Annalee Hagood-Earl on Battling Imposter Syndrome

When we search for success or it finds us, it’s inevitable we experience imposter syndrome. Imposter syndrome is among the main reasons many talented individuals lack the confidence to start their own businesses. The internal doubts of “Am I good enough?” and “Do I know enough?” can be insurmountable. Imposter syndrome is very present in entrepreneurs. A survey performed to gauge the extent of this shows that 84% of Founders report feeling like an imposter [1]. Imposter syndrome usually takes two shapes: over preparing or procrastination. Either way, it leads to many never finding the courage to pursue their dreams. Or when in the middle of their pursuit, question their ability and value. But you are not alone. According to NerdWallet’s 2022 research, nearly 78% of business leaders surveyed reported feeling imposter syndrome within their work [2]. 

Annalee is the Founder and CEO of Bash Creative, an event strategy and production agency based in San Francisco, California. After ten successful years in business, she talks about her experience with imposter syndrome. 

Growing up with an entrepreneur father who retired at the age of 47 (when she was 11!), Annalee had always known she wanted to follow in his footsteps and beat him to that retirement age. When her full-time job in luxury hotels started taking up to 15 hours of her day, she decided to work as a contractor. She had no idea this would lead to founding a successful company. You can read Annalee’s inspiring story here

For Annalee, imposter syndrome didn’t manifest until she had struck out on her own as a contractor and was on her way to a site visit to land one of her first  clients. During full-time employment, she felt qualified, even overqualified at points. She was a high performer, naturally with high expectations of herself and others in the company. 

“When I left, I had the attitude that I was untouchable, I was amazing at what I was doing, and I was even outperforming some of my superiors,” she recalls, “Then, I went on my first site visit to win my first bid with a very reputable tech company in San Francisco. On my way there, I started having doubts. Who am I to say I know how to do everything they’d want? But when I arrived at the venue and shook hands with my prospective client, my instincts took over. I exceeded my expectations on how I would show up. It felt really natural. Plus, I got the job!

“That wasn’t the only moment I felt like an imposter. I’m still very much challenged with that. I still have to remind myself I’m worthy of how far I’ve come. I still struggle with representing myself and my accomplishments authentically, often downplaying my ability or contribution. 

“When I started, my goal was to make a hundred thousand dollars in a year. It seemed an extreme number at the time. Within one year, I exceeded it. I was thrilled! Now, 10 years later, I have a business partner and team selling and executing events. We have an expenditure of about a hundred thousand dollars a month, so my company needs to earn in the millions. It blows my mind when I think about where I started and where I’m now.” 

Imposter syndrome adapts to the situation. We may feel like an imposter until we master something. But when the next unfamiliar task appears, it kicks in again. 

“As my company grows, we constantly encounter new hurdles, new experiences, and new expectations. At times, I question if I understand the magnitude of how much I need to do to accomplish a task. Checking with others who have done it before or are experts in that field helps me get validation and overcome the doubt that leads to imposter syndrome.”

On the plus side, it could be a reality check. A reminder of what we’ve achieved and are capable of. We can use fear as an inspiration, a drive, an anchor to keep us true to ourselves. When asked about that viewpoint, Annalee reflects, “You should identify if your anxiety is coming from fear or imposter syndrome. Then, you can work on getting beyond it. You have to become very self-aware for preservation and success.”

A survey by NatWest found that imposter syndrome stopped 60% of women from starting a company. [3] For Annalee, this manifests most in networking.

“I was always taught to be humble, especially as a female. It’s very hard for me to upsell myself. I feel an ick when I have to talk about how accomplished I am.”

Witnessing the achievements of her team and her company keeps Annalee grounded and reminds her she is on the right track.

“A moment I truly knew I was in the right spot was a very large event that we executed. My business partner was the lead on it. I walked to see the beautiful space, the lighting, smell, music and energy coming from the people overtook all my senses. I knew then, this is where I’m supposed to be. This is what I’m supposed to be doing.”

The takeaway from Annalee’s experience is that imposter syndrome will ebb and flow. It will show up at inappropriate and inopportune times, but if you focus on building a community and network to support you, celebrate you, and keep you grounded, it will become easier to recognize when imposter syndrome begins to bubble up and stand in the way to achieving your dreams.  

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[1] Impostor Phenomenon Study: Most Entrepreneurs Affected,

[2] Over three-quarters of UK business leaders have experienced impostor syndrome, Connor Campbell,

[3] 60% of women put off starting a business due to imposter syndrome,–of-women-put-off-starting-a-business-due-to-imposter-syndrom.html

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