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June 4, 2025 23 mins

So much of how we spend our time is shaped by invisible rules we never agreed to. From how often you check email to how long you take to reply, these “time rules” run in the background - until you stop to question them. 

In part two of this conversation, New York Times bestselling author Chris Guillebeau joins me to talk about how to break free from these hidden rules and why living well beats chasing productivity hacks any day. 

Chris shares the question that helps him reset when he feels stuck, the “eighth day of the week” exercise that can change how you use your time, and his take on why the system or app you use doesn’t really matter

In this episode, Chris and I talk about: 

  • The “eighth day of the week” exercise for making time for what matters 
  • How to spot the hidden “time rules” running your life 
  • The 40-minute reflection rule that helps Chris stay on track 
  • Why Chris believes the greatest productivity hack is to love what you do 
  • How to decide what really matters—day by day, moment by moment 

Key Quotes: 

“I thought I was getting better at the wrong things.”

“The greatest productivity hack is to love what you do.”

 “How valuable were my last 40 minutes?”

 “Did today matter?” 

Connect with Chris on Instagram, X (Twitter), and LinkedIn and his website, Listen to his podca

Mark as Played
Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
We all have rules that kind of govern how we
spend our time, and some of this is internalized as
a child or as a young adult. Maybe some of
that serves you still there could be something that might
serve you better.

Speaker 2 (00:13):
Today we are diving into part two of my chat
with New York Times best selling author Chris Gilibo. In
this episode, Chris shares how to break free of the
unnecessary subconscious rules that often waste your time and his
trick to figuring out what is and isn't a valuable
use of your time. Oh and by the way, if

(00:34):
you missed part one of this chat, then you might
want to check out your feed in How I Work
and go listen to part one first.

Speaker 1 (00:43):
Like, I was pretty good at the productivity game. At
a certain point, I just realized, like, ultimately, I think
I'm getting better at doing the wrong things. The way
that my life is going to be disrupted is much
more likely because I fail to take action. The far
greater problem is my own resistance. The way that I
address that is like.

Speaker 3 (01:07):
Welcome to How I Work, a show about habits, rituals,
and strategies.

Speaker 2 (01:12):
For optimizing your date. I'm your host, doctor Amantha Imber
what have you found, because I imagine you know, you've
been doing lots of publicity for the book, which practices
seem to have resonated with the most amount of people.

Speaker 1 (01:30):
One that people really like. I have been doing a
lot of events here in the States, have been in
about ten cities so far. I'm doing a couple of
stops in Canada in a couple of weeks, hopefully beyond
North America as well at some point. One of the
things people respond to a lot is this idea of
the eighth day of the week. And so it's it's

(01:50):
like imagining you have an extra day every week, and
what does that look like? And how would you choose
to spend this day which is a recurring day. And
so that's the big difference from thinking about like what
is your ideal perfect day. That's kind of a classic
like thought exercise, and it can be helpful, but it's
also maybe there's some pressure involved with that. It's like

(02:11):
my perfect day, like my one perfect day, you know,
And if you think about what if I had an
extra day that came around fifty two times a year,
like how would I spend that? And so that's something
that's additive. You could like, there's a lot you could
do if you had this extra time that came around
every week. You could write a book, you could learn
a language, you could learn all kinds of other skills.

(02:31):
And so people have found that to be kind of interesting.
As they think about like freeing up their time, they're
also thinking about how would I choose to spend it,
and so those two things can kind of work together. Well,
I'm sure there's some others. That's the first one that
comes to mind.

Speaker 2 (02:44):
Yeah, I liked a con't rid of the terminology used,
but helping people to unpack what are the assumptions that
they have around the time. I'm trying to remember the
language that you used around that and really challenge those
assumptions around oh we do this then, or this is

(03:04):
how we spend our time at this point in time.
Tell me more about that and help me with the
remember the language that you use, because I really liked
that thinking about what are the assumptions that I'm off
for writing.

Speaker 1 (03:15):
By for sure? Yeah, I think I was writing about
time rules. Yes, this notion of like we all have
rules that kind of govern how we spend our time,
and some of this is internalized, like as a child
or as a young adult. In some of our primary relationships,
this is like how we spend our time, and this
is how things work, and this is what time that
meal times are at this time, you know, based on

(03:37):
when you are a kid typically, and this is how
long it's acceptable to go before you call someone back
or message them back. And you know, there are many others,
but basically, like how we kind of go about our
day and spend our time. Most of us have not
actually thought about that very intentionally. It's not something that's
ever really brought up about, like, Okay, you're living your

(03:57):
life this way because this is what you learned, this
is what your parents did. Maybe some of that serves
you still, but maybe you know, you're a different person,
it's a different time, it's a different generation xxx, Like
there could be something that might serve you better, So
it's helpful to maybe consider, like what are the time
rules that govern my life and what might be better,

(04:20):
you know for me. And these can kind of coincide with,
you know, other life hacks or other things that you
do just to try to, you know, have a better life.
Like I'm looking at my phone for an hour before bed.
Maybe I should try not doing that, you know, or
you know, I have this belief that I we were
talking about email, that I must respond to every person

(04:42):
you know, the same day, or I must respond to
them at all. Well maybe that's the case, but maybe
maybe not, you know, there could be something else. So
I think it's very freeing. It can be very freeing
for people once they understand that a lot of how
they spend their time is governed by these kind of
assumptions that are kind of baked in, and they can
go and perhaps rewrite some of those or create something

(05:04):
that serves them better.

Speaker 2 (05:05):
What are some of your time rules or time assumptions
that you have that you've crushed. You're questioned, crushed is
a bit aggressive, Let's go questioned.

Speaker 1 (05:15):
Questioned, I mean I like crush depending on the context.
So I'm sure you've been familiar with this for a while,
but I hadn't really known a lot about a lot
of this research about the limited amount of cognitive attention
that we have each day and it's only a few hours.
And I've also found that shifting a little bit as
I get older. I do feel like maybe this is

(05:36):
this could be somewhat perception, but I do feel like
I used to be able to process or focus a
lot more. And so whether that's my perception or reality,
I do feel that focus is more limited for me
than it used to be ten years or twenty years ago.
And so whatever the case is, I need to be
mindful of that. So this idea that we only have
maybe three hours a day on average of actual cognitive attention,

(06:01):
and it's just true, you know, for prolific people throughout history,
and you know Mozart and Beethoven and all these artists
and famous writers and everybody else, like they pretty much
got like three hours a day. And so I've tried
to be really really careful about what does that time
look like for me and how do I spend it?
So I've tried to be careful. That's something I've tried
to like think a little bit more about.

Speaker 2 (06:23):
So how do you then, like protect those precious focus hours?
I don't know, like, do you have new rules in
place or ways that you think about your day that
have helped served you.

Speaker 1 (06:34):
I feel like more than protecting them from anybody else,
I am the problem. Like it's me, I'm the problem.
I feel like the way that my life is going
to be disrupted is much more likely because I fail
to take action, I fail to plan or actually like
use that time. Well, you know, there's nobody else that's

(06:54):
going to take that time away from me. It will
only be taken away from me, you know, if I
agree to do things in certain hours that I shouldn't
do them or whatever. You know, Like, the far greater
problem is my own resistance. And so I think the
way that I address that is, like, like I always say,
the greatest productivity hack is to love what you do.
I know that probably sounds very basic and reductive, but

(07:16):
if you actually love what you do, it's going to
be so much easier to get up and go and
do that thing, versus, Oh, I have to do this thing.
How can I psych myself up? How can I manufacture
motivation to do this thing that I have to do?
And you know, it's theoretically possible to do that for
a certain amount amount of time, But wouldn't it be
so much better to like craft a life or craft

(07:39):
at least some projects some parts of our life around
those things that we're really excited about, And then you know,
you feel a lot less resistance to you know, diving
into them and working and they're still resistance. There's still problems,
but honestly, I feel like that solves like eighty percent
of the motivation problem.

Speaker 2 (07:56):
We will be back with Chris soon and when we
writ down we'll discuss why he stopped trying to use
and follow productivity hacks and his trick to figuring out
what is and isn't a valuable use of your time.
If you're looking for more tips to improve the way
you work can live. I write a short weekly newsletter

(08:19):
that contains tactics I've discovered that have helped me personally.
You can sign up for that at Amantha dot com.
That's Amantha dot com. It's funny, like when I think
about time rules actually, and again, when I was reading
the book, I was reflecting on this a lot, and

(08:39):
not to bring it back to email, but it's my
achilles heel. And interestingly, I find that for a lot
of the you know, the productivity folk that I have
on the podcast, Like I think of Jake Napp, for example,
who I've had on a few times, and I feel like, yeah,
email was his achilles heel, and there have been others.
And one of the things that I've been catching myself

(09:01):
thinking is that generally, like ninety percent of the time,
my phone does not have email on it, So don't
have my email app on my phone, which I think
in and of itself is quite unusual. And I do
that so that I can't just mindlessly check email whenever
I want when I'm on the go, but sometimes I'll
need it on my phone, whether it's there's a link

(09:21):
to tickets that I've bought for a show, and so
I'm just like, I'll just get email on my phone
so I can do that easily and frictionlessly, and then
it'll stay on my phone for a few days because
I'll forget to delete it, and I will experience this
sense of stress when I see an email come through,
because my brain whenever it reads an email, and I'm

(09:42):
sure this is how most people's brains work, is that
they go, I need to respond to that, and then
the stress starts because there's something that is on how
to do list that is not yet done, and I
think about what if I haven't seen that email for
two days, I wouldn't have had that thought, and I
would have responded at some stage in the future, and

(10:03):
that worry wouldn't have been there, or that task taking
up space in my mind wouldn't have been there. Just
these self imposed deadlines and assumptions cause us a lot
of stress, whereas if we just didn't see the thing,
the stress wouldn't be there. And just how artificial it is?
Can you relate to any of this, Chris No.

Speaker 1 (10:24):
One hundred percent. I think it's interesting. Two things. One,
it's you know, even if you decide I'm not going
to respond until later, that thing is already like in
your brain, like you've already taken it in, so you're
going to be it's going to be like you're going
to be thinking about it, or even if you're not
thinking about it, you're not thinking about thinking about it,
and you are thinking about it. Right. But also the

(10:45):
second thing is is like, is it just the notification
that's the problem, right, Because if you have the email
app on your phone but you don't have the notifications
turned on, then you don't actually see when the new
messages are coming in. Right, it's accessible to you if
you need to go get the tickets for the show
or whatever else. But it sounds like in that case,
maybe the notification is the problem.

Speaker 2 (11:04):
I don't have my notification switched on for email, This
is me.

Speaker 1 (11:08):
How do you know that the email has come through.

Speaker 2 (11:11):
Because I check it? Because I don't really have social
media on my phone. My phone is quite boring, and
so when email is on it, it's like, well, that's
an exciting thing that's going to possibly give me a
dope for meat hit. If there's like a good email
in there, it's entirely my own doing, which is why,
as many productivity people say, don't rely on willpower. Set
up your systems so that you're not relying on willpower

(11:33):
to not do the thing. And so if email is
not on my phone, I don't think about email and
I don't check my email.

Speaker 1 (11:38):
I kept trying to get better and better at doing
these things, and this is part of why I wrote
the book, as like I tried to follow all these
rules right, and these habits about like I shouldn't have
this app on my phone, and this is how my
notifications need to be set up. And there's a thousand
other things right, like we've all read them in like
all the books and so on, And I guess I
was pretty good at it, Like I was pretty good

(12:00):
at the productivity game. And at a certain point I
just realized what am I actually getting better at? Like,
ultimately I think I'm getting better at doing the wrong things,
or even if some of those things can be helpful,
like the more I do them, the more things that
will come back. And are these things really making it,
you know, measurable difference in my life or some of

(12:22):
them actually stressing me out? You know. It's like the
number of questions I get about even from people who've
read the book, because I'm like, the system doesn't matter.
You should probably have some kind of list making system
and task things. It's fine, but it doesn't really matter
what it is. You should do what's best for you.
But still I'm going on book tour and people are like,
tell me a little bit about your productivity setup and

(12:43):
your stack and like what apps you use. I'm like,
I'm fine to talk. I don't mind talking about that.
But I guess for me again, that was the problem.
Like I thought those things were going to help me
or like remedy the distress I felt, and really they
did not. And so honestly, the more simple the solution
you can find, the better. Or if there's some productivity
tool that requires a lot of learning, then I don't

(13:04):
think that's a helpful tool, you know, if you're learning
to edit film, if you're learning to code, Like, these
are things in which you need to go and like
spend hours maybe watching some courses or YouTube and such,
because there is like higher knowledge required there. But for
learning like these various systems and such, you know, keeping
up a task, it should be very simple. So all
that to say, like learning these things and trying to

(13:26):
apply all these tools was not helpful to me.

Speaker 2 (13:28):
Ultimately, Oh gosh, it's funny. I'm amused by that question
because I feel like it mildly misses the point of
the book. But then also part of my mind is going, hmm,
what software does Chrissy use what it is told? And
it's got me thinking, But that would just be totally
beside the point. I like some of the practices in

(13:49):
the book that are more around get around, like that
deeper reflection. And I think one of the questions that
you recommend people ask is what is special about this day?
Can you tell me more about like when should we
ask that question? And what is the impact of doing sorry, what.

Speaker 1 (14:08):
Is special about this day? I think I came to
that practice out of the belief or the concept that
when we think about life, people tend to think about
big moments. They tend to think like these milestones of
like here's this thing that happened in my life. It
was like a one off kind of thing. But really
our lives consist much more of like ordinary moments and

(14:33):
just the day to day, and a lot of that is,
you know, unmemorable or maybe in some ways like to
make it more active, forgettable, but yet at the same time,
like every day has something at least one thing, probably
more than one thing that is special. And for me,
I've tried to work on being more present, on noticing,
more on mindfulness, but I also had to come to

(14:55):
it from a different perspective because I'm not really good
at meditation, and I've tried some of those practices and
they don't work super well for me. But to get
to the same place, like noticing what is special about
this day, the ordinary moments that make up our life,
and there are things we can do to like inspire
that specialness. There are things we can do to like
make days special, whether it's a change in routine or

(15:18):
just doing something a little bit different or asking what
matters right now? I also like this one about did
today matter? So you ask this question at the end
of the day, like looking back, and it's really interesting
because it's not like asking was it a good day
or a bad day? You know, like sometimes you can
actually have a bad day, but you feel like you

(15:39):
made some progress in something, you spent time with people
that you loved, like you actually felt alive even though
the day was kind of stressful for whatever reason. Or
you can have days in which everything was kind of fine,
but you look back and you're like, today, I'm not
really going to ever think about again. And so if
you think about did today matter and being able to
answer yes, today mattered because of AB and C and

(16:03):
those answers might be different for each person, that's helpful
because the next day you want to do more of
those things and you know, hopefully like build up this
streak of days that matter to you. So I think
all of those things together, it's like pointing towards mindfulness,
but maybe a way that's a little bit different from
how other people have gotten there.

Speaker 2 (16:20):
It's an interesting question did today matter? I feel like
and I'm going to try this asking myself that question
certainly at the end of today and hopefully for a
few days. But I feel like I would answer that, well,
of course it did, and I would look for the meaning,
which would ultimately be a good thing to reflect on. Well,

(16:41):
what did matter about today? Because I think as humans,
you know, we don't want to go I've just wasted
a day, even though I think a lot of people
have that thought. At the end of the day, today
felt like I wasted it. I messed around, I you know,
I spent too much time on social media or whatever.

Speaker 1 (16:58):
Sure, sure, okay, that's a good point. Yeah, you could
like look back and find the meaning in it and
find what was special. But maybe here's another way to
think of it. Then, So if we think about that pressure,
another question is like how valuable were my last forty minutes?
And so this is a much shorter time period, and
I do think if most people ask that question, there
are lots of times during the day that we will

(17:19):
say the last forty minutes, I don't know that they
were that valuable. And so value can also mean productivity,
It can mean like satisfaction, enjoyment, learning. You know, there's
lots of different ways for your time to be valuable.
But if you say, at any point during the day,
actually the last forty minutes not that valuable. Then you
can make a little shift and be like, oh, what
do I want to do differently for the next forty minutes,

(17:40):
And so it's not that long of a time that
you have wasted, and it gives you a little chance
to reset. Perhaps.

Speaker 2 (17:46):
Yes, I love that question, and I'm curious how often
do you ask yourself that question?

Speaker 1 (17:54):
A lot of these kind of activities and practices I
kind of cycle between, and I'll be doing one for
a while and then I'll do something else for a while.
For a long time, I was really into the five
goals thing. Do you know that whole model of like
you can only have five things, and you make a
list of your top twenty five, and then you choose

(18:15):
like the top five and then the other twenty or not.
Things you do on the side. There are things that
you absolutely must not do because they're keeping you from
your five. That's a whole like other rubric. I was
into that for a while, and so every day for
like six months, I would have like a paper journal
and I would write down like one, two, three, four, five,
like did I do that? You know? But this is
not like a lifelong practice It's something that helped me

(18:36):
for a little while, and then I kind of moved on.
So when you say, like this particular one, how often
am I doing it? I think I'm probably doing it
a couple times a day. But it's not like I
have like an alarm setup, you know, on my phone,
and it's not like I have a journal that It's like,
that's the old old Chris would would have like systematized
it and had it, like I don't know, built some

(18:58):
spreadsheet or something for it. And thankfully I don't do
things like that now.

Speaker 2 (19:03):
What other practices like, because I always love knowing, like,
particularly when you've written a book, and I mean you
would have submitted this manuscript twelve months ago or something
like that. I imagine like one of the things I'm
so curious about. And I feel like I've experienced when
I'm doing publicity for the books that I've written, it's like,
oh gosh, I've either moved on from that or I'm

(19:25):
only using a subset of what I wrote about. What
are those things like right now? You know in the
last few weeks that you're like, yeah, I'm doing that
a lot.

Speaker 1 (19:34):
Actually, Well, at the beginning of this conversation. I think
we touched on legacy versus living well. That is something
that I think about a lot. I try to think
about what is living well look like for me at
this season. I am very like project focused and like
goal oriented, and I'm always going to be that way.
Like I haven't given that up. I think I said
that too, but I'm often going back to, like, Okay,

(19:57):
what should I be doing right now? You know things
I could be doing. And then also I wrote a
good bit about choice and about how life ultimately is
about choice and choosing and there are more things that
we want to do then we'll be able to do.
Desire is limitless, and there's actually joy in selecting and

(20:18):
choosing and making decisions. And so I started writing the
book because I felt like, IRE's not enough time. I've
missed my I've already pequked and I've missed my chance
or whatever, and like now I'm like, there's still time.
There's still time for things that I can do new things.
You know, I can change, I can adjust and adapt.
And so I think that is something that is very

(20:39):
much with me. I know that sounds kind of a
big picture, but it actually really doesn't form like my
day to day and think about what is it that
I want to work on. I just put on a
new event a couple of months ago in Austin, Texas
for the neurodivergent community. And like I used to produce
another annual event. I did it for ten years with
David Fugate, our mutual friend and literary agent, and you know,

(21:00):
we built that event up year after year and then
it came to a natural end. So I wanted to
start this new event, and so to make a long
story short, I did it and it went really well,
and it was for a relatively small number of people.
There were just like a couple hundred people there, and
it took several months of like full time work. So
on the scale of like you know, like from like
a hard business and analysis like is this the best

(21:22):
thing for me to be doing? Maybe somebody would say no,
but I'm like, this is absolutely what I should be doing.
Like it was totally the right thing. I'm excited about,
you know, building it more for a year or two.
So maybe just thinking about what really matters and how
do I apply that is something that I try to do.

Speaker 2 (21:37):
Have you changed, you know since writing time? Anxiety like
your process of thinking about what projects you do take
on versus what you say no to or get left
on the cutting room floor.

Speaker 1 (21:50):
I don't know if the process has changed so much
as I no longer feel bad or not as bad
about the things I'm not doing or the things that
I'm not great at. I have a lot of friends
who are really good at social media, and they're just
crushing that, and they're all these profiles and like new
videos and reels every day. It's just so so great

(22:10):
to watch. And you know, I used to feel very
envious of it, and now I just feel like, I mean,
maybe I feel like ten percent envious of it, but
it's more just like, that's what they do. They're really
good at that. That's not me. You know, There's other
things I'm going to do. So I don't know if
it's the process that's changed, it's more of the FOMO
has decreased. So that's good, that's awesome.

Speaker 2 (22:31):
Well, Chris, how useful has the last forty minutes been
for you? Has it been a good use of your time?
Longer than forty minutes we're recorded for though.

Speaker 1 (22:39):
I really love this conversation. You have asked some really
smart questions. You actually read the book, I can tell,
and you are someone who's worked in this field for years.
I have a lot of respect for you. It has
been a wonderful conversation and a wonderful use of forty
plus minutes.

Speaker 2 (22:54):
I hope you love the second part of this chat
with Chris as much as I did. I am definitely
going to be trying that forty minute reflection tip. I
personally think that is just gold. Now. If you want
to learn more about Chris, I highly recommend checking out
his new book, Time Anxiety. You'll find a link to
that in the show notes. If you like today's show,

(23:17):
make sure you gid follow on your podcast app to
be alerted when new episodes drop. How I Work was
recorded on the traditional land of the Warrangery People, part
of the Cool and Nation
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