(upbeat music) - All right, what do we got next? - All right, our next question, we got a question about the deep work buckets and then Keystone habits. So let's take a listen. - Hi Cal, it's Nevek here. I'm wondering if you could explain the difference between deep work and the roles that you play and your buckets and your Keystone habits in those.

I'm assuming you have other things you do in the buckets and I'm just not clear how you see the relationship between the buckets and your roles and I suppose deep work. Thanks. - All right, this is a good question because we can clarify the relationship between the deep life, the philosophy that includes the buckets and deep work, which is a type of professional activity.

Jesse, let me ask you though, right off the bat, I sort of stumbled into this terminology of buckets early in the pandemic when I was thinking through the deep life and now we're kind of stuck with them. You think this is a good thing or a bad thing? - You've talked about the buckets for a while 'cause I've been listening to your podcast since the very beginning.

I like the terminology and I remember you mentioning it even before I started working with you, but I've always been a fan of the buckets. I use it when I explain it to certain people, so I think it's fine, but. - Yeah, all right, so we got what it is.

Buckets, we're stuck with buckets. Let me do, by the way, let me do an update on the book and then I'll get to this answer. But I just finished my sixth version of the potential outline for this book. I've gone through six versions, had a hard time with it.

This is the first version that I actually sent off to my literary agent and said, okay, I think I have this thing cracked. I think I might be ready to write a proposal. So Jesse, let me do an update. Let me give you the latest update on the potential book I will be writing about the deep life and then we'll get to the meat, we'll get the meat of this question.

- Yeah, let's do it. So here's what was struggling with me before. I was struggling before when I was thinking about this book because it was important to me that for this subject matter, that the book was, for lack of a better word, smart. I didn't wanna tackle something as philosophically resonant as living a deep life.

I didn't wanna tackle it with, and now here's the seven steps and here's bullet points and here's lazy writing, which in the nonfiction space, the pragmatic nonfiction space, you know you get lazy writing when a lot of rhetorical questions enter the scene. That's a little tip when you get a lot of, but would this really work?

What about a duh, what about a buh? It's like, man, that's your notes for what you need to craft good writing about. You can't just put the rhetorical questions into the writing. So I thought this topic really needed, it needed to be smart. I mean, it's a complicated topic, but my issue was when all I was doing was trying to come up with a table of contents for the book, I was putting all of the necessity to make the book smart onto the table of contents.

And so it was leading me down these unusual and contrived structures for the book because it's like, well, I want the structure itself to convey that this is something different. And eventually what I realized was, no, keep the structure simple and let the writing do the work. And in fact, not only make it simple, why don't we distill down to its essence, like the very elements of a Cal Newport book and simplify them down to its purest form so the structure is there and it's there, but in a minimalist form, and then let your writing do all the work of showing the philosophical depth of this topic.

And so that's what I ended up doing with my current outline in the prologue. Like right up there in the prologue, it's me, it's early pandemic, this topic arise, I coined the term buckets. And I just let this one short prologue is gonna do all the work of just motivating why this topic matters.

It's been around forever, each, whatever, each generation comes at it differently. We have our own moment where we're kind of re-appraising this topic, but no, like multiple chapters with citing 70 things, a prologue that is just grounded in a place and a time and me, boom, right? Then we go to a next chapter, prepare.

All of the stuff we've talked about, I mean, the buckets, in general, what makes a deep life deep? I mean, I've pretty much simplified it in my own thinking that the definition of a deep life is you radically align, radically aligning your life to be in alignment with things that you really value.

So it's about not just aligning elements of your life, but being willing to make radical changes to your life to align it to things that you value. I think just, let's just give the definition. Let's talk about it. Like, what's the hard thing about it? Well, it's hard to figure out what changes to make.

We have this bucket system we'll talk about in a second that can help, but like, there it is, just one chapter, call it prepare, out of the way, not dragging this out, not going whatever, just boom. And then the whole rest of the book, I have five chapters. Each is a different element of something you might radically align as part of building a deep life, naming them with one word verbs and let the writing do the work.

So you have this prologue, you have this prepare chapter, and then it's right now, the terminology I have is move, quit, serve, train, wonder, it's the current list. And the list might change, but one word, one verb, like I'm trying to get down to the essence. Like let's get down to the essence of a Cal Newport book.

Here's the problem, here's the solution. Let's look into how you implement the solution, just getting it down to the essence. And then I can let the writing do the work. And I'm gonna follow my own journey through these chapters. I'm a character in this, they're gonna be asymmetrical. So it's not like every chapter has the same structure as every other one.

I really wanna get away from opening story, interpretation of the opening story, complicating story, four bullet points. It's gonna be, some chapters be different than others. I'm a character in it, let's be nuanced in tackling these issues. Take these different elements of building a deep life and really go try to understand why do they resonate?

What's at the core of them? What do you have to think about if you're trying to do an alignment here? Give some respect to the reader to help put the pieces together. So that's where I am now, a very simple structure. Now it then ends with an epilogue. Okay, here's how I've changed my own life.

Very simple structure, one word chapter titles. Get down to the core of it and then we'll really let a journey unfold, let the writing do what the writing needs to do. I don't know, so what do you think, Jesse? Better or worse than where I was before? - I like it, so I have a question.

When you were doing, when you were trying to make the book seem smart and you were developing the table of contents, how did you explain that to the agent or whoever you submitted it to that it was the writing that was gonna be the smart work? Or did you write the epilogue as well so they had an example?

- So yeah, it's a good question. So what I was doing before is I was getting too cute with the structure. Well, I think the last time I talked about on the podcast, maybe at that point I was doing paths, like here are the four main paths that people follow.

And that wasn't quite right. I wanted to get to the crux of the matter, like what are the actual changes that create the depth, the resonance? I wanted to be more concrete, so that seemed too complicated. And then I had a form where each chapter was a setting. So it was like, I'm at this farm, I'm at this like writer's retreat or something like this.

And then I would build out from the setting. But I was like, this is again, it's not clear to the reader, why are we at this setting? And I don't want this to be just one of these reflection books where I just like, I have these kind of reflections and I prove that I'm smart with my writing.

And that seemed too cute. And so really, and then I had more complicated traditional structures where here's like three, four chapters on like what's needed to prepare for the deep life. And I was like spending all this time on it, like that felt forced or whatever. So I just simplified it down to these one word chapters and I sent it off just for my agent to look at.

But I was like, the structure should make a lot of sense. Here's my standards, I've just simplified it. But the writing is gonna do what the writing does. It's gonna follow my story, not every chapter is gonna be the same. And it was more for me, I just felt a clarity.

And I felt like a book like this needed a lot of clarity. Just you look at the table of contents, like I know what you're up to, let's get into it, if that makes sense. - Got it. So this being the sixth version, how long is that process, like six months?

Like you submit a version every month or is it? - So this is the first version I submitted. So the first five versions, I was like, no. So my whole thing, my whole process is I rely heavily on my sense of taste. To borrow the terminology from Ira Glass, that like the first step in trying to produce something good is you have to develop the taste to recognize good things.

And it can be frustrating because then you know when you're doing stuff that's not hitting that level. So I know what I'm looking for and I'm very empathetic. So I put myself into the head of a potential reader and try to simulate what's that response? Is there an aspirational response or not?

So I'm very empathetic. I'm like this in person by the way too. I very strongly read and feel empathetically what's going on in a room. If I'm talking to someone, like every little nuance about their state of mind and how they're feeling, it hits me really big. And this has negatives and positives.

It has some social implications that aren't great but it's good for writing because I can simulate the mind of the reader really well. And so I really began working on this in earnest in July, just trying to get an outline. And for the other five, I would finish it.

I would sit with it and it was just a feeling. It's not right. It's hard to explain. It's like a little premonition of like, something's not right here. There's some grit in the gears. And I would sit on it and I'd just say, this is not right. And then I would try again.

And I think it's not quite right. And I would try again, but it's not quite right. So it's really, for me, it's all this intuition. I just have an intuition when I finally feel like I think I'm honing in on something that the reader's it's gonna get. It's all about pressing the buttons I wanna press.

I want the experience of reading the book to be exciting. Like you have the sense of I'm gonna change something in my life and I'm getting some revelation and there's a whole sense that I'm going for. And so I've been sitting with this one for a while and feel better about it.

So I think I'm getting closer. - Were you influenced at all by your friend Ryan Holiday's new books with the one chapter titles that he's been doing? Did that influence at all with the one chapter? - Yeah, yes. Yeah, so Ryan, I think Ryan is a great example of this, of keeping the form simple and clear.

And then letting the writing do the work of actually affecting the person. Yeah, I think he's a great example of that. If we're gonna be really highfaluting about this and self-important, as you know, I went through this phase of reading a lot about film, film studies, et cetera. And technically you could think about what I'm interested in is the pragmatic nonfiction equivalent of auteur theory in film.

So in film, when you look at Fellini and auteur theory, there was this sense of like what the, especially in the 70s and 80s, that these auteur directors would take a well-established genre and then they would work within the constraints of that genre to create art. And it was actually in the tension of their work against the constraints that you would subvert this or what they would do with this, that you would actually create the value that somehow that there was something to this that was even more special or magical than just starting with a blank slate.

So this would be the difference between Ford working within the constraints of the Western and visually and storytelling-wise working with it, or Clint Eastwood in "Unforgiven," which I recently re-watched, taking the constraints of the genre that he helped define earlier in his career and is in the subverting of the constraints that actually the power comes out.

And then comparing that, for example, to Terry Malick, who was just like, "I'm gonna construct this thing from scratch. "This movie, it's gonna be whatever it's gonna be." The auteur theory, you work within the genre. I think it's an incredibly self-important way of describing how-to books that I write, but at least it gives me some sort of motivation.

That, and Ryan does this too, work within the constraints of the genre. So I have a very clear constraint, motivation, idea. All right, so here's this issue. Here's my original idea about what to do about it. Digital minimalism, deep work, replacing the hyperactive hive mind. Then a journey to understand how to implement it, which is where you help the reader instantiate in their own mind how their life might actually change to act on that promise.

That's my Western movie or detective novel, and I'm trying to work within it. So that's what I'm doing with this new one. Let's just distill it down to one word, incredibly simple. Get the motivation to a prologue. Get the whole, here's the idea down to just one chapter. Use all the new muscles I've been building at the New Yorker to be clear and well-crafted and balanced and momentum going, and then just see where it goes.

So this is the self-important stuff I tell myself. So I don't get bored. I don't know, do you buy this? This is probably going too far, right? Talking about auteur theory. - No, I like it a lot. In fact, if it becomes a movie, we can get Andrew from the previous call to be a character and it's got all those other traits.

- Yeah, I left that, yeah, I did leave that out, that that's gonna be a big part of the book is gonna be these big call-out boxes, and I'm gonna have a sketch of Andrew, really dramatic sketch of Andrew, and then a lot of details on rich data pipelines.

Because you gotta subvert expectations. You're like, oh man, what's gonna happen? This guy's gonna quit his job, and then it's XML formats for maximum data portability. That's, I think that's where the magic's gonna be. - No, I love the explanation. I think it was great, so. - There's an actual question lurking in there, wasn't there?

- Yeah, so the question was about deep work and working with the keystone habits. You get this type of question a decent amount, but I always love hearing the explanation 'cause I'm a big firm believer that people need to be continually coached, so. - Yeah, okay, so yeah. Now let's get back to the meat of it.

All right, so we have the deep life. We have this growing definition of the deep life that I've been refining, where it's really about living your life in radical alignment with things you value. So you're aligning to things you value. You're willing to make radical changes to actually make that alignment, maybe radical changes to where you live and work or the structure of your day.

Implicit in this definition is also you're comfortable missing out on other things to do this priority. So I'm gonna really focus on a few things that really matter and radically align my life with it. All right, so that's my vision of the deep life. The hard part about the deep life, and this is something I've been refining when I've been thinking about this potential book, the hard part is, well, figuring out what that is.

Like what's really important? How do you align your life to it? There's some preparation that's actually required to get better in tune with yourself and to get more comfortable with the idea that you have efficacy, that you can actually influence the way your life unfolds. A lot of us aren't really used to that except for in very minor ways, like trying a new exercise routine.

And so the bucket system I talk about on the podcast a lot is in some sense a way of doing that preparation, beginning to learn what's important to you, beginning to build that muscle of aligning your life with the things that are important, even if that requires sacrifices or deemphasizing other things.

It's the preparation stage. And then once you're done with that preparation stage, then you might actually make some more radical steps. Now I'm ready to like with confidence, move across the country, go to the farm, radically change our work situation, whatever it's gonna be. So I see now the buckets as a preparatory step towards a more extreme push towards a deep life.

The idea briefly is you identify the important areas of your life. I call these the deep life buckets. The examples I give often are alliterative and I'll start with C. So the original group I used to talk about was craft, community, constitution, and contemplation, but people have different lists of what's important to them.

And what I would recommend in this system is that you start, step one, identifying a keystone habit for each of these buckets, something you do on a daily basis and track that you actually did it that's not trivial, but is also tractable. So it's not, you know, I clap my hands twice, but it's also not, I ran a half marathon every day.

These keystone habits should be something that advances something you care about in that bucket. The idea here is not that this will radically transform your life, but that you begin to get used to this idea of I intentionally prioritize each of these things. Each of these things gets attention.

So that's step one. Step two, then I recommend taking each of these buckets in turn and giving it four, six, maybe eight weeks. So I usually say average out four to six weeks where you focus just on that area of your life and overhaul it. Like what more permanent changes do I wanna make?

What things do I wanna eliminate? What new things do I wanna do? What more permanent changes do I wanna make to make sure that that part of my life is getting a good amount of attention that I'm extracting from it a good amount of value in my day-to-day life?

And that takes some time and experimentation. So that's why I say take at least four to six weeks for each. This is a concept that I stole from the medieval Jewish practice of Musar, M-U-S-S-A-R, which is a practice of virtue cultivation where you actually focus one month at a time on different virtues that you're trying to improve and then you cycle back again, very into that idea.

I think it's a really cool idea that should be known more widely. So I'm sort of pulling from there. And then when you're done with those overhauls, you are gonna be in a state now where you know what's important to you because you have been experimenting with it and trying to amplify things and just getting in touch with those intimations for each of the areas of your life.

You've just spent a month thinking nothing about that. And you feel a lot more efficacious because you've now done non-trivial rewiring of elements of your life to make sure that each of these buckets is being satisfied. That by itself is gonna put you on a much more stable foundation.

If you did nothing else, I think your life is gonna be deeper. It also puts you into the right place if you wanna make the radical changes 'cause now you really know what you're all about and you're confident you can make changes. So that's the deep life bucket system.

Deep work, by contrast, is a particular type of professional effort. It is when you're working on something that is cognitively demanding and you don't context switch. So you give it your full attention. Much more minor in the grand scheme of things. So where might that show up in here?

Well, the craft, what I call the craft bucket is the bucket that's dedicated to what you produce professionally. It also, by the way, can cover other things you produce that maybe is not at the core of your job, but any type of producing of things that are valuable. If you're the actor, Nick Offerman, for example, from "Parks and Recreation," he has this fantastic woodshed warehouse in the suburb of Los Angeles somewhere where he builds these great wood creations.

It's not a business for him, but it's craft and that's important to him. So it's building things, but definitely your professional life is covered there. When you're considering craft, deep work matters. Because as we talk about, you wanna produce things of value. That means you wanna make sure that you have good time protected for deep work.

And you wanna work on the load of work in your life, probably so that you have enough ratio of deep to shallow work. Yeah, that's all considerations that apply narrowly when you're trying to figure out your craft bucket. So to get to the definitive answer to the original question, the deep life is this big idea.

If you're going through my preparatory deep life bucket system, during the time you're focused on a craft or whatever your equivalent is of the craft bucket, that's where you'll care about deep work. And I like to make this point because I think deep work as a concept has inflated for some people to cover a lot of things.

And I'm trying to keep these separations more clear. So this is why I like to talk about, let's get deep work narrow to what it is, focusing on something hard without distraction. And let's use the term deep life to capture this broader goal of living a life that's radically aligned with your values.

All right, so I don't know, do you think, I think Jesse asked probably the breaking, I'm breaking records here for length of answers before we actually get to any information relevant to the original question. - That was a good one. That one was 21 minutes probably, pretty close. - Oh dear Lord.

- It was solid. - All right, all right. You know what, I'm going fast. I'm going fast. This is my challenge. Fast answer on this next one. Be ready for it. (upbeat music)