GarthBox

Someone broke a glass in the hotel pool.

Not near the pool. In it. Most of the guests were annoyed about toweling off early. I was doing a different math. You cannot see glass in water, and you cannot vacuum what you cannot see, so depending on the hotel’s appetite for risk, that pool might get drained. Thousands of gallons and somebody’s whole night, because one person let their kiddos bring a glass toy into the pool.

I have never worked at a hotel pool. But I have stood over an ice bin.

Behind a bar there is a ranking of where glass can break, and every bartender knows it by heart. The floor is nothing: broom, thirty seconds, a joke about tipping the bar gods. The glasswasher is worse: shards hiding in hot soapy water, every glass in the rack washed again, your hands moving slow and suspicious for the rest of the shift. But the ice bin is the one that hollows you out. You cannot pick glass out of ice. You cannot even be sure how far it traveled. So you burn the whole bin. Melt it, dump it, all of it down the drain, then start over while the tickets stack up.

The pool crew and I have never done each other’s jobs. I still knew exactly what their night had just become, because my own small disasters had taught me the shape of theirs.

That is the thing about empathy I think we get backwards. We treat it like it runs on experience, like you can only truly feel for someone if you have lived their exact version. But nobody gets enough lifetimes for that. You get one bar, one career, one family, one body. Everything else you will ever understand about people, you will have to get by watching.

And watching is a skill you can aim. We already observe constantly. We just aim it at the wrong things: outfits, cars, typos, who got the promotion.

Aim it at hardship instead.

The barista counting her drawer twice. The contractor redoing drywall on his own dime. The manager apologizing for a decision made two levels above her. Two things happen when you do. Your own hard days stop feeling like solitary confinement, because you have seen the same weather over everyone else’s house. And grace gets easier, because you have watched what people are actually carrying.

This is also the quiet trick of anyone good at marketing, or at leading. You will never be your customer. You will never live your employee’s Tuesday. The people who seem psychic about what an audience needs were almost never members of the audience. They are watchers. They know where the glass tends to break in other people’s lives, and they build for it.

I grew up on “give them the benefit of the doubt.” It is a decent motto, but it is a courtroom motto. It withholds a verdict. It hands nobody anything.

New motto: give them all the empathy. Not a measured amount. Not what their behavior earned. All of it. The crew fishing a pool for glass that night did not need my reserved judgment. They needed one person on that wet deck who looked at them like someone staring into an ice bin.

Stay Positive & Watch For The Glass

I looked at my to-do list this week and realized I had built myself a very nice place to hide.

Everything on it was real work. Follow-ups, edits, scheduling, a handful of small fixes. All of it legitimate. All of it checkable. None of it the thing.

That’s the trouble with tasks. A task can be finished. A mission? Not so much. Checking a box pays you immediately, a little hit of progress right there in the moment. A mission pays in months, maybe, and only if you were right. So given the choice, and we are given the choice every single morning, we reach for the boxes. Not because we’re lazy. Because we’re hiding, and a full list is excellent camouflage.

The costume works in the other direction too. Stack enough tasks on top of each other, give the pile a project name, and it starts to look like a mission.

I know because I’ve sewn that costume myself before.

At a previous gig I ran a go-to-market motion I was proud of at the time. It had everything a launch is supposed to have. Sequenced emails. A one-pager. Enablement. A checklist that got checked all the way down. It felt like momentum, and momentum is a very convincing feeling.

What that motion never had was the question underneath it: is this even the feature worth this much of us?

In hindsight, the answer was no. The time belonged to a different feature entirely, and to a much more drastic prioritization of the actual initiatives instead of the tasks orbiting the first one. We executed beautifully on the wrong bet. Nobody noticed, because every box was checked, and checked boxes are what reviews are made of. (Thankfully it was one of our most successful releases, but I knew I could point the success to only a couple checked boxes; not all of them.)

Stay Positive & Tasks Are Receipts; Missions Are Bets

For a stretch, I spent my off hours driving to local game shops. Board game shops, card shops, anywhere with dice behind the counter. Not to buy anything. To pitch. I wanted them to partner with us on events like a Dungeons and Dragons night at the bar.

A beer bar. A place whose entire identity was the tap list. We had spent years going deep on exactly one thing, and there I was asking a guy restocking miniatures if he wanted to help me host a campaign between the taps.

The standard advice says I should have stayed home. Focus on the core. Protect the thing you’re known for. It’s the most repeated strategy note in business, and it’s incomplete in a way that doesn’t show up on any invoice until later.

Depth creates an obligation, though.

When customers go deep with you, they do not want deeper and then deeper again. Nobody buys single depth. They show up to have their expectations met, then exceeded, and exceeded eventually means surprised. The deeper your core gets, the wider your customers expect you to reach.

You don’t get to opt out of that expectation. You only get to decide whether you’ll meet it on purpose or disappoint it by accident.

Here’s the mechanism…. The core’s actual job is to de-risk the weird stuff.

The aquarium in Denver will let you climb into a cage while sharks glide past your face. That’s an unhinged product, and it sells, because the rest of the building is the safest place in the city. Avanti works the same way: enough variety to pique you, something new and something safe under the same roof. The safe thing is not the opposite of the new thing. The safe thing is what makes the new thing purchasable.

D&D night worked at the bar for the same reason. If the dice bored you, the beer didn’t. Nobody was betting their whole evening on a twenty-sided die. The tap list was the net under the trapeze. And the game shops got the mirror image: their regulars walked into a bar that had already been vouched for by the hobby they trusted.

The trap, and the reason I say obligation instead of opportunity… the safety you build is exactly the thing that obligates you.

Once people trust the roof, they start expecting you to put new things under it….That’s the bill for loyalty. Depth is a debt, and your customers collect it in surprise.

Which also explains why some experiments make everyone wince. When a company known for one thing ships a basketball, a speaker that follows you around the room, and a meme generator, the reflex is to call it unfocused. (I’m talking about Open.AI if you couldn’t guess.) I don’t think that’s the diagnosis. It’s unearned width. The core hadn’t gone deep enough to make those bets feel safe, so instead of surprise, customers felt confusion.

Same move, different balance sheet.

The question was never whether to stay focused…The question is whether you’ve gone deep enough that your customers are quietly waiting for you to do something strange.

Stay Positive & If Nobody’s Waiting, The Weird Thing Isn’t Your Problem…The Core Is

There’s a brewery called Mountain Sun and I can tell you its name because a waiter there decided, without asking my permission, that I would remember it for the rest of my life.

He talked about the beer the way some people talk about a first car or a last dance. Not a script. Not the upsell voice. He knew which tank it came out of and he had opinions about it, actual opinions, the kind you can only form by caring past the point where your paycheck stops requiring it. I don’t remember what I ordered after the saison. I remember him. The brewery gets to live in my head rent-free, forever, because one human being on its payroll meant it.

That same trip, I bought a coffee somewhere.

I know this only by residue, the way you know you had a dream. I cannot tell you the shop’s name. I cannot tell you the street, the cup, or whether the person behind the counter was one human or a rotation of three. I remember a pink banner. That’s all. The coffee was fine. Fine is the sound memory makes while it’s deleting something.

So here’s what I’ve come to believe. Every customer walks through your door wearing a give-a-damn meter. Standard equipment, factory installed, mounted somewhere between the sternum and the gut, no off switch, no snooze. It does not measure quality. Quality gets you to fine, and you now know what fine is worth. The meter measures one thing: whether a human on the other end meant it.

And the readout isn’t stars or reviews or net promoter anything.

The readout is memory.

You exist in a customer’s life exactly as long as the needle moved, and not one minute longer.

You can’t bribe the instrument. Fonts don’t move it. Mission statements painted on reclaimed wood don’t move it. It is the most honest gauge in all of commerce, and it responds only to meant things.

Which is why you should strap one on yourself, facing backward, pointed at your own work. Before anything ships, check it: did my needle move while I made this? Because care survives translation into the finished thing, and so does boredom. If you were checked out while making it, the checked-out is in there, load-bearing.

One more thing about that waiter. People who give a damn at work are, almost always, people somebody gave a damn about first. Needles are contagious. They catch from the inside of a company outward, never the reverse.

Stay Positive & Order Whatever Makes The Waiter’s Eyes Light Up

I was on a beach in Colorado today, which is a sentence that requires a little faith. The state is landlocked, but nobody told the reservoir. My girls were in the water. I was on a rock at the edge of it, reading The Solitary Gourmet, a book about a man whose entire gift is paying attention to the meal in front of him.

And a sentence started loading in my mouth: five more minutes, girls, then we need to get to the next thing.

Nothing was wrong. Nobody was cold or hungry or bleeding. The water was doing what water does and the girls were doing what girls do in water.

The only thing pushing us toward the parking lot was the itinerary, and the itinerary was written by a version of me who wasn’t there. Some earlier Garth at a kitchen table, guessing at what a good day would look like, with no idea that the actual good day would involve a rock and a book about a man eating pork cutlets with total devotion.

I swallowed the sentence and kept reading.

I did the same thing at work the other week. I finished building an AI system, and the second it worked, the itch showed up: build the next one.

The itch felt like ambition. It dressed like ambition. But when I sat with it, it was closer to escape.

Starting something new is easier than asking whether the thing in front of you is finished or just functional. So instead of a new system, I invested the time adding small moments of surprise and delight to the one that already existed. Touches nobody asked for. The kind of thing you only add when you stay. It’s what actually made the system feel like it was made by me and not made by…well, anyone else.

Companies run this play constantly. Ship the feature, launch the campaign, hit the milestone, then immediately yell five more minutes at everything and sprint to the next roadmap item. New launches get applause. Deepening doesn’t. But your customers don’t live in your roadmap. They live in the thing you already shipped, today, the way my girls lived in that water. The roadmap was written by people in a conference room guessing at a future. The moment in front of you has actual people standing in it.

More is the default answer to what’s next. Deeper is the rarer one.

The man in the book never rushes a meal. He orders, he waits, he eats, and the entire drama is whether he’ll pay attention. It shouldn’t be gripping. It is. So it is in our life. If we let it.

Stay Positive & Five More Minutes

Desire is a door-to-door salesman who never rings the bell. It lets itself in, and it usually arrives wearing the voice of someone you love.

We almost bought a new couch this spring. Nothing was wrong with ours. It hadn’t sagged, hadn’t squeaked, hadn’t committed any of the crimes couches get replaced for. What happened was that a couple of family members mentioned, separately and casually, that they’d gotten new couches.

Two sentences, delivered as innocently as weather reports. Within a week we were saying things like “maybe we should look.”

So I sat down on the accused and asked it the only question that matters. Why do we have this couch?

The couch, being a couch, said nothing. But the answer stood up anyway. It is still doing the exact job we hired it to do, holding the exact people it was bought to hold. The chain closed in one link. We kept the couch, and I got to feel briefly like an enlightened man who floats above wanting things, a feeling with the approximate shelf life of a banana detached from its family.

Enough is not a trophy you mount over the fireplace and dust twice a year. Enough is a question with a decay rate. You answer it, the answer sits there quietly losing charge like a flashlight in a junk drawer, and then fate deals you a card and you have to answer the whole thing again.

My card came as a job offer. More money than I make now. The kind of money that shows up wearing cologne and pulling out your chair. And I had to ask the same dumb question about something much bigger than furniture. Why do I have this job?

I asked it again. And again. The chain refused to close at the salary line. It closed at the shape of my days. I’m home when I want to be home. My work bends around my family instead of my family bending around my work. That’s the why, and the why doesn’t take a raise. So I said no to the bigger number, and it wasn’t noble. It was arithmetic on a question I usually quit asking one why too early.

Now the confession. I make temptation cards for a living.

I’m a marketer. Strip the paint off the whole profession and what’s underneath is a thumb resting gently on the scale of your why. Every ad ever made is engineered to end your chain early, at “because it’s newer” or “because you deserve it” or “because everyone else already did.”

But notice what actually got me. It wasn’t an ad. No brand laid a finger on me. It was family, mentioning couches. Word of mouth is the most effective channel in marketing precisely because it never looks like marketing. Your defenses are calibrated for billboards, sirens, men in sandwich boards.

Then want slips past security disguised as small talk, holding a paper plate.

Which is why the counter-move can’t be avoiding temptation. You can’t unsubscribe from your relatives.

The counter-move is asking why until the chain actually closes. Not until you’re tired.

Those are different endings, and from the inside they feel nearly identical. Fatigue stops at “I don’t know, I guess it’s fine.” Closure stops at an answer you’d defend out loud, in front of witnesses.

The couch closed. The job closed. Plenty of other things in my house, I suspect, would not survive the questioning, which is probably why I haven’t asked them yet.

That’s the exhausting part, and I won’t pretend otherwise. The work never stays done. You will answer the question perfectly, your brain will lose the receipt, and somewhere a relative is already shopping for who-knows-what-next.

Stay Positive & Ask Me Again Next Month

Last month I turned a robot loose on the bars of Wisconsin to ask a single question: how much are you charging for Spotted Cow?

There was no business case for this. I run a brew bar. I visit bars. I already know what Spotted Cow costs. I built a conversational AI that could dial a bar, sit through the ringing, chat with whoever picked up, and log the number, purely because the idea made me laugh at my desk. (I saw someone do it for Guinness in Ireland and got inspired.)

That is the whole method of differentiating advantages in work, life, love, etc.,. But let me back up.

When I started with AI, I made one mental move that changed everything after it. I decided to treat it the way I treat Crimson Desert. I run multiple characters. I take the snackable missions. I grind the repetitive stuff without resenting it, because grinding is part of the game. I told myself I was going to enjoy every element of the journey, including the boring ones, and I stopped watching the meter. Nobody calculates the cost-per-hour of a game they love. (130 hours into Crimson Desert because my PS5 tells me, but I’ve got no clue how many I’ve put into Claude…far more, that’s for sure.)

Meanwhile, a lot of the smartest people I know were treating AI like a forklift. Efficiency. Career advantage. Prompts as productivity. They got exactly what they optimized for: slightly faster versions of the errands they already ran.

The side quests are where you find the sword.

While I was building a voice line to answer FAQ calls for the bar, the good idea arrived without an appointment: what if the calls went the other direction? A robot calls you, offers one cool beer fact to brighten your day, and wants nothing. No booking link. No survey. No strings.

Every call a business makes to you wants something back. A call that only gives might be the strangest call you get all year. It’s not quite the same as receiving a check in the mail, but it’s close! You would tell somebody about it. I cannot buy that with an ad budget, and no efficiency roadmap on earth would have produced it. Roadmaps improve the errands you already run.

I don’t believe anyone can treat this technology like a video game for six months and come out empty-handed. Play generates its own proof.

And this game does something no other game I own does. It patches itself while you sleep. Every few months (weeks? days? hours?!) the engine upgrades, and you can walk back through your old save files and watch them level up. Work I finished last winter runs better today than the day I shipped it. I’m not sure much else in my life works that way. The bar floor does not re-mop itself better each quarter.

The strange accounting of all this is that I went looking for fun and came back with an advantage. Every time I went looking for the advantage directly, I came back with a subscription and a headache…frustration..rage quitting.

So, one cool beer fact, no strings attached: New Glarus refuses to sell Spotted Cow outside Wisconsin, and bars across the border have been caught smuggling kegs of it. The beer’s best marketing is the state line.

Stay Positive & The Next Round Is On Me