“I can do that!” “I hate waiting in queues.” “I need a change.” These were the 3 main thoughts I had sitting in line waiting for my son to get his haircut at the local barbershop.
The thought seemed crazy for 2 reasons. Firstly I was 42 at the time and secondly I had spent the past 15 years dedicated to being a coach and counselor.
Something about the idea just resonated within me. I didn’t have the full picture, but I knew that I knew I had to do it.
So a year ago I started having conversations with my wife about next steps. I knew I had to be on the other side of the chair. Not just to cut hair, but to combine my years of experience as a skilled helper with grooming.
But here’s what was really bothering me.
I’d spent 15 years sitting across from men, women and teens who were struggling. Good people. Capable people. Folks who seemed like they were drowning in the gap between who they were and who they knew they could be. I’m going to focus on mainly speaking to men in this article, but the principles apply to women as well. And perhaps this can help you or someone in your life that needs to hear this.
And almost every single one of them had waited too long to ask for help.
Not because they didn’t need it. Because nothing in their world made it easy. A coaching session requires a man to already know something is wrong, admit it to himself, find someone, book an appointment, and walk through a door that feels clinical and unfamiliar. That’s a lot of steps for someone who’s been telling himself he’s fine.
So most of them managed. They coped. They went quieter. Did life as usual, went back to work, and carried on.
I kept thinking about that. About how many men never make it to a coaching room, not because they don’t need it, but because the entry point is wrong.
Starting over at 42 is a strange thing.
I knew the theory. I teach people to step into discomfort, to start before they feel ready, to stop waiting for the perfect moment that never comes. I’ve said those words hundreds of times across a desk.
Then I picked up a pair of clippers for the first time and discovered exactly how it feels to be genuinely brand new at something, and although I didn’t completely suck, I definitely felt out of my depth!
Humbling doesn’t cover it.
But something important happened in that discomfort. I started to understand, at a gut level, what the men I coach actually feel when they consider making a change. It’s not laziness. It’s not weakness. It’s the very specific fear of being seen trying, and failing, at something that matters to you.
I wasn’t just learning a trade. I was living the lesson.
And the more I learned, the clearer the picture became. The chair does something that the coaching room struggles to do. It lowers the guard before a word is even spoken. The ritual of it, the rhythm, the fact that nobody is sitting face to face demanding anything, it creates a space where honesty becomes possible almost by accident.
I knew what to do with that space. Fifteen years of training told me exactly what to do with it.
Roald & Co isn’t a barbershop that happens to offer coaching on the side.
It’s a space intentionally built for the man who would never book a coaching session, but might just need a cut.
The grooming is obviously a big part of it. I’m trusting that the conversations will be too. And if something comes up in the chair that needs more than small talk, I’m not just a barber who noticed. I’m a qualified coach and counsellor who knows how to go there with you.
I’m still new to the Barbering trade. The craft is developing. I won’t pretend otherwise. But the intention behind it has been fifteen years in the making.
Here’s what I want to leave you with.
Not a sales pitch. Just three honest questions worth sitting with:
What have you been telling yourself you’ll start when the timing is better, knowing the timing is never going to be better?
Where are you managing and coping instead of actually dealing with something that deserves your attention?
And what would it look like to begin, imperfectly, a little publicly, without the full picture, the way most worthwhile things actually start?
I didn’t wait until I was ready. I’m not sure ready ever shows up on its own.
I just knew I had to be on the other side of that chair.
In The Chair is a blog about real life, honest conversation, and what happens when craft meets purpose. New posts drop regularly at roaldandco.co.za