TL;DR: Last week, I turned 54, walked the battlefields at Antietam, had coffee with three great friends, and experienced that the cost of hesitation isn’t always dramatic. Sometimes it just looks like just saying “maybe.” 

"On Going Long"

12 April 2026 

Hiya 

A challenge coin doesn’t come with fanfare. 

It comes quietly. A hand extended, a brief exchange, eye contact that says, “This meant something to me.” 

Leaders don’t have to do it. That’s the whole point. It’s not a policy. It’s not a checklist item. When they do it, it’s because something landed – really landed – and they want you to know without making a production of it. 

I was coined 3 times last week. 

I’m still not sure what to do with that. I keep turning it over. 

One of those coins came from a three-star at dinner on Monday night. But the story starts much earlier. 

When I found out he was the senior mentor of the event I'd been invited to, I went into my collection and found his older coin – the one he’d given me at least two years ago, when I’d been called in to serve his unit as a leadership development resource.

I brought it knowing I wanted to show him. 

Before we started, I found him, pulled it from my pocket, and said, “I remember the last time we were in the same room together.” 

He smiled. Didn’t say much. We leaned into our work that day.

That night at dinner, he coined me again... 

I don’t plan moments like that. It shows up having carried the right things – and somewhere between sunup and sundown, the thread reveals itself. 

In one of the “mentoring moments” that he and his Chief shared, he told the folks in the room that day that “…our past informs our present and sets us up for the future.”

I already knew. I’d been carrying the evidence in my pocket, a story to tell.

During that same Monday, another leader – on his way to Command – told me he still had a 3x5 card from a workshop I facilitated years ago. It was tucked into his notebook. He smiled and said the work we were doing that day, while familiar to the last time we were in the same room, was different enough to make the day worth it. 

I didn’t ask to see his card... 

I wanted to hear his story – where he’s going next, what he’s carrying, what the work means to him today. The card was his. The moment we were in was ours. 

That’s the thing about artifacts. 

We don’t make artifacts knowing we’re preserving something. We hold on because something felt true – because we were fully present in a moment and something in us knew it. Years later, we look back and see ourselves: who we were then, quietly informing who we are now. 

Maybe that’s the whole point. 

On Wednesday, I stood at the edge of the cornfield at Antietam. 

A group of us walked the ground where, in September 1862, General McClellan had every advantage – more troops, more resources, play-by-play plans of what Lee intended to do, and somehow, even the enemy’s battle plans. He still couldn’t decide. 

He waited. 

He hedged. 

He said, “Maybe.”

The Confederates held. 

Standing on that field, I kept thinking: the cost of hesitation sometimes it is dramatic…sometimes no. 

Sometimes it just looks like a leader with everything they need, still waiting for the certainty that the moment will never offer. The intelligence was there. The conditions were there. What was missing was the willingness to act on what was already true. 

According to a history . com page, McClellan wrote:

“I did not want to risk another battle… I felt that I had done enough for one day and that I should not risk the safety of the country by a too hasty attack."

I spent a LOT of time in both Claude and NotebookLM workin’ to connect what I do day to day for my leadership teams with the lessons we can learn from the Battle at Antietam.

Yesterday, I rode my bike 54.54 miles. 

I didn’t plan that number. I started out thinking I’d do my usual “Saturday 42.” Somewhere in the back of my mind, a whisper, “Maybe I’ll go 50 today.” Interestingly enough, after about a mile of riding from the start, one of the guys pulled alongside me and said, “JW, go long with us today!” 

I said, “Maybe.” 

The moment I said it, I knew what I’d done. 

You know what “Maybe” means, right? It meant I’d already handed myself the exit. Same as McClellan. All the conditions were there. The road was in front of me. The guys were riding long; they’d already decided. 

Out loud, I heard myself say, “Dude. Go.” 

Yup, out loud. To no one in particular, but to everyone at once. Including me.

Committed.

I didn’t know the full route. Didn’t know most of the guys riding at that point. Didn't know "exactly" how much longer I'd be on the bike. I made the decision and put my trust in the process. 

As I turned off Granada, about to enter the driveway, I looked down at the computer:

54.54 

I turned 54 this week. I could not have planned that distance if I tried. 

I’ve been sitting with a question all week.

Not a heavy one – more like something I’m holding up to the light and turning slowly. 

I'm 54... am I about halfway done? 

On a run Friday morning, my mentor (and boss!) pushed me. Not JUST to think bigger – I was already reaching for that. Because of our run together on my birthday, I realized how important – and life-changing – it can be to think alongside people who see further than I do. 

Because alone, I don’t even know what’s possible. But when I share the beginning of a thought and let someone else extend it – that’s when the route gets longer than I imagined.

That’s when I turn into the driveway, and the number surprises me. 

Fifty-four feels less like an arrival and more like mile ten. 

Dude. Go. 

Hey, do you have a 3x5 card somewhere?

Maybe literal, maybe not. A moment you were fully in, a decision that shaped you, a version of yourself you preserved without knowing it. 

It’s still in your notebook. Go look at it. Connect what you wrote or thought back then to today…to the future. What would it mean to stop saying maybe – and "go long?" 

Until next week, 

JW

PS: I finally designed and ordered MY challenge coin. Those of you who know ... it's comin' your way, so get ready... some heritage stuff, some current stuff, and some future stuff that I'll explain later!

PPS: If you're still lookin' for something to get me for my birthday, shoot me text, I have THE ask! (805) 798-1362

LINKS: 

An animation of the Battle of Sharpsburg (AKA: Antietam); and, the recommended Hollywood version of the beginning of the day, 17 Sep 1862.