How to Combat Imposter Syndrome by Breaking the Cycle of Self-Doubt

October 31, 2025

Published in:

Entrepreneurial Well-Being

Four women pose with a statue of a golden bull in New York City. — Photo by Entrepreneurs' Organization

Imposter syndrome is the persistent feeling of being a fraud despite evident success, competence, or accomplishments. Those experiencing it often believe they’ve fooled others into thinking they’re more capable than they truly are, and they live in fear of being “found out.”

While imposter syndrome affects people across professions, it’s especially prevalent among entrepreneurs, who often operate in high-stakes, high-visibility environments with little external validation.

“The insidious nature of imposter syndrome is far from a rare occurrence in the entrepreneurial world,” said Chantel Cohen, EO Atlanta. “In fact, an overwhelming 84 percent of business owners report struggling with imposter syndrome at any given time. Even the most accomplished individuals are not immune to its grip.”

How Imposter Syndrome Shows Up for Business Owners

Entrepreneurs face unique pressures that make them particularly vulnerable to imposter syndrome. A few of those include:

Wearing multiple hats. Founders often juggle roles from CEO to marketer to customer service rep. The constant learning curve can trigger feelings of inadequacy.
Isolation. Many entrepreneurs work alone or in small teams, lacking peers to normalize their struggles or celebrate their wins.
Comparison culture. Social media and startup success stories can create unrealistic benchmarks, making entrepreneurs feel like they’re falling short.
High expectations. Investors, clients, and even employees may expect founders to have all the answers, which can amplify self-doubt when they don’t.

Common thoughts that may indicate you are suffering from imposter syndrome include:

"You’re not an imposter—you’re a work in progress, just like every great leader before you."

— Richard Levychin, EO New York

“I don’t deserve this success.”
“I’m just lucky.”
“Soon they’ll realize I’m not qualified.”

Entrepreneurs are constantly learning new things, building products or services that have never existed before, managing new levels of growth, and leading larger and larger teams as their companies expand. That constant state of learning can leave even the most confident founder wondering if they are qualified for the challenges they face daily.

“Imposter Syndrome is a legitimate mental state where an individual doubts their skills, talents, or accomplishments and has a persistent, internalized fear of being exposed as a fraud,” said Miranda Naiman, EO Tanzania. “I stay focused on my ‘why’ and remind myself that I am qualified, valuable, and contributing positively. My core values of Stay in the Light, Feed the Family, and Service Before Self are my true North. Everything else falls into place from there.”

Strategies to Combat Imposter Syndrome

Overcoming imposter syndrome isn’t about eliminating self-doubt entirely — it’s about learning to manage it and build confidence over time. Here are eight practical strategies for entrepreneurs:

1. Recognize and Name It

Awareness is the first step. Understand that imposter syndrome is common and doesn’t reflect reality. Naming it helps reduce its power.

2. Document Your Wins

Keep a “success journal” or folder of achievements, testimonials, and milestones. Reviewing these regularly reinforces your competence and progress.

3. Talk About It

Share your feelings with trusted peers, mentors, or coaches — like your close colleagues in EO Forum or EO Accelerator. You’ll likely find others have felt the same way, which can be incredibly validating.

"I stay focused on my ‘why’ and remind myself that I am qualified, valuable, and contributing positively."

— Miranda Naiman, EO Tanzania

4. Reframe Failure

Instead of seeing mistakes as proof of inadequacy, view them as part of the entrepreneurial journey. Every successful founder has failed—often repeatedly.

5. Set Realistic Expectations

You don’t need to be perfect. Focus on progress, not perfection. Celebrate small wins and incremental growth.

6. Invest in Learning

Confidence often grows with competence. Take courses, read books, or seek mentorship to strengthen areas where you feel insecure.

7. Practice Self-Compassion

Treat yourself with the same kindness you’d offer a friend. Replace harsh self-talk with affirmations and encouragement.

8. Delegate and Collaborate

You don’t have to do everything alone. Building a team or outsourcing tasks can reduce overwhelm and reinforce your leadership.

“Since joining EO, my self-confidence has grown. I’ve been able to realize my unique strengths and identify where I need assistance. I’ve been able to rely on my staff when needed, and lead them through challenging customers, supply chain deficits, and out-of-the-box ideas,” said Johanna Bialkin, EO San Francisco. “I used to suffer from imposter syndrome, feeling like I was less than my fellow entrepreneurs. Now, I’m excited to grow into my skill set and lead my business into the future.”

Imposter syndrome doesn’t mean you’re broken—it means you care deeply about your work and want to succeed. By acknowledging it and using tools to manage it, entrepreneurs can reclaim their confidence and lead with authenticity.

Remember: You’re not an imposter—you’re a work in progress, just like every great leader before you.

Contributed by Richard Levychin, an EO New York member and partner at Galleros Robinson CPAs and Advisors, which hosts an informative Knowledge Center on its website where a version of this post originated.