I Interviewed 25 People About Impostor Syndrome. Here's What They Said (and How They Overcame It).
Glasp’s note: At Glasp, we value the close personal relationships we’ve built with thinkers, creators, and doers who fuel curiosity and growth. This week, we spotlight Bobby Powers —a lifelong learner passionate about leadership development and continuous improvement. With more than a decade of experience leading teams and developing learning and development at startups, Bobby understands the transformative power of curiosity and mentorship. You might remember him from his Glasp Talk appearance, where he shared insights on leadership and personal growth, inspiring thousands. We’re honored to continue learning from Bobby and are thrilled to share his thoughtful reflections with our community.
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Hi Glasp Community!
I’m Bobby Powers, and I run the Leader & Learner publication on Substack. I write two posts per week that will help you become a more curious leader and learner.
I’ve been leading teams and training managers for over a decade. One of the biggest things that has surprised me over the years is how many people—even senior executives—struggle with self-doubt. In fact, some of the people I admire most have admitted to me that they sometimes feel like a fraud.
That comforted me because I’ve also felt like a faker multiple times in my career—most acutely when I got a big promotion and was suddenly put in charge of a department of 160 people.
These feelings of impostor syndrome are way more common than you may suspect. Because everyone I’ve trained struggles with the same self-doubt, I decided to dive a bit deeper to hear what tactics have helped various leaders feel more self-confident.
I asked 25 leaders across six countries (USA, Costa Rica, Germany, Bosnia, the Netherlands, and the Philippines) about their experiences. I learned a lot from what they shared, and their tips can help you regardless of your role or career stage.
Essentially, Their Advice Fell Into Two Camps:
Embrace the self-doubt: You could call this the Eastern Philosophy perspective. Eastern religions often emphasize recognizing what you’re feeling and not immediately trying to change it.
Challenge the self-doubt: This is more of a hallmark of Western Philosophy. Rather than embracing the feeling, many managers described tactics they’ve used to convince themselves they belong and that they’re just as qualified as anyone.
Personally, I’ve always fallen into camp #2, but I learned a lot from the insights of camp #1. There’s no right answer here. The key is to find what perspective works best for you—what helps you become the employee, leader, and human you want to be.
Let’s break down the two camps…
Camp #1: Embrace the Self-Doubt (Eastern Mindset)
“We cannot change anything unless we accept it. Condemnation does not liberate, it oppresses.” -Carl Jung
The leaders I spoke with who embodied this perspective were primarily focused on observing their own behavior and learning from it. They thought the fraudulent feelings could teach them something or—at the very least—keep them humble.
A senior leader named Jasmina relayed a perspective that was once shared with her: “The people who should worry about impostor syndrome are the ones who never question themselves.”
She explained, “Instead of viewing self-doubt and feeling uncertain as evidence that I do not belong, I have learned to see it as proof that I am pushing my boundaries, which is exactly where growth happens. I have also learned that criticism and discomfort are part of leadership, not indicators of personal failure.”
“The truth is, impostor syndrome never fully disappears (at least in my experience),” said Jasmina. “And that is probably a good thing. My goal was never to eliminate the doubt but to acknowledge it, thank it for trying to keep me safe, then act with courage anyway.”
A leader named David, who oversees offices in two countries, said he has stopped viewing impostorism as a negative thing. Instead, he just accepts it for what it is:
“Honestly, I had to completely flip how I thought about it. Now (but not always) when that feeling creeps in, I try to take it as a good sign. Basically, I try to look at it as meaning that I’m actually pushing myself and growing. If I’m feeling too comfortable all the time, that’s when I start worrying I’m getting complacent.”
An executive vice president of sales named Molly agreed:
“I remind myself that the people that I look up to and admire most likely have felt this same feeling. And I remind myself that it’s normal to be scared when you’re pushing yourself out of your comfort zone, BUT you can’t grow as a professional unless you do it. All of my most rewarding jobs were the ones I was slightly terrified to take. But that also means I’m taking the right leap—if it feels too comfortable, it likely means it’s not too much of a challenge.”
Another leader named Igor said something that summarizes camp #1: “Don’t fight the feeling—acknowledge it and try to separate feelings from facts.”
Camp #2: Challenge the Self-Doubt (Western Mindset)
“If you listen to your fears, you will die never knowing what a great person you might have been.” -Robert H. Schuller
The majority of the leaders I asked about impostor syndrome fell into camp #2. They talked about tactics they use to try to reframe the topic or overcome those feelings.
The most common thing I heard from people in camp #2 was the power of talking to others about impostorism.
A senior leader named Scott said, “The first tip is recognition that everyone experiences it, and those who don’t are lying. You’re never alone, so surround yourself with a strong network and talk about it. I love the concept of, ‘You have to name it to tame it.’”
“Others feel it too,” said a director named Merima. “Speak about it to realize that you’re not alone...Many people go through it. When you realize it’s so common, it becomes easier to handle.”
Several people shared techniques for reminding themselves of their accomplishments to boost their self-confidence.
Aina in the Philippines: “One thing I do now is screenshot kind messages/feedback or Employee Appreciation notes I received and send them to myself on Teams, so I can revisit them whenever self-doubt creeps in.”
Ilma in Bosnia: I started to put my focus on smaller issues and wrote down all the accomplishments I made since I joined the team. Visualizing the success really helped me see that I’m not just facing failures, but actually achieving a lot.”
Mariana in Costa Rica: “Every time someone compliments something I’ve done, I take a screenshot and save it.”
Another big theme leaders shared was the importance of not comparing yourself too much to others, especially those who have more experience or different strengths than you do. A leader named Kelly put it well:
“One of the most effective strategies I’ve adopted is to stop comparing my success to that of others. Each person has their own unique strengths and abilities. Learning to focus on what sets me apart—and investing in the continued development of those qualities—has been essential to overcoming imposter syndrome and building confidence.”
The people I spoke with also had different perspectives on whether to fake confidence. An accounting manager named Justin was all for it:
“My honest advice, as cliche as it is, would be to fake it til you make it. I was put into this position for a reason, my superiors had faith in me and my abilities, it’s only MY own head getting in the way. So to some extent, I’m constantly ‘faking it,’ in the sense that my natural tendency is to let others lead and solve problems—I’m faking it to myself when I’m confident and assertive, if that makes sense.”
But a leader named Tiffany had this to say:
“…I also hate the ‘fake it till you make it’ mindset. Instead, I focus on being the version of myself I want to grow into. As Mel Robbins puts it, intentionally act like the person you want to be. For me, that means showing up as an approachable, decisive, and empathetic leader—not perfectly, but consistently.”
Several leaders I spoke with also emphasized the power of finding a mentor or building an intentional community of support around you.
“I’d recommend finding a support system to lift you up and shine lights on the parts of yourself that you can’t always see clearly,” said a director named Ashley. “Whether that’s friends (old or new), networking events, mentorship, finding the right people to share ideas and even insecurities with is a game changer.”
Conclusion
Personally, I still feel like a fraud sometimes, but the feeling comes around less often than it used to. I’ve employed many of the tactics above in my own life, and I find a lot of wisdom in both camps: accepting the feeling and actively trying to challenge it.
I can’t tell you which approach will work best for you, but try each one on and see how it fits.
And if you want to read the full list of impostor syndrome tips I gathered from these 25 leaders, I compiled them into a PDF guide and even paid a graphic designer to illustrate it. You can download the free guide here.
Have you struggled with impostor syndrome? If so, what helped you process those feelings? Drop us a comment below.
Btw, if you’re interested in getting two posts per week with book recs and personal development tips, I’d be honored for you to subscribe to Leader & Learner.
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🟥 Glasp Talk with Bobby Powers:
Glasp Talk features intimate interviews with luminaries, revealing their emotions, experiences, and stories. The guest, Bobby Powers, is a dedicated learner passionate about leadership and personal development. With over a decade of experience managing teams, leading onboarding, and Learning and Development programs at various startups and SMBs, Bobby is also an avid reader, having read over a thousand books in the last 15 years.
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Thank you, Bobby! It is incredibly thoughtful and grounding. I’m grateful for how openly you share both your experiences and the wisdom of the leaders you interviewed. Your framing of impostor syndrome as both something to learn from and something we can challenge is especially powerful.
We appreciate you putting this together and continuing to help so many of us grow!
This is an important aspect of teaching that is not discussed very much. A light Elicit sesrch found a few articles - https://elicit.com/review/787c1011-891f-4191-bff0-50737fd833be