Okay, so I have a question for you. How

do you figure out what to do with your

time during any given day? Now, I think

this question matters more now than it

ever has before because if you don't

have a good answer to it, if you just

sort of wing it as your day unfolds,

guess what forces are going to take

control of your intention? Email, Slack,

social media, online chatter, YouTube,

streaming services. This is a show about

finding depth in a distracted world. And

to succeed in this goal, you need a good

planning system. But how do you create a

system that's not only going to work,

but is something you're going to stick

with over time. This is what I want to

talk to you about today. And I have an

expert that's going to join me to help

us in this conversation. Her name is

Sarah Harter. She's a a doctor and a

mother uh and also a planning

afficionado. She's the host of the best

laid plans podcast on which I've been a

guest. Um, and in December, she

published a book with that same name

that had the subtitle a simple planning

system for living a life that you love.

Amazon selected it as one of the best

non-fiction books of the month. So, I

invited Sarah on to get into the

nitty-gritty details of how to build a

useful and realistic planning system.

She even helps me figure out solutions

to some problems I've been having with

my own systems. So, there's some changes

I make after talking to her. She also

makes a case for why she only uses

analog tools, which I think is

interesting. I'm not quite sold on that,

but I think it's an interesting case.

So, anyways, this is a deeply practical

discussion and one that I think is

absolutely vital to our mission here on

this show. So, let's get into it. As

always, I'm Cal Newport and this is Deep

Questions, the show for people seeking

depth in a distracted world. And we'll

get started right after the music.

>> All right. Hey Sarah, welcome back to

the show.

>> Thank you so much for having me on. I'm

excited to be back.

>> Of course. I mean, I'm excited about

your book and I'm excited to get into

the weeds on planning. I have a whole

list here of practical things. I want to

learn from you. I want to talk about

like what makes a good planning system

good. How do you keep systems

sustainable over the long run, digital

versus analog, family versus personal

versus work, tasks and planning and how

that differs. I I actually saw a lot of

connections between your new book and

slow productivity. So, I want to get

into that as well. So, we're going to

walk away from here with like lots of

ideas about how to get your life under

control, but I want to start by just

motivating this entire conversation for

my audience. Like, why is planning

important? We need to ask that question.

Why is it being talked about? Like, why

do I care about it on this show, which

is largely about fighting back against

digital distractions? I actually think

that it's uh really well connected. So

I'm going to give you my take for why I

think planning is important Sarah and

then I'm going to ask you to sort of

give your the way you think about it.

Right. So from what I noticed is there

was a period I really kick it off around

2019 uh with Jinny Odell who brought a

sort of anti-neoliberalism anti-

capitalism critique to the world of

things like planning and productivity

and the sort of related topics and

essentially the the anti-neoliberal

critique was to care too much about

planning is to uh commoditize time to to

think about your efforts as things that

can be turned into productive value and

the sort of ideal anti-productivity

vision that was being pushed starting

with Odell and then lots of commentaries

during the pandemic was really what you

should be doing is just in an

unstructured way walking through fields

and watching birds and uncommodifying

your life and that this was the tension

between commodifying your time and

watching birds in a park in San

Francisco and this was sort of the setup

that never rang true for me. Uh, you

know, like you, I have three kids. I

have seven jobs. Like, there's a lot

going on. And to me, the opposite of

having a planning system is not walking

through the fields and enjoying birds.

It's chaos. It's stress. It's anxiety.

And, and this is how I connect it back

to my program here on this show, it puts

you into exactly the state where the

digital overlords can dominate. Because

when you are overwhelmed and reactive

and don't know what's going on, guess

what suddenly becomes really appealing?

Well, let me just pull up the phone or

let me just fall back onto like email

and just sort of shoot messages back and

forth. Uh, let me zone out to a streamer

because it's going to numb out the

anxiety I feel. So, I I I thought of

planning

as a key step towards a deeper life, not

as something that was getting in the way

of a deeper life. And there was this

sort of clash that was happening. All

right. So that's my soapbox speech, but

you've been working on this this topic

so practically for years with your

podcast and now with your book and with

your blog.

Why do you think about planning as being

important?

>> Yeah. Well, first I guess it's super

interesting to bring back to that like

Jenny Odell kind of movement because I

do think people get stuck in thinking

about planning as having to be married

to productivity. Meaning if I want to

plan, it means that I'm trying to cram

in as many quote productive things as

possible and capitalism, you know, the

wheels spinning, etc. But that to me is

such a unfair way to characterize

planning because to me, planning is so

much more about thinking ahead of time

about what you want to do in your life

and then making sure that you have

things lined up so that you can do those

things. And for me, if I were to want to

go bird watching in a San Francisco

park, let me tell you what I'd have to

do. I would have to do a lot of planning

to make sure that that could be

accommodated in my life without, you

know, having a kid not get picked up

from an activity or not pay the bills or

whatever it is. So, I guess that kind of

goes along with what you're saying as

well, which is that those two things

don't have to be mutually exclusive. The

the free time, the intentional leisure,

and the planning. And in fact, I think

if if anything for mo many people

depending on their stage of life, the

planning piece is actually required in

order to make the best use or I don't

know the use that fits aligns most with

what they really want to do with their

time. And so that is what has driven my

passion about planning. It's not about

turning out more widgets, you know,

earning more money necessarily, but it's

about fitting in the things that you

want to do in this one life that we all

have. You know, I'm also a huge fan of

sort of the mortality focused

literature, the sort of Oliver Burkeman,

Jodie Wellman type stuff. Um, and that

just for me lights a fire around

planning, which to me also has sort of

two prongs to it in a way. One is about

making sure we're not just going on

autopilot and making sure that we are

fitting in the things that we want to

do. And the other side is making sure

we're not getting overwhelmed by little

tasks coming at us trying to kind of

take a bite into our lives. And by

making sure you're managing all those

tasks and making sure you're

purposefully adding in the things you

want, then hopefully you get to do more

things you want to do, like I don't

know, bird watching a San Francisco

park.

>> Well, let me give you an analysis. I'm

going to not psycho analyze, but I'm

going to analyze you and then you're

going to tell me if I have this right

because I have this theory about

partially why you're you personally are

in a very good situation to be leading

people through these topics. Um, and I I

think it it I don't really understand

your profession. You're a pediatric

endocrinologist, right? A clinical

doctor.

>> But my but I think it's important that

you're a clinical physician because my

understanding in in some sense that's a

that's a very demanding job, but it's

also very structured, right? You have

this sort of uh cadence of appointments

that's like probably pretty standardized

in your practice. Whereas a lot of

people and maybe in the Jin Odell camp

and people in my world, you're often in

like a a more vague knowledge work

environment where there is this sort of

which I this is where I get the Odell

critique. There is this sort of sense of

like an endless knob of productivity

that you can turn that seems tied to

like busyness and how many hours you're

willing to work outside of work. And

there's like a rightful, you know,

negative association that people in like

a email-based office job start to build

where they're like, "All right, enough

of this productivity talk because my

boss just wants me to do emails till

midnight and like enough is enough." Did

it matter that your job had enough

structure that you you could stand aside

a little bit from some of the

maladaptive stuff that was happening in

certain knowledge work jobs. It was I

think smoke screening the importance of

organization and planning because it was

sort of like an orthogonal issue that

also needed to be solved. Am I getting

medicine right there or am I just romant

am I romanticizing? I've personally

experienced both sides because I've had

more like leadership type roles where

the emails are like rolling in and the

meetings and everything is a little bit

more you know kind of like a world

without email but the opposite of that

kind of but then yes the rest of my job

has been very very structured and you

are right a lot of my passion was born

out of a time period when almost all of

not all but like a very large fraction

of my hours were very much accounted for

by others like it was during my

residency training where we had caps at

80 hours per week that we could be at

the hospital, but other than that, you

know, our time was not really our own.

And it made sense to be incredibly

intentional with the hours that were

left. And I guess that is where a lot of

my passion around planning was born. Um,

but you're right that my current life is

is much more around that. Much of my

time is fairly structured and that is

one of the things I love about my

clinical job is that I can go in, see my

patients, write my notes, and kind of

feel like I did everything for the day.

Is it true you had your first kids when

you were still this over overlapped

residency?

>> My first kid was during fellowship. So

the subsp specialty training after

residency.

>> Can I ask you a a brief unrelated

question that is related to the pit on

HBO?

>> I love the pit. You can ask me anything

about the pit. My husband and I, because

he's a vascular surgeon, we like sit

there and analyze every episode um for

correctness and maybe misinformation.

vascular surgeons think that they should

be bringing they're doing too many

things in the ED that they should be

bringing consults in. That's what I

heard is like no you can't don't mess

with that nerve in the hand. You got to

bring down um okay but here's here's a

question on behalf of my whole audience

more important than anything else we're

going to talk about. Can you please

distinguish between

thirdyear medical student intern like

pre- residency first I cannot my sister

is a attending you know ER doctor and I

still don't understand

>> can you just what is the order of things

that happened and then we'll get back to

platty but I got to understand this is I

don't understand which character is what

when

>> well I'm trying to remember like who's a

third year and who's a fourth year like

Javati is she a she a fourth year maybe

so in med school you usually do your

core rotations so that's the very first

year in the clinic your third year of

med school and then the fourth year is

more like subsp specialty rotations. I

don't feel like the pit does a great job

of saying who's a third year and who's a

fourth year.

>> Is that intern yet or not fourth year?

Is that is fourth year the same as

intern or is that post fourth year?

>> So medical school has four years. Then

begins your intern year which is also

known as the first residency year. And

most residencies well the ER residency

is actually four years long. So, um,

sometimes it's totally unclear, but we

know Santos is R2 because I keep saying

it over and over again.

>> Yes. And the the really young doctor in

the first season, I think, was third

year or fourth year. Maybe like a fourth

year. Okay. And then when do you get

called doctor?

>> You get called doctor when you begin

your residency. So, after med school.

Before that, I used to use like an

archaic student doctor.

>> Yeah.

>> Heart or whatever. But yeah.

>> Yeah. Interesting. All right. Well, we

we now we got the important stuff

covered. we can get back to the easy

stuff like trying to manage life in this

chaotic world. Um, all right. So, let's

let's go back then. Uh, you've

>> been thinking about uh planning and

organization for a long time. You've had

your podcast, your blog, and your book.

I think I have that order not quite

right. Probably blog, podcast, book.

>> That is correct.

>> How today do you think about the

elements that have to go into a

successful planning system?

>> Yes. So, in my opinion, and I know it

might differ a little bit from how you

talk about it, but I feel like there are

three big ones. The first one is a

calendar that's completely functional

and shows everything. And in my book, I

refer to that as like one master

calendar. And that can be it sounds so

straightforward, like of course I have a

calendar, but a lot of people are

actually consulting multiple places,

even on a day-to-day level, to actually

figure out where they're supposed to be.

So, master calendar is number one.

Number two is a really robust task

management system. I've coined the term

airtight task management because I want

to communicate that like you know

exactly what's coming in, where to look

for it, how often to look for it, and

where to put it so that you know you

will see it. And to me, that's the part

where you're sort of preventing the moth

eating like things coming at you from

really um getting too much of your time

and attention and you know putting the

tasks in their place where they belong.

And then finally, you need a fantastic

and robust goal setting system. Um, you

talk about yours in like a multi-level

scale planning, and I have a very

similar version of that called nested

goals. It has a couple more levels than

yours has because I I love a month. I

love the monthly level, which you don't

really talk about. Um, but similarly,

you know, you're planning every year and

then every season you're looking at that

yearly plan. Every month you're looking

at that seasonal plan. Every week you're

looking at your monthly plan and every

day you're looking at your weekly plan.

And that sounds so much more involved as

it is than it actually kind of is in

practice. But by doing that and having

like a really clear-cut, purposeful

ritual at each of those time points, you

know that you're going to be integrating

kind of the urgent and what you need to

do in a given day or week with the kind

of higher level goals that you've set um

in more thoughtful planning sessions.

>> Right? So this is fascinating and I

think this is a a key distinction. I I

struggle to communicate this sometimes

as well is that there's there's these

different elements that all go under the

the umbrella of planning. Uh you have

the whole sort of information

organizational aspect of it and then you

have the sort of time control aspect of

it which you're calling like goal

setting system. Um and I think often

people will zoom in on just one piece

could be the like I I have a planner a

planner called a time block planner but

it's not a planning system. It's like

one piece like in your terminology it's

like one of multiple pieces that goes

into a goal setting system that itself

could be large part of a larger planning

universe but there's people who say I

bought my time block planner um so can I

organize my whole life with this thing

and I was like no no no no that's like

you just you bought an exercise band

that's probably a good thing to use as

part of a large health and fitness

routine but just having that exercise

band is not the is not the whole thing

um okay so I want to go through let's go

through these in this order because I

think it actually I think calendar to

task airtight task management to goal

setting system is easiest to hardest or

simplest to most complex. I I feel like

things get more and more complex as we

move down. Um all right so master

calendar when you say shares everything

so you're talking about professional

personal family we need everything in

one place. Are you a digital person? Are

you a Google calendar where you could

have like multiple different calendars

you turn off and on

shocked and everyone is always shocked

but I'm largely paperbased. Um, I have

three kids. I also have like five, not

five jobs, but maybe maybe three jobs if

you count like the podcast is one and

then all my other media stuff and then

my physician job, which is three days a

week. I do work part-time as of now on

my clinical side. Um, but for me, I'm

able to actually have my master I have

it right next to me, my master beer.

Meaning, okay, is every detail of every

little thing in here? No. Meaning there

are blocks in here? This is not going to

show up, but where it just says patients

and I can't like see exactly what the

patients are that I'm going to see

because first of all that would not be

HIPACO compliant and second of all that

would be you know way too much to put on

paper anyway. But I know that when I go

to work I'm going to log into our

electronic health you know system and

see exactly which patients I have to

see. But still this is enough for me to

know this is where I have to be on any

given day. And on my you know kids level

I have a whole section on the bottom

that talk about like where the drop offs

and pickups are. Um,

>> wait. What do you mean by section on the

bottom? This is outside of the flow of

time. It's like at the bottom you have

like kind of like a to-do list for like

listing out drop off pickoff times.

>> That's a choice that I've made. But I do

use a vertical planner so I can see

pretty much everything kind of like

scaled to time just like you would pull

up in Outlook or Google Calendar. But

because I don't always do all the

driving, um, you know, I'm like I have

we have a nanny, I have my husband, I

drive, I have three kids, they're going

in different directions. I kind of like

to still know where all the kids are.

So, I kind of put a row beneath there

where I put all the comingings and

goings of gymnastics and basketball and

dance and all that kind of stuff.

>> So, it'll be like drop off at 3:30, pick

up at So, just like listing it. Okay.

Yeah. Oh, that's interesting. We we've

taken to So, we we're Google calendar

people.

>> Um my wife and I uh because then I have

my work calendar so she can see and I

can see what she's doing. But, we put

the kids uh like family stuff. We put

those as those are like appointments on

there as well. And we'll we'll we'll try

to span the time the driving actually

takes.

>> So like that half hour will be now a

reality of this calendar is there's a

ton of overlap stuff happening because

now everything is on the same screen. So

you know in Google calendar things that

intersect time-wise overlap. So there's

a lot of

>> you can you can hide right like so you

can decide to only look at your bar.

>> You can uncclick it off. Yeah.

>> No and I'm not against digital

whatsoever but you did ask what I use

personally. I think both are fantastic.

I just sometimes people write off paper

kind of thinking like well if your life

is you know complicated there's no way

that will work and like I've been making

it work for a really long time. I do

have very small writing and I enjoy

using paper. So if that does not apply

to you I 100% say embrace a digital

solution. When my kids get a little bit

older as well and you know right now I

kind of have one using um digital but my

two younger ones not so much but I could

imagine us migrating when it makes more

sense for everybody.

>> Could I ask how how large the formatting

is? So is it day per page, five days per

page, like how big are these columns?

>> So the my calendar exists on the weekly

pages. It's like kind of could see on

the video of a Hobonichi cousin planner

which is A5 size. So each column is like

a little more than an inch wide. Um but

it has a very small grid lines and it

goes all the way from you know midnight

to to midnight. So

>> So you can see a whole week.

>> You can see an entire week at a glance.

>> Yeah. Okay. Interesting. And then how

much are you putting non uh non-appoint

things on there? In other words, and

when are you putting those things on

there? So things that are not um you

know, I need to be here, there's a

meeting, there's an appointment, I'm

seeing patients doing these errors, but

optional uh tasks that you're adding

just to kind of keep track of what

you're doing with your time. Is that

>> we're bleeding into task management and

>> and goal setting probably as well,

right? This probably touches on

everything.

>> This is it. So, this is super

interesting because

people love to like fixate on like,

well, is it all in one tool or is it

not? And in my case, it is, but I do

think like this is an important time to

step back and like realize there it's

still performing different functions for

me. Um, and there's no reason it has to

be allin-one tool. But for me, I do

actually do most of my pretty much all

of my shorter term task management on

paper as well. So, I have two places.

Well, we're kind of skipping ahead to

task management, but um when you are

deciding where to put a task, you want

to put it in a place that it makes sense

that you're going to see it at the right

time. You can either assign it to a very

specific time, like you can literally

calendar it in, you can assign it to a

day, and you can do all these things

digitally as well, or you could assign

it to a week. That's a little bit harder

to do digitally, but you can you can

find some workarounds. And so for me,

many of my like day-to-day tasks and I I

use the word task instead of goal here

because I often talk about kind of goals

turning into tasks around the weekly

level. Um but I have a more like a the

eighth column on the lefth hand side has

a lot of tasks that I want to do for the

week. If I have a task that I come

across that isn't that urgent, then I

might assign it to a future week. So

well, next week doesn't have anything,

but the week after that has a couple of

tasks. Or I may actually stick a task up

at the top of a day if I don't have a

specific time slot for it, but I want to

assign it to a specific day. And what I

do with this is so arbitrary. Like you

can do the exact same thing in Apple

Notes or to-doist or to-do or things

like the actual place, the vessel where

you're holding these things is going to

be unique to what your style is and how

often you like to use devices versus

paper, etc. The important thing is

defining for yourself where these

holders are. Where do you put tasks that

you want to see for the week, but you

don't want to, you know, assign to a

specific day? Where do you put a task

that you know you're going to see at the

beginning of each day? And where do you

maybe put a longer term task that you

don't want in your face for a given

week, but you know you're going to want

to see later? Let's take a quick break

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first order. All right, Jesse, let's get

back to the show. Well, okay. So, let's

move on to airtight task management. Um,

so the word airtight here, this is a

reference to like a David Allen style

full capture. Don't not in your head and

not somewhere where you're going to

forget that it exists.

>> Correct. And I make a big emphasis on

making sure that you are very aware of

where tasks come at you because it's

usually for most of us not just one

place. You might have text messages,

your WhatsApp chat, your email, your

work email, and your personal email.

people that just like stop you on the

street and tell you they want to do XYZ.

And you need to have a really thoughtful

way to make sure that each of these

pathways has a pipeline that like makes

sense. Like you're checking them enough,

but not necessarily all the time. And I

actually kind of teach people that every

given box that you might receive a task

in might have its own cadence that makes

sense. So maybe you look at the sports

team app twice a week, but you only look

at your email um three times a day or

something like that. Like I'm making

that up. And then to be very clear about

once those tasks come in, where are they

going so that you are not going to lose

track of them and you see them at the

right time. Sometimes the answer is to

just do the task. You know, something

comes at you that's one minute or less.

You just get it done. Um but then a lot

of the times, uh the answer is to put it

into whatever system you're using for

task management so that you see it at

the right time.

>> Okay. And so your vessel agnostic, but

the idea is you have a singular vessel

that when you check these various

pipelines

uh stores the tasks and then there's a

separate sort of system or cadence for

taking it out of that vessel and getting

it onto your weekly plan, your daily

plan. Is is that more or less right?

>> Yes. I mean sometimes there's not really

like an extra step there. Like if the

vessel is your text messages um and

someone sends you a task there, it's not

like it's going to some holding place,

you would you would then, you know,

let's say you make sure that at the part

of your processing, and I know you talk

about processing at the end of every

day, either with a TXT file or however

they're doing it, but as you're

processing the end of each day, you take

any text message that's left, you leave

it unread if it's something you have to

handle, and you put it straight into

whatever tool that you are going to use,

whether that is again the to-doist app,

your planner, whatever, whatever. ever

it is. And being very careful about once

you've chosen where these tasks are

living, you cannot be swapping around

and using multiple storage vessels,

you've got to be like, "This is my one

place and you have to have rituals that

include looking at that place." And

again, that seems kind of obvious, but I

get a lot of people, they're like,

"Well, I put some place some stuff on my

monthly and some my week." I was like,

"Well, when are you looking at those

pages?" Right? You want it to be

somewhere that you're going to be

checking at the appropriate cadence so

you know you're going to see it.

>> All right. So, what do you use right

now?

>> Yeah. So, right now, um, I do a few

things. So, if something comes at me

like randomly throughout the day, I do

exactly what I just said, which is that

I will text myself or email myself and

leave it unread. And one of the things I

do at the end of every single day before

as I'm shutting down is to make sure

that those anything that's left unread

is captured. Um, I do that with WhatsApp

as well. Like if I get something from

school and I'm like, "Oh, I need to deal

with that. that then needs to go into my

system that gets left unread and that

inbox gets checked by the end of the

day.

>> You said unread emails and unread

messages

>> or WhatsApp messages.

>> Okay. So that's what that's going to be

during your processing step what you're

looking for. So if you if you think up

something just you know ex nilo like oh

god I forgot I need to like start

planning for X. You might send yourself

an email.

>> Yes.

>> So that it'll be there unread

>> and I'm leaving it unread because it

means it hasn't been processed.

>> Okay. So then when you process you

process when end of the day

>> end of the day by end each day I want to

see no unread texts no unread WhatsApp

messages and no unread emails doesn't

mean I've like archived them or dealt

with them but they are they're not black

>> so then what are the I don't even know

can you send yourself tech I'm so tech

bad

and then you can actually leave them you

can like I don't know you swipe over and

you click the thing so it so it shows

that it's unread my fingers know how to

do it my my brain can't describe it

>> there's some sequence of things I do all

day long which I can't actually tell you

what it is Um, okay. So then what are

the options then? So I this is

fascinating to me. I I like to the the

nitty-gritty here. Um, you're at the end

of the day you're processing what are

the options for what happens to the

information in like one of these unread

emails or text messages.

>> Yeah. So that is where this like where

my task management system comes into

play which again tool agnostic but I

largely use my planner. So I'm either

assigning it to like this week if I need

to get it done this week. I'm assigning

it to a future week or I'm giving it a

specific calendar slot within my

planner. So that I know on Wednesday I'm

going to wake up and be like, "Oh, at

10:00 a.m. I said I had to sign the kids

up for that camp that's going to sell

out in 30 seconds. Perfect. I'm going to

see that that morning. I'm going to know

about it and then I'm going to do it."

>> But so this is interesting. So your your

main place you uh you store the task.

It's your planner itself. It it it

exists somehow tied to time. Be it at

the weekly scale or the daily scale or

in like a particular slot.

>> I put almost all of my tasks and even my

goals tied to time. I mean, that's kind

of how I link. I call them goals kind of

at the larger time horizons, like year

or season. And I call them tasks when we

get down to the weekly or daily level.

Um, again, they're not always

specifically tied to time, but they I

mean, I guess they kind of are because

even if I'm putting it in a future

week's time frame, and even if I haven't

entirely committed to dealing with it in

that future week, it means I'm going to

see that task on that given week. Um

because again just like the day and I

have things that I want to make sure I

process by the end of the day. I'm never

going to exit a week without doing

something and this is actually a very

key point of task management to

everything I've put there. It doesn't

mean I've gotten them all done but I've

either decided you know what I don't

want to do that anymore. I'm crossing it

off or I'm migrating it. And I actually

this is kind of comes from the bullet

journal world but I tend to write a

carol.

>> Yeah. Like an arrow through it and then

I move the task to somewhere else.

>> Oh interesting. Okay. And then do you do

that uh at the end of each day? Are is

that when you're looking at tasks that

were assigned to that day you didn't do

or is it more at the weekly cadence? You

look at the whole week of things that

were assigned either either to the week

or to particular days that didn't get

done.

>> So I do make a list for each day as

well. We didn't even get into that. Um

but I tend to do the exact same process.

Again, this is going to be much much

quicker on a daily level. Maybe I had

six tasks I assigned myself. There was

one I didn't get done. But as I'm doing

that sort of like end of day processing,

if I have a empty checkbox on my

planner, I better figure out what I need

to do with that task. Um, if I miss a

day here or there, usually I'm able to

kind of catch up by making sure I

haven't crossed it off the weekly. So

there's kind of multiple layers in

there. Um, but in general, I do that

processing really at the end of every

day and as I move forward to the next

week. Something that's interesting to me

about this approach is it it may be a

way around a real issue I have and I

think a lot of people have which is task

system aversion which is this notion of

if things are going into a task system

it could be a singular vessel in a very

good program and things are being stored

and categorized in there's a sort of

activation energy that builds up

especially if like you're stressed or

you're overwhelmed or the the week is

going difficult and you're like my day

is full like I often have days where uh

you know because I work within a very

fixed amount amount of time where I'm

constantly racing the clock. It's, you

know, I got to get this article in.

These edits are due. There's these

urgent things or whatever. And the

activation energy of like, let me now

load up a task system and read all these

tasks and confront all that I have to do

and like I don't have time to do

anything in this day and I don't want to

do that and then I fall out of the task

system for multiple days. So if you're

just on your C the one tool I always say

like everyone uses at least this one

productivity tool or organization tool

is a calendar because you can't remember

when your dentist appointment is without

it. So you know you're going to look at

your plan like the the the weekly like

what am I doing today? What am I doing

this week? Like that will get used

because you have to see and so having

the task in there means there's no

separate activation energy. This is huge

and it's actually like why David Ellen

stuff doesn't totally work for me. And

it's what you said. It's like that

residue of like I don't want to look at

all the things I want to do. I don't

want to look at like six weeks worth of

accumulated stuff when I know I have

like two free hours on a given day. So

like that's exactly that activation

energy. I haven't heard it described in

that way. But I think you're right. For

me it's so much less stressful to be

like, okay, what's on today? Oh look,

today's really crowded. Let's only look

at that weekly list. We're not looking

beyond that and then like selecting

maybe one thing if that's all I have

time for. Creating my new list for the

day and then never looking back for the

rest of that day until I you know maybe

when it's time to do monthly planning

I'm going to look go larger scale. But I

designed this system in part because I

am like you stressed out by the idea of

seeing everything I need to do more

often than I actually need to

>> and and things that are non-trivial in

terms of time but are still in that task

category. I mean, in my experience, the

way those things get done is they live

on they they're on your calendar for the

day. Like, that's how it happens is

like, no, this is what I'm doing at 12

is I'm going to the dry cleaner and then

calling like whatever information that

list that exists in list is not very

it's much less actionable, but okay. So,

are you also here's the other idea that

I'm just thinking about ideas that are

catching my attention is like, oh, wait

a second. Yes, I think there's there's

there's something here that's like

explaining an issue that I want to

solve. Because when I'm thinking about

my task vessel, I'm using primarily

things three right now. One of the

things I do is like I'll often there'll

be like a bigger project and I'll I'll

generate as I come up with like steps

and tasks related to that project. I'll

be adding them to this list and I'm

like, okay, I can't have I couldn't put

all of these on my calendar like I have

hundreds of tasks in there. But it

sounds like and tell me if I have this

right. what what you would say is you

shouldn't be you're expanding too much

of the goal and the practicality too

early like that project should exist as

a goal and when we get to your goal um

setting system which we'll do next I'm

there's a cadence in which those goals

or projects generate tasks for the near

future and that like probably you would

say if I have this right like yeah your

list are too long because you're you're

unfurling too much from these things

you're working on. You don't need to do

that in advance. You need to see what

the projects are. Look at your week and

figure out what am I going to try to

make progress on this week with these

projects and what does that actually

look like practically and let me put

those task for the week or for

particular days. Is that

>> Yeah. And there's nothing bad I don't

think about keeping future potential

project steps somewhere convenient. Like

for you it might be things. For me I

love using

>> I'm looking at my list while you talk by

the way. Now now I'm thinking

>> fun we can experiment with like an

actual thing that you wanted to do. Um,

like there's nothing wrong with having a

receptacle for ideas. Like, um, I'm I'm

imagining maybe you have like a

renovation list and there's a whole

bunch of things on there, but the truth

is you're not assigning yourself all of

those things at once because there's no

way that fits in Kalen Newport's

lifestyle when he's also working and

dealing with kids from day to day. So,

that's exactly right. You might have

that as a reference, but you're not like

putting on your plate all of those

things until you've decided to put one

of them on your plate, if that kind of

makes sense. And that might happen, not

to skip ahead, at a higher level goal

setting system. Like maybe you're

planning your summer and you're like,

you know what, now is the time. I'm

ready to tackle that bathroom rena. And

um maybe I'll just put like begin

bathroom rena on the list. And then on

the monthly level, you think about,

well, what piece am I going to do first?

I'm going to get quotes. And then again,

that kind of generates more smaller

tasks at the weekly level where you're

like, oh, let me text my friend and find

out which contractor he used or

whatever. So things will trickle down,

but the idea that you kind of need to

have

all of them assigned to you as tasks

when they're not really happening yet, I

find that stressful. And again, I think

that's partly why I built the things the

way that I did.

>> Well, like I I just noticed looking at

my list now that there's like multiple

pretty technical tasks related to one of

the courses I'm teaching right now. Um

because I, you know, at some point I was

like, "This needs to get done. and I

need to post this the syllabus for the

second half of the year and I need to

you know check in with the TAs on this

or that right I'm kind of like putting

these things down so that it's not just

in my head but there's also a notion of

like well if you trust yourself that

there's just like a standing project for

the semester which is the course and

like part if I just at the beginning of

each week was like where am I in the

course what's coming up what needs to

get done this week I'm not going to

forget though like I mean I I will be

able to generate those things as the

time comes up most likely Right? I said,

"Okay, I'm looking ahead at this week."

You know, like I need to the rest of my

syllabus should probably go up like

we're getting towards the end of it. So,

let me uh schedule that for this week or

I don't need to the TA thing maybe is

relevant when there's an exam to grade

or something like that. So, there's some

>> there's some interesting balance here.

>> Some sort of system and I'm sure you

already do something like this where

you're like looking ahead at your week

and that's often going to generate tasks

that kind of like make sense for what's

coming up. So, you know, part of

planning at every time horizon, and this

even includes the day. Um, you're not

just looking back at like, well, what do

my previous self want to do? You're

like, oh, what's actually coming up

ahead? Is there anything associated? And

you being Cal, you you would do it. You

you can trust yourself. Like, I'm sure

that you would look ahead of the week

and be like, oh, you know, we have this

coming up. And if you had to do

something that's longer range, maybe you

would live your leave yourself some kind

of a a note prior to that. But I feel

like if these are things that are just

like generally part of your job and your

your flow anyway that yeah, you'd come

up with them and you probably don't need

to

have them somewhere separate. Now, if

having a list of everything is just

helpful to like have a reference, I

don't even know if I would call it part

of your task management system almost

just more of like a a collection or

reference then that that could make

sense. Um but you haven't like truly

assigned it to yourself. So let me tell

you my goal setting system and then I

want to hear let's do there's a CS term

we'll do a diff that's it was an old

command line program you you give it to

text files and it would highlight

exactly where they differed so it was it

was like how you would tell if there's

like changes to source code in a shared

code repository this is the type of

stuff people come here for they want

>> this is the type of stuff where I'm like

okay

>> Linux command line interfaces

>> um all right so my multiscale so now I

know my multis scale planning is what

you would call goal uh goal setting

system Nested goals. Yes,

>> nested goals. All right. So, the way I

run it is I typically have like a

semester or quarterly check-in like what

are the big things that are happening

this season. I mean, they roughly

correspond to my academic semesters

>> and I write it out freehand. It's in a

text file. It's like, hey, this is I

don't want this to be too structured

yet. Um, so it'll be things like I'm

teaching this course and here's type of

things I have to keep in mind. um where

am I on like if I'm writing a book like

I'm really looking to be you know done

with uh submit the manuscript by

December which means like I probably

need to be doing a chapter a month and

so it's sort of like thinking through at

a high level like what's happening at

this scale then and this has sort of

been my my secret sauce that I think you

were one of the few people who actually

talked about this scale as well is

actually for me is the weekly the weekly

scale is critical um because it's where

I interface that plan in the calendar

and this was always this was like a big

thing for me um I look at that. Okay,

what are these things that are these big

picture goals? I look at my task list,

which now I'm learning are probably too

detailed. And so this could be a lot

easier. These could be like more stakes

in the ground instead of like long list

of things. Um I look at my task list and

I look at my calendar, which at this

point is really just going to have

things that are appointments and

meetings. So I can see like what's the

layout of my week, when do I have time,

when do I not have time, which days are

busy or not. Um are there this was a key

innovation. It came at some point I was

like, "Oh, this is the time to look for

big win changes. If I cancel this one

appointment Friday at 11:00 a.m., that's

going to free up like 6 straight hours."

And so, like, I see now I'm going to be

frustrated when I get there. I'm just

going to move that to like another day

or something like that. And this is when

I start putting stuff on the calendar

that's not meeting or appointment. So,

now I'm like, I want to make progress on

this goal. I'm going to now block time

on my calendar like a meeting or

appointment for that particular goal.

Like, I'm going to be writing this day,

this day, and this day. I'm going to

work on this like project this afternoon

and now I'm starting to protect time at

that scale. It's also where if there's

key tasks uh I'll start when am I going

to get these done and I'll start

actually adding them to my calendar. So

by the end of my weekly plan the

calendar is like a lot fuller. There's a

lot less space in it but only some of it

is actually meetings or appointments. A

lot of it's what I came up with and then

I go to the daily scale. Every day I

make a time block plan for the day. Now,

what I found is if I don't time block

plan, it's uh unless it's a writing day

where it's like all that really matters

is I write as much as possible, like I'm

on deadline and then it's just survival

mode for everything else. Outside of

those days, uh a lot of that day by the

time I get to it, the calendar is pretty

full because I've been making use of it.

But I transfer that into a daily time

block plan and I fill in the remaining

gaps in the workday for what do I want

to do during that time? Um, and then I

execute off of the daily time block plan

for the day as opposed to like list

reactive method. All right, so that's my

goal setting system. What's our diff

there? Where are the places where we

differ?

>> Where do I do things differently? So, I

would say I'm I lean a little bit less

heavily on scheduling things. Um, which

is interesting. So, like when I go I

actually will also add that I love to

have a monthly level as well because I

have actually figured out that I'm going

to pull my little monthly out. And yes,

this one's analog, too. My schedule's

very weird and varies a lot from month

to month because I have weeks where I'll

be entirely on call, entirely clinical,

like can't do anything for the podcast.

And then I'll have other weeks that um

maybe I've taken like time off to do

work for the podcast. So, like my months

can be incredibly variable. So I

actually have a step in here even on the

monthly level where I'll look to see how

many like kind of work days do I have.

When I say work days I mean like how

many clinical work days and how many

work for myself days and how many days

is the family going away etc. Um and

that's how I will kind of decide how

much I want to take on from a creative

perspective because that's the lever

that kind of moves the most. Um can go

high on some months and low on other

months. Um

>> so monthto month kids there it's not

just week to week. You're like, "This

month might be a clinical month."

>> Correct. Or maybe not the entire month

is clinical, but like

>> but like whatever. That's the like the

ca this the the feel of this month is

like I'm actually doing a lot more like

in office stuff. It's so Okay.

Interesting.

>> Correct. Like January, I had lots of

days that I could play around and work.

And then February, we had a week of

family vacation. I had something medical

going on and I had a week of call. So

that left me like I don't know. This is

like one out of four days is today that

I actually have time to do anything. So

that kind of helps me take a larger

overview like how much can I actually

take on here? Do I even want to add

anything kind of new over the course of

the month and then that kind of informs

um you know the bigger things that I'm

taking on and I actually do usually

create a list for the month that I look

uh look towards as I'm planning each

week and then my weekly process is

similar to yours but I don't tend to do

as much of what you're saying which is

where I'll say oh I have to write this

I'm going to like give it a specific

time slot. I tend to just sort of look,

okay, I have this many hours, I have

this many projects, and on a day-to-day

basis as I'm planning my day, that is

when I'll actually commit to like what

fits where. And that's just personal

preference. I don't like to feel

entirely locked in. Like I think maybe

it is kind of a backlash to on my

clinical days, every minute is spoken

for. So on my nonclinical days, I want

to be like, do I want to write from 10

to 12 or 1 to 3? I want to make that

decision that day. And I do purposefully

make it on that day. kind of my own

version of time block planning and think

about what fits where, but I don't go

ahead and kind of preschedule it

throughout the week. So, my weekly

schedule um aside from the clinical days

actually probably looks less full than

yours does um when I'm going to the

daily level and then it's on the daily

level where I say, "Okay, which of these

tasks am I selecting and where do I

actually want to fit it within the day?"

But otherwise, I think our systems are

have a lot of parallels. I think I I

mean I prefer that if my issue the

reason why I have to do the the way I do

it is that if I don't protect that time

like Monday morning god everyone comes

and takes it. So that's my main issue is

like I'm like I if I say I'll figure out

Thursday when I get to Thursday everyone

in the world wants that time and by the

time I get to Thursday like the time to

work on these things uh is gone. So it

helps me basically helps me say no to

appointments. But I had this

conversation when when uh Oliver

Burkeman stopped by earlier this year

and we were you know talking about

various things. We he was like here's he

he was like here's my ideal schedule and

I agreed with him. He's like the ideal

schedule just from like human nature not

fix a particular job would be kind of

deep work in the morning like you're

working on something important. Um, and

then when you're done, then you're like,

based on how much energy I have, like

let me like do a few other smaller

practical things more or less depending

on my mood and then be done. And I was

like, Oliver, I'm with you, man. Like

that would be that's my rhythm as well.

Unfortunately, the world has conspired

to prevent that because I'm not a

full-time writer. Uh, okay. So, that's

interesting though. I get that. Like I

also I get stressed out by my calendar

and and I think this is but and I feel

like I have to do it because otherwise

it's just it's the chess game's too

complicated I'm playing. But I think

that's more a problem with the game I'm

playing.

>> Well, I think again you're an

academician academic. I don't know.

Sorry. I don't even know how to

pronounce the word. But um with certain

careers, people can dump things on your

calendar if they see open space. And I

can see why that would really lend it to

like no no no this says writing so don't

you dare put anything there. I am lucky

in that um well my patient time is all

up for grabs and that will get as filled

as it get filled but my time for myself

I'm really the only one who could dump

stuff on there. Um that's just how I've

designed things and I think that allows

me to be a little bit less scheduled.

>> I'll tell you my big innovation of this

year now and I can I can get away with

this now because like I'm out of

promotions to get you know I'm a full

professor been tenured for a decade.

like there's no there's no no nothing

else that you know for me to worry about

upsetting people about. I introduced the

notion of a studio day

>> and for me it's Tuesdays. Um because now

that I'm doing a lot more digital ethics

and not sort of hardcore computer

science I was like look the this podcast

my newsletter this is a big part of like

my work as a public intellectual on

technology etc. So studio days as I just

tell my employer um I'm not available on

Tuesdays. I don't I don't do meetings on

Tuesday. This I'm in my studio. I'm

recording. I'm writing and this is I've

consolidated it this one day, but it's

like I'm reaching millions of people and

this is important and I'll ask for, you

know, uh forgiveness instead of

permission. And that's been like a huge

that's been a big boon actually. It's

like yeah, I just don't I don't do

things on Tuesday and people grumble and

then they have lives and they they stop

caring because it's not that interesting

to them.

>> That totally makes sense. And I feel

very privileged that I'm doing this not

on your studio day, but thank you for

accommodating my patient schedule.

>> Oh, I'm I'm happy to do things on other

days, too, but like I'm just don't put

like I have to go into I have to go

teach today, you know, that's which I

which which I do enjoy. Um, okay. So

then let's talk about seasonality

because this is something in your book

best laid plans, the book, not the

podcast best plays. Um there's a lot on

this and I think we're like very

congruent on this idea of moving away

from the notion of just year round no

variation to your it's just like you're

turning the crank at like a certain

level of intensity and February feels

the same as June feels the same as

December.

>> Um talk to me about varying rhythms,

pace, workloads over time.

>> Well, first of all, I just love the

concept of seasons in general. And I

don't know if that's partly because I

live in South Florida and I don't really

get to experience them, but I just like

to really really like think about them

and think about how my year makes sense

divided up. And I actually kind of talk

about different ways that you might

think about dividing up your year other

than the traditional quarters or even

trimesters if you're an academic. Um,

but I really do like to take a very

purposeful like almost half a day kind

of planning session four or five times a

year. For me, it's five because I like

to divide the year up into five pieces

and think about what do I want out of

the upcoming season and not to assume

that, you know, season C is going to be

exactly like season A. For me, um, the

first season of the year is like January

1st to spring break and that's usually a

very go season. And then we kind of have

a very kid focused season from spring

break until the end of the year when we

have all that like May stuff and every

single kid is in every single

competition, whatever. And then summer I

treat as much more like let's just be

lower key do fun stuff. Um and by the

way I didn't mention this previously but

I think one other place we differ a

little bit is I am very passionate about

not just planning my work but planning

the fun stuff like planning the

gettogethers with friends and the travel

and the massage or you know whatever it

is that I'm trying to build into my life

to make it more fun. And so summer might

be a time that I have like a lot of fun

planned and it's just like a looser time

period. Then we have back to school

which has that rhythm of like okay kids

are going back. We're in our routines.

I'm also because I'm in the planning

world tend to be really really busy in

like January and back to school season.

So that kind of makes sense. And then I

have what's called reflection season

from November 1st to the end of the year

where I just feel like the world takes

on a different pace. It's a little

celebratory. everyone's reflecting and

um I just like to like acknowledge that

as having its own energy. So yes, I'm

super super big into a like

acknowledging the seasonal flows and b

like purposefully setting time to think

very hard about what you want each

season to be like in advance of that

season.

>> So wait, so your quintiles are um so you

got like new years through spring break,

right? Spring break to the end of the

school year

>> like end of school year. Yeah. Period.

Which I agree with you. kind of like I

think of it's a time when it's coaching

time for me too. It's like I I coach

multiple different things. Um summer

>> summer

>> then back to school to like Thanksgiving

>> and then until Halloween and then

November 1st to December 31st to me just

feels a little bit different.

>> Well, but you got like holiday Yeah. And

you have uh there's like the

Thanksgiving holiday. There's going to

be like the Christmas holiday. There's

going to be and people wind down. What I

think a I love it. Um, and I think

similarly, and I think what's important

here though is because a lot of times

when I talk about seasonality, you

probably get the same thing. People will

push back because they'll say, "Well,

like my job isn't seasonal." But like

this is true for you, right? Like

nothing about pediatric endocrinology

changes in March versus January. But I

think what what's captured by the way

you talk about it is so much of the

feeling of your day and what you're

focusing on busyiness like expands

beyond just what you're doing in your

job. is what you're doing on the

weekends, in the evenings, on the day

that you're not in the office. And

turning the knob on those things you do

control is actually has a much bigger

impact than people realize that it's not

just I can't take time off of work in

this, you know, the summer, so I can't

have a seasonality. Like, well, it's

completely different what you're doing

with your time, even outside of work.

And then my argument, you can't do that.

I in your job, I don't think this would

work, but in like a lot of knowledge

work jobs, because it's a lot of it's a

little more BSE. um you have like a lot

of give and you can really turn

intensity up and down is something that

I I'm often telling knowledge workers in

general because the job is so amorphous

and there is no just like here's you

know here's a list of things that you're

working on and here's your prog it's all

like email and meetings or this or that

and you can often get away with like oh

I want to turn things down in the summer

and you could do it for a couple months

and no one will notice if you do it for

a year they'll eventually notice but

you're just like taking on less things

and moving slower and then you speed up

in other times so I think people have

way more control over the rhythm of

their life than they realize.

>> Have a totally structured job. For me, I

get around that by taking more vacation

in the summer. So, you know, many jobs,

even if they're extremely structured and

yeah, I can't get away with, oh, let me

see 75% of my patient volume in July.

Like, that wouldn't fly. But I can take

two weeks off and like save my vacation

time for those times when I want things

to be slower and then maybe take on a

little bit less on the creative side and

then kind of create that slower rhythm

for myself.

>> Isn't this like the the people who do

this to the most extreme? Do I have this

right? There's like it's like uh er

doctors who sort of travel, right? And

it'll be like, okay, I'm going to come

>> spend three months at this hospital in

Boulder so that I and then I'm going to

ski for 3 months. And they really got

that locked in, right? we get to shift

work.

>> There are definitely certain professions

who either have tons of vacation time or

tons of flexibility or there are a lot

of doctors these days that will do like

locoms work. So they could decide that

like they're going to work their butt

off in March and April and then like not

at all for two months. So yeah, that

would be extreme version.

>> Yeah. And and it's it's all like the

pit. This is

>> it's all Yeah. Everything I do all day,

it's just like that.

>> Everyone is super reasonable like on the

pit, right? That's just every doctor's

experience where people just talk slowly

and quietly and are just very

reasonable. It's never chaotic at all in

the ER. It's very peaceful and Yeah.

>> Yeah. Just it's it's very peaceful. Um

Okay. I like that then. Okay. So, we we

we agree on the seasonality. All right.

So, to pull this together for people, um

can we build I want to build an on-ramp.

So, like for a typical member of my

audience might be they've messed around

with individual type of tools you might

use in this conversation. They've had a

to-do manager. They have a calendar that

they they sometimes use. They've used a

time block planner and then stopped

using a time block planner. They have a

task list they haven't looked at in a

month because it stresses them out, but

they they're they're liking what you're

saying and like, okay, I think I'm going

to be less susceptible to being pushed

around by big tech and distractions and

numbing if I can take more intention

about my life knowing now as we talked

about it. Intention might be like I'm

intentionally slowing down and then

speeding up here and it's not just it's

not productivity. It's not trying to

increase the amount of work. How do we

onramp? Because we talked about a lot of

things. So, how do we onramp someone

beyond the obvious answer is read

Sarah's book. I was going to say you buy

best laid plans and you read. No, I'm

just kidding.

>> Which I blurbed and it's a it's a great

book. I mean, it really walks through

all these details, lots of examples. Um

and and you can kind of pick and choose.

I feel like in your book there's though

you don't do it explicitly. Um there's

sort of like here's what's key and then

here's like a little bit more advanced

things you can add on and so like the

reader already has a system can plus it

up but like the new reader.

>> Yeah. So, so how do we onboard the new

>> the the newbie to planning? So, I would

just focus on those three things that I

talked about. Like, do you have a

calendar that makes sense where you're

really able to see what you have to do

each day in a way that makes sense to

you? Do you have a task management

system that works and it enables you to

see what you need to see at the right

time? And are you checking your various

inboxes in a thoughtful manner versus a

when things come at me manner? and how

are you organizing your goals both

larger scale and smaller scale and

adapting some sort of it could be a bare

bones version and by the way the tools

really truly don't m like I could do all

of this in a binder in Apple notes in um

on paper on like a really in notion and

a really fancy system like there's no

specific tool but to have somewhere to

have rituals around setting larger scale

goals whether you're doing the yearly or

seasonal level and then also ways that

you're going to bring that into the more

practical timelines. So a way of looking

at your seasonal stuff every week, maybe

incorporating monthly in there and then

day-to-day assigning yourself the task

that makes sense. So I think that would

be my sort of like bare bones minimum

calendar, understand your task

management and have some kind of larger

and smaller scale way of looking at your

goals on a you know daily or weekly

level plus seasonal or yearly. That

would be that would be the most bare

bones version.

>> And that latter piece requires a thing

to write the things down in. Right? So

this the latter piece of like I want to

look at the the the monthly scale and

the seasonal scale for you that's a

notebook and it's a separate notebook

than your planner but you need somewhere

where you're and it could be a Google

doc it could be a text file you need

somewhere you're taking

>> people have done like a lot of people

that I've worked with have had really

cool systems and even just like Google

Sheets where things are actually very

much like you know they'll have a whole

page for the year and then you can

actually tab it and separate by seasons

and they have different categories of

their life all colorcoded. Um, so yes,

you do have to capture all this stuff.

The medium in which you do that doesn't

really matter, but you're going to have

to commit to something and continue to

use it and to look at it. Um, and I

usually also talk about creating rituals

that make sense for the time scale. So,

if you're planning the year or the

season, you want to dedicate like a good

amount of presents and time to that. So,

you're going to really want to clear out

an afternoon or for the year. um Laura

Vanderham who has been on this show

before I believe as well. She and I host

a like live planning retreat that lasts

two days. And I'm not saying everyone

needs to, you know, come to our retreat

specifically, but um we do not run out

of things to talk about with our

participants in those two days for

planning the year. So really giving

yourself the gift of space um when it's

a larger time frame to think about

what's coming up and what do you want

out of that time frame makes sense. And

then when you're going to the day, you

want something very, very quick.

Obviously, we can't do a two-day retreat

every day, right? But we should have

things kind of laid out so that you can

look at your calendar, which is

organized, look at your week, which has

already been thought through, and select

your task for the day in like 5 to 10

minutes and be done with it.

>> And then let me finally, I have to rope

you in, as I do with all guests, into

some sort of AI realism rant because,

you know, this has been been my

correcting the narrative on AI has been

a big part of my work recently. Um, I

want to rope you into my side on this

the intersection of AI and productivity

because I feel like there's this, you

know, tech people aren't the best people

to talk about organizational systems

because what makes a tech person happy

is like complexity and pieces fitting

together and whatever, but they've

really been pushing this this idea that

oh, the missing piece in people being

organized could be solved by AI. And it

really doesn't seem to be the issue

based on like our whole conversation.

The issue is not when I am looking at

what I need to do, understanding it,

figuring out priorities, figuring out

what I should work on today. We're

really good at that. Like our brains

have embedded in it all of the relevant

information. What's coming up,

importance, how you're feeling, health,

other things that's happening. That's

not hard at all. What's hard is

consistency and capture. It's sticking

with a system. um maintaining

intentionality instead of just falling

back into like let me just be reactive

because like I'm exhausted and none of

that's helped by AI. So I don't know can

I can I rope you into my rant on this is

that that

>> I am always up for an AI rant. Um so

that's totally works for me. Um yeah I

just don't want to give some large

language model like that control over

what I do all day. I mean I want to be

the one selecting my tasks. I um one of

my biggest and again I'm not a techie so

I don't understand like the inner

workings like you do but one of my

biggest concerns about AI is that it's

giving power to someone else that I you

know I'm not consciously giving so even

like as simple as oh let me have AI plan

my vacations for the year then I mean

who's not to say that like various

places haven't like paid the model to

suggest some things versus another or if

we're not there yet we're going to be

very soon so I mean for me life The most

precious thing of life is our time and

our relationships. And I would like to

maintain control over that myself. And

so I want to decide what goes on my

calendar. I haven't I'm not saying that

AI tools might not be helpful for some

people. Like you know there are things

like the skylight calendar and I think

some of these apps where you could take

the soccer schedule and it will you know

scan it and add those events to your

calendar. Like those kind of wrote tasks

see being helpful. But in terms of

selecting what I want to do with my

time, I would like to leave computer

algorithms out of that personally. And I

think um most people probably don't want

to

live a life that was just suggested to

them. They want to actively choose what

they're going to do. That's kind of the

planning in the first place.

>> I've never seen someone be stumped by

looking at their calendar and their

to-do list and be like, I don't know

what to do next. What I I need someone

else to come tell me. I've never seen

someone stumped on that. That's not that

not that hard decision. All right, sir.

This has been fantastic. Um, I want to

make sure people know where to get more

of this information. So, you have two

podcasts. Would tell us about both.

>> I do. So, the first one is the one

that's more planning adjacent. It's

called Bestlaid Plans and I literally

describe it as all things planning and

planning adjacent. That one is just me

with the occasional guest. Cal has been

on it before and I will be having him on

again. Um, the other one is called Best

of Both Worlds and that is done with

Laura Vanderkin. We co-host it together

and that's about making work and life

fit together. Um, she's an awesome

writer and time management guru. So, we

make a fun team there.

>> And your book, Bestlaid Plans, that what

that come out in the fall when not too

long.

>> Uh, December of 2025 called Best Plans,

a simple system for living a life that

you love.

>> One of Amazon's best non-fiction books

of the month, right?

>> Yes. It got chosen for December. It was

like a big shock. Um, people are like,

"Did you pay for that?" I'm like, "No."

So, but that was a really fun honor. And

it it says like editor's pick on there.

Um, of course you can get it at anywhere

other than Amazon as well, but that was

kind of a a fun thing.

>> Excellent. All right. Well, Sarah,

always a pleasure to have you on. Thanks

for getting the weeds with us. I think

this type of thing is going to be

helpful for a lot of my listeners who

you got to take control of your time. If

you don't, Big Tech will happily take

control of it for you. So, this is the

the first step. Um, I'm sure we'll be

talking again soon, but thanks as always

for coming on.

>> Oh, thank you so much for having me on,

and I very much enjoyed talking about

the pit. All right. So, that was my

discussion with Sarah Hart Anger. Um, I

looked it up. I I was on the show,

Jesse, so it's worth people going back.

I also years back, I think we had Sarah

on our show.

>> Yeah, we did.

>> Yeah. So, sort of a a long-term friend

of the show. I love geeking out about

planning systems. To me, the key point

that prefaces the whole discussion

because I think her advice is spot on. I

actually picked up some ideas there that

I think are important. But the key point

that I think ties here the whole

conversation is that Sarah did not like

to associate the word productivity

with planning. She like that's two

different things. Productivity is about

I don't know professionally you're

trying to increase the amount of

something you produce and like that's

that. But what she cared about was

controlling your time. How how do you

have a say over what you're doing with

your time so you have control? Uh I

often use the term internally attention

shaping. How do you shape your own

attention so other services don't? And I

think that's really useful. If we

separate planning from productivity, we

realize like, oh, this is one of the

tier one skills, not just for living a

deep life, but for pushing back uh on

the digital distraction. So, very good.

It was good to have Sarah on the show.

Let's take another quick break to hear

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