The Craving

It took two days.

Two days into assessment week — a planned break between rounds of the 7-40 Challenge — and I was already craving the structure I’d stepped away from.

I’ll admit, some of the break was good. I stopped listening to audiobooks for a few days and let my mind clear out. That turned out to be exactly what I needed to get ready for the next round of learning. And I never stopped my daily Bible reading. I just couldn’t let that one go.

But the calorie tracking slipped. The water slipped. I ate off plan multiple days, some just because I could — which, looking back, was kind of stupid. And it gave me a feeling I didn’t like. I could feel myself sliding back into habit patterns I don’t need. By day three I knew I had to pivot back.

So when I woke up this morning — Round 3, Day 1 — and I had my list in front of me, I felt relief. Energy. A little pep in my step. Because I had those small moments of accomplishment spread across the day again, and they’re fantastic.

Here’s why I think that matters beyond just me.

A long time ago, my grandfather was diagnosed with Alzheimer’s. He lived for several years after his diagnosis, but he did not do well in unfamiliar places or unfamiliar routines. My grandmother — a retired nurse and a bit of a drill sergeant — kept his framework together. She kept him in line, kept him moving, kept his daily structure strong. And he was able to function for years, even as he lost more and more of his memory, because his routines stayed the same.

There’s a whole different set of blog posts in that story. But the principle is the same one I felt this week.

Our brains crave habit patterns. They are actual physical things happening inside our heads. We expect the rewards they bring. We expect the satisfaction that comes with practicing them. And that’s true for good habits and bad habits alike. The dopamine high from a good workout isn’t that different from the dopamine hit of an addiction. The difference is which pattern you’ve seeded.

Where I feel grateful is this: I’m healthy. I’m more motivated this year than I’ve ever been in my life. I feel daunted and challenged by the work I’ve set in front of myself, which is probably a good thing. Keeping myself in these habits — keeping myself moving forward — is how I prime myself for success through the seasons when fatigue or exhaustion or grief would want to stop me.

My grandfather didn’t have a choice. His framework was held together by someone who loved him. I have the choice. And after two days without it, I know exactly what I’m choosing.

Go Deep

I ran a demo today. Asked AI a question in plain English. It wrote a SQL query in real time. I asked it to convert the output to R. Done. Less than a minute.

Three years ago that could have taken me a few hours. Minimum.

Everyone in the room was impressed, and I don’t blame them. It is impressive. But the part that mattered most isn’t the part that got the reaction.

The SQL it produced was good. It took the natural language prompt I gave it and created what I wanted. However, I still had to verify the SQL to make sure my demo was successful. I was able to do that because I have been doing this kind of work for almost twenty years. I didn’t have to look it up. I just knew.

And that’s the thing more people need to talk about.

AI is going to flatten surface-level knowledge. If all you bring to the table is the ability to do something the machine now does in thirty seconds, that’s a problem. But if you can evaluate whether what the machine produced is actually right — that’s a different conversation entirely.

I told the room: build your context architecture. Know every piece of your workflow. Know how the levers get pulled. Know what right looks like before you ask the machine to produce it. Because without that architecture, AI doesn’t help you. It just runs your bad assumptions faster.

The people who thrive through this won’t be the ones who learned the tool fastest. They’ll be the ones who went deep enough to know when the tool got it wrong.

I am thankful that I have had the last twenty years to learn the data. Today that investment is paying returns I didn’t expect.

Attack the Problem

Assessment Week 2 — Day 4 | The 7-40 Challenge

I took my mother to a hospital procedure this morning. My dad had a different appointment of his own, so I was the one taking her. My parents drove over two hours to get there. When we arrived, the hospital had her appointment time marked thirty minutes earlier than what the doctor’s office had given us. We were on time according to our paperwork. We were late according to theirs.

They told us she’d have to reschedule.

My mother is not getting any younger. She has health concerns she’s battling through. She didn’t need a bureaucratic answer this morning. She needed someone to see her as a person, not a scheduling conflict.

I was angry. I’m still angry, if I’m being honest.


But here’s what I want to talk about tonight.

When the check-in person delivered the news, I could see it on her face. She didn’t make this call. She didn’t create the miscommunication between the doctor’s office and the hospital. She was just the person sitting closest to the problem when it landed.

So I looked at her and said, “Ma’am, you’re doing a good job. I appreciate you. I know this was not you.”

Because it wasn’t. And she needed to hear that someone in the room knew the difference between the person and the problem.

I wanted to go upstairs. I wanted to find the office of whoever had been cold about the situation and professionally remind them that their decision had a cost — two hours of driving, a day of my mother’s time, a hundred and fifty dollars in gas and trouble, and a woman who needed care and didn’t get it. I wanted to give them a face to attach to the scheduling line they’d just dismissed.

My dad asked me not to.

So I didn’t.


There’s a version of me from ten years ago who would have gone anyway. Who would have justified it by calling it advocacy. Who would have been loud and felt righteous about it.

But my dad — who had his own appointment to deal with and still made sure his wife got to hers — asked me to let it go. And I listened. Not because he was right about the hospital. Because he was right about me. Going upstairs wasn’t going to get my mother her procedure today. It was going to make me feel better at the expense of making the situation worse.

You can be upset and not sin by making things worse than they are.

That’s the line I keep coming back to.


If my son had been sitting in that waiting room, I would have wanted him to see all of it. The anger — because it’s okay to be angry when someone you love gets treated like a number. The restraint — because the check-in person didn’t deserve to absorb what the system did. The distinction — because attacking the problem and attacking the person are two very different things, and most people never learn to separate them.

And the hardest part: knowing when someone you respect asks you to stand down, and having the discipline to listen. Not because the fight isn’t worth having. Because the person asking you to stop has earned the right to be heard.

My dad has earned that. Many times over.


Here’s what I’m sitting with tonight. I had agency in that room. I had the ability to make things louder, harder, uglier. I also had the ability to make one person’s day a little less terrible by telling her she was doing a good job when nobody else was going to.

Both of those were choices. Both of those were agency.

We talk a lot about agency as the power to act — to push, to build, to make things happen. But agency also means choosing compassion when you have every reason not to. It means seeing the person behind the counter as a human being caught in someone else’s mess. It means letting your father’s quiet request carry more weight than your own frustration.

The system failed my mother today. But I didn’t have to fail the people standing in front of me.

That’s what I’d want Trey to see. Not a father who swallowed his anger. A father who chose where to spend it.


Assessment Week 2 — Day 4. Some lessons don’t come from books. They come from waiting rooms.

Evidence of Creativity

Assessment Week 2 — Day 2 | The 7-40 Challenge

Some people would try to tell you that creativity is hard. That only certain people are creative, and only at certain times. Like creativity is this mystical thing sitting just beyond a veil — and that veil only opens for the fortunate few who know the wizard behind the curtain or get lucky.

I think creativity is something we use every day. To solve problems. To see things in new ways. To stay sane when everything else wants to drive us crazy.

Today, the family and I went on adventures. Mini golf. Go-karts. Ice cream. It was a really good day, and it was long overdue.

We also went to Barnes & Noble. I love a good bookstore. Not just because I want to buy everything on the shelves — though yes, partly that. It’s because I love looking around at evidence of the creativity of so many different people. Every book on that shelf represents months, if not years, of someone’s concentration and frustration and persistence. Just to get that book onto that shelf. I find it inspiring in ways I can’t fully explain. It makes me want to be creative myself.

Which leads me to the point.

While walking around the store today, I started brainstorming a new story idea. And while I struggled with new creative ideas for the longest time, something has changed since I started engaging my creative muscles every single day — either working on the ideas I already have, seeing old ideas in new ways, or just coming up with something brand new.

Things seem to come when I start talking to myself. I opened my voice-to-text and started asking questions. And what came out was a mashup of ideas that I don’t know if anybody has thought of before. Two very old stories, rearranged and combined into something completely new.

The idea itself isn’t the point of this post. I’ll work on it and share it another time.

The point is this: sometimes we think we have to create brand new things out of thin air. That’s just not the truth. Sometimes the most creative thing you can do is take two or three things that already exist and throw them at each other to see what sticks. Remix what’s already out there. Combine things nobody thought to combine.

I did that today, walking around a bookstore with no agenda, and I was pleasantly surprised at how quickly the ideas and the outline started coming together.

If you’ve got a creative endeavor you’re working on and you’re stuck — go someplace out of the norm. Look at things that seem completely unrelated to what you’re doing. Start thinking about how you could remix what already exists into something uniquely yours. How could you see what’s in front of you in a way nobody else has?

Think outside the box. I did it today.

And I was pleasantly surprised with the result.


Assessment Week 2 — Day 2. Mini golf, go-karts, ice cream, and a new story born in a bookstore. Rest looks different than I expected.

Cover Band

Day 79 | The 7-40 Challenge

I’m about to open a piece about not playing covers with a cover. I know. Stay with me.

Todd Henry makes a distinction between cover bands and original artists. A cover band can be really good — fill a room, play the songs people love, make decent money on a Friday night. But there’s always another cover band coming that plays those songs a little better. The ceiling is built in, because you’re performing someone else’s work. An original artist risks silence. Nobody claps when they don’t recognize the song. But the work is yours.

When we’re kids, we copy. That’s how we learn. We mimic behaviors, repeat patterns, try on other people’s styles. That’s development. But at some point, you’re supposed to stop covering and start writing your own songs. And I wonder how many of us are stuck at the toddler stage — still mimicking, not because we lack talent, but because originals are terrifying and covers are safe.

I spent twenty years covering. I read Donald Miller and started telling people about “living a good story.” I read Seth Godin and started talking about tribes and linchpins. I gave speeches using their ideas as scaffolding. I filled notebooks with goals that sounded like remixed versions of books I’d read. I was a really good cover band. But I was still playing other people’s songs.

The shift happened slowly, then caught me off guard. Somewhere after the second round of cancer, after years of sitting with ideas long enough to pressure-test them against my own life, I stopped quoting and started originating. Not because Miller and Godin stopped mattering — but because I’d finally lived enough to have something of my own to say.

I used to say “tell a good story with your life” because Donald Miller said it and it sounded right. Now I say “tell the stories of your life so they can help people” — because that’s what I actually believe, and it came from seventy-nine days of doing it in public, not from a book I read in 2008.

Right now, all I’m playing is originals. My blog gets ten to twelve views a day. Nobody is cheering loudly. I am an original artist playing to a small room, and I am staying on stage — not because the crowd is big, but because the music is mine.

And here’s the part I didn’t plan.

I sang in an eighth-grade show choir because I was copying what seemed fun. I joined high school choir because I was mimicking kids who seemed like they belonged. I earned a music scholarship because I practiced something I’d started by imitation. And that scholarship put me in the exact place where I met the woman I’ve been married to for twenty-seven years.

Following something genuinely mine — not someone else’s career path, not someone else’s definition of success, just a voice I was learning to use — led me to the most important person in my life. I couldn’t have planned that. Originals take you places covers never could. You just can’t see the destination from the stage.


Day 79 of 280. One day left in Round 2.