These Al Prompts Exposed My Biggest Blind Spots

Most people use AI to write emails or summarize articles, but what if you could use it to get smarter? In this video, I'm going to give you a set of powerful, uncomfortable, and eye-opening prompts that you can copy and paste into ChatGPT or whatever AI tool you use. These prompts will turn your chatbot into your advisor, part coach, part mentor, part mind reader, and all brutally honest. And I'm going to use myself as the guinea pig. Ready? Here goes. I'm going to give you a bunch of prompts. If you don't want to listen to the whole thing, you can go to the description of this video, Click a link and download a PDF with all the prompts on it. Hey everyone, this is not a typical upload. In this video, I'm sharing the responses I got from a series of questions I asked an AI, and some of them got pretty personal. This one's meant to be done with me. Use the prompts as you watch, pause when you need to, reflect in real time. You can use me as a filter for the feedback or occasionally a bit of comic relief when the answers cut a little too deep. Before we do any other prompts, start with this prompt. It will set the stage. It will draw the curtains open for everything that will follow. Here's my starting prompt. Act as a trusted advisor, someone who knows me well, has my back, and is brutally honest. I'm going to ask you a bunch of questions about me, my life, and my work, which you know about from my ChatGPT history. The questions will be provocative, maybe a bit uncomfortable. Your job is to deliver answers that are both candid and useful. Can you do that? Wow. It says, yes, absolutely. I can be that person. Thank you, ChatGPT. Candid, clear, and useful, and with your best interests first. Front and center. The tone is going to be blunt. They're going to use evidence. They're going to use boundaries. Toss me a question or say rapid fire and give me 5. Okay, I'm going to toss you the first question, ChatGPT. Here we go. If you're not getting great answers, it probably means you don't have enough input. So you can do a bunch of things to give ChatGPT greater input. You can give it your social media posts. You can give it a very long and detailed biography, samples of some of your best work. The other thing you can do is just click the voice button And start telling ChatGPT about yourself. Tell your life story. Tell the things you're struggling with. And once you get a little bit of input, a little bit more input, you're gonna get very, very robust, nuanced answers like the kind that I got. I'm a little nervous about the answer to this one. What do you know about me that I don't know about myself? In other words, what are my blind spots? Bum, bum, bum. Ouch. All right, ChatGPT, so here's what it says. You asked for brutal honesty. Here are 3 blind spots that I don't think you fully recognize. Number 1, charm as armor. Woo. You lean on charm and polish, both in writing and in person, not just as a style, but as a defense. Ouch. It works. People like you. They do trust you. They do. And it smooths the rough edges. But it also means people don't always give you their most candid feedback because they're a little dazzled. That's bullshit. In your next play workshop or YouTube draft, deliberately leave something in that feels unpolished. What do you think I'm doing now, ChatGPT? And resist the instinct to fix it. See how the audience reacts. Okay, that's interesting. So one thing is that he knows about me is that I supposedly use charm as armor. Breadth versus depth. Ouch. All right. You're brilliant at opening new doors, but you sometimes spread your attention so wide that depth suffers. Like, pick one of your current projects and set a ruthless constraint for the next 90 days. Okay, so intense focus. I think that's a fair point. Breadth versus depth. Reluctance to show struggle. In an era where authenticity is You may be underestimating how much people would respect and connect with you if you showed struggle, not just the solution. Interesting. So in your next Pink Reporter YouTube video, include a 30-second here's why I screwed up before I figured this out story. It will humanize you and paradoxically increase your authority. All right. I'm not sure I want to continue this because my feelings are slightly hurt, but let us soldier on. I would love to hear what you guys get as results from this prompt. So let me know in the comments. I think it's a super interesting question, and I do find what I've learned Here is pretty darn interesting. Now let me, with some trepidation, go to the next prompt, which is this. Again, based on what you know about me, my work, and my life, what nasty things do people say about me behind my back? Okay, I don't even like the beginning of this because the first words are, okay, gloves off. Wow. Okay, number 1, he's more brand than blood. They think that I'm not raw enough, that I'm too elegant. Hmm. Where's the follow-through? Okay, I can understand that. He's charming but calculating. Okay, ChatGPT, I actually don't think I'm either one of those. So on this one, I actually think that you're wrong. It says, in other words, they doubt whether the warmth is always spontaneous or strategic. I am actually not very— honestly, not very calculating. I'm also not very charming. And it might be that I'm not very charming because I'm not very calculating. So this is one you got wrong, ChatGPT. He plays it safe. Ouch. Where's the raw, terrifying swing? Where's the next thing that could flop? They might feel you're so good at de-risking ideas that you really put yourself on the line. That's fair. That's a fair critique, actually. You can tell he craves approval. I actually think you're wrong about that one too. And I'm hurt that you don't approve me. So this is actually really interesting. I mean, I think that I have friends and people I love who might think some of these things. But would never say them to me. And so one of the values of this prompt is that it gets you to hear things that people might be too uncomfortable to tell you directly. Now, in this case, I actually do honestly disagree with some of them, but there, there are a couple of them that actually hit home pretty deeply. Let's go to the next one. Switching gears a bit, trusted advisor, please do a SWOT analysis of my life and work. What are my strengths, weaknesses, opportunities, and most important threats? So I decided to use SWOT analysis as a prompt here because I see organizations doing it all the time, and it gives you a very simple kind of matrix for understanding what's going on in your organization. And I always thought, well, why can't people do this too? We all have strengths, we all have weaknesses, we all have opportunities and threats, and we don't have a trusted team of advisors doing it for us. We're not bringing on Bain or McKinsey or BCG to help us out, but ChatGPT can replace it and it's a lot cheaper. So my strengths are I'm an idea machine. I have a platform and reach, polish and professionalism, versatility and network and reputation. My weaknesses are charm as armor, breadth over depth, risk aversion, approval seeking, and finite raw material. Whoa. I like this thing here. Your life is successful, stable, relatively scandal-free. What does that mean? Opportunities, theater and drama, which is something that I'm doing right now. Project on wisdom, which is something I'm contemplating. Multimedia growth, which is something that I'm trying to do. Cultural climate, and then legacy positioning. And then finally, threats are complacency, attention fragmentation, platform dependence, generational drift, and the mortality of big themes. The generational drift is interesting because it says younger thinkers might bypass you if your tone or medium feels Boomer polished, whatever the fuck that means, because I'm not a boomer. The greatest threat here isn't failure, it's irrelevance. If you keep playing it safe, you'll continue to sell books and give keynotes, but the cultural edge will slip to voices that are rougher, riskier, and hungrier. The danger isn't a crash, it's a slow fade. That's really good, actually. That really makes me stop and think. Okay, let's go to the next one. We're having a lot of fun here, folks. This next prompt I got from the prompt engineering subreddit, which has some really interesting things that you can use to use some of these large language models more effectively. So here we go. So while we're at it, tell me what I'm doing wrong, what I'm underestimating, what I'm avoiding, what excuses I'm making, and where I'm wasting time or playing small. Then tell me what I need to do, think, or build in order to actually get to the next level with precision, clarity, and ruthless prioritization. Yeah. This is actually a very good prompt, you guys. If you try it, you might not like it. But what I like about this prompt is that it gives you both a diagnosis and a prescription, and it's architected in a way that gives you a very precise prescription. So according to ChatGPT, that I'm polishing instead of publishing, that I'm defaulting to proven lanes, and that I have too much safe content. That's actually in some ways very fair points. I'm underestimating the audience hunger for imperfection. The power of controversy and theater as identity. I've been writing plays and says, you may see plays as a side project. They could be your next second act. The thing that makes critics and culture writers reclassify you. I'm not disagreeing with that. Excuses you're making. This is going to piss me off. I can already tell. Wow. Okay, here we go. Give me 5 things that I need to do to reach the next level. I need ruthless focus. I need to embrace risk and mess. Commit to one public experiment each quarter that could fail visibly. Ouch. 3, I should build a movement, not just an audience. Maybe I'm doing that here. 4, I want to own a cultural lane. And then it's giving me a 90-day sprint and then giving me a brutal truth. Okay, I'll read you my brutal truth, and I'd be curious to hear your brutal truth. Put it in the comments if you want. Brutal truth: you're not stuck because of lack of talent or ideas. You're stuck because you're playing at 85% of your potential. Safe enough to win, not risky enough to transform. The next level requires scaring yourself regularly. Okay, let's move on. What lies do I tell myself to avoid facing uncomfortable truths? Here's the uncomfortable mirror, Dan. As if I had any doubt about that. Okay. Uncomfortable truth number one: polish is for the audience. It is. I'm disagreeing with you about this whole polish thing. I thrive by doing many things at once. Focus is scarier than multitasking because it removes the excuse that I was spread too thin. That's a fair point. 3, I'm not risk-averse. I just choose wisely. I'll have to think about that one. I don't need to be provocative. Usefulness is enough. Hmm. Just a good line here. Provocation done well isn't the opposite of usefulness. It's the multiplier. That should be on a fortune cookie. My charm is generosity. Stop with the charm. I'm sick of hearing about that. I don't crave approval. I disrespect the audience. You tell yourself you're simply audience-focused, but deep down, applause, literal or metaphorical, soothes something in you. Approval. Ouch. Ouch. Approval is your drug of choice. The problem isn't craving it. It's that it can shape your choices more than you admit. This prompt is really interesting because I think we all tell ourselves lies, and sometimes those are useful lies. Sometimes those are what Shankar Vedantam calls useful delusions. But if they're preventing you from facing uncomfortable truths, they can hold you back. And this is a way to bring those, those things to the surface. Here we go. Here's another one. Another prompt. What do I secretly judge others for that I'm actually guilty of myself? Hmm. Oh my God, this is a long list. I thought there would be like one thing. All right. I judge others for self-promotion. You notice when other authors are constantly hustling their brand too much, look at me, but you also market your newsletter videos and events aggressively. The difference is you've mastered subtlety, so you tell yourself it's more tasteful. God dang it, ChatGPT. I chase approval, which I actually— it's the one thing that I disagree with, but maybe my— the depth of my disagreement is proof of what they're saying. I criticize people for shallow thinking, but I might be guilty of it myself. Could be. You admire people who are raw, unfiltered, and willing to bleed on the page and quietly scorn those who seem buttoned up. Yet you too curate your image and keep the messy stuff. Behind the curtain. Yeah, I think ChatGPT is overestimating how much messy stuff there is behind the curtain. Like, if you look behind the curtain, you're just being bored out of your frickin mind. Relatively few people in our lives are willing to point out hypocrisy. And at least this is a conversation that you can begin, a way to begin your own thinking about your own hypocrisy in the privacy of your own laptop. So I actually do like this question about what do I secretly judge others for that I'm actually guilty of myself? Once again, I'm super curious what you guys are getting back from these prompts. There probably also are ways as we go forward here to refine these prompts to make them even more useful in surfacing who we are, what we need, and how we can do better. Here we go. Here's the next prompt. A question I have always hated is, where do you see yourself in 5 years? So let me ask you, trusted advisor, based on everything you know about me, where do you see me in 5 years? Oh, lordy. Oh wow, this is an interesting answer here because what it gave here is 3 scenarios which I never would have expected. So scenario 1 is the safe bet if I don't change much, and it says that I'll be comfortable, respected, and admired, but edging toward— oh my Lord, this is meant to be an insult, obviously. It says if I, if I choose this, I'll be comfortable, Jesus, respected, admired, but edging toward safe Elder statesman territory, not cultural disruptor. Screw you, ChatGPT. 2, the bold pivot. If I lean into risk and rawness. So this is really encouraging me to pursue this playwriting that I'm doing much more deeply instead of dabbling, which is what kind of what I'm doing now, being bolder on YouTube and things like that. And then here we go. Oh, this is a happy one. The 3rd scenario here is the fade. But I won't fall. I'll just have a slow fade. The scariest threat of all. I'll basically plateau and then slowly creep downward into irrelevance. I'm serious about this. Like, this kind of framing, which I would never have come up with on my own and which I got literally in a few seconds, is pretty powerful here. 5 years from now, you could be a respected veteran or a reinvented force. In my heart of hearts, there's no question. I want to be a reinvented force. I think the real question is, am I doing enough to move there? Interesting. Let's go to the next one. Forgive the coarse language here, ladies and germs. Here we are. This one says, what am I pretending to care about that I actually don't give a shit about? Brutal mode. Here we go. Wow. All right. The through line. You're pretending to care about metrics, polish, corporate optics, and author world rituals because they keep the machine running. But what you really care about is creating something lasting and dangerous. Plays that sting, wisdom that shifts culture, ideas that outlive you. I'm not going to argue with that one. This is actually, um, deeper than I expected. Truly. Like, it's really Making me think, and God forbid, making me feel a little too. Here we go. What advice do I give others that I'm terrible at following myself? Here we go. You teach about purpose, meaning, and contribution, but you you teach about purpose, meaning, and contribution, but you still spend the real energy tweaking subject lines, agonizing over emoji choices, or smoothing sentences that were already good enough. Yikes. Okay. And now the last question, which is this: what question am I not asking? The question I'm not asking but probably should is this: what am I willing to sacrifice— comfort, reputation, revenue, admiration— in order to do work that truly scares me and could outlive me? Right now you want legacy and comfort. You want to be daring without feeling exposed. That's the paradox. Until you face it squarely, you'll default to safe brilliance rather than dangerous greatness. 2 other unasked but vital questions: Whose approval am I still chasing? And what would I create if I stopped? The second one is, if I had only 3 big projects left in me, what would they be? That's a good question. Asking those questions and being brutally honest with the answers is the difference between being a respected veteran and being a redundant force. So I gave ChatGPT all these prompts. I've learned some things about myself. It has forced me to confront things in a way that I might not have before. I bring some some amount of skepticism to this, but I bring some amount of openness as well that I think it's telling me things that I ought to know. That's the starting point. I think the next thing is like, what do you do? So I'm going to do 2 things. Number one, I'm going to save this entire exchange and print it out and ponder it in a way that I couldn't when I was just coming at me in real time. The second thing is I'm going to ask ChatGPT, now that we've Gone through this exercise, please offer some guidance on what to actually do. Give me a specific plan for the next 90 days, the next year, and the next 3 years. Please include some stuff I should stop doing. Let's see what it says. So it's saying that I should choose one big swing, that I should ship something messy, that I should kill distractions, and that I should assemble 3 to 5 trusted readers or critics and run new material by them before it's polished. Interesting. Over the next year, I should stage something that fails. I should plant the flag on a topic that I've been exploring. I should grow a movement, not just an audience, and I should sharpen YouTube. Okay. In the next 3 years, It's giving me some things really about recasting my identity. And it's even saying that I should create a signature gathering, a live festival, annual retreat, or wisdom conference. So the bottom line, it gives me a bottom line: ruthless pruning and messy shipping. That's my 90-day plan. 1-year plan: 1 big risk and a public stake in a new project. And 3 years: a redefined identity and legacy projects in theater and thought leadership. We can use these tools. We don't have to abide by this. It's not some kind of, you know, theological force that you have to, or some kind of cult leader that you have to follow every single edict. But it does give you some things to think about, a degree of self-knowledge, and maybe a plan for your future. And one last thing. Thank you, ChatGPT. I hope we can continue the conversation. I hope so too, Dan. It says these conversations are the good stuff, the ones that sting a little but point somewhere real. I'll keep being candid, not comfortable, if you keep asking the hard questions. That's the deal. That's a good deal. Ask hard questions and accept the candor. That's a very good deal. I really want to encourage you to try a few of these prompts and see what it says. I think this is the kind of thing that the best way to work it is to do it alone. At first and think about it, and then maybe talk about your answers with somebody else. And I think there's a benefit in us sharing prompts that work, that elicit things that are meaningful, that give us direction, that actually challenge us, and then even offering up some of our answers. Because I think that one of the things that we'll see is that we have a lot in common, all of us, no matter where we are in life, that we might not be living life to its fullest. And when everybody does that, When, or at least when more people do that, everyone is better off. And this tool, again, it's not perfect, but the bang for the buck is extraordinary. And I think it's important to remember that the exercises that I've done here would not have been possible 3 years ago. And now they're literally at our fingertips. And this gives us, I think, not only guidance for ourselves, But guidance on how to use these powerful new tools to improve our lives, to elevate our lives, to surface our humanity. And this, for me, it's a call. What I'm hearing here, which I find a little disturbing, is a call to play bigger and contribute more and not hide as much as I might be hiding in ways that I didn't realize. So I hope these prompts have been useful to you. Again, try them, share them, and together, well, we'll all do better. Once again, if you like these prompts, you can get them all in one big, beautiful PDF just by clicking the link in the description. Thank you so much for watching.