Marcus had made his decision. He was restructuring his sales team, moving from geographic territories to account-based pods, and he'd landed on it after three weeks of analysis and conversations with his team. Then he drove two hours to his regional office, where his leadership team was waiting to hear the plan, with a leadership podcast queue running the whole way.

By the time he arrived, he wasn't sure anymore. One guest swore by geographic territories. Another dismissed account-based models as a fad. A third talked about a completely different structure that had "10x'd" a company Marcus had never heard of. He walked into that meeting, stood in front of the people waiting for his decision, and tabled it. Six weeks later, nothing had changed except his team's confidence in him.

Nothing in those episodes was wrong. That's what made it dangerous.

Good leadership content is a menu. It's a set of ideas someone tested in their own kitchen, with their own ingredients, for their own guests. It was never meant to be a prescription you fill without a diagnosis.

The trouble starts when we forget that. An idea gets presented with total conviction, because conviction makes for good audio, and we hear it as a rule rather than a data point. Marcus didn't need a new plan. He needed permission to trust the one he already had. What he got instead was doubt, dressed up as insight.

Doubt like that erodes the confidence decisions require. A leader who dithers isn't being thoughtful. They're borrowing someone else's certainty and finding out the hard way that it doesn't fit.

Copying the Form, Missing the Substance

Physicist Richard Feynman told a story about islands in the Pacific after World War II. During the war, these islands had airstrips, and planes landed loaded with supplies. When the war ended and the planes stopped coming, some islanders cleared their own runways, built control towers out of wood, and carved headsets from coconuts. They went through every motion they'd observed. No planes ever landed.

Feynman used it to describe science that imitates the form of rigor without the substance. It's just as useful for leadership. The 5am routine, the specific meeting cadence, the exact phrase a famous founder used to fire someone gracefully. These are the runway and the control tower made of wood. 

What actually made them work was everything invisible: years of trust already built, a specific market moment, a team that had seen this leader come through for them before. Copy the visible ritual without the invisible substance, and you're not landing planes. You're wearing a coconut headset, waiting for something that was never coming.

There Is No One Right Way

This isn't new territory for organizational thinking. Back in the 1970s, researchers Paul Hersey and Ken Blanchard proposed what became known as situational leadership: the idea that there is no single best style, only styles that fit or don't fit the person and moment in front of you. A directive approach that helps a brand-new hire find their footing will suffocate someone with fifteen years of experience. A hands-off, collaborative style that unlocks your most seasoned person can leave someone still building skill feeling abandoned.

The specific model matters less than the premise underneath it. Effective leadership is a function of fit between you, this person, this team, this moment, not a formula you import from a case study.

Every organization is its own organism. Two companies can share an industry, a size, and a developmental stage and still be nothing alike, because the people, the history, and the trust in the room are never the same.

Trying It On Instead of Trading Places

None of this means tune it all out. The answer is to change how you listen.

Researcher Herminia Ibarra studied how leaders actually grow and found two common pieces of advice fall short. "Just be yourself" leaves people stuck, repeating patterns that stopped working years ago. "Copy what works for them" leaves people performing a version of leadership that was never theirs to begin with. 

Real development, she found, happens through adaptive authenticity: trying on a piece of what someone else does, testing it in your own context, keeping what fits, and letting the rest go. Interestingly if you've watched children develop their personalities you probably noticed them play-acting to find out what fits. It's not the same thing, but an adult version of this. We can try out ideas but also need to be very aware of their fit and the feedback we get from others.

That's a completely different posture than the one Marcus had in his car. He wasn't trying anything on. He was trying to trade his whole outfit for someone else's, based on secondhand advice tailored to a life that wasn't his.

What I Actually Do

I'll tell you plainly: I don't think it's my job to tell a leader they're doing it wrong. I've watched prescriptive coaching work, briefly, in narrow situations, and then quietly stop the growth it was supposed to produce. A leader who's been told the answer stops building the muscle that finds answers. The org stops developing judgment and starts waiting for the next directive, whether it comes from me or from whoever they listened to on the drive in.

What I offer instead are ideas. 

Things I've lived through, patterns I've seen across four decades of my own businesses and my clients', frameworks that have held up. Then I get out of the way and let the leader in front of me figure out what applies, what doesn't, and why. That's slower. It's also the only version that actually builds someone to no longer need me, or the next podcast, six months from now.

Don't get me wrong I can ask some very tough questions when a leader seems to be going against their best interest, but my different opinion doesn't make them wrong, and I've seen them avoid the pitfall I had imagined enough times to prove that out.

A Few Filters Worth Keeping

When something lands hard in a book or an episode, three questions are worth asking before you act on it:

Does this fit the specific people I lead, or more so the people the speaker led?

What conditions made this work for them that I don't currently have?

Am I drawn to this because it's true for me, or because it sounds certain and I'm tired of not being certain?

There are real common threads across good leadership. Clarity, consistency, and follow-through show up again and again for a reason. But the threads are a starting point, not the finished garment. The moment you stop tailoring is the moment good advice starts working against you.

What would change if you treated the next piece of leadership advice as one idea in a room full of them, rather than the one you'd been missing?

When I get sick, I take it seriously. I rest. I drink fluids. I pay attention.

When I tweak my back lifting something wrong, I see someone. I do the exercises. I let it heal.

When I eat something that doesn't agree with me, I notice. I probably won't eat it again for a while.

Physical discomfort, I honor. I treat it as information.

But psychological discomfort? For most of my life, I had a different relationship with that one. And I see it everywhere I look.

When something feels off in a conversation, we talk over it. When tension builds in a relationship, we get busy. When a feeling shows up that we don't want to feel, we distract, defend, or rationalize it away.

We've gotten very good at not feeling what we feel.

Fifty Years of Going Toward It

For nearly fifty years, I've been showing up to do this work in one form or another.

Men's rite of passage gatherings. Yoga intensives. Meditation retreats. Movement trainings. Shamanic practices. Process groups. Long conversations with individuals where the only real agenda was telling the truth and seeing what happened.

All of it, in different ways, designed to do the same thing: take me deeper into the patterns and beliefs that form who I am and how I behave. Expose the soft underbelly I'd otherwise spend a lot of energy keeping covered.

What I learned, over and over, was simple:

Unfamiliarity breeds fear.

The parts of myself I didn't know — the reactions, the defenses, the inherited beliefs running quietly underneath my decisions — those were the parts that had power over me. The more familiar I became with my own psychology, my own wiring, my own conditioned responses, the easier and more comfortably I could move through life.

And the more familiar I became with the same dynamics in other people, the more present I could be with them, even when what they were going through was hard.

The strange paradox of this work is that going toward discomfort, again and again, made me more comfortable in my own skin. Not less.

What I've Learned to Trust

Here's something I've come to believe deeply:

Discomfort is often at its greatest right before something breaks open.

Right before the answer comes. Right before a relationship turns a corner. Right before you finally see the thing that's been tripping you up for months, or years, or sometimes most of your adult life.

I've watched this in myself. I've watched it in person after person I've worked with. Peak intensity isn't a sign that things are getting worse. It's often the last resistance before something gives way.

The mind doesn't know that. The mind reads peak discomfort as proof that this approach isn't working, and pushes us to abandon the thing right at the moment it was about to teach us something.

Being With Someone in Theirs

I want to tell you about someone who worked for me once.

She came into my office on a difficult morning, carrying something heavy from her personal life. She didn't ask for advice. She didn't really ask for anything. She just needed somewhere to bring what she was feeling.

I didn't try to fix it. I didn't redirect the conversation. I didn't offer solutions or perspective. I just sat with her while she felt what she was feeling.

That was the whole thing.

She still mentions it to me, years later. Not because I said something wise. Because I didn't try to make her discomfort go away.

It took me a long time to understand that being with someone in their discomfort, really with them, is one of the most generous things a person can offer. And it's only possible if you've practiced being with your own.

You can't sit with what you haven't sat with.

What I Almost Missed

Years ago I was working with a leader who was stuck. Genuinely stuck. He had done everything he was supposed to do. Strategy. Communication. The right hires, the right structure, the right moves. And something was still missing in how his team showed up.

For weeks, our conversations got harder, not easier. He kept asking what to do. I kept asking him what he was feeling. He resisted that. He wanted a solution. He didn't want to feel what was underneath.

And then one afternoon, in the middle of yet another loop, something shifted. He got quiet. He sat back. And he said something he hadn't said in any of our previous sessions, about a fear he'd been carrying since childhood about not being enough.

That was the block. Right there. The whole thing.

He didn't need a new strategy. He needed to feel the thing he'd been spending his whole career trying to outrun.

The discomfort was at its greatest right before it gave way.

The Body Already Knows

What I find interesting, and what the neuroscience increasingly supports, is that the body usually knows before the mind does.

The tightness in the chest. The held breath. The restlessness that shows up when you're avoiding something. The way your sleep changes when there's a conversation you keep meaning to have.

Those signals aren't random. The nervous system is telling you something needs attention. The same way your back tells you you lifted wrong, or your stomach tells you that food was off.

Physical discomfort, we honor. We rest, we recover, we adjust.

Psychological discomfort, we override.

The body doesn't know the difference. The signals come from the same place. The rest, the recovery, the adjustment work the same way. The only difference is that the practice happens in stillness rather than stretching.

What Keeps Me Going Back

I'm not going to tell you discomfort is fun. It isn't. After almost fifty years of this work, I still resist on some days. The pull to look away is strong and it never fully goes away.

But I keep showing up. To the groups, to the practices, to the smaller moments inside the rest of my week where something difficult wants my attention and I have to choose whether to feel it or escape it.

What I can tell you is that almost everything that's mattered in my life and my work has come through the doorway of discomfort. The relationships that lasted. The clarity that finally arrived. The blind spots that finally became visible. The conversations that took years to have, and changed everything once I had them.

The discomfort wasn't the obstacle.

It was the path.

What's an uncomfortable thing in your life right now that might be closer to resolution than it feels?