Why Is This Not Working?!

Not long ago I got into a technical conversation with a guy at work, and I was dead certain I was right. Certain he was being short-sighted. Certain he wasn’t really hearing what I was saying.

He wasn’t hearing me. But not for the reason I assumed. I hadn’t framed my thinking well enough for a man with his expertise to even know what I was talking about. So I kept working at it, kept reframing, until finally he looked at me and said:

“I understand what you’re saying now. And you’re wrong.”

That’s a moment. You get about half a second to decide who you’re going to be in it.

I told him he’d done this more than I had, and asked him to tell me why I was wrong.

He did. And I was.

I don’t tell that story because I came out looking good. I tell it because I almost didn’t ask. The frustrated version of me walks out of that conversation still convinced, still wrong, and now also annoyed at him for it.


Here’s what I’ve come to notice about myself: when I stop being curious, I get grumpy. Every single time. It’s so consistent it’s basically a diagnostic. If I’m short with people, if I’ve gone quiet at the table, if my wife is wondering why I’m being moody — nine times out of ten it’s because somewhere in the last hour I quit asking questions and started defending a position.

It happens everywhere. It happened this week with a piece of software, of all things. I brought it an idea I was sure about, it poked reasonable holes in the idea, and instead of getting curious about where my thinking had gone sideways I got frustrated and shut down. At a computer. Doing exactly what I’d asked it to do.

The trigger changes. The tell never does.


There’s a question I ask right before I give up on something. It sounds like this:

Why is this not working? This should work. I know what I’m doing.

Look at everything packed in there. It isn’t really a question. It’s a complaint with a question mark stapled to the end. It presupposes the plan was sound, the variables are accounted for, my understanding is complete, and the universe is simply being uncooperative today. There’s no door in that question. It’s a wall with a “why” painted on it.

The question that actually gets me moving again is smaller and a lot less flattering:

What am I not thinking of?

What did I miss. How could I look at this differently. Who has this answer even though I don’t. Same problem, completely different posture. The first question protects my ego. The second one is willing to trade it for a solution.

That’s the whole difference. Not intelligence. Not effort. Posture.


I’ve been treating curiosity like a technique, and I don’t think that’s what it is.

If I’m in a disagreement with somebody, I still owe them the respect a person is owed. Not because they’ve earned it in the argument — because that’s how I’d want to be handled when I’m the one who’s wrong. And I have been the one who’s wrong plenty of times.

Do unto others as you would have them do unto you. There’s no exception clause for when you happen to be right.

Curiosity is what love looks like in the middle of a disagreement. It’s the practical form of it. Asking a real question and then actually waiting for the answer tells a person: you matter here, and I’m not done learning who you are.


Curiosity is not a personality type some people got issued at birth. It’s a choice you make daily, and it’s one you can forget to make.

You’ll know you forgot, because you’ll be irritable about it.

The Margins On The Page

Years ago I sat down with someone I love who was burning out and couldn’t hear it from anyone.

I pulled out a sheet of notebook paper. The standard kind — blue lines, red margin rule down the left, another one across the top. Everybody who went through American school knows that page.

I started writing her life into it. Work. The commitments. The people she was carrying. The things she’d said yes to because saying no felt unkind. We filled the lined part of the page and she kept going, so I kept writing — out past the red rule, into the margin, up into the header space, around the edges until there was no white left anywhere on the sheet.

Then I turned it around so she could look at it.

I didn’t have to explain it. You can’t read a page like that. Your eye has nowhere to land. It isn’t that burnout was coming for her — it was that burnout was already there and had been for a while, and the page was just the first place she’d seen it from outside her own head.

That was one of the more useful things I’ve ever done for another person.

I have never once drawn my own page.


Here’s the thing I’ve gotten wrong for most of my life, and I only recently found language for it.

I thought the opposite of busy was rest. So when I got tired, I stopped working. I’d sit down, put something on, scroll a while, watch a game. And I’d get up an hour later feeling exactly as full as when I sat down.

Because I hadn’t been quiet. I’d only been still on the outside.

Whatever’s on that screen is competing for the same resources the work was using. It’s a different tenant in the same room. Doing nothing and going quiet aren’t synonyms — they’re closer to opposites, and I spent twenty years using one and wondering why I never got the effects of the other.

There’s a real physical thing underneath it. When you stop deliberately doing something, a network in your brain takes over — the default mode network — and it runs self-referential chatter, mind-wandering, replays of the past and rehearsals of the future. That’s your idle state. That’s what “relaxing” actually gets you. Quiet is a different activity, and it takes work: you’re actively damping that chatter, and the regulatory part of your brain has to engage to do it.

Which means stillness isn’t the absence of effort. It’s a thing you have to go do.


I’m not good at going to do it.

Every time I consider being quiet, there is an open item on a list somewhere, and my brain produces it immediately and with excellent timing. That’s still sitting there. And the feeling that follows is a strange hybrid — part responsibility, like a grown man ought to handle his business, and part failure, like someone’s counting on me and I’m choosing not to.

For a long time I assumed the fix was to finish the list. Get to the bottom of it and then rest would be permitted.

I know better now, because I’ve gotten to the bottom of it. Twice, maybe. And what happens when you get there is that your brain, with no drama at all, hands you the next thing.

The list is infinite. It has always been infinite. So if the condition for rest is completion, then rest never legally arrives, and I’ve built a life where the permission slip can’t be issued.


Sabbath is the oldest answer to this and I’ve been reading past it my whole life.

It’s not scheduled after the work is finished. That’s the entire point. It arrives on the calendar whether or not you got through your week, and it arrives with a command attached, which tells you God knew exactly how we’d handle it if it were optional.

And it isn’t only weekly. Jesus withdrew to quiet places while there were still sick people in the crowd — which is to say there was an open item on the list, a big one, an unambiguously good one, and He went anyway.

That’s the part that undoes me. I could probably defend leaving the yard unmowed. I don’t know how to defend that.

So the small ones count too. Ten minutes in a chair with a timer, breathing, and when the mind wanders — and it will, that’s not failure, that’s the actual exercise — you notice and come back. Micro-Sabbath. The rhythm at a scale that fits inside a Tuesday.


Here’s what I haven’t figured out.

The 7-40 Challenge is seven habits, tracked daily, and every one of them is something I do. The whole system runs on accomplishment. It’s been good for me in ways I can measure.

But I built a machine for producing completed items and then went looking for the reason I can’t stop. I have some suspicions about where to look.

I don’t know yet whether stillness belongs inside that system as an eighth thing to check off, or whether checking it off would kill the only part of it that matters.

Either way I know what the page looks like. I drew one for somebody else and never turned the pen around.

I Only Rearrange

God spoke into a void and something was there.

That’s the first thing the Bible tells you about Him. Before the law, before the judgment, before any of the Renaissance paintings that shaped how most of us picture Him — the first fact on the record is that He made things.

I never noticed that until somebody pointed it out to me a little while back, and I haven’t been able to put it down since.

Because whatever I do when I sit down to write, it isn’t that.


I’m not pulling from nothing. I’m pulling from forty-seven years of everything I’ve read and watched and overheard and lived through, and I’m taking those pieces and putting them in an order they haven’t been in before. What I start with isn’t chaos exactly. It’s just not arranged the way it could be yet.

That’s the whole job. Rearranging.

Made in His image, not equal to it. He creates. I organize what He already made and hand it back slightly differently.

And every story I’ll ever tell has been told for thousands of years anyway — redemption, loss, somebody getting up off the floor when they had no business getting up. I’m not inventing those. I’m setting them somewhere new, in a voice that hits a little differently, so somebody hears the old thing for the first time.

That used to sound like a limitation to me. It doesn’t anymore.


Since I was a teenager I wanted to write songs. Not perform them — there’s a line in The Wedding Singer where Robbie says he never wanted to be a rock star, he just wanted to write the song that makes somebody go man, I know exactly what that guy was thinking. That’s been it for me since before I could have told you why.

I’ve since found out that’s what all of it is. The books, the pictures, the posts, the songs I finally did write. Every one of them is an attempt to arrange existing material so precisely that somebody else recognizes their own insides in it.

If being creative is what I was built to reflect, then doing it is a form of praise. Not because the output is any good — most of mine isn’t, and the pieces that are took twelve passes — but because wanting to return my creativity to Him is the point, to honor Him with the gifts He has given me.

I’ve been around people whose creativity flattened me. Watching what they can do with the same raw materials everybody else has access to is awesome inspiring to say the least. And to think their best is still just a poor reflection of THE Creative.


Here’s the part that keeps unsettling me.

If the first thing God tells us about Himself is that He creates, and that’s not the first thing I think of when I think about Him, then I’ve been carrying around a picture that isn’t accurate. And I doubt it stops there. What else have I absorbed about God from a painting or a sermon or a bad year that never got checked against the actual text?

Because if I’ve got wrong ideas about God, I’ve almost certainly got wrong ideas about myself. The two aren’t separable. How I see Him is upstream of how I see what I’m for.

For most of my life I treated the wanting-to-make-things part as a hobby that pulled me away from more serious business. Something to get to after the real work.

Turns out it might be the part that looks the most like Him.

Hold the Thread

If my past self walked in and watched me work now, he’d think I’d lost my mind.

On a normal afternoon I’ve got three or four conversations with AI running at once, each one chewing on a different problem. While they work, I’m answering email, checking back with people I owe an answer, reviewing something else entirely. Then a result comes back on the first window, so I dig into that, set it running again, and swing over to the third. By the end of the day I’ve moved a ridiculous amount of work forward, and at no point did I sit still and do one thing.

The old me would have called that scattered — undisciplined, context-switching myself into a fog. Because my whole picture of focus used to be singular: one task, everything else closed, head down until it was done. If I had a real problem to think through, I had to clear the desk to think at all. Anything that looked like today would have read as chaos to me — and honestly, back then it probably would have been chaos, because I didn’t yet know how to be anything but scattered.

Here’s what actually changed, and it isn’t the switching. I still bounce between things all day. What changed is that I can now hold the problem statement of every open thread at once. I know exactly what each window is trying to solve. I can set one running, work another, and pick the first back up without losing my place, because the place never left my head. That’s the whole difference between pipelining and flailing — not whether you’re jumping around, but whether you still know what each thing is for when you come back to it.

Same behavior. Opposite states. The line between them was never visible from the outside, and I couldn’t see it from the inside either, until I’d lived on both sides of it.

I want to be honest about the trap in this, though, because it’s a real one. “Productive fragmentation” is also exactly what avoidance looks like. Staying busy across six windows is a fantastic way to feel like you’re working while you dodge the one hard thing. So how do I know I’m not just fooling myself with a nicer word for scattered? One test: things are actually finishing. The board is clearing. Tasks are getting closed, not only juggled. If the pudding’s got no proof in it, I’m not pipelining — I’m hiding.

And there’s a harder honesty under that. This way of working isn’t an upgrade you can hand to anyone. It only works if you already know what you’re doing. If you’re organized underneath, the tool lets you run four threads instead of one. If you’re lost underneath, it just lets you be lost in four places at once.

So I’ve stopped believing “focused” and “scattered” describe how a desk looks. They describe whether the person sitting at it knows what they’re trying to do. Some people genuinely need one thing at a time to keep that clear, and there’s not one ounce of shame in it — that was me for most of my life. The only thing that changed is that I finally learned to hold more than one thread without dropping any of them.

The Room That Knew What I Knew

I found an old Toastmasters competition video of myself the other night. Watching old video of myself is its own small torture — you’re looking at a former version, and you can see everything he doesn’t know yet. It’s like watching a younger sibling do the thing. But I’ll say it plainly: it was a good speech. I was proud of it then and I’m proud of it now.

The speech was about my time writing for the college paper. I’d been assigned to cover a speaker one night, and I had the audacity to bring a date and cut out early, before the man even took the stage. The next day I told my professor there wasn’t a story there. She looked at me like I was an idiot — which I was — because the man I hadn’t stayed to hear was a rescue worker from the Oklahoma City bombing. So I went and found him. I learned his story. And somewhere in there I realized he was telling a very good story with his life, and I wasn’t telling much of one at all.

I knew that speech was special because I could feel the room respond when I gave it. And still I ran it, over and over, in front of people who knew the material as well as I did.

That’s the part that seems strange from the outside. I wasn’t in that room to learn what makes a speech work. I could have recited the criteria — vocal variety, gesture, stage use, the scoring rubric, all of it. Everyone in that room could have. And that’s exactly why it worked. There’s a wide gap between knowing the academics of a thing and putting them into practice while you’re standing up there, and nobody can see across that gap from the inside.

Because here’s what a blind spot actually is. It isn’t ignorance. It’s what happens when you’ve rehearsed something so many times it’s dropped into muscle memory — and the very repetition that makes it effortless is what makes the flaw invisible. You’ve done it a hundred times. It feels right. It has to be right. Then somebody who’s watched a thousand speeches tells you you’re repeating a word, or your gesture is overplayed and pulling attention off the line it’s supposed to carry, and you realize you’ve been doing it every single run and you never once saw it. The room wasn’t teaching me anything I didn’t know. The room was seeing me.

I made the district finals with that speech. I don’t believe I get there without those people — not without the corrections, not without the energy they gave me, not without being sanded down enough times to be genuinely polished instead of merely talented. I’ve competed since. I’ve never gotten that far again, and I know exactly why: I’ve never worked that hard again.

But the room isn’t magic, and I want to be honest about that, because I’ve been on the other end of it too. A different competition, a loss I didn’t think I deserved, and a man I’d never met walked up as I came off the stage and asked if he could give me feedback. I wanted to punch him. Not because he was wrong — I don’t even remember if he was wrong. Because he cared more about the method than about me. He wanted to stand on his knowledge for a second. That’s not sharpening. That’s the difference between a supportive community and a religion, and the feedback is identical in both. What changes is whether the person is for you.

And there’s one more thing, which I only saw watching that old video back.

The speech made it about me. I was so busy connecting his story to my own that I never finished it through his eyes — and it’s less powerful for it. It’s a smaller speech than it should have been, and the man deserved better than to be the setup for my lesson.

Nobody in that room ever told me. They couldn’t. Not because they weren’t good enough, but because I gave them a speech I’d already decided was mine, and they helped me deliver the speech I brought them. The room can only sharpen the blade you hand it.