Why Is This Not Working?!

~ David Willis ~ Leave a comment

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

~ David Willis ~ Leave a comment

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

~ David Willis ~ Leave a comment

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.

Whose Name Is On It?

~ David Willis ~ Leave a comment

I’ve spent close to twenty years in data, and a lot of that time on project work. Some of it high profile. On the ones I led, I wasn’t a manager — I was the technical subject matter expert, which meant I wasn’t responsible for anyone’s paycheck but I was responsible for the work packages going out the door.

That distinction matters less than it sounds like it should.

When everything runs clean, I look good. When it doesn’t, the people doing the work get looked at, and then everyone looks at me, because I’m the one who reviewed it. I’m the one who signed off. Multiple points of failure, one name at the bottom.

So when something got past me — when work went out and around before I could catch it — I didn’t just have a quality problem. I had damage control. Remediation. And then the harder part, which is sitting down with a person and having the conversation nobody wants to have, sometimes more than once, focused on solving the issue.

It always worked out. That’s not the point. The point is that I learned a long time ago that my name is the thing I’m actually trading on, and everything that goes out under it is a withdrawal or a deposit.

I’ve been telling myself I have a camera problem.

I don’t have a problem with my face being attached to things. I don’t have a problem standing in front of a room. I’ve given a lot of speeches to a lot of people and I like doing it. Put me on a stage and I’m fine.

So the anxiety around shooting video for the book has been confusing to me, right up until I put it next to the sign-off.

I’m old school enough that if I’m going to put something on video, I want to be saying something helpful and true — something I’d sign. And what I’ve noticed is that the videos come easy when I’m talking about the book. The characters, the writing process, why I made a choice. I can vouch for all of it. I wrote it. I know exactly what’s in there.

Where I freeze is the stuff where I haven’t finished the thinking yet. Where the message is still four-fifths formed and I can feel the soft spot in it. My mouth knows it before my head does.

That’s not fear of the lens. That’s my sign-off reflex firing correctly.

Which means I’ve been solving for the wrong thing. I kept trying to get comfortable on camera, and comfortable was never the variable. Vouchable was.

If I can’t stand behind it, I shouldn’t be the one selling it. If I want to be able to shoot the video, the work isn’t in the video — it’s upstream, in getting the message clear enough that I’d put my name at the bottom without flinching.

And I’ve been doing that for twenty years. Just not for myself.

There’s a version of this I don’t love admitting. Some of the videos I’ve avoided weren’t avoided because the message was unclear. They were avoided because clarifying it would have taken an afternoon I didn’t want to give it, and “I’m not comfortable on camera” is a much more flattering sentence than “I haven’t done the work yet.”

I signed off on a lot of other people’s work over the years and never once thought it was strange to be accountable for something I didn’t personally build.

The camera just asks the same question, pointed the other direction.

The Thing Became The Message

~ David Willis ~ Leave a comment

When I found Toastmasters I fell in love with it immediately. Not with speaking — with the machinery of speaking. Structure, delivery, the evaluation loop, the whole beautiful system of it.

There was one problem, and it took me years to see it.

I didn’t have anything to say.

So I did the natural thing. I talked about speaking. I gave speeches about how to give speeches. I helped other people get better at the thing I was getting better at, which is genuinely useful work and I’d do it again — but somewhere in there the vehicle quietly became the destination. I had picked up a tool for carrying a message and then spent years admiring the tool.

Same thing happened with Dan Miller.

I read 48 Days to the Work You Love, then No More Mondays, and they lit me up. Here was a framework for building something of my own. I wanted that badly.

I didn’t know how to apply it. So instead of starting the business, I wanted to talk about starting the business. I could explain his framework to you cleanly. I could not point at a thing I had built with it.

That’s twice now. There’s probably a third I haven’t caught.

The pattern goes like this: I get excited about something because I want to learn it, and instead of running my own material through it, I make the learning itself the whole enterprise. It feels like progress. It produces content. It even helps people. And it lets me stay one comfortable step back from the thing I actually have to say.

Which brings me to the obvious risk sitting in front of me right now.

I use AI something like eight hours a day. I have conversations with people who are still deciding whether it belongs in their business at all, and I’m not an early adopter by any stretch, but I’m clearly further down the road than most of the room I’m standing in. That gap is real and it won’t stay open long.

And the easiest possible move from here is: I learned AI, let me teach you AI.

That’s the trap. That’s Toastmasters again with new vocabulary.

Because AI isn’t my strength. I’ll say that plainly. My strength isn’t knowing how large language models work under the hood, and it isn’t prompting — I’m good at it, but so are a lot of people, and it’s getting easier by the month. My strength is taking something difficult to understand and making a person feel like they understand it. That’s what twenty years of technical work built, and it’s what Toastmasters sharpened, and it’s the only thing I’ve ever been consistently better at than the people around me.

So the message isn’t AI.

The message is communication. It always was — I just spent years talking about the delivery mechanism instead. AI is what makes the message urgent, because we’ve handed a huge portion of human communication to a machine and almost nobody was taught how to talk to it, and the ones who don’t learn are going to lose ground fast.

The tool is the reason people will listen. It isn’t the thing I’m saying.

I’ve caught this in myself twice. Both times, years late.

The tell is the same in every case: when I can teach the framework more fluently than I can show you what I made with it, I’ve swapped the vehicle for the road.