Wayward Weekly Wisdom (W³) - Issue III
I’m Drawn to Curiosity and to the Discipline of this Weekly Practice of Awareness.
Welcome back, leaders, to this weekly curiosity experiment. Thanks for being here again as we figure this out together. I know your time is valuable, and I'm grateful you're trusting me with a few minutes of it while this community grows. This weeks issue is just a little be longer than 10 minutes due to being snowed in and having more time to reflect than normal (in between building snow forts, shoveling, and hot cocoa).
This Week’s Reflection:
“Until you make the unconscious conscious, it will direct your life and you will call it fate.”
— Carl Jung
This week a young teen came up to me and launched into something they were really proud of. A quick “Hi, how are you doing,” and then...everything. I knew immediately what they were telling me mattered a lot to them.
We don’t brag accidentally.
If someone’s kids are central to their life, they talk about their kids. If work is the altar, they talk about work. If achievement is the measure, they talk about grades, titles, wins. Kids do this instinctively. Adults just get better at disguising it.
We like to say values are private. But attention leaks. Words give us away every time.
We can claim faith, family, friendship, service. But what we consistently talk about reveals what we’ve actually organized our life around. Not what we wish mattered. What actually does.
I’ve been reading Dr. Robert Kegan’s work on adult development this week, specifically his framework of the socialized mind, the self-authoring mind, and the self-transforming mind. The central idea is that development isn’t about accumulating more knowledge. It’s about transforming what shapes you into something you can examine. This feeds into how awareness is the outcome of wisdom in first part of the Wayward Framework.
Consuming information and experiencing transformation are not the same thing.
You can read every book on leadership and still manage from fear.
You can listen to every marriage podcast and still check out daily.
You can scroll through endless self-help content and still never examine the assumptions running your life.
Without diving into everything here in this reflection, Kegan talks about the “seat of judgment.” The place from which you make meaning. The framework that determines “this is who I am” and “this is what I stand for.”
If you brag about what other people think of you, you’re in the socialized mind; shaped by external validation, unable to step back and question things. If you brag about what you’ve built, you’ve moved to the self-authoring mind. But there is a catch.
Technology and tools built on dysfunction = still dysfunction.
Picture this throne atop a trash pile in a landfill. That’s your seat of judgment when you’re proud of the systems, tools, code, framework, relationship, or organization you’ve built or engineered; while remaining blind to the foundation beneath them not being addressed.
Which brings me to something that’s bothered me my entire career...
The Problem with “Bloom Where You’re Planted”
I've heard this phrase constantly, and I just don't like it.
Accept your circumstances.
Don’t question anything.
Make the best of it.
Choose gratitude.
I had to deal with the same thing, so you can deal with it the same way I had to.
But sometimes the problem isn’t the plant. It’s the garden, the soil, the seed, or the gardener.
Plants don’t choose where they’re planted. They have no agency.
A seed thrown onto concrete doesn’t bloom through sheer willpower. It dies.
A plant in toxic soil doesn’t thrive through positive thinking. It withers.
A gardener who doesn’t take care of their plants and soil, well you guessed it, kills everything.
When someone tells you to “bloom where you’re planted,” they’re often keeping you from examining the conditions themselves, don’t know what to say (or does not care), or they are projecting their own self-limiting beliefs onto you. They’re asking you to treat the symptom instead of addressing the structure.
Now in real life, sometimes you have to accept that you might have to “shut up and color,” but when in a position to address the structure, you always should.
Now, people in this type of moral disorientation don’t want to be told they’re fine. They want to know why they feel this way. They want structure. Language. A framework that helps them make sense of what they’re experiencing.
Most systems try to treat the symptom: take a break, practice self-care, adjust your attitude, be more grateful.
But the veteran, or service member, health care worker, or person serving with their whole selves in their role, who end up experiencing moral injury are not looking for a pause button. Most of the time they’re trying to reconcile the act with their soul. They’re trying to integrate what they’ve done, seen, or become into a coherent sense of self.
And most of the time, the old frameworks and ‘containers’ we have can’t hold it.
This is where people numb. Where I have numbed. But numbing doesn’t resolve the structural problem. It only delays the collapse. And the cost of unconsciousness thinking is not fate. It’s passivity.
What Jung was getting at in the quote above is that when you don’t make the unconscious conscious, you don’t get to choose. It’s remaining subject to assumptions you haven’t examined.
And that cost isn’t small. It shows up in marriages, in parenting, in leadership, in faith. Development isn’t comfortable; at any stage in life. Making the unconscious conscious isn’t safe. But it’s the only way to stop calling your life fate and start calling it choice.
The Good News is Awareness Changes the Trajectory
Realizing something feels off doesn’t mean it’s all broken and everything is going to hell. It means your conscience is alive. It means your capacity has grown beyond the container you’ve been living in. That moment of discomfort, naming the dissonance instead of numbing it, is the first signal of wisdom.
That’s why the first step of the Wayward framework is Wisdom.
Not knowledge. Not more information. Wisdom as awareness. The ability to step back and see what’s shaping you, what you’ve been organizing your life around, and what can no longer carry the weight you’re holding. Mine first step led me to giving over control of my life to my higher power.
And as I reflect over this past week, I’m not saying we’re doomed. I’m not saying you shouldn’t make the best of where you are. I’m saying that when we tether our identity to things that can’t hold a higher purpose (status, performance, approval, survival) we slowly lose ourselves. And when there’s no framework to make sense of that loss, or moral injuries that come, self-destruction starts to look like an option instead of a warning sign.
Wisdom interrupts that thought, and gives a new direction and path.
As a Husband:
This week I reflected on how it took me years to name and now have the language for a lot of the ways I have shown up in my marriage in the past.
I treated love like something that happened to me instead of a responsibility I chose. Similar to how I use to think how life was something that happened to me versus something that flows through me.
More times than I have ever been comfortable to admit out loud, I know I reacted more times rather than initiating. I waited to be told what was needed and called it consideration, when really it was avoiding responsibility. I was more invested in not failing than in actually loving well. Passivity felt safer than ownership.
Having words for the self-authoring mind means questioning those assumptions and choosing differently. Love isn’t passive. It’s built. Daily. It’s the decision to learn my spouse, to show up without being asked, to initiate because the commitment matters and not because someone prompted me. Things I forgot as life got hectic. Things I am working on daily. Things I am taking ownership of.
I have realized through The Love Dare and working with my wife on our marriage is that what I brag about in marriage reveals where I’ve taken ownership.
If I brag about what my wife does for me, I’m still living in a external validation mindset. Because once she stops doing those things, it becomes comparison and discontent; not love.
If I brag about how I’ve chosen to love her, how I showed up better this week than last, how despite everything I still chose her; that’s ownership.
And yes, it goes both ways, as you can not pour into a closed off, or broken cup. But, ownership, I’ve learned the hard way, is what ultimately keeps love alive.
As a Parent:
This week was another reminder for me that my kids don’t need me to have it all figured out, or have the best job, or provide them with “things” other than my time.
They just need me present, regulated, spending our most valuable resource together (time), and me being honest about who I am.
I don’t chase the false framework of “work-life balance” anymore because life doesn’t divide cleanly; especially when you’re in the car 3-4+ hours a day, haha. The same nervous system that reacts at work reacts at home. There isn’t a parenting self and a leadership self. There’s just me, showing up in different places with the same habits and blind spots.
So I focus on cadence, not balance. When to stay. When to step out. When to slow down. When to return. That matters even more in a house with ADHD, where regulation takes time and modeling matters more than control.
Kids don’t learn regulation through lectures; they learn it by watching how we pause, how we repair, how we return.
What I brag about as a parent shapes what my kids learn to value. If I brag about achievements, I teach performance. If I brag about character, kindness, resilience, love; I get a chance to teach something that lasts. It’s why we don’t use the word “hate” in our house. It’s right up there with the other curse words.
And lastly, if I numb, escape, make excuses, or check out, they learn that too.
As a Leader:
I’ve been getting back into coaching leaders, and this week reinforced something I’ve seen my entire career that we already talked about regarding bragging. But, from a leadership perspective, most times what people stop talking about reveals where they’ve been told (directly or indirectly) to stay passive.
When someone stops bringing ideas or lighting up when you ask what they think, they haven’t lost care. They’ve learned their care isn’t welcome, or matters.
For example, I see this most clearly with my kids. When one of them hands me a rock they found or something they made out of nothing, it’s never about the object. It’s about the offering. That’s all they have, and they chose me to give it to. I receive it with love and tell them it mattered. Because it did, and always will.
Leadership isn’t different.
When someone brings me an idea (even an unfinished or bad one) if it’s coming from care rather than cynicism, I get curious. I ask how they got there. What they’re hoping for. If I don’t have time, I say so, but I still acknowledge the offering. Because they cared enough to bring it.
As a Wayward Disciple:
A simple practice from my Reach More readings this week suggested we should all set an alarm at a random time and have it ask us, “How is God present right now?” Then when it goes off mid-drive or at the grocery store, it forces us to ask in that moment how God is showing up right then and there.
God isn’t waiting for my quiet time. He’s already present in the interruption, the chaos, the moment I want to escape.
I believe moral repair doesn’t come from numbing or pausing life. It comes from integration, cadence, and incorporating the God I believe in into my daily cadence. The alarm isn’t about remembering God exists. It is about remembering I exist in His presence. Especially in the interruptions and chaos I can not control.
Podcasts:
The Learning Leader Show - Great episode this week on the topic of excellence and how the Air Force found through research that military units didn’t rise to the level of the best performer, but actually fell to the level of weakest member in the unit. Goes to show that a lower tide lowers more boats, than a rising tide raises. Interesting thought to further research this coming week.
Reading:
There was a lot of snow this week, so spent a lot more time off the computer and more time hanging out with my wife and kids. It also allowed for more reflection time. This week I reopened the book On Character by General Stanley McChrystal. Most people know him through his work on Team of Teams, but few know of his newest book. I even had the opportunity to get a signed copy from him.
On Character: Choices That Define a Life by retired General Stanley McChrystal: Reread some sections of this book this week I had tabbed out previously.
Soul Boom - Why We Need A Spiritual Revolution by Rainn Wilson: This was a great read. Anyone open to anything religiously or spiritually should read/listen to this book. You don’t even have to be a fan of The Office.
The Love Dare: I have looked forward to reading and talking about each day with my wife ever since she bought this book.
Red Rising: This is turning out of be a great book, and I am excited there are more in the series when I finish it.
Films & Shows:
The Electric State: I really enjoyed this (and you can’t go wrong with Chris Pratt). It made me think more about how easy it is to numb ourselves rather than confront what’s already broken and no longer aligned.
On Discernment:
Words mean things, and we lose a lot when we don’t understand shared vocabulary. Discernment is the ability to see clearly and choose wisely. It’s the practice of slowing down long enough to notice what’s actually happening (within yourself and around you) so you can distinguish what is true, helpful, timely, and aligned from what is merely loud, urgent, or emotionally charged.
I use to think this word was just for the super religious people.
But I have found that discernment is about knowing what matters, what doesn’t, and what’s ours to act on right now. In a world that rewards reaction, discernment for me appears to be the discipline of response. It’s making the unconscious conscious before I act.
As I wrap up this week, one simple question cuts through everything here. If I’m the gardener (not the plant or the seed) what conditions am I actually creating as a Moral Leader? Am I tending soil that can support the complexity I’m being asked to hold? Or am I trying to ask people to bloom on concrete and call it discipline?
When I look back in my life, sometimes I see a monster. Other times, a stranger. I think we all do. For me, this isn’t about killing the monster or ignoring the stranger.
It’s about learning how to accept and integrate the past so it becomes part of how I grow into a better Moral Leader.
So here’s the question I’m carrying into the week ahead:
What are you trying to control from your past that actually needs to be integrated?
And a bonus question, if you want to sit with it a little longer:
What would it look like to stop numbing the tension (trying to change the past) and start building a container strong enough to hold who you are now, and where you are trying to go?
If you want to answer out loud, feel free to leave a comment.
Your time and trust make this space possible. Everything here builds toward one thing: turning moral injury into moral leadership, so self-destruction never feels like an option. If this landed, leave a comment as it helps me know this is reaching real people. Want to support the work? Subscribe or make a one-time contribution. Or share with someone who this might help. However you engage, thank you for being here.
