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

It’s pouring rain today. On the bright side, I’m sitting by the window at a local coffee place I like and the crowd’s died down a bit. It was bonkers when I got here. I walked in kind of expecting it to be empty. Nope. Lucky me, though, a table in the corner was open. I’d been reluctant at first — it’s by the window, but it’s also by the exit and I’m not a huge fan of being in the traffic lane. That always seems to happen to me at concerts... it’s like, no matter where I stand, it ends up being the spot people walk through.

Again, it’s raining today; so I was fairly confident people wouldn’t be hustling and bustling through the door near me. And I was right. Truth be told, I probably wouldn’t have even realized if they had. Since my arrival (and for a decent chunk of time prior), I’ve basically been wearing my laptop on my face like VR goggles. Maybe then I’d be able to get this data set to play nice. I’ll spare you the details, but basically VLOOKUP, XLOOKUP, and FILTER have failed me thus far, and I actually blame HubSpot. As I’m sitting there with rain splattering the glass by my head, I’m actually shocked that you can’t bulk edit “tags” for posts. I’m working on an exciting next evolution for theunobstructed.com and it requires tagging posts a certain way so I can filter them and link to groups of them later. However, while working on that, I’ve come to accept that I have two options:

1. Manually go back and re-tag every post I’ve ever written.

2. Export my entire site into a CSV file, add the tags, and then import the file as a new “blog,” essentially.

What’s frustrating is that I’ve already aggregated a spreadsheet with all of my posts. I keep a backup master file, but then also use it to create copies for things like this. And yet, I’m trying to reconcile a sheet with the old tags and one with the new tags, without wiping out all existing tags when not necessary.

I’ll figure this out.

I’m sure of it.

Stay tuned.

Our Daily MAP Year Prompt
332/365

What's a skill you learned as a kid that you didn't know would be useful as an adult?

onward.

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Today was a build day for me.

Chris Bailey says there are really only three types of days we humans can have: building days, maintenance days, and rest days. I kind of sort of hate that Chris is right, but it’s also made life a lot easier for me since I started thinking of things this way.

I’m sitting at my desk in my office and I’ve just realized it’s dark. Like, it’s very squarely night-time and I don’t know the last time I ate. Whoops. So I’m sitting there in my office with the lights off and I’m staring at the open template file terminal on my laptop and the lines of code I’ve been tweaking in my latest journey to bypass some of HubSpot’s default functionality. With a sigh, I resign myself to sitting in the near darkness for a bit longer. Those template files are always in some version of dark-mode, anyway, so I’m still shocked as to how I managed to miss the fact that the sun set.

I’m thinking about how I did something kind of radical and left my laptop behind when we went to Maine over the weekend. It’s the first time I scheduled this column ahead of time during this entire year-long daily writing project. I felt weird about it... like I was cheating or something. But I was also running on fumes, and I knew the time spent playing outside was something I needed dearly. So I did it—I wrote a couple posts ahead of time and scheduled them to send without me.

I’m glad I did it, and I hope you don’t fault me for it too much.

Some days are for swimming towards something (figuratively or literally, you pick), some are for treading water, and some are for floating. I’ve spent years tinkering with ways to engineer the right conditions for making “building days” almost inevitable. I’m good at it. I’ve acclimated to a life of very high output. I don’t say that to brag; it’s been helpful, sure, but I also struggle significantly with sitting still after years of priming myself to lock the fuck in. Which, you might have deduced, is why I’ve been working on learning to follow my energy and accept the day I’m capable of in the moment, rather than trying to force it to be something it’s not.

Easier said than done.

On my way toward the kitchen, I still reach to shut off my office lights that are ~not on~ because apparently, I’m a creature of habit. This weekend was a rest weekend. I’m ok with that. Yesterday, was a maintenance day of getting caught up on life stuff like laundry, cleaning, bills etc... and I’m ok with that, too. And then today, without really meaning to, I accidentally had a week’s worth of building days in one.

I’m smiling while shuffling toward the fridge to find some dinner.

I used to get worried when I couldn’t replicate my “hyperspeed” days, as I called them. The torrent of guilt and shame I felt at not being able to conjure a building day when I needed one, or at being paralyzed by the weight of life on a self-appointed rest day, often made me miserable. I don’t talk much about my AuDHD because I think I still feel largely misunderstood in that realm. For a moment, though, between grabbing a frying pan and reaching to turn on the burner, I think about the mountain of stuff I sifted through and the progress I made today... and I feel my shoulders release their grip. I hadn’t even realized the boa-constrictor mode they’d been in.

My eyes feel hollow, but I don’t.

Oh, right—

On my way back to the frying pan waiting on top of the stove, I flick the kitchen lights on.

***

Also I saw this floating around online and I wish I knew who posted it. I have not audibly cackled from a meme like I did when I saw this in a long, long time.

Bravo, whoever you are.

Our Daily MAP Year Prompt
331/365

Do you follow the tides or try to generate your own waves?

onward.

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Ever catch yourself after saying something and think “Wait; who was that? Did... did I just... is that really what I think??”

I was trailrunning today when I slammed face-first into one of those situations.

I’m running up a particularly steep section of this gravely-ish road. Well, it’s not really a road. It’s more of a trail... But it’s basically just wide enough for a four-wheeler or something. And there are two “sides” of this trail where the tires would go and then a divider in the middle, which is growing thigh-high grass since this place doesn’t allow ATVs.

So I’m rounding a corner of this zig-zagging trail before I get to the spot where I’m going to head into the woods, and I keep running until it flattens out a bit and turns into a straight-away. Dripping sweat, I reach for the soft water-flask on the left side of my vest. When I start trotting again, a small bird swoops out of the brush across the path and then back. I’d startled it. So now I’m thinking of a puzzle I did a few years ago at my friend’s lake house that was bird-themed. A group of us had gotten together and my ADHD loved that puzzle as a side-car to our chit chat. The bird I’d spooked might’ve been a Blackpoll Warbler, but I’m not really sure. Either way, it settled further into the woods and I audibly said “I’m not your enemy; I’m a friend.”

Which is how I ended up spending the rest of my run wondering why I led with what I’m not before presenting what I am.

Our Daily MAP Year Prompt
330/365

lorem

onward.

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

I’m about two steps from the railing, one step from needing to leap, and the voice in my head picks now, of all times, to ask “hey, wait; are you sure you got this?”

Um, WHAT??

With the guardrail of the bridge right in front of my face, I find the wherewithal to mute that voice. I’d started second-guessing this front flip off the bridge and into the water below, but the milliseconds before swan-diving over the railing is not when rethinking is helpful. Those have actually been the moments in life when things have gone terribly wrong.

As I’m approaching my takeoff, I blatantly ignore the thoughts trying to run through a safety check since it’s far too late... what foot am I planting before jumping? Should I touch my hands on the railing and push myself over? Thinking about things like that, at times like these, are the kinds of distractions that lead to tripping, smacking your face on the edge while gliding past, or over-rotating and belly-flopping from far-too high to walk away uninjured.

Nope.

Nope, nope, nope.

I remember one summer at my grandparents house, I’d decided I was going to teach myself to flip into the pool. I ate so much shit. My cousin, Chris, was going to learn with me, but after seeing how many belly/back-flops I’d endured and how red my skin was because of it, he decided against it. A year or so later, I did the same thing with learning how to do “gainers” off the diving board at summer camp. Running off the board facing forward, but doing a backflip into the water, was hard as hell to get used to. But it was the funnest thing I’d ever figured out how to do, even if my crashes resulted in a couple hundred kids chanting “belly flop!” every time I’d climb back up on the board in the hopes I’d indulge their requests and intentionally splat myself onto the surface of the water.

At least I’m dry right now; my chances of slipping are much lower compared with that diving board...

And we’ve already been through this, amigo.

I checked—counted out the paces, visualized which foot to plant (and where), and decided not to touch the railing to minimize anything from fucking with the rotation. So, already mid-stride across the double-yellow lines on the bridge, I tell myself I’m “clear.” That’s a habit I picked up cliff-jumping as a teenager at the quarries in Massachusetts when I’d damn near shit my pants getting ready to jump from 80 feet.

Next thing I know, I’m watching the railing float by beneath me. I see the lake and hold my arms out above my head, waiting.

Not yet.

I feel the familiar momentum of falling through the air, slowly tipping forward with every inch.

Not yet.

The weightlessness feels sooo good. I really missed it. It’s been a while since jumping from height—either into water or snow—and I’m always blown away at how my heart stops thundering right before taking off. Floating like this feels familiar.

NOW.

I crack a smile and start to tuck my head to my chest. I feel my feet lift above where my head was and look to spot the treeline as I come around. Untucking to slow myself down, I have enough time to hear that same voice in my head that’d been worried up on the bridge go “Heyyy, alright. Not bad!“ just as my feet slide into place below me.

Then I hit the water, exactly as planned.

Our Daily MAP Year Prompt
329/365

What do you do when you second-guess your muscle-memory?

onward.

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I’m not convinced that my default level of self-awareness is a good thing. I get in my own head a lot, which is sometimes good for my writing and sometimes it’s not.

I hoped I’d have more traction by now; more subscribers, more reach. It’s not that I care about stats so much as it’s the opportunities tied to them. Long before I started publishing stuff online—before building websites or launching a media company—I think writing played an enormous role in helping me become someone capable of loving their life and the people in it. Podcasting, too, for that matter. Which is why I’d do both for free, even if they never made me another penny. But, if that truly is all they’re ever meant to be, their roles need to look different than they currently do.

I’d love nothing more than for writing, editing, and podcasting to be my full time job.

In fact, I’m trying to make that happen.

That’s the goal, eventually.

But that requires a certain threshold of subscriber count, traffic, and engagement. On average, you need about 1,000 subscribers before monetization becomes a viable option. For podcasts, that viability looks more like getting 1,000 - 5,000 downloads per episode. And, look, when I say “monetization” I’m not just talking about having individual subscribers pay for access, and I’m not talking about using email marketing to sell courses or services.

I’m talking about monetization here through a lens of earning the ability to partner with brands, advertisers, affiliates etc... And, this is actually something I wrestle with a lot. Because on the one hand, I desperately don’t want to dilute the reader/listener experience of Unobstructed by introducing silly ads, but on the other hand, the right partnerships would shield folks from the burden of having to pay subscription fees in this hypothetical land of future “monetization.” And, until now, I’ve wanted the stuff I write/publish to be free and discoverable to those who believe in narrative storytelling instead of the pervasive advice-mongering that tries to play whack-a-mole with your head wherever you show up online. So, if I were to offer readers a more robust paid option down the road, I’d want to introduce something that would be valuable to them, in addition to what we’re already doing.

However—

As of today, which is day 328 of The Map Year Project, Unobstructed has 845 followers on Substack, 462 free subscribers, and 8 paid subscribers. Realistically, that number will probably drop again later this week when I publish our newest podcast episode...

So it goes.

I’ve spent two and a half years publishing my writing on Substack, and I think I’m more proud of what I’ve built throughout that time with Unobstructed than anything else I’ve done in my career. Still, this journey can also be really disheartening at times. On LinkedIn, a platform I hardly ever go on, I have 1,363 followers. And then on Instagram, that number is 1,533. Which is wild to me since I basically stopped using my account in February of 2023.

All to say, there’s an uncomfortable truth I’ve been grappling with for a while now that’s only getting harder to ignore: people just might not be interested in what I have to offer. But the bigger truth I’m facing is that I’m not sure whether or not that sentence should have a “yet” at the end of it.

And as the saying goes, the market decides.

Sure, I’ve thought about quitting; I’d be lying if I claimed otherwise. When I publish something that took a ton of work, yes, it absolutely sucks if it flops or lands flat. Of course I hope people will “like” it or comment on it. And you bet I love when something I wrote meant enough to someone for them to share it with others. So, yeah, when it feels like stuff’s just whiffing completely, I can’t help but ask myself “why the fuck am I even doing this?“ And that’s when, despite feeling hurt in the way that comes from feeling like you’re being ignored, I inevitably ask myself if I like what I published.

It’s when I ask myself if I believe in what I’m doing.

Throughout the past two and a half years, the answer to those questions has been a “yes,” albeit sometimes with more conviction than others. In the downtrodden moments, a follow-up question I ask myself is whether or not I’d keep writing—and publishing—if I knew no one would read it and I’d never be paid to keep doing it. I can’t explain it, but I never feel any hesitation with answering that one. I don’t have to think about it before my brain says “of course.”

It’s at that point that, still feeling a little prickly and defensive, I start melodramatically wondering why, then, don’t I just stop engaging online altogether and stick to writing in my notebook... after all, no one’s going to read it anyway, right?

It surprised me at first when I realized it but, out of all the questions I ask myself i moments of uncertainty, that one’s undeniably the most useful. Like, without question. Hands down. Because after thinking my through that entire saga, it’s that last question about the idea of just sticking to journaling that makes me remember why I keep showing up online, and it’s the real people who read and react to what I create.

Since embarking on this journey of reclaiming my voice, there have been folks who’ve taken the time to leave heartfelt comments on my stuff about what it meant to them. I’ve received emails in response to things I’ve published that have brought me to tears. Ironically, it’s the pieces that get the least traction online that tend to get the most replies via email.

Just when I think “why bother?” or “no one’s even reading,” I’ll get a text from someone I haven’t talked to in a while saying how much they’ve enjoyed keeping up with what I’m publishing. I’ll run into people in real life who tell me similar. Often, that’ll happen with someone who I had no idea even subscribed. But they all end with some version of the same thing: keep it up. Some of those conversations were even with people who became clients.

I don’t know if or when I’ll hit 1,000 subscribers.

Who knows if the market wants my stuff.

I like the me who writes.

So I’m keeping it up.

Our Daily MAP Year Prompt
328/365

Do you have something you'd do for free, even if no one paid attention?

onward.

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

In her summer update, Maggie talked about relatively docile things, and sounded more like one of us normies, than she could’ve. She visited family in Maine, absconded to Greece, watched the World Cup, jet-set to Boston and then on to London where she teamed up with Ralph Lauren at Wimbledon. Then she’s talking about chasing “wonder” and, as I’m reading, I can’t help but think the privilege in that. And now I’m faced with recognizing my own...

I’ve got plenty.

I mean, I’m a relatively educated white guy from the suburbs of Boston. I also know what it’s like to work multiple jobs while perpetually afraid of not being able to pay rent. I know what it’s like to live on credit cards to preserve what little cash I had until I could pay it off later. I know the disdain that comes from hearing people talk about needing to budget or “just live within your means” when the problem is the amount coming in, not the amount that’s going out. And, I know what it’s like to climb out of a life like that—where becoming literate in personal finance was finally relevant, and where thinking in percentages, rather than dollar-amounts, was actually applicable.

It costs money to do things, obviously. But I can’t help but feel it’s reached a point where doing almost anything requires spending a decent chunk of change.

Yes, yes—there are plenty of free things out there, too. But when I think of the stuff I want to do in this life, like go to a concert or an event, or maybe take a trip somewhere far away and hop from coffee shop to coffee shop as a way of acquiring a taste for a place, my daydreams sometimes deflate like a whoopie cushion.

I’m looking at Maggie’s words on the screen and I can feel the levity beneath them. But I’m still hung up on something... At what point does wonder teeter from concern to curiosity? Where’s the line between “Wow... I wonder if I’ll be ok” and “Wow! I wonder what’s next?!”

Our Daily MAP Year Prompt
327/365

Is your version of wonder steeped in concern or curiosity?

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Hey, I’m Caleb. Welcome—or welcome back—to my monthly column, Breaking Trail, where we kick things off with a dad joke. Just like this, just because.

In 2017 I had the opportunity to chat with the prolific (and now famous) climber Alex Honnold. In the world of outdoor sports, he was already well known but this was the year he catapulted into the greater zeitgeist due to the premiere of the film Free Solo. I remember being starstruck, questioning both myself and my outdoor pursuits. After sharing that I’d read his book while thru-hiking the Pacific Crest Trail (PCT), he responded with “Wait, you did the whole thing?”

I nodded.

“Wow, I could never do that” he said.

My world stopped for what felt like an eternity. After processing what he’d just said to me, smiling sheepishly and shrugging it off, we chatted a bit more and both went our separate ways.

Here I was, placing this individual on a pedestal due to his accomplishments while devaluing my own. I hadn’t written a book nor did I have any corporate sponsorships, but I’d still done something that this prolific outdoorsman considered a true challenge for him. I’d forgotten this lesson as I resumed my day-to-day life, chalking it up to the well-known fact (at least among the climbing community) that most climbers despise hiking. Hiking is what you have to do in order to reach the crag, which is where you can start to do what you want to do. I rationalized away Alex’s praise as a version of his relationship with this. In reality, it was a far more poignant lesson, one that I was already aware of but needed reminding:

Hike your own hike.

Your Friends and Neighbors, starring Jon Hamm, was the number one show on apple TV when its second season premiered. We won’t get into whether or not this ranking is substantiated on what is actually most popular with viewers, or just a result of what the platform is trying to push. Either way, the entire premise of this show is “stop trying to keep up with the Joneses” which feels like the mass population’s version of the outdoor industry platitude, “hike your own hike.”

While these statements are used so often that most of us merely roll our eyes with condescension and let out a “I f***ing know” collective sigh, I think they ought to be re-assessed through a lens of what this means today; particularly with social media in the mix. The Joneses aren’t just a fictitious family up the street anymore, who happen to have everything you want. They’re every person you’ve met (and many you haven’t) who post their lives online. This is especially insidious as these platforms are designed solely for engagement. They want us to keep scrolling, not feel like we’re actually caught up with everyone.

When the Joneses were just someone in our social circle with whom we shared physical proximity, we saw them “IRL” more than we do now. We had an anchored frame of reference — the good and the bad — whereas, on social today, we only get to see what people have oh-so-carefully curated. It’s never a real look into their day-to-day; it’s the insta-perfect moment. Go to your feed, scroll for 5 minutes, come up with what you think the average household income is for the friends, family, and influencers you saw. Odds are, the number you landed on is quite high, yet only 18% of Americans make over $100K a year. The profiles we see don’t look like it because everyone wants to look like they’re winning.

This framing is tantamount in reconciling what we all see as normal for “the Joneses” compared with the rest of our lived-reality. Hike your own hike means living your life the way you want to and, most importantly, understanding that time, wealth, and happiness are all subjective. Every person is hiking their own hike, and that looks different for each of us.

Don’t yuck my yum.

I wish I could remember who introduced me to this phrase.* It’s been something like 5 years since learning of it and it’s become a very consistent zinger for me to use. I love it. It’s a far more interesting and conversation-stopping way to call someone out on “if you don’t have anything nice to say, don’t say anything.” I am thoroughly convinced that our collective society of armchair-experts has completely abandoned this premise due, in part, to online anonymity. However, I think it’s such a key factor in how we can move through life.

At its core, this whole thing comes down to cultivating a capacity for empathy. If you were talking about something that excites you, how would you feel if someone else just spewed vitriol all over it? Bad, right? Then don’t do it to other people.

There are currently 8.3 billion people on planet earth and roughly 349 million in the U.S. alone. There are countless preferences, opinions, and beliefs held among them. Some are singular, others are shared across communities, faiths, and divides. That said, each and every one of them should be respected.

Don’t yuck my yum.

It applies so beautifully because it immediately subjects us all to an undeniable fact: taste is personal. While your group of friends or broader community may have shared beliefs and interests, your tastes will differ. Try to order a meal for everyone… These disparate preferences will become apparent quickly.

We need new ways of cutting through existing platitudes. “If you don’t have anything nice to say, don’t say anything at all” feels too time-worn. Should we simply shut up and bite our tongues? Meh. Don’t yuck my yum means “this is personal.” This is a matter of taste and preference. Everyone’s palette is their own and is as unique as their fingerprint. To deny that would be like claiming that an entire category of food or beverage is disgusting. When, if that really were the case, it would’ve stopped being consumed during the course of human evolution.

My deepest desire is that we could all internalize and further practice the application of “don’t yuck my yum” across our lives. From our political preferences and our religious beliefs, to our hobbies and interests — all are a matter of taste and preference. Something that’s a yum for me may be a yuck for you. That’s fine.

We each have our own palette.

Follow your arrow.

One observation I picked up from moving consistently throughout my childhood is that we, as people, crave “associated originality.” That’s since been reinforced for me both in work and in life. We seem to be attracted to what is cool, even though true “coolness” requires a certain level of IDGAF that most of us can only aspire to. We want to be like the cool kids who manage to keep up with the Joneses. We even want to yuck other peoples’ yums if it means we can become cool, too. Because all of that feels safer than going out on a limb and owning our uniqueness. We don’t want to be original, we want to be close to it.

There is a ton of research across psychology, sociology, and behavioral economics that touches on this subject, but there are two key principles from the work of Daniel Kahneman and Amos Tversky that I’ll bring up here:

1. Loss Aversion: Psychologically, the pain of a loss is twice as powerful as the pleasure of a gain. A novel idea represents a massive potential loss (loss of time, money, or social status if it fails). The human brain heavily overweights the risk of failure over the reward of success.

2. Status Quo Bias: This is an emotional preference for the current state of affairs. The existing baseline is taken as a reference point, and any change from that baseline is viewed as a loss or a threat. Truly original ideas demand that people change their habits, which causes genuine cognitive friction.

Taking these theories into account also invites a unique sort of juxtaposition, from my perspective. These are verified and well researched truths — we all (to varying degrees) experience loss aversion and status quo bias. Yet, we all also hold ourselves to a standard where we feel we should be able to be original, unique, and self-expressive, while simultaneously maintaining the status quo. This is friction. And this is what feels maddening to me. If we all experience these things, why can we not then give more grace and space to everyone following their own path?

Gen Z, every marketer’s favorite demographic to talk about, might actually be the biggest exception in this regard. Perhaps it’s due to how online they were through adolescence. Regardless, while trends of keeping up with the Joneses still objectively exist, they appear to welcome a more open discourse about personal uniqueness and originality. This is contrary to how many of us Millennials grew up, where being in the spotlight may have been the most terrifying thing imaginable. It takes a significant amount of maturity and self-determination to decide, “I’m going to do this, because I want to, and I believe in it.” I laud every person who is pursuing their yum, following their arrow, and daring to be original.

We’ll never be able to keep up with the Joneses, but we can hike our own hike.

Just don’t yuck my yum, mmmkay?

Cheers,

Caleb

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* Editor’s Note: It was Derek who introduced Caleb to “don’t yuck my yum.” You’re welcome :)

P.S. In addition to opening this column each month with a dad joke, I’ll be closing them with a musical coda—songs and lyrics I feel touch on the theme of the essay.

Musical CODA:

Follow Your Arrow (Live at the Grand Ole Opry) by Kacey Musgraves

Key, relevant lyrics:

“When the straight and narrow gets a little too straight. Roll up a joint, or don’t. Just follow your arrow wherever it points, yeah, follow your arrow wherever it points.”

If you enjoyed reading this, take a gander at the other columns from Unobstructed. You can sign up to get them directly in your inbox here.

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

I’m running on the bike path today by the water and it’s nice out so there are a lot of people milling around. Some folks are walking, others are biking. Some have dogs. A few are rollerblading and one or two are riding electric scooters. Some, like me, are running. I’m sticking to the right side of the path except to pass, and I’m hollering a crisp “on your left!” when I do.

Maybe it’s because I grew up skiing and that’s what my mom said skiers do, but I’m religious about it. It’s just... considerate. Plus, when I was a kid, my cousins and I would often being skiing together and we raced around the mountain like Tasmanian Devils. And we uh, well, we caused some trouble... So by instilling in us the credo of “on your left!” maybe my mom figured we’d at least be giving people a fair warning that we were tumbling through.

Well, as I’m trudging along by the water today, someone on an E-Bike comes ripping up from behind and swerves between me and a couple heading the opposite direction. So I jump off the path at the last second and scrape my way through the bushes along the side for a few steps.

Wow.

What an asshole…

I’ve never met anyone who had worse road rage than my dad did, so after seeing how mad he’d get and how long he’d stay that way, I’ve tried to develop a habit of letting go of any frustration as quickly as I can. It’s not always easy, but it feels better than wasting my energy fuming about something I have no control over. So I take a few deep breaths, and then cycle through a couple rounds of box breathing.

Good as new.

But then the same thing happens again. This time, it’s a mom and her two young kids on regular bikes. No “on your left!” No sheepish “sorry!” Nothing.

What the f—

Deep breath.

I’m going to enjoy this run. It’s beautiful out; like low 70s and slightly breezy. Not too sunny, but not cloudy either. I can smell fresh cut grass and the flowers along the waterfront park are in full bloom. My ankle’s not perfect but it’s doing so much better than it was. Life is good.

So when someone grazed my shoulder from behind, I turn and find another runner being overtaken by a couple of athletic looking cyclists. This is happening while a few teens on E Bikes are heading towards us, having just passed an elderly couple walking our way, too. Now I’m mad. Not a single one of them says a fucking thing. Not one word from anyone in this mess. I clamp my jaw and feel my shoulders snap closed around my neck. My hands fly up before I fully realize what’s happening. And then, just as my eyes start to flutter and my ears begin pulsing — everyone’s gone.

DOESN’T ANYONE KNOW THE ETIQUETTE IS TO SAY “ON YOUR LEFT!?”

Apparently not.

AM I REALLY MEANT TO CONSIDER EVERYONE ELSE WHEN THEY CAN’T BE BOTHERED TO CONSIDER ME??

Apparently.

More and more, it feels like people expect the world to cater to them! It’s like they feel entitled to accommodations from everyone, and would cry injustice if they don’t get them. And yet, I suspect they would simply never dream of accommodating anyone else.

Grrr.

As I continue my run, I’m picturing how it would’ve gone if I’d called each and every one of those people out for endangering the rest of us. I’m imagining they’d get upset with ME for even suggesting they think of considering the other people around them. Ohmygod... I... I’m the curmudgeony old guy... With a huff, I shake my head. Whatever. I’ve had it. We live in a society, right? That’s the agreement — we’re free to exercise our personal preferences until they infringe on someone else’s ability to do the same.

Blargh.

I’m trying to take deep breaths but I’ve lost count and I’m exhaling when I should be inhaling and now even my running steps feel out of rhythm. We’re in a place of shared space. Where my personal space ends, theirs begins. I am responsible for my side of that invisible fence, not theirs. Glancing out across the water, I notice the clouds are getting darker above the Adirondacks on the other side of the lake. We’ll probably catch a storm, soon. Figures.

While I’m running back towards home, I’m thinking about this idea of social boundaries, expectations, and who owns what when things spill into other people’s space. For me, it feels like if others tether their physical and/or emotional wellbeing to stuff that’s happening on my side of the “fence,” that’s a them-problem; not a me-problem. Until they ask for help without expecting it be bestowed unto them from the start.

If they can do that, then I’m good with it becoming a we-problem.

Our Daily MAP Year Prompt
326/365

Do you consider others or expect them to consider you?

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

There were two other houses at the end of the neighborhood with us, one that was directly next-door and one on the opposite edge of the street that sort of rounded us all into a lopsided peace sign.

I remember this one time, when I was maybe ten or so, a group of kids from the street were playing “pickle” aka “rundown,” a game mimicking the scenario in baseball where a runner’s caught between bases. Then my neighbor’s dad got home from work. He lived right next-door, with four kids, and three of them were old enough to play with us that day. As he drove up, the game paused after a collective “CARRR!!!” rang through the air. That meant time-out. So my three neighbors and I, plus the two boys from the house across the street, and a few more kids from the top of the hill by the main road, scattered to the edge of the cul de sac to get out of the way. As their dad passed through, he rolled down the window with a big grin and asked what game we were playing.

We told him and he nodded.

“Fun!” he said before disappearing down their driveway and into the garage, at which point we resumed play.

There were enough of us that we could have three bases. If the tennis ball touched you while you were running between them, you were “out” and became a thrower. Wild throws that required chase were common. Sometimes they’d land in the woods or bounce through one of the yards nearby, and that gave us plenty of time to run, walk, dance, and/or mock our way between bases. We’d taunt each other, boasting our ability to dodge the incoming green whumph of a ball to the leg or back.

Rebels; the lot of us.

I wasn’t particularly close with our direct-neighbors, but I’ll never forget when their dad re-emerged from their driveway, still wearing his tucked-in button-down shirt and dress shoes, and asked if he could play. I don’t remember him being particularly athletic. In fact, I don’t remember much about him at all. But I do remember he laughed a lot that day. I can still hear it. I remember he joined in and danced between the bases in his work clothes when a ball would go rolling into the woods. And, today, decades later, I find myself thinking of him and smiling.

I remember him.

It makes me hope I never forget that I can ask to play.

Our Daily MAP Year Prompt
325/365

When’s the last time you went out to play?

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Ok, interesting...

I’m at the desk in my office, jumping between tasks—per usual—when I come across a post on LinkedIn about how Substack just launched an AI detection feature.

Huh...

My eyes dart to the name of whoever posted it, then widen when I realize it's from the official Substack page. Um, ok... I lean forward, tucking my forearm under me to reread the text of the post. I'm slightly annoyed to be finding this out on LinkedIn rather than on Substack, but I click to read the full article anyway.

• Substack partnered with Pangram to add “AI Detection” to the drop-down menu.

• It can be used on both Notes and Articles/Posts, but only when at least 100 words.

• Available now on web and iOS and will be coming to Android soon.

• You can run Pangram on your drafts prior to publication.

Taking a minute to pause, I roll a small metal fidget between my left thumb and index finger. I want to think about this. Wind is rattling the trees beyond my windows and, occasionally, it’s slapping small leaves and twigs against the windows themselves.

By and large, I’m not sure if this is a good move on Substack’s part, but I’m also not convinced it isn’t. There’s absolutely been a rise in the amount of AI generated content on the platform, at least from what I’ve seen. People across the internet seem rather split on AI writing—some vehemently oppose it and check out immediately once they sense it, others are more laissez-faire and couldn’t care less so long as they enjoyed what they read.

As I’m turning the fidget over in my hand, I feel a layer of unease form in my stomach. Substack’s a writing platform. It’s designed so people who write can publish their work and distribute it to those who want to read it. The whole premise is that it’s free to use. BUT Substack has built-in features for writers to easily offer paid-tier subscriptions, and the way Substack makes money is by claiming a percentage of each and every transaction on the platform. Oh, and they make it so you must use Stripe, who also claims a percentage of transactions. That’s the whole business model.

I keep reading.

While scanning the info they provide, I land on the “how to” screenshots. Hmmph. Including those was actually a great move. So, I pull up Substack to try it. I don’t use AI on my stuff, but I just published an essay yesterday, and it’s at the top of my screen, so I click. I want to see what this feature looks like in action.

Annddd this whole thing takes a turn.

This AI Detection feature can only be used for stuff published after July 21, 2026 at 11:30am EDT.

I shake my head, lips pursed.

As of now, this new Substack partnership with Pangram is useless for verifying any existing content on the platform, so I have no idea if it's even any good. I can't use my own work to test it, let alone anyone else's. I'm wondering what will happen when people who pay for subscriptions start seeing stuff labeled as "AI generated" even if it isn't. That's been the problem thus far with AI detection software like this. Since the tech industry at large literally stole the work of every literary icon there ever was, it trained on the writing rules of the pros.

Based on what I’m reading, I’m nervous. The internet’s made clear that those of us who learned to write by using classic structures and literary devices are now at risk of being falsely accused as an AI fraud.

I crack a smirk.

Yes, I learned to write by (begrudgingly) following the rules. But then, somewhere along the way, I decided I'd graduated to where I could start breaking those rules; like a jazz player. And, these days, it feels like my style is uniquely mine. I guess I'm probably not the best person to judge how my writing comes across, though...

With a sigh, I slide away from my desk.

Time to face the storm and go for a walk.

***

To Substack’s credit, here are a few quotes that appear like they’re trying to preserve the space for everyone, regardless of technology preference:

“Pangram can only detect whether AI was used to make the text, not whether great human care went into creating it, nor whether AI tools were used as a source.”

“We’re not against people using AI to assist their work, and we think people should be free to choose which tools they use to express themselves.”

“But people should know what they’re getting.”

Editor’s Note: I tried testing the feature again using this piece instead, right before publishing, and here’s what the results look like.

Our Daily MAP Year Prompt
324/365

How do you feel about writers using AI?

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On any given day, I’m caught somewhere between wanting to take a trip with no return ticket and wanting to just go take a nap with no alarm to cut it short.

More and more I’m finding myself in that in-between space of “do the most” and “do the least.”

The near-constant dream of deleting myself from the internet is accompanied by the urge to scream or cry. Thinking of going for a run only leads to the realization that I have too much work to get through. It’s knowing I still have to find time to go food shopping and it’s the giant fucking sigh, clenched-jaw, and feeling of resignation that shows up every single time I remind myself to look for gratitude in the hope of taking the edge off of my stress.

Because it works.

Or rather, it used to work.

After a lot of speculation, I’m not convinced it’s doing anything other than keeping me stuck.

Caught between observing and participating.

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

I just got back from visiting some friends. They’re getting ready to welcome their second kiddo and it felt like a good time to see each other before life gets even crazier. A band we like was playing a small-ish, dive-bar-styled venue near where they live, so I packed my bags and we turned it into a weekend.

The day of the concert, we got there early and managed to grab two seats at the back bar so we could order some food before the show. Each of us hung our rain jacket on one of the hooks under the bartop and got a burger.

He and I started working for the same company 10 years ago and have maintained a close friendship since. The day after we first met, we spent an entire weekend together in Montana on a work trip. The non-working hours of that weekend involved splitboarding, crashing a college graduation party, and one very hazy Afroman concert.

In the time since, we’ve both moved across state lines more than once. He got married, bought a house, and had a kid.

And I got sober.

Chomping on another fry from my plate, I glanced around at the sea of short-sleeve-button-downs, graphic tees, five-panel hats, piercings, and tattoos.

“Is this just my version of wearing a letterman jacket and reliving the glory days?” I asked.

I’ve been thinking about that a lot lately: the difference between living life while looking forward, or glancing backward over your shoulder. And it’s making me question whether I’m observing or participating.

Am I evaluating or engaging?

Searching for certainty.

From our old-guy-perch in the back of the concert venue, my friend and I are talking about how I’ve been feeling sort of stuck. I tell him it’s like I shelved an entire life when I moved to Vermont five years ago, and now I’m wondering if I’ve just been swimming against the current the whole time since.

He nodded and mentioned how Vermont seems to have a lot of the same ingredients that I liked from other places I’ve lived.

“I didn’t think I’d be here this long” I said, then added “I kind of thought it would be temporary.” With a sigh, I turned toward him and admitted that even though it has those things, I didn’t make an effort or put myself out there when I got here because I figured it was more of a pit stop. Watching him mull that over, I’m thinking of snowboarding and the life I left behind but never truly let go of.

There’s this rock feature at Jackson Hole Mountain Resort, where I used to work, that people love to jump off of called Mikey Likes It (myself included). It’s also a great spot for benchmarking someone’s ability level. As a student, it lets them feel what it’s like to ride more advanced terrain in a relatively controlled environment without all that much consequence. And as an instructor, it would always tell me a lot about how the student actually operates. I’d watch their body language before it was their turn to drop. I’d listen to what questions they’d ask and the way they’d ask them—to the words they chose, and the ones they’d leave out. And, after coaching them where needed, I’d watch to see how much of it they’d implement.

As humans, fear pushes against us. It makes us hesitate, which is why scared snowboarders lean too far back and lose their balance when landing. But training yourself to respond to that fear differently is possible over time. Mikey Likes It was always a helpful test in that regard. It’s how I measured my own readiness, too. Coming back from an injury? Lets hit Mikey’s and see how I do.

More than a way to measure skill, Mikey Likes It is ultimately a way of gauging the willingness to lean into uncertainty with confidence.

It’s an indicator of commitment.

Learning to commit.

So here I am, visiting my friend and enjoying the show.

Taking his eyes off the stage, he turns to look at me and asks if it’s me or the place itself. Is it Vermont? So, as I’m sitting there, I’m forced to face the fact that I’ve been trying to keep one foot in my old life and one in the new life I’ve stepped into.

“Maybe there’s just too much scar tissue here” I tell him.

And I know there’s a lot of it, but I’ve not yet been willing to consider whether it’s insurmountable. In fact, I’ve been quite proud of my growth on that front during these past five years and I tell him so.

I tell him how, on my way down from Vermont, I had to pass through Massachusetts and how different it’d been from when I’d done that after first moving back to the east coast. Back then, while stuck in a strikingly similar rush-hour situation, my chest had completely seized in the time it took to go from one exit to the next. That was the first time I’d been back in the area since... probably during college? I told him how I remember thinking I was going to crack a tooth with how hard I’d been clenching my jaw.

This time, in bumper-to-bumper traffic on the same stretch of highway, I was shocked by the notable absence of any chest-tightening or jaw clenching while passing those exits. Commuting through traffic there used to be a fact of life for me. I traveled that road all the time growing up; like, every other weekend. For many of those years I’d been a passenger, yet somehow it was worse once I was old enough to drive myself. Something about having autonomy and still taking that exit never sat right.

From my spot at the bar, I look up at my friend and follow his gaze to the row of drinks being made by the bartender in front of us. With a shake of the head, he turns my way, grins, and goes “hey—when’s the last time you had a Red-Bull-Vodka?” After taking a minute to think about it, I start nodding and laughing while telling him the rather embarrassing story.

I don’t miss everything about my “old life,” but it’s kind of cool to feel… compassion(?) for my younger-self rather than the animosity I used to harbor when thinking about it.

Adding constraints.

Something I love about my friend is his blunt honesty. It’s direct but kind, and I wish more people were like him in that regard.

After the concert ended, we couldn’t help but to chuckle… it’d been a good long while since either of us had been out so late. Then, on the drive home from the show, he pressed.

“If we’re still having this same conversation two years from now, and you haven’t moved by then, we’ll know the problem’s you and not Vermont.”

“Wh—”

I stop myself.

Well… shit.

Deep breath.

“What makes you say that?”

He looked over at me. It seemed like he’d already thought about this and might be pausing more for effect than to gather his thoughts.

“Somebody had to give you a timeline” he said.

Then he added, “And you weren’t.”

I kept my eyes on the road, but he could probably tell I was struggling to think my way out of the logic trap he’d hit me with.

“You build systems better than anyone I know… Time to use your PM skills and add some constraints.”

I felt my eyebrows uncoil while letting out a long, gruff sigh through my nose.

Shit.

He was absolutely right.

Endurance ≠ thriving.

After a shorter night’s sleep than usual, my friend and I say our goodbyes over coffee and I weave my way home to Vermont.

The drive is long but the trip was really, really good. We didn’t “do the most” but we definitely didn’t “do the least” either. I’m sure I’ll still feel the urge to delete myself from the internet from time to time but I don’t feel like I’m going to scream or cry today, so that seems like a win.

I’m still tired, though.

When I was a kid, I was always on the move. I always seemed to have a rotating collection of extra stuff to bring with me, too. Like, going to school wasn’t just going to school; it was going to school with my backpack full of books, my saxophone, and a gym bag for football workouts (before and after school). On the weekends it was a duffle to go to my dad’s house, or a boot-bag and snowboard gear if we were going to my grandparent’s place. I never unpacked my bags. My mom always unpacked hers, though. My cousins did, too, but not me.

Today, it’s just my work backpack and a carry-on sized suitcase.

I like coming back to my own space.

Closing the door behind me, I come to a stop in my entryway. I suck in a huge breath and shake my head. I’m trying to let my shoulders drop, but grimace at how little they move. Until recently, I’d always thought of myself as someone who thrives in transition. Exhaling, I’m reminded that I’m just someone who’s learned how best to endure it; and that’s not the same thing.

Sure, it can be hard to hear… but a good friend, like mine, is willing to say it anyway.

I might be the problem after all.

onward.

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“If you could’ve been born with elite-level proficiency in one skill, what would you have wanted it to be?”

That’s a question I used to ask folks on backcountry trips.

When you’re camping with a group of people for two or three weeks, you’ve got nothing but time to chat. And you’d be surprised how quickly people burn through the usual small-talk stuff. Sillier questions are light and they feel unassuming, but I also found that when you give people a chance to tell you what they like, you can use that info to set them up for success later. That’s originally why I started including questions like that in my weekly scrum meetings with my team leads. I’m pretty sure my boss thought I was crazy at first, but it helped me know where to place people without making them take a personality test. I’d have them run through their team’s updates and then, at the end of their report-out, they had the option to answer the question for that week.

From what I’ve seen, we become interested in our weaknesses if they’re framed as non-consequential. These low-stakes hypotheticals let people volunteer hopes and dreams they might not admit otherwise. And, often, their answers pointed toward real opportunities where they could work toward them.

For example, I had someone who wished they could’ve been born with the ability to understand any language. I took it to mean they liked people, novelty, and detail. So, I later asked them if they’d be interested in working with our project manager to interview folks across our broader team to figure out how they handled task prioritization. They were. Later, that led to helping spearhead an overhaul of our task ticket system.

“Tell me about yourself” is an awful question.

Oh, and if I could’ve been born with elite-proficiency in a skill, it’d be singing.

Maybe that’s why I’ve always gravitated towards stages for other reasons.

And if I weren’t such a chickenshit, I’d take singing lessons.

Our Daily MAP Year Prompt
323/365

How well do you read between the lines?

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

Or, maybe it’s that they spent additional time understanding a thing when I’ve only ever experienced it and haven’t processed its implications. Like, I’m aware that it’s something I think about, but I haven’t yet examined why.

Did you know that the best way to learn stuff is to teach it to someone else? There have been so many times I’ve thought I knew something inside and out until I tried describe it to another person.

That’ll humble you real quick.

It’s also part of why I like writing so much; because it forces me to go through that process quite frequently. It makes me feel far more confident in the things I know and the stuff I don’t. Still, there are times when I come across someone else’s work and am bewildered to discover they’ve distilled my thoughts better than I have. Sometimes, it’s collaborative... as if I got my answer down to 4/16, found someone who managed to get it to 2/8, and then my mind goes “HEY LOOK IT’S 1/4!” Other times, it’s like I’m reading a word problem and then find someone who makes me realize I’ve been doing math this whole time.

I’m a hunter-gatherer.

I hunt for knowledge, and gather ways to apply it.

See this, the thing you’re reading right now, is an example of one of my unfinished concepts brought about by someone else’s nudging. I watched a video by Hank Green on YouTube recently where he talked about the idea of how “no effort is wasted.” Basically, he says it’s a way of life that centers around learning, for the sake of learning, without always knowing what you’ll use it for—just that you will, in fact, use it at some point down the road.

The way Hank framed this whole thing made me realize I’ve been doing math when I thought I was just analyzing word problems. I don’t think I stopped nodding once while he was describing it because this is just how I live my life. It’s how I’ve always gone about it. I do not know how to see it differently. So, part of me is shocked that some people do. I’m surprised this is noteworthy at all, really. What I really, really like about Hank’s perspective on this, though, is the line in the sand he draws between hustle-culture and its obsession with over-optimization, and curiosity-culture. He says outright that doing stuff just because it’s interesting is a worthy pursuit.

Hell yes it is.

“A life is not about getting some fucking task done; it is about building a you“

— Hank Green

Our Daily MAP Year Prompt
322/365

What's your take: can effort be wasted?

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Well, I’ll be damned—they changed it.

I expected this to suck.

It’s rush hour, and I’m driving through Massachusetts on 128. I should’ve known better—left earlier, gone 91 to the pike, stayed on 495... something. This was avoidable. With a sigh, I check all three mirrors and confirm what I’ve already known for forty-five minutes: I’m boxed in on all sides, and it’s not changing any time soon. Not to mention, all the exit numbers are different than how I remember them. They clearly did some huge highway construction project... Maybe this whole thing is finally I-95 all the way through, instead of the spliced-up cluster it used to be back then. Whatever.

Commuting through traffic like this used to be a fact of life for me. I traveled this road all the time when I was growing up. Like, every other weekend. For many of those years I’d been a passenger, yet somehow it was worse once I was old enough to drive myself. Something about having autonomy and still taking that exit never sat right.

Anyway—

About 5 years ago, while stuck in a rush-hour situation much like this one, my chest had completely seized in the time it took to go from one exit to the next. That was the first time I’d been back in the area since... probably during college? I remember thinking I might crack a tooth with how hard I’d been clenching my jaw. Blech. Given that, I’m especially shocked by the notable absence of any fight-or-flight response while driving along the same stretch of highway now, inch by inch. I’m still checking my mirrors more often than I need to, but it’s nice to see myself smiling.

Our Daily MAP Year Prompt
321/365

When face-to-face with your own growth, do you give yourself props for the work it took to get there?

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

Shit, barely a quarter of the way...

This is why I try not to do that.

It’s late afternoon and I’m sitting at my desk in my office. I’ve been here so long the light from the windows has switched walls. Editing podcasts is a completely different type of work than writing, but not so different that they can’t be compared. I mean, I try not to think about them like that but, sometimes, my brain just does it instinctively.

Podcast editing is a “countdown” type of work whereas writing work starts from zero and increases as you go. Audio recordings have a total run time. So, as I’m editing, I can see how much progress I’ve made. That only ever feels helpful when I’m almost done; which I’m not. When I first got into podcasting, I’d start by making in-line edits for things like filler words, dead-air, or flubbed pronunciations of things. Then, I’d move to the story-level trim. You know, things like asking whether stuff even fits or not—whether it strengthens the story arc or distracts from it. I used to treat those like separate tasks. These days, however, they’ve become something I do simultaneously. And right now, with three quarters of this pod left to edit, that helps.

Leaning back, I rub my eyes.

First, though, it’s time for a change of scenery.

Our Daily MAP Year Prompt
320/365

Do you prefer count-downs or count-ups?

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One year ago today, after tearing apart and rebuilding one of my websites, I published a piece about what was to come next called, Keeping The Dream Alive.

Today, I reread it.

Truth be told, I knew this day was coming up but admittedly forgot now that it’s here. It wasn’t until reading this recent piece from that I remembered it’d been a year since publishing my overview of The MAP Year project. Only then did I seek out my own piece to go back through it. Brendan’s piece is about finding himself in a new phase of life. He, his wife, and their son went camping, and Brendan had to wrestle with coming face to face with small twinges of familiarity among a completely different shape of experience than he was used to.

I’m reading his words from my desk, where one of my orchids just bloomed after almost two years of dormancy. It turned out to be a worthwhile game of attentive patience. Come to think of it, that’s sort of my wheelhouse... Anyway, I’ve got my chin in the crook of my hand and I’m leaning my elbow on the black desktop mat protecting the wood. Tipping forward, I’m scrolling with my other hand as my eyes flit from line to line. My jaw is somehow loosening while both proffering a smile and supporting the weight of my hunched-over posture.

He’s just so good...

Brendan routinely manages to capture extremely profound moments while completely avoiding pretentiousness altogether. He doesn’t even go near them. I’ve been impressed by his ability to do that since I first became acquainted with his work circa ~2016. And I’ve often wondered how he built his writing career because I not-so-secretly want to do something similar.

It’s lines like this one:

“Sometimes I joke that growing up is just building your own prison out of things you love, but that’s of course exaggeration—it’s more like sacrificing your own freedom in exchange for things you think will be worth it: pets, kids, a consistent roof over your head, maybe some plants to nurture.”

Pshhhht...

I fly back in my chair with an audible “hoookayyy.”

Hell, I’m probably getting something totally different out of that than I would’ve just a year ago, but reading through it a second time, and then a third, it keeps cutting deeper. I feel its sadness. At the same time, I also feel the hope and appreciation embedded within. As I’m thinking about it, I’m reminded of the phrase “if it were easy, everyone would do it,” and that “it” can refer to just about anything. I’ve also learned by now that we each only get a couple of them; those “its.” Maybe a few if we’re lucky enough to learn that lesson early.

I’m glad I started writing a newsletter a couple years ago.

And that it led me here.

The MAP Year Project isn’t over yet but, even when it is, I know I’ll still be keeping the dream alive.

Our Daily MAP Year Prompt
319/365

What does keeping the dream alive look like to you?

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Well that’s... odd.

That fern is waving at me, but there’s no wind whatsoever.

I’m trailrunning an old route, and it’s been a couple years since I’ve been here, so I’ve had my eyes peeled for the turn I need to take to make this a loop. I knew it was around here somewhere, but now I’m a little spooked because I’ve been trudging up this narrow gravel “road” between a hallway of lush overgrowth, and this single green fern just gave me a royal, cupped-palm wave.

It’s like something out of a Disney movie.

More than that, it pointed directly across the path at the obscured entrance to the trail I needed. After glancing to where it was pointing, I looked back, eyes wide, just in time to see it go limp and flop back over among its peers.

What the actual fu—

I catch myself.

Rather than getting hung up on how weird that was, or looking for logical explanations until I found one I was satisfied with, I decide to roll with it.

“Hey, uh... thanks”

Pushing off of my right foot, I spring across the waterbar and clear the wiry wildflowers that were concealing the rocks leading up into the woods, toward the looping trail ahead.

Hello, old friend.

Our Daily MAP Year Prompt
318/365

When things go right, do you lead with doubt or keep rolling?

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

It’s mid-morning and my hands are clasped around a cup of coffee. I’m tired and can’t seem to break away from it today. This table by the window’s a favorite of mine, the glass juts out far enough for me to tuck my bag up against it so it’s on the inside rather than in the walkway. I’m sitting with my left foot tucked under my right ankle, which is resting on top of one of the table legs. I never know what to do with those. They’re not far enough away to be a comfortable footrest for long and they’re not close enough to not be in the way. Maybe I’m just too short. Either way, I know I’m going to end up readjusting my feet soon.

On the wooden tabletop in front of me, my laptop’s open and there’s a video playing. I’m watching the beginning of an interview with Andrew Stanton to see if I want to add to my podcast queue. He was the second animator hired by Pixar, like ever, and he’s also written and directed a handful of movies for them like Toy Story, Finding Nemo, WALL-E, Inside Out and more.

The first question the interviewer asked was how he thinks about making movies that are captivating for both kids and parents.

He replied with, “Well, we’ve never written for kids.”

I slammed the space bar to pause the video.

Um, what?

Is he serious?

I’m staring at the screen, eyebrows scrunched together, trying to figure out what he means. I’m tempted to just add the podcast to my queue and let the anticipation build, but I cave without much of a struggle.

With a completely straight face, he goes on to say, very matter-of-factly, that kids are exceptionally driven to figure things out. He describes them like sponges who innately know to watch people and then try to infer what’s going on. It’s the adults, he says, that learn to stop doing that over time.

I slap pause again.

Damn.

This is going to be a great listen on my next run.

Our Daily MAP Year Prompt
317/365

Do you try to infer what's going on or wait to be told?

onward.

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

I don’t know where that came from.

But I know that it’s wrong.

At least, for me it is.

Some people talk about creativity like it’s a down-payment on a starter home—you know, something used to get your foot in the door, so it can appreciate and you can move your life forward with all it creates for you. I mean, I guess it’s possible to approach creativity that way, but I always felt like going about it like that implied a certain level of scarcity. It was like, doing that came from a fear that you may never have another great idea, so you better hold that one close. And don’t share it with anyone because they might steal it!

That used to be a fear of mine with writing... well, sort of.

Mostly, though, I worried that if I finally got my shit together and managed to write a book, I may not have anything left to say afterwards. The one-hit-wonder fear. So, if I were really going to do it—write a book—it felt like it would have to be perfect the first time since there may never be a second. And especially so if writing is a form of translation, like I’ve heard so many authors talk about. I’ve read books, listened to podcasts, and watched countless interviews at this point where they’ve described creativity as this thing that you have to be ready to harness when it strikes. By that logic, ideas are absolutely the important part. Which makes writers sound simply like scribes. I, myself, even thought that writing was about connecting the dots for a while.

Turns out, my form of creativity is more about interpretation than translation.

I don’t have to worry about running out of ideas to generate, translate, or curate because of how I move through the world. I don’t operate from a place of idea generation. Coming up with ideas isn’t impossible, but it’s not my strong suit. I’m an observer. Even when I’m engaging with life instead of spectating, as I’m sometimes prone to do, I pay attention to what’s happening. Then, I ask myself what I think about what I find. Sometimes it’s just documentation. Other times, it includes commentary. And I’m not saying I never generate, translate, or curate. I do. But I’ve come to understand that I’m an interpreter first. That’s my strong suit. And I’ve been doing it long enough by now to know that my mission isn’t to find a great idea and protect it like hell.

It’s to live the life in front of me and observe what happens in great detail.

That’s how I come up with endless things to write about.

It’s how I find stories to tell.

Our Daily MAP Year Prompt
316/365

Are you a generator, a translator, or a curator?

onward.

For more on this daily column and The MAP Year Project, read the backstory.

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This hill’s 1,000 feet and I’m at the bottom of it, making my way back up after reaching the midway point of my 8.5 mile run.

I’m trudging along and, so far, I’m feeling surprisingly good.

I like this route. It’s in the mountains near a ski area, but it’s less crowded than the resort’s main access road. The trees frame the road with vibrant green leaves and the sound of running water keeps my mind occupied. I’d initially been listening to the latest episode of the SOLVED podcast from Mark Manson, but I don’t have cell service here, and I forgot to download it, so it stopped playing a little bit ago. Just as well—I was going to pause it anyway.

As I was running, Mark and his co-host, Drew, were talking about the science of what we can actually change about ourselves and which stuff we simply can’t. That’s always fascinated me. And, for as much as I don’t want to like Mark, he’s making it difficult.

I’m whooped.

Still, I let out an audible “aghh fuckkkk” when he said “there’s understanding why you do something and then there’s changing it; but those are two separate things.”

My “running” right now feels more shuffling. It’s like I’m on the stair-master at the gym. I hate those. But, for whatever reason, I like this. Go figure. I’m moving, though, and that’s all I care about. I’m gasping for air while trying to control my breathing with four-count inhales and exhales. A car passes and I can’t even look at them or I’ll lose my focus. Spittles flying from the corner of my mouth. My chest is on fire. The counting is helping, though.

I’m even smirking, slightly, thinking of the strength and conditioning program we did for high school football, and how I’d spend all day in the sun working before driving my ass to the turf to run sprints three times a week. That was in addition to going on my own runs in the morning and going to the gym after work on the days when I wasn’t at the turf. I don’t know if the coaches thought they were being kind by ramping things up incrementally, but it only created dread for me. We’d start small (ish), before building to full-out, 100-yard sprints. Then, once we were exhausted, we’d finish with hill-sprints from the parking lot behind the gym. Plenty of us would throw up and I guess I just thought that was normal. Same with the coaches screaming in our faces to keep going.

My self-talk sounded like that for a long time until I realized it didn’t have to. For one thing, it’s proven that people respond better to praise than reprimands. But, also, I came to accept that I wasn’t moving though life at a deficit that needed to be made up. There’s a lot of stuff I like to do where improving is part of the fun. Take snowboarding for instance. Or writing. But living my day-to-day life doesn’t need to be rocket science. Working to get better can be enjoyable rather than belittling.

So as I’m inching my way along the guardrail, through a corridor of trees among the surrounding mountains, I’m wanting to hate Mark Manson and the self-help gurus out there for preying on people who are hurting—for unnecessarily playing the role of yelling football coach. But then he goes and says that thing about how understanding something and changing it are different. And he follows it up by adding how the industry is full of grifters who sell people “change” when what they mean is “understanding.”

And he’s right.

I crest one of the hills within this bigger hill and take some time to walk the straightaway and catch my breath. For now, I’m just focusing on breathing. There’s plenty that I understand about myself and still struggle to change. And I’m working on it.

I never stopped to consider whether it was a fool’s errand.

Our Daily MAP Year Prompt
315/365

Can you think of a time when understanding yourself was easier than changing?

onward.

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