoulder mobility. I think my form was ok, but I had no idea how much oomf to put into shooting at first. A few bricks off the backboard and just a couple of air-balls helped to recalibrate things.

I made the layup.

And I even started splashing some threes, too.

Cracking a smile, I had to admit that, in a weird way, Danny’s beatings had worked. In basketball and in life, knowing when to go up strong is important. So is learning how to not get pushed around.

I’m dribbling, albeit slowly, and alternating between left-handed layups and right-handed ones. One, then the other. Back and forth. Looking across the empty court, I’m wondering if there are effective ways to cultivate grit that don’t involve pain or suffering. That’s been coming up a lot recently in conversations I’ve had with folks around grief and proactive mental health. I don’t know that there are, but I’m also not prepared to say I’m sure about that, either.

New ball, same me I suppose.

But it’s nice to be having fun again.

The small steps I’ve been taking are adding up.

Our Daily MAP Year Prompt
249/365

Is there anything you learned from a sibling or a friend, that showed up years later as a pretty core life-lesson?

onward.

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

The Note said, “When nothing works don’t force it. Take a break.”

And it sounded like something I’d tell myself.

So I replied with what I’d actually say.

Give yourself some grace.

Change up your pace.

Get some space.

That’s my GPS.

Works great.

Try it.

Our Daily MAP Year Prompt
248/365

What do you do when you’re stuck? What’s your version of a GPS?

onward.

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Thunder boomed and lightning struck.

I’m looking out the window feeling dismayed. Since I didn’t run yesterday, I was pretty hell-bent on going today. But it’s not like I’m psyched up and ready to go.... it’s more like I’m feeling guilty.

The thing is: I didn’t run on Sunday, either.

I did, however, play a full game of soccer. Our rec league just started up again after a winter-long hiatus, but that doesn’t show up on my tracker in Strava. So it looks like a gap—a demerit against my consistency—even though it isn’t. That damn calendar view showing which days of the month I ran plays mind tricks on me. I don’t even care about the metrics all that much.

I’m not a “do it for the stats” kind of guy. I do like a nice consistency streak, though... their app developers got me good in that regard. Still, I’m watching waves of rain crash down and wondering if I could do something inside if I had to. Maybe an AMRAP of burpees, squat-thrusts, and crunches? I decide to wait and see what happens with the weather, turning my attention back to my work.

When I finally look up again, I’m not quite sure how much time has passed. All I know is that it’s not raining right now. Truth be told, I’m kinda mad about it, too. I hadn’t been all that excited about running before, it was something I was going to do begrudgingly. But now, I’m feeling exhausted.

I do not want to run.

The sky is clear-ish, but darkness looms in the distance. I figure it’s probably now or never.... and a glance at the clock confirms it.

Shit.

As I’m getting dressed, I’m reminding myself that I never regret writing and I never regret going for a run. I know I’m right, and that in itself is annoying. Pulling my shoes on, I calmly explain to my petulant self that while I may not always want to run (or write), I’m always glad I did.

I’m right again, and I know it.

Yuck.

Our Daily MAP Year Prompt
247/365

Do you push yourself to do stuff you don’t like, but that you know will pay off later? Why?

onward.

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I’m on my fake, morning commute as a remote worker (aka a walk around the block) when the podcast I’m listening to makes me shuffle to a stop.

The trees are budding—some are even flowering—and for a moment I’m distracted by the realization that Spring has finally sprung in full. Still, it’s a little crisp and I’m wearing a jacket, but the birds are chirping and gardens are blooming throughout the neighborhood.

I’m listening to the Finding Mastery podcast, where Sam Harris and Michael Gervais are talking about honesty. It feels timely. I wouldn’t have described my approach to honesty as “radical” until recently. When responding to a reader about navigating proactive mental health resources, I shared a few practices of my own before caveating their reliance on unbridled honesty with oneself.

I think that surprised me.

Sometimes, I suppose I still think of myself as the kid who fibbed to avoid getting in trouble... even though, rationally, I know I’ve grown into a far different person as an adult. Turning my attention away from the budding branches of the trees along the sidewalk, I start moving my feet again while replaying the last 30 seconds of Sam and Mike’s conversation in my headphones. They’re using the classic “do these pants make me look fat” example as a way to talk about honesty. Sam’s just laid out one of the best explanations of why people lie that I’ve maybe ever heard. So I hit pause and keep walking while I think on it some more.

I treat being honest with myself like radical acceptance. That’s a Dialectical Behavior Therapy (DBT) skill where you completely accept things—even the painful stuff— in order to move toward change and minimize potential suffering. It’s come up in therapy, but I think I learned it most formatively when leading outdoor trips; you can’t change the fact that it’s raining, but you can do plenty of stuff to make it suck less.

As I’m rounding the corner back onto my street, and finishing my remote work commute, it occurs to me that I’m inclined to call my approach “radical honesty.” But, almost instantly, I hate it. I’m trying to figure out why we need to use “radical” as a qualifier for acceptance in the first place... it’s as if the definition of the word has become too culturally eroded.

From what I’ve seen, radical honesty tends to make folks very uncomfortable.

Most people might think they want honesty.

They might say they want honesty.

But, really, they want validation.

We all do to some extent.

I finished my walk lost in thought, before even realizing I’d never pressed play again on the podcast. Back inside, I’m hanging up my jacket when it clicks: more often than not, people ultimately just want to be accepted. We ask for honesty while hoping for confirmation that what we think, feel, say, see, or do is right. And the thing is, asking for honesty inherently means inviting the possibility of being wrong—daring someone to tell us that what we’re thinking, feeling, saying, seeing, or doing isn’t quite as accurate or acceptable as we thought.

Knowing how uncomfortable that can be, yet choosing to be honest anyway is hard. I see it as a kindness; as an opportunity to accept things as they are in order to do something about them.

You know, or not.

That choice is up to each of us.

Our Daily MAP Year Prompt
246/365

What do you make of the term "radical honesty"?

onward.

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

And, yes, it’s exactly what it sounds like; a desk on the other side of my office for all things non-digital. For example, that’s where my typewriter lives. But, right now, I’m folding zines and thinking about balance. These zines are freebies from as a thank you for pre-ordering his new book, Don’t Call It Art. Which seems like one of the best modern marketing promos I’ve come across in a while. They’re full of passages, sketches, and stories that didn’t make the final cut, but that still support the contents of the book.

Brilliant.

Anyway, I’m folding and folding, and the anticipation is growing... I’m wondering what kind of stuff Austin liked so much that he found a way to publish it even if after his editor axed it from the book. And, ok look, I was the kid who never tried to sneak a peek of Santa because I wanted to be surprised on Christmas morning, ok? I wanted to believe, not be proven wrong. And yet, I was also the kid who refused to see the movie until he’d read the book because he wanted to have all the facts in order to audit the temerity of any creative license taken by the film.

In that regard, some things never change.

Finally, I set down my bone folder and start flipping through the small stack of zines where I find this passage referencing Adam Moss, who wrote The Work Of Art. It talks about how art requires a balance of play and rigor in almost equal measure. And I’m sitting there reading and re-reading the quote.

He goes on to say “[when there’s] too much of the child, and your work has no structure. Too much adult and the thing has no fire.” That, I like. It’s where he says “so this crazy middle ground... is somehow where you have to live” that trips me up.

So I lean back in my seat. I’m thinking about past chapters of my life and whether or not I’d achieved the ever-elusive balance of play and rigor that Moss is talking about.

And I’m stuck.

The part of the quote that talks about having to live in the crazy middle ground... I don’t know if I fully agree with that. Because, I can confidently say, believing I could find that balanced middle ground has only ever made things worse for me. In fact, I’m pretty sure that’s the recipe for burnout. At least, that’s what’s been present each and every time that I’ve burnt out.

I lean forward, perching my elbows on the surface of my analog desk and resting my chin in the crook of my hand between my thumb and index finger. My eyes snap out of their far-away-gaze and return to the stack of zines in front of me. I let out a slow sigh and shake my head. Reflecting on my own journey, I can’t find anything to disprove my hunch. And I want to be wrong. I’ve long wished I could achieve balance; that I could attain and maintain it. But, looking back, everything points to balance as something that’s not meant to be achieved, only pursued.

Aiming for balance helps me get closer than if I don’t.

To me, I see play and rigor like opposite sides of the same teeter-totter. And the whole point of a teeter-totter is the back and forth; the up and down.

It requires constant motion.

Our Daily MAP Year Prompt
245/365

Is balance something you achieve or something you pursue?

onward.

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

It’s early, not many places are open yet, and they’re laughing. I’m bleary eyed, but smirking, as I catch bits and pieces of their banter. The cashier’s sheepishly admitting that she looked both ways when leaving her house this morning... to walk to her car in the driveway.

The guy she’s talking to is shaking his head.

“Patty, you need a day off” he says.

He’s probably right from what I gather. The cashier—Patty—looks exhausted, but she’s cackling jovially, if not a bit deliriously. I’ve been waiting a while at this point but I don’t press. What’s the point? This is a general store attached to a gas station in Vermont. Patty’s the only one behind the counter, and there’s only two other people in the store besides me. And it’s not even 7am.

Patty’s wiping her tears from her eyes now that her laughing fit’s dying down.

I’m still waiting, but there’s a smile on my face. Admittedly, I was hoping they’d have food, though it looks like the grill’s just getting started and nothing’s ready yet. Unfortunately, I don’t have time to wait. Sure, I have a long drive ahead of me, but so what? A confrontation with Patty would only kick off the next part of my drive on a sour note. Plus, it’s objectively funny picturing Patty looking both ways for oncoming traffic across her lawn before taking a few steps to her car in the driveway. And I tell her so. The laughing resumes.

“Just the coffee?” she chokes out?

“Yep” I say with a nod.

“Cash or card?” she asks.

“Card please.”

She starts tapping some keys on the register before catching herself and looking back up at me.

“Oh, ya know what... you’re all set, hun” she says. “Don’t worry about it.”

It took me a second to realize she’d just gifted me a free cup of coffee. So, I smile graciously and thank her. Then I make a show of looking both ways before opening the door to return to my truck parked six feet away.

Patty starts cackling again as the door clinks closed behind me.

Our Daily MAP Year Prompt
244/365

When's the last time instant karma worked to your benefit?

onward.

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I’m walking through the grocery store and I hear “dad, you gotta use your brain here.”

I tried to stifle my double-take but I’m not sure how good I did. Off to my right, a guy and his teenaged son are standing in front of a freezer door by the ice cream. They’re looking at an array of Ben & Jerry’s flavors, clearly trying to come to some kind of consensus together.

The son sounds matter of fact. Whichever flavor his dad picked was apparently more expensive... and, with that, the son seemed to think he’d won.

I kept walking, shaking my head with a grin.

They’re gonna get both.

Dad’s buying; no way he gives up that easy.

A few minutes later I see them at self-checkout and, wouldn’t ya know it, two pints of Ben & Jerry’s were stacked in the bagging area next to them.

Hell yeah.

Good job guys.

I’m still trying to stifle a laugh, but now it’s because I’m picturing a very obscure reference to a commercial from 2009 where a girl choosing between hard and soft Old El Paso tacos says “Por qué no los dos?”

Why not both, indeed.

For whatever reason, that phrase stuck with my friends and I, so it comes up a lot. But, as I’m walking out of the store, I’m thinking about how something as simple as getting both flavors of ice cream when you can’t decide just... makes sense. Why not, you know? Go for it. And as I’m on a mission to inject more joy into my life, I went back in and snagged a sweet treat of my own.

Joy is on the menu for me in May.

What I’m up to in May 2026...

Since I’ve been trying to be better about sharing the process instead of just the product, here’s my latest 3x3.

1. Monthly updates:

1. Got to share my story on national TV!

2. Celebrated another birthday.

3. Ran into a river otter.

2. Primary focus areas:

1. Send more gratitude letters.

2. Play more (aka rec soccer returns)!

3. Connecting with folks who’re looking for ops help.

3. What I’m currently reading:

1. Oathbringer by Brandon Sanderson.

2. Save The Cat! Writes A Novel by Jessica Brody.

3. Chapter 9 of The Artist’s Way by Julia Cameron (for the MAP Year Project).

Our Daily MAP Year Prompt
243/365

What does your 3x3 look like?

onward.

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