The Real Reason Men Feel Like Frauds, and Why Confidence Won't Fix It
- 40 minutes ago
- 14 min read
Daryl Henderson is a master coach, facilitator, and artist known for blending spiritual traditions, shadow work, and leadership training. He is the co-founder of Odyssey of Man, the creator of True North Coaching, and the founder of One11, a health & wellness brand.
There are seventeen men in the room and every single one of them is looking at me. We had been building toward this weekend for months, through the calls and the planning and the logistics and the endless back and forth about what it was going to be and who exactly it was for.
Now it's here, and everyone is sitting on the floor in a circle, and the phones are in a box somewhere in another building. We're doing the usual logistics you do at the start of these weekends, going around, saying who we are, and laying out what we're going to cover over the next two days. I'm nervous.
It's the kind of nervousness that sits somewhere behind my sternum and makes my voice come out a half step higher and a little shakier than it should. You've probably felt it before. It's when you can hear yourself being nervous and sounding off while you're doing it and still can't stop.
Here's what's running in the back of my mind the whole time I'm talking as one of the leaders of this experience. "Oh shit. Here we go. Now they'll get to see that I have no idea what I'm doing."
"What if I piss one of them off and I don't know what to do? Then what?" "This was a bad idea... Oh well. I guess we'll see what happens now." There's more, but those are the ones I remember the most.
I have been in transformational work since I was twenty-five, and by then I'd sat in more circles than I could count, done trainings galore, put in years of my own inner work through self-inquiry and meditation, and been broken open and put back together enough times that none of what was about to happen in that room should have felt unfamiliar to me. By every measure that matters, I had earned the right to be standing where I was standing. I was certain, right up until the moment that circle opened, that I was about to be found out as a phony.
So what gives?
Everybody has a fix for this feeling, and I've tried a metric ton of them.
Just do a quick search for "imposter syndrome," and you can spend the next five years watching YouTube videos and reading articles about how to solve for it.
Fake it till you make it. Stand up straighter. Stick your chest out just "2 mm". Remember your credentials, write down your wins, and notice all the evidence that contradicts the story you're telling yourself. There is an entire industry built on the premise that if you could just believe in yourself a little more, everything would shift and you'd walk into rooms looking and feeling like a man who belongs in them. Someone who's strong, confident, and in control. If you haven't realized this already, then I'm going to break it to you. The world does not need that. It needs you!
Anywho, I digress. The simple fact is that some of these techniques do work, for a while or maybe just for an afternoon, and they are not wholly unuseful. But rarely does one of them touch the thing underneath that is causing the issue in the first place. As can happen in modern Western medicine, we've become exceedingly good at finding the symptom and treating it without ever getting to the root cause. The advice and remedies aren't necessarily bad, they just aren't asking the right questions. I've learned that if you want to improve the quality of your life, improve the quality of your questions.
In my experience, the imposter feeling many men experience isn't actually a confidence problem, as we've been told over and over again. It's a "not knowing who you are" problem. So instead of asking, "How can I fit in and be accepted more?" the question becomes, "Who am I really, and where do I actually want to be?"
Those two things are not the same, and understanding the difference between them matters more than just about anything else I could tell you here.
Imagine you're a gray wolf who was raised among gray foxes
You look similar. You're in the same family, with roughly the same silhouette, four legs, a tail, and a decent set of teeth. From any distance at all, nobody can tell the difference, aside from your size. But so what?! You're fluffy and enjoy the same foods, and you get along great with your brothers and sisters.
But your nature is totally different. You don't look or sound like everyone else around you. The way you hunt and eat is different, and your coat looks different too. Yet you're trying to pretend that it isn't, so you put on a fox costume just to fit in and be more like everyone else. What almost nobody tells you is that the costumes actually work.
So you learn to make yourself smaller in a room, because that's what foxes do. You learn to be clever instead of saying the direct thing that's sitting right there in your chest. You go quiet in the exact moment something in you wants to howl, and you learn to move alone and call it independence, because a fox doesn't need a pack and you are supposed to be a fox now. You get good at it too. Good enough that they take you in and accept you.
That last point is worthy of stopping and looking at for a second, because a wolf pretending to be a fox will spend his whole life telling everyone he doesn't need anybody. He'll be proud of it. He'll build an entire identity out of not needing anybody, and then wonder at forty-five why there's nobody to call.
Nobody has ever caught you at any of this, which most of us read as proof that we're pulling it off and that we've finally arrived, when really all it proves is how much work we've put into the disguise and how convincing we've gotten with it.
The whole time, every hour you spend inside the pack, you are translating. Running everything through a conversion layer, checking your output against what a fox would do here, carrying a load nobody else in the room can see you carrying. That is exactly why nobody has ever been able to reassure you out of it. It becomes so automatic that at some point you don't even know you're doing it. But you know, deep down you know, there's something "not quite right" here.
You often get great reassurance that the costume you're wearing looks good, and therefore you now have the validation that you're doing a good job and you belong here. The costume doesn't need reassurance... The costume is doing great. The problem is that no matter how hard you try, it's just not you, and you know it. Until you do something about it, it'll eat away at you.
What the costume is usually made of
I can tell you what mine was made of, because I've had a long time to sit and look at it.
For me, it was mostly borrowed vocabulary, language I picked up from teachers I admired and delivered in a cadence that was never actually mine, along with a set of frameworks I'd been taught early in my personal growth journey and never once questioned because questioning them would have meant admitting I had no idea what I'd put in their place.
Coupled with the belief systems I grew up with around "being a good boy" and not wanting to disappoint anyone, this was a tricky mix. In high school, I just wanted to be "one of the boys," play football, and go out with the hot cheerleaders. But that wasn't me. I was weird, awkward, and not that good-looking. I liked metal and electronic music and wearing tie-dye T-shirts with Grateful Dead bears on them. I was a walking contradiction, a rebel, and so I went the total opposite direction and got in with the freaks and geeks.
Then I got really good at that game. All the while, I was still hiding parts of me that I didn't want anyone to see. Then, in my mid-twenties, I found the "holy grail"... insert angel sounds and trumpeting... I found transformational work. Lo and behold, this was my way to be special. Now I knew something everyone else didn't. So the courses and breakthroughs stacked up, and whilst I learned more and had powerful healing experiences that truly changed my life, I also gained more and more tools that showed me how to be a better person. At least for a few weeks. Then the high of the breakthrough wore off and became more of an ego trip than a lasting change.
Fast forward ten years and, underneath all of it, I still had an impression of the man I thought was supposed to be leading from the front of a room like that one. I thought that man needed to be calm, composed, and certain, someone holding the answers, someone who had done the work and come out the other side clear and was now generously handing down what he'd found. I wrote about a version of this once, in a different context, and one of the lines from that piece still stands true. I was a new age conscious man who had it figured out, or so I thought. The trouble is that I was good at all of it.
Wear the costume long enough and people start to believe you, and that is the problem
This is the source of fake it till you make it. It isn't all bad and actually makes sense some of the time, but only if what you're pursuing is really coming from your heart in the first place.
If this feeling were really about competence, then competence would cure it. Get good enough for long enough and the mind would quiet down, and the feeling would eventually go away. That's the promise anyway. Work hard, get results, and one morning you'll wake up and finally feel like the guy everyone already thinks you are. Watch what usually happens instead.
A man gets the promotion and often the imposter feeling gets louder. He gets the clients and the room and the platform he's been gunning for, and now there's a great deal more to lose, so the bracing gets worse rather than better. I have sat across from men running entire companies who still had that low static running underneath everything, and it had not moved an inch in twenty years of achievement, awards, and the kind of outside evidence that was supposed to settle it. Despite all their accomplishments, there was still an emptiness, a striving that ran deep in their veins, and a voice that quietly said, "It's not enough. You need to be the best. Then they'll see who you really are." Except no one can see who you really are because you're not showing anyone who you really are. You're still wearing the fox costume, hoping they will finally notice you're a wolf, but they simply can't see past what you're showing them.
Because every success you have in the costume becomes evidence that the costume is the thing holding you up. Just look at some of the biggest names in Hollywood and music and you'll see what I'm talking about. These people have made it to the very pinnacle of success, yet they are so chewed up from the inside out that they turn to drugs, or worse, suicide. They're aching to be seen for who they really are, but all they can do is continue to show the facade. It's an all too familiar story.
Taking the costume off doesn't get easier as you climb, either. It gets harder, because now the stakes of being wrong about who you are include every single thing you built while you were pretending to be something you're not.
That is how a man ends up in his mid-forties, accomplished by any measure somebody on the outside would use, and he's still braced for failure. Not because he failed at anything, but because he succeeded at the wrong thing over and over again, and the succeeding is exactly what kept him from ever having to find out who he actually was underneath it all. This can be one source of what we call a "midlife crisis" in men. I prefer to call it a midlife awakening, but that's a different story.
What happened in that circle
So there I am, seventeen pairs of eyes, voice half a step high, waiting for someone to notice and call me out. Then something turned, and it was not that I suddenly found my confidence.
It was the eye contact. I went around that circle and actually looked at each man one at a time, understanding somewhere in my body that we had all come this far together, that these men had rearranged their lives and driven a long way and put their phones in a box when they arrived, and that they were counting on me to show up. I was on the hook to show up even if it was messy, and even if I had no idea what to say.
That got me out of my own way. It wasn't about believing in myself more. It was about looking at who was counting on me. Then I said something I won't forget.
"If you came here looking for answers, you came to the wrong place. I don't have them. I'm simply here to help you find your own answers."
That line might read like it was coming from wisdom or humility, but it wasn't. It was my costume coming off in front of everyone there. It was me deciding to allow myself to be imperfect and state the one thing I actually knew to be true in that moment. Because I'm no guru, nor do I want to be. I'm just a man who's been through things and is here to help other people get through their things. It's really that simple.
My entire facade had been built out of a single unspoken claim, which was that I was the guy with the answers, because that is what a man standing at the front of a room is supposed to be. The moment I said out loud that I wasn't, there was nothing left to protect and the feeling of being a fraud had nothing underneath it to stand on. So it just collapsed.
What I noticed after that, which I did not expect at all, was that the room got closer rather than further away. It turns out seventeen men do not actually want a leader at the front of the room who has it all handled. They want somebody with the courage to go first and let them know we're in this together.
If you do much research at all, you'll find that some of the greatest and most respected leaders and teachers throughout history have had this same quality, the courage and willingness to step first and say, "We're going to figure this out. I have an idea of where to go, but I need your help to get there."
So what do you do with this?
I'm not going to hand you a practice list. A practice list is just one more framework to borrow, and if you're anything like me, you've got plenty of those already. But there are a few things I know to be true.
You have to be willing to be wrong. Over and over again. I've said this a hundred times and I'll keep saying it until somebody makes me stop, because the most intelligent people I know are the ones who question things and ask what else might be going on here, and a man who cannot be wrong is a man who has to keep wearing his costume permanently. A man who cannot be wrong is a small and weak man. Period.
So be willing to look bad, to say the wrong thing, and to take a risk where everyone else is just standing by the wayside. It takes courage to be yourself in a world where everyone is trying to be like everyone else.
You have to meet your shadows instead of just trying to get rid of them. I know my shadows, I accept my shadows, and every so often I still turn up a new one. But I meet them, and meeting them is a different act than fixing them, and it's a very different act than pretending they were never there in the first place. They have become my friends and allies because my shadows are my greatest teachers. They show me where my work still is and remind me that I'm still an imperfect human in an imperfect world.
It takes repetition rather than intensity. My men's group has been running for over four years now, and four years of the same men in the same room watching each other week after week is worth more than any breakthrough weekend I have ever been part of, including the ones I've led myself. You cannot perform a costume for four years in front of people who are actually paying attention. It gets too heavy. Eventually you set it down just to rest your arms, and in my experience, that is usually the moment the real thing finally shows up.
The part that took me the longest to understand is that you do not need anyone else to tell you what you are. I don't need other people to call me a leader or teacher or writer, for that matter, and I don't need to call myself any of those things. But underneath it all, I do need to know that this is who and what I am. Nobody hands that to you, and nobody can take it back either, which is the whole point. It's also why no amount of applause or acknowledgement ever settled it for me.
It isn't a thing you settle once, either. I choose it in the parking lot before I walk in. I choose it again when somebody in the room asks a question I can't answer, and again when the easy move would be to reach for the voice of a teacher I admired twenty years ago instead of my own voice. Some days I choose wrong and catch it an hour or two later. I'm not perfect. I'm a work in progress, and I always will be, just like everyone else on this planet. Honestly, that is one of the most comforting things ever if you let it be. We're all here trying to figure it out, pretending like we're the ones who figured it out, and hoping everyone else doesn't see that we're trying to figure it out, when in fact they can't because they're too worried about themselves. That's a slice of peace right there. I hope this all makes sense.
The question
I still get nervous before I open a circle or speak in front of groups. That never fully goes away for me, and somewhere along the line, I stopped waiting for it to.
What changed is what I do with it now. I don't try to talk myself into feeling like a fox anymore. I just check whether I'm about to tell these men the truth about what I am, and when the answer is yes, the nervousness turns out to be nothing more than nervousness. It's not a warning or evidence of anything.
So here's what I want to leave you with. All those years I spent trying to feel like I deserved the costume were years I could have spent finding out what was under it, and I don't get those back. I'd rather you didn't spend yours the same way.
Because the question was never whether you're good enough for the room you're standing in. You already know you can do the work, or you wouldn't be braced about the possibility of losing it, right?
The question is who you'd be in that room if you weren't managing everyone's impression of you, what you'd say, what you'd stop pretending not to need, and whether the people around you might actually come closer instead of further away, which is the part I got wrong for twenty years and the part I'd want you to test for yourself before you take my word for it.
Nobody is coming to take the costume off of you. It's yours, and you've earned it over your lifetime. Just know that each day you wake and put it on is a choice.
Take the costume off and find out what you actually are. I'd love to know what you find. See you on the other side.
Read more from Daryl Henderson
Daryl Henderson, Transformational Facilitator & Creative Visionary
Daryl Henderson is a master coach, facilitator, and artist with over two decades of experience blending creativity, men’s work, and spiritual practices. He has photographed top brands and artists worldwide, including Nike and Michael Kors, and documented indigenous and peace gatherings across the globe. Drawing on this experience, Daryl guides high performers, artists, and businesses to express their stories through soul-aligned photography, branding, and personal transformation. He is the co-founder of Odyssey of Man, the creator of True North Coaching, and the founder of One11, a health and wellness brand. His work is playful, transformative, and designed to unlock authentic expression.
