Bite-Sized Teaching Series: Ambition and Doubt
26 Dec 2025 · 13 min
Ambitious people often get stuck in self-doubt not because they're wrong, but because they're avoiding uncomfortable feelings rooted in past criticism or fear of what success might cost. The fix isn't more analysis: place your hand on your heart, breathe, and welcome the doubt like you'd welcome a child. That shift from resistance to acceptance is what lets you move forward.
Chapters
In my career, there's been a thousand times where I've met somebody who is deeply ambitious, where they want to achieve great things, even just big things, but they get constantly held back because they doubt themselves. And the way that they doubt themselves, it just slows or stops all the progress that they're making in their ambition. And the secret that nobody tells you is that There are very successful people. I work with some of the most successful people in Silicon Valley, and they all have doubt too. The only difference is that they listen to that signal, the signal of doubt, and they know what to do with it rather than to let it stop them. There's two places that doubt comes in. The first one is you're handed a project, or you have a project that you want to start, and you get excited about it. You're thrilled, maybe a little, but you're like, woo, let's do this project. And then you put some ideas together, you sit with the ideas and then doubt shows up. The second place where doubt typically arises is then you put it in front of somebody, maybe it's your boss or maybe it's an investor or maybe it's your husband. And you put this idea out, you make a presentation or you just talk about it. And you see that they aren't completely bought into the idea. And then you have even more doubt. And so these are the two places typically where the doubt arises. One is just when you're thinking about living into it. And the other one is when you get a reaction that you don't particularly want. Uh, and then those things actually increase the doubt in your system. So in either case, what's happening is that you have an ambition, which means you want to move something forward. And you're scared that there's going to be a feeling that arises in you that you don't want to feel. And the doubt is coming up as a way to protect you from that feeling. And typically there's two ways in which that happens. It is a feeling from your past that you don't want to relive. And the second one is that there's a feeling of maybe in failure or an accomplishment of that ambition, which you're scared will rock you. And so in either case, whether it's a, a feeling that's from your past, or whether it's a feeling that you potentially will feel, they're both emotions that you're trying not to feel, which are creating that doubt. So let me explain to you how that works, and then also show you a trick in a bit that's going to allow you to prove to yourself that this is about emotions, and it's really not about the logic that your doubt is telling you it's about. So the first one, the The one about feeling something from your past. This happens for a lot of folks. The way it happened for me was my dad would just criticize me all the time. So maybe it was because he drank too much the day before, his blood sugar was bad, or maybe because he didn't understand what I was doing. And I would say something, "Oh, here's my idea," and I'd get criticized for it. Or maybe he would even get angry at me for it. And as a kid, what you think is, "Oh, if I'm being criticized, I must have done something wrong." What do I do to fix it? What did I do wrong? And so that's the doubt. That's where the doubt comes from. And you can see this all the time. There are some people that I see, some executives, and whenever anybody gets angry at them, they go right into doubt. Or if somebody gets passive-aggressive with them, they go right into doubt. Or if somebody's critical of them, they go right into doubt instead of saying, oh wait, maybe how much do you understand the whole thing? Or, Right, so they don't get it, but most people don't get it. It's a new idea. That makes sense. They don't do any of that stuff. They just boom, go into doubt because they don't want to feel that friction because that's what they learned as a kid is that if I am feeling that friction, it means I must have done something wrong. And what do I do to adjust? So that's one. One feeling is someone's mad or critical of you. And it reminds you of something that happened in your past. That's one way that we go to doubt because we don't want to feel that. The other way that we go to doubt that we don't wanna feel it is, okay, I'm gonna do this thing and I might fail. Oh my gosh, I'm gonna feel horrible about myself. I don't wanna feel horrible about myself, so I'm gonna go into doubt. Or I might succeed. And then the person who I think I am, the person who's struggling, I won't be that person anymore. I'll be the person who's actually winning. And though a big part of my system wants it, there's also a part of me that's scared. Like, will I lose my ambition if I'm winning? Will I lose the people who love me? Will I be the tall poppy that gets cut if I'm winning? And so there's lots of reasons that you can have a fear of success or a fear of failure. And that brings up emotions that you don't want to feel. And so you go into doubt because what the doubt is doing is it's slowing your ambition. So you're not going to have to feel the thing. You're not going to have to take the risk of having somebody get angry at you or somebody criticizing you or feeling like you're the tall poppy or feeling like you're a complete failure. And so you just have doubt. And then that slows the process down. And then you don't do the thing and you don't have to feel that. The only thing you have to feel is disappointment with yourself, which typically you're used to feeling. You've been feeling it for years. So that's the safe bet. And so that's where you go. Right about now, what's happening is like, no, Joe, this isn't about feeling an emotion. I actually just don't know if something is right or something is wrong. So let's talk about why that isn't true. Why it's not true is because you don't know if it's right or wrong. You, you cannot know if you're right or wrong. How could you? You haven't done the thing before. If you've done the thing before, you knew how to do it, there would be no doubt. You also would have already felt all the emotions you would have to feel for doing the thing, right? You've done it before, you felt the thing before, there's no issue. So it must be that you don't actually know the answer. And of course you don't know the answer. Do you think that Sam Altman knows the answer to how to build the perfect OpenAI? Do you think that a cartoonist knows the answer of building the perfect cartoon? No, there's no way that you can know how to do anything perfectly, do it the right way. The only thing that you can do is just do it and then do it better and then do it better and iterate and learn and grow. That's the only way this gets done, but all of that stops If you are worried about feeling a certain way, if you have doubt, then you stop the iteration, you stop the process. So the only way to get to intellectual clarity is to actually do it. You can take your best guess, but you're going to fail sometimes. Everybody fails sometimes if they're doing anything of significance. And intellectually, you know that, but you're still being stopped. And that's why we know it's an emotional thing. But the other way we know it's an emotional thing, it's about avoiding an emotional state, is that when you learn what to do when you're avoiding an emotional state and you see that it brings you to clarity, boom, it becomes very clear. Because intellectually, you've mulled it over 1,000 times. Intellectually, you've weighed it, you've written the SWOT, you know, analysis. You've thought, do I do it this way? Do I do it that way? And none of that has gotten the doubt to go away. All the intellectualization doesn't actually stop the doubt. What stops the doubt is the emotion. And what's really happening there is if you can welcome that emotion, the doubt goes away. If you can say, oh, I can't wait for somebody to criticize me, the doubt goes away. If you say, I can't wait to feel like a failure, the doubt goes away. If you say, I can't wait to feel that massive success, the doubt goes away. And so let's do an experiment that shows you exactly what I'm talking about. So there's this great quote, and I think it is from someplace in South America, where it basically says, "Doubt is the sin of the heart." So what does that mean, doubt is the sin of the heart? It means that your heart has to be closed to have doubt. So heart closed means that we're defending against something. And in this case, we're defending against an emotion. So if you open your heart and then you go into the thing that you have doubt about, something different happens. So before we go there, a lot of people are gonna be thinking, "What do you mean open your heart, Joe?" And you know what I mean, you do. You're like, there's some part of all of us that knows what it means to open our heart. But in case you're so in your head that you don't know what it means to open your heart, Think about it like this. Think of something that you just love, that you just adore. Maybe it's a puppy or a kid or a person or a place or a tree, just something that just makes you feel, "Oh, I love being in the presence of this thing." And that is what it means to open your heart. And so your job is to love being in the presence of the thing that's creating doubt. So if you open your heart to the doubt and just sit there, so let's go ahead and do it. You open your heart to the thing that you're doubting. So pick a moment, pick a thing in your life right now that you have doubt around, anything. And then put your hand right there on your heart. So you're remembering, it's just to help you remember to open your heart, drop the defense, and look at that thing That doubt, that thing you're doubting, look at it the way that you look at that kid or that puppy, just with that welcoming, that openness. Take a deep breath in, really drop the defense, open your heart. What happens to the doubt? Where does it go? So immediately what we see is that as we open, as we welcome, the doubt starts drifting away. And we might not know everything to do in that moment, but we know the next step. You know right now what the next step is because you opened your heart to it. And if you don't, you know that you'll know the next step if you sit there with an open heart long enough, right? Because you're welcoming it. So that's how it works. But in the long term, it's really important to feel the actual emotion that you're avoiding, to really feel what is it like. Oh, to have somebody angry at me, how do I welcome that? To have somebody criticize me or be passive-aggressive, how do I welcome that? To have my boss go, "No, you're an idiot," how do I welcome that? And there's intellectual ways to do that. There is, oh, every time I'm triggered, I know that there's something that is holding back my freedom, and I can actually love being triggered. And I actually love being triggered because I know, oh, on the other side of that trigger, if I do the work, I'm going to find freedom. So of course I love it. It's like finding the beginning of a gold mine. I have to do a little digging, but man, if I know that there's gold down there, I'm going to take it. And so how do you really love the fact that you find this thing that you don't want to feel? Because you know, if you can enjoy feeling it, there's going to be a lot more freedom in your world. So there's the intellectual way of doing it, but the other way to do it is to do something that we call emotional inquiry. We have a whole podcast on it. We have an exercise that you can download on it. You can just look below where you're bringing wonder where you're bringing just that childlike excitement and curiosity to the emotional experience. So you're literally, what does it feel like in my body? How do I, how do I play with this thing? Is it dense? Is it, what color is it? How does it move? What's the sensation of the emotion? Where you're really bringing that wonder, that deep wonder into the emotional experience so that you can start really learning how to welcome it. Because the thing about emotions generally is that if you resist the emotions, they're really uncomfortable. It's like resisting going to the bathroom. It's really uncomfortable. Going to the bathroom, not so uncomfortable. Feeling the emotion, not so uncomfortable. It's really simple. Or you can also intellectually just see that it could be really exciting to welcome this emotional experience. And so if you are in doubt You can open your heart. Make sure that you're not committing a sin of the heart by closing your heart and allowing yourself to accept any kind of emotional experience that you're having, which really means accepting yourself as you are.
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