The Wing-It Tax

7-40 Challenge | Round 4, Day 17

I was 19 and a bit unobservant. I signed up for what I thought was personal finance. I wanted to learn how to balance my checkbook. I ended up in fundamentals of business finance, learning bond valuation.

I did what I always did in college — I winged it. Showed up, skated through, and crammed at the end. Pretty sure I got a D. I was happy with it.

In retrospect, I’ve worked a corporate job for almost twenty years. The financials aren’t that hard to understand. If I had taken some focused time early that semester, I would have learned the material and been fine. It wasn’t a smarts thing. It was a wing-it thing that almost bit me.

I leaned on talent for most of my life. Smart kid, underachieving student. A 2.87 GPA in my undergrad, mostly propped up by passing all of my music courses.

Then I went back for my master’s degree and decided to get my act together. I studied. I did the assignments. I prepared instead of crammed. I graduated with a 3.95.

The only thing that changed was the work ethic.

I think most people romanticize the idea of working well under pressure. I think that’s nonsense. Very few of us actually work well under pressure we manufactured through our own laziness. We just convince ourselves we do because we survived it. Surviving isn’t thriving. And the work that comes out of a last-minute scramble shows it.

If I could go back and tell the kid in that finance class one thing, it would be this: the difference between a 2.87 and a 3.95 wasn’t talent. It was deciding to stop paying the wing-it tax.

The Drift You Don’t Notice

7-40 Challenge | Round 4, Day 15


Week one, you push back on everything AI gives you. You check the output. You question the reasoning. You verify the facts. You’re in charge and you know it.

By week ten, the checking feels redundant. The tool has been right so many times that pushing back seems like wasted effort. So you stop. Not all at once — you just skip a verification here, accept a suggestion there. And somewhere between week one and week ten, you’ve abdicated without ever choosing to.

That’s the trap. You don’t abdicate by decision. You abdicate by trust accrual.


I use AI every day — for writing, for data work, for thinking through problems. It is the most powerful tool I’ve ever worked with. And the more powerful it gets, the more dangerous the drift becomes.

Because it gets worse as the tool gets better, not better. A sharper tool makes abdication more tempting. The output looks cleaner. The reasoning sounds tighter. The errors get harder to spot — not because they’re smaller, but because they’re wrapped in fluency that makes you want to believe them.


Here’s what I’ve learned from the chair: AI is a reasoning engine, not a truth source. It doesn’t know anything. It processes what it’s given and returns the most plausible-sounding result. If the truth isn’t in what you’ve supplied or what it’s been trained on, it starts on the wrong foot and builds confidently from there.

My edge is whatever only I can supply — my intent, my standards, my domain knowledge, my ability to say “that’s wrong” when the output sounds right.


The thing nobody tells you is that AI doesn’t erode your ability to reason. It erodes your exercise of it. The muscle is still there. You just stop using it because the tool made it feel unnecessary. And by the time you need it — the day the output is confidently, fluently wrong — the muscle hasn’t been worked in months.


I have one rule that doesn’t bend: if I ship it, it’s mine. Not AI’s fault. Not the tool’s limitation. Mine. I signed off on it. My name is on it.

The signature got cheap. The responsibility didn’t.

The Volume Group

7-40 Challenge | Round 4, Day 12


There’s a story about an arts professor who split his pottery class into two groups. The first group only had to produce one piece for the entire year. One shot at perfection. The second group was graded on volume — they had to produce as many pieces as possible, measured by weight at the end of the semester.

At the end of the year, the volume group didn’t just produce more pottery. They produced better pottery. Piece after piece, the craft improved. Meanwhile, the single-piece group spent the year theorizing about what good pottery looked like and never developed the skill to make it.

I think about that story a lot.


I’m 500 posts into BiblePictures365 on Instagram and TikTok. The compositions are stronger now — better framing, better detail, images that actually stop a scroll. I’ve written a blog post every day this year, and the change there is different — the arguments are tighter, the thinking is more organized, and I waste fewer words getting to the point. Two different crafts, both sharpened the same way. Not by studying theory. By shipping something every day and letting the reps do the teaching.

Volume made the quality better. Not worse.


There’s a difference between volume and noise. You can only turn it up as loud as it is good. Go louder than the quality supports, and it’s just blaring — it hurts more than it helps.

But the answer to that isn’t to go quiet. It’s to keep producing at the level you’re proud of and let the reps tighten the craft.


I have no way of knowing everyone who’s seen my work this year. I just know that none of it would have reached anyone if I hadn’t shipped it.

Five five-star reviews on Amazon — most from people I hadn’t spoken to in years — exist because I published the book. 8,000 Instagram followers exist because I posted every day. Over 400,000 views on one video exist because I was already 200 posts deep when it hit.

If I had not shipped these things, they would not have had a chance to impact people.

Never Ring the Bell

7-40 Challenge | Round 4, Day 10


I’m reading Admiral McRaven’s Make Your Bed this week. In Navy SEAL training, there’s a brass bell. If you want to quit, you ring it. You’re done. No more cold water, no more impossible runs, no more being pushed past what you thought you could take.

McRaven’s message: if you want to change the world, never ring the bell.


My bell doesn’t look like that.

There’s no brass bell in my living room. Nobody’s watching to see if I ring it. There’s no ceremony to my quitting — no moment where everyone knows I stopped.

My bell is when I stop doing the habits.

It’s the morning I skip Bible study because I’m running late. It’s the day I don’t track my calories because I already know I went over. It’s the walk I don’t take, the book I don’t open, the blog post I decide can wait until tomorrow. One day becomes two. Two becomes a week. And by the time I notice, the structure I built is already eroding and I barely heard it happen.

That’s what makes the ordinary bell harder than McRaven’s. His bell is loud. Mine is silent. His is a single dramatic decision. Mine is a hundred tiny ones, each one so small it doesn’t feel like quitting. It just feels like a day off.


I’ve rung my bell before. Not this year — but I know exactly what it sounds like. In 2022, I lost significant weight, stopped doing what got me there, and the habits dissolved so quietly I didn’t realize they were gone until the weight was back.

That’s why I built the 7-40 Challenge the way I did. Not as a goal with an endpoint, but as a rhythm that doesn’t stop. The habits are the structure. The structure is what keeps the bell out of reach. As long as I’m doing the seven things — even imperfectly, even six out of seven on a rough day — I haven’t rung it.


Day 5 of this round, I hit the wall. Six out of seven habits. No creative work. In bed early. That was a bad day. It wasn’t the bell. The bell would have been Day 6 looking the same. And Day 7. And Day 8. Until I stopped counting altogether.

Day 6, I came back. That’s the difference.


McRaven’s bell is dramatic. Mine is ordinary. But the commitment is the same — you decide, every single day, that you’re not done yet.

What Twenty Minutes Will Tell You

7-40 Challenge | Planning Week


It’s 80 degrees. I’m in jeans and a black shirt, walking downtown in full sunlight with a balding head, talking into my phone passing a bus stop at 12:45 in the afternoon. I’ve got about 14 things on my to-do list and I’m trying to unload my brain before it gets any fuller.

I’m equal parts grateful and overwhelmed, and I can’t figure out how both of those things are true at the same time.


I’ve been feeling behind. Not in a dramatic, everything-is-falling-apart way. More like a low hum in the background — the sense that I should be further along, that I haven’t done enough, that time is slipping and I’m not keeping up.

So I started talking. Just listing things. What have I actually done this year?

I wrote a novel. Edited it from 105,000 words down to 60,000. Published it through Kindle Direct in March. Five months from manuscript to published book.

While I was editing that one, I wrote another one. 45,000 words. It’s in revision right now.

I’ve blogged every single day this year. Over 130 posts.

I’ve read 13 books and I’m working on my 14th.

I’ve written new songs and produced a companion album for my first novel.

I started a Bible illustration project on January 1 with zero followers. Instagram is at 6,300. One video hit 300,000 views.

I’ve maintained seven daily habits across three 40-day rounds. I’ve walked so much I’m on my third pair of shoes. I’ve lost over 23 pounds and gained 10 pounds of lean muscle. My metabolic age dropped 20 years.

I’ve worked with my wife to put together her garden, and she likes it. I’ve been in the gym with my son three nights a week. And I’ve done all of this while working a full-time job.


Somewhere around minute fifteen of this walk, I heard myself say it out loud: I think I’ve been seriously deluding myself that I haven’t been doing enough.

That stopped me.

Because the problem was never output. The problem was that I was so deep inside the work that I couldn’t see the shape of it. I was measuring myself against what I hadn’t done yet instead of what I’d already built.

Twenty minutes of talking into my phone at a bus stop fixed that.


So now the question changes. It’s not “am I doing enough?” I am. It’s “how do I get what I’ve built in front of the people who need to see it?”

That’s a different problem. A better one. But it’s still a problem. I don’t have the answer yet. I’m one person producing more than I can promote, and the gap between what I’ve made and who’s seen it is real. The overwhelm doesn’t go away just because I’ve named it — it just shifts from “I’m not doing enough” to “I don’t know what comes next.”

But I know where to start. And I know I’m not doing it alone.

Thank you, God. I am so grateful.