10 Successful Leaders Share Their Struggles with Imposter Syndrome and How to Overcome It

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10 Successful Leaders Share Their Struggles with Imposter Syndrome and How to Overcome It

This feeling, often prevalent in high-achieving people, is commonly known as "imposter syndrome."

Imposter syndrome is a thought pattern where a person has a persistent fear of being exposed as a “fraud,” and which makes that person doubt himself and/or minimize their accomplishments. 

Recently Authority Magazine interviewed dozens of high-achieving C-suite executives and leaders who all shared their own experiences overcoming imposter syndrome, as well as the advice they recommend for getting past it.

In the summer of 2018 while I was working on my book, a journalist from The Wall Street Journal asked to interview me for her "Work and Family" column. When I looked at who else she had featured, I saw people with big titles and important roles, and I wondered, “Why would she want to hear my story?”

I saw myself as less accomplished and less relevant. I had to remind myself that in the past, I’ve held senior roles in global organizations, and I realize my experiences at these places counted. Not only did I enjoy our conversation, we spoke again many months later on a different topic. In the end I was quoted twice and met a wonderful woman who I now consider an ally.

Early in my career before I ever heard of impostor syndrome, I lived with it all the time. I would walk into a meeting at work and wonder “Do they like me? Am I smart enough to be here?” It took me several years before I walked into a room and asked myself “Do I like them? Are these people I respect and admire?”

I don’t know that it’s possible to be entirely rid of impostor syndrome but I do manage it better today. What has helped me is learning to recognize it so I can deal with my feelings rationally and talk myself down.

Last year my colleague Elizabeth Bastoni shared some advice that really helped. She said “Don’t say no to yourself, let other people do that for you.” When I start talking myself out of an opportunity or favor because I don’t think I’m worth it, her words are a good reminder to put myself out there and let others decide. More often than not, their answer is yes.

As a black male therapist, I haven’t always had an example to follow or model myself after. In my graduate program I was the only black male in my program the entire time I was there. I think this experience led to my questioning whether or not I knew what I was doing. I don’t have an example to follow to effectively evaluate my trajectory and therefore, enter into effective questioning if I will be successful.

I continually overcome any feelings of being an impostor. I use the same techniques and skills I teach my clients. I tell myself, when exploring a new opportunity, I successsfully explore other new opportunities in the past and will continue to so with new ventures. Moreover, I try to tell myself I am doing a good job, and look at the evidence that supports this. 

5 steps someone experiencing imposter syndrome can take to move forward, despite feeling like an “imposter."

Although I’ve been quite familiar with the feeling from early on in my life, imposter syndrome really started to rear its ugly head up when I was about five-six years into my career of building Sseko Designs. We had to build a traditional wholesale/retail company and were considering pivoting to a direct sales model. I believe the opportunity to od business and make an impact was immense, but so was the risk. At this point, I had a multi-million dollar company with employees and partners across multiple countries. I started feeling like if I tried to lead us through this pivot and failed, that would be the moment when I got “found out” for being an imposter. Everyone would say, “See. She is not a real leader or business person. It was all just ‘beginner’s luck.’” As a result, I had an incredible amount of insecurity and anxiety.

I may not have gotten rid of it completely, but enough that I was able to move forward — and I am glad that I did! In our first full year of selling through individual women in their communities, we did more in revenue and impact than we had ever done through our wholesale channel! In order to overcome it, I revisited the earliest days of my career and started studying the mentalities and mindsets I had they helped me resist imposter syndrome without even knowing it. My study of those mentalities and mindsets was such an “a-ha” moment to me that I ended up writing an entire book about it so that others can access their “Inner Beginner” as a way of overcoming imposter syndrome so that you can build a life of purpose, passion and impact.

5 Steps someone experiencing imposter syndrome can take to move forward, despite feeling like an “imposter."

Absolutely. When I first started my own company, I was terrified and young. I had just gotten fired and broke. Everyone doubted me. And even though I chose to press forward, block their voices out and believe in myself. Predictably, I was still terrified. But I felt the fear and did it anyway. Ultimately, your confidence must be greater than your doubt. As an entrepreneur and executive, a huge part of success is that you keep going despite doubt and uncertainty.

I believe I did. Rather than focus on feelings of self-doubt or worry, I focused on my vision and my passion. I zeroed in on the things I wanted to achieve and the things that made me feel grateful to be alive. These were the things that were the most authentic and true to me.

I also learned to master my emotions. Sometimes, we act as though fear and self-doubt are real and true facts. Really, they’re just emotions that are only as powerful as we make them. I stopped allowing those feelings to overwhelm me or distort my reality.

I’ve also made an effort to surround myself with successful people who support me and challenge me.

My first experience with imposter syndrome came after I was promoted to National Sales Director. I started to believe that the only reason I got the job was that I was the only candidate willing to move to New Jersey. I also thought I had to lead like all the National Sales Directors in my industry, but that wasn’t my style. As a result, I lost my identity for a few months. It was an extremely stressful period and I wondered if I was the right person for the job. These feelings stayed with me until I shifted my thinking and regained my confidence.

Yes, I was able to shake off my imposter syndrome by shifting the conversation I was having with myself by developing a list fo accomplishments and a few mantras to remind myself why I was promoted. I also started looking for small wins, which I knew would lead to bigger ones down the road, which they did.

Absolutely! Coming from the agency world meant I was well-versed in business. My interest in lifestyle was strong, but as I worked on the business model, attended events, and met other professionals, there were definitely times where I felt like I did not know what I was doing. While I knew intrinsically that I was competent, I found difficulty in navigating this new space with my new company. That’s what’s so tricky about imposter syndrome: you know you’re good, but it doesn’t always show.

Yes, through consistency, I was able to work my way out of it. Every time I accomplished something, I would remind myself that it was because of my talents and perseverance, and how I deserved to be there.

My education was in fashion design, and although there are many parallels from apparel design to product design, I’ve always regretted having not taken product design courses. When I started building out the design team at Garrett Leight, I was nervous that candidates with way more product design skills would not respect me as a boss, or that I wouldn’t know what were the magic ingredients were needed to build a strong team. Designing frames was something I was grasping quickly, but managing a team was something I had never done.

On the flip side, when we were first starting out as a company, there were only a few of us, and I had horrible work life balance. I would stay at the office late, and lost touch with a few friends and had trouble giving my friend base the time they deserved. I also had no time to network or interact with any type of peer group, which made me feel like an imposter when I started interacting in fashion circles. It was like an imposter pendulum; on one side I felt not technical enough, and on the other side not connected enough. I was in my late-20s introducing myself as a design director of an eyewear company with no previous eyewear experience, and bracing myself for questions about how I got the job. I knew I got this opportunity from a combination of hard work and luck, but would constantly question if I was truly the most qualified person for the job.

As the company grew, I wasn’t always able to have a clear vision of how I wanted to personally grow. I realized I needed to make some changes and give more balance to my life. I think the most confusing part for me was how I evolved through my job. When I was hired, the company needed me to do a lot of roles (i.e. design, development, production and sales), but as we grew, I was expected to be an expert in a specific field. It was difficult for me to adapt, and there was no magic ball telling me exactly how I had to change. There was no how-to guide on building and managing a team, and giving direction.

However, I got some good advice from one of my mentors to really understand what my best strengths were, and had a real constructive conversation on the things I wasn’t good at. The irony is the I was advice I was told was the following: No one is ever blessed with knowing exactly how to do everything. It’s the journey of figuring it out that helps you learn how to do things and continuing to perfect your process.

5 Steps one experiencing imposter syndrome can take to move forward, despite feeling like an “imposter."

When I first began my career, I was involved in large-scale investment companies. Having graduated from Columbia as a veteran, I climbed the ranks quickly as the company positioned me strategically with important clients that value veterans. As I looked around at the high-level executives around me, I felt like I didn’t deserve to be at the top with them. As a result, I felt like I couldn’t ask the questions necessary to understand a subject because I worried that people will see me as not smart. Knowing that tendency, I created a rule for me that I would only create teams of experts, where I didn’t need to be the “smartest guy in the room.” That allowed me to always be surrounded by the best professionals, and ask all the questions I needed to truly master and solve any situation or problem that arises.

Yes, but not without practice. I spent years accruing experience doing what I love and surrounding myself with other successful entrepreneurs. As success came in each endeavor, I realized that I do have the ability to lead and create the life I want.

After building hedge fund products at an investment firm, one of our partners who I worked with closely on a successful project wanted to hire me into their firm. This firm was one of the best — highly ethical and extremely well-respected. Even better, the team I was to join was run by one of the smartest, kindest women I met during my short career in finance. Despite these positives, I was certain I would fail if I took the offer. I was fundamentally afraid that without the pedigree (since every single person there had attended The Wharton School of Business), the degree in Economics (my degree was in literature and history), and a coveted CFA II certificate, I would last for a few months and then be fired. Looking back, I would have flourished. It was a perfect role for me: It combined my love of explicating structure and process, integral to how a portfolio is built, and communicating outcomes, integral to the explanation of how a portfolio performed. Sadly in the end, I didn't take the role. 

I don’t think people with imposter syndrome permanently eliminate the feeling, since it’s about alignment between your internal self and how you are perceived by the world. But I’ve found some tools to change the internal dialogue about that process. How we work — listening, teaching, and making — can be the best tool for that.

For example, I’ve accepted that I don’t pop-up out of bed at 5:30 AM, but that doesn’t mean I can’t make a habit of it and make it last for years. I’ve learned that general productivity — clocking good hours at my job, meeting professional goals, expanding my network — isn’t what I really want. The grueling schedule required a level of anxiety that kept me from the work I really wanted to do. So now, I wake up around 8:00 AM, and I read or write for an hour with a cup of coffee. This way, I arrive at work with clarity and intention. From this routine, I now have multiple essays in progress, a few new roles I’m going after and more warmth and generosity to offer others.

5 Steps someone experiencing imposter syndrome can take to move forward, despite feeling like an “imposter”:

I really started to feel like an imposter as my job grew at Facebook. Facebook was a place for crazy-smart, high-achieving, really young people. To go from more traditional corporate jobs to a role at job fast-growing and boundary-breaking tech company turned the idea hierarchy on its head for me. Suddenly, I wasn’t sure if I could measure up. Though it was humbling to feel like I wasn’t qualified enough to even be in the room with some of these people.

In my role, I was meeting with the heads of marketing for big global companies, and even though I had less experience than they did, they would listen so attentively my counsel about Instagram because the platform was so new, and they trusted you to guide them through it. Despite this authority, I did not know what I had done to earn their trust. And I often felt like I was just there. 

For me, it never goes away, and it never feels like I’m achieving enough. I minimize this by continuing to prove my value and focusing on the work itself. I also try to redefine what a C-level executive does and how they behave, to make it more authentic and approachable than people can sometimes think of senior leadership being. For example, I really like relating to people on a human level — it’s fun to understand what motivates people, what their home life is like, what music they’re into, and just be fun and silly sometimes. It's through these moments is when we build connections with each other.

5 Steps one experiencing imposter syndrome can take to move forward, despite feeling like an “imposter”:
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