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It starts deep in the pit of my stomach.

It’s hard to describe. It’s like a cross between butterflies and sharp fluttering stomach pain.

Sometimes, it manifests itself as a pain on the left side of my neck. It feels like a burning, humming sound. The buzz you might hear at a power substation full of large transformers.

Other times, it manifests itself as acute insomnia. I am up all hours of the night thinking about all sorts of bad things.

I didn’t know what to call this experience until about a year ago when a friend gave me a name for it.

Impostor Syndrome.


Impostor syndrome is a brew of negative emotions, including anxiety, depression, and low self-esteem. These emotions often bubble over, spoiling the sense of accomplishment and ability within successful individuals.

Leary et al., in their 2000 study, defined the impostor phenomenon as a difficulty internalizing one’s own success, and a perpetual sense of self-doubt, of being a fraud or fear of being discovered. They found that the symptoms of Impostor syndrome are paradoxical, especially the belief impostors hold of others overestimating their intelligence or ability. This belief manifests in many different ways.

Do I belong here? Am I good enough for this role? I’m totally underqualified.


I felt completely out of my league. That feeling has stayed with me — buried deep in my psyche — over the last two decades. (Image: istockphoto)

The first time I experienced impostor syndrome was during my freshman year in college. I was sitting in a large lecture hall with hundreds of engineering students, experiencing college for the first time. It was a calculus class, and I was looking around observing the types of questions and interactions from some of the students. I remember feeling like I might be in the wrong place. I might not be good enough to be in the company of these people.

I was the valedictorian of my high school — George Westinghouse, in Brooklyn, New York — , proud to have been in the number one place and the only one to be going away to an Ivy League school. My parents were very proud of me.

When I arrived at Cornell, I realized that everyone was a valedictorian. Some of these kids had gone to some of the best, most elite schools in the country. They had taken advanced courses to prepare themselves for this experience. One time, in my student dorm, I saw this young man who I had seen around campus. He was an upperclassman.

He was seated at the public piano in the dorm’s common area, playing a full piano concerto.

This was what he did in his spare time.

It seemed to be about relaxing himself before starting on his assignments for the day.

Oof, I felt completely out of my league. That feeling has stayed with me — buried deep in my psyche — over the last two decades.

Anytime I’ve been at the helm of a new venture, where I’m ultimately responsible for its success, I experience that humming sound.

Buzzz, hummm.

It kicks in on cue, whenever we run into a roadblock, or when we’re about to kick off a major initiative. When it happens, I can hear my internal voice say, “do you really belong here?”

“Are you really cut out to be in this position?”

In my first enterprise, I didn’t have a clue about what I was doing. But, I sought out to get the expertise to help me be successful.

I’ve formed at least three companies now, all of them successful in their own right.

Yet, I always felt that these successes were really beneficiaries of a bit of luck. It had nothing to do with my experience, my expertise, my firepower.

So every time I’ve been given the opportunity to be involved in something, that feeling rears its head up again.

Buzzz.

That feeling in my stomach, that pain in my neck. And that experience with sleep, that’s not sleeping.

What I’m describing is something that just about every entrepreneurial leader in the world is familiar with today.

In fact, according to this report, over 70% of the world’s professionals have experienced some form of impostor syndrome.


I thought I was alone in living the effects of the syndrome until I participated in a CEO peer group.

At my first meeting, I was sitting with a group of very successful CEOs. I was surprised when they each expressed concern at some point about whether they were good enough in their role or the fact that they might be the wrong person for the job.

It threw me for a loop.

Here were these legendary CEOs asking themselves, “Am I good enough?”

My initial reaction was, “wow, I’m not the only one that feels this way. This is not unique to me, everyone experiences this.”

They were there to talk about how best to overcome and use the energy that was inherent in this feeling of inadequacy — to get to their goals, their ambitions.

What I learned from the peer group experience, was that being the CEO puts you in a unique position where you feel overly responsible for the company’s success.

I think it heightens the impostor syndrome. You feel like the success of the organization is on your shoulders. And, you doubt if you are the right person to make it happen.

All of these thoughts run through your head.

If you’re not good enough, if you’re not strong enough, then, the company will fail, and you will fail. Everyone will realize that you weren’t cut out to be in that position in the first place.

I’ve had these thoughts countless times. And over the last few years, I’ve focused a lot on developing a set of skills and tools to help me overcome it and lean into the syndrome, not run away from it.

Instead, I’ve learned to embrace that feeling. I now use it as fuel to power my success.


The way to overcome being frozen by impostor syndrome is by understanding the source of emotional and physical turmoil. But, tackling that muscle between the ears is a real challenge for many.

About a dozen years ago, I spent time with a coach that helped unlock the secret passage to the source of this anxiety. It changed everything for me.

The source is a volatile mixture of thought and emotion that teleports us to a different time and space, gripped by fear.

Faye Mandell, author of GPS to Self-Powerment and the founder of Being Present, beautifully explains the source of different states of being such as fear, frustration, sadness, and anger.

According to Faye, fear is a combination of anxiety and future thoughts. Anxiety is an evolutionary emotion — the fight or flight emotion — that has protected us for centuries. When we are anxious, it’s a warning sign; our body is telling us to focus.

When you don’t focus on that anxious feeling, you start thinking about the future and all the terrible things that might happen–resulting in what Faye calls a feeling-thought. That feeling-thought is fear.

So, I learned that when I am afraid, it’s because I am anxious about something that is going to happen in the future–like my company running of money. Sure, that is one way that things can play out, but I am in the present. And, that version of the future hasn’t happened yet.

“What can I do in the present to prevent that future I imagine from actually happening?” I think to myself.

In other words, when I am anxious, I need to redirect my energy toward that feeling. I will then automatically start building a solution and establishing the next set of execution steps to get me down the road toward my desired destination–a successful round of financing.

I’ve spent many years practicing this art of noticing what’s happening, why I’m feeling anxious. It led me to the epiphany that impostor syndrome is a gift for leaders, CEOs, and any professional to fuel their ambition.

So, I now use this and other tools that keep me positive and in the present.

Let me share those tools with you.


1 — Reflect

Take time away from the business and operations to reflect. This allows you to learn from some of the mistakes you’ve made. You can see where there have been failures then use those failures to drive changes in your behavior and drive towards successful outcomes.

I also write a “brag sheet.” At the end of every year, I write down all the accomplishments that I’ve made.

I actually have my team do the same. We write down everything that we’ve done successfully and our learnings. That’s part of the reflection process that we do individually and as a team. That brag sheet helps me realize that I’ve actually gotten a lot done.

It’s not all bad. There’s lots of good in there as well!

2 — Find (or create) a peer group

One of the best things I ever did as a founder CEO is to join that CEO Forum I mentioned earlier. It was the first time I realized that all the pain I was going through was shared by other entrepreneurs just like me. In fact, that’s when I learned that my problems were like gnats on an elephant’s arse by comparison. It also opened pathways forward that I couldn’t see on my own. Once a quarter, I would escape the business to cry on the shoulders of other men and women who were living the startup life.

So, if you are an entrepreneur suffering alone, then I encourage you to find a peer group to join. If you can’t find one, then ask another entrepreneur you know to meet for lunch once a month and just share stories and bounce ideas.

Do this exercise — have one person explain a situation they are encountering, and then you each respond with “if I were in your shoes, I would…”

Over time, you can expand this two-person group to more and boom, you have your very own peer group.

3 — Get a coach

Getting a coach, as I mentioned, with a particular skill set in self-awareness, really unlocked my ability to build a practice for myself, that ultimately got me going on the right path.

Find yourself a coach. Someone who’s been in your shoes and understands the challenges that come with being a CEO. Ideally, it’s someone you trust enough to share your inner thoughts and feelings. It helps to talk through those feelings with an impartial observer. But, don’t hold back, it ruins the process of healing and growth you get from catharsis.

4 — Seek feedback

Embrace and seek positive feedback and negative feedback from your peers and your employees. I do a CEO review every year. I ask my board for feedback, I ask my subordinates for feedback, I even ask my peers for feedback just based on what they’ve seen me do. I then open up the survey to the broader employee base. Also, if they haven’t had direct exposure with my execution, they can offer insight into things that I can do better and improve. And more importantly, they offer me a perspective of myself that I may not see, including items that I do well and things that I don’t do well.

5 — Avoid envy

One of the great things that I’ve heard Charlie Munger say is, “you know, you should really avoid envy. That’s just a bad thing.”

Envy is a deadly disease that many people experience. Spend less time envying other people, other CEOs. Sometimes I’m looking at all of these successful CEOs and thinking, “I’m just not cut out for this thing, I could never be at that level.” Or I say to myself, “why aren’t I that good? Why aren’t we executing as well?”

That’s just a futile practice and a huge waste of time.

6 — Be vulnerable

I think the other piece is being vulnerable. Vulnerability is so essential as a leader. I can’t stress enough how important it is for you to be comfortable putting yourself out there and letting your team know that you really don’t know all the answers.

“I don’t know how we’re going to get through this. But I want us to stay together.”

“I’m really feeling like at the end of my rope here in terms of how best to move forward.”

That vulnerability is so powerful because it brings the team together, it gets people expressing their own anxieties, and then helping each other to focus on going forward and trying to solve the problem as a team. It’s so helpful for the team to work together. And the only way that they can do that is to build trust. That trust starts with you.

A CEO that is comfortable expressing the fact that he’s going through impostor syndrome, that he doesn’t believe he is cut out to do what they’re doing, are challenged in getting to the right answer, or just feeling anxious about where the company is going and what they need to do next, is so powerful a pathway to trust.

Many times that is the answer. Just by expressing it, you open up the door to being incredibly successful.


Why I Embrace the Phenomenon

My close friend and mentor once told me, “the moment you set off to reach a goal, it is just a series of problem-solving exercises from there on.” That awareness he explained helps to lessen the surprise — and resulting anxiety — that comes with roadblocks, and challenges.

It’s just part of the journey.

I believe entrepreneurship is a struggle. It’s a struggle between making your dreams a reality and fighting your inner demons.

As Ben Horowitz puts it, “Are you good enough to do this? As your dreams turn into nightmares, you find yourself in the struggle.”

That struggle he speaks of presents itself differently in every person. For me, it’s the “buzzz” and “hummm.”

When it comes instead of trying to escape it, I embrace it as a reminder that I am still in my journey to Ithaca. (The destination of my goals.)

My advice to you: When your sign comes, embrace it and stay with the struggle.

A one-percent advance each day is enough to know you are still making progress