Writing Advice You Should Avoid | Nat Eliason

The number one reason people drop books is there's nothing keeping them turning the next page in my first two paragraphs I'm getting thrown out of bed in the middle of the night my baby is crying and I'm about to lose $100 million what if I really want to Captivate readers I need to learn how to tell great stories people hire so much editing help I think it's a big mistake what it's doing is it's removing your Style totally it's the grammarly problem let's do a fire around okay you have this checklist for telling good stories

this idea of Promise progress and payoff huge game changer love that once you hear this you're never going to be able to unhear it and you're going to notice it in everything you read and everything you watch which is so you want to become a better writer huh well where should you start what's one thing you can do become a better Storyteller now I know I know I know before you make fun of me I know you've heard that advice before but this episode is different and I hear you my eye rolls too because everybody

says you got to tell better stories and storytelling advice is always so meh but this episode Nails it because natal really studied storytelling as he wrote his book crypto confidential so what's his background he started as a non-fiction blogger who was Focused on SEO and these super tactical articles but eventually he said no I'm tired of this it's not for me anymore I'm Gonna Change Tack and I'm gonna write a memoir and I'm gonna make it a gripping page Turner of a memoir but uh-oh I have the vision but I definitely don't have the skills

to pull it off maybe you're feeling that way and if you are I want to help you so come join my writing program it's called right of passage now back to Nat his realization Put him to work he basically went to a cave for two years where he learned all about the craft of Storytelling and this episode is about the tactics that he picked up as he was trying to create his own MFA questions like how do you grip readers how do you keep them Eng what is the right way to Pace a story and

then how do you have a resolution at the end that moves people to share your work so now let's talk writing with natal so tell me about the people who You're pulling inspiration from you're talk about the morning reads that you do and I know that David Foster Wallace really influenced you so let's start there this to me has actually been one of the most helpful ways to get better at writing which is one fig one you kind of have to develop a certain level of taste right you have to have read not just a

lot of books but a wide variety of books and King talks about this a lot where he Says that you need to read bad books too because re well like bad right so maybe you call that commercial or something uh where they're not actually bad but they maybe don't have that beautiful Pros or that incredible detail and imagery of a Steinbeck or a Wallace or something and the value of reading books that you think aren't good is that you then have to articulate okay what's not good about this right what don't I like here and

once you can do that you can then look At other books and say oh he does or she does this thing really really well and I really really like that so for me my first challenge with going from writing basically how-to articles to writing narrative non-fiction was that I didn't know how to tell an exciting story that wasn't a skill that I had and that was the first big piece of feedback I got when I gave draft chapters yeah it was I'm bored I'm confused I'm like great those are like the two best things you

Hear that that exactly that's exactly what's going to get your book recommended right uh and so I said okay I need to learn how to do that and I read a bunch of books on writing better but I also said okay I need to find examples that pull me into that writing style so that I can prime myself with it before I go write and one that was actually really helpful was Red Rising and it's it's super fast-paced Super engaging very hard to put down it was everything that my writing wasn't and it was extremely

commercially successful right it's one thing to read beautiful literature that has this incredible Pros that people at you know ivy league Masters stuck in an MF program and it's like okay yes this is great writing but if most people don't like it you know how how good is it actually if it doesn't get out there so my question was can I take kind of a red Rising energy and bring it to a narrative non-fiction Finance book and that was kind of that part of the practice was I would wake up and read a book like

that I wouldn't read like a Michael Lewis book I would read you know exciting fiction to get in that head space and then I could bring some of that energy to my writing later in the day one of the analogies here is in the world of film there's a different kind of movie that you see in a theater Versus like a film festival or like a Vimeo right when you go on Vimeo staff picks or at a film festival it's sort of like movies made for people who make movies yes which is very different from

normies like me who are like hey it's Saturday night I'm going to go to the movies totally and it's so true with writing too where one one of the big things I realized is that there's a limit to how much you can let this idea get into your brain but a lot of the Problems that I see as problems in my writing or other writing nobody else notices right and they're not even problems they're like ways to improve so you know I would I might look at a draft of a chapter of mine and you

know I'm I'm seeing all the problems with it I'm seeing all the problems and in the beginning that's great right because there were there were tons of problems right and like they did need to get improved but no matter how good it gets I will still always look at it and just see the problems right it's impossible for me to look at it as somebody who's chilling in bed who just wants a fun story and does not care that the description of this scene is a little thin and it could be rounded out more without

like interrupting the dialogue whatever right like that never crosses their mind it does if they're really into books but for 98% of readers they're not going to think about it and So there is this it's kind of like the perfectionism problem right you have to also figure out at what point you're reading as a writer versus reading as a reader and remember that 99.9% of people who ever read your stuff are reading as readers so as you were writing crypto confidential pulling from David Foster wellis the thing that really stuck out was the way that

you wrote about emotions like you never used to write like that and I was saying this To you in the elevator like you are like a new writer at this point there was like oldn and then there's newn and oldn was very much how to direct to the point really good at simplifying things distilling and it's like hey great Nat just figured out a problem I'm going to read the article and I'm going to do exactly what just said right and then there were all these phases of that sort of right there was food and

then there was Rome n like all these sorts of Things and then you basically became a Hermit for two years and then you came back and now you're writing these stories it's like a memoir it's like thrilling and captivating but the thing that stuck out the most was you writing about emotions what did you take from David Foster walles in terms of writing about emotions and how did you think about doing that the thing that I think makes uh Wallace's writing so powerful Especially in his fiction is that it's very clear at parts that it's

not fiction he's describing some of these experiences like being in a really really desperate state for drugs and waiting for the dealer to arrive and the Mania that comes with it and it's so painful to read and so powerful that I mean it could just be that he's the best writer ever or it's like you've clearly experienced this in some degree and when he writes about suicide too you really Get that feeling that you are putting your feelings on the page and you are not holding back at all like that burning building burning building right

it's so clear that he's describing what it feels like to be on the brink of suicide in a way that you I've never seen anywhere else right and really what makes that writing so powerful is the honesty because I think that and you hear this all the time but it's very hard to take action on which is we're All walking around these kind of bundles of anxieties and fears and unspoken thoughts and everybody to some extent is wondering if they're broken or if they're screwed up or if they're the only one who feels these things

and part of your job as a writer is to tell people you're not the only one like that's okay the more you're willing to be honest about your emotional experience the more your work is going to connect with people and there's a Natural tendency to pull it back because like you know if if a if a book does well right millions of people might read it and they're going to know that you feel these things like they're going to see that oh you are broken right like there is something wrong with you and you know

that's a terrifying thought but you're also doing this service by doing that and so that was you know there there were a few scenes in there that I mean like I literally Can't go read them anymore right like it's just really hard and I'm dreading doing the audiobook because I still have to do that and that's G to be a challenge but I knew that if I did them right it would add this sort of emotional tenor to the book that would make it so much more real and so much more connective with you know

people who saw other people go through similar challenging experiences that all broadly lump under like gambling addiction and The people who actually went through some version of that and hold some like deep regret over who they were with their friends or their partner their families or whatnot and I think that's like one of the most important things you can do if you're just writing like light fun happy bouncy like win-win-win all the time then it's still fun and interesting but it doesn't create that bond with the reader um and so that was I mean that

was really one of the like Main things I wanted to do was try to learn how to get that across and I knew I was getting there at one point because I was writing in a coffee shop and I just started like sobbing like in the middle of the coffee shop I just like pack up my laptop and like run to the car and get out of there I was like I yeah and it came out of nowhere and I was like okay I I can't be here while I finish this uh and that learning

how to do that Itself and I still don't think I'm that good at it but I got a lot closer to what I would consider good as I went are you comfortable going down this Rabbit Hole I think it'll be a little heavier um but I think it'll be I think it'll be really really real about the writing experience I remember I went through a tough breakup and I ended up writing like 15,000 words in two weeks and I didn't share it or anything but I remember just sitting at my desk and Just like crying

and crying and crying and the more I wrote about it like the more that it just the emotions just poured out of me and it was it was so it was so hard to just realize that I was having emotions like that um and even now like I tried to read one of the paragraphs to a friend and just like you I was like I I I like I can't go do it it's like we're we're going to lock this one in the Shelf yeah or I don't know maybe that means that's What you should

yeah it could be the best thing you ever publish right there's a chance that's there too right like yeah and and and I think that what's revealing is the thought of publishing that is just haunting to me yeah haunting yeah super scary I mean in some ways I feel very lucky to have worked with a publisher because I think if I had tried to self-publish this I might have just shelv it by the time I got to that point there would have been This feeling of okay no this can't I can't I can't publish this

or I would have toned it down but having somebody who you could show it to who's like trying to get it across the Finish Line with you and for them to say no this is great stuff you have to do this and not only that but you have to go deeper on it I think was kind of the little nudge I needed to get it there is there a specific story or specific conversation where someone said I I want you to go Deeper and how'd you do that so we have a mutual friend Nathan B

and he he read an earlier few chapters of the book and he said he was like you know he said the the action and the story is All really fascinating but it feels like I'm missing some of what's going on in your head right I'm missing some of the interiority how are you feeling reacting to these things and in my head I'm going nobody cares what I'm thinking right they just want the fun action stuff and Also like I don't want to share what I'm thinking because that would be pretty vulnerable but I took that

feedback and then I went and I workshopped some parts and just added a little bit more and it doesn't take much that's one of the things you really learn with doing editing around I guess emotions especially is that you can do a lot with one sentence in the right place right it can really pull a lot out and I I started adding a Couple of those and it just made some of the scenes a lot more powerful and that made me realize that there is you know one this real value to being clear that this

wasn't just a a quick thing that happened that it wasn't a quick decision it was like I was actually torn up about this right there's one scene in the book where we're I'm working with this this team and they're debating whether to launch their token or not you know do we launch it do we not launch it and Because there was there was some minor risk that something could go wrong with the launch and if something went wrong with the launch people could lose a bunch of money and so they messaged one of their like

colleagues in the crypto space and this guy was you know hilarious degenerate Gambler super AG like total stereotype crypto investor I messaged him and he sends back this message and I I have the I have the message in the book quoted for B but It's something like something like this is crypto happens all the time people lose money that's how you get the big wins quit being a and just ship it nice guy yeah that that's what he sent them and they posted it in the chat and they were like well this is what he

thinks and in the original in the original version I just said like okay well what do you want to do right but a lot of people said that and they're like how could That be your response to somebody saying this and on the one hand I knew this guy I knew that this is almost like a character he's playing right and like he doesn't actually mean it quite that savagely but also that is just a pretty Savage opinion and there was a lot of real like there about like what the hell do we do because

on the one hand he's right it is crypto stuff does break all the time people who are playing at that level Know that anything they're putting money into it might just disappear tomorrow right this isn't stuff that's like going on coinbase it's super safe and vetted it's the the crazy risky degenerate Casino side of it so he's right but it's also kind of a up mentality to have right like to be that flippant about people losing money totally and so it was this tense situation and so adding a few sentences there drawing it out and

saying like Okay no you know Here was the conflict in my mind did actually make it feel more alive um because it those kinds of uh debates did come up pretty often in that world yeah how did you think about as you were going through the revisions trying to get that emotional aliveness how like one thing that I struggle with and I see all the time is people are doing revisions and they actually lose their voice m M mhm because the writing becomes Stultified people are just trying to be perfect and I think it takes

both a very talented editor and a good writer to revise your way into more of yourself yeah well I think of this as the grammarly problem huh where that's great a lot of good writing is in the grammarly advice you ignore totally because if you that if you run your piece through grammarly it'll say oh you're being you're being too longwinded here this should be briefer you you Shouldn't you should use this contraction instead of the full word you should use this more complicated or simpler word instead of this word but what it's doing is

it's removing your style right and it's pushing you towards some vague sense of the right way to write it's funny that you say that because I bet that grammarly would rate your book way worse than your internet writing but I think your internet writing is is not as good as the book Like even just how many I guess you would call it like compound sentences commas like you're messing around with different sentence structures you're not trying to be like simple simple simple short you know well yeah and there there's a couple chapters in here that

have sections where there are no dialogue tags no setting tags nothing to give you any sense of what's going on in the scene except for just random pieces of dialogue and that was a very Deliberate stylistic choice to try to get the reader very stressed out because I wanted to find a way to make people feel the manness angst and like what the hell is going on here feeling that we were feeling going through that and so deliberately writing in this broken like wrong way helped create some of that energy in the reader but you

put that into any you put that into Claud you put that into gramly and they'll be like what the hell is going on here like this Is bad writing but I think it's great in that it does that job and so that's going back to like developing taste right you have to learn when the tools when readers not are giving you bad advice and when it's good and like you said a great editor knows how to bring out more of your voice and not try to apply unnecessary rules to it to try to make you

conform to some like normal style I I actually have this opinion too that I think it's a big mistake that a Lot of people hire so much editing help in their book process and I know a lot of our friends would disagree with me on this but I feel like the more Cooks you bring to the kitchen the more you lose your style and where you lose what makes like you interesting and great and you totally can especially for non-fiction you totally can formulaically architect a non-fiction bestseller and you can find the editors and the

marketing team or whatever to make that happen but it Sort of won't be your book at the end of it because you'll have brought in all of this like outside structure to make it happen it's like uh the way that private Equity builds companies oh say more well you have have we're going to think of it we're going to look at the spreadsheet we're then going to take it we're we need this profit margin we need this sort of growth rate and if you think about when private Equity buys a company it is so not

what a Founder would do in Their company founder driven companies are sort of strange Founders are sort of crazy they're just all over the place they're making these rash decisions but you're kind of in these founder-led companies you're like why do you do things that way and it's because because the founder wanted to do that but you don't see that kind of distinctiveness in a private Equity company and those companies might make a lot more money exactly that's some of that artistic Feeling so you kind of have to decide which one you want the analogy

that I I think of a lot is pop music because a lot of pop music is engineered to some degree right it's it's designed they know it's going to do well and so the artist has this voice and they work with that voice but they also know how they can kind of like design it to do really well on the charts and then you have artists who just want to do their thing and if it does well great if it doesn't Do well that's okay too because we know we did our thing and they don't

care as much about those metrics and so this was a big discussion with the cover right so can I show the cover I won't be too selfpromo here but this was a big argument about the cover because this is not a non-fiction book cover huh it you know non-fiction has rules for how you do the cover you have big block text you have an easyto read subtitle you have a little Stinger that goes at like the Very top or the very bottom you have uh you know simpler maybe like geometric or whatnot design to it

and they they initially came back with covers that looked like that and me and my editor both said no this this absolutely is not what we can do here and the thing that I kept saying was it needs to the cover needs to feel like you're strung out on caffeine and nicotine and like scrawling this in between you know trades or something it Needs to have that um Fear and Loathing in Las Vegas feel to it that was the main inspiration is I sent them that and I said this is like what we want to

use as inspiration for the cover like how do we get not just to cover with the whole book to this and so it like we designed all the chapter headers in that feel the in between chapters with that feel we wanted it to like be this whole fun production but that also breaks like all of the rules for how you're supposed to Do non-fiction Mass Market but to me I kind of felt like this is what this is how we should do it to create like the piece of art that I want to make here

I want to point at some really interesting tensions that are emerging which is on one hand you wanted to create a work of art and you're like yo why aren't books art anymore they used to be this like expression of who I am but then you also wanted something that was commercially viable and then also you wanted a sense Of individuality and distinctiveness but then there were many different places where you said all right what are other people doing who have been successful and how can I learn from them and I find the Paradox is

there to just be fascinating the the tension is real and I think it's really important to know how to walk that line it's a really useful skill to develop so that you can you know do something that resonates with you and that still pays your bills Right a good example this is the title because the original title that I had which I still really like is is everyone getting rich without me right which is a fun title but it doesn't explain that it's crypto and I liked it my agent liked it my editor liked it

and then we were getting on the fourth draft or something and we sent some early pages to the sales team and it is something I think a lot of people outside publishing don't know Is that the sales team also reads early versions of the book and they give feedback on little tweaks you could make to make it easier for them to go sell the book and this has to do with framing yes okay framing packaging marketing because they're they're going to they're going to give a catalog to book buyers and whatnot of all the books

that are coming out but they're also going to talk to book buyers and they're going to say oh you know we've got like this Really cool book coming out oh cool what's it about well it's about this and they need to be able to very clearly explain what it's about and they said that is everyone getting rich without me be too many things it could be GameStop call options right it could be buying airbnbs it it could be crypto right it could be a bunch of things it wasn't clear what people were getting and we

actually had crypto confidential on like the title list originally and then I cut It because I just wanted I I didn't like it as much as everyone getting rich without me but then here's the crazy thing the sales team comes back and they say this title's not going to work like it's too hard for us to pitch this and the when they came back and they said that my first reaction was like you like I know what I'm doing here like this is my book and I said okay like I'm going to sit on it

for a day I'm I'm not going to immediately respond to the Email and I come back the next thing I say okay you I'm open to other ideas what did you have in mind and they say well what if we called it crypto confidential they said that yes it was the exact same idea that had been on my short list before I went and pitched the book and I said okay there we go that's easy right uh and I mean obviously kind of inspired by Anthony Bourdain right I I read Kitchen Confidential early on when

I was trying To find a good style for the book and he really influenced the writing style in a couple ways one he's just so fun and Lively and like honest about the brutality of the industry right while while clearly loving it and also being you know critical of some of the insanity uh and I knew the Big Challenge was going to be explaining technical Concepts pretty deeply technical Concepts in a fun fast-paced read and he does a really Good job of that where he explains some stuff within the story and then he has a

couple of call out chapters where he just goes on a rant about something about cooking right about like what tools you should and shouldn't have or something like that and it's totally separate from the story but it gives him an opportunity just go really deep on this topic but you can skip it if you just want to get back to the story and so that influenced some of the actual Structure of the book too because I said the first three drafts I tried to put all of the crypto explanations in the story but then you'd

have this fun fast-paced you know boom boom boom action sequence and then three paragraphs of explaining the difference between Bitcoin and ethereum right it's just boring so boring and so by pulling that out into those little in between chapters I'd say half the people skip them entirely they Just want to keep going through the story they come back and look at them later if they want to other people who are less technical love them because it gives them an opportunity to go deep on that and so that was super super useful and the thing I

was really hung up about was uh I don't want to use crypto confidential as a title because it it feels like I'm copying Kitchen Confidential and then they came back and they said well he didn't come up with That here are five other titles before that that used the same structure and it was also based on this like old magazine that was really popular like you just think he came up with it because he's the most popular one or like the most well-known version and I said okay that's pretty interesting and that's another thing that

commonly recurs right that a lot of the things that you think somebody came up with they just did the most popular version of on a scale from Like writing to your grandma who knows nothing about crypto and is like oh this looks like an interesting book to super ethereum nerd has been working in crypto since 2013 how did you think about who you were writing for and their level of expertise the two groups I was aiming it at actually I mean obviously I wanted it to resonate with crypto people right that was sort of the

first goal other people who lived through this I wanted them to feel seen to enjoy reading it But that wouldn't be enough for it to be commercially successful so the next two groups I thought about a lot were the partners of people who went through this so interesting I would that mostly wives and girlfriends right because it's such a male-dominated industry and there was this whole year and a half long period where me and coet and our couple friends would get together and five or 10 minutes into it all the guys will be talking about

crypto and all of the Women would be just rolling their eyes so sick of hearing about it CET call it dogcoin probably for a little bit it was just yeah or you talking about your doggy coin again she knows it's Dogecoin but it's sort of like a fun like tease right because that I mean that was the attitude for most of our partners right it was just like oh my God I can't believe you guys are still talking about these stupid coins and that that's not a dig at them right that was just we were

So obsessed and they were so uninterested and it it was like that was the industry during that period obviously there were some fantastic women involved in crypto but it was easily 80 90% dudes and so that was one market I thought about a lot was if you know if you were a partner you know you were dating somebody who's in crypto or just like heard your male friends talking about it or whatnot but you were completely disinterested in it could I Write a book that was interesting to them and that was one consideration so I

took feedback from women readers really really seriously more seriously than my crypto readers the crypto readers I took the least seriously because they already knew all the technical stuff so they couldn't tell me what was confusing they were already interested in crypto and so I didn't need to sell them and so their feedback was helpful for correcting things but it wasn't helpful for is this A good book but ket's feedback my sister's feedback a few other women who read early versions of it those were all extremely helpful because that really told me where is this

confusing you know where is this boring how do I make this more interesting to people who aren't like me and I think that really really helped and then the third was parents huh because there's so many people who were in their 20s who got really into this world and their parents were just Like what are you doing yeah parents are like are you losing all of your money are you making money like I heard about this big scam that happened yesterday did that affect you can you imagine here here here you've invested like hundreds of

thousands of dollars in your kids education so they can be a doctor or a lawyer or something prestigious and they're just like flippings exactly exactly right that's like a fit's worst nightmare seriously and but that was lot Of parents and then and most people don't know how to explain this stuff right and the the one skill that I did develop from all those years of online writing the how-to stuff is that I did get decently good at breaking down technical Concepts to a more lay audience so I was able to bring a little bit of

that to the book and say okay is there anything real here what's actually interesting about crypto you know what's what's a scam and what's not and that Was very helpful but yeah it was this question of how can this be interesting for parents as well so they understand like oh this is part of what you were doing or this is part of what was going on in that world during that time period tell me about this idea of you were looking at different books big ones that had been quite successful and you would basically said

thank you that a lot of these big books that we recognize and recommend they're actually the writers Aren't that good at every single part of the process I think you use the example of Stephen King not being as good with endings and you had all these different examples and yeah that surprised me okay so yeah let me let me yeah copy that I didn't say they're not good at all these like I the it they're not perfect in every Department right like I think that's how I would phrase it because they're obviously very good at

most of these things but I think We have this illusion that you have to nail every part of a book for it to do well and the the the example that I gave or that I like to use is you know name one of your favorite books antifragile BR seem to lip Okay now tell me two or three things that he doesn't do a good job of in that book right my brain doesn't really go there my brain goes to the things that he does do well right but if I pushed you a little bit

could you come up with One or two yeah right yeah so that is a really good example of you can and you know you can try this at home right think of one of your favorite books and then think a little bit harder like what's something that wasn't as good about that book right or like could have been better if I really have to think about it and maybe it's probably easier for us to do because we think about writing a lot more but I suspect that even more casual readers can do this too And

you'll hear people do this all the time right so a really good example is these these Romany books that are very popular right now right like the the Sarah J moss C of thorn and Roses whatnot you you ask a lot of women predominantly about them and they'll say oh my God they're so amazing they're so fun I love them this thing could be a little bit better about them but it you know like it's so there's always a little caveat there's often a little Caveat in there but it doesn't matter right because you don't

have to do everything perfectly you have to get certain things right but a lot of the things you can actually get away with not doing as perfectly so there's another Nathan BOS shot out he turned me on to Brandon sanderson's YouTube lectures I've heard those are great oh my God they're incredible they're so good it's the best online fiction writing master class that I've seen um That I've found so far at least way better than what you get if you sign up for master classes in a sponsor right no no I uh way better than

if you sign up for like master class and like take something that you pay they're incredible um and one of the things he one of the things he breaks down is uh this idea of Promise progress and payoff so every good story you can think of as having a promise this is what you're going to experience in this story the Progress which is you getting closer to that you know that climax that finality and then the payoff right the the thing that you get at the end that delivers on the promise in the beginning of

the book right so promise uh Luke Skywalker is going to become a Jedi and defeat Darth Vader like progress he's training with Yoda he's flying around with Han Solo and chewy they're like going all these Adventures payoff he you know reconciles with his father actually it's not Exactly what you expected it's a little bit of surprise but he also defeats him right there there's you're getting that payoff at the end of that that long journey and the really interesting thing that Sanderson says in those lectures is you can get away with kind of a mediocre

payoff and you can get away with being a little bit boring at parts of your progress but if your promise isn't good nobody will read your book you have to have something really Compelling right away that makes people invested in finding out what's going to happen to these characters in this world and there are caveats to that right so if you think of a book like Dune the promise in the beginning is sort of unclear because some of the main conflict doesn't arrive until 50 60 70 pages into it and so you could be reading

it in the beginning and you could be like I have no idea where this is going right like and then you put it Down and that's what most people did right that's why it didn't get picked up by any of the Publishers they tried to sell it to but the few people who got through it loved it loved it and then they could say no the payoff is worth it right like you got you got to just get through get through the first 100 pages and then it's going to be awesome like I promise you

and those people can you know get a book to succeed eventually but if you want to have the best chance Of succeeding you've got to have that really really great promise early on and so this kind of feeds into that theme of you can be bad at certain things right I think the other example I gave you was I Ran's dialogue right it's just not very good right it feels there's so many times when reading Shrugged where it's really clear that that it's no longer this character talking it's just her insert and normally like every

author has like one insert but in her books Like every character is her insert and so you have these kind of jarring moments of this character is no longer talking you're talking and you can notice it once you look for it but it doesn't matter because it's still interesting reading her philosophy and her philosophy is you know if you're into it the story is interesting and she can get away with it she couldn't get away with having a boring promise the promise in that book is one of like the Best in the world the first

line is who is John G and you're wondering who is John G for 350,000 words until you meet him that whole time that is the mystery it's the first line of the book and so she can get away with so much else because she's built up this mystery character so much that you are just so curious to find out who he is and why he matters and how he's going to play in this broken world that she's created that you'll get Through all the other shortcomings I call them shortcomings you know things that could be

improved in her writing to get there as you're thinking about creating these stakes and creating that promise how do you think about setting it up so intuitively I'd say we're going to come up with the most dramatic thing possible basically there was an earthquake I was on the 100th floor of the building it started trembling what happens next you know so I'm like Okay that's very dramatic but what are some examples of ways to do this in more mundane ways like who is John G is actually far more mundane than the trembling building yeah so

how do you create a promise that awaken someone's curiosity when it's not so dramatic and extreme yeah it's a good question the there's this really good book called conflict and suspense and it's part of the elements of fiction Writing series which is a wonderful series highly highly recommend it even for non-fiction writers because it will it will really enhance your story structure how you think about narrative all it's it's great and it's very nerdy very tactical and one of the books is called conflict and suspense and it's all about putting conflict and suspense in your

writing he says early on that the number one reason people drop books is they don't care about the conflict There's nothing keeping them turning the next page and so the the way that he puts it is the easiest way to create it is to show that there is some risk of death but it doesn't have to be physical death right physical death is the easy one that's the earthquake on the 100th Floor yep but another big one is like psychological or identity death right so you're going to lose who you are right or it could

be like a societal or a broader death you know like an Apocalypse Armageddon type thing it doesn't even have to be that extreme but like you know this community is going to fall apart something on that something is going to die because everybody resonates with that fear at a very deep level in all of its forms and so even if you have a very mundane thing you can probably find some way to suggest that something in that environment is at risk of dying failing ending and that death is going to matter a lot to somebody

so For you it's something like I have $10 million and I might lose it all well actually on the first page so this is literally on the first page of the book I say that I'm about to lose $100 million of other people's money and we edited the that prologue section to get that number as soon as possible while still establishing some personal Stakes so in those first two paragraphs you get I'm getting thrown out of bed in the middle of the night my Baby is crying my wife is angry at me and I'm about

to lose $100 million oh of other people's money which is worse than losing I think your own money to me at least that would feel worse and and we got all of that in the first page and it's a half page right because you know you've got the chapter uh heading above it and so that that's actually creating multiple deaths because it could be the death of a relationship it could be the death of an identity as Like a person who's successful in the space and it could be the death of like all these other

people's finances right and so that was super super deliberate and then taking that CU that doesn't actually occur until towards the end of the book taking that pulling it into a three-page prologue that happens you know later establishing that scene and then diving into what where I was nine months before of like what the hell is crypto and Getting really excited about $100 right it immediately creates that suspense right how is he going from getting excited about $100 to being worried about losing a 100 million of other people's money and how is that happening in

9 months right so all of that contexts gets set up right away and that I think does a pretty good job of hitting a bunch of those markers pretty quickly despite being you know a nonfiction book right like it all has to Be stuff that really happened you can still bring a lot of those ideas in it seems like the big meta Insight that you've had over the past few years is if I want to have influence and if I really want to cap at readers and like make waves at the scale of culture I

need to learn how to tell great stories yes and it's not just about facts yeah definitely my big realization was that I'm weird in that I really enjoy a concise guide to how to do things right Where you you give me the index card and I'll follow it and I'll do it I love it it be great like I love that concision and you have all these people online saying like we need shorter books like we need 30 40 50 page manuals on things and that audience exists that crowd exists but it's a very small

crowd right it's vanishingly small and most of those people are very nerdy kind of techy like me right and like I love that crowd they're most of my friends but they're Often not the people who really drive a lot of the culture and where ideas can really like resonate and so my big realization with this was one if I want to explain some of the crypto World a how to would be incredibly boring a fun story lets it reach so many more people but then going through this experience I realized for a lot of these

other ideas that I would like to do books on non-fiction isn't even the best vehicle for it it would actually be much better As a fiction book and so I have a bunch of these articles around our relationship with science and technology like the limits of knowledge and like religion versus science we've talked about this but like that to me is one of the most interesting questions in the world I love that question and I started writing non-fiction book about some of that and about that premise and I got about 20,000 words into it and

I said this is boring it would be I would love To read this book and a few my friends would love to read this book You' probably like it but it would sell 20,000 copies and then it would be kind of Forgotten and it would be something that like occasionally nerdy people like whip out but it wouldn't get very far I said what if I took those ideas and put them in a fastpaced thriller sci-fi apocalyptic situation and made a mass Market Jurassic Park style book that addresses the same Topics and presents the same conclusions

but in something that millions of people could read that could be made into a movie right that could reach so much further and that to me I think is actually a better strategy for getting those ideas out if I think they're worth spreading which I do uh and we talked about this a little bit too where that that's almost the ultimate Challenge can you take some can you take a a big idea like a really interesting you know Philosophy thought or whatever and put it into a mass Market Commercial fiction story right because you could

you know you could do Mass Market Commercial Fiction with with no underlying moral or whatever uh and you could do like just the purely moralistic like high fiction or non-fiction but can you can you do both that's a cool Challenge and that's ultimately the best way to get these ideas to spread yeah I was just thinking the brothers care of of so many of the Ideas are embedded in those characters and then you see the characters kind of pit against each other yeah and there's something real and visceral about that totally that's kind of like

a good villain speech in in a fiction story or in a movie is if you if you make a Disney villain that's kind of easy right it's like oh yeah they're evil right they wear all black they live in a scary Castle right like they're just a bad Person but if you can make a villain who's really an antagonist right just going against the protagonist in some way and they're doing something apparently evil but they can make a speech for it or an argument for it in a way that makes the audience go like huh

I can hear that kind of like that right like I think that's why black panther did such a good job right because the antagonist in there actually does make a very compelling case for like no like we Need to bring this to like all the black people of the world and like you're actually being like you guys are the Bad Guys by keeping this like hidden in Africa and I think that was what made that Marvel movie work a lot better than so many other Marvel movies cuz so many of the villains are just like

like oh I want to wipe out half of the universe it's like okay right like there's not really a good argument for that right or there's so many of them are just like Bad guys right but then you have a villain who's actually got a good point right and now the story is super interesting so that that's been really really fun it's been this whole new I mean it it feels like I'm relearning how to write again it's this whole new world of how do I you know make a convincing argument for this while also

telling a fun Story how do you write action and dialogue and interiority and like all the things that go into that to make Writing good and fun and compelling is this whole new world what have you learned about writing good dialogue I'm going to assume that good dialogue is not a transcript of what was actually said and there's a lot of like if you and I go out to breakfast or hanging out there's a lot of empty words where you're just saying things without actually saying anything at all and you don't really want that dialogue

so how is it different from actual conversation Totally I mean the like like you just said that's one of the first big things is that if somebody looked at a transcript of us talking at a coffee shop or whatnot probably 80% of the things that we said would go nowhere they'd be these little you know just tangents offshoots right because there you know Small Talk casual things whatnot and you can't really have any that because the dialogue needs to be advancing the conflict or the action in Some way right and so this is from conflict

and suspense but basically the the main difference between exciting dialogue and dead dialogue is how directly it relates to whatever problem is at hand in the story so in any scene in a book there's usually going to be a main character who wants something and something is standing in their way so to the extent that there is dialogue it needs to relate to that desire and that obstacle and it needs to you know Be relate to like solving the obstacle and because of that often the best dialogue even amongst friends in a story has to

have some element of adversarialness to it there has to be some tension so I'm trying to convince you you know like let's keep this podcast going another hour and you're say like no I have a meeting and I said you can have another meeting another time right there there's some challenge in there whereas if we if I just said Let's exlain the podcast another hour and you said yeah that sounds great that'd be boring that's not interesting right if we just agree on everything and so there has to be like constantly some tension in the

dialogue so that's like one element that keeps it going the other another one and I have a whole list of this somewhere but another one that's really helpful is like redirection in dialogue so say I said let's keep this podcast going another Hour the reader in their head is immediately going David could say yes he could say no but what if you said something like oh we actually have another two hours already like it's actually already scheduled for 2 hours like we just started right and then we've immediately created this new scene where why does

Nat think we need another hour and David thinks that we just started right like is one of them like on drugs right like what happened here That there could be this disconnect between them about what's going on right and that creates a whole new level of Intrigue where by not just doing a simple yes or no you've now taken it in this whole new Direction the reader's like way more interested right and then kind of a third thing that often really helps is like non-verbal response right so I say David we got to keep this

going another hour this is great and then you just get up and Leave right right it's like no response you just walk off and then now sudden and then the story jumps into my head where I'm like oh my God what did I do what did I say like what happened why did he leave I'm like peeking out the door to wonder where you went right that is even more powerful than you saying no you just leaving so there's all these little things you can do that make it way more compelling than simply like yes

no agreeing with each other talking About nothing and it has to be really really economical in that way and it could be economical while being verbose right because you might need a long paragraph to explain you know why you think that we shouldn't keep going but there are those little things you can bring in there to keep people wondering like what is going to happen next in this disagreement that's a great answer it just made me think of the Aon sorin line where he says that every scene is About intention and obstacle mhm what does

the person want just like what you said what is the obstacle that stands in their way and he says if you watch a movie at all points you should be able to say what is the character's intention what is the obstacle intention and obstacle and he says I worship at the altar of intention and obstacle I love that line and it really shows up in what you're saying the the other thing that's really helpful with this and once you Hear this you're never going to be able to unhear it and you're going to notice it

in everything you read and everything you watch which is basically yeah every almost every scene that is keeping the action in a story going ends in either a yes but so the character gets what they wanted but there's some unseen consequence that comes with it or it ends in a no and so they don't get what they wanted and something else has now happened that is Changing what it is they're seeking or what their situation is and this is how you usually transition from one scene to the next is I say you know David let's

extend this another hour and we bicker for a little bit and you say no and we're going to end this right now right and I mean you wouldn't say that actually but that's like what would happen right is not only did I not get what I wanted I got something worse and now the stakes have gone up a bunch Because I'm like well I just screwed up this podcast like what what do I do and so now the next scene is like how do I get back in David's good graces right we've created this whole

new conflict just by adding the stakes to it right or you say yes we can extend another hour but we're going to do it while running around the lake we're going to do you know get treadmill desk we're going to do on the treadmill desk right like that's maybe a silly one but you could Think of something else where it's like okay Knack out what he wanted but or we'd say like you say you could say yeah actually we're going to go until 6 right like we made that joke before we started and that's added

a whole new Stakes to it too right it's like oh okay like it wasn't exactly what I wanted and now I've got to react to this situation right and that's a lot more interesting than if I just got my goal and a lot of stories it's not obvious when you're Watching them but usually the character is getting further and further and further and further and further away from their goal as The Story Goes On because they they they have some big problem and then they rush out to try to do the easy solution and that

fails and that takes them back to here and they're like okay well now we do this thing and then it's going to work it's like oh no now you got to go back to here and they like okay we'll try this thing and That'll something it's like oh no now you're back to here and then eventually you get to some climax where you just get all the way back up to the thing that you originally had at the beginning but if you're steadily getting closer it's actually boring because the stakes aren't going up and uh

this is a lot of good Nathan BOS shout outs he had a good tweet about um Chris noan Chris for Nolan he draws all of his stories on a big Whiteboard or a big sheet of paper as visuals so like I think Inception is like you know they're on this level and then they get further away from their goal because they go down to this level and then they're here for a bit and they get further away from their goal so they're down on this level they get further way right and you can he draws

out a lot of his stories in that way like I love to see what the tenant drawing looks like that's got to be Insane but it's a cool way to think about your story how am I getting my how am I getting the characters further away from their goal by introducing expected new tensions to each of these scenes we're talking about the craft of writing here and one thing I've noticed is that in the world of food so much of what I read is overdone and overwritten I think of cookbooks I think of elaborate descriptions

on bougie restaurant menus and I don't know about you but all that Has deceived me into thinking that writing about food has to be complex in order for it to be successful but I've come to realize that's just not true you don't need fancy language to write about food common language works just fine and for an example I want to look at John Steinbeck and his book his Masterpiece East of Eden and as I read this paragraph I want you to notice the Simplicity of the language here okay it goes like this the apple Pie

was golden and fragrant its crust delicately Brown and sugar crusted with the faintest hint of cinnamon wafting up the apples inside were tender but not mushy each bite offering a balance of sweet and tart that made my mouth water the warmth of the pie coupled with a scoop of melting vanilla ice cream made each mouthful A Little Piece of Heaven aoking memories of long and lazy Autumn afternoons first of all that is beautiful writing and second of all I'm Hungry I want that apple pie because this paragraph is alive isn't it and the words are

so simple there's nothing pretentious there's nothing pretentious about it but what's going on here let's break it down Steinbeck's description comes alive because it's so layered what he's doing is he's appealing to multiple senses there's sight there's smell there's touch there's taste there's all four and you can see the golden the delicately Brown and sugar crusted crust You can see it you can practically touch the warm pie the scoop of melting vanilla ice cream and then you can taste the faint scent of cinnamon that's wafting up the tender but not so mushy apples you can

taste all of that and it's the collection of these very descriptions the diversity that he has going on here that's what's giving this paragraph life and then there's the pacing Steinbeck wants you to linger on the details he wants you to slow down And save for the paragraph with the same kind of presence that you'd bring to a delicious slice of apple pie and I want to look at how he does that with structure and with punctuation so we look at this paragraph there's three sentences and the whole paragraph is a single fluid continuous thought

that goes from top to bottom every sentence roughly the same length what does that do is it gives every sentence equal waiting there's no one place that he Really wants you to focus within those three sentences there's a total of seven commas and what those are doing is they're just serving as gentle pauses gentle pauses gentle pauses because Steinbeck is asking you as the reader to just slow down and feel the deliberate and unhurried Pace that he's describing right here when he's talking about these long long and lazy Autumn afternoons he just wants you to

peace out relax it's sort of like being on a hammock you know And then finally there's the sequencing which pulls you into the intimacy of the moment it's like a slow zoom in shot in a film where he's starting from far away and just moving closer and closer and closer and closer adding suspense to the moment how is he doing that he's going from eye to mouth to mind so how can you apply this to your writing well if there's one takeaway I want you to remember it's this there's no need to show off with

super duper Fancy $100 words you don't have to do that you can have an uncommon effect on your reader by using common language to describe a common experience just like Steinbeck and I do a writing example like this every single week if you want to check them all out go to writing examples.com and when you get there you can enter email right at the top of the page and if you do I'll just send you an email whenever I publish one so about once a week and then you can just learn All about the craft

of writing okay back to the episode so how do you think about the stories that you're writing like I could almost think of different ways it's like I'm working to the last line this is what Robert Caro does I map out the entire story and I basically had the Arc of the book and then I had all the different stories mapped out and I'm thinking about the emotional weight hey I'm actually working to a moment of change inside of the story and what I'm Trying to do is basically have the black here the white here

and then as big of a contrast that happens in that moment of change or I have my intro story which then sets up how the rest of the story goes I'm sure it changes over time but what sort of what are you keeping top of Mind as you're writing a story totally uh so for the Sci-Fi novel because I feel like that's the most relevant for this question I actually started with a different sci-fi novel which was set in Like a semi- post-apocalyptic future where the population has gone down by 99% there's a very small

number of people living but the people who are living are basically living to maintain these massive servers where the rest of Humanity's Consciousness is housed because everybody uploaded into the machines right we figured it out we passed AGI we created a direct link between your body and a server and then you could just Walk your Consciousness into the machine but somebody has to maintain the servers right so you've got all these people left out there who are living and and keeping it running and then you know a big conflict evolves in that situation as I

was working on that I added these like journal entries from the old world before that event happened as I was writing those journal entries I thought this is actually a really interesting story too I want to go back and write That story first and so for the novel I'm on now I knew that the end goal was this world eventually and it might take three books might take four books or it could take a long time to get there um but what would have to happen that not only would we achieve this technological breakthrough which

I think to some degree like some version of that is probably going to be available eventually but not only could we achieve it but that most people would elect to Do it right like what would happen in that world and that was a really fun premise because all I had to do was ask that question right what would get us there and a couple of plot lines very naturally emerged from that right it's like who's working on this Tech like what else is going on in the world that make would make people prefer a digital

life to a physical life and these are all questions I'm very interested in anyway and so for me for the first book It was I know it's not going to end at that world at the end of this book but it's going to end somewhere closer to it and it's going to start at basically where we are today maybe in five years so how do you go from here to there what's happening along the way and then it was easy for me to write the last Act kind of some of the final stuff that would

happen and then from that it was easier to write the first act because it was like what would be the inciting Incidents that would lead the characters to these Ultimate Events and then it was kind of just like working backwards from both ways into the middle until they linked up and the linking up was hard like that was the biggest challenge actually was how do we finally thread these together but knowing where it was going to end and what might have started the characters on that path gave me a really good starting point to fill

in the rest you were talking about Intention and obstacle and stories but I want to hear that for your own life and your own writing process where do you feel like you have that obstacle in your way right now that's been consistent challenge last couple of years going through this reinvention relearning writing process of I know great writing when I see it and when I read it right and it's just so beautiful and was blown away by and in very different styles too right like the beautiful literary Writing can really appreciate that the really fun

fast taste Sci-Fi Action writing can really appreciate that different styles and I don't feel like I'm there yet right and I I mention this quotation all the time because I love it so much from Ira Glass about the taste Gap yeah The Taste Gap so good so good right and for anybody who doesn't know there's you always go through this period as an artist of you know good work you've you have you've been cursed Because you've realize the difference between good and not good but you can't summon good yet and that's a very painful place

to be in because you you can work really really hard on something and it just isn't where you feel like it's good yet or good enough yet and I mean the really interesting thing is that you never fully close that Gap and to some degree you don't want to because once you feel like you've closed that Gap you stop learning gets boring gets Boring um but also if you leave that Gap open too long it'll drive you crazy right like we were talking about David Foster Wallace in the beginning and his the emotion in his

writing and it's very clear that he wrote infinite G to try to write something that was good enough to him and he failed I mean he killed himself you know like that the one of the main characters in the story is just horribly suicidal because he never thinks his work is good Enough oh wow it's awful awful awful like it'll never be good enough he's an alcoholic right like he's clearly kind of a standin for how DFW feels about himself and his work and I mean this isn't a spoiler it happens early on he kills

himself right and so that's actually to me what makes that book so powerful is that it that's ultimately what happened with him right and so you leave that Gap open too long and you could be the best in the world and you Could still not be good enough for yourself to feel good about yourself and so to me the big challenge is okay how do I look at my work see where it can be better try to implement that without always being so hard on myself because my immediate instinct is to look at it and

go this isn't good and then I show it to somebody and they say oh this is really good I enjoy it and then my reaction isn't oh my God thank you it's you're lying right or oh well you just Don't know good writing right and those are terrible reactions to have like like it's for me and for to be thinking that about somebody right but if I'm honest like that is where my head goes right and and so pulling that back and developing a healthier relationship with it has has been that kind of like big

challenge the thing I'm trying to do more of is it's good and it can be better right right kind of a yes and right because I think that that's Definitely a healthier place to be and then the the fun challenge is okay I'm reading this I know there's something missing what is it right and then I'll go and read other books you know so I'm I'm working on the Sci-Fi novel now and I was I was I got the first draft done and I was looking at it and I felt I said you know it

feels like there's something not right here and what I realized it was was that I got so into the Fastpaced heavy on action heavy on dialogue that I lost the description of the environment around the characters and I lost some of the interiority and their reaction to it and so I said okay I need to actually stop reading Red Rising and like Blake Crouch and some of these really really fast-paced books and I need to read slow books where there's tons of that and East of Eden is a great example of this because if I

can prime myself with those kinds of books then When I go back and edit this I can draw it out a little bit more and I don't want to do it too much because I don't want to lose that energy like we were saying before a little sentence here and there makes a big difference and so I I mean to me this has been the biggest unlock is finding what you need to Prime yourself with before you write every day well I think that the times when I'm not there yet and I feel the most

frustrated or when I know I'm not there yet and I Don't know why I'm not there yet mhm and there's just this big nebulous monster of a problem and I'm like I don't even know how to attack it and then I'm like okay here's the problem my descriptiveness of human emotions and what I went through isn't good enough okay so that's good so now what we can do is we can go find people who've written about that in the non-fiction sense and then find people who do it really well and then we could just like

Bathe in those ideas for a little while and then you just find that those ideas they they rub off on you and then you begin to implement it in your writing the thing is learning just takes so freaking long but once I know what the problem is I can kind of have a sense of Peace cuz I know where I'm going it's not knowing what the problem is that drives me ins that's a good point yeah you you figuring that out is a huge challenge in and of itself and sometimes It you you almost can't

even name it but you know that the thing that you're reading is solving that problem somehow is a i this is a total tangent but it works for this which is there was this study done on toddlers in like an orphanage where a lot of them came in with sicknesses various diseases and they realized that if they just gave them a ton of different foods they would naturally take the ones that addressed whatever deficiency they had And so they had this intuitive sense of what their body needed and they were naturally drawn to that as

long as they weren't interrupted with processed food and things like that how about that and so I feel like there's a little bit of that with reading and writing where if you're if you know that there's something you need to improve on then you can kind of like sample a few things and you might find one where you say wait this feels like it's doing what I Wish I were doing and then maybe you can break it down from there and say okay like what is it about this that feels like it's it has what

I'm missing and then maybe find the problem from there that's what I've been trying to do constantly that to me is one of the big values in Reading broadly at this point is you know how do I find more of the things that I'm lacking so that I can yeah OBS get them via osmosis and then bring them to the writing osmosis is the Right word for it the other thing that is an obstacle that I think you've had to overcome is you started off as an internet writer you had the medle for many years

where writing your newsletter you published all these articles you're getting all this feedback you're tweeting all the time and it's like ping ping ping ping ping people are constantly saying good job Nat hey I didn't like that one as much but you're in constant dialogue with your audience And then you go to write a book and you don't have any of that Advantage you end up building an app to basically solve this problem yeah I mean going from online writing to doing the book was really really hard the especially in the beginning because I was

so used to the immediate feedback of tweets of writing articles nothing sat in my draft folder for longer than two weeks and so to then start on something that I knew it was going to be two years before people were Reading it it didn't scare me in the beginning but as I started to work on it more it got harder and harder and harder because not only was I working on this in the dark I was doing something in a completely new style I had never done before right right so I had to learn this

whole new writing style and then try to apply it to a length I had never done before and there just all these challenges and then to not be getting any feedback along the way and to know That it you know wasn't good for the first draft right so sitting down to work on this for three four hours a day feeling like it's bad and not really having anyone to look at it and tell me otherwise and so it really really really was like driving me crazy for months it got really really bad and I finished

the first draft and well I got close to finishing the first draft and I just I felt so burned out by it but I took a couple of chapters that I thought were Good and I sent them to my editor and I said hey can you just look at these and tell me if I'm on the right track here right like I I'm feeling like really lost burned out whatever and he came back the next day and he was like n these are really good like you're you're on the right path and he's like obviously

there's still work to be done but if you keep going at it as you have been like with what you're showing me right now like you're going to be in Great shape oh must have felt great oh my God it was it was just like I didn't I didn't realize how much I had been holding on to by not asking for feedback and I think I wasn't asking because I was scared right like I was scared that if I sent that then he was going to say you know maybe we need to rethink doing this

book something like that right uh we had just signed the deal two months ago right like maybe they could have backed out or you know I Was really scared but him saying that I was like oh my God this is such a relief but I still had this problem where I was working on this in the dark and not getting any of those dopamine hits and I had quit working in crypto so I wasn't doing anything there I still had my blog but it was less of a focus so I was basically just doing this

so I finished that first draft and I took the advice to let it sit for four to six weeks and I said okay what do I do with this Time and I'd been talking to Thiago a little bit and he had been saying that there's a surprising amount book traffic coming from Tik Tok he was like all these people on Tik Tok are talking about books he said like I never go on Tik Tok I don't know anything about this but it's apparently the new platform where people find their book recommendations and so I said

well that's kind of interesting let me go look at it and you know I I got on Tik Tok and I started looking at the book talk people and I immediately went back into my like marketing analytical content brain where I could see how the algorithm was working so I used to do all this SEO stuff and like it was a skill that I got good at I could see how the algorithm was working I could see what you needed to do to kind of like game it and I said well this would be a

fun project while I'm sitting on the bookd draft let me just see how many Followers I can get on book talk and so I started making bookt talk content and within in those six weeks I got up to like 50,000 followers on Tik Tok which was like really cool and you know I think now it's a little over 100,000 I've got almost 180,000 on Instagram or something like just doing content and I did most of that over the next six to eight months and went super super hard on it and was like you know this

is a great way for me to promote the book Once it's out uh but what I think I was really doing was I was finding an outlet for the dopamine need right it was really hard not getting some win on a daily weekly basis while working on the book and so I needed this other thing to fill in that space for me it's funny is very tangential but I've heard from different Founders who run boring companies that one of the best things you can do is have get really into like race car driving or some

super Suspenseful hobby because then you don't need the suspense in your business and you can just have number go up in SAS company yeah and then you can just get your suspense somewhere else I think that's really good advice I think you I needed that outlet and it was great for a little while but the the time demands kept getting bigger and bigger and bigger and then I hit this point this past Thanksgiving where my my family was in town my daughter was off from Preschool I was pretty strapped for time and I ended up

spending the bit of time I had on Tik toks and YouTube videos instead of on the Sci-Fi draft and after that week I was like wait this is completely messed up this is not what I should be spending that time on this is not my top priority I'm prioritizing it because it's giving me that dopamine and so I reacted kind of drastically and I said I just need to stop like I'm it's like I know I'm very Addict like with things where it's hard for me to do them halfway and so I said I just

need to quit entirely maybe I can pick it back up lightly at some point but this can't be getting in the way of the writing because it's like the number one way you fail at writing is to stop writing like if you keep writing and keep publishing your odds decent of something working eventually but most people quit before they get there and so it would be pretty easy for me to just Go off on this side quest of book influencer when really I want to be the one writing the books so I I quit and

I took a break off for December and then in mid January I finished the first draft of the Sci-Fi book and I said okay what do I do with this period after this first draft is done in my head remembering that if I'm not careful I'll get like sucked into something that could become a new job a new obligation and that was where the Writing tracking app came from was I was like okay the problem is that I'm not getting a dopamine hit from writing a book every day or working on the book every day

so I'm going to make something that gives me that dopamine hit which was this prolific tracking app where it's was like all I all it needs to do is let me log how many words I wrote and like what project I was writing them on and you know it'll like straa you can follow people and see their writing Sessions and whatnot and then I can see oh like Nat did this many words this week in this month and this year and you know banged out a basic version of it with our friend a deal I'm

going to try to have it on the app store by the time this comes out that's my goal for myself because I'm I'm in between drafts right now so I have some time to work on it again but I got it to a basic enough point before I picked up the second draft again that I was able to just log My writing sessions there every day and for me huge huge Game Changer in terms of getting some social win for working on a long-term writing project because I had this tweet and and this article about

this that did surprisingly well about how I think a lot of writers are like getting good at the wrong thing in that they're too focused on writing better Twitter threads writing better LinkedIn content and to some extent writing Better articles where those are all really useful skills to get you to a certain level but to me the thing that would last more from those ideas is like if they turn them into books or even pamphlets like something right because if you think of any writing that's lasted it's not newspapers and magazines right which is what

blogs are kind of competing with it it's books right and so I want more people to spend less time on their Internet writing or at least do it to build up an initial audience and then with that audience go on to do a book or like Anna is a perfect example of this right forga yeah she you know that that to me is like just an awesome trajectory right such a good example of taking to get to the next thing um and yeah having it it it sounds like almost embarrassing and stupid for me to

say this but having a little app where I can like show the world that I wrote today without having To publish anything it makes a difference we are monkeys after all yeah yeah totally I think I just want to ground the moment in time here because I think it's really important for adding a lot of context for what's going on so you have crypto confidential now coming out in like a month and a half or so but even though that book hasn't come out yet you're done with the draft of your next book which is

a science fiction novel so I think that that's just Important now because you haven't had this book really out in the world what is the thing that you're the most insecure about in terms of the release like what's the thing maybe keeping you up at night of I'm unsure about that or something in my writing style I guess obviously if I mean nobody buying it would be the worst thing right because to some extent if somebody likes it and thinks that part of it sucks they at least read it Right like they still bought it

right like I still got their money you know like bad reviews to me are less painful than no reviews no reviews right and we we had this thing this past week where Publishers Weekly which is a it's a very inside baseball like website for people who work in publishing where they review any new books that come out and the person who uh read it and reviewed it I think just like didn't get it because it was the weirdest review I'd Ever seen where they kind of like half of it almost looked like an AI generated

summary of the book and then they said like well his points get confounded by the fact that he like didn't lose all of his money and the last Line's like this one's a head scratcher right so they they clearly didn't like it very much but they also didn't say it was bad just like it was a weird review anyway at first I was like pretty upset about it all right they didn't like it and the Thing that was actually helpful though is I said you know there are so many people who never even get looked

at by something like Publishers Weekly it's cool to be there at all right and that's kind of the mentality that I'm trying to take with it but yeah I mean really the I think the big thing would be if it comes out and just like nobody cares right nobody reads it or I guess the the thing that I'll be worried about is if I get tons of feedback that people Like got bored and didn't finish it more than Norm normal right but I guess normal is 90% or something of books don't get finished right like

so it's hard to say how bad that actually is but if I felt like despite doing all of that work to make it fun people still weren't enjoying it and I'd be like all right you know frustrating but it it's a good book I'm not saying that it's not good it is a good book and I have gotten much better at writing since I finished it so Not like much better I've gotten better at writing since I finished it just from doing the Sci-Fi work right and so I know that if I went back and

did another draft of it it would be an improvement and so I'm I'm okay with people saying oh you know this could be better because I'd probably be like yeah that could be better right but at some point you just have to be like okay it's time there's a great back and forth in this conversation that Louis C K had With Theo Von and Louis C K goes how long you been doing comedy for and Theo goes like 18 years and Lou goes nice man only 18 years like man it's you know after 25 years

that you really kind of begin to get the hang of it and it was just one of those things where Lou sort of playing the the role that I think he's deserved as sort of like one of the legends of Comedy who sort of been there and Theo sort of on the come up and you hear these numbers 18 and 25 and Lou's like yeah man you know you're just you're just getting started and I think that's the other thing that I throw back at you is what have you been doing this for two years

in terms of this sort of book writing and I just think of that story all the time of just how long it takes I mean Seinfeld is 70 years old and he's still getting after it still improving you know it's so easy to focus on the people who had Immediate success had a first book that crushed it right like Stephen King wrote Carrie when he was 26 you know and that was his first book deal and he got 200 grand for it which is something like 600 Grand in today's dollars right that's an insane deal

and he was literally living in a trailer with wife and two kids when this happened right so you hear that story and you think well if I don't have a half a million dollar book deal by 26 then I'm a failure right or you Red Rising is a good example of this too Pierce Brown wrote it I think when he was 27 or 28 and it's like one of the biggest books amongst like male sci-fi fantasy readers right now and you know you see that you're like oh okay well I haven't done that and so

I'm a failure right but you know there's like you said most people this is a 10 20 30 year journey and to me that's actually what's kind of exciting about it is that it's something you can get better at forever If if you let yourself right if you keep thinking about it right like Steinbeck said that East of Eden was the book that he was preparing for his whole life so like to him Grapes of Wrath was a warm-up wow right like Of Mice and Men was a warmup right like imagine warming up with of

mice and right that that's such an incredible mindset to have uh and I love that right I mean it would actually be way worse to have your first book be a breakout success in some ways That's harder that you never catch up to I I I I feel bad about this story sometimes but I'm going to tell because it's a good example of this uh you know go to leer Bach by David Hof Douglas hoffstead uh phenomenal book my friend and I Neil read it and we did an episode on it for our podcast and

then Neil emailed him and he said hey you know we'd love to do an interview with you and talk about GB because you know such an incredible book and he he emailed us Back and he said well you know I might be open to doing that but I've written a lot of books since then would you like to talk about one of those and I could kind of tell from the tone that there was a little bit of like like and it's you know I I think that most people would say that his later books

haven't had that same mass success that GB had and that has to be kind of tough right it's got to be a challenging thing and so while I would Love a massive initial success for a book I would also love the idea of like the Steinbeck mentality where it's just like no you know we're just going to keep getting better right it's going to be the next one the next one the next one um yeah because you can I mean you can literally do it until you're dead corack McCarthy published his last book and then

died what a month later yeah how about that Robert good way to go rob car is doing the same thing right now You know hopefully George R Martin can do that too okay let's do a i around so what I want to do is I guess you have this checklist for telling good stories and what I want to do is I want to go through all of them and then in 30 seconds for less just hear your okay reaction employing all five senses yes so easy to forget that you smell things especially it's most people

focus on site and they'll occasionally throw in sound but if you add even half a Sentence about the smell of a place it just brings it to life huh if I can go longer than 30 seconds okay there there's been there's interesting research that people who lose their sense of smell have a very hard time developing deep relationships with people what yeah so we never think about how we smell but we're clearly using our sense of smell to like judge people around us to pick up on their emotional cues things like that and when You

lose that you lose some of your ability to connect with people so it's this cool sense that we very rarely think about unless it's really overpowering you know awful Bo or an Incredible you know food scent but you add a tiny little detail to that of that to a scene and just brings it to life yeah one other thing is also smell is so related to memory that like I always think of the smell of my grandma's house like Grandma's houses just have a smell Y and and you say that and I immediately have it

in my head too yeah that's strange keep the inner enemy in mind uh yeah so this is kind of a fun it goes back to like the death right where in in in every story there's obviously going to be some external conflict but there pretty much always has to be an internal conflict they're struggling with as well right and it could be you know what choice am I going to make at the end of this you know do I actually want to go Through with my destiny or this kind of like Campbell's hero's journey right

you need the refusal of the call because that is what shows the audience that this person is just like you they're unsure if they're willing to take on this heroic Journey or not right they they weren't like born for this necessarily like they're going to be conflicted about what's happening and it can be easy to forget that at least for me if you're just in the action of What's going on and so you have to find Opportunities to take a step back and let them think and react and actually have a hard time making these

decisions so the audience knows that they're still human like them how about that next one how are you changing oh yeah so kind of like what you said earlier about how you're structuring a story a lot of the times one of the things that you want to be building towards is some meaningful change in the character right like going Back to Campbell's Heroes Journey they have to return to the world they began in but they have to return changed in some way right like Luke skwalker goes home but now he's this incredible Jedi starts in

the Shire ends in the sh starts in the sh ends in the sh exactly and the Shire has changed too right and they have to clean up that mess anyway so you you need to know what is that change going to be and how is the character going to get there and it's Going to probably be it's definitely going to be an internal change so they're going to accept some truth they've been avoiding they're going to some part of their personality is going to die right like I think that's a really important one that's why

we used to have all these rights of Passage was to like kill the boy so he can become a man literally yeah you know you you kind of need those events to happen again so there's a deeper emotional resonance With the character than just they went on this like action adventure love it stimulus internalization response okay this is a controversial one which I didn't know when I wrote that but then I read more about it and well let me explain it first okay so a good way to structure a beat or a part of a

scene is something happens you think about what happened and then you respond to it David gets up and leaves the studio Nat's really Worried about like what he might done to upset David Nat gets up and looks out the door you can kind of just do that over and over again and you'll create like a good set of scenes the controversial part is how much internalization do you need because let's let's compare two ways I could write that David gets up and leaves the studio Nat you know and then we're in my head Suddenly It's

like Nat was suddenly terrified that he had upset David right With that comment that he made about this being controversial so then Nat goes to the door and looks out or you say something like Nat's leg started like bouncing uncontrollably and then he dashed to the door to see where David had gone right there was no internalization there but you immediately understood that I was really freaked out and that's in some ways better and so that you always need the stimulus in the response right because That's basically just what's happening and then the question is

do you actually need to go into somebody's head for this or can you just show them doing something where the audience immediately gets yeah I think that you're really getting at something where you don't always need to be so literal there's something about just the shaking the legs that just implies so much of what's going on the heart rat goes up oh my goodness uh oh You're worrying and actually sometimes by saying less you can end up saying more because the reader can fill in a lot of the extra information with what's going on in

their own head which actually might help them dive deeper into the story this is actually kind of a curse of getting too good at writing is that some people especially I struggle with that all the time it's like you kind of want to show off right right you want to show oh the Depth of the emotion or whatever it's like Nat flashed back to a time when his mother ran out of the room after you know you want to like bring all this stuff but the reader just wants to get to where did David go

right right and you in some ways it's better to just not try to be artsy and just show the action uh and it's like I don't know if we're going to talk about AI stuff much at all but this is one thing I've noticed with like Claude Opus versus Claude Sonet is Like Sonet is the cheaper and worse model but if you give the same sufficiently complex prompt to both of them Sonet often comes back with better writing because Opus is trying too hard to look smart how about that yeah it's like Opus is insecure

or something yeah Opus is trying to prove it's got that MFA for a reason or something yeah exactly I don't think it's that you're too good at writing I think it's that you're a really good writer and you're Insecure and so then you're insecure can show up and just trying too hard totally you know happens all the time let's do two more then we'll get into AI is the antagonists opposition clear yeah this is it kind of goes back to that idea of like goal and opposition right is they're there needs to be some large

antagonist usually from pretty early on in the story that they're fighting against and sometimes it could be themselves it could be their environment Doesn't have to be a person but there has to be an obvious thing keeping them from their goal and you sort of have to be continually reminded of that uh of that obstruction to the goal the best explainer I've seen of this is actually a nerd writer video oh he's so good he's so good about the first 10 minutes of top gun Maverick have you watched this one I haven't seen this one

oh my God this is a phenomenal video on doing this perfectly without it Being obvious because in every scene or whatnot there's your goal and there's the thing standing in the way of your goal and you kind of want to remind the reader or The Watcher of what those are and so what he does is he breaks down the intro scene of top gun Maverick where they've got to take their jet to mock 10 to win this contract and he shows you that at like seven different points in those few minutes they say you just

got to get to Mack 10 you just got to get to Mack 10 you just got to get to mock 10 like they're going to take away our funding they're going to take away our funding our funding is going to go away like we won't be able to keep going like and when you put them all together it seems ridiculous but then you show it in a scene and it just flows really naturally and so to some degree you almost need to like beat your reader over the head with a reminder of what they're fighting

for And against without doing it too much right and that can be a tough balance too right that's the art final one emotion thought decision action pretty similar to stimulus internalization exactly that's another way to think about it right so that's how you can structure the um internalization is you feel something you think about what to do you decide what to do and then you do it but obviously if you do all of those each Time it becomes really like kind of stilted and so you can you know pick and choose from within them but

then again it goes back to how much do we use and how much do we leave out and how do you use that checklist do you finish a scene and then look at them do you look at it before you start writing when I was doing crypto confidential I so at this point I've internalized a lot of that where I don't need to like use it as a checklist anymore more but when I was Learning it and studying it I broke down the entire book by every single stimulus and response I was like this thing

happened so then this thing happened which caused this thing to happen and then this thing happened and so the whole scene it was almost like a spreadsheet of exactly what each of the Beats were and then anytime it felt like there was a weak response or a weak stimulus I would like change that to keep the action going a little bit and That was a really really helpful way to break down the book in the beginning and then I I had more of the emotion thought decision response and then I ended up cutting that out

because I could tell it was feeling like overdone but it was very helpful for creating some initial structure that you could then take away cool I I'll throw one more that's not on the list yeah that I've been really interested recently that I think is incredibly useful which is called Braiding and so I hadn't heard of it either until I found a video about it but basically the idea is that there are four components of a good story which is the action what's happening the dialogue what people are saying to each other the description of

the scene where it's happening and the internalization the interiority how people are reacting to what's going on and a a bad writer will just do one or two of them it's just action and dialogue no internal World and they're in a white box a good writer will do a mix describe the scene there's some action they're talking they're thinking about it they're talking some more there's some more action but a great writer weaves all braids all four of them together seamlessly so that you're never obviously in one or the other so you walk into the

room you notice the pop of blue and purple that creates this warm beautiful environment David asks if you Want a cup of water you think should I have Stiller sparkling sparkling what make me burp David Goes to the fridge and grabs a water like you notice how immaculately organized the fridge is right you you know the the records on the wall catch your eye as you walk back into the studio like each of those are half a sentence or a sentence but they're all just fitting together whereas if it was I walked into the studio

and I sat down in the chair and Then it's three sentences of like what the studio looks like and then five or six lines of dialogue between us and then me thinking about something it feels way more broken up right so to the degree you can weave all four of them together the more natural your story is going to feel and that's apparently a big thing that editors look at in particular for the difference between a good and upcoming writer and somebody who could be like really great is how Well they do that and give

me those four again uh description action internalization and dialogue cool yeah let's close with writing with AI I couldn't believe you showed me that tool novel crafter and you figured some pretty cool things out so how are you using AI to write your science fiction now and how would you think about even edding the checklist or the braiding into the prompt that you give the the tool yeah so shout out to novel crafter This is novel crafter and Lex like Lex is the best AI non-fiction writing tool that I found for articles and things and

novel crafter is the best AI fiction writing tool that I found but to be clear in both cases they're not that good out of the box you have to work with them and 99% of it is how good your prompting is and how good your writing style is and how well defined it is so novel crafter is kind of like scrier it it lets you organize your book see all The scenes all the characters where they recur the plot points things like that and then you can bring AI into certain parts of it so one

thing that I'll do a lot is I'll be writing and I'll hit a point of writer block where maybe I know what's going to happen next but I'm not as good at describing certain things so I say like okay describe this for me or I'm not entirely sure what should happen in between these two points so I say like let's come up with some ideas for This and in novel crafter you can kind of like do those prompts right in the document editor but when you're doing those prompts you're actually feeding in a custom prompt

that you have designed that can be incredibly complex so whenever I ask novel crafter to help me write the next couple hundred words of a scene The Prompt that it's actually The Prompt that I'll type in is Nat and David walk out to the kitchen to get some drinks before they record that's What I type in on the back end it's getting about like six or seven thousand words of context where it starts off saying like this is a Sci-Fi novel here is the plot synopsis right here are the main characters here's some background info

on each of them and these are the characters who appear in this scene here are the last 2,000 words of the book to give you context on what's going on right now before you start writing make sure you read this writing sample and Then I have a 3,000-word writing sample that I feed in of like my best chapter and do you describe what that writing is like explicitly yes so after I feed in the writing sample I then have a big checklist of this is good writing to me like how to describe things how to

do dialogue how to do action um what's on there there so one of them is broader where it's like this is a Sci-Fi Action novel but it touches on deeper philosophical questions about our Relationship with science technology so it's okay to take a beat to dive into the details and not always focus on the action it might be something like that is part of it or the scene the the story needs to maintain a certain degree of tension so even though it's so it's science fiction we should also think of it like a thriller right

like a a Stephen King book or something like that little things like that to guide the style and Then a bunch of rules and the rules are never use an adverb if you don't have to uh always show instead of telling when you can avoid excessive dialogue tags if you use a dialogue tag try to use a a specific one when appropriate so you know you wouldn't say he said loudly say he shouted right you can include those examples I also have one that says don't use any of these words and it's a big list

of all the words AI loves to use are all the phrases right so Del is the One that most people know about but there's a ton of them and if you do you know the story behind delve I don't okay just quick I know the Paul Graham tweet is there a backstory to that yes so the reason that delve is used so much is that delve is very commonly used in Nigerian English okay and they were using Nigerians to train the AI so it has to do with the actual people who are working wow so

it did actually have something to do with Nigeria yeah that's Fascinating that's what I read that's what I read there's a bunch of those that the AI will do if you let it so AI loves it when you run your hand through your hair it loves uh musing right there's certain things that it always wants to say and so by just giving it a list of things it can't say it'll use other stuff and it'll be more varied but the key thing that you're saying here is you got to be really specific and what comes

out of the box Isn't good so you need to work with it yes and how did you work with it was there like a model that you Ed or were you just sort of playing around with it day in and day out so a lot of playing around with it a lot of talking with Nathan about it cuz he's been exploring this too the there's a Discord for this novel craft app where people share like prompting advice and so we get people get super nerdy about it in there and I've just spent a lot of

time playing With it but I also want to be clear that after spending tons of time working with it and getting it to a point where it's really good it's not really writing any of the book for me because what'll happen is I'll prompt it it'll spit out some text I might keep a sentence here or there but I end up deleting tweaking changing a lot of things but it's like close it's pretty close to how I would have done it but it won't do that for anybody else because they don't have my Writing sample

right like and this is where the sonnet versus Opus thing comes in is sonnet does a better job of following my style because I think it just takes the directions and it follows it and with how robustus prompt has gotten it does a damn good job sometimes and so maybe I don't need to change as much as I thought and the other thing that's interesting is there's there's also this like built into the tool and so you can chat with it about your Entire book or about a scene and you can say like you know

what are some other things that could happen after this scene or what would be some better surprises here and again 95% of the stuff isn't good and like what you would come up with is better but sometimes it has a pretty cool idea and that helps a lot with getting unstuck well there's another thing here that the brain is much better at reacting to something that already exists than coming up with Something in the first place totally so if you get get something even if you think it's trash it's actually easier to say no that's

a terrible idea wait why is that a terrible idea and now you've inspired something whereas if you're like hey just give me an idea now you're left musing on what am I going to come up with it's surprisingly helpful when it gives you a bad response because then you you suddenly immediately know what should happen and and when it gives you A good response and you tweak it like that's helpful too the analogy I've been using a lot with where I think AI writing is going is uh Miranda Priestley and The Devil Wears Prada because

you seen the movie yeah okay yeah like if you notice she never designs anything yes people bring her things and she says yes no right and I think that's where a lot of the like work writing with AI is going is you'll have a model that's very very well trained on your style and then Some of the time you'll just you know go at it because you you know exactly what you're going to say here but then whenever you get stuck you'll be able to just summon a bunch of ideas that are already in your

style and fit your taste that you can then go yes no on and it's not it's not going to replace you because it still needs you like if I let if I let it write the whole book the book would be ass it would be terrible but getting a few ideas along the way Has helped significantly with getting over writer block and with going back to the braiding I'm not very good at description like that's my big weakness right now is getting better at description and so I can take a chunk and I can say

I need a little bit more description here give me some ideas and it'll pop out a few sentences say I don't like that I don't like that I don't but I like this and if I combine it with this like now we have some Interesting stuff here now it's now my writing is better without it being replaced by it so that to me is so cool because it's sort of like for a while you could learn how to program just by going to stack Overflow and you would copy and paste stuff and your program would

work but you wouldn't really get it but you do that for long enough and you start to understand you start to learn by osmosis right like a kid never takes a language class they just learn By hearing people talk sure and if you let AI like provide things for you that are better in little ways than you could have done you slowly start to get better at summoning that yourself without having to ever have like read exactly like how to do it you're kind of closing the taste Gap by letting the AI tool suggest some

things that might be getting you a little bit closer uh in each of those tiny pieces yep yeah I think it it really for at least for a Certain period here your competitive Advantage with AI is going to be your taste so if you develop better and better taste in writing then you'll be able to use it so much more effectively than somebody who's just blindly following what it says yeah all right Nat that was fun that was fun congrats man you really you really moved into a new era of your writing and this conversation

was cool because we really got to see like how obsessively you've Been learning about stories and all that it's basically all I've done the last two years so it shows it's been great it shows congrats man thanks dude