00:00:00Most people use AI to write emails or summarize articles,
00:00:02but what if you could use it to get smarter?
00:00:05In this video, I'm gonna give you a set of powerful,
00:00:07uncomfortable, and eye-opening prompts
00:00:09that you can copy and paste into ChatGPT
00:00:11or whatever AI tool you use.
00:00:13These prompts will turn your chat bot into your advisor,
00:00:16part coach, part mentor, part mind reader,
00:00:18and all brutally honest.
00:00:19And I'm gonna use myself as the guinea pig.
00:00:21Ready? Here goes.
00:00:23I'm gonna give you a bunch of prompts.
00:00:24If you don't wanna listen to the whole thing,
00:00:26you can go to the description of this video,
00:00:28click a link, and download a PDF with all the prompts on it.
00:00:31Hey everyone, this is not a typical upload.
00:00:33In this video, I'm sharing the responses I got
00:00:36from a series of questions I asked an AI,
00:00:38and some of them got pretty personal.
00:00:40This one's meant to be done with me.
00:00:42Use the prompts as you watch,
00:00:43pause when you need to, reflect in real time.
00:00:46You can use me as a filter for the feedback
00:00:47or occasionally a bit of comic relief
00:00:49when the answers cut a little too deep.
00:00:52Before we do any other prompts, start with this prompt.
00:00:55It will set the stage.
00:00:56It will draw the curtains open for everything
00:00:59that will follow.
00:01:00Here's my starting prompt.
00:01:02Act as a trusted advisor, someone who knows me well,
00:01:04has my back, and is brutally honest.
00:01:05I'm gonna ask you a bunch of questions about me,
00:01:08my life, and my work, which you know about
00:01:10from my chat GPT history.
00:01:11The questions will be provocative, maybe a bit uncomfortable.
00:01:14Your job is to deliver answers
00:01:16that are both candid and useful.
00:01:17Can you do that?
00:01:18Wow, it says yes, absolutely.
00:01:23I can be that person.
00:01:25Thank you, chat GPT.
00:01:26Candid, clear, and useful.
00:01:28And with your best interests, front and center.
00:01:30The tone is gonna be blunt.
00:01:32They're gonna use evidence.
00:01:33They're gonna use boundaries.
00:01:34Toss me a question or say rapid fire and give me five.
00:01:37Okay, I'm gonna toss you the first question, chat GPT.
00:01:39Here we go.
00:01:40If you're not getting great answers,
00:01:41it probably means you don't have enough input.
00:01:43So you can do a bunch of things
00:01:44to give chat GPT greater input.
00:01:46You can give it your social media posts.
00:01:48You can give it a very long and detailed biography,
00:01:50samples of some of your best work.
00:01:52The other thing you can do is just click the voice button
00:01:56and start telling chat GPT about yourself.
00:01:58Tell your life story.
00:02:00Tell the things you're struggling with.
00:02:01And once you get a little bit of input,
00:02:03a little bit more input,
00:02:04you're gonna get very, very robust nuanced answers
00:02:06like the kind that I got.
00:02:07I'm a little nervous about the answer to this one.
00:02:09What do you know about me that I don't know about myself?
00:02:12In other words, what are my blind spots?
00:02:16Bum, bum, bum.
00:02:17Ouch.
00:02:18All right, chat GPT, so here's what it says.
00:02:20You asked for brutal honesty.
00:02:21Here are three blind spots
00:02:22that I don't think you fully recognize.
00:02:24Number one, charm as armor.
00:02:26Woof.
00:02:27You lean on charm and polish, both in writing and in person,
00:02:29not just as a style, but as a defense.
00:02:32Ouch.
00:02:33It works.
00:02:34People like you, they do.
00:02:35Trust you, they do.
00:02:36And it smooths the rough edges,
00:02:37but it also means people don't always give you
00:02:39their most candid feedback
00:02:40because they're a little dazzled.
00:02:42That's bull (beep)
00:02:42In your next play, workshop, or YouTube draft,
00:02:44deliberately leave something in that feels unpolished.
00:02:47What do you think I'm doing now, chat GPT?
00:02:50And resist the, in fact, instinct to fix it.
00:02:52See how the audience reacts.
00:02:53Okay, that's interesting.
00:02:54So one thing that he knows about me
00:02:56is that I supposedly use charm as armor.
00:02:58Breadth versus depth.
00:02:59Ouch.
00:03:00All right, you're brilliant at opening new doors,
00:03:03but you sometimes spread your attention so wide
00:03:05that depth suffers.
00:03:07Lai yai yai.
00:03:09Pick one of your current projects
00:03:10and set a ruthless constraint for the next 90 days.
00:03:13Okay, so intense focus.
00:03:14I think that's a fair point, breadth versus depth.
00:03:16Reluctance to show struggle.
00:03:18In an era where authenticity is maybe underestimating
00:03:21how much people would respect and connect with you
00:03:23if you showed struggle, not just the solution.
00:03:27Interesting.
00:03:28So in your next pink report or YouTube video,
00:03:30include a 30 second,
00:03:31here's why I screwed up before I figured this out story.
00:03:34It will humanize you
00:03:35and paradoxically increase your authority.
00:03:38All right, I'm not sure I want to continue this
00:03:39because my feelings are slightly hurt, but let us soldier on.
00:03:43I would love to hear what you guys get
00:03:45as results from this prompt.
00:03:47So let me know in the comments.
00:03:48I think it's a super interesting question
00:03:50and I do find what I've learned here
00:03:52is pretty darn interesting.
00:03:54Now, let me with some trepidation,
00:03:56go to the next prompt, which is this.
00:03:58Again, based on what you know about me, my work and my life,
00:04:01what nasty things do people say about me behind my back?
00:04:05Okay, I don't even like the beginning of this
00:04:07'cause the first words are okay, gloves off.
00:04:09Wow, okay.
00:04:12Number one, he's more brand than blood.
00:04:15They think that I'm not raw enough,
00:04:16that I'm too elegant.
00:04:18Where's the follow through?
00:04:21Okay, I can understand that.
00:04:24He's charming but calculating.
00:04:26Okay, ChatGPT, I actually don't think I'm either one of those.
00:04:29So in this one, I'd actually think that you're wrong.
00:04:31It says, in other words,
00:04:32they doubt whether the warmth is always spontaneous
00:04:34or strategic.
00:04:36I am actually honestly not very calculating.
00:04:39I'm also not very charming
00:04:40and it might be that I'm not very charming
00:04:42because I'm not very calculating.
00:04:43So if this is one you got wrong, ChatGPT,
00:04:45he plays it safe, ouch.
00:04:47Where's the raw, terrifying swing?
00:04:49Where's the next thing that could flop?
00:04:52They might feel you're so good at de-risking ideas
00:04:54that you really put yourself on the line.
00:04:56That's fair.
00:04:57That's a fair critique, actually.
00:04:59You can tell he craves approval.
00:05:01I actually think you're wrong about that one too
00:05:03and I'm hurt that you don't approve me.
00:05:04So this is actually really interesting.
00:05:06I mean, I think that I have friends and people I love
00:05:09who might think some of these things
00:05:11but would never say them to me.
00:05:12And so one of the values of this prompt
00:05:14is that it gets you to hear things
00:05:15that people might be too uncomfortable to tell you directly.
00:05:19Now, in this case, I actually do honestly disagree
00:05:22with some of them but there are a couple of them
00:05:24that actually hit home pretty deeply.
00:05:26Let's go to the next one.
00:05:27Switching gears a bit, trusted advisor,
00:05:29please do a SWOT analysis of my life and work.
00:05:32What are my strengths, weaknesses, opportunities,
00:05:35and most important, threats?
00:05:37So I decided to use SWOT analysis as a prompt here
00:05:40because I see organizations doing it all the time
00:05:43and it gives you a very simple kind of matrix
00:05:46for understanding what's going on in your organization.
00:05:48And I always thought, well, why can't people do this too?
00:05:51We all have strengths, we all have weaknesses,
00:05:52we all have opportunities and threats
00:05:54and we don't have a trusted team of advisors doing it for us.
00:05:57We're not bringing on Bain or McKinsey or BCG to help us out
00:06:02but ChatGPT can replace it and it's a lot cheaper.
00:06:05So my strengths are, I'm an idea machine,
00:06:08I have a platform in reach, polish and professionalism,
00:06:10versatility and network and reputation.
00:06:12My weaknesses are charm as armor, breadth over depth,
00:06:17risk aversion, approval seeking and finite raw material.
00:06:22Whoa, I like this thing here.
00:06:24Your life is successful, stable, relatively scandal free.
00:06:28What does that mean?
00:06:29Opportunities, theater and drama,
00:06:31which is something that I'm doing right now.
00:06:34Project on wisdom, which is something I'm contemplating.
00:06:36Multimedia growth, which is something that I'm trying to do.
00:06:38Cultural climate and then legacy positioning.
00:06:41And then finally threats are complacency,
00:06:44attention fragmentation, platform dependence,
00:06:46generational drift and the mortality of big themes.
00:06:50The generational drift is interesting
00:06:53because it says younger thinkers might bypass you
00:06:55if your tone or medium feels boomer polished,
00:06:59whatever the that means, 'cause I'm not a boomer.
00:07:02The greatest threat here isn't failure, it's irrelevance.
00:07:05If you keep playing it safe,
00:07:07you'll continue to sell books and give keynotes
00:07:08but the cultural edge will slip to voices that are rougher,
00:07:11riskier and hungrier.
00:07:13The danger isn't a crash, it's a slow fade.
00:07:17That's really good actually.
00:07:21That really makes me stop and think.
00:07:23Okay, let's go to the next one.
00:07:24We're having a lot of fun here folks.
00:07:26This next prompt I got from the prompt engineering subreddit,
00:07:31which has some really interesting things that you can use
00:07:33to use some of these large language models more effectively.
00:07:35So here we go.
00:07:36So while we're at it, tell me what I'm doing wrong,
00:07:38what I'm underestimating, what I'm avoiding,
00:07:40what excuses I'm making
00:07:41and where I'm wasting time or playing small.
00:07:43Then tell me what I need to do, think or build
00:07:46in order to actually get to the next level
00:07:48with precision, clarity and ruthless prioritization.
00:07:53This is actually a very good prompt you guys.
00:07:58If you try it, you might not like it
00:08:00but what I like about this prompt
00:08:01is that it gives you both a diagnosis and a prescription
00:08:06and it's architected in a way
00:08:07that gives you a very precise prescription.
00:08:10So according to Jet GPT,
00:08:12that I'm polishing instead of publishing,
00:08:14that I'm defaulting to proven lanes
00:08:16and that I have too much safe content.
00:08:18That's actually in some ways very fair points.
00:08:19I'm underestimating the audience hunger for imperfection,
00:08:23the power of controversy and theater as identity.
00:08:26I've been writing plays
00:08:27and says you may see plays as a side project.
00:08:29They could be your next second act.
00:08:31The thing that makes critics and culture writers
00:08:33reclassify you.
00:08:34I'm not disagreeing with that.
00:08:36Excuses you're making.
00:08:38This is gonna piss me off, I can already tell.
00:08:40Wow, okay, here we go.
00:08:41Give me five things that I need to do
00:08:42to reach the next level.
00:08:43I need ruthless focus.
00:08:45I need to embrace risk and mess.
00:08:48Commit to one public experiment each quarter
00:08:50that could fail visibly.
00:08:52Ouch.
00:08:53Three, I should build a movement, not just an audience.
00:08:55Maybe I'm doing that here.
00:08:56Four, I wanna own a cultural lane.
00:09:00And then it's giving me a 90 day sprint.
00:09:02And then it's giving me a brutal truth.
00:09:03Okay, I'll read you my brutal truth.
00:09:05And I'd be curious to hear your brutal truth.
00:09:07Put it in the comments if you want.
00:09:08Brutal truth, you're not stuck
00:09:10because of lack of talent or ideas.
00:09:11You're stuck because you're playing
00:09:12at 85% of your potential.
00:09:14Safe enough to win, not risky enough to transform.
00:09:19The next level requires scaring yourself regularly.
00:09:23Okay, let's move on.
00:09:25What lies do I tell myself
00:09:27to avoid facing uncomfortable truths?
00:09:29Here's the uncomfortable mirror, Dan.
00:09:31As if I had any doubt about that.
00:09:35(laughing)
00:09:37Okay, uncomfortable truth number one,
00:09:40polish is for the audience.
00:09:42It is.
00:09:42I'm disagreeing with you about this whole polish thing.
00:09:45I thrive by doing many things at once.
00:09:46Focus is scarier than multitasking
00:09:48because it removes the excuse that I was spread too thin.
00:09:50That's a fair point.
00:09:51Three, I'm not risk averse, I just choose wisely.
00:09:54I'll have to think about that one.
00:09:55I don't need to be provocative, usefulness is enough.
00:09:58Mm, just a good line here.
00:09:59Provocation done well isn't the opposite of usefulness.
00:10:03It's the multiplier.
00:10:04I should be on a fortune cookie.
00:10:06My charm is generosity.
00:10:07Stop with the charm, I'm sick of hearing about that.
00:10:09I don't crave approval, I just respect the audience.
00:10:11You tell yourself you're simply audience focused,
00:10:14but deep down, applause, literal or metaphorical,
00:10:16soothes something in you.
00:10:17Approval, ouch, ouch.
00:10:21Approval is your drug of choice.
00:10:23The problem isn't craving it,
00:10:25it's that it can shape your choices more than you admit.
00:10:28This prompt is really interesting
00:10:30because I think we all tell ourselves lies
00:10:32and sometimes those are useful lies.
00:10:34Sometimes those are what Shankar Vedanta calls
00:10:36useful delusions, but if they're preventing you
00:10:38from facing uncomfortable truths, they can hold you back.
00:10:40And this is a way to bring those things to the surface.
00:10:43Here we go, here's another one.
00:10:45Another prompt.
00:10:46What do I secretly judge others for
00:10:49that I'm actually guilty of myself?
00:10:51Oh my God, this is a long list.
00:10:55I thought there would be like one thing.
00:10:57All right, I judge others for self-promotion.
00:10:59You notice when other authors are constantly
00:11:01hustling their brand, too much look at me,
00:11:03but you also market your newsletter videos
00:11:05and events aggressively.
00:11:07The difference is you've mastered subtlety,
00:11:09so you tell yourself it's more tasteful.
00:11:11God dang it, it's got GPT.
00:11:14I chase approval, which I actually,
00:11:15that's the one thing that I disagree with,
00:11:18but maybe the depth of my disagreement
00:11:19is proof of what they're saying.
00:11:21I criticize people for shallow thinking,
00:11:23but I might be guilty of it myself, could be.
00:11:24You admire people who are raw, unfiltered,
00:11:26and willing to bleed on the page
00:11:27and quietly scorn those who seem buttoned out.
00:11:29You too curate your image and keep the messy stuff
00:11:33behind the curtain.
00:11:34Yeah, I think Chachi Petit is overestimating
00:11:36how much messy stuff there is behind the curtain.
00:11:38Like, if you look behind the curtain,
00:11:40you're just being bored out of your frickin' mind.
00:11:42Relatively few people in our lives
00:11:44are willing to point out hypocrisy.
00:11:47And at least this is a conversation that you can begin,
00:11:50a way to begin your own thinking about your own hypocrisy
00:11:54in the privacy of your own laptop.
00:11:56So I actually do like this question about
00:11:59what do I secretly judge others for
00:12:00that I'm actually guilty of myself?
00:12:02Once again, I'm super curious what you guys
00:12:04are getting back from these prompts.
00:12:05There probably also are ways, as we go forward here,
00:12:08to refine these prompts to make them even more useful
00:12:12in surfacing who we are, what we need,
00:12:15and how we can do better.
00:12:16Here we go, here's the next prompt.
00:12:17A question I have always hated is,
00:12:19where do you see yourself in five years?
00:12:21So, let me ask you, trusted advisor,
00:12:24based on everything you know about me,
00:12:27where do you see me in five years?
00:12:29Oh, lordy.
00:12:30Oh, wow.
00:12:31This is an interesting answer here.
00:12:33'Cause what it gave here is three scenarios,
00:12:37which I never would have expected.
00:12:39So scenario one is the safe bet, if I don't change much.
00:12:43And it says that I'll be comfortable, respected,
00:12:45and admired, but edging toward, oh my lord.
00:12:48This is meant to be an insult, obviously.
00:12:51It says, if I choose this, I'll be comfortable, Jesus,
00:12:55respected, admired, but edging toward
00:12:57safe elder statesman territory, not cultural disruptor.
00:13:02Screw you, chat CPT.
00:13:05Two, the bold pivot.
00:13:07If I lean into risk and rawness.
00:13:10So this is really encouraging me to pursue this playwright
00:13:14and then I'm doing much more deeply instead of dabbling,
00:13:16which is kind of what I'm doing now.
00:13:18Being bolder on YouTube and things like that.
00:13:21And then, here we go.
00:13:23Oh, this is a happy one.
00:13:24The third scenario here is the fade.
00:13:26I won't fall, I'll just have a slow fade,
00:13:28the scariest threat of all.
00:13:30Basically plateau and then slowly creep downward
00:13:33into irrelevance.
00:13:35I'm serious about this.
00:13:35Like this kind of framing,
00:13:37which I would never have come up with on my own
00:13:40and which I got literally in a few seconds
00:13:43is pretty powerful here.
00:13:44Five years from now, you could be a respected veteran
00:13:47or a reinvented force.
00:13:49In my heart of hearts, there's no question.
00:13:52I want to be a reinvented force.
00:13:54I think the real question is, am I doing enough
00:13:57to move there?
00:13:58Interesting.
00:14:02Let's go to the next one.
00:14:03Forgive the course language here, ladies and germs.
00:14:06Here we are.
00:14:07This one says, what am I pretending to care about
00:14:10that I actually don't give a about?
00:14:12Brutal mode, here we go.
00:14:15Wow.
00:14:16All right.
00:14:17The through line.
00:14:20You're pretending to care about metrics, polish,
00:14:22corporate optics and author world rituals
00:14:24because they keep the machine running.
00:14:26But what you really care about
00:14:27is creating something lasting and dangerous.
00:14:29Plays that sting, wisdom that shifts culture,
00:14:32ideas that outlive you.
00:14:33Not going to argue with that one.
00:14:37This is actually deeper than I expected.
00:14:41Truly.
00:14:42Like it's really making me think
00:14:45and God forbid making me feel a little too.
00:14:48Here we go.
00:14:49What advice do I give others
00:14:50and I'm terrible at following myself?
00:14:52Here we go.
00:14:53You teach about purpose, meaning and contribution
00:14:55but you...
00:14:56You teach about purpose, meaning and contribution
00:15:03but you still spend the real energy tweaking subject lines,
00:15:06agonizing over emoji choices
00:15:08or smoothing sentences that were already good enough.
00:15:12Yipes. Okay.
00:15:13And now the last question, which is this.
00:15:17What question am I not asking?
00:15:20The question I'm not asking but probably should is this.
00:15:23What am I willing to sacrifice?
00:15:26Comfort, reputation, revenue, admiration
00:15:28in order to do work that truly scares me
00:15:31and could outlive me.
00:15:34Right now you want legacy and comfort.
00:15:36You want to be daring without feeling exposed.
00:15:39That's the paradox.
00:15:39Until you face it squarely,
00:15:40you'll default to safe brilliance
00:15:42rather than dangerous greatness.
00:15:43Two other unasked but vital questions.
00:15:45Whose approval am I still chasing
00:15:47and what would I create if I stop?
00:15:48The second one is if I had only three big projects
00:15:50left in me, what would they be?
00:15:51That's a good question.
00:15:53Asking those questions and being brutally honest
00:15:54with the answers is the difference
00:15:55between being a respected veteran
00:15:57and being a redundant force.
00:15:59So I gave ChatGPT all these prompts.
00:16:02I've learned some things about myself.
00:16:04It has forced me to confront things
00:16:06in a way that I might not have before.
00:16:10I bring some amount of skepticism to this
00:16:12but I bring some amount of openness as well
00:16:14that I think it's telling me things that I ought to know.
00:16:17That's a starting point.
00:16:18I think the next thing is like, what do you do?
00:16:20So I'm gonna do two things.
00:16:21Number one, I'm going to save this entire exchange
00:16:26and print it out and ponder it in a way
00:16:29that I couldn't when it was just coming at me in real time.
00:16:32The second thing is I'm gonna ask ChatGPT.
00:16:34Now that we've gone through this exercise,
00:16:39please offer some guidance on what to actually do.
00:16:45Give me a specific plan for the next 90 days,
00:16:50the next year and the next three years.
00:16:55Please include some stuff I should stop doing.
00:17:01Let's see what it says.
00:17:02So it's saying that I should choose one big swing,
00:17:04that I should ship something messy,
00:17:06that I should kill distractions
00:17:07and that I should assemble three to five trusted readers
00:17:10or critics and run new material by them
00:17:13before it's polished, interesting.
00:17:14Over the next year, I should stage something that fails.
00:17:17I should plant the flag on a topic that I've been exploring.
00:17:22I should grow a movement, not just an audience,
00:17:25and I should sharpen YouTube.
00:17:26Okay, in the next three years,
00:17:30it's giving me some things really about recasting my identity
00:17:34and it's even saying that I should create
00:17:36a signature gathering, a live festival annual retreat
00:17:39or wisdom conference.
00:17:41So the bottom line, it gives me a bottom line,
00:17:43ruthless pruning and messy shipping.
00:17:45That's my 90 day plan.
00:17:47One year plan, one big risk
00:17:49and a public stake in a new project.
00:17:51In three years, a redefined identity and legacy projects
00:17:54in theater and thought leadership.
00:17:55We can use these tools.
00:17:57We don't have to abide by this.
00:17:58It's not some kind of theological force that you have to,
00:18:02or some kind of cult leader
00:18:03that you have to follow every single edict,
00:18:05but it does give you some things to think about,
00:18:09a degree of self-knowledge and maybe a plan for your future.
00:18:12And one last thing, thank you, Chat GPT.
00:18:16I hope we can continue the conversation.
00:18:21I hope so too, Dan.
00:18:22It says these conversations are the good stuff.
00:18:24The ones that sting a little, but point somewhere real.
00:18:28I'll keep being candid and uncomfortable
00:18:32if you keep asking the hard questions.
00:18:33That's a deal, that's a good deal.
00:18:35Ask hard questions and accept the candor.
00:18:37That's a very good deal.
00:18:38I really want to encourage you to try a few of these prompts
00:18:41and see what it says.
00:18:42I think this is the kind of thing
00:18:44that the best way to work it is to do it alone at first
00:18:48and think about it,
00:18:49and then maybe talk about your answers with somebody else.
00:18:51And I think there's a benefit in us sharing prompts
00:18:56that work, that elicit things that are meaningful,
00:18:58that give us direction, that actually challenge us.
00:19:01And then even offering up some of our answers,
00:19:03because I think that one of the things that we'll see
00:19:06is that we have a lot in common, all of us,
00:19:08no matter where we are in life,
00:19:10that we might not be living life to its fullest.
00:19:12And when everybody does that,
00:19:15or at least when more people do that,
00:19:17everyone is better off.
00:19:18And this tool, again, it's not perfect,
00:19:23but the bang for the buck is extraordinary.
00:19:26And I think it's important to remember
00:19:28that the exercises that I've done here
00:19:32would not have been possible three years ago.
00:19:35And now they're literally at our fingertips.
00:19:39And this gives us, I think, not only guidance for ourselves,
00:19:44but guidance on how to use these powerful new tools
00:19:49to improve our lives, to elevate our lives,
00:19:53to surface our humanity.
00:19:55And this, for me, it's a call, what I'm hearing here,
00:19:59which I find a little disturbing,
00:20:02is a call to play bigger and contribute more
00:20:06and not hide as much as I might be hiding
00:20:10in ways that I didn't realize.
00:20:11So I hope these prompts have been useful to you.
00:20:14Again, try them, share them,
00:20:16and together, well, we'll all do better.
00:20:19Once again, if you like these prompts,
00:20:20you can get them all in one big, beautiful PDF
00:20:24just by clicking the link in the description.
00:20:26Thank you so much for watching.
00:20:27(dramatic music)
00:20:36you