Overcoming Imposter Syndrome When it Counts the Most

Thank you for subscribing to Mann on a Mission newsletter, which I write for servant leaders just like you, every couple of weeks. My mission is to address the Churn of Disconnection that's tearing us apart, propose best practices for bridging that Churn, and ways to get big sh*t done when nobody else is coming.

Not long ago, I was scheduled to give a keynote talk and a short workshop on executive communications to a group of very senior financial experts. I was backstage preparing when a familiar wave of nausea and apprehension swept over me. Rather than let it get the best of me, like I used to when I first started out as a speaker/storyteller, I closed my eyes. I did a big exhale, followed by two more slow exhales. I repeated to myself that I have all the time in the world, and then I asked myself three critical questions. Who are these people? Why am I here? What do they need from me? I slowly opened my eyes, did a few jumping jacks and some air squats, walked out onto the stage, and owned the room.

As a leader, imposter syndrome has always been a major challenge for me. I can't tell you how many times I've asked myself, who the hell am I to do this? The older I get, I ask myself that question more, not less. The difference is that now I have tools that allow me to answer that question in a positive, effective way, and then execute in a manner that leads to strategic outcomes. My answer to that question, who the hell am I to do this, is always the same: who the hell are you not to?

It turns out that imposter syndrome is a very, very common form of what bestselling author, Stephen Pressfield, refers to as “Resistance”. Steve defines Resistance as that negative energy that courses within us. It manifests as self-sabotage to keep us from reaching our higher aspirations and goals of self-actualization. The more our goals mean to us and the world, the more Resistance will put itself between us and that path. For me, that typically manifests as imposter syndrome.

Who the hell am I to do this? There was a time in my life when that question could have potentially taken me down.

It was coming out of the military and transitioning into a world that I did not know or understand. By using storytelling and the deliberate, human connection skills of Rooftop Leadership, I started to recognize that imposter syndrome was causing me to not be fully available to the people I served. That's not unique to me. That's not unique to Green Berets.

There are leaders, just like you, all over the world who deal with imposter syndrome every day. It's just part of our human operating system. Perhaps it shows up in different ways, but it shows up regardless. It causes you to question your worth in the moment of truth. It causes you to ask critical questions of yourself that affect your status and willingness to serve others when it matters the most.

That can't happen in this time of Churn when we are distracted, disengaged, disconnected, and distrustful of each other more than ever. We need leaders like you who can step through those moments of imposter syndrome and deliver the goods to the people who need it the most. With that in mind, here are three things that I've learned along the way to deal with imposter syndrome.

1. Feeling reluctant can be a good thing. Just like in the storytelling framework of the hero's journey, the hero (you), the protagonist, typically refuses the call to action, and, even when accepting the call, accepts it reluctantly. "Surely there's somebody better than me to do this," we say to ourselves shaking our head and feeling knots in our stomach. "Surely there's someone more qualified than me to do this."

That might be the case, but they're not there and they're not stepping up. The reluctance that you demonstrate in those moments is a form of humility that is quite attractive to the people who need leadership. A leader who steps into the space and assumes personal responsibility for the outcomes of something bigger than themselves with a degree of reluctance, has a natural draw to the humans around her. That reluctance can be your friend, as long as you step into the arena in spite of it. It might not feel like it, but trust it.

2. The tribe doesn't give a shit. One of my biggest problems when I left the military and started to write, speak, and act, was that I kept asking myself, "what will my brothers in special forces think? Green Berets don't write plays. Green Berets don't cry on stage. Green Berets don't perform on stage. What will they think of me? I'll be the laughingstock of my tribe."

You ever feel anything like that when you step out on a limb to do something bigger?

Steven Pressfield says it best in Turning Pro: "The tribe doesn't give a shit." That's mainly because they're so caught up in their own issues that they don't have time to consider what you're doing or not doing. Yes, occasionally someone will make some snide comment about what you're doing, likely from behind the anonymous shields of some social media platform. But just know that kind of thing mostly comes out of fear as they look in the mirror at their own shit. They might even be wishing that they could fully express themselves like you. The reality is that this tribe we worry so much about is concerned with its own life, and simply does not have time to regulate yours.

3. People are starving for leaders who lead when they're afraid. The whole premise behind Rooftop Leadership is the ability to build strong social capital and inspire others in moments where they are angry or afraid, yet they take action anyway. And when this happens the reward is that people likely will follow you up to that proverbial Rooftop, not because they have to, but because they choose to.

Why do they make this choice? Why do people follow you into tough situations or buy from you when they're skeptical during these times of churn? It's because of the age-old concept of reciprocity. You do good for me, in terms of meeting my goals, and I feel a reciprocal nature to do good for you. It's a powerful, biological reality that defines us as a species.

Rooftop Leaders know this promise awaits them during the tough moments.

In those moments of truth, when we are feeling like we're not enough, when we're feeling like someone else should step into the arena, that's the very moment when we should step forward when everyone else steps back. It's where our knowledge of our own human operating system gives us a powerful return on our leadership: The people around you will be grateful that someone had the stones to step into the moment. They will buy from you, advocate for you, and most of all...follow you.

In this time of churn, all we see are transactional leaders who are looking out for their own status and well-being. When a leader steps into the moment and demonstrates committed action, even when they don't know the answers, hell, especially when they don't know the answers...we are grateful, and we demonstrate reciprocity over the long term.

The fact is that you'll probably never stop asking yourself, "Who the hell am I to do this?" All I'm asking you now is to answer it with this question. Who the hell are you not to? We need you leading us more than ever.

I'll see you on the rooftop.

P.S. Do me a favor. If this newsletter served you and you think it might help someone else, would you share it with them right now? This is a movement to get leaders like you and those around you onto their Rooftops leading us into better days.