Headfirst

7-40 Challenge | Round 4, Day 8


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.

Every Test Is a Milestone

7-40 Challenge | Round 4, Day 8


I had my yearly cancer checkup this week. Blood work came back exactly where it should be. Screening was clean. The doctor was pleased.

It doesn’t matter how much time goes by. It always feels good to get those results back. I believe firmly in my heart that this is never coming back. But every clear test is another milestone — another confirmation that I’m still here and still doing what I’m supposed to be doing.

I don’t get as nervous at test time as I used to. But it still means something.


What it gives me is perspective. The kind you can’t manufacture and wouldn’t wish on anyone, but once you have it, it doesn’t leave.

We are not promised tomorrow. And knowing that — really knowing it, not as a greeting card but as something you’ve stared down twice — changes the way you walk into every day. It makes gratitude less of a habit and more of a reflex. It makes wasted time feel heavier than it used to.


I’m still here. And I don’t intend to waste it.

Week 1

7-40 Challenge | Round 4, Day 7


Round 4’s first week is in the books. Here’s what it looked like.

Day 1, I locked the priorities for the round. Two targets: get ready to sit my CDMP exam and get Phase Defiant in front of more people.

Day 2, I finished a book, started another, and published two blog posts.

Day 3, I drove from Oklahoma City to Dallas with a list of questions and a voice recorder. Two and a half hours of talking produced 18,000 words of raw material — business strategy, financial planning, a distribution roadmap, a seven-part writing series framework, and a rebuilt essay. Five documents came out of one car ride.

Day 4, I published a post and drafted another one while fighting a headache.

Day 5, I hit the wall. Six out of seven habits. No creative work. In bed early. It happens.

Day 6, I punched back. Full day. Every habit. Gym with my son.

Day 7, everything done. Holiday weekend ahead.


One rough day out of seven. The system held. The habits didn’t break — they bent for a day and came right back.

That’s what Week 1 looks like when the question isn’t “can I keep going” but “how do I build something with what I’ve already proven I can do.”

Six more weeks in Round 4. We’re just getting started.

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.

Some Days

7-40 Challenge | Round 4, Day 5


Some days you hit everything on the list. Some days you don’t.

Today I got my Bible study done. Gratitude done. Calories and hydration tracked. Bible pictures posted. Reading done. That’s five out of seven habits, and on a day where I had nothing left, I’ll take it.

No workout. No Substack. No creative hours. Just a man who ran out of gas before the day ran out of hours.

The system was built for days like this. Not every day is a clean sweep. The habit participation is what matters — not the streak, not the perfection. Show up for what you can. Let the rest come back tomorrow.

Tomorrow it will.