Deep Questions with Cal Newport - Ep. 30: Habit Tune-Up: Easing into Time Blocks, Planning Big Goals, and the Story of How I Sold My First Book

Episode Date: September 24, 2020

In this mini-episode, I answer audio questions from listeners asking for advice about how best to tune-up their productivity and work habits in a moment of increased distraction and disruption.You can submit your own audio questions at speakpipe.com/calnewport.Here are the topics we cover: * Easing into time block planning. [6:24]* Keeping up when taking notes. [11:49]* Optimal delay between learning and recall. [17:12]* Planning big goals. [20:59]* Insider advice on book publishing [29:36]Special thanks to our sponsor Grammarly. For 20% off Grammarly Premium go to Grammarly.com/DEEP.  Use your laptop or desktop (this link doesn't always work on phones).As always, if you enjoy the podcast, please considering subscribing or leaving a rating/review.Thanks to listener Jay Kerstens for the intro music. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

In the August 23rd podcast, you said doing halfway time block planning is worse than doing none at all. I wonder how this applies to building a time block planning habit from scratch, which is something I'm trying to do. I'm Cal Newport, and this is a deep questions, habit tune-up mini-episode. In this format, I answer audio questions on the narrow topic of tuning up your productivity habits it's in this period in which our professional lives are increasingly disrupted. Before we get rolling with today's questions, there's something I noticed recently, and by I noticed, I mean, my wife pointed it out, that I thought was worth bringing up. When I do weekly planning, I get stressed out and cranky.

Not fun to be around. I've really began to try to understand why, and I have a theory that I think is interesting, because I'm not sure if other people suffer from the same issue. When I do weekly planning, what I am doing is confronting everything on my plate for the week. Here's the meetings that are scheduled, the classes, the lectures, all the household things, the child care, the homeschooling, everything on my plate. Then you start looking at projects you want to make progress on, deadlines that are coming up, task, small task.

These ones really do have to get done this week. Let me highlight them. And you have all these chest pieces. And like I say, you have to move these chest pieces around on the metaphorical chess board that represents your available time and attention for the week. And this process, surprisingly, gets me quite stressed out and cranky. And what I realize is that what's going on here is that our brain, our Paleolithic brain, is not well suited for this type of batch planning.

So even though you know in your prefrontal cortex when you're doing weekly planning that this is not stuff that has to be done right now. This is not stuff that is all urgent and needs to be done before you go to sleep tonight. You know you're looking at a longer-term time horizon. But some deeper executive functioning piece of your Paleolithic brain does not get that

And it just seems like a lot, because on the scale of a day, of the scale of the time that is immediately before me, what you confront when you do weekly planning is way too much. And so this is what I realized. It is pressing these Paleolithic buttons. When I confront all this stuff, I'm like, this is too much stuff, too many people want my time, I have too much going on, there's not enough time, and it's just a fundamental mismatch between the mechanism that we have been granted through evolution. for thinking about planning and execution and what is required to actually keep up with the complicated but urgent workloads of modern life.

Now, almost always by a time I'm about two days in, I feel much better because you have expanded that time horizon. You've gotten a bunch of things done. You're making progress. You're no longer being confronted with all these obligations fresh and your mind is better able to understand, oh, this is a plan for five whole days. And that's a lot of time. And I've already gotten a lot of it done and we should be fine. But in that moment when you're first confronting it, it seems like there's too much. Anyways, I don't know if you have that same sensation, but I thought I would point it out in case anyone else is suffering from it. That reaction of stress and crankiness that comes when you do your plan is artificial. It does not necessarily

recommend anything bad about your week. It does not necessarily indicate that your week is impossibly overloaded. It's just a mismatch between a Paleolithic brain and a highly connected over-scheduled modern lifestyle. Now I point that out because if you don't know that, it may dissuade you from continuing with a weekly planning habit, but I really do think that's crucial. So just sort of ignore that momentary stress. Follow my lead and don't be near family members while you do your planning

because they don't want to see you cranky and it should all be okay. So anyways, a little self-observation I had that I thought would be interesting to share with you. We got a lot of good questions in the show today. Let me remind you if you want to contribute your own audio questions for the Habit Tunedut mini episodes, you can do so at speakpipe.com slash Calnewport. You can record it right from your browser. It's quite easy.

That's speakpipe.com slash Cal Newport. And I, of course, appreciate all those questions. I also appreciate ratings. I also appreciate subscriptions. and I also appreciate reviews that all help spread the word. With that in mind, let's do our Spotlight review for this episode. It's a real five-star review from iTunes. Now, the title here got alighted, the title of this review,

but I'm very excited about what it might actually be, so I'm going to fill in those blanks. The title I see here on iTunes for this five-star review from Cooley 90 reads, like having a friend who is the Chuck in dot, dot, dot, dot. Now I'm going to assume that goes on to say Chuck Norris. I'm going to assume it says to Chuck Norris of productivity because that would be awesome. Something that I think for sure I am going to put as a blurb on the front cover of my next book, The Chuck Norris of Productivity, Dash Cooley 90, comma, iTunes review.

Five stars. So I'm very excited about that. Here's what the rest of the review reads. I only must listen to podcast. Cal is like having an encouraging friend who wants you to be your best. Add years to your life and life to your years by listening to and reading Cal Newport. Thanks, Cal. Keep up the meaningful work.

Well, thank you, Cooley, 90 for that spotlight review. All such reviews are appreciated. All right. Let's get rolling with the first question in today's episode and get in the productivity geekish weeds. with a question on time blocking. Hi, Cal, this is Duncan. I work in software development,

and I have a question about time block planning. In the August 23rd podcast, you said doing halfway time block planning is worse than doing none at all. I wonder how this applies to building a time block planning habit from scratch, which is something I'm trying to do. For example, do you think it's appropriate to start with only a few short time blocks per day rather than planning the whole workday? the same way you suggest building up focus muscles by starting small and gradually increasing the length of a focus session.

Thanks for your help. So, Duncan, the challenge as I see it is that you want to get your brain used to the idea of intentionality. That is that what you were doing at work at any given moment is pre-planned. You want to move away from the list reactive approach to time management in which you sort of just answer emails, answer Slack, and occasionally try to make progress. At the same time, you are trying not to set up, if I'm understanding your question correctly, an ambitious enough time-blocking discipline that you're likely to fail. So we have two competing concerns.

You want to get your brain used to having intentional allocations of time, but you don't want to be so focused in those efforts that you fail and you give up and go back to doing nothing at all. I do not think that the correct answer is to time block part of the day and then leave the rest of the day reactive. Because you're going to be working at counterpurposes, that reaction half of your day, that reactive half of your day is going to be undoing that exposure you got in the first half of the day to intentionality. Once you switch to a time block planning mindset, you really want to start moving away almost completely from any of your professional time being. unallocated. You want to lose your taste for that approach to working. So what's the solution? I think you should start with, the right way, in other words, to ease in the time block planning,

is with much rougher granularity blocks. So not less time, but less precision with the time that you block. So I'm talking, you know, big three-hour block of just catch-up on tasks or two-hour block on, you know, program, because I know you're a software developer. Or, you know, put an hour long email administrative block at 11 and an hour long email administrative block at 2 and just mark the rest of the time work on software. You know what I'm saying? So you're in a mindset of I'm allocating my time. I never am just freestyle reacting to things and doing emails. I'm in control of my time, but you're making your granularity these blocks so rough and so easy to follow that you're not straining yourself, that you're not likely to fail. That's how I would

get started. Rough blocks, not abbreviated time blocks. The thing I would throw in there, this is the technical gloss, put in one or two very precise blocks just to get in that habit. So maybe you have this very crude day, like email, program, generic. to-do's to end today, right? Something you know you're going to keep up. But then put in somewhere in there one 30-minute block that has you do something specific, important, but non-urgent. Just one. Now what you're practicing is getting that habit of, you know, when my time block schedule says it's time to move on to this other thing, even if I do not feel in the moment either motivation or urgency to do it, I switch.

Now that's the hard part of time block planning. That's the mindset that takes some training. So if you fill your schedule with this, you might fail at first. But if you have just one thing, your goal is to hit that one non-urgent but important task. To hit that one small block, you're slowly building up that muscle without having to do too much of a lift or having too much of a threat of your time block schedule discipline just collapsing. So if you're doing this, very rough, easy to follow granularity blocks that are very easy to fix with just one very precise non-urgent, important task block thrown in there.

Do that for a while, let's say three to four weeks. I think you will have those cognitive muscles exactly at the strength you need them to be to actually then shift into a more serious time block planning discipline in which you're more precise with your blocks and you're able to start mixing in the background, the urgent, and the non-urgent in much more optimal configuration. So that's a good question, Duncan. It's one we haven't tackled before. And you are, I should add, getting into this habit at just the right time because of my impending November release of the long-awaited time block planner, which I will be talking about more. But soon you will be able to

have a beautiful physical aesthetic object you can hold to remind yourself that you take time blocking seriously. So keep the practice up now so that when that planner gets out in November, you'll be ready to use it with purpose. All right, let's take a quick diversion over to some student questions. Hi, Cal, my name is Gabby and I'm a current senior in college. I'm reading your How to Be a Straight A student, and I was wondering if you have any updates to your note-taking strategy. I'm trying to use your question evidence conclusion strategy,

but it is a bit hard to do it during a fast-paced lecture, So I was wondering if you have any tips on how to adapt that, perhaps maybe redoing my notes after lecture. So for the uninitiated, when Gabby mentions question evidence, conclusion, note taking, she's referencing a format I talk about in how to become a straight-a student for taking notes on non-technical classes. And essentially, I suggest that you organize all the information that you, you hear in lecture and read in relevant textbooks into a format where you have a question,

a conclusion to that question, and then a whole list of bullet points of evidence in between that brings you to that conclusion to that question. For lots of various cognitive content-related reasons, this is a very effective way to take loose bits of information in a sort of humanities or liberal arts context and organize them in such a way that you can deploy it. in a synthesized theoretical style framework that's going to be useful for test or essays or papers. So as Gabby noted, she was having a hard time actually keeping up when she was trying to take these types of notes in class. As she was trying to capture information from her professor, getting them organized into coherent question, evidence, conclusion, clusters on the fly. Gabby, that's common.

Your suggested solution of needing to do some work after class, I think, is to write one. I talk about this a little bit in the book, but basically when you're in class, it can sometimes be like rapid fire. This stuff is coming, you're trying to capture it. And what I recommend is that to the degree you're able to during lulls in the lecture, the professor is doing an aside. Someone is asking a question you don't care about. Take advantage of those lulls to go back and try to organize a little bit more what you just recorded. To come up with a tentative question. To come up with a tentative conclusion.

to try to break apart a partition some of the information you have into distinct question-evident conclusion clusters. That helps. Often you need to spend some more time doing this organization after class. The key here is to do this organization as soon as possible when the class is over. If it's possible to do it immediately following your class, that is the best time to do it while it's still fresh. If not, do it later that same day while it's still somewhat fresh in your mind.

Until those notes are organized to coherent clusters of that format, consider those notes not yet done. Consider your day's obligation towards that class not yet complete. Being there in the lecture hall was the first piece, completing your notes was the second piece. To make this tractable, you want to eliminate as much friction as possible. So resist the urge to say, well, why don't I just rewrite everything from scratch really neatly into these clusters.

The reason why you shouldn't do that is because that takes time and you're not always going to want to do it. And once you stop doing it once, you're going to stop doing it all together. So you want to try to get down these revisions, these edits, these completions to 15, 20 minutes max. So if you take notes on a computer, just get right in there and move things around. If you take notes on paper, just leave a lot of room when you're doing that so that you can come in and add questions or add conclusions, use arrows if you need to box off some things and then put a big arrow that moves those points to another question evidence conclusion cluster.

That's fine. I've seen students actually block off bullet point notes they took during lecture draw boxes around it and label them like A, B, C, so these blocks are actually labeled. And then what they'll do is at the end of the pages for that day's notes, they'll write the questions and conclusions. And where the evidence would go, they would just name the relevant blocks full of evidence,

like A and B or C and F. So they don't have to reconsider. copy it. Reducing friction makes a difference. That means you're more likely to stick with it. More broadly, for the many listeners who are not in a student context, I think we don't think enough in general about note taking, be it in a seminar or a meeting or reading a book or watching a video online that's informative for our work. The structure of notes matter. And almost any professional note taker, let's say like a professional journalist, for example, or an academic at a seminar, is going to do work on those notes after

the acute period of listening to information. So that's just something to keep in mind that what I'm talking to Gabby about in the context of taking notes in a humanity style liberal arts class has general applicability to anyone who needs to capture notes on a non-trivial process in a professional context. There's the acute phase where you're listening, and then there's the phase after that where you're continuing to structure and clean. You've got to have some sort of formatting, in mind that really focuses on the things that you care about. All right, Gabby, thanks for that question. Let's do one more really short student question. Hi, Cal. For optimal learning, is there a

recommended amount of time one should leave between first learning a concept and then performing active recall on it? Thank you. Well, Nino, the rule of thumb there is long enough for the information to leave your working memory. So if what you were just studying is still in your working memory, if you then do a review, you're not actually reviewing whether or not you had cemented those concepts into your long-term storage, which is your ultimate goal. You're actually just recalling it directly from your working memory. Just like if I said, okay, memorize this phone number. And I rattled off, you know, 609, 555, 3556. And then immediately said, okay, what did I just say? You could probably just recall that right away because it's in your working memory. But if I

ask you again a week from now when it might matter, it's probably nowhere to be found in your long-term store. So that's the rule of thumb. Get it out of your working memory before you review. There's two ways to do this. One is just simply time. If you give it enough time, it'll leave your working memory. And two is to actually push it out. So you review one thing. Let's call this item A. Then you switch over and review something else, call that item B. That review of item B flushed your limited-sized working memory out, so item A is no longer in it. Now you can go back and do the review of item A because you're going to be polling exclusively at this point from long-term memory.

All right, good short question. Before we jump to our next question, which is about big goals versus small task, let's take a brief moment to give thanks to our brand new sponsor. I want to talk to here for a moment about grammarly. I have been using Grammarly Premium and really I have to say this have been amazed by what technology is now capable of doing when it comes to improving your writing.

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As a listener of the Deep Questions Podcast, you can get 20% off Grammarly Premium when you sign up at Grammarly.com slash deep. That's 20% off Grammarly Premium when you sign up at Grammarly.com slash deep. G-R-A-M-M-A-R-L-Y.com slash deep. Our next question is about the balance between the ambitious and the mundane. Hi, Cal, I was wondering your thoughts on big initiatives, big goal setting versus daily plugging away at things. So when do you determine that it's good to set a big goal and go hard after that and make one big push with your time and effort toward one thing, kind of let everything else go on the back burner? and when do you determine that you should just budget a little time and effort toward a few good things, a few goals, that you're, you know, things that you're trying to improve. This is something I have a hard time with kind of knowing what goals to chase and then when to make a big push.

So any thoughts you have on diagnosing whether something is a big initiative item or just to keep plugging away at it item would be helpful. Thanks. So Ben, when it comes to goals, both figuring out what you want to work on and how you're going to work on and how you're going to work on it. The really key scale in your productivity discipline is the quarterly planning. This is the planning you do just a few times a year. Now for me, I do it for the fall and for the spring and for the summer. So roughly actually matching a semester calendar of the university. People in other professional contexts do it in the traditional four quarters that are going to connect to the standard, let's say, fiscal calendar.

So four times a year or three times a year, you sit back and you make a plan for the quarter or semester ahead of you. It's what I call quarterly planning. This is where you figure out, what am I working on that's important to me? What is the big goals I'm working on? Is it one big thing? Is it a few smaller things like you alluded to? That is where the aspirational rubber meets the day-to-day productivity grind road.

That's where that type of thinking happens. Now, once you actually have your quarterly plan in place, you then reference that when you're doing your weekly plans. So you look at that quarterly plan, you look at the reality of your week, and you say, how can I best make progress on this quarterly plan in the week ahead of me? And that's where you actually begin to move around on your schedule, work towards those bigger picture goals. As you get to the individual days, of course, that then gets transformed into specific time

blocks. When you get to that specific time block, the work happens. So that quarterly plan. discipline is where you make these decisions. How do you make those decisions? How do you figure out what goals to take on? How do you figure out whether to do a big thing versus a few smaller things? Well, this is a really complicated question that does not have a single simple answer. It is here, however, that we're going to elevate ourselves one higher scale. So we start with the daily, move up to the weekly, we move up further to the quarterly. What is about?

that, well, somewhere you need to have what are my values and what is my strategic plan for my work life. We talked about this in a previous episode. We called it rooted productivity. This notion that you have one place where you keep track the root of all of the plans and systems that go forward. This route, as I mentioned, should have your values and I suggest that you have a strategic plan in there for how am I working on these values? What am I working towards? based on these values in my working life? What am I working towards based on these values in my life outside of work?

It's there in the strategic plan informed by your values that you have that vision. This is what I ultimately want to do with my professional life. This is what resonates with me. This is what I think is important for a life well lived.

And at a big picture, this is what that means. So you're not talking in your strategic plan, your value supported strategic plan. You're not talking about, I want to specifically do this. Here's my goal or here's my list of goals. So it's probably going to be at a higher level than that. It's I want to run my own business that is trading off autonomy for income so that we're

financially well off. But more importantly, I have a lot of time affluent so that I can spend more time with my family. Or I want to eventually be able to leave, you know, leave this city and, you know, move somewhere more scenic, right? I can spend more time outside and not have to work in the afternoons. Or I want to be a really influential person in this sector of the media. I want to have an impact there.

Whatever, right? You have these visions of this is what resonates with me. This is in general what I'm trying to go for in my career. This is influenced by my values. Now you have this big value influence strategic plan. That's what you're looking at when you get to the quarterly plan and say, what do I need to do? And now you come up with goals that you predict are going to be most effective,

given where you are in your skill level, where you are in your career, and what is the reality of the time ahead of you in this quarter, what's going to be your best bet. And you don't have a definitive answer. You're making a guess, but you're making an informed guess. So if you're like me and you're a professor, you're looking at the fall,

and you have a product launch in the fall, and you have a big administrative position, you might say, this is not the time to take on a big goal that's going to require a lot of dedicated attention week after week. I'm just not going to have it. But if you're like me and you're a college professor and you're looking instead at the summer

when you're doing your quarterly planning, you might say, great. This is a really good time to take a big swing on something that's going to take a lot of effort. It is no coincidence, for example, that the podcasting, component of my burgeoning media empire. A word, by the way, I should say I'm saying with ferocious air quotes in the studio right now.

There's no surprise that happened during the summer, launched in May and got up to speed in June, July, and August, right? Because that was a good time for all the effort involved in getting that running in the way that right now, for me, the September is not. So what I'm trying to say here is that you have this high-level strategic vision. It's influenced by your values. when you get your quarterly plan and you're trying to figure out how do I actually put that into action into the world to ape Matt Crawford, how do I make these intentions manifest concretely?

That's when you do this survey. What's realistic? What's not? What's happening in your professional life? What's happening in your personal life? What actually makes sense? And that's where you make the decision, Ben. I'm just going to plug away to a few small things here

so that I'm making progress, but it's not a big swing or maybe I'm taking a really big swing and I'm going to go for a really big thing. That's when that decision is made. Then when you get to that weekly, daily planning scale, it's just execution time. All right, I have the marching orders.

The marching orders are in place. I don't have to relitigate things like what I care about. I don't have to relitigate what my vision is. I don't have to re-litigate what goals I'm working on right now. It's all there. It's all written down. I'm just trying to figure out what do I do with this week. How do I make progress on this?

Oh, Thursday is my empty day. If I move this meeting, I have all a Thursday. morning clear. Great. That's when I'm going to make progress on this goal. Or I'm going to wake up early and do one hour every morning. That's the only way I'm going to make progress on these goals or whatever. That happens in the weekly planning. It's logistical. It's not inspirational. It's logistical. It's not aspirational. And of course, when you get to the day, it's just time block, time block, time block. So Ben, I don't know if that's getting at exactly what you were asking about, but I do think it's helpful to clarify when this type of thinking happens. And so it sounds like for you,

This quarterly planning moment is going to be a crucial moment for you. It's where you're going to resolve a lot of these questions about what to work on that you're not sure about. But you have to have that value-influent strategic plan for your career in place if you're going to be able to make any sort of cynical decision during those quarterly planning sessions. So that's probably where you're going to need to start. Don't be intimidated. You're not chiseling this in stone. You can update that plan a lot. It takes a while to get it right.

It's just better to have something versus nothing. Get that down. Do some quarterly planning. And then execute. All right, let's do one more question here. This is not technically a productivity habit, tune up question. But it is a question about the professional role that I get asked a lot. And so I thought it would be fun to tackle it.

Hi, Cal. My name is Brett, and I'm an adjunct professor in organizational leadership at a university in Georgia. I'm acquainted with your extensive body of work in the area of and I've got a question about your very early publishing experiences on the topic. For your first book or two, did you have an agent representing your manuscript to publishers or did you contact publishers directly? I know from your bio that you sold your first book to Random House while still an undergraduate student. Please elaborate about your travels on the Rocky Road to non-peer-reviewed book publication. Thank you. Well, Brett, I appreciate this question

because it comes up a lot. So here's what I have learned about nonfiction publishing with traditional publishing houses. First, you sell your book to an agent before a publisher. With few exceptions, you should not be directly approaching a publisher with your book idea. You should be approaching an agent. An agent will then help you write your proposal. The agent will then sell it to the publishing houses. there's very little slush pile acquisitions in the world of nonfiction writing.

You have to understand that these professional agents have relationships with these editors. They have lunch with them all the time. They've built up trust. They talk to them about here's the projects you might be interested in. Let me just nudge you on something that's coming along. That is how most of these deals are done. It's easier to get an agent than it is to sell a book. So basically a publisher will think, if you are bypassing the agents,

I'm just going to suspect that you weren't able to get an agent. And if you couldn't get an agent, then we certainly shouldn't be publishing you. So you want to focus on getting an agent, not trying to go straight to a publisher. Point number two, if you are writing nonfiction, you do not write the book first. You sell the idea, you get an advance on the book. That advance help pays for you to then write the book. Now, in fact, if you have written the book already, that can hurt your chances of selling it. An editor would like to have some say in how the book unfolds.

The editor would like to be a part of the writing process. The editor would like to apply his or her expertise to your crafting of the narrative. If you have already written the book, this is not a good thing. This is actually probably going to be a red flag. Now, there's obviously some exceptions. If this book that you self-published or already wrote is chicken soup for the soul and you've sold a million copies already, they will be happy to publish it officially. But outside of those exceptions, for the most part, you do not write the book first.

Important caveat, this is different in fiction writing. In fiction writing, you are submitting, for the most part, if it's your first book, in particular, full manuscripts. So fiction does this different than nonfiction. So don't start your ambition of being a nonfiction writer by saying, great, I want to write every day for an hour and get a chapter done every week and I'm going to get a whole book together. No, your focus is not on writing the book yet. You have to get the agent and the agent has to sell it and then you start writing. So three, how do you get an idea that can sell? Well, the most consistently applicable piece of advice I have been given and have observed about selling an idea.

in nonfiction, is there tends to need to be two things true. One, it's an idea that there is some audience out there that's going to say on encountering it, I need this information in my life. I want to know more about it. And two, you have to be the right person to write it. Now, of course, it's the exception of books that are in the general nonfiction space

that are just trying to cover in detail an interesting person, or an interesting event, like a David McCola biography, or a Susan Orling books on the library system in Los Angeles or something like this. Those type of books are written by professional writers almost always coming out of journalism. That's kind of its own category. So if you're a professional writer, you're a professional journalist, for example, or you're an academic that specializes in a particular historical topic, that's sort of a separate thing.

Right there, the thing that makes people interested in the topic can be, it's just an interesting topic. And you are a really, really good, well-known, established writer. So you can write about it in a way that'll make it interesting. But if you do not fall into that category, you have to have a topic that people are going to say, and by people I mean at least some non-travial market segment, people are going to say, I need this. And two, you have to be the right person to write it. where people get tripped up is when they ignore one or the other of these items, right?

So if you say, look, man, I just have observed in my life, I think our culture is all wrong about X, like the way we think about whatever, kids in schooling or something like that. And I just want to write about it. Well, then the question's going to be, maybe that's a topic that there's a big segment of people who are burnt out on that and care about, but the question is going to be, are you the right person to write about that. Do you have some sort of particularly unusual experience or some particular expertise in that topic? If not, you're not going to sell it. Or, you know, I like gardening. I want to write a book about gardening. Well, what is it about gardening that you have to say that some

people are going to see? There's a segment that will say, I have to read this. And what expertise do you have, what have you done that's interesting? What have you done that makes you the right person to write about it? You have to marry those two things together. Or you can be a professional journalist, which is, again, a whole separate, a whole separate category. So that's what I've learned about nonfiction writing. So let's focus on me in particular. How did I apply this advice?

Well, let's start with the topic. The very first book I sold, I had pitched it under the name Conquer College, but that was eventually changed to how to win at college because of the two hard cuck-cut sounds in a row, which does not roll off the tongue very nicely. I sold that right after I turned 21.

So that was the summer before my senior year of college. So why was that a good idea? Well, first of all, I had this pitch that for people who are students going to college are about to go to college, a book that was giving them advice on how to do well would be something they might feel like, oh, I need to read this. So I had a pretty good idea there. Not exciting, but at least there's clearly an audience for the book. I had an extra twist for it, which is sort of forgotten now, but it was somewhat unusual at the time.

When I pitched Conquer College, my twist was, I'm going to write this like a business book. The college advice books that existed in that time, this was 2003, the college books that existed around that time, they all had this aura of, for lack of better word, kookiness, zaniness, or fun about them. There was this sense among editors in New York that a young person was not going to buy a book if they thought it was too serious because that wouldn't be, fierce air quotes, cool in fierce air quotes.

One of the best-selling college books at that time was called The Naked R roommate. Another best-selling book at that time was called Major in Success, and my memory was the cover at that time had the author in a kooky pose on the cover. He was sort of kind of half running in a sort of silly, mimesque fashion. And I came along, and I had this weird background that I had been an entrepreneur in high school, and I came along and said, no, no, no, no, college kids take themselves way too seriously. And so you want to acknowledge that and write the book seriously. So let's just write it like a business book.

Let's get down the business. You want to do well. Here's how you do well. Some of this advice is going to be hard. Suck it up. This is what it takes. So I had an idea. I was like, look, no one had written a college book like a business book in a while.

And there was this huge demographic explosion of people going to college. There was an audience that was going to think, hey, I really need this book. Was I the right person to write this book? Well, there's a reason why my entrance into the publishing world was college advice books. Because I was a college student. so I could make an argument that it made sense that I was writing that book. I was a student writing about the world around me. I understood college students and college lives in a way that a professor writing it later in their career would not.

Writing a college advice guide was probably the only topic that I could have possibly sold a book to a large publisher to at that stage of my life. Because again, it has to be a good topic, but you have to be the right person to write it. I was 21. That was the only topic, I think, in which I could have convinced people that, yeah, I am actually the right person to write this book. Now, keep in mind, I was also someone who knew how to write. I had been a columnist for the newspaper at Dartmouth, and I'd worked myself up to be the editor, the editor-in-chief of the Jackal-Lantern, which was the Humor magazine. And, you know, Ivy League Schools take their humor magazine seriously.

Dr. Seuss used to draw cartoons for this one. And so I had writing chops, at least as much of a writing chops as you could have as a 21-year-old, because, you know, I was out at an Ivy League school and was the editor of an institution, a magazine that had been around for 100 years, and wrote a lot. So I was a not bad writer. There was a legitimate case that I was the right person to write a book about college advice. Once I had that all in place, I went and got my agent. What was my strategy?

Well, this is what I recommend to anyone. trying to find an agent, find a similar book, turn to the acknowledgments, see who they thank, then write that person. Pitch an agent and say, the reason why I'm pitching you for this book is that I know you worked on X. And that's kind of what I'm trying to do here. And that's actually what I did, is I took a business book. It was called How to Become CEO, written by someone named Jeffrey Fox. and I knew this book for my entrepreneur days as a high school student. And I decided that how to win at college, originally Conquer College, it was going to be written in the style of how to become CEO.

It was a sort of aphoristic business advice guide. And so I wrote the editor, I mean the agent, I found her. I found her in the acknowledgments. Jeff was thanking her. And I wrote her and said, the reason why I'm pitching you this college book is that I want to write it like Jeff wrote how to become CEO. I think there is a market there. I think there is a hole here for books written in that style. And Jeff had actually given that that that advice. The advice in that book he had actually originally given as an alumni, I think it was an alumni

speech. It was a speech soon to graduate students or recently graduated students from the Wharton School of Business, if I remember correctly. So it was already sort of in that atmosphere of giving advice to young people. So the agent got that immediately. A hundred percent understood what I was going for. And her name is Lori, and I've been working with her ever since. I would not have been working with her. I don't think she would have paid attention to me if I had not actually had done my homework and said, this is why I'm talking to you. You worked on this book. And this is what I'm trying to do, but for a different audience. All right. So that's what I did. I found an agent that was a good match by using the acknowledgments of similar books,

pitched the agent. The agent came on board. My memory is Lori smartly required me to do a little bit of writing. I mean, she wanted to see my writing samples, and then she wanted me to do a complete table of contents. And I had very cleverly, if I do say so myself, I had very cleverly done this trick before I pitched the agency. I'd done this trick where I had gotten an article commission

that overlapped the topic of my book. And then I did way too much research for that article. I basically did all of the research I needed for my book for that one article so that when I talked to Lori about the idea, I could say, I've already done all the interviews for this book. So I can tell you what's going to be in it. It's not going to be nonsense. Here's what it's going to look like.

I've already done the interviews. Again, I was trying to head off fears about why am I going to work with a 21-year-old. So that's how I got started, and that is a case study of my general advice. You don't write the book first. You pitch the agent before the publisher. have to have an idea that's going to be clearly appealing to a market and you have to be the right person. Now, two things I want to say here in closing is I can't emphasize enough the number of times

I talk to people who want to publish that have not done that last step correctly. What they have instead is an idea that they think is interesting, but they are not the right person to write it. That's the hardest part. I wanted to be a writer. I had to figure out how do I get into that world. College advice was the only thing opened to me as a college student, and then I built on it.

It really does hold. You've got to be the right person to write it. If you're not a professional journalist, the idea by itself has to excite people. There has to be some segment that says, huh, I have to read that. The second point I want to point out is don't come up with your own rules.

I think people like the romanticism of getting up and writing every day. I think people like the romanticism if I'm going to do 1,000 words a day and I'm going to do 10,000 words a week or whatever, and I just want to trick out my writing shed and get rock and rolling. But that's just not the way it works for nonfiction writing.

You don't write the book first. And you can't just roll with whatever idea you had first. It's hard to come up with the right idea. It's hard to figure out the idea that you're the right person to write. You may have to do some more work in your life to become the right person to write it. All of that is hard. It's annoying to pitch agents because you get rejections. You've got to put the idea out there and people might not like it.

Again, all this is easier to just go into your shed and bang away at the keyboard, but you don't get to that until much later. So anyways, again, this is not technically productivity, tune up advice, but I think a lot of people think about writing and think about being writers. And if you want to tune up what's involved in becoming a writer, this is what I've learned. There are, of course, exceptions, but I think these basic rules more or less hold true for most people. So, Brett, I hope that is useful to you and to my audience in general. I hope you found some utility in these ideas about book publishing, these reality checks about book publishing.

as well. So that is all the time we have for today. Thank you to everyone who submitted questions. If you want to submit your own questions, you can do so at speakpipe.com slash Cal Newport. Thank you also to our sponsor, Grammarly. Remembergrammerly.com slash deep to get your discount. We'll be back next week with the next full episode of the Deep Questions podcast. I actually have something special planned, so stay tuned for that. I think you'll enjoy it. And until then, As always, stay deep.