The closer I move towards fulfilling what matters most in my life, the more I seem to meet the threshold guardians of resistance, chaos, challenge, and distraction.
There are two simultaneous truths in my world in this moment. This is the most devoted I’ve ever been to my life’s work. AND, this is the most chaotic summer I can remember in my adult years.
Since being a young kid, I’ve been on a mission. As long as I can remember, I had an overwhelming amount of creative energy.
It was a lemonade stand at 8-years-old on the golf course behind our house that ended up getting shut down because of the business we were taking away from the Beverage Cart Ladies. And then a homemade candy empire out of my 7th grade locker (also eventually shut down by the “authorities.”)
It was an initiative in downtown Nashville my freshman year of high school providing food and clothing to the unhoused and a project to bring underfunded public school students onto private school campuses during summer time. And then Daymaker, the company I helped start while at Chapel Hill that went on to send over $4,000,000 in sustained enrichment to high-poverty communities while working with companies like Airbnb, Salesforce, Coinbase, and Ally Bank to shift their culture towards generosity.
My life has been a continued lesson in how to cultivate and channel this energy, on behalf of what actually matters. I can see how it’s all led to this moment in time with Heart of Men.
It’s in this chapter where I feel a resounding clarity in what is actually mine to do. Where I see how what the world needs from me overlaps with what I want to give. And where I feel pretty fucking capable in doing it.
I dreamed about this kind of moment for a decade+ of my life. Even when I was running Daymaker and we were doing well and there was lots of attention, I knew there would be a day where I would feel fully in the current of what was mine to do.
In those dreams, I often saw myself in a spacious, wood-finished, big-windowed cabin on the side of a natural lake, doing my life’s work, reading poetry by the fire, and taking long swims and walks between creative sessions. Everything would take shape around this clarity of my life’s work, right?
And the timing of this is impeccable: as I finish typing the above sentence, I have a knock on my office door. It’s my wife. We’re demolishing the interior of an old barn today to store winter hay for the cows.
I started writing an hour later than I had hoped this morning because the dumpster was dropped in the wrong place, and the crew doing the demo needed some additional guidance from me. I’m finally settling into my writing flow, and my wife knocks to let me know the crew needs something from me specifically up in the old barn.
So yes, that fantasy of doing my life’s work with precision. As I’ve moved into the honing, cultivating, and fulfilling of that reason my soul came to Earth, my life doesn’t look like Carl Jung’s Bollingen Tower like I wanted it to. It looks a lot more like a game of a whackamole and circus clowns and ever-present interruptions.
And I stand in the middle of all that, still doing the best I can to show up for the thing that matters most.
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On my best days, I wake up, move, meditate, cook breakfast for my family, take my son for a walk, do some chores, and get to my desk by 10am. I haven’t turned my phone on. I don’t check my email. I ask, “what matters most that I can tend in these next two hours,” and I do it, even if it’s different from what I had on my to-do list for my first creative block.
I’m batting about .500 on the executing of the above vision. 30-40% of the time, I deviate for one reason or another, but I still end up finding my way into the current of what’s most important for the day.
And then about 10% of the time, I’m a complete miss. A weakened willpower to aikido all of the interruptions meets an internal resistance to do the hard, skillful thing, and I’ll spend the entire morning (my most creative hands-on-keys time) working through small tasks, catching up on email, responding to that DM on Instagram, talking over a land project with mom and dad.
Is this stuff necessary? Of course. And, if I’m honest with myself, days like these are the ones that I go to bed feeling a subtle dissatisfaction and incompleteness running through my body. Even if I got a lot done, I know deep-down I didn’t do the thing I really wanted and needed to do for the day. I didn’t make my art.
And I’ll say something about the word art in case you read these Saunters and wonder, “Thomas is running a men’s leadership business. Why does he keep talking about his art? Dude ain’t Van Gogh.”
The etymology of art is “to fit together” from the PIE root *ar*.
I think one of the most disempowering stories of our culture is that only a very few of us are artists. I think art is the way each of us make sense of the world we live in. It’s a fitting together of the fragments. Whether that’s creation art that comes from the caves of 30,000 years ago. Or the critique of modern industry if you’re Andy Warhol.
When we’re in touch with what’s most important in our lives, however we bring that forth is our art.
The thing I find about what I call my art—the precise, cultivated, inspired expression of my gift—is that it takes work. On my best days—the days I do show up for what really matters—I have to work for it. It doesn’t come cheap.
I have to be present to this moment, undistracted, and able to distill, discern, and ultimately dictate the inspirational current that’s ineffable until someone “catches it” and brings it through.
The deep fulfillment comes from doing the work. From not distracting during a moment where I stall and focused, patience finally leads to the creative breakthrough. From connecting the dots of something I learned three years ago with something I experienced yesterday that I am now seeing to weave into one of the initiations of the Living Leadership arc.
So when this expression and cultivation of what matters most takes real work, and there are a thousands taps on the shoulder into something more “urgent” or immediate or dopamine-filled, it asks a lot to keep showing up for the thing.
And, I don’t actually think it’s because most of us are lazy. Or that we don’t want to do the good, hard work.
I see a lot of men in my life—quite gifted, charismatic, caring, who are really good at what they do, willing to work their asses off, but they’re not doing the thing that’s actually most important to their souls. And deep-down, they know it. And if they don’t yet know it, their bodies do. I know more healthy men in their 30s and 40s than I’d like to with some chronic body challenge that doesn’t add up given the health of their physical lifestyle.
And this has me asking: why do we avoid moving towards what is actually most important?
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In 2023, I started working on what I thought would be a Substack post around my first 16 seasons living on land (which was totally foreign to me when moving here from a suburban childhood and a decade in cities in adulthood).
I wrote, and I kept writing over the next 2 years (Andrew and Maren, y’all are the only two I believe have seen this piece out of my respect for you both as writers). It’s now 70+ pages, still sitting in my Notion unpublished, and perhaps it will become the foundation of my first book one day.
In the piece, one of the threads I pull on Is around our severance from relationship to land. I ask why it’s so challenging in this day and age to claim belonging to a place in a way that says we want our people to be there for centuries to come.
Spoiler alert if you were waiting on the edge of your seat for my first book: I end up landing on the vulnerability it is to stake such a claim. Given what almost all of our ancestors experienced at one time or another in losing the places we most loved when Empire arrived on our shores, there’s something almost safer around not letting ourselves love and rely upon a place so deeply. We’re protecting against experiencing that same hurt.
I share this because my hunch is that it’s a similar reason as to why so many of us will not actually claim and live as an expression of what matters most. Why so many of us will go days, weeks, months, and then years doing what we need to do—maybe even what looks good externally—without doing the actual thing.
There is something quite vulnerable in saying to one’s self and then the world: this is what matters most to me. This is the hill I am here to live on and die on. And, I am going to take my very best shot at fulfilling and expressing what’s most important to me.
And I will inevitably stumble and have hard days and forget, and you will be able to point fingers and laugh if you choose. There will be days where I wonder if I can pay the bills, and I’ll see photos of friends from college in an epic villa on the Adriatic Coast eating $150 seafood. But fuck, this is what actually matters most in the depths of my being and I’m going to claim it.
If you’re brave enough to claim this from the culture in which we’ve come, goddess bless you. It’s not the norm.
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So, we have what matters most, our life’s work. Now…the chaos.
The beginning of Living Leadership Is drawing near. Yes, it’s a program you pay to participate in. But equally so, I hold its creation and cultivation as my best attempt at making a masterpiece. It’s the culmination of 15+ years of self-inquiry and devoted practice, five years of leading men’s spaces, and a fucking rad frame and 8-month arc for stepping into self-leadership on behalf of what matters most to us in these times.
It’s been hard work in getting here. The kind of hard work that asks something of me every day when I show up to my desk to work. And the kind of hard work that asks for a precision and discipline in how I carry myself and my own leadership outside of work.
I’m proud of this process the past 6 months because I see it as the closest I’ve ever been to giving shape to that which is most true to who I am. I see how meeting the hard, challenging, uncertain edges of the past years has allowed me to actually steward and create something of this potency.
And as I get to this place in my art, I’ve noticed that there are 4x as many interruptions, distractions, and chaotic pulls as there were a year ago. It seems I’m being given every legitimate excuse to avoid stepping into the full expression of this gift, the nearer I find myself to it.
I shared in last saunter around some intense jaw/gum pain. It turned out to be a gnarly infection that had started in a pocket unreachable by brushing + flossing underneath a wisdom tooth. Long-story short, I ended up needing to get all four wisdom teeth out—certainly the most intensive surgery I’ve had in my life to date.
In this same window of trying to get the infection at bay and then recovering from the extraction, the waves came crashing on shore.
In the middle of a work day, I ran up to the pasture as a neighbor had a quick window to help me with something. Moving a round bale of hay in the pouring rain in sandals (I was in my work clothes), I stepped in a fire ant nest and no joke, ended up with 50 bites on my left foot. My left foot swelled to double the size of my right while my right jaw was double the size of my left.
In these same days, we had a duck attacked by a bobcat and have her back ripped open. Our den wall started pouring water during a big summer’s rain. Sleep has been terribly off with the pain + a rough week for our son’s digestive system. One of our steers, Curly, has gotten out of the fencing twice after 10pm after we had gone to bed. My poison Ivy from last year has been flaring up. We had a tree fall in front of our house in Wednesday’s summer storm. Some of the closest people in my life have been going through it and reaching for support.
And goodness, the persistent headache and fogginess from having four teeth ripped out of my jaw.
It’s just been one of those chapters where no day has gone as I anticipated, nor has offered as much time as I’d like to be spending on what matters most, nor where rest has been abundant.
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I have to be careful of the meaning I make in times like these. When I’m depleted and things feel hard, I notice a story sets in that somehow I—and my decisions—are responsible for the chaos that ensues. That somehow it’s a testament to who I am or how I’m showing up.
There’s another story that comes—one that’s less self-critical but equally dis-orienting: that I need to make changes to the external circumstances of my life. That I ultimately can exert more control to have more agency for things to go the way I want.
There is a time for this reflection. There is a time to ask: what decisions—contracts—have I entered into in the past that aren’t actually in integrity with how I want to meet life?
But that’s only one layer of what’s happening right now, and if I’m honest, I’ve spent most of my life exerting my will over my environment to have more internal peace.
What I see happening right now, underneath those currents of self-criticism or questioning of choices around lifestyle, something deeper is beckoning.
I’m being asked to stay in the current of what matters most no matter what the circumstances of Life bring.
There is a way—and I indeed know it from my best days—where I imbue everything I’m doing with that precise expression of who I really am.
The hard work I speak of in bringing forth what matters most—that same level of devotion, discipline, and consistency can be brought to how I meet any moment.
Especially the moments where things are not going the way I expected or wanted them to be.
And guys, this is brave and big work for any of us to be doing. To be in touch with something precious. To have a vision for something important and beautiful. To be willing to give everything for it. Daily. But to have the capacity to hold onto the thread even when that precise vision doesn’t take the form you thought. Or when the really big waves coming crashing on a stormy day.
This is the work to me that changes our world. If we, as men, could consistently go forth in touch with what matters most, with enough courage enough to express it, we’re going to create a world for our children where what is good, true, and beautiful is ever-present.
What matters most to you—that golden thread I like to speak of—contributes to that fucking awesome, magnificent world we know in our bones is possible.
So, as I move nearer and nearer to my expression of what matters most in the creation and leadership of Living Leadership, I’m asked to imbue all aspects of my life with that same quality of warmth, knowing, and vibrancy.
I’m not ready to say what this chaos is. Maybe it’s totally random and just a byproduct of being alive right now. Maybe it is indeed a mirror to decisions I’ve made that want re-defining. Maybe it’s the threshold guardians testing me as I move into a more powerful expression of what matters most.
What I can say right now is that I have the opportunity in these days to meet the chaos with my art. To keep showing myself and life that I really believe in what’s coming through the masterpiece that is Living Leadership by how I live it.
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I’ll close with a brief story.
One of the books I’m reading right now is The Evolved Nest. If you’re a geek for ancestral ways, evolutionary biology, and the reminder of the perfect blueprint of life Nature has given us, it’s good. And quite scientific.
The authors open the book with a story that I am intentionally going to share from memory without going back to the introduction.
They tell of a famous woman from the west who went to spend a year with a local tribe in the 70s before these people had any contact with the modern world. It was either in East Africa or the Amazon.
Each day, there was a group of men whose job it was to take a big canoe down a steep mountain into a body of water, fish, and then bring the canoe back up. The slope, as she describes it, was not one any sane, modern person would try to traverse with a 500+ pound canoe. But, this is the way these people had to get to the water and back.
(The story doesn’t make clear why the canoe couldn’t just stay at the bottom of the slope, but I assume there was a reason).
Getting the canoe back up was the real work. For every step up, it seemed they’d take two steps back. This woman describes herself and the other westerners as being extremely irritated for the first weeks of this daily chore. Here they were trying to help these people, and they were spending hours bringing a canoe up an entirely inefficient path.
She describes being particularly agitated because the local men would spend the entire duration of the canoe-dragging in a state of laughter and play. They would celebrate every step forward, and they’d giggle and joke at every step back.
The way I read it: eventually this woman came to see that these men were committed to this daily, arduous chore being a good thing. The canoe dragging was not an impediment to what they wanted to otherwise be doing. It was the thing, itself. It was the expression of what mattered most and who they really were in that moment in time.
And so they gave it everything they had, especially when things were going “backwards.”
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I have a challenge of sorts for the week. A challenge to engage your own version of this canoe.
Phil Stutz, the renown coach + therapist, has a concept know as the Death Cookie. He defines it as the scary thing we’ve been avoiding that we know we need to do.
I like to see them as places in our life where there’s an enormous store of energy. Something has been wanting/needing to happen, and we haven’t said yes. Perhaps because we’re scared of what’s on the other side, we don’t believe we’re capable, or we just dread the idea of showing up for it.
My experience is that when we “eat the death cookie,” all of that stored energy comes online and we’re propelled forward with momentum towards what is most important to us. We eat a lot of Death Cookies together in Heart of Men.
Inside the chaos of these past weeks, I’ve been eating death cookies. There’s some stuff that has to be tended and put into greater integrity as I step into this next threshold of my leadership. I’m seeing the chaos, when engaged, as the energy to ultimately provide more momentum when things inevitably come back into order.
This week my invitation to you: Eat a Death Cookie. Invite in a friend so there’s some accountability and shared mission. The catch: at each step of the way, imbue what you’re doing like you’re making a masterpiece. Like you’re creating your life’s greatest work. Give it that level of care, focus, and skillfulness. See what happens.
If you actually do this, write to me before next Saunter. I want to catch your story and find some way to honor and uplift you.
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We are headed up to the Mad River Valley and Lake Champlain for a family trip with some of my best friends and their families. When I get back, the doors officially open for Living Leadership.
Here’s what I’ll say: if you’re interested, get on the waitlist. Because: when I get back, I’ll do a 1-hour, 1:1 call with you. It’s not to convince you to join. It’s to help you get so clear on where you are right now in Life, what’s possible, and what you’re needing to get there. Even if we decide it doesn’t align for you to join Living Leadership, you’re going to get meaningful guidance and inspiration from the conversation.
If you’re not on the waitlist, you will go through an online application process. If you’re on the waitlist, we’re going to get to drop in deep together. So if you’re even halfway curious about this masterpiece that is Living Leadership, take the 60 seconds to join our waitlist.
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Y’all are awesome. Keep doing the good work out there. Especially the work inside your own heart that no one can yet see but one day you’ll be known and loved for. The really good stuff takes time. You’re worth it.
Td
