The Art of Being Uncomfortable, On Purpose

Picture This: There was no backstage. The room was set classroom style, and I sat in the reserved VIP row with the executive team who had hired me.

Backstage, in some ways, is easier. You have a wing to stand in. A moment alone to become the version of yourself the room needs. I often imagine Amelia Shepherd in Grey’s Anatomy when she does the “Superwoman” pose before surgery. Sometimes you just pump yourself up.

Early this month, I had none of that. I sat in full view, in that front row, in plain sight of the rows of chairs behind me, while the anticipation built in real time with nowhere to put it.

For thirty years, I had walked into rooms like this with a brand standing behind every word I said. If a story did not land the way I hoped, the company absorbed the miss. This time there was no company sitting in that row with me. There was only me, present, anticipating, with the people who had taken a real risk on a single voice to carry their morning close enough to see it on my face.

I had personal stories in the keynote. Real, unresolved in places, not tied up with a bow. I did not know how the room would receive it until I was standing in front of everyone finding out in real time. And I would find that out with no wing to retreat to afterward. Just a seat back in that same row.

The Wider Lens

There is a version of courage that gets celebrated in leadership circles. Go for it. Take the swing. Say the true thing. What gets talked about far less is what it costs to do that with no private moment to gather yourself first.

As a solo entrepreneur, I was not only weighing what would move an audience. I was weighing what would make the executive team, seated in plain view, feel their bet had paid off, and I was doing that weighing in full sight of them, not in some private wing where I could arrange my face. Comfortable with being uncomfortable does not mean chasing discomfort for its own sake. It means learning to stay present inside it, in front of the very people whose judgment you are anticipating and still choosing to say the true thing anyway.

Three Things I Learned

The fear was not about public speaking. I have given hundreds of talks. The fear in that row was about having nowhere to privately prepare. Every flicker of nerve was visible to the people I most wanted to reassure.

Presence is a different skill than performance. I could not disappear into a role backstage. I had to be fully myself, in that row, anticipating, while still appearing composed enough to make them believe in the choice they had made. Staying present through that, rather than performing a calm I did not feel, was its own kind of going for it.

Weaving personal stories into the keynote, especially Ash’s journey, was the discomfort itself, and also the point. I did not tell them because they were polished. I told them because they were real, and because an audience of travel professionals needed real examples of what it costs, and what it gives back, to author your own story instead of running an inherited one.

The Wondering

What would change if you had no wing to retreat to before the moment that mattered, and had to feel every bit of the anticipation in full view of the people judging the outcome?

Whose eyes were you most aware of the last time you took a real risk in a room?

Give It Five Minutes

Think of a moment you handled recently where you had no space to gather yourself before and it was in front of people whose opinion mattered. Spend five minutes writing down what you actually felt in that moment, separate from how you think you appeared. Notice the gap between the two.

My Intention

I will let myself be visibly present in the moments before it matters, instead of performing a calm I do not feel.

With Curiosity,