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.

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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.

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.

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

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.

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