The One Simple Question Successful Women Leaders Ask Themselves

A couple of months ago, I was in a full day session with a client developing a promotional strategy for an exciting new initiative she was working on.

We’d been at it for a couple of hours and things were going exceptionally well. Totally in flow and elated with the ideas we were jamming on, we knew were on to something big and really quite special. However, we also knew that what we were planning was going to require that she stretch into her courage and step into her leadership shoes in a significant way.  

All of a sudden, a look of complete terror washed over her face and she burst into tears - unstoppable, face-destroying, mascara-laden, huge crocodile tears. 

“I can’t DO this,” sobbed one of the smartest, savviest, and most successful women I happen to know. “I just can’t put myself out there like THAT.”  

Frantically pacing the room, vigorously shaking her head and flailing her arms in all directions, she actually stomped her foot at one point and said, “No way. Totally NOT F-ING HAPPENING. It’s just too much.”

After about 10 minutes, the storm subsided and she began to calm down. I firmly put my hands on both of her shoulders, looked deeply into her eyes and lovingly, but pointedly, posed this question: “Really, what is the worst that could happen if you do this?”

“Ultimately,” I said, “even if the best possible scenario doesn’t materialize, the worst possible outcome is that you end up exactly where you are now, only with infinitely more insight and wisdom than you started out with. Either way you look at it, you only stand to gain.”


As I say so often and like I said to my client that day, stepping into greater leadership is not easy and it can feel really, really scary. And precisely because it is hard and scary, it’s also very rare.

Presenting new ideas, launching a business, going after a promotion, speaking to a crowd of strangers, asking for a raise, sharing our art, challenging the status quo, resisting the urge to settle – these are all gorgeous examples of leadership in action.

However, they’re also often stomach-turning, hair-raising, and heart-pounding experiences that can make you feel like you’re walking down the street completely naked in the middle of winter. In a nutshell: very uncomfortable.

When we make the decision to play bigger in our lives, careers, and businesses, the universe summons us to shift into our faith and fortitude, alongside our visibility and vulnerability. At the same time, we’re forced to accept that the likelihood of failure, criticism, rejection, and even ridicule become much, much greater.

For most of us, that can all seem pretty damn terrifying and not particularly desirable.

Some of us will determine that the risk is worth the reward, and some of us won’t. Interestingly, both kinds of people are equally important in the leadership equation.

As Seth Godin so beautifully sums up in Tribes, “Leadership is scarce because few people are willing to go through the discomfort required to lead. This scarcity makes leadership valuable. If everyone tries to lead all the time, not much happens. It’s discomfort that creates the leverage that makes leadership worthwhile.”

I’d be lying if I said that there’s a surefire way to make those feelings of fear, doubt or even full-on nausea go away. There isn’t, and you should likely run far away from anyone who attempts to tell you differently. Because the fact is, you don’t really want them to go away.

As Godin points out, “If you’re not uncomfortable in your work as a leader, it’s almost certain that you’re not reaching your potential as a leader.”


Here’s the harrowing, but heartfelt truth: your deepest fear is often your soul’s highest calling for your greatest opportunity to lead. Your resistance and discomfort are often the best indicators that you’re doing exactly what you need to be doing.

Leadership is the art of learning to breathe through that fear and forging ahead anyway. It’s about the willingness to live our lives out loud and bring our biggest, most daring aspirations and ideas into the light. Leadership is about leaning into the knowing that opportunity rewards the bold and luck always bends for the brave. 

In the wise words of Neil Gaiman, “The moment that you feel, just possibly, you are walking down the street naked, exposing too much of your heart and your mind, and what exists on the inside, showing too much of yourself...That is the moment, you might be starting to get it right.”

 Always ask yourself, what is the worst that could happen?

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