The Backwards Hat Effect

It was the last day of Waypoint Retreat 2025, and everyone was going around the room, sharing their reflections from our past two days together.

Some Waypointers had profound reflections ("I'm not afraid anymore!!") and others were less so ("I really need to do this more") - all were memorable and valuable in their own respects, but one in particular stood out for me.

"I want to get to a place where I can go to work wearing a backwards hat like you, Greg."

To my surprise, the group laughed and clapped in agreement.

In the midst of creating Vienna Waits, building our UNBLOCK Yourself™ program, Vienna Five newsletter, an emerging consulting and advisory practice, and of course, Waypoint Retreat itself, I'd lost sight of some of the things I'd been leaving behind, and some things I'd been rediscovering about myself.

Over the course of hosting Waypoint Retreat, I spent most of my time wearing a backwards hat. It felt like the right thing to do, so I didn't really think twice about it. I'd forgotten I was "at work," and as it turned out, it had an impact on the people around me.

A few weeks later, I was in downtown Toronto, preparing to host our first ever live off-site for the Senior Leadership Team at Riipen - a group of 16 Directors, VPs, and C-Level leaders of this fast-growing EdTech company. Over the years of my career, I've helped lead and facilitate dozens of leadership meetings, but this was the first time doing it as Vienna Waits and for a company that I wasn't intimately a part of.

As I got dressed on the first of two mornings of our off-site, I thought of the comment from the retreat and looked at myself in the mirror.

Dark jeans, button-up shirt, dress shoes... and no hat. And I couldn't bring myself to do it. It sounds ridiculous, but I was too scared.

The first day went well. I met a room full of people I'd not met or worked with before, and they seemed to buy into me as an advisor and guide for the work we needed to do as a team.

As I prepared for Day 2, I looked at my planned outfit for the day - dark jeans, button-up shirt, dress shoes... and thought back to that comment from Waypoint.

For some reason that morning, I felt different, and I went for it.

I have to say, stepping out in front of a room full of leaders in a backwards hat doesn't feel like a brave act... even writing that makes it feel less than notable. But I will say that I felt very nervous about it for about 15 seconds. And then... I got on with it.

Day 2 started well - we were doing a large group session for the morning, and the plan was to go to smaller breakout groups for the afternoon to build action plans that would capture the work that needed to get done after the off-site. At our first break, two people commented on my hat - they told me they thought it was cool. Despite the compliment, my anxiety spiked. The voices in my head started making me question whether it was a distraction, or whether people were taking me less seriously because of it, and I started to think it would be a good idea to ditch the hat for the afternoon.

I carried on with things, closing out the morning and giving instructions for what would need to get done in the afternoon groups. I was facilitating one of the small groups, and as I opened up the session, I looked around and saw four people in my group... hats on... backwards... ready to get to work. One of them asked me where my hat was, and I immediately ducked out of the room to get mine back on.

Hats on (backwards), we got to work and had a GREAT session together. At the end of the day, one of the leaders in the business approached me and asked if I'd be open to working with them as a coach to help them establish themselves in a new leadership role they'd taken on in the business.

Turns out the hat didn't take away my credibility.

Somehow... it added to it.

Since then, I wear a hat to work most days, and I don't think much about it. In fact, a few weeks ago, I was asked to help interview a new executive leader for one of our clients and showed up in a backwards hat. A few minutes in, I looked across the screen, noticed them in a suit, and laughed, apologizing for showing up in a backwards hat for our call.

Their response was familiar - they laughed too and asked if they could take off their suit jacket so that we could have a more "real" conversation. She did, and it was one of the best interviews I've ever done.

As is the case with so many big realizations in life, it took almost a year for that comment from Waypoint to really sink in for me.

It's not about the hat, specifically... but the hat is a symbol of something bigger and more important.

Authenticity.

It turns out that being authentic is contagious. The term I came across for it is "self-disclosure reciprocity." Research shows that when someone shows up and is real with you, it creates a desire to do the same. This is true one-to-one and in groups.

For my whole professional life, the version of myself I tried to project was someone who had their shit together. The model I had for that, from my early days at IBM, was leaders in suits. Polished, poised, and "perfect."

The problem is that isn't me.

I want to go to work wearing a backwards hat. I want to swear sometimes. And I want to be able to say, "I don't know," when I don't know.

Turns out, if that's the truest version of me, it's also the version the world wants from me.

So my question for you is this: what does being authentic look like for you?

Whether it's a backwards hat or something else... bringing that version of you out will change how people see you. I'm willing to bet it probably won't be the way you're afraid it will.