On Deck Writing Fireside Chat: On Deep Work and Maintaining a Writing Habit
Chris Sparks was asked to speak to the most recent cohort of the On Deck Writing Fellowship (ODW) about how to master the mental game of writing, generating the state of mind necessary for different writing stages, and translating experiential inspiration into tangible artifacts.
Audio recording below (53m). Resources mentioned and full transcript following.
Resources mentioned:
Podcast Transcript
[Note: transcript edited slightly for clarity. First few minutes of conversation unavailable due to a technical difficulty.]
Chris: A really key driver is, if we can understand what drives us, we can recreate those conditions which allow our best selves to show up.
Tom: So I guess—do you think that's individualist—I want to hit on what drives individuals. Is that individualistic, is it by and large a few key things? In your experience and in your practice working with C-suite and investors and hedge fund managers and such, like what have you found is either commonplace, or do you think it's highly dependent on the individual, himself or herself?
Chris: It's a false dichotomy, for sure. I like to go for that barbell approach. So first, I do think there are conditions which tend to generalize across high performers. Happy to go into some of those today, particularly in a writing project context, as far as doing the work, doing the impossible, showing up, that type of thing. I also do think there's a little bit of a unique snowflake in each of us, and I think we are generally at heart deterministic creatures, in that our behavior is more or less determined by the context we put ourselves in. So when I work with a client, when I have a conversation with a friend, my mind is always looking for patterns. I think that patterns tend to repeat themselves unless something has changed to disrupt that pattern.
So, looking for positive patterns when this person has performed well, when they feel like things are leading in the right direction, they have a high trajectory, happy, fulfilled, all that good stuff. What were those conditions? And that's the cheat code of this: "Oh, you noticed that these things really work well for you. Why aren't you doing that now? What is something we can put in place to have that happen right now?" On the other side, when we notice, "Okay, writing habit falls off" or "Not feeling inspired" or you're throwing out things that you're putting down, what correlates with those conditions? Are there things that we can do to add friction to these flow inhibitors arising?
So that's why I call it the barbell approach: I do see these commonalities to doing hard things, to showing up, that seem to generalize across my clients from the sample size that I have, and that's the low-hanging fruit that I try to put into place. Try to intercept them through an experiment by, "Hey, try this, prove me wrong, see how it feels, be curious about that experience." But also just, what's worked? How can we make sure that happens more often? What hasn't worked? How can we make sure that happens less often?
Tom: That's absolutely fascinating. The idea that you're putting friction—you're not decreasing friction in order to get into the flow state, but you're increasing friction against those things that take you out of the flow state. What are—I mean, I think it's kind of obvious, but I'm interested if you've—what are some tools, strategies, processes, frameworks that you've used to keep your time writing sacred? Because I think there's a quote from Robert Caro, he said, "I keep nothing but my typewriter and paper and a pen and pad in the room, because writing is hard enough." What are some strategies that you've identified as a writer—because you've written some tremendous things that I've been fortunate enough to kind of converse with you about—where do you see that coming up in your own personal practice? And maybe you can extrapolate that part to me more generally.
[brief technical difficulty]
Chris: Hey. So I think what Robert Caro has to say there is very true, that I think all productivity—writing included—comes from constraints. So if we identify what we want to do, can we make that easier? If we identify what we don't want to do, can we make that harder? I think something that is under-appreciated about writing is that it requires many different states of mind. And so identifying what is the 'correct' state of mind for this stage that this piece is in? Do I need to be super, super oblique and open and playful and I should be thinking about things that I can do to elicit this sub-self who is very childlike, open, playful, explorative, curious, or am I getting towards the later stages of polish, and that's when the inner critic, the perfectionist has his time to shine?
But I think where myself and others have gone astray is that we don't match this state of mind for the current stage. Say this inner critic shows up when we're writing that really crappy first draft, rather than towards the later stages, or we are getting to the point where we are converging from idea generation to, "All right, let's start to make this more concise and cut out all the fluff," and we just start going down an internet research rabbit hole and thinking about all the adjacent ideas we could explore.
So I think at the principle layer, my expansion of what Robert Caro said—beyond tools, right? Everyone's heard, "If you're writing, don't have access to the internet, don't have anything at hand that you don't need for the task, make sure the room is quiet," all that sort of stuff. But I like to think particularly about which Chris needs to show up today, and what can I do to encourage this Chris to show up? When we were talking before this, Tom, I was making the comparison from poker to writing where poker, as you guys know, is sort of a zero-sum competitive mental combat, if you will, and that showing weakness to your opponent creates strength. That you know, your opponents feed off of that. And I think that is very true in a writing sense as well, when you think about the mental game of writing, that weakness becomes this recursive loop that leads to self-doubt and leads to you know, collapsing upon ourselves. So being able to be meta-cognitively aware—"Where am I at right now? What's my current mental state, and what's the mental state that I need to have?"
So, in poker I talk about this confident/critical continuum, where when I'm sitting down to play I want to be all the way on the confident side of the spectrum. Like, "I am the best poker player who ever lived, everything I touch turns to gold," type of thing, but as soon as I leave the table I go all of the way to the critical side, and I assume that I just did a bunch of things that were really bad, and now it's my job to figure out why I suck so much. But the important thing is that this is a mental superposition. Both of these states need to coexist inside of me, but it's my responsibility to determine when is the time to be extremely confident in what I'm writing—so it's like, am I in the generative phase? It's—I'm at a bar talking to someone who I believe to be—let's say they're five years younger than me and they just know nothing compared to me on the subject, and I can just write as if I know exactly what I'm talking about, and when I'm able to take a step back afterwards and say, "Well, which of this actually makes sense? Which of this is useful, interesting, et cetera?" But knowing what the right time is for each of those mental states.
So, that's what I come back to, is what allows these sub-selves to show up? In poker, it's a battle between players, but in writing, it's very much a battle between sub-selves. That any battle that occurs between people occurs within people. So if I continue this metaphor, for me writing is almost winning this battle against myself.
Tom: Goodness gracious, there's so much there to unpack I'm struggling where to begin. I would say your point about being able to shift from creator mindset to critical mindset, or confident mindset to critical mindset at the poker table in front of the computer, that's so much easier said than done. How do you even begin that process, because unfortunately, at least I don't possess that switch to be able to kind of shift my mental attention, acuity and whatnot, to different voices inside my head. How do you even begin to become aware of these voices and tune into them at the right place and the right time depending on what you wanna do?
Chris: Sure. I think there's two aspects to this. One, if we think about what's happening internally, it's, "Can I shift from the first-person perspective to the third-person perspective?" In behavioral science they refer to this as "the outside view," where rather than thinking about my own unique circumstances and situation, I'm approaching myself objectively. So exercises that I lead that are analogous to this is, that I imagine that I am reading a story of which I am the protagonist, and so as I do things, "Okay, he raises his hands," and I see this materializing on the page. And so it takes me into this view of, "I am reading about myself." And so what does it make sense for the protagonist to do next? Another one is I pretend that I have amnesia and I am like an alien beamed in from outer space, I've just landed in this weird meat suit, but, "Oh, this meat suit has some interesting skills," and what does it make sense to do next given this body that I've inherited? So just different mental frames or switches or playful exercises to get me out of this space of being super myopically focused on myself to just be a little bit more objective about, "What does it make sense to do next given where I am now?"
The second aspect of this I would come back to what I said before about the very helpful belief that free will, motivation, willpower are very limited, but that where I can exercise control over myself is in the sculpting of my context. That I think my environment is a container that my liquid personality conforms to, and so if I can do things to shift my context, such as I play different music, I change clothes, I go outside, I go to a different place in my apartment, I change browsers, I change computers, I have a conversation with my friend using a voice that's two octaves higher or two octaves lower, I change the lighting. All of these different things to signal to myself, "Something has changed," where if I change my context I shift my mindset. That there's a bit of a feedback loop that happens there. I can either approach it from the side of I meta-cognitively realize that where I'm at right now is not where I want to be, that a lot of this Jedi mind-trick of awareness: "Where I am I right now, where does that compare to where I need to be?" And then just trying a bunch of things to shift that, where as I change things it naturally shifts. So that like, stuckness is almost a physical manifestation of being stuck in the same place in the same context.
Tom: Goodness. The questions are starting to trickle in, and they're—I know. Sabrina, literally. I mean it's like, cool. I don't know if you see the Zoom Chat, Chris, but people are like, "Oh my god, truth bomb after truth bomb." But Sabrina, please go ahead. I feel like your question is a perfect follow-up to what Chris is talking about with meta-cognition and being aware of sub-selves.
Sabrina: Yeah, sure. Thanks for being here, Chris. It's like a quote book coming out of you right now, so I'm scribbling to get the notes down. So my question was kind of just around like, how are you able to turn those voices off, I guess? When you're—I feel that transition period between mindsets can be like just a weird place, so I'd just love to hear you talk about that.
Chris: I was—I'm debating whether turning them off is the right thing. I tend to think that innovation occurs at the intersections, so that these different voices (if you continue that metaphor) are bringing different perspectives to the same problem. So especially when I'm in the generative phase, which is—say, if I'm writing a piece, I try to spend most of it within that generative phase. It's hard to get to the point of having too many perspectives. I think that the turning off is more I realize that I've hit diminishing returns from one perspective and want to try to create a shift, but I don't know. Maybe—I can only speak from personal experience where you know, my internal narrator is always going. I do find mindfulness, meditation to be very helpful for bringing me back into the "present moment" by engaging my senses, so that could be one answer. It's like, I take a sip of tea and I think about how delicious the tea tastes and what temperature is and that sort of stuff.
But more or less, it's just trying to run with whatever the situation is giving me and trying to trust the process, that whatever is coming up is going to be useful in some form, whether it makes it into this piece or is the subtext which allows the piece to flow. I'm not sure, but I do find it helpful that I not—just that we try not to self-edit. I just trust anything that comes up is coming up for a reason.
Sabrina: Right.
Chris: Yeah, that's my perspective.
Sabrina: Yeah. I love that, the idea of trusting the voices to be—you know, even if it's not useful right now. Thanks for that.
Tom: So, Chris. Just to clarify, you're not making a call, like, "Hey, this is good, this is bad, this ugly" idea, in the generative phase. You're getting it all out there, putting it all on the page of like, "Hey, I'm not sifting through, I'm not like basically saying anything about these things. I'm just producing them, full stop." Is that correct?
Chris: When I am—that is the aspirational state, yes. I'm not going to say here on this mic that that's something that I'm able to embody all the time, but yeah, that is the intentionality behind it. I historically suffered from just crippling perfectionism, and every word that came out of my mouth onto the page was not good enough and was not explained well enough, not concise, not clear, all that sort of stuff. And I just try to err on the opposite extreme, especially when I'm in that generative phase, that treating everything that comes out as useful and great, because there'll be plenty of time for that critic to come out later.
Tom: Goodness. That's so well-said. Najla has a question about the timing of these things. I think macroscopically, this is easy to do over a sustained period of time, but when life gets in the way it can be difficult. So Najla, I'd love you to come off mute, if you're able, and ask your question.
Najla: Thank you Tom, and thank you so much, Chris. One thing I realized this year was that mastering mindsets equals mastering life. So it's a perfect topic. I do struggle a lot with not utilizing these shorter slots of time that I have. Sometimes they're the only slots that I have in the day to produce anything that is creative, and by that time I'm just so drained or just so unfocused that I just pick up my phone, and you know where it goes. So do you have any insights on how to quickly focus in that shorter period? I know there's Pomodoro, and all of that techniques, but with mindsets it's way different.
Chris: Yes. So first, having more time is better. I personally try to write between sixty and ninety minutes every morning, and whenever possible. I'm not always able to stick to it, but the intention is to do this input free. So, before I've checked my phone, before I've checked email, ideally even before I've talked to another human, is I believe that I've been dreaming about this, that my subconscious has been working on it, and so I just want to kind of verbal diarrhea onto the page anything that might have come up. Sorry for the gross analogy, but that's kind of how I think about it. But I realize that this is not realistic for everyone, and hey, when thirty minutes comes up, let's use that thirty minutes. And the best thing that I have found is to have some sort of ritual that gets myself into state.
So I'll give the example of what I do before I sit down to play poker. A lot of times, poker is very much on call, where I get a message or a notification that someone that I like to play with is on, and I have a minute or less in order to get myself from, "Hey, I'm hanging out with my friends, chilling out," to, "All right, I'm mental combat mode now." And so having these different steps where running through them gets me in there. So I do some breathing exercises, I put on a playlist, I'm thinking about my intentionality for this next phrase. Just a few steps that I can run through in sixty seconds that as I run through this, progressively get me to this point of like deep focus. And the science on this is really, really clear that what goes into your ritual does not matter. Like all this stuff of, "Hey, great habits of writers," like it doesn't matter specifically what they do, how many cigarette butts they have in their ashtray, how they make their coffee, that type of stuff. It's that you are doing something that signals to yourself, "This is time for focus, this is important, this is worth getting up to this level of performance."
So I would script that out for yourself. So you have thirty minutes, how do you spend that first minute? This is classic Abe Lincoln: "If you have an hour to chop a tree, spend some time sharpening the axe." What is it that you do that allows your best self to show up? Can you compress that into a one-minute period?
The final thing that I will say is I think preparation needs to happen in advance. It's kind of in the definition, but so often I will say, "Okay, time to write," and then it's, "Okay, my clock has started. Well, what should I write about today?" And I'm like, "Well, let's hop onto the internet and see things that I should write about," or, "Let me look at my list of topics." And I like to say—just across everything—is its important to separate planning from execution. If you know you're going to have limited time to write and that your inclination, just like everyone else's, is like, "Oh, thirty minutes, that's not even enough time, I'm just gonna send some emails instead," decide in advance how you're going to use that time. Like, what is something that you can reasonably accomplish within that thirty minutes? Maybe it's, okay, "Minute two, I'm going to open up my outline and I'm going to try to get it to this point," or, "Minute two, I'm gonna focus on these three paragraphs and really try to tighten them." But have that intentionality ticked in advance before you sit down. I think that is the most critical element.
Tom: That's an incredible, incredible answer. I think, Martin, you have some question about like the influence of philosophy on poker and writing. I would love to cede the mic to you.
Martin: Oh yeah, hey. Hi, Chris. Thanks for this. And I've written a little bit about the poker and business decision things to. I play with Phil Gordon and Jason and—
Chris: Oh, oh yeah. I would love to join you guys. Phil's the man, big fan of Jason. Must be a good game.
Martin: Yeah, yeah, good game. It is. I also like Annie Duke's talking about this kind of thing. So my question is, you know, you've talked a lot about poker and how it can help writing. Are there any philosophies that you have found helpful that have either reinforced or helped the poker thinking? Personally I've found some stoicism stuff to be incredibly applicable, but I was wondering if there are any other areas that you've gotten wisdom out of that help you with this. Thanks.
Chris: Oooh. This is where it gets fun. Yes, of course I love stoicism as well, where I have been—and this is just like my shoutout for a kind of Talebian Lindy Rule, where the longer something has been around the longer it will be around—So I, whenever possible, try to avoid reading new things. Of course, you know, if anyone here writes something, I'm very excited to read it. But if it's come out in the last year, I assume it won't be around one year from now, so I'm always biased towards reading things that are old, that have stood the test of time. And I think ancient philosophy that has lasted a thousand-plus years likely will be applicable for a thousand-plus years. There's a lot of compression that has happened there.
One that I have been thinking about a lot—so, brace with me as I try to articulate it, 'cause it's still kind of germinating in my mind—I think in the West we tend to think about things in terms of cause and effect. I do something and something else happens, I start writing and words appear. And I am more inclined to think about things in more Eastern terms, as articulated by some of the strategic philosophers: Sun Tzu, Tao Te Ching, most recently John Boyd, who's kind of done the equivalent, you know, bringing Buddhism to the West, of bringing this philosophy, the Sun Tzu type stuff to the West. And the difference about that approach is that conditions lead to consequences. That it is not, "We are doing something and then there is an effect," it's that these conditions emerge from a complex system and based off of these conditions, emerging things happen. And so the correct approach is to be aware, what are the conditions which are most beneficial for the consequences that I'm looking for, can I recognize when these conditions are emerging and be ready to take action?
A key takeaway from this is, most of the time the right action is no action. Not waiting, but being aware, ready for those conditions to emerge. I do think that's something that a equal and opposite approach to the butt in chair same time every day, which I think is very, very correct, is also you never know when inspiration strikes. A conversation with a friend, you're in the shower, you're on a long walk, and you're like, "Man, that is such a really good idea." Knowing that, being able to recognize it and capture it, and convert it into some form that you can use later. Where Tom was talking about tools, and you have the two sides, where—I'm very big on analog and carrying around the notebook and being able to just jot down some notes in my bad handwriting. It's like, optimizing for capture, 'cause I never know when that breakthrough is going to happen.
This is where Richard Feynman has this quote of, he keeps his twelve favorite problems in mind at all times. The pieces that I'm working on, everything that I'm looking at is a potential breakthrough on that piece, that focuses seeing my object of focus in everything. Right now, I'm writing a piece on simulation, and so I'm trying to work simulation into conversations, I'm trying to predict things and seeing how many predictions come true. It's like this overtraining, that all the time I'm looking for inspiration that can be transmuted into this piece. But the nature of a notepad is, "Hey, what are these little scribbles, how do they translate into actual writing?" There needs to be a point that I sweep these notes and turn them into some intelligible form. So I think—again, I go back to this barbell approach, and I need to both have this butt-in-chair deep focus, like, just get some words out, let's try to get this into some intelligible form, but also that my best ideas aren't going to come to me when I'm sitting at my desk, and so I need some way to get those out of my head and onto a page before I can get them into an article.
So this has been the most influential philosophy on me recently, is that like, conditions lead to consequences. So both what are the conditions that I want to create, but also being aware what these conditions are so that I can recognize them even if I didn't create them.
Tom: Phenomenal. Absolute—I mean literally it's a quote book, Chris. I wish I had my pen and paper here at the base of the mountain, 'cause I'd be scribbling down half of what you're saying. Goodness. Thank god we're recording, I'll just say that.
Chris: Yes.
Tom: There is another question, Harris has a question on goals and attaining goals, and this is interesting, I think, because I think you're a big systems guy as opposed to a goals guy, so I'm interested in your thoughts on this, but Harris, please don't let me butcher the question.
Harris: No, I think you nailed it. I mean, I think it's just a pretty general question, I'd just like to hear, yeah, how you think about goals. And I think, Tom, particularly relative to systems is a great call out. I think writing I think for me is kind of like I would say a particular type of like goal mindfuck, you know, where it's very different from like—professionally, I'm a product manager at a tech company, right, and the way you think about that work versus something like writing, you know, outputs versus inputs is maybe one way. So that's just adding some things, but would love to just hear any thoughts you've got on that.
Chris: Yeah, this is where I can't help but make a little plug. I have a workbook called Experiment Without Limits that's free to download, forcingfunction.com/workbook, and there's a chapter in there on goals that kind of lays out my philosophy and how I apply it. I also did a recent workshop that's available for free online called, "How To Achieve Ambitious Goals" where I lay out my framework. I'll see if I can drop those links into the chat. While I'm pulling that up—so I think that, again, a lot of dichotomies are false dichotomies. So there's this, "Okay, which is better, goals or systems?" Or, "Which should I use, input our output goals?" And my answer is always, "Both." Like, they both mutually support each other, so when you're thinking about goals first, like tracking inputs—How much time am I spending writing? How many words have I written? These types of inputs, it's—presumably if I spend enough time and write enough words I will end up with a piece. And so I say if someone isn't hitting the goals they'd like to have with writing, they're not publishing enough, their pieces aren't good enough, it always starts with, "Are you putting in your inputs? Is your butt in chair long enough, are you putting enough words onto the screen?"
But why we track outputs is very often—I would say the vast majority of the time, they're like, "No, I'm not actually prioritizing writing. If you look at my schedule, it's not a priority for me, I'm not putting in the requisite time, or I'm sitting down to write and doing lots of things that are justifiable as writing which are really kind of clicking around and shifting around words." But that other twenty percent of the time when someone's like, "Well, yeah, I wanted to write five hours a week, I'm actually writing six, I'm trying to get five hundred words a day and I'm actually at four thousand words a week, but I'm still not having the results I have." And obviously we deconstruct results. Is it tracking based on newsletter subscribers, is it based off of feedback from your mom? Who knows what that is? But that's when you get into tracking these metrics, these outputs. It's like, you're putting in the work, but presumably the time you're spending or those activities you're doing aren't leading you towards that outcome that you want. And that's where deconstructing how that time is spent—Is there a more direct path towards where you're looking to go towards? That's where it gets a little bit more nuanced: if you're putting in the inputs but you aren't getting the outputs you're looking for, clearly something is wrong with the approach and something needs to change with that approach.
So I think this applies to every goal—"Hey, you improve what you measure"—but it's important to both measure what am I doing that under my control and what is happening based off of what I'm doing. So, yeah. I don't think it's an either/or, I think it's a both.
Harris: Awesome. I love that. Thanks, guys.
Tom: Now handing it over to Alice. Alice, your question. Lemme just get it up. It's fascinating. About the pattern—recognizing patterns in your conditions in order to get you to start new frames of mind. Alice.
Alice: Yeah.
Tom: Would love to have you unmute.
Alice: Sure. Can you hear me?
Chris: Yes.
Tom: Good to go.
Alice: Oh, cool. Well, thanks, Chris. This is fascinating. So my question is, earlier you were talking about recognizing the pattern or condition of something. Either someone or something, and try to recreate a context that framed the liquid mindset. Right? The whole word itself is a quote. So my question is, how—Can you explain in more detail how you do that, or is there an approach we could repetitively do that? And if we do that, the follow-up question is, is there a diminishing return if we repetitively recreate the context or condition, or is it evergreen?
Chris: Yeah, great question. I think this is both tactical and philosophical. So, first the tactical approach, I think I would tag off of Harris's question, in that we need to be tracking. So the metric here varies based upon what your goals are, but I like to have something that's quantitative and something that's very qualitative. So one that I like a lot, that's super simple, is at the end of the day, was today a one or today a ten, or somewhere in the middle? Just ranking the day one through ten. And that could be, you know, was it productive? Was it meaningful? Was it purposeful? Do I feel happy? I've also had ways that I get randomly sampled throughout the day to try to identify what correlates with feeling happy, with feeling fulfilled, with feeling high energy, these types of things. And I find that having these queries, how am I feeling right now, how are things going, one to ten is the first step. That just like you don't know where a particle is until it's observed, you don't know how things are going until you ask yourself. So that's why I think it starts as just, you know, one to ten, how's it going?
And then once you have that measure you can start to identify correlations. So one for me that I always like to share is I identified, "Hey, if I go outside, on average I rate the day two points higher." So I can go from a six to an eight just by stepping out my front door, and it just blew me away how often that wouldn't be the case. I think you can tell by my skin tone that I'm still working on that. But it's the only way I was able to identify some of these correlations, is like, "All right, today was a really good day. What happened that was different today? Maybe this is something I'd like to try again tomorrow and see if the pattern holds." Or the opposite, "Man, I sat down today to write, and not only did nothing come out but I felt terrible that nothing came out. Is there anything that happened that might have caused this? Maybe I'm low on sleep or maybe I got in a fight with a close friend or a family member, or maybe I'm just not feeling all that inspired about what I'm writing about. Maybe it's time to switch to one of the other pieces in progress."
Try to identify, hey, what is one of those conditions that is true? That's why I like this experimental framing, is it shifts from, "I'm being judgmental, I suck as a writer, I'm never gonna get good at this, maybe today's not my day" type stuff to being very curious. It's like, "Oh, that's interesting that I sat down to write and no words came out. Why might that be the case? Is there anything that I can learn from this experience that maybe could be useful to others, or useful towards creating better conditions in the future?" That shift from judgmental to curious on a mental game point of view is just so instrumental for me.
But more philosophically, if I wasn't being philosophical enough already—
Alice: You are. Great—
Chris: Pattern-wise, it's very possible to hit diminishing returns, but I'm trying to think about if I have this minimum viable structure in place. Right? I wake up, I do some things that get myself into that state. I'll throw a few out there. I journal, I love morning pages, I meditate, I do some stretches, I do some voice exercises, get my voice going. Like, I do these things, I put my butt in the chair, I open up the blank document, start typing. That minimum structure, once that's been in place, I think I just try to create a lot of magic in the middle. It's having that—I think that a lot of creatives that I've worked with think everything needs to be messy. And it's like, you can have this structure as a bookend, right, before and after you sit down to create your art that allows you to be maximally messy and explorative in the middle.
So philosophically, I'm trying to be very deliberate about the things that I know that work, but then once the gates are open, like let hell break loose sort of thing. Once I'm in there, I'm super curious, not judgmental. I don't know if that's the answer you're looking for, but that's what comes up for me.
Alice: That, no. Thank you so much, I love the approach of minimal viable product and then be curious, let the magic happen. Thank you so much.
Chris: Thank you. Yeah, I come back to that everything is a practice, right? Like meditation, for example, is not something I'm an expert in, but something I'm very much interested in exploring for the rest of my life. Hey, if I can understand myself, control my emotions a little bit better, maybe approach this thing that some others call enlightenment, that's worth pursuing the rest of my life. But that, man, if I thought about it as, "Oh, I just sit down at a cushion and breathe," oh man. That sounds so boring. But if I engage my curiosity, right, that there's infinite depth to this experience, it's like, well, how does it feel right now? What's different today? What's going on, that if I can just pay more attention then there's magic in everything. There's magic in doing the dishes, there's magic in you know, editing a piece. Like, trying to find where I'm using the passive voice. I find that mindset, that frame that we bring to what we do is so powerful.
Alice: Thank you again.
Tom: Love that. Yeah, I'm not even going to introduce the questions, 'cause one, they're so good, and two there are so many. So, Sujatha, would love to cede the floor to you.
Sujatha: Chris, what a great conversation. You're bringing the magic in right there. I have a question, it's kind of based on what you wrote, you said life is the product of your bets. Right? So how do you know that you're making the right bets? And I'm thinking of two things here. One is the sunk cost fallacy, right? You've put in so much time, when do you know it's the right time to walk away, combined with what you said today about the voice of confidence in your head. How do you put those two together, and when is the right time to say, "This is not working. I'm confident, but it's not working."
Chris: Yeah. So life is a product of your bets, this is a key takeaway from me from poker, is a lot of people think of poker as gambling, but really it's just making lots of decisions with imperfect information. And it made me realize that everything we do is a bet. You have bets of differing sizes. So our largest bets, what do we choose to study, what career path do we pursue, who do we choose to spend our life with, where do we live, these types of things. But the small bets as far as like, "Do I drive or take an Uber? Do I have chamomile tea or peppermint?" All of these things are bets, small or big, and we make some sort of investment or choice where we expect the returns are going to be greater than the cost, adjusting for risk. That the more we learn about perception, the more we realize that all of perception is a bet. We are not seeing the world as it is, we are seeing the world as we think it is. And our sensory information confirms or denies that prediction.
So my takeaway from that—you can see how I'm practicing my future article on you guys—is that we are prediction machines, and that all the time we are predicting. Whether we know it or not, we're always making bets. And so I think the meta-skill is to be calibrating our bets. So for example I'm—I'll use a personal example, where I'm at a party and I'm getting self-conscious and feeling awkward, and I say something that is trying to stroke my ego and sound important and be high status, and I'm like, before I say this, "Oh, everyone's going to think that I'm going to be really cool how I'm talking about this thing that I'm doing." "Oh, I have a personal assistant," or, "Oh, I have a company." And then the second it comes out of my mouth, it's like, "Oh, that's not a very good prediction." People took that to be like, "Oh, this guy is a little bit insecure right now." And I'm like, okay, maybe next time—what was the information that I missed? My bet here was incorrect. There's something presumably wrong about my process or what I'm paying attention to. Assuming this situation is going to come up again and again, what can I do differently next time? How can I make a better bet?
So where I think a lot of people go wrong is that these bets become so subconscious and ubiquitous that we forget we're even making them. And so we make a bet and we say, "Well, how did that go? How could they have got better? What am I going to do differently next time?" We apply this in a writing context: we sit down to write betting that this use of time, even though there are no immediate returns, is going to lead us to where we want to go in our career, it's going to improve our thinking, all this type of stuff. And afterward, after the session, ask yourself, "How did that go? How could that have gone better? What could I have done differently before I sat down to maybe have better results?" And then test that assumption, calibrate it. I think that's the ongoing process, is just improving your ability to bet. You predict what's going to happen, you experiment, you take action, and then you reflect. How did that go? How could that have gone better?
Sujatha: Fabulous. Thank you.
Tom: Last but certainly not least, we have Zara. Zara, please, if you could come off mute and ask your question. And I feel like I've planted you—we've come full-circle now back to poker, per Zara's question. Zara, are you there?
Chris: Great.
Zara: Can you hear me, guys?
Tom: Zara, not really. It's pretty choppy. Could you try to—or do you want me to just read it? If so, you can just say so in the chat.
Chris: I can see the question. So—
Tom: I'll just read it, Zara. Oh, all right, perfect, 'cause you're in the Slack, Chris. So, yeah. Go for it.
Chris: So Zara's question is, "What is a lesson in poker that you notice is applicable to decision-making in real life?" So one I shared is just that we are always making bets, and so to become conscious of the bets that we are making, and after we've made a bet say, "Hey, can we make a better bet next time, because these situations will recur." The key mental model is like—someone asks, "What's the biggest lesson you take away from poker?" It's this concept of expected value, which is very related. Expected value is the outcome, how good or bad something is, multiplied by how often that thing happens. So it's like, we do something and there's this branching decision tree, and some of these branches are good either immediately or down the line because they lead to other good paths. And the same thing, I'm trying to prune off these branches of the tree that lead to bad hypothetical universes that I don't want.
And thinking about things in expected value terms, these are my two levers: I can either go after things that are very high-probability to go well, or I can go after things that, if they go well, have massive upside. Maybe they're a little bit more convex or asymmetric. I'm constantly playing with, "Do I want something that is a guaranteed win, or am I going after something that is really huge, with a 10x type outcome?" Everything we do has a certain expected value. We live in this probabilistic universe, and so being able to calibrate to estimate these probabilities and what's going to happen allows us to make better decisions. I think that everyone without this poker background can fall into this trap of thinking in very black-or-white, all-or-nothing type terms. Being very results-oriented: "I did this thing and this thing didn't go well, thus I'm not going to do that thing again." That a bad result is the effect of a bad decision. Or, "Hey, I did really well on this date today, I'm great. I must have done really well."
You know, not being aware that there's so much luck and noise in everything that happens that if we examine our decision process—What did we do? What was in our control? What did we have in mind when we were doing this? Versus there's always room for improvement. That instead of patting ourselves on the back every time something goes well, think, "Cool, that went well, how could it have gone even better?" But also not taking it personally, not being judgmental when things don't go well, because a lot of life is outside of our own control. We take it as an opportunity to go, "Cool, that could have gone better, oh well. What did I miss? Maybe what would I like to do next time?” And so this expected value framework I find very helpful for determining what's in our control and what we are optimizing for.
I'll give one more plug. I have this exercise on my website called "Expected Value Calculator" that I use for making all my major decisions. So things like—I've done this for what am I going to write about next, for where am I going to live, what marketing channel am I going to use, this type of stuff. And the spoiler alert on this exercise is someone thinks that they're trying to do apples-to-oranges comparisons between these different options, but really it's just an experiment on yourself to see what value is most important to you. And I think that that's the key of this Expected Value Calculator: whatever value you decide you're optimizing for determines whatever option is best. So I think that that's the kind of key takeaway, is it comes back to your inputs of like, "What's a good outcome? What can you do in your power to optimize towards that?"
Tom: Chris, you're a gentleman, genius, guru. So I think you've dropped your site. Where can people find you? How can they get in touch with you? I know you're in the Slack, but yeah, how can people converse with you further if they'd like to?
Chris: Yeah, this was fun, guys. Thanks for letting me talk and share some ideas. I'm glad some things were useful. Hopefully, some things that translate to the practice of writing. You know, trust the process, stick with it. My company is Forcing Function. That's forcingfunction.com. I have a few articles on there as well as some templates and resources on how to get more done, live a better life. The first place that I always point people to if you wanna dive deeper into this is the workbook that I created, Experiment Without Limits. That's free to download, forcingfunction.com/workbook. Happy to continue the conversation offline. I'm in the ODW, On Deck Writers slack. Feel free to PM me there. I'm also occasionally active on Twitter, depending on what mood that I'm in. You can PM me there as well. My handle is @SparksRemarks.
Tom: Amazing. And Natasha was literally, as you were saying them, dropping them all in the chat. So thank you, Natasha, for serving as scribe.
Chris: Yeah.
Tom: But can we all just one final time come off mute and give Chris a round of applause? I think honestly it's not an exaggeration to say that every other sentence was quotable and remarkably insightful, Chris, so thanks for spending some time with us on this Friday.
Chris: Thank you. Pay it forward.
Alice: Thank you.
Harris: Thanks, Chris.
Chris: Appreciate it, you guys. Thanks for showing up on a Friday morning for your great questions. I feel really inspired. I'm gonna do some writing myself, I think.
Tom: Amen. Let's get after it. Thanks, everybody. Have a great Friday and weekend.
Chris: Great meeting you guys. See you!