The Wing-It Tax

7-40 Challenge | Round 4, Day 16

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.

Dare Mighty Things (Fifteen Years Later)

7-40 Challenge | Round 4, Day 16


In 2011, I wrote a short passage about a prisoner escaping a cell. He finds a footprint on the floor — proof that someone walked this path before him. He picks up a sword and feels something pulse through his arm. He remembers: I am a warrior. I have purpose. How long have I been hidden away?

I was writing about myself. I just didn’t know how to say it directly yet.


The fear I described fifteen years ago is the same fear I’m still fighting. The what-ifs. What if I’m not good enough? What if nobody cares? What if I put everything I have into this and it doesn’t work?

In 2011, I took those what-ifs to their logical end and concluded they wouldn’t kill me. That was true. But I didn’t do anything about them. I wrote about escaping and then stayed in the cell for another decade.


This year I walked out.

Not because the fear went away. It didn’t. I still feel it when I think about promoting my work. I still feel it when I put something personal on the page and hit publish. I felt it two weeks ago when I wrote that promotion feels like begging and named it for what it is — pride.

The difference between 2011 and 2026 isn’t courage. It’s decision. I decided that knowing what to do and not doing it was no longer acceptable. I built a structure — seven daily habits, forty-day rounds — and I started doing the reps. One hundred and fifty-two days later, the what-ifs are still there. They just don’t run the schedule anymore.


The passage I wrote back then had a line I didn’t fully understand when I wrote it: “The first step was finding the path, and as I make my way I start to remember who I really am.”

I understand it now. The path was always there. The warrior was always there. I just needed enough reps to remember.

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.

Headfirst

7-40 Challenge | Round 4, Day 9


I started reading Admiral McRaven’s Make Your Bed today while mowing the yard. Chapter 6 is called “Dare Greatly.” It’s about the slide for life in SEAL training — the obstacle where going headfirst is faster but terrifying, and most people go feet first because it feels safer.

I know exactly what my version of feet first looks like. Keep creating. Keep writing blog posts. Keep building things in private. Keep doing the comfortable parts of this challenge and never venture into the hard part — which is telling people about what I’ve built and asking them to care.


The thing I’m most afraid of is making a marketing plan and sticking to it. Not because I don’t know how to talk to people. Not because the work isn’t good. Because somewhere deep down, I don’t want to look like I’m asking for help. I don’t want people to think I’ve got my hand out. Promotion feels like begging, and I’ve had a chip on my shoulder my whole adult life about wanting to be taken seriously.

That’s not irrational. It’s pride. And it’s been in the way for a long time.


I asked myself two questions this week.

What’s the worst thing that happens if I go headfirst and it doesn’t work? I still have my day job. I still have my family and my home. The worst case is a little egg on my face and a recovery. That doesn’t sound all that bad.

What’s the worst thing that happens if I stay safe? Then I’m an impostor. I built all of this — two novels, 144 days of habits, a business plan, a framework that works — and I never let anyone see it. That’s worse than rejection. That’s hiding.

And I’m done hiding.


The funny thing is, I’ve gone headfirst before. I went headfirst into my relationship with my wife because I knew exactly what I wanted and I didn’t care what anyone else thought. I went headfirst into my master’s degree. I went headfirst into every career move that mattered.

The creative work and the business — I turned those into some magical unicorn that required a level of courage I supposedly didn’t have. But they’re not magic. People do this every day. And here I am, stuck having a hard time getting over myself.


Thirty-three days left in Round 4. Time to go headfirst.