Day 67 of 280 | The 7-40 Challenge
I finished Austin Kleon’s Show Your Work today. In the last chapter, he says something that stopped me mid-stride on my walk:
When you’ve learned something really well, go back to the beginning. Learn something new. Do it in the open. Do it in public. Show your work so you can keep going, keep expanding, keep building.
It feels like that’s exactly what I’ve been doing.
Before I started the 7-40 Challenge, I’d been blogging on and off for years. I had over 630 blog posts written before 2026. I’d written over 50 songs. I’d done other challenges for myself.
Back in 2022, I created something I called 100 Days Strong. For 100 days, I practiced many of the same habits I’m doing now — exercise, water, reading, discipline. I wasn’t reinventing the wheel. I saw 75 Hard, didn’t love every facet of it, created my own version, and added 25 days. Not rocket science.
I muscled through it. Lost 40 pounds. Proved I could do it.
But here’s the thing: because I wasn’t able to iterate — because I wasn’t able to evaluate as I went — it became a fitness challenge wrapped in the guise of something bigger. 100 days was too long. Too drawn out. No opportunity for adjustment. And because the habits never got implemented in a sustainable way, I reverted. The weight came back. The momentum died.
In 2025, the 7-40 Challenge was born. I did the first round in August and September, right after moving back to Oklahoma City. 40 days. Pulled it off. It went well.
Then I tried Round 2. It failed.
I restarted. Failed again.
I had to sit down and ask myself an honest question: why does this keep falling apart?
And the answer wasn’t willpower. It wasn’t desire. It wasn’t the habits themselves. It was structure.
I didn’t have goals behind the habits. I didn’t have a daily cadence that connected what I was reading to what I was writing to what I was building. I didn’t have a vision laid out in front of me. I didn’t have a place to put my thoughts. I didn’t have project buckets to organize the multiple lanes I wanted to pursue. I was trying to restart on sheer determination, and determination without a system just burns out.
So when January 1, 2026 came around, I built the system first.
I laid out the vision. I set goals behind the habits — even if I don’t share them all publicly. I committed to blogging every single day, not as a chore but as the processing engine for everything I’m learning. I set up project spaces where I could build context over time instead of starting from scratch every session. I created assessment weeks between rounds so I could come up for air, evaluate, and adjust.
And I made a decision. Not a feeling. A decision. I don’t care how I feel. I don’t care what stands in my way. I’m not stopping this time.
That decision, backed by a system, is why I’m sitting here on Day 67 with no missed days. Not because I’m tougher than I was in 2022 or 2025. Because I’m better organized.
Here’s the other thing Kleon helped me see today. I used to think in very linear terms. I could progress in fitness, but it was harder to progress in creativity at the same time. I could progress in my career, but not in my eating habits. Everything felt like it had to happen one at a time, in sequence, or not at all.
I was selling myself short. I’m much more capable than I was making it out to be. But it was never a capability problem. It was an organization problem.
When I have my vision clear every day — when I can see the lanes, the projects, the habits, and how they connect — what would have felt like a chore becomes a rhythm. What would have felt overwhelming becomes manageable. Not because there’s less to do, but because everything has a place.
Before I had the right tools and structure, I couldn’t get my response cycles fast enough to actually iterate and change. I’d have ideas on a walk and lose them by evening. I’d read something powerful and never connect it to what I was building. Now, when I’m walking and voice-texting like I am right now, I can get all my thoughts out. I can process them. I can connect them to the bigger picture. And I can execute.
Austin Kleon says go back to the beginning. Learn something new. Do it in public.
That’s what this whole year is. I went back to the beginning — back to the habits that I knew worked, back to the discipline I’d proven I could maintain — and I rebuilt it with the structure it was always missing. I’m learning in public every single day. I’m showing my work. I’m pushing the edges in every area of my life that I want to pursue.
And I’m finding myself going much further than I ever expected to.
At the end of the day, I know I have to stay teachable. I have to keep the posture of a student. I have to keep learning and growing, because if I don’t, I’m not just setting myself up for failure — I’m not getting any better. And getting better is the whole point.
Keep moving forward.
Day 67 Scorecard:
✅ Bible study and prayer
✅ Walking
✅ Reading (Show Your Work — Austin Kleon — finished!)
✅ Calories tracked
✅ Water (100 oz)
✅ Gratitude
✅ Exercise
✅ BiblePictures365
✅ Creative hour
David Willis 