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.

No Guilt in the Ice Cream

7-40 Challenge | Round 4, Day 6


Yesterday was rough. I hit the wall. Six out of seven habits, no creative work, no Substack, in bed early. It happens.

But two days like that don’t get to happen in a row.


This weekend is Memorial Day. My goal is to enjoy myself. Eat some good barbecue. Have a bowl of homemade ice cream — maybe two. Spend time with my family that is so incredibly precious that no calorie count is worth missing it.

I’m not giving myself a blank check. I’m not doubling my calorie goal. I’m saying there’s no guilt in the ice cream. There’s no guilt in choosing to be present with the people I love over tracking every number for three days.

Bible study continues. Gratitude continues. Walking continues. The floor doesn’t move. But the ceiling gets a little breathing room for a weekend, and when Tuesday comes, everything tightens back down.


Happy Memorial Day. The 7-40 Challenge goes on.

The Good Hydra

7-40 Challenge | Round 4, Day 2


I just finished Josh Kaufman’s How to Fight a Hydra. It’s a short fable about facing an ambitious, terrifying challenge — the kind where you cut off one head and two more grow in its place. The hero enters the arena not knowing if he’ll survive, gets staggered, recovers, and keeps swinging.

I recognized the arena. I’ve been in it for 138 days.


But here’s where my story breaks from Kaufman’s metaphor. His hydra is made of problems. Fear, uncertainty, risk — heads that are trying to kill you.

My hydra is made of good things.

Two novels. A daily blog. A Bible illustration project. Music. A nonfiction book outline. A teaching series. A certification to study for. A distribution strategy to build. A platform to grow. Every single one of them is something I care about. Every single one of them deserves my time.

And every time I finish something, two more ideas grow in its place.


That’s the version of the hydra nobody warns you about — the one where you can’t cut a head because none of them are the enemy. The problem isn’t that the work is hard. The problem is that there’s more good work than there are hours, and it feels wrong to set any of it down.

But the hero in Kaufman’s fable doesn’t fight all the heads at once. He’d die. He picks one, fights it, recovers, picks the next.

That’s not elimination. It’s sequencing. And sequencing requires a harder kind of discipline than grinding — it requires you to look at something you care about and say, “not yet.”


For Round 4, I’ve locked two heads. Get ready to sit my CDMP exam at the end of June. Get Phase Defiant in front of more people. Everything else — the other novels, the teaching series, the nonfiction — stays alive, but it waits.

The hydra isn’t going anywhere. Neither am I. But I can only swing at one or two heads at a time and expect to survive.

Three Days Out

7-40 Challenge | Planning Week, Day 8


Round 4 starts Monday.

I’ve spent the last ten days doing something I don’t do well: stopping. Not stopping completely — I’ve still been writing, walking, going to the gym, keeping the habits that needed keeping. But I pulled back from the pace that carried me through three rounds, and I let myself look at what I’ve actually built.

It’s more than I thought. A lot more. I wrote about that earlier this week — how twenty minutes of talking into my phone at a bus stop was enough to show me I’d been measuring myself against what I hadn’t done instead of what I had.

That realization changes what Round 4 is about.


Rounds 1 through 3 were about proving I could do this. Build the habits. Ship the work. Show up every day. I did. The output is real and it’s documented.

Round 4 is about something different. The question isn’t “can I keep going?” I can. The question is “how do I get what I’ve built in front of the people who need to see it?”

That’s a distribution problem, not a production problem. And it requires a different kind of discipline.


The daily structure is changing too. Not the seven habits — those stay. But where they live in the day is getting a redesign.

Bible study and BiblePictures365 go first thing in the morning. Walking happens before lunch. Reading rides with the walk. Gratitude goes early, because starting the day grateful changes the shape of everything after it.

Creative work moves to the afternoon and evening in shorter, cleaner windows. I’m still in the gym with my son three nights a week. And after that, I’m done. No heavy thinking after the gym. No grinding out a blog post at 11 PM when I’ve got nothing left.

The goal isn’t to do less. It’s to stop pretending I can do everything at any hour and have it all come out at the same level.


Three days. Then we go again.

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.