Why High Achievers Still Feel Like Imposters artwork

Why High Achievers Still Feel Like Imposters

The Midlife Chrysalis

August 5, 2026

Do you ever feel like you're not good enough, even when you're succeeding? You're not alone. In this Wisdom Wednesday, Chip Conley explores why imposter syndrome follows so many high achievers and, more importantly, how to break free from it.
Speakers: Chip Conley, Derek Gale

Topics: Self-Improvement, Education

**Chip Conley** (0:00)
How do you turn your imposter syndrome into an explorer syndrome? And the explorer syndrome is the idea of, I am here to journey and get better at things. And if you're an imposter, there's a sense of like, I don't have the right to be here.

**SPEAKER_2** (0:15)
This is The Midlife Chrysalis. Welcome to Wisdom Wednesdays with Chip Conley and Derek Gale, your weekly conversation about thriving in midlife. Together, we explore the questions, insights and practices that help you live this chapter with more purpose, vitality and joy.

**Derek Gale** (0:32)
Welcome to The Midlife Chrysalis Podcast. This is another Wisdom Wednesday episode. My name is Derek Gale and I'm the CEO here at MEA. And I am here with our fearless founder, Mr. Chip Conley. Hey, Chip.
Hey. How are you doing? Good. Good. I feel like this is going to be one of those things I think a lot of us have suffered from, but this has been one of mine. And so, I'm going to get you to... We're going to go into something.
You get to play therapy for Derek in this one.

**Chip Conley** (1:02)
Okay. Let's do that. It's about time.

**Derek Gale** (1:07)
You know, imposter syndrome. You know, I remember when I was a young entrepreneur in my early 20s, standing up in front of my teams and thinking to myself, I have no frickin idea what I'm doing up here. You know, why are people listening to me? As my career grew, you know, I remember standing on stages and talking to people and you just got that voice in the back of your head. And I'm like, oh, just a little bit more experience, another win, another thing, it's going to go away. But I don't know if it ever does.
You know, you have this voice in the back of your head going, you know, are you really qualified to do this? Are you the right person? I probably shouldn't be telling you that I wonder if I'm qualified to run MEA. But we'll leave that discussion for another day.

**Chip Conley** (1:48)
I'll keep that. That's okay.

**Derek Gale** (1:51)
Why doesn't that ever go away? You've talked about this before.

**SPEAKER_2** (1:54)
I think it changes.

**Chip Conley** (1:56)
So do you feel like it's the same message? Is it sort of a broad message like, you're just not good enough, Derek, and it's sort of across everything? Or is it quite specific to certain things? Because I think when it's specific to certain things, you can grow out of that. For example, speaking in front of, in public, in front of other people. It's very easy for someone to feel like an imposter in that situation. And also, you feel very nervous because you feel like, who am I to be able to give a speech to this group of people? But as someone who hated that and had a lot of imposter syndrome on that when I was young, I have no problem with it today. I grew out of it. But if it's an imposter syndrome across relations, here's another one that actually I think is a broader one and it can be really hard for someone. I don't deserve love in a relationship. Or I'm not good as a lover or I'm not good in relationships. Romantic relationships, let's call it. That is one that I think, I certainly have that voice in my head sometimes.
That's a very old voice.
I think part of it sometimes is learning how to talk to the voice.
If there's a voice there and there's all kinds of work here. We've had Dick Schwartz come and do parts work, internal family systems. There are a variety of different kinds of methodologies and therapy to go through this. But the thing I like to see when I talk about this in MEA Workshop is I talked about the fixed and the growth mindset.
When I feel exposed at something I'm really bad at, my critic will come up. My fear of social comparison kicks in.
What I know from psychology is that performance anxiety associated with that is not going to make it any better. The most important thing for me to do in a time like that, and for me, the example I tend to use is the yoga class because I'm not very limber. I don't really enjoy yoga all that much. I do enjoy after a yoga class how I feel. But to be able to talk to myself such that I can see and I can name that state of mind I am in, and give it a funny, humorous name. I call it stiff upper chip. When I am in a yoga class or thinking about going to a yoga class, and thinking about how bad I will be versus everybody else, I talk to myself like a coach would talk to me, objectifying that state of mind and saying, oh, stiff upper chip, it's you again. You're here. What are you doing here? You know that after a yoga class, you enjoy it. You love how you feel. You know not everybody's looking at you. Don't be so egocentric to think that everybody's just staring at you. They're doing their own thing. In fact, if they're really good at yoga, they're just in their body. Maybe it's time for you to take a break and give the real chip, not stiff upper chip, that state of mind that you're trying to get out of. Let's just let chip sink into the experience and see how it is. Personifying it as a state of mind with humorous name, the reason the humorous name piece is important, according to Carol Dweck, the Stanford Psychology Professor, is because when we have imposter syndrome, or when we're a perfectionist, and when we have performance anxiety, what is at play in that moment is self-criticism. What we really need to do is to have some humor. Because if you have humor, it's hard to be self-critical.

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