Deep Questions with Cal Newport - Ep. 268: Stoicism and the Deep Life
Episode Date: October 2, 2023Stoicism seems to be all the rage at the moment. In what ways is it relevant to our question to live deeply in a distracted world? And in what ways is it not? Cal takes a closer look at Meditations by... Marcus Aurelius and discusses his relationship with the philosophy more generally. Below are the questions covered in today's episode (with their timestamps). Get your questions answered by Cal! Here’s the link: bit.ly/3U3sTvo Video from today’s episode: youtube.com/calnewportmedia Deep Dive: The Ideas from Marcus Aurelius’s, “Meditations” [2:30] - Can I realistically make an impact as an English teacher? [35:28] - Can a seasoned professional screenwriter switch careers after 23 years? [40:02] - I’m an accomplished professional but lack a competitive drive to do more. Is there a way to build this? [45:34] - How can a CEO lower his anxiety with elements of work that aren’t strengths? [54:37] - How can I bounce back from a deflating work setback? [1:02:52] The 5 Books Cal Read in September 2023 [1:11:07] Thanks to our Sponsors: grammarly.com/podcast policygenius.com blinkist.com/deep expressvpn.com/deep Thanks to Jesse Miller for production, Jay Kerstens for the intro music, and Mark Miles for mastering. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.
Transcript
Discussion (0)
I'm Cal Newport, and this is Deep Questions, the show about living and working deeply in a distracted world.
So I'm here in my Deep Work HQ, joined as always by my producer, Jesse.
Jesse, you know how I know fall is coming?
The leaves?
No, I am podcasting wearing long pants for the first time in many months.
Oh, yeah.
Little known fact.
People only see the top half of me in this studio.
but throughout the spring and summer months, all shorts, all about the athletic shorts.
You got to stay cool.
That's the, that's the key to the podcasting game.
I remember learning this not about podcasting, but about broadcasting in general.
The idea that people generate a lot of heat being on camera, I learned this when I was in high school.
I was a big fan of David Letterman, the CBS version of his show.
And so me and my friends, we finally got tickets to go into Manhattan to the Ed Sullivan Theater to see David Letterman.
And the thing about going to see that show is that it's an ice box in that studio.
And I completely understand it because you're on stage.
You have the camera right on you.
You have to keep it cool because you're going to generate a lot of heat.
You're in a suit.
You have all these clothes on.
So every time I'm in a professional TV studio, I always appreciate it's often really cold.
But that's a nice thing about a podcast studio.
We wear shorts.
No one knows.
Yeah.
A little bit of insider baseball right there.
We should put the games aside, though.
because we have a good show I want to talk to you about today.
First, just keep in mind if you want to watch some of the things you're hearing,
go to the deeplife.com slash listen and find episode 268.
The video links will be below.
So what are we going to do today?
We're going to talk about an ancient philosophy that has become all the rage in recent years.
Then we have some great questions from listeners that are all about trying to find meaning one way or the other in their life.
So we're going to get pretty philosophical and deep in our Q&A.
Then we'll end things up with a review, as I like to do at the beginning of each new month of the books I read in the month previously.
It was a big show.
So let's get started with our deep dive.
Here's what I want to talk about today.
I recently read through Marcus Aurelius's Meditations.
I want to go through the ideas from this classic Stoic treatise.
and point out those that I think are most relevant to our goal here of trying to figure out
the modern concern of building a deep life in a distracted world.
So why stoicism?
Well, let me tell you this.
My own relationship with this philosophy is that it's something I've always had at the
border of my radar, mainly because I've been friends with Ryan Holiday for a long time.
So I knew him throughout all of his career and all of his very successful efforts.
to popularized stoicism, so I knew about it, but I never really dived deeply into it, because
if I wanted to categorize the philosophical foundations for the deep life ideas that we talk about
here, they tend to come much more out of the sort of ancient Hebrew Bible tradition that
then gave rise to great world religions like Judaism, Christianity, and Islam, and then later
acted as the foundation for secular enlightenment philosophy. These are these ideas that emerged
an oral tradition in the late Bronze Age about humans having infinite value that human beings themselves were built in the image of the divine, and therefore every human had value to be preserved.
This was in the front when these philosophies first emerged in the early age of human civilization.
This was an affront to the current order of absolute power by leaders who were ordained by God to be in charge.
This was an affront to this idea of how we should organize the world.
This idea that humans were infinitely valuable, of course, led to everything we now consider as modern justice movements, everything at the core of enlightenment, human rights, as we know it today.
It all came from this idea that humans are infinitely valuable.
And justice is about both respecting the indelible value of the individual and striving towards a more messianic future.
So that's the more of the philosophical underpinnings of the deep life.
And I didn't know a lot about stoicism, but what I had heard about it, the reason why I had always kept it at somewhat of a remove is that stoicism had this cooler aspect about it, where it really focused on this notion of, used a Greek term, the logos, this idea that there was an order of things that suffused everything, all of nature.
And the Stoics would say, just be chill with it.
why get worked up about things?
Just go along with this natural ordained logos, this flow of things.
And, you know, the concern with that is, okay, this natural flow of things could,
depending on who's defining it, also involves strict hierarchies.
It could be the natural flow of things that they're slaves.
It could be the natural flow of things that different people are quite different
in terms of what they can contribute to the world.
So it was at odds with this ancient concept coming out of the Hebrew Bible.
So that's why I'd always sort of like,
well, no, stoicism is different.
But then I read meditations because, you know,
people are really into stoicism.
And what I learned is that critique of stoicism,
though has some validity, is being dismissive.
Because when you read stoicism,
you see the reason why it is resonating with people
is because it has deep psychological truths embedded into it.
It has a nuanced, subtle way of looking at the way
the human mind operates that people today recognize.
Yeah, this is right.
At least the critique of how we think and the way our mind creates problems and how we should deal with them.
These are ideas that also got echoed in Eastern philosophy, also got echoed in modern philosophical movements, in particular second and third wave psychotherapy.
This is what I think people are keen into.
Not the stability of the logos, and it's very important that we follow this logos.
structure, but the deep psychological truths that resonate because they seem like they work.
This is why Stoicism spread so much through the Roman Empire during the period where Rome conquered
the rest of the Mediterranean basin.
When Rome conquered, in particular, Greece and the Near East and were exposed to these ideas
of Stoicism, why did that spread through the Roman Empire?
Why did it spread in Imperial Rome?
Because they said, ah, this works.
It's why in Rome, which is where Marcus Aurelius was, where he was emperor, where he wrote this book,
it's why they stripped down stoicism to get rid of a lot of that stuff I'm uncomfortable with
and focus more on the practical, psychologically realistic way of thinking about how to go through life.
And so I'm re-engaging with stoicism now.
There's some good ideas there.
So what's the plan then?
Well, I took this book.
I read Meditations the other day.
It itself is divided into 12 books.
These are actually probably somewhat arbitrary.
I think the best scholarship now thinks most of the ways we divide meditations in the books now
just happens to be where scrolls ran out and a new scroll started.
So most of the books are not intentional breaks put in place by Aurelius, but whatever.
It's divided in the 12 books.
So what I did is I took one idea from each other.
of the 12 books and meditations that I thought was most relevant to the discussion of the
deep life and the modern fight against distraction that we talk about on the show that are
most relevant to what we talk about here.
So we can find some useful points of connection with stoicism.
So that's what I want to go through and do.
So I'm going to pull these quotes book by book up on the screen for those who are watching
instead of just listening.
Let's start with quote number one from book number one of meditations.
This is from passage number six.
And by the way, I should mention all of these are coming from the Gregory Hayes translation.
This is from, I think, 2003, 2004.
It's done in a modern English vernacular.
So it's a much more approachable translation.
This is a very popular translation.
So just so you know, this is where my exact wording is coming from.
All right, quote number one from book one, it's not to waste time on nonsense,
not to be taken in by conjurers and who-do artist.
I should hold on a second.
Oh, okay.
I'm going to clarify this.
So see at the bottom, this is a, this is a little bit difficult.
Book one is different than the other books.
What's happening in book one, so excuse my, my pause here, but this is a complicated
book.
What's happening in book one, which is different than the other 11 books of meditations,
is that book one, which is titled Lessons and Depths, in book one,
are really, says going through a list of people he knows in his life and listing
out what influenced me from this person? What traits of this person do I want to remember as being
important? So item number six that I'm quoting here are things he learned from Diognetus,
who was, I believe, a tutor of Aurelius when he was in his teenage years as a Greek tutor
who probably was tutoring Aurelius in more of a Spartan approach to physical endurance.
So here is the points that he said, this is what I,
learned from this particular tutor from early of my life.
Not to waste time on nonsense.
Not to be taken in by conjurers and hoodoo artist with their talk about incantations and
exorcism and all the rest of it.
Not to be obsessed with quail fighting or other crazes like that.
So I think the specific quote is useful because there's an idea in here.
He's basically saying, work on what matters.
Don't get sidetracked by shortcuts or secret systems that guarantee you success.
If you just watch this YouTube video on the 12 ways to become an influencer,
you're going to be making $100,000 a month.
Don't get caught in by that.
Don't get completely obsessed with lightweight distractions that do not help you fulfill your purpose
or be useful to the world.
Do what matters.
I also want to point out that the overarching idea of book one of going through people in your life
and listing out what traits they have that resonates with you,
that's another brilliant idea that dovetails nicely with our notion of lifestyle-centric career planning.
Clearly identify what resonates with you so you can use that as a guide to cultivating what you do going forward.
All right, let's go to book two.
This is line seven or passage seven from book two.
Do external things distract you?
Then make time for yourself to learn something worthwhile.
Stop letting yourself be pulled in all.
directions. This obviously resonates with me because it's the core idea of my digital
minimalism philosophy. When I was working on that book and I was interviewing people
about their discomfort with their relationship with their phones, what they focused on
was not the content they were seeing on their phone. Their issue was not my phone is
showing me bad things. If we could just change what's on the phone so it's good things,
I would be happy.
Instead, by far the most common explanation for why their phones were upsetting them
was that it was keeping them away from even better activity.
It was fine what they were seeing on Instagram or Twitter.
The point was it was keeping them away from their kids.
It was keeping them away from learning something useful.
It was keeping them away from being a useful member of society, being a leader in their community.
I think Ourelius gets to this here.
Make time for yourself to learn something worthwhile.
Stop letting yourself be pulled.
in all directions.
All right, let's move on here to book three.
The quote I want to give here is from passage nine.
Your ability to control your thoughts, treat with respect.
It's all that protects your mind from false perceptions, false to your nature,
and that of all rational beings.
Now, this is an idea that I've been thinking about as part of a background project
I've been working on for a manifesto that I've been titling in defense of thinking.
And one of the core ideas of this proto-manifesto I've been contemplating is that in 21st century society, we don't give enough respect to thoughts.
We don't give enough respect to how we think, what we think about, how we label things that happen to us or sensations that we're feeling.
Our mind constructs our vision of reality.
This was a key concept that in my book, Deep Work, I borrow.
from Winifred Gallagher and her great treatise wrapped RAPT.
Our mind makes our world, our mind defines our experience of our world, our mind defines
the impact we have on the world.
We don't care about it enough.
So what do we do instead when our, we don't like what's happening or we don't like what's
feeling, what we're feeling when we get, we feel anxious or ashamed or guilty, what do we
do instead is we try to drown it out with pints or bites. What I mean by that is either,
you know, substances to drown out the, the negative sensations or digital distraction,
pints or bites. Or really is to say, no, no, treating yourself and your thoughts with respect,
be very careful how you label things, how you think about your world, what's going on around you,
what matters, can make a difference. That is the way, that is the way to actually live true
to your nature.
All right.
From book four, I pulled out passage number three.
People try to get away from it all, to the country, to the beach, to the mountains.
You always wish you could too, which is idiotic.
You can get away from it any time you like by going within.
Nowhere you can go is more peaceful, more free of interruptions than your own soul.
So Marcus is talking about a fairy tale that I think a lot of people like to tell themselves today.
which is the solution to their anxiety and their overload and their boredom, their enwee, their shame with where they are in life and where they want to be,
is some sort of big radical locational change, that just by radically changing the physical details of your situation can radically change your perception of yourself, your perception of the world.
Now, there's issues with this.
Orelius is pointing out one particular issue in this quote, which is you need to be able to find peace
wherever you are.
You do not need a grand change to find peace.
This is something you need to cultivate the ability to do
regardless of your circumstances.
If you are really anxious from all your work
or you feel bad about your impact on the world,
going to the beach is not going to change that.
Your inbox will bother you in the Bahamas
as easily as it can in the suburbs.
Your discontent with your life does not disappear
when you make it to the top of the mountain.
It sits there just as it was when you were in your office in the city.
So Aurelius is saying these fairy tales are going to keep you from solving the problem because you'll just say, no, one day when I make the grand change, that's when things will get better.
And either that day never comes.
So you're constantly suffering from these things.
Or, and I think this is worse, the change happens and it doesn't heal you.
And then people get quite despondent.
We've seen that all the time.
There's another problem with this fairy tale that I'm going to add, which is the logistical details of what's overloading you are completely location independent.
So let's just get practical and put aside the anxiety or the discontent with your place in life.
The flip side of a world in which you can be more remote in your knowledge work is that remoteness does less to save you from what's making you unhappy about your knowledge work, right?
This is a double-edged sword.
Yes, it is possible now for you to move to a cabin in Vermont because you can work on an internet connection,
but it also makes it possible for everything that was making you distracted in your current location to follow you to Vermont.
So again, these are problems, the practical problems you have to fix as well.
So Aurelius is just saying figure out how to find peace with your mind where you are.
Don't think that'll be solved by a radical change.
And I'm saying figure out how to solve the logistical sources of your stress and anxiety in your current situation.
don't think simply changing where you live is going to fix that either.
So he's really ahead of his time there.
All right, book number five, I want to quote passage number three.
By the way, you'll see the terminology of this.
Look, this passage starts not to feel exasperated or defeated.
That's a weird start, right?
There's no subject in this sentence.
And that's because you have to keep in mind.
Meditations was not written as a philosophical track to be read by other people.
it was written almost certainly as reminders to Eurelius himself.
He's writing down notes the self that he is going to review again and again to help try to keep him on the deep track.
That's why you're going to see these unusual sentence constructions.
They make perfect sense when you think of this as something you wrote down for you to read,
as opposed to a philosophical tract that you wanted other people to read.
So keep that in mind.
All right, let's go to this quote.
So it's a reminder to himself, not to feel exasperated or defeated or despondent because your days aren't packed with wise and moral actions, but to get back up when you fail, to celebrate behaving like a human, however imperfectly and fully embraced a pursuit that you've embarked on.
So I really says pointing out of truth here, doing good stuff.
Living in a way that lets you hit that pillow proud each night is hard work and you're not always going to succeed.
What's important is getting back up and keep returning to the path that you know is just and right.
There's a deep philosophical and psychological truth in that.
I mean, coincidentally, we're recording this episode on the day after Yom Kippur,
which, of course, is in large part all about repentance or Teshuvah, if we're going to use the Hebrew word.
it's a huge part of this most ancient of all the wisdom traditions, and then it carries through other wisdom traditions as well, have a really nuanced take on how to seek repentance as you fall away from the right path.
They saw it like Aurelius does here as fundamental to the human nature.
If you want to get some exposure to how nuanced we were in these early days of deep human thought and think about repentance, I would recommend read the book of Jonah.
surprisingly nuanced take on repentance.
All right, let's move on.
Book 6.
This is passage number 33 from book 6.
It's normal to feel pain in your hands and feet.
If you're using your feet as feet in your hands as hands.
And for a human being to feel stress is normal if he's living a normal human life.
And if it's normal, how can it be bad?
So I really is the saying if you're doing what is demanded of you as a human.
So again, for the Stoics, I would be living out, you know, what logo says is.
necessary and right for you and your position in life, you're going to feel stress.
There will be stressful things because you'll be doing some things that are hard.
You'll be doing some things that get you anxious or you're worried about how it's going to turn out.
Otherwise, you're not trying anything big.
And he's saying that's okay.
That's normal.
So why label it is bad?
It's something that comes.
It's part of what you do.
It's part of your human nature.
Now, of course, on the other hand, you have to caveat this by saying persistent stress can then have the opposite effect.
If you're overloaded or you've designed your life in such a way that stress is constant,
if you're like the Adam Sandler character in uncut gyms where your entire life is
you're one step away from having your arm broken and Adina Mansell yelling at you,
then that's going to hold you back from your true human nature.
So you don't want to label stress when it comes as bad, but also you don't want to be stressed
all the time.
It's a hard balancing act.
But writing all these years ago, I really is recognized it's important.
And I'm just imagine he was an emperor of Rome.
And there's a lot of stress that came with that job as there's difficult things he had to deal with.
And he's reminding himself, this is me filling my human nature, my role as emperor trying to take care of this country.
That's part of what I'm supposed to do.
So why is this bad?
It's just a feeling.
All right, move on the book.
Seven.
I just watched a documentary about Adina Menzel.
Okay.
Yeah.
It's a hard, talented, hardworking person.
I don't know why I watched that documentary.
But talk about slow productivity.
I mean, man, she
a long, long career.
Mm-hmm.
Yeah.
Not mentioned specifically in meditations, though.
So let's move on.
Book number seven,
I'm going to quote passage number 56.
Think of yourself as dead.
You have lived your life.
Now what's left and live it properly.
This is classic stoicism.
That's why I included it here.
This is one of these classic stoic exercises.
You imagine your death
so that you have more.
appreciation for the life you have left and will resolve not to waste it.
Again, an ancient idea, not to keep harping on the fact that this is the day after Yom Kippur,
but as all of the Jewish individuals in my audience know, this is sort of the whole point of
Yom Kippur is you're essentially simulating death through fasting and wearing the white that
traditionally was part of the shroud you would wear in death.
you're simulating death as a way to try to motivate repentance and a recommitment to live the life you have left.
So this is an ancient idea, a classic Stoic idea, but far from the only people to think of this.
All right, we're making good progress here.
Book number eight, this is from passage 19.
Everything is here for a purpose, from horses to vine shoots.
What's surprising about that?
Even the sun will tell you, I have a purpose.
and the other gods as well.
And why were you born?
For pleasure?
See if that answer will stand up to questioning.
Right?
So I'm going to really say,
what is your purpose here?
What is your purpose during the time you have on Earth?
You need to actually confront that question.
Because when you do, you're going to see the answer is almost certainly not
to be on email all day at work and on my phone and video games all night when work is done.
That can't possibly be your purpose.
And so it's a push to sit back and say, why am I here?
What good can I do?
And here I think this is where the Logos concept is useful because it's saying this could be different for different people.
But where you're going to find strife and unhappiness and discord is when you get separated from this purpose and try to distract yourself like perhaps the Epicureans might have done, try to distract yourself from what's necessary.
to maybe just focus on what's fine or what's pleasure
or to fall into despair and despondency
about everything you don't like.
Find your purpose.
Pursue it.
We're making good progress here.
Book number nine, we'll read passage 13.
Today I escape from anxiety.
Or no, I discarded it
because it was within me
in my own perceptions,
not outside.
So in this particular translation,
Aurelius predated acceptance commitment therapy,
otherwise not a third wave psychotherapy by 2,000 years.
I mean, this is actually at the core of modern evidence-based treatment for anxiety,
separating the physical sensations of anxiety, which let's think about it.
What is it?
It's a feeling of pressure constriction right here, somewhat of a shallowness of breath.
That's it.
Isolating that from the mind's interpretation of anxiety.
This is untenable.
We have to make this go away.
we have to remove the stimulus for this feeling.
Arrelius was on this 2,000 years ago.
Anxiety is a perception.
It's the way you label some otherwise unremarkable physical sensations.
Anxiety is something I definitely have experience with.
That's a story for another time.
But Arrelius is right.
He's on to something there.
All right.
Here's my quote from book 10.
Here's a long one.
This is passage 35.
But it's an interesting analogy he makes here.
A healthy pair of eyes should see every.
that can be seen and not say no too bright, which is a symptom of ophthalmalia.
A healthy sense of hearing or smell should be prepared for any sound or scent.
A healthy stomach should have the same reaction to all foods as a mill to what it grinds.
So too a healthy mind should be prepared for anything.
The one that keeps saying, are my children all right?
Or everyone must approve of me is like eyes that can only stand pale colors or teeth that can only handle mush.
Once again, this is a really a saying.
the human condition when you are pursuing your purpose here on Earth has ups and downs.
Bad things, bad events will happen.
There'll be bad sensations and perceptions that you'll have.
That's part of what you're supposed to go through.
That's part of life.
So to be able to not handle that, to say I have to focus on avoiding bad events obsessively
or when bad perceptions happen, fixate on them, is to alienate yourself from your fundamental human nature.
It's like an eye that can't see things unless it's just the perfect conditions.
You don't need the perfect conditions to live deeply.
You don't need the perfect conditions to thrive.
Trust me, in the ancient world, they had all sorts of terrible conditions.
Aurelius lost most of his children out of a young age, went through all sorts of turmoil in his term as emperor.
A really bad plague came through.
He had a share of hardships.
So the idea that you need just the perfect conditions to function as a human, he is saying nonsense.
Whoever has perfect conditions.
just doesn't happen. Two more books left. Let's do book number 11. Passage 7. It stares you in the face. No role is so, no role is so well-suited the philosophy as the one you happen to be in right now. This comes back in some sense to my notion of the deep life stack. You have to actually have a vision for your life, what you value, and how systematically you're going to cultivate your life around it. This is what he means by philosophy, an intentional approach to your life.
He is saying philosophy is not abstract.
He's rejecting a lot of the concerns of the Greek Stoics that predated him,
who were trying to infuse a more abstract philosophy through many different aspects of the world.
Natural sciences, thinking about logic, also thinking about how to live.
And he said, how to live is what I mean my philosophy.
You have to think about it.
You have to have a philosophy or you're going to flail.
A smaller example of this in my own work is my book, Digital Minimalism,
where I said when it comes to technology in particular,
your relationship to modern technology,
there's two groups of people.
Those who have a value-based philosophy
about how they engage with technology
and those who don't.
The philosophy group can have a healthy relationship and thrive.
The other group is going to have a hard time with philosophy,
do a lot of crash digital detox and make their screen, you know, gray scale,
and ultimately be stressed out and not succeed.
You need philosophy.
All right.
final quote from meditations from book 12 passage number 33 how the mind conducts itself it all
depends on that all the rest is within its power or beyond its control corpses and smoke again
this wraps up a lot of arellius's psychological realism what matters is how your mind perceives
the world how your mind reacts to events and perceptions that's what matters not the events
themselves not the perceptions themselves so a sophisticated psychological
awareness that are really is is pushing.
You need to treat your mind and how it thinks with respect and care and intention.
All right.
Well, to summarize, clearly the ideas from Stoicism are hitting a chord.
You know, my friend Ryan Holiday is a very successful, very impactful writer.
This book, I was telling Jesse about this right before we recorded, this translation of
meditations, which is, it's a great translation, but it's 10 years old.
When I bought this book the other day, it was number 61 on Amazon.
So these ideas are thousands of years old.
This particular translation is over 10 years old.
It's from like 2003, 2004, I believe.
And it's one of the best-selling books in the world right now.
So clearly there's ideas that are powerful.
So again, there are some general reservations if we consider stoicism as a philosophy writ large.
If we consider stoicism, if you say this is going to be my sole foundation,
on which I'm going to build my life,
there are maybe some danger in there
and there's maybe some things missing,
right?
Because it doesn't get to that,
I would say,
spiritual realism
of the more Judeic Christian tradition
of the human
of having infinite divineness.
But there's huge psychological realism
that's 2,000 years ahead of its time,
especially the Roman version of Stoicism
that really focuses on pragmatic approaches to life.
So I am not surprised this is doing well.
There's clearly some good
connections to the deep life concept that we talk about here on the show. So I enjoyed having a chance
to read this. She'd pick it up. All right, Jesse, there we go. Stoicism. Yeah, good summary.
I like the quotes. Summised. Yeah, I mean, they're very, I was reading another translation of
meditations. A lot of the translations, because Greek is a Latin, can be a very formal language.
And a lot of the translations, there's a lot of these and thys. I think that's why this
translation is doing well, it's fantastically
vernacular. It feels
modern, and that's really Greg Hayes,
I think his skill.
All right, so in honor of
that deep dive, the questions we're going to tackle
today from you, my listeners,
are more philosophical in nature about
finding meaning in life. So that should be fun.
Before we get there, though, let me take a brief
break to mention one of the sponsors
that makes this show possible, a
longtime sponsor of this show,
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More recently, however, Gramerly has really leveraged recent breakthroughs in generative AI to really improve in a focused way the different manners in which,
their tool can help with your writing.
Let me be clear about this.
One of the things you can now ask is if you're feeling stuck while writing, you can ask
it for ideas or outlines.
You can say, for example, give me 10 possible taglines for a video thumbnail.
If you want to polish it, you can actually have it now help you rewrite phrases you wrote.
So you write what you want to write, but say, hey, can you say this more concisely?
Can you say this more professionally?
You get through your emails quicker.
You can actually say, can you summarize this email that's currently on the screen?
And it will give you a quick summary of it.
Right.
So this is in addition to the other stuff, Grammarly has always done well.
Of course, when you know if there's grammar mistakes, but also helping you with tone and style.
You know, this has been more recent.
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Can you make the tone of this writing a little more professional?
Is this a little bit too aggressive?
But now they've added these generative AI augmented features that really,
really takes it to the next level. I talk a lot about AI on the show. And one of the things I
often say is that this is how we should be thinking about Gen AI's impact is on these very focused
specific tasks where it can come in, take something you already do and help you do it better.
So you'll be amazed at what you can do with Gramerly now. So go to Gramerly.com slash podcast
to download the tool for free today. That's G-R-A-M-M-A-R-L-Y-E-R-L-Y.
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As long as we're talking about technology,
let's talk about our friends at ExpressVPN.
As I've said before,
you need a VPN.
Why?
Because people can monitor what websites and services you use.
If you're on a wireless access point at a coffee shop,
anyone nearby with an antenna can see what websites or services you're talking to.
If you're at home,
your internet service provider sees exactly what websites or services you're
talking to. So even if you have an encrypted connection, that just encrypts what you're saying
to those sites. It doesn't encrypt who you're talking to. And so people can get that information,
and they do. It's been revealed, for example, that many internet service providers sell information
about what sites and services you use to data merchants so they can target you better with
advertising. This is why you need a VPN. So what happens with a VPN? Instead of connecting directly
to a website or server, you instead connect to a VPN server.
And then you tell that VPN server with an encrypted message,
this is who I really want to talk to.
And that server talks to the site or service on your behalf,
encrypts the answer, and then sends it back to you.
So all the guy with the antenna in the coffee shop
or your internet service provider sees is that you're talking to a VPN.
And they learn nothing about what you're actually using.
So if you're going to use a VPN, I suggest using the one
that I personally recommend,
which is ExpressVPN.
They've got servers all around the world.
They've got the bandwidth.
The tool is so easy to use.
You turn it on with a click
and then use your apps or web browsers like you would.
Normal.
It just happens all transparently in the background.
So check out ExpressVPN.
So you can secure your online data today
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That's EXPR-E-S-V-P-N.com slash deep.
Don't forget that slash deep,
because that will get you an extra three months free expressvPN.com slash deep.
All right.
Speaking of deep, Jesse, let's do some deep questions from our listeners.
We've got some good ones today.
Yeah, we do.
A real first philosophical, you know, thread, which I love.
Let's get deep here.
All right.
Who do we have first?
We're up first with John.
I'm a 31-year-old English teacher.
I'm very good at what I do and I'm well respected in the community.
That said, I have a nagging feeling that I have the potential
for more impact.
I fear that as long as I stay in schools,
I don't have the same level of autonomy
to build my perfect life for my family,
as well as fulfill all the aspirations I have for myself.
What should I do?
So I'm thinking, in honor of stoicism,
I'm going to answer every question by saying,
imagine your own death.
And then I want you to play a sort of, you know,
like, funeral durs.
Yeah.
And then let's have the,
the graphics people turn my face into a skull back to my face 10 seconds eye contact with camera
silence next question that's that's my idea of a stoic pod this is why i don't podcast about
stoicism because i would i would love face turning the skull graphics i just would want to do that
all the time you should use express VPN because tomorrow you could die and then a skull comes
across my face and come back.
I mean, I don't know.
Ryan does well with his stuff, so maybe we'd be more successful.
All right.
Sorry, John.
You have a serious question.
You have a serious question.
I have not concerns, but I want to give you a, let's think of this as a safe path forward
because you're feeling, you say here, nagging feeling you have the potential for
more impact.
You're also talking about building the perfect life for your family.
What I don't want you to do here is just make a radical change.
with the hope that the radical change itself is going to heal you.
We saw this in Marcus Aurelius, right?
He said, oh, everyone dreams about going to the beach or the mountains and you'll be fine.
And he said, this is quote unquote idiotic.
I don't know what the Latin term for idiotic is.
I'm sure it's very fancy.
But he was cutting to the trace.
That's not going to solve the problem by itself.
So what I want you to do instead here is really embrace lifestyle-centric career planning.
So I want you to be more specific about this vision of your perfect life for your
family, be more specific about your aspirations and what it looks like to be fulfilling your
aspirations.
We want this specificity because then you can get more specific in your responses to this
otherwise vague but insistent urge that you feel.
And there's a lot of ways this might go.
Like you might realize actually there's a way to work with your existing job as a teacher
and be very high impact and get great fulfillment out of that.
Maybe sand off some of the rough edges of it.
You know, okay, I need to find a way to do it.
this where I can have more freedom in the summer and that's going to require a little bit more
financial whatever.
And I don't want to teach this class move here and not do the department chair position.
Like there's some finagling maybe.
And again, I'm just doing thought of it.
Maybe some finagling to make it work, but then also lean into what you value out of it, the
sort of Robin Williams, that poet society core to it.
And you might find that really most of the things you want for this perfect life for your
family are sort of orthogonal to your job and about what you're doing in the rest of your
life and how you're structuring the rest of your life and what you're.
you pursue. Or you might find, oh, I have this clear aspiration. And being an English teacher
doesn't get me there. But this would, this other option that makes sense. And here's how I'd
get to that other option. And this combined with moving here clearly gets me closer to my vision.
So maybe there's going to be a change there. But specificity is what I want to underline here.
Because otherwise, you're going to quit and, you know, have some idea about doing YouTube videos
on Shakespeare and you're like,
Mr. Beast makes a million dollars
video.
Like I can,
I just have to do one percent of that.
And I'd be fine.
And,
you know,
you get these ideas and,
and then you,
you want them to be true.
And then you move to the,
you know,
I don't know,
you're an English teacher.
I imagine you living in England,
which makes no sense.
I was about to say,
you moved the Cornwall to the coast,
because I was trying to be very British.
But English teacher,
of course,
it's crazy.
That's just,
you could,
you could live anywhere.
So whatever.
But you know what I'm saying.
You're going to end up moving somewhere dramatic you can't afford and thinking your YouTube videos are going to make money and then your wife gets really mad at you and then everything's worse.
So lifestyle and your career planning.
Specificity in vision leads to specificity in action, which leads to a much higher probability of good return.
All right.
Let's keep rolling.
Who do we have next?
All right.
Next question is from Mike.
I'm a 51-year-old professional screenwriter in Hollywood, and I've been doing that for the last 23 years.
I write mostly movies and some TV.
I've had a lot of success in the business, along with a few disappointments, but I've spent the last five or six years growing increasingly frustrated with my job.
In short, I would love nothing more than to find a new career.
However, I'm married with two high school children, and I want to find something that's stable and sustainable for possibly the next 10 to 15 years.
and I want to live in the same area that I'm living now, which is in Southern California.
I'm creative.
I have excellent written and verbal skills.
I'm great with pressure and deadlines, but I have no experience in any other business.
I feel like a recent liberal arts graduate entering the job market for the first time with no tangible skills, no business knowledge, no understanding of any other industry.
Can I switch jobs?
And if so, how?
Well, Mike, my number one piece of advice, imagine your own death.
Skull graphic.
Every time, I'm going to do it every time.
You're not going to stop me.
Jesse, I actually looked up.
We have more information on Mike than we set on air,
and I won't give any more identified information,
but I did look him up,
and I have seen three movies that he has written.
That's pretty cool.
Yeah, he's a successful screenbook.
Yeah, he's right in the middle of the strike,
which is about to end.
Yeah, hopefully, yeah.
Right now he's not doing a lot of writing at all
because of the WGA strike that's going on.
So there's a couple, there's like a dose of realism, I suppose I want to throw in here.
It's hard to get people to give you money.
And you found a way to get people to give you money that requires a huge amount of hard-won skill,
which is give me money for writing screenplays.
99.9% of people who do this don't get anywhere near being able to make a living off of it.
So you have to borrow a term for my book so good they can't ignore you.
this core foundation of career capital that was incredibly hard won.
And it does give you some big advantages, right?
Creative work done entirely autonomously that is so winner take all that the financial rewards of it can actually help you sustain your livelihood.
Most people have to be essentially trading their hours almost directly for work.
Screenwriters don't.
So we want to be very wary about discarding that career capital completely because, again, it's very difficult.
to say, look, I can write well.
I want to make a good living.
People are reluctant to give other people money.
So I want to be cautious about it.
So I think career capital is our first thing we want to keep in mind here.
When considering other careers, you want to maximize as much of the existing career capital you can in these ideas.
So there's a difference between going to some sort of, I don't know, media startup that direct,
will value your ability to write movie and film screenplays at a high level.
Even if you're not doing that particular activity, the fact that you can recognize that, you can recognize good film and movie screenplays.
You know, moving to a company that would respect and is looking for that talent, you're going to have a lot more reward options and autonomy than if, say, you said, I'm just going to become a full-time nonfiction writer, right?
Or you're going into a different career.
Or I just want to go work in advertising.
they look for good communication skills.
You don't have any particular skills in those fields yet.
So unless you get really lucky, you can't necessarily expect someone
is going to give you a lot of money and or autonomy.
So career capital is important here.
The other thing that's important here,
another concept for my book, So Good, They Can't Ignore You.
Use money as a neutral indicator of value.
In other words, what that means is when you're considering another option,
you need to start almost certainly that other option on the side
in a way where you can actually put it out there in a marketplace and see how much money people
will give it for you, will give you for it.
Will they give you money for your startup concept?
Will they hire you to do the service that you're offering?
Will they buy the product or view the media that you're producing?
You need to use that people giving you hard one money as a neutral indicator about the value
of what it is that you want to build your next career on top of.
You can't just ask people, is this a good idea?
They'll tell you yes.
You can't just ask yourself, do I think this is a good idea?
Because your mind will tell yourself the story it wants to be true.
You need to see, do people actually give me money for this?
And there's a big idea from So Go, they can't ignore you.
And then once the money from this becomes substantial that you can then confidently extrapolate it to where you need it to be,
if it only then you say, okay, now I'm leaving the main thing I'm doing.
Again, the advantage of being a screenwriter is that you have a lot of autonomy to do this.
You're not checking into an office where there's a lumber,
style boss looking over your shoulder where it's very difficult to work on something on the side.
You can experiment with this quite easily in your particular role.
So I want to encourage you, yes, if you really are ready for a change and this is becoming
disparity and there's a bit of a drag going on on your soul here, think about making a change,
but keep career capital in mind.
You probably want to use money as a neutral indicator value.
This might slow down the change.
It might slow down the radical dramaticness of the change when it happens, but it's going to be
insurance against career vision disaster.
Okay, let's keep rolling.
Who do we got next?
All right.
Next question is from Margo.
How do I cultivate personal ambition or a competitive drive?
I am reasonably talented.
I went to a top graduate program, and I'm a recently tenured professor at an R1
university in a STEM field.
I've recently been interested in trying to get a job at a different university, but I feel
like right now I'm not an attractive candidate for a senior hire.
I'm on sabbatical next year and think it would be great to try my time to build back up my profile,
but I don't feel any inclination anymore to push myself,
and I feel like I sort of lack ambition or motivation.
Is there a research on how to build ambition or a competitive drive,
or do you have any advice on how I can pursue this goal?
First of all, and I'm resisting saying think about death, so be glad about that.
I just want to point out, this is such a reality of me and Margo's sort of very narrow field being, you know, tenure track professors at R1 universities.
Look up front, she says, I think I'm reasonably talented.
You know how hard it is to be a tenured professor at an R1 university?
That means she or he, I don't know, this is a French spelling here.
So I'm just going to say, I think it's a she.
It's a she.
Okay, I'm going to say she.
You have to be the top 0.01% of anyone studying that topic in the world to be a 10-year professor.
But it's the way the system works.
As soon as you're tenured, you look around and like, well, that tenure professor is better.
And that one got full professor quicker.
There's nowhere you can go.
There's nowhere you can go in academia where you don't think, man, I wish I was good as that person over there.
I mean, Richard Feynman standing on stage of the 1960s with.
his Nobel Prize.
I can guarantee you was thinking something at some point around that event along the lines
of, yeah, I'm no Einstein.
And I can guarantee you that Einstein is saying at some point, well, you know, I revised
Newtonian mechanics, but I'm no Newton.
You know, so the bars are impossible.
There is no, there's no top to those bars.
So I just wanted to point that out, Margot, your top point, 0.001% of anyone who's
ever thought about that topic and is in the job market right now.
So you're more than reasonably talented.
All right. So you lack a competitive drive right now.
I think what's going on is two things.
One, your mind is not particularly jazzed by your vision.
So we got more detail that we didn't read on air.
But one of the elements from your extended question is that you're leaving more because
there's stuff you don't like about your current university than it is that there's a specific
positive vision that you're pursuing.
it's hard to get really geared up for very difficult work when really it's just about,
I don't like what's happening here.
Maybe it'll be better somewhere else.
Also, and again, I'm drawing from the longer version of your question, you're tired.
You had a baby recently.
So you're tired.
And you have other things.
Your mind very correctly is saying, this is really important because it is, because you have a baby.
And human babies are born in a way that makes them much more helpless.
and other mammals at that same age
and every instinct in your body
is saying this should be a priority right now.
This is why you should be, I would say,
be happier, a tenured professor.
Great.
Downshift.
Let's focus on this a little bit more for now.
The gear shifter goes up as easily as down later
when the time comes.
I think those two things are going on.
So yeah, you're not chess.
This is not, you're not,
it's not a problem that you're lacking
a quote unquote competitive drive
right now for those
vision of I want to move from this university to that.
I think it's a plan that looks good on paper, but your mind is not really excited about it.
And this is a really hard thing.
It's like if you said, if you're an alpinist, alpinist, you know, like, I want to climb K2,
but your heart's not really in it because you have a lot of other things going on.
You're not going to get motivation to go do that because it's incredibly difficult and
is deadly and dangerous and it has to be, you have to be all in on it.
And until you're ready to do that, you're not going to want to try it.
So what should you do instead?
I don't know.
I would recommend.
First of all, keeping in mind, life is long.
I often think this days are short, life is long.
So, you know, I've had three different kids while being a professor on both sides of tenure.
And when you're on the other side of them being young, you see this as a very short period.
But when you're in the middle of it, you see it as, oh, my God, I guess I'm no longer in academics.
So just keep that in mind, life is long, days are short.
I would also say keep in mind, maybe it's a good time to go back to the deep life stack and work it a bit.
because most of the Deep Life stack is non-professional.
And this might be where you're going to get some gas back in the tank
as thinking about the other things that are important in your life,
going back and re-engaging with discipline
and getting the control and all the different things,
clarifying your values, having a code and rituals that support it,
becoming a leader in the communities that matter
from your family to your town, to the wider university,
your global communities.
These things that make humans human,
get to the top level of the stack
where you plan for the remarkable
and maybe change an aspect of your life that's not professional into something more remarkable.
You change where you live or your house or you start some sort of program that's like really exciting and off the wall.
Work to stack for a bit.
Refine some mojo because, look, you've been focused on this since grad school.
You got the tenure.
Your mind's like, we've done this.
I really don't want to gear up again for a new academic push.
And I'm tired to get the other parts of your life in order and then step back and do some lifestyle such a career planning.
And there, when you're feeling like you've got your arm around your life, you have that you're in the driver's seat of intention again.
You trust your efficacy, that your self-discipline is there.
You can say, okay, what do we want to do with this professional thing?
Do I want to reconfigure my situation here at my university?
Do I want to move?
Okay, now, how am I going to move?
This, I'm going to focus on this to go over here.
And you start to get creative.
You start to see avenues.
But I think what's happening now, again, is that you're just on paper.
I should go somewhere else.
It's just like myopic academic focus.
we all get in this career.
Let me go to a better school.
It's going to be better.
Oh, my God, I got to get these grants and these publications.
And, oh, my God, it's going to be so hard.
And I've been up all night with the baby.
That's just not going to fly.
The dog's not going to hunt there.
All right.
So be chill with the idea that you're downshifted right now.
Work to full deep life stack.
And then we'll return to this question with wind behind us pushing to proverbial sales,
saying, now what do I really want to do with this professional aspect of my life?
You'll be ready to answer that question then.
Yeah, I agree with her.
She could even introduce some of the competitiveness into our non-professional life, for instance, like, for me, it would be like golf or tennis match or something like that.
Yeah, like something athletic or a hobby.
Yeah.
Yeah.
Get your spirit in order.
You know, there's a good book about this.
I'll recommend.
And I don't know exactly.
I'm going to get the name wrong.
I think it's an MIT philosophy professor.
There's like two of those, right?
because everyone at MIT is a STEM person, except where they have like one philosopher and, you know, one humanities professor.
But I believe his name is Kieran Sieta, C-E-I-T-Y-A. Jesse will check this out.
But the book he wrote is called Midlife.
I've talked about it on the program before.
And in it, Margot, he talks about reaching tenure at MIT and exactly this drop in competitive drive, a sort of midlife crisis, so to speak.
it comes early for academics because 10 year typically happens in your 30s.
He was in your exact same situation and he gets into his subsequent, he embraced Aristotle in particular and the Nica Machimachean ethics and he pulled from philosophy to sort of engage with this question of refinding meaning in midlife.
And again, I know you might be at an age where you say I'm not quite midlife yet, but academic years are like dog years.
So you can be 33 and it's like the normal person equivalent of being.
47. So check that book out. Also check out perhaps the second mountain by David Brooks, which is again all about his similar thing.
Second half of life. So the first mountain is your professional, your initial professional ambition to become a tenured professor, to become a calm in this New York Times, what you do with the second half of your life. What's the second mountain that you pursue? That book, I think you're going to find, you'll find a lot of value in that as well. So it's an exciting time you're actually at my time.
This is not a problem that your mind is no longer completely geared up for, let's write 17 papers this year.
Actually, you're at the precipice of something potentially transformative, and you have tenure.
So you have some flexibility to actually pursue it.
So this would be my Marcus Aurelius advice would be change your analysis of this current moment to be a very positive thing and not a negative thing.
All right.
Let's do another one.
What do we got?
Hi.
Next question is from Raphael.
I'm a lawyer.
and in 2001 I decided I wanted to live a more meaningful life.
I learned a code and use this career capital to launch a bootstrap startup in my field.
I've been pretty successful with consistent revenue growth.
And currently I have a team of 15 people.
The journey was a joy in the beginning, but things have been really stressful for the last five years.
It seems that even though I'm the CEO, I can't find time to deal with the important stuff
and I'm always dwelling on what's urgent.
How can I go about organizing my life differently so that I can deliver?
work that really matters and I stop being so on edge, there must be a way as I'm the CEO.
Well, I'm going to give you, Raphael, I'm going to give you the tactical short-term answer,
and I'm going to give you a bigger sort of philosophical answer to this question as well.
So starting with the more practical answer, there are some things you can do.
You should think about bringing on an accomplished chief of staff.
This is a useful position.
Tim Ferriss actually talked about this in a recent episode of his podcast with Sam Caracos from Level Up.
They talk about what a chief of staff does versus an assistant.
You can probably use this.
A chief of staff can take a lot off your plate.
They can implement, come up with ideas and implement.
They can be the buffer between you and a lot of other types of information flows.
That might be really important for you.
You can take a lesson from George C. Marshall, chief of staff during World War II, ran the military,
for America during World War II.
In my book, A World Without Email,
I talk about a report
of his management style
that was commissioned
after World War II.
This was someone at a service academy,
I believe, wrote this report.
Because here's the cool thing about Marshall.
He was running the U.S.
Armed Forces during the largest
military buildup in the history
of our country, if not the world.
And he would work till five.
It would not work past five.
He had a heart condition.
As doctor said, don't work
past five. He's a disciplined guy. He said, I'll make that happen. And this, this paper that I talk
about in a world without email gets into how did Marshall pull this off. There's a lot of good ideas in there.
Two ideas I'll mention in particular is one, he completely reorganized the war department.
There was too many people that could report directly to him. He's like this is inefficient.
He reworked the org chart. So there was many fewer people who reported directly to him.
Most people directed to someone who was below him. So there's less people who could
directly get his attention.
And then two, he had big demands for how you talk to him.
And it's a big problem that leaders have today where they say communication is communication.
I want to be available.
That means I'm agile.
That means I have my finger on the pulse of the company.
This was like the original idea pitched when email was new, this famous Wired article
about Bill Gates getting email and how he answered every email and it was considered
this revolutionary thing.
It doesn't work.
So Marshall was very careful about how you can.
communicated to them. You had to know, this is my purpose in talking to you before you would get
into Marshall's office. You had to give him a quick briefing. You had to get right to the nub of
this is where a decision needs to be made, that we need your input. Here is all the relevant
information. And if you weren't prepared, he would kick you right out. So he made other people do
more work before they communicated with him. This is not asymmetry. This is about maximizing his
potential impact at the head of the organization. It is not maximized if he has to sit there while
you're trying to figure out while you're talking to them.
A couple other things I'll suggest.
Have a new email policy.
This was also suggested in a world without email.
Email can be used for questions that can be answered with a single line or two, no back and
forths.
Email can be used to deliver files, right?
It's better than printing it out.
Email can be used for notifications or FYIs.
It cannot be used for back and forth interactions.
That has to be synchronous.
And how do you prevent this from being a million meetings?
will you have office hours every day.
Come to my office hours.
My door is open.
My phone is on.
If there's someone here, wait until they're gone.
Then we'll talk about it.
We're not going to do back and forth.
I'm not going to be in an inbox all day.
Your chief of staff can also get into loop here and keep a lot of things off of your plate.
Finally, no meetings for the first two hours of the day.
That's when you think through strategy and get the important work done.
As you said, and I'm going to quote your full message here, you described yourself as the freaking CEO.
You can make that happen as the freaking CEO.
There's a broader philosophical answer here, however.
This is more the road not taken.
If you read a book I like called A Company of One,
in this book, the key idea that's being pitched
is that exactly your situation,
as you're growing a company and is doing well,
the thing you're doing is in demand.
You have two options.
One, grow.
Great.
It's in demand.
So let's keep hiring people so we can bring in more revenue and we can come a bigger company.
And is what's argued in this book.
And I don't know why Jesse, maybe can look it up.
The author's name is escaping me.
Talk about midlife at the moment.
Paul is involved something.
I'm not sure why I can't remember his name.
We'll look that up.
But the book is called a company of one.
Jesse will look up the name of the author.
It might be Graham.
I'll look it up.
Yeah.
So there's, but what the, the, the,
Charles.
Paul Jarvis.
So I was right with Paul.
Yep.
There we go.
I actually write about him in my new book coming out in March, so I'm really forgetting
things.
Jarvis says there's two options as your company gets successful.
You can grow, which means you hire more people, then you can service more clients,
and your revenue, the overall revenue, the company can increase.
And this has the advantage, like, why do you do this?
So that your company's value goes up.
And it gives you the possibility of now we can sell this company maybe for $20 million
$10 years down the line.
The other option, he says, is use the leverage of your company being successful and in demand to make your life easier.
Great.
I'm going to charge more.
I'm going to do less.
Great.
Now, on half of the time I'm working, I can be matching my salary that I had before.
So you can otherwise, you can extract the value of what you're doing to make your life easier,
or you can extract a value of what you're doing to make your company grow more.
But as Jarvis says, and it's borne out in your example, if you go to the grow route, your life's
going to get busier.
And so you have to ask, is this potential buyout in the future more valuable to me than the fact that I could be making a really good living with a much easier, more autonomous, flexible job than I had before?
And it almost becomes a knowledge work version of that parable you hear again and again of the American business executive who goes on vacation in Mexico.
and he comes across a Mexican fisherman in a small village in Mexico.
And he says, hey, let me tell you, there's a lot of good fish out here.
You have a good fishing spot.
With my help, I could really help you grow, right?
Like, we could hire some people and you could have multiple boats go out.
As that gets more successful, you could level up to a really large commercial boat
and start selling the commercial contracts all around the world.
Like, this is a great fishing spot.
You have great expertise.
I could help this become big.
And this parable, the fisherman says, well, why would I, you know, why would I want to
want to do that?
And he's like, well, the exact one, like, if you do this, you could eventually sell the company
and have all this money and it would allow you to live in like a beautiful small town
by the coast and just go out and fish each day.
It's kind of similar, right?
I mean, isn't why do you want your $7 million share of the $20 million sale?
As you imagine, like, it'd be great.
I would have, you know, more control over my time and do some work with my money and have flexibility.
but you could probably get that within six months by instead just saying, hey, I'm in a lot of demand,
tripling my prices, cutting my hours and half, and going to learn to fish.
So keep that in mind more broadly, the audience out there more broadly.
Paul Jarvis, company of one, gives you an alternative response to success in your small company,
small startup or in your freelance skills.
All right, let's do one more question, Jesse, I feel it.
Last question's from Sean.
How can I handle better handle a work setback?
I'm an engineer and I've been processing a recent setback from a feature launch that didn't meet expectations.
The combination of already being mildly burnt out in this long delivery journey and the disappointing outcome have knocked me out of balance.
There's a sense of, meh, to both work and leisure activities that I usually engage in with much more zeal.
What have you done in this in your experiences and how can I bounce back?
Well, Sean, I mean, I would say you don't have to bounce back right away.
So this is this core idea that's part of my broader philosophy of slow productivity that, you know, I've been thinking about a lot because in March I have this book, eponymous book coming out on that topic.
Principle number two of slow productivity is work at a natural pace.
When you dive into that, what that means is, among other things, there should be if you want to embrace human nature.
And again, we're getting a bit of a Marcus Aurelius meditations vibe here, the embrace logos.
There should be more of a seasonality to your work.
And there's periods where you're really locked in and going after something.
And there are periods where you're downshifted because you know what?
You're exhausted and something didn't go well.
And your brain is burnt out and it needs a couple months.
And I don't think that's a bad thing.
You know, this notion of we should always be at some sort of consistent high level of execution is not realistic.
The people who say they're doing that are either lying or they're drugging themselves up to try to make it happen.
But human beings were not evolved this way.
Life in the Paleolithic was not at a consistent eight.
It was nines followed by lots of twos with the occasional fives.
It was up and down.
Early Neolithic was the same thing.
My God, we're in the fields all day in October.
And in January, we have nothing to do.
We're used to energy output being up and down.
We're used to the periods of extreme work versus periods of retreats.
charge.
Let's say just do some of that, Sean.
Lean into like, yeah, I don't need a plan right now to recharge or bounce back in two days.
I'm just, you know, doing a little bit more of the bare minimum work, be a little bit more clever
about my emails.
Let me take a month or two and be careful about, you know, when I take on the next project.
I'm going to take a couple days off, see if anyone notices, send a couple emails from the
movie theater.
You know you've done that before.
And I would say, don't worry about that.
Rest and recharge.
And then a month or two down the line, say, okay.
Okay, what are we going to work on next?
And then you cycle back up again.
I actually have a New Yorker piece about that, Jesse.
I don't remember the actual title.
It came out last year.
But basically it's a piece.
You can find that if you just go to my New Yorker archive, you know, Calnewport.com, you'll see on the cut.
There's a link to my New Yorker archive or just search Cal Newport, New Yorker from last spring or last winter.
I had a piece where I looked at everything we know about how early humans worked.
we're talking about the hunter-gatherer period.
So what do we spend 300,000 years doing as a species with respect to work?
And then I said, what can we learn about that for modern knowledge work?
And this idea that we should have much more seasonality and intense periods followed by rest periods
was one of the key ideas that came out of that article.
I elaborated on this a lot more of my new book as well.
All right, well, that's good.
Those are good questions.
I want to move on to a final segment here in a second, where as I do each month,
I want to talk about the books I read last month.
First, let me briefly mention another longtime sponsor of this show,
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Let's also talk about life insurance.
I mean, when else are you going to think about life insurance more than after reading
meditations by Marcus Aurelius?
Throughout this whole book, he says, think about your death.
So if you read this book, as I just did, you come out of it thinking, my God, I'm going to die.
I need more life insurance.
I'm convinced that Aurelius probably had a policy genius account that he worked for policy genius.
Because this whole book makes you think about life insurance.
So why don't you have more life insurance?
Erius told you to think about death.
What's going to happen to your loved ones?
The people depend on you.
Why don't you have more life insurance?
Because you don't know how to do it.
It's a task that's ambiguous.
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Did you see the part in the Isaacson book about Musk with the life insurance and like the PayPal
and how Theo was like saying, oh, we could have used that money.
Yeah, then he, for people who don't know in the Musk biography, I tell if I got this right,
Jesse, at some point during PayPal, very young, you know, 25-year-old Elon Musk takes out like a massive
Yeah, I think it was $100 million.
Like a $100 million life insurance policy on his life as a way to just signal I'm very, very important
to this company, you know, even though we're merged now and I'm not the sole like founder.
It's a classic move.
Jesse just took out $50 million in life insurance on himself.
Well, the thing was like in the part of that book, he almost died because of malaria.
Like if I guess if you went in like a day later, he would have been dead.
It's true.
And then it turned out.
So then he like, like Peter Thiel saw that and he's like, oh, my God.
You're like maybe it wasn't the past.
He might have needed that money.
Yeah.
Well, I don't want to say Peter Thiel.
They're friends now, I think, or at least they're friends after that part.
I don't want to say he gave malaria to Elon Musk.
Just saying.
I'm just saying, if you get a really expensive life insurance policy on yourself and then someone who would benefit from that, you get a really weird viral disease, look towards the people who would benefit from that policy.
All right.
Let's say a final segment.
I want to talk about the books I read in September.
As always, I aim to read five books per month.
So what did I read in September?
First book, this was something I started early in my summer at Dartmouth because I was
alone living near a pine forest, and then I didn't finish it till later.
And that was Lincoln Child's latest thriller, Full Wolf Moon.
Yes, it is a book about werewolves that takes place in the Adirondacks, the main character
who studies cryptic beast ideas is at this Adirondacks
Riders retreat and there are some grisly killings
and it looks like a werewolf is doing it.
A child always brings things back to naturalistic explanations
so you have to sort of piece together what's going on.
It was pretty good.
Next I read.
It's probably my favorite book of the month.
The Underworld by Susan Casey.
I'm a huge Susan Casey fan,
both of her writing and of the way that she left
the incredibly busy corporate magazine chief editor roles that she had to move to Maui and just write these narrative nonfiction books that all have to do with the ocean.
It started slow.
The first chapter is historical.
And I'm like, uh, maybe Susan lost her step.
It's talking about these early missions, like the Challenger.
We're talking about 18th century expedition, sailing ships to dredge the deeps and figure out how deep is the ocean and what's down there.
historical nonfiction.
It's okay.
Then she does what she does best, which is it comes to present tense, and she goes on adventures
where she meets these interesting characters and lets you into their life and adventures with them.
She starts hanging out with, for example, this eccentric millionaire who had a custom submarine built to go to the deepest parts of all of the ocean.
She goes onto the ship and goes down in that submarine.
She hangs out with the Triton submarine people and they go on these dives.
And once she's meeting interesting people and doing interesting things, it just becomes
fantastically readable.
Great book.
Susan does it again.
Book number three, I went back and re-read a book that I had first read years and years ago,
which was Oliver Berkman's 4,000 weeks.
I originally read that in galley form because I blurbed that book.
This would have been years ago.
But I didn't remember a little.
lot of it. So I went to reread it because I thought it would be relevant to a new book idea I'm
working on. And it held up. I remembered having enjoyed it the first time and I enjoyed it the
second time as well. Berkman brings a great, somewhat cynical British detachment to the ways
we think about productivity and accomplishment that really struck a chord when it came out.
So I definitely recommend that. Tim Ferriss, I think either interviewed Berkman. Actually, I think
Ferris actually read one of the chapters of the book or played one of the chapters of the book, the audiobook on his podcast.
I think you told him about the book.
I did, yeah.
So I had told Tim about 4,000 weeks, and then Tim really got into it.
And then I think he either had Oliver on or played a chapter of the book on his podcast.
So if you want to get a little deeper on it, you can check out that Ferris podcast.
That would have been, I don't know, last year or the year before.
Then I read Rethinking Fandom by Craig Kals.
a tara.
This is for my sports book book club that I'm in.
Just a bunch of dudes to get together and read books about sports.
Everything is interesting.
Everything you found them is interesting.
Short.
It's about all sports.
It's all sports.
I mean, it's a little bit, you know, it's, it has some interesting ideas.
I mean, it's basically like, he's a sports writer.
He's a baseball writer.
And he's like, I don't know.
I think sports are kind of problematic.
And so we should be careful about being sports fans.
They're owned by rich people and these rich people kind of suck.
And, you know, should we really be cheering for these billionaires and helping out their teams?
And we should just be kind of like less excited fans.
That's basically the gist of it.
And there's some really good points in there.
Obviously, it's well researched.
I mean, the arguments about the one that really resonated with me as a Washington Nationals fan was, do we really just have to accept tanking?
Like fans, like, yeah.
I mean, we have to tank to rebuild the team,
even though, of course, it's possible to go through a rebuild without tanking so hard if you just spent more money.
So who really benefits from?
There's two aspects to tanking, the rebuilding of the farm system and getting talent up.
And doing worse matters for that.
But also there's the element of like, let's keep our expenses low during the rebuild period.
That's only helping the owners.
So there's this argument of like, you know, we just tolerate that.
like, yeah, of course, like, the learner should not spend money on this baseball team because they're rebuilding.
So it's like, that's good for them.
Does it really good for Washington, D.C.?
You know, they have a team last year that, what, did 60 wins or less?
So that's interesting.
Sports book.
Final book, a thriller.
Great thriller.
Alastair McLean, this is 1963.
Ice Station Zebra.
Meteorological Station on the ice pack near the North Pole as this terrible fire.
and they're seeing out this distress call
and they're sending a nuclear submarine.
The only way to get to it
is to go under the ice
and then break up the ice near it.
And so they're going out there
and there's more to this fire
than was at first people suspected.
One of the cool things about this book
other than just like classic McLean,
he helped invent the modern thriller
and just it's, you know,
six thriller moments,
three major, three minor.
He has the whole formula down.
What's cool about it is
nuclear submarines were new.
So he's talking about all of these innovations that were new to nuclear submarines that wouldn't be surprising to us today.
But in 1963, no one had ever designed a boat before that spent more than a handful of hours underwater.
Some Marines pre-nuclear power were on to surface that you would only go underwater temporarily to approach the ship and fire.
And he was talking about how different it is.
How do you have a boat that stays underwater?
How does it navigate?
How do you throw out the garbage?
Also, how big these boats were because they had to fit nuclear reactors.
So it was cool.
I mean, I like that part of stuff we take for granted was very new.
So it was like a techno thriller of the time.
So there you go.
Those are the five books, Jesse, that I read in September.
And that's all the time we have for today's episode.
I like to give a final note at the end of every episode now.
If you're listening and you like it, do a review on iTunes or something.
subscribe. That does matter. Somehow they use that to figure out whether they show the show the show to
someone else. If you're listening and you want to watch, again, it's the deeplife.com slash listen.
Episode 268, the videos will be right there. All right. We'll be back next week with another episode
of the show. And until then, as always, stay deep. Hi, it's Cal here. One more thing before you go.
If you like the Deep Questions podcast, you will love my email newsletter, which you can sign up for
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