An Entrepreneur’s Lessons: I’m Not an Imposter, So Why Do I Feel Like One?

Have you ever felt like you didn’t belong? Like maybe you’ll be exposed as a fraud if you open your mouth? Has that feeling ever caused you to shy away from sharing your ideas, expressing your opinions, or pushing back on decisions that you knew, deep down, were wrong? Then you might have felt what some people describe as ‘imposter syndrome.’ I’ve faced this feeling many times throughout my life and, of course, as an entrepreneur. Today, I want to dissect this phenomenon from various angles, challenge the traditional narrative using research that has helped me combat this feeling, and offer a fresh perspective that may help you understand what’s really going on.

The Traditional Narrative

Traditionally, Imposter Syndrome has been framed as an internal struggle — a lack of self-confidence. It’s like you’re the protagonist in a tragic play where the villain is your own self-doubt. It was first mentioned in a 1978 article by Pauline Clance and Suzanne Imes and referred to as the ‘imposter phenomenon.’ The original article coined the imposter phenomenon to “designate an internal experience of intellectual phonies, which appears to be particularly prevalent and intense among a select sample of high-achieving women.” This phrase has since morphed into what we now call ‘imposter syndrome.’ Forbes tells us that a staggering 70% of people experience these feelings at some point in their lives. But here’s the problem: the traditional narrative puts the blame squarely on you as if you’re the one who’s broken and needs fixing.

While the 1978 study was groundbreaking for its time, it also has its limitations. The study focused on one specific — albeit very important — demographic while often ignoring the context in which that demographic (women) operates. Furthermore, it proposes “therapies” to address what they say is the issue — your mind. In this narrative, we’re still largely talking about Imposter Syndrome as if it’s a solo journey through self-doubt, without considering the external factors at play. The authors even conclude:

As a result of a combination of such therapeutic interventions in conjunction with a commitment to change, a high achieving woman who has previously considered herself an impostor begins to allow herself to state and feel, “I am intelligent. I have learned and achieved a tremendous amount. It is all right for me to believe in my own intellectual abilities and strengths.” She begins to be free of the burden of believing she is a phony and can more fully participate in the joys, zest, and power of her accomplishments.

An Alternative View

So it’s clear: the traditional narrative around Imposter Syndrome puts the onus on the individual. But what this traditional view lacks is context. What if the system you’re in plays a significant role in these feelings of inadequacy? This is where the alternative view comes in, as brilliantly discussed by Christine Liu and Jodi-Ann Burey in a fantastic interview they did for the Harvard Business Review.

They argue that the term “Imposter Syndrome” can sometimes be a smokescreen that distracts us from systemic issues like lack of diversity, unequal pay, and opportunity gaps. It’s not just about you doubting your accomplishments; it’s also about the environment that fosters this doubt. What we see now is that the traditional view wasn’t necessarily wrong, just incomplete. Feeling like an imposter can be a vicious circle of individual feelings of inadequacy further exacerbated by the environment in which those feelings are felt, leading to even worse feelings, and ultimately to burn-out.

The Checklist: A New Approach

So, how do we navigate this more complex landscape? Jodi-Ann Burey offers a helpful checklist of questions that serve as a diagnostic tool to understand what’s really causing these feelings. This isn’t just about self-reflection; it’s about situational awareness. The checklist helps you identify whether it’s truly a lack of self-confidence or if there are external factors at play.

Here are the questions:

1. What is making me feel like an imposter right now?
2. When else have I felt this way?
3. Is there a trend or pattern that makes me feel like this?
4. How does it compare to this time?

By answering these questions, you’re not just introspecting; you’re also examining the system you’re a part of. It’s a holistic approach that takes into account both individual and systemic factors.

Here’s how I answered these questions in the context of my early entrepreneurial journey:

What is making me feel like an imposter right now?

I felt immense pressure during early investor pitches to be “perfect.” Despite having a solid team, I questioned my worthiness and struggled with the thought, “Why me?” We’re asking for millions of dollars — why would they ever give it to me? Why am I worthy? It took multiple successful pitches and therapy sessions to reframe that doubt into a more empowering mindset: “Why NOT me?”

When else have I felt this way?

I experienced similar feelings when applying to graduate school. I was rejected by all five programs (100% rejection) during my first application cycle. I really questioned whether I was “worthy” of even attending business school. But I persisted, doubling down on GMAT and appliation prep, and re-applied, eventually getting into my first-choice program. Despite my career achievements, I still felt like I had to prove I belonged there every day.

Is there a trend or pattern that makes me feel like this?

I often feel undeserving of my success, especially when around people who seem at ease with theirs. This feeling is particularly strong when I’m in environments where I perceive others as having more privilege or a “legacy” of achievement. Factors that have made me feel this way in the past include: perceived education gaps (I went to a state school, many people I spend time with went to Ivy Leagues), socioeconomic gaps (I grew up in rural South Dakota), comparative beauty (I’ve often struggled with body image), etc.

How does it compare to this time?

The trend persisted during my startup’s later fundraising rounds. Part of this was my constant comparison to my two co-founders, both of whom had prior investing experience. I felt like the odd one out, questioning my worthiness. Yet, we successfully raised multiple funding rounds, leading me to question if perhaps I was just lucky. It never occurred to me that, perhaps, I actually was worth investing in.

Upon reflection, I clearly felt like an imposter. Prior to more deeply researching the topic, I would have reacted to these feelings with shame — that I was somehow just acting “weak. ” That I should just “shut up and get over it.” But what I see now when I read these answers is that there was a combination of internal factors (the way in which I view my own achievements, my innate self-confidence or lack thereof, my feelings of worthiness) and external factors (fear about being judged by VCs, how I compare myself to others, the judgment of others on my applications).

This has allowed me to separate what I can control from what I cannot. It’s also given me the ability to address the harshest feelings head-on in therapy and coaching while allowing others to simply fall away. For me, naming the problem oftentimes reduces or even removes the power that the problem holds over me. It’s helped me become more confident in myself.

Actionable Steps for People and Companies

We’ve talked a lot about the problem, but what’s the game plan? How can you take back control? Whether you’re an entrepreneur, a manager, or an individual contributor, you’ve got the power to shape the culture around you. Don’t wait for someone else to make the first move. Be the catalyst.

First off, let’s talk about what you can do as an individual. Start with Jodi-Ann’s checklist. Ask yourself those questions and dig deep — be honest with yourself. Gill Corkendale, a London-based executive coach and former management editor at the Financial Times suggests, among other things, that you also:

Consider the context. Most people will have experience moments or occasions where they don’t feel 100% confident. There may be times when you feel out of your depth and self-doubt can be a normal reaction. If you catch yourself thinking that you are useless, reframe it: “the fact that I feel useless right now does not mean that I really am.”

But don’t stop at introspection. Gill also recommends that you seek support and “talk about your feelings. There may be others who feel like imposters too — it’s better to have an open dialogue rather than harbour negative thoughts alone.” Christine, from the HBR interview, recommends “finding a community of people who share your experience.” You’re not alone in this, and sometimes the best medicine is simply knowing that.

For organizations, it’s not enough to just talk about diversity and inclusion; you’ve got to walk the talk. As we’ve explored, feelings of imposter syndrome can be caused by systemic issues, not just an individual failing. To address these issues, organizations can start by creating mentorship programs, fostering an inclusive culture, and most importantly, addressing unequal pay and opportunity gaps.

Let’s not forget the role of leadership. If you’re at the helm, you’ve got a responsibility to set the tone. Janice Omadeke, the CEO and Founder of The Mentor Method, emphasizes that the best leaders are “those [who are] willing to practice vulnerability on a deeper, personal level, and adopt it as a principle, are those who will be credited with building a more equitable and innovative world of work — a world that the next generations want to see.” That starts at the top. Be open about your own experiences and challenges. It not only humanizes you but also makes it easier for others to speak up.

Next Steps TL;DR

For Individuals:

• Self-Reflect: Use Jodi-Ann Burey’s checklist to identify the root causes of your feelings.
• Find Your Tribe: As Christine Liu suggests, connect with people who share your experiences.
• Speak Up: Don’t keep your feelings bottled up. Open dialogue can be a game-changer.
• Reframe: Change the narrative in your head from self-doubt to self-assurance.
• Consider the Context: Understand that self-doubt can be a normal reaction in certain situations.
• Be Kind to Yourself: Allow yourself to make mistakes and celebrate your successes.
• Seek Professional Support: Don’t hesitate to ask for help or advice.

For Organizations:

• Establish Mentorship Programs: Pair less experienced employees with seasoned professionals and emphasize the importance of mentorship, particularly for traditionally marginalized employees (women, people of color, LGBTQX+, immigrants, former military, etc.).
• Create an Inclusive Culture: Make diversity and inclusion more than just buzzwords. Pivot the language employees use to describe themselves.
• Address Inequality: Tackle unequal pay and opportunity gaps head-on.
• Hold Yourself Accountable: Ensure employees are taking advantage of these programs and check in with them through listening tours, culture surveys, and other means.

For Leaders:

• Set the Tone: Create a culture where vulnerability is not a sign of weakness and, most importantly, model the behavior yourself.
• Be Transparent: Share your own experiences and challenges to encourage others to do the same.
• Take Action: Don’t just talk about change; be the catalyst.
• Mentorship: Assign mentors wisely, and make sure your company’s program is being used.

Conclusion

We’ve covered a lot of ground here. From the traditional narrative that puts the onus on the individual to the systemic factors that often get swept under the rug, we’ve learned that Imposter Syndrome is a complex beast. But it’s not unbeatable.

We’ve got to stop thinking of Imposter Syndrome as just an “inside job.” It’s not solely about fixing yourself; it’s about recognizing the larger systems at play and taking collective action. Whether you’re an entrepreneur, a leader, or someone just trying to make it through the day, you’ve got the power to change the narrative.

So, let’s get to it. Use that checklist, lean on your tribe, and don’t be afraid to shake up the system. Because, at the end of the day, the only real imposter is the voice in your head telling you that you can’t make a difference. And that voice? It doesn’t stand a chance against a well-informed, action-oriented you.

I’d love to hear from you! What strategies have worked for you in combating the feelings of imposter syndrome? How have your organizations addressed the systemic issues? Drop your thoughts in the comments below.