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 Surgery

7-40 Challenge | Round 4, Day 14


I used to think that when I finished writing something, I was done. The story was out. The work was complete. Move on to the next thing.

That was shortsighted and a little arrogant.


I’m sitting in a coffee shop tonight working on the editorial pass for my second novel. The bones are solid. The arcs are where they need to be. What I’m doing now is polish — adjusting the reader experience, tightening scenes, making sure the story feels cohesive from the first page to the last.

And I’m enjoying it. That’s the part I didn’t expect.


I used to dread editing. It felt like going backward. The creative rush was in the writing — getting the story out, discovering the characters, finding out what happened next. Editing felt like admitting the first version wasn’t good enough.

It wasn’t. And that’s not a failure. That’s how stories work.

The things we love in books — the moments that land perfectly, the detail in chapter two that pays off in chapter twenty, the line of dialogue that feels inevitable — those aren’t first-pass items. They’re the result of careful editorial surgery. Someone went back in and made the good parts great and cut the parts that were only there because the writer liked them.


Here’s what the surgery looks like today. I discovered I was being too on the nose — telling the reader what to think about events instead of trusting them to pick it up. The story elements are all staying. The structure is solid. But there’s a pattern running through the manuscript where I’m explaining what a scene means instead of letting the scene do its own work.

That’s the kind of thing you can’t see in the first draft. You’re too close. You’re too in love with making sure the reader gets it. The edit is where you learn to trust them.


The other thing that’s changed is the standard. A younger version of me would have been satisfied to just do a good job. Get it done, ship it, move on. I’m not that guy anymore. I want the work I put out to be the best I have — not perfect, but the best version I can make. I want the reader to smile, or think, or feel something they needed to feel. And I owe it to them to go back in and make sure I’ve given them that chance.

The first draft is where you create the story. The editing process is where you learn to trust your reader with it.

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.

In Search of Soho People

7-40 Challenge | Round 4, Day 11


Malcolm Gladwell opens The Tipping Point with the story of Hush Puppies. A dying shoe brand — almost pulled from production — that exploded into a national trend because a handful of kids in Soho started wearing them. The company didn’t cause it. They nearly killed the brand. The tipping point happened because the right people found the product in the right place at the right time, and it spread from there.

I need to find my Soho people.


I have a five-star review on Amazon from a guy I went to high school with. We haven’t spoken in almost thirty years. He found my book off a single Facebook post, read it, and left a review comparing it to Brandon Sanderson and Robert Jordan. He said he put everything else down to read it. He wants the sequel.

One Facebook post. One reader. Thirty years of silence, and the book broke through it.

He’s not the only one out there. I know that. The problem has never been the product. Every person who’s read Phase Defiant has told me they couldn’t put it down. The problem is that almost nobody knows it exists.

I have a how-the-heck-do-I-get-this-in-front-of-people problem.


Gladwell’s point isn’t that Hush Puppies were great shoes. It’s that tipping points have structure. They don’t happen by accident — they happen because conditions are right. The right people, wearing the right thing, in the right neighborhood, at the right time.

I’m a storyteller who wrote a book. I don’t know where my ideal readers gather. I just know the book is good, and the few people who’ve found it agree.

So this week, I’m not trying to sell to everyone. I’m looking for my Soho — the small group of readers who will grab this book and not be able to shut up about it. I don’t need a million of them. I need a few in the right place.

I’ve spent five months building things I believe in. Now I have to learn how things spread.