The mens circle I am a part of goes the same each time. We vow to hold space for our fellow brothers, to see them, and to be authentic in how we show up today. Then, we do a quick check-in. Two to three words max of what's alive for you. Good or bad. Once everyone has checked in, we move onto the prompt. All pretty standard for a group like this.

A couple weeks ago, a prompt came up that has been on my mind lately. The prompt was "When have you thought you were being a leader only to find out your leadership was misguided or misguiding and what happened?" Followed by "How do you see yourself as a leader today and how to do you hope to lead in the future?" We were given 5 min to jot down some notes and think.

At first, I drew a blank. There have been few times in my life where I had made an effort to lead something, but I’ve never really seen myself as a leader. I’m not the kind of guy who jumps up and says, “Follow me!”.

It’s not that I’ve actively avoided it, I just think that it's something I’ve never trusted myself enough to claim. Maybe it's lack of confidence? A shitty self-image? Something else? I was always of the belief that I wasn't meant to take up space and that leadership was for other people... The loud and confident ones... Not me. As I sat there though, combing through my experiences. It’s not that I’ve never been a leader, it’s just that I’ve only ever been one when someone else decided I should be.

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Okay, so with that in mind, when I was being a leader (whether forced or not), did I lead from the heart in those moments? If I didn’t, why not? What does that even look like?

The five minutes ended, and I still hadn’t settled on an example. I held my breath, hoping not to be called first. I wanted to speak, but I needed to hear someone else’s story first, to see if it would spark something in me. To my joy, the day's facilitator said you only needed to share if you felt compelled. Nice.

As I listened to the first man talk, I went back to my train of thought. Why have I so often been placed into this position? I'm so often thrown into moments where a group of people will look at me and energetically tell me "what do we do?" or "what do you think?”

I started to spiral a little. Is it the way I carry myself? Is it written on my forehead? If we want to get esoteric about it, my life path number is 1, and according to that, I'm natural-born leader. I'm also a Sagittarius rising, making me optimistic, fiery, expansive. Lastly, I was born on a Thursday, which is Jupiter’s day, the planet of abundance and leadership. To a certain extent, it makes sense. But, esoteric things aside, there is also something undeniable about how people react to me. I’ve been told many times that my words carry weight and that people value my opinion, presence, and ideas.

It’s not something I tried to cultivate either (at least, not consciously). It’s just there. And yeah, I’d say I’m good with people. Years in sales and consultative has sharpened my ability to connect, to read a room, to understand what resonates. Causing me to build up this unspoken social currency if you will. It’s flattering, but also strange, like there’s this version of me other people see that I’m still trying to catch up to.

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Now, from the lens of leadership? That's a different story. You see, when I'm thrown into the spotlight, I (like anyone might) get a boost in confidence. Because of this though I fall into a trap that I wasn't even aware of… People pleasing.

As a kid, I learned that being “good” was about being what others needed, not being myself. Proper manners and polite smiles, all carefully rehearsed to ensure I took up less space and didn’t inconvenience anyone. Because of this, I became a master at shrinking myself, a kid whose value was measured only by how easy I could make life for others despite myself.

Looking back, I laugh at how much effort I put into erasing parts of myself to keep the peace. A whole personality on standby, ready to morph into whatever just in case someone needed me to be someone else. People praised me for it too, which made it so much worse. “Such a polite boy,” they’d say. Not knowing the tightrope I was walking in making sure everyone else was okay and appearances were met while leaving my own needs behind. It honestly explains the absurd arc that was my college days…but that’s a story for another time.

It’s not tragic. It’s just the hand I was dealt as a kid. You don’t get to ask for a redo.

That’s the wound I’ve been dragging with me ever since. Appearances first, authenticity last. And now, every time I’m in a leadership role, that wound rises again like muck I can’t clean off, reminding me it’s easier to please than to lead.

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The man had finished talking and all eyes were on the screen, who was going to go next? I started to hesitate, with that little voice whispering: “maybe I won’t say anything.”

But that…that right there. There it was. The wound, rearing its head. I noticed it immediately and thought, Fuck it. I’m going to say what I need to say.

I started speaking, nervously because I was unsure if what I was saying would land. But then, like it always does, it hit. In fact, it struck gold. My story resonated, visibly, with so many of the men. The entire vibe of the meeting shifted as my words dug up memories in other men. Private messages poured in afterward, with men telling me I’d made them realize deep things they’d never considered.

And there it was again, the power I hold to share ideas that stick. Except this time, it was different. This time, it wasn’t about saying what I thought people wanted to hear. It was me. Speaking from the heart. Speaking from my center.

I turned to the second part of the question: how I want to lead in the future.

It reminded me of a book I recently read, The 15 Commitments of Conscious Leadership by Jim Dethmer, Diana Chapman, and Kaley Klemp. Specifically, Commitment 5: “I commit to saying what is true for me, to being a person to whom others can express themselves fully, and to eliminating gossip.”

I told the group that for so long, I’d led from a place of people pleasing and keeping the peace at the expense of my authenticity. But I’ve realized that true leadership for me at least, is about that balance: speaking with conviction while staying open to perspectives that challenge my own. That’s the kind of leader I hope to be.

As I wrapped up, I looked around the group and felt the weight of their attention. In that moment, I learned my last lesson...Leadership is something you step into, moment by moment. It’s not given to you. It’s not about being perfect. It’s about showing up as yourself and inviting others to do the same.

It’s crazy beautiful in my own romantic way. That day, by stepping into my center and speaking from a place I’d spent years hiding, I let myself be seen. And in that moment, I wasn’t just describing the leader I hope to be… I was becoming him.

Share

The mens circle I am a part of goes the same each time. We vow to hold space for our fellow brothers, to see them, and to be authentic in how we show up today. Then, we do a quick check-in. Two to three words max of what's alive for you. Good or bad. Once everyone has checked in, we move onto the prompt. All pretty standard for a group like this.

A couple weeks ago, a prompt came up that has been on my mind lately. The prompt was "When have you thought you were being a leader only to find out your leadership was misguided or misguiding and what happened?" Followed by "How do you see yourself as a leader today and how to do you hope to lead in the future?" We were given 5 min to jot down some notes and think.

At first, I drew a blank. There have been few times in my life where I had made an effort to lead something, but I’ve never really seen myself as a leader. I’m not the kind of guy who jumps up and says, “Follow me!”.

It’s not that I’ve actively avoided it, I just think that it's something I’ve never trusted myself enough to claim. Maybe it's lack of confidence? A shitty self-image? Something else? I was always of the belief that I wasn't meant to take up space and that leadership was for other people... The loud and confident ones... Not me. As I sat there though, combing through my experiences. It’s not that I’ve never been a leader, it’s just that I’ve only ever been one when someone else decided I should be.

Subscribe now

Okay, so with that in mind, when I was being a leader (whether forced or not), did I lead from the heart in those moments? If I didn’t, why not? What does that even look like?

The five minutes ended, and I still hadn’t settled on an example. I held my breath, hoping not to be called first. I wanted to speak, but I needed to hear someone else’s story first, to see if it would spark something in me. To my joy, the day's facilitator said you only needed to share if you felt compelled. Nice.

As I listened to the first man talk, I went back to my train of thought. Why have I so often been placed into this position? I'm so often thrown into moments where a group of people will look at me and energetically tell me "what do we do?" or "what do you think?”

I started to spiral a little. Is it the way I carry myself? Is it written on my forehead? If we want to get esoteric about it, my life path number is 1, and according to that, I'm natural-born leader. I'm also a Sagittarius rising, making me optimistic, fiery, expansive. Lastly, I was born on a Thursday, which is Jupiter’s day, the planet of abundance and leadership. To a certain extent, it makes sense. But, esoteric things aside, there is also something undeniable about how people react to me. I’ve been told many times that my words carry weight and that people value my opinion, presence, and ideas.

It’s not something I tried to cultivate either (at least, not consciously). It’s just there. And yeah, I’d say I’m good with people. Years in sales and consultative has sharpened my ability to connect, to read a room, to understand what resonates. Causing me to build up this unspoken social currency if you will. It’s flattering, but also strange, like there’s this version of me other people see that I’m still trying to catch up to.

Share

Now, from the lens of leadership? That's a different story. You see, when I'm thrown into the spotlight, I (like anyone might) get a boost in confidence. Because of this though I fall into a trap that I wasn't even aware of… People pleasing.

As a kid, I learned that being “good” was about being what others needed, not being myself. Proper manners and polite smiles, all carefully rehearsed to ensure I took up less space and didn’t inconvenience anyone. Because of this, I became a master at shrinking myself, a kid whose value was measured only by how easy I could make life for others despite myself.

Looking back, I laugh at how much effort I put into erasing parts of myself to keep the peace. A whole personality on standby, ready to morph into whatever just in case someone needed me to be someone else. People praised me for it too, which made it so much worse. “Such a polite boy,” they’d say. Not knowing the tightrope I was walking in making sure everyone else was okay and appearances were met while leaving my own needs behind. It honestly explains the absurd arc that was my college days…but that’s a story for another time.

It’s not tragic. It’s just the hand I was dealt as a kid. You don’t get to ask for a redo.

That’s the wound I’ve been dragging with me ever since. Appearances first, authenticity last. And now, every time I’m in a leadership role, that wound rises again like muck I can’t clean off, reminding me it’s easier to please than to lead.

Subscribe now

The man had finished talking and all eyes were on the screen, who was going to go next? I started to hesitate, with that little voice whispering: “maybe I won’t say anything.”

But that…that right there. There it was. The wound, rearing its head. I noticed it immediately and thought, Fuck it. I’m going to say what I need to say.

I started speaking, nervously because I was unsure if what I was saying would land. But then, like it always does, it hit. In fact, it struck gold. My story resonated, visibly, with so many of the men. The entire vibe of the meeting shifted as my words dug up memories in other men. Private messages poured in afterward, with men telling me I’d made them realize deep things they’d never considered.

And there it was again, the power I hold to share ideas that stick. Except this time, it was different. This time, it wasn’t about saying what I thought people wanted to hear. It was me. Speaking from the heart. Speaking from my center.

I turned to the second part of the question: how I want to lead in the future.

It reminded me of a book I recently read, The 15 Commitments of Conscious Leadership by Jim Dethmer, Diana Chapman, and Kaley Klemp. Specifically, Commitment 5: “I commit to saying what is true for me, to being a person to whom others can express themselves fully, and to eliminating gossip.”

I told the group that for so long, I’d led from a place of people pleasing and keeping the peace at the expense of my authenticity. But I’ve realized that true leadership for me at least, is about that balance: speaking with conviction while staying open to perspectives that challenge my own. That’s the kind of leader I hope to be.

As I wrapped up, I looked around the group and felt the weight of their attention. In that moment, I learned my last lesson...Leadership is something you step into, moment by moment. It’s not given to you. It’s not about being perfect. It’s about showing up as yourself and inviting others to do the same.

It’s crazy beautiful in my own romantic way. That day, by stepping into my center and speaking from a place I’d spent years hiding, I let myself be seen. And in that moment, I wasn’t just describing the leader I hope to be… I was becoming him.

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