Stop

~ David Willis ~ Leave a comment

Assessment Week 2 — Day 1 | The 7-40 Challenge

I find it really funny that after eighty days of building habits, publishing a novel, creating frameworks, and writing every single day — the first thing I thought this morning was: All right, what’s my list?

What do I have to do? How do I get into assessment mode? How do I go, go, go?

And from somewhere deep inside me, everything said: Stop.

Not stop the challenge. Not stop everything I’m doing. But stop moving long enough to actually rest. Because I can’t assess anything if I’m frazzled. I can’t re-examine what matters if I’m still wired to perform.

So today, I didn’t exercise. I didn’t read. I ate off my plan. And honestly? It all felt really good.

In some regards, I’m frustrated with myself. It feels like I should be doing more. It feels like I should be working on the things I work on all the time. But I’m learning that rest — and even a little bit of goofing off — is what my mind and body are calling for right now.

That’s a hard thing to accept when you’ve spent eighty days proving to yourself that you can show up every day. The voice that got you out of bed and onto the road doesn’t just shut off because the calendar says it’s assessment week. It wants to keep going. And part of growing is knowing when to tell that voice: Not today. Today we rest.

I’m still documenting. I’m still asking questions. I’m still on the journey. But tonight, I’m going to bed early. I’m probably going to sleep late in the morning. I’m going to take my family to go play mini golf. And it’s going to be a chill weekend.

I’m really looking forward to it.

Assessment Week 2 — Day 1. Rest is not retreat. It’s part of the design.

Framework and Freedom

~ David Willis ~ Leave a comment

Day 80 of 280 | The 7-40 Challenge

Round 2 is done.

Forty more days. All seven habits. Two full rounds in the books. And I want to talk about something that I keep coming back to — the relationship between structure and freedom, and why most people have it backwards.

When I started the 7-40 Challenge on January 1st, I knew the fundamental things I needed to do. Bible study. Exercise. Calorie tracking. Water. Reading. Gratitude. Intentional creativity every day. That was framework number one. Because if I don’t do those things, I don’t have the structure in place to do anything else.

The more I do them, the more automatic they become. Some days I nail them. Some days I don’t do so great. But the framework is there. And if I hadn’t established it early — if I had skipped straight to the exciting stuff, the publishing, the platform building, the strategy documents — everything would have cratered.

Instead, the framework held. And because it held, I was able to build on top of it.

Here’s what I didn’t expect about Round 2: the sheer volume of what the framework made possible.

Not just the habits themselves, but the infrastructure that grew out of them. Strategy documents. Operational systems. A content pipeline. Frameworks for how I think about writing, publishing, communication, personal transformation — each one fitting inside a larger structure.

And people might hear that and think — isn’t that overwhelming?

The answer is: I get overwhelmed when I stop putting things in their proper place. When I stop naming things, stop organizing, stop relating one piece to another. That’s when the wheels come off — because then I feel like I have to hold everything in my head, and nobody can do that.

I’ve worked in data management for eighteen years. Here’s the clearest way I can explain it: in a well-built data model, you’ve got tables with foreign keys that relate to each other naturally. Everything flows. But if you’ve got some weird orphan structure that you’re just trying to park somewhere — that’s where your junk data comes from. Same thing in life. A sub-framework that fits naturally inside a larger structure adds value. One that doesn’t just creates overhead. And overhead kills momentum.

The biggest unlock, though, wasn’t the organization. It was discovering how I actually think.

I’ve always had ideas. That was never the problem. The problem was getting them out of my head and into a form where I could retrieve them and build on them. Typing is brutal. Handwriting is worse. And I think out loud — I process by talking. Twenty years of Toastmasters trained me to deliver ideas extemporaneously, but I never connected that skill to a capture system.

Then I started using voice-to-text as my primary writing method. And everything changed.

I wrote a novel by talking into my iPhone.

That sentence still sounds insane to me. But it happened. Because I finally matched my output method to the way my brain actually works, and then I used an AI tool to help me organize, categorize, and pressure-test what I’d said. The ideas were always there. I just didn’t have the infrastructure to catch them.

So here’s where I want to land, because this is the thing I keep circling back to.

Structure and freedom are not opposites. They’re partners.

Think about driving. If I decide to be “free” and drive my car anywhere — across ditches, through yards, against traffic — sure, that’s freedom in the loosest sense. But it’s going to get me stuck. It’s going to cost me a tow truck. It’s going to put me in bondage to consequences I created because I wouldn’t work within any structure at all.

Real freedom on the road is driving down roads I’ve never been down before. Exploring. Discovering. But on actual roads. With lanes and signs and a general sense of direction.

Same thing with the habits. How do I get freedom by exercising every day? How is limiting my calories freeing? Because I’m giving myself the freedom to not be overweight. The freedom to not have my joints ache. The freedom to be healthy enough to play with my kid and chase my goals and show up for the people I love.

I used to think creativity meant waiting for the moment to hit. That one day inspiration would show up and I’d write the book, record the song, build the thing. I waited years for that moment. It never came. What came instead was a commitment to sit down — or in my case, walk and talk — every single day at the same time, whether I felt creative or not. The novel didn’t come from a lightning strike. It came from eighty consecutive days of showing up. Structure didn’t kill the creativity. Structure is what finally let it out.

Rules and freedom. Architecture and creativity. Framework and expression. Not polar opposites. Partners.

Day 80 of 280. Two rounds down. Five to go.

I got five-star reviews from readers this week. I got a message from a friend who finished my book and is telling people he knows to read it. I’ve lost sixteen pounds. I’ve built a library of strategies and systems that didn’t exist ninety days ago. I wrote a novel by talking into my phone. And none of it — not a single piece of it — exists without the seven habits I committed to on Day 1.

What I want — a year from now, when someone walks through the door of everything I’ve built — is for them to find a roadmap.

I want frustrated people to see a path. I want people who are wondering if they have what it takes to look at this guy who answered that same question a year ago and said: Here I am. This is me. This is exactly what I’m going to do.

Was it perfect the whole time? No. Did I have a glass of wine every once in a while? Yes, I did. Am I going to live my life and enjoy it inside the framework I committed to? Absolutely.

Can you do it too?

You certainly can.

Round 2: Complete.

Assessment Week starts tomorrow. Time to evaluate, rest, and build the plan for Round 3.

The habits hold. The framework works. The freedom is real.

See you on the other side.

Cover Band

~ David Willis ~ Leave a comment

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.

Communication Is Not a Soft Skill

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Day 78 | The 7-40 Challenge

I was listening to Todd Henry’s Die Empty this week, and he referred to communication as a soft skill. I had to stop the book and take a voice note so I wouldn’t forget how frustrated I was.

Communication is not a soft skill. It never was. Calling it one gave people permission to not take it seriously for decades — as if the ability to clearly articulate what you want, what you need, and what you’re willing to give for it is somehow optional. Secondary. A nice-to-have you pick up along the way while you’re learning the “real” skills.

That was already wrong. Now, with AI in everyone’s hands, it’s catastrophically wrong.

Here’s what I mean.

Every bad AI prompt is a communication failure. Every bad email is a communication failure. Every meeting that should have been a five-minute message is a communication failure. Every project that runs over budget, over schedule, and under-delivers — trace it back far enough and you’ll find a communication failure at the root. Someone didn’t say what they meant. Someone else didn’t ask for clarity. And everyone moved forward on assumptions that weren’t shared.

I’ve spent eighteen years in data management watching this happen. I’ve sat in meetings that cost five thousand dollars an hour in personnel — and we had that same meeting three or four times before we reached a resolution that could have been handled in one email if someone had just said the thing clearly the first time. That’s not a soft-skill problem. That’s a twenty-thousand-dollar problem.

Take something as simple as a marriage. She says “let’s spend time together” because she wants quality time — just being with him. He hears “let’s spend time together” and thinks it’s time to tackle projects. Same words. Two completely different outcomes. Multiply that across every interaction in a workday, a business, a family, a community — and you start to see that communication isn’t the seasoning. It’s the main course.

I was my own first convert on this. Early in my career, my manager introduced new data entry standards. I thought they were stupid. I was doing data entry. I didn’t understand why I needed to add extra fields, follow specific formats, and standardize things that seemed fine the way they were. It felt like bureaucracy forced on me from above.

It took time — more than I’d like to admit — before I realized what those standards enabled. With clean, standardized data, I could actually connect records across sources. I could research with confidence instead of guessing. I could build a full picture instead of stitching fragments together and hoping the correlations were real. The standards weren’t slowing me down. They were giving me a language that worked.

Communication standards work the same way. When you define your terms, clarify your intent, and say what you actually mean — not what sounds close enough — everything downstream gets better. The research gets better. The decisions get better. The relationships get better.

And now we have AI.

If you put ambiguity into an AI prompt, you get ambiguity back. If you give it incomplete reasoning, it fills the gaps with confident-sounding noise. If you don’t tell it what you actually want — specific, clear, no room for guessing — it will fabricate something that sounds right but isn’t. The tool doesn’t fix bad communication. It amplifies it. Polished garbage is still garbage.

But here’s the flip side. Working with AI three to four hours a day has actually made me a better communicator with humans. Not because I treat people like machines — that would cheapen every interaction. But because the discipline of being clear with AI transfers. I write better emails. I ask sharper questions. I define problems before I try to solve them. The muscle you build prompting well is the same muscle you use communicating well. Clarity is clarity, whether the listener is a person or a processor.

Know your message. Know your audience. Keep it simple. Deliver it well.

That’s not a soft skill. That’s a discipline.

The era of winging it is over. Clarity wins.

Day 78 of 280. Two days left in Round 2.

Twenty-Three Years

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Day 77 | The 7-40 Challenge

I found a document on my computer yesterday that I wrote in 2003. I was twenty-four years old. I’d wasn’t too far out be leaving my ministry job. I may have been selling Thomas Kinkaid paintings, or managing a Pizza Hut— I honestly can’t remember when I wrote it but I know it was 2003. I was lost. I needed to find my focus.

The document was called “My Goals for Success.” Here’s what it said:

Exercise every day. Run four days, lift the other three. Log your progress. No soda — juice and water are your friends. Read your Bible first, then the news, then a topic of interest. Engage your mind as much as possible. At the beginning of each day, lay out a list of what to do. Once a month, take four hours to redefine your priorities. Make sure you’re headed in the right direction. Reflect on the good and the bad. Make adjustments.

It ended with this: “You can do it. You can prevail. In just a few short months you will be where you want to be. Do it.”

I realized when I read it today, that is the 7-40 Challenge. Written in Microsoft Word on a work computer twenty-three years before I started it.

Daily exercise. Bible first. Hydration. Reading. Daily task lists. Monthly assessment and course correction. A young man talking to himself, trying to build a framework for a life he didn’t know how to live yet.

I didn’t follow through. Not then. Life happened — cancer, career changes, a son, a move, a second cancer, a pandemic, twenty years of notebooks full of “someday I’ll” goals in different handwriting.

But the system I needed was always there. Sitting in a file I forgot I had. Waiting for the man to catch up to the plan.

I’m seventy-seven days into the 7-40 Challenge now. Seven daily habits. Forty-day cycles. Everything the twenty-four-year-old wrote down, the forty-seven-year-old is finally doing. Not because I figured out something new. Because I finally gave myself permission to do what I already knew.

The notebooks were never the problem. The goals list was never the problem. The knowledge was never the problem.

The twenty-three years between writing it and doing it — that was the problem.

If you’ve got a list like mine sitting in a drawer, a notebook, or a file you forgot about — go read it. You might find out you already know exactly what to do.

You just haven’t started yet.

Day 77 of 280. Three days left in Round 2.