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August 24, 2025 6 mins

When you’re rushing through the day, it’s easy to lose sight of what actually matters. 

In this Quick Win episode, New York Times bestselling author Chris Guillebeau shares the reflection question he asks himself to reset and stay focused. Chris also reveals how a simple 40-minute check-in can help you course-correct in the moment, without relying on complicated productivity systems. 

Chris and I talk about: 

  • The reflection question Chris uses to decide if the day was valuable 
  • Why he believes the ordinary moments in life matter just as much as the big milestones 
  • The 40-minute check-in that helps him reset and make the most of his time 
  • How Chris uses these reflections as a reset—not a rigid system 
  • Why Chris doesn’t stick with one method forever (and that’s okay) 

Key Quotes: 
“Every day has something, at least one thing, that is special.” 
“If the last 40 minutes weren’t that valuable, what do I want to do differently next?” 

Listen to the full interview with Chris here.

Connect with Chris on Instagram, X (Twitter), and LinkedIn and his website, Listen to his podcast Side Hustle School, and check out his latest book Time Anxiety

 

My latest book The Health Habit is out now. You can order a copy here: https://www.amantha.com/the-health-habit/ 

Connect with me on the socials: Linkedin (https://www.linkedin.com/in/amanthaimber

Instagram (https://www.instagram.com/amanthai

If you are looking for more tips to improve the way you work and live, I write a weekly newsletter where I share practical and simple to apply tips to improve your life. You can sign up for that at https://amantha-imber.ck.page/subscribe 

Visit https://www.amantha.com/podcast for full show notes from all episodes. 

Get in touch at amantha@inventium.com.au 

&nbs

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Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:01):
In a world of constantly competing priorities and tasks, many
of us struggle to juggle everything and make time for
the things that really matter. In fact, it can often
feel like we don't even know what the most important
things to focus on are. But Chris Gillibode has a
reflection strategy that might just help you figure out what

(00:22):
really deserves your focus. Chris is a New York Times
best selling author whose book One hundred Dollars Startup sold
over half a million copies and his side Hustle School
podcast has surpassed one hundred million downloads worldwide. In this
quick Win, Chris reveals his trick to figuring out what
is and isn't a valuable use of your time. Welcome

(00:50):
to How I Work, a show about habits, rituals, and
strategies for optimizing your date. I'm your host, doctor Amantha Imber.
I like some of the practices in the book that
are more around get around, like that deeper reflection. And
I think one of the questions that you recommend people

(01:14):
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 so?

Speaker 2 (01:23):
What 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

(01:48):
and 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

(02:10):
come to 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

(02:32):
routine or 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

(02:54):
like you made some progress in something, You spend 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 A, B,

(03:17):
and C, and 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 1 (03:36):
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,

(03:56):
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 missed around, you know,
I spent too much time on social media or whatever.

Speaker 2 (04:13):
Sure, sure, okay, that's a good point. Yeah, so 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, If 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

(04:33):
day that we will 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 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

(04:54):
differently for the next forty minutes, 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 1 (05:02):
Yes, I love that question, and I'm curious how often
do you ask yourself that question.

Speaker 2 (05:10):
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

(05:30):
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?

Speaker 1 (05:48):
You know?

Speaker 2 (05:48):
But this is not like a lifelong practice. It's something
that helped me 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

(06:08):
have would have like systematized it and had it, like,
I don't know, built some spreadsheet or something for it.
And thankfully I don't do things like that now.

Speaker 1 (06:17):
I hope you enjoyed this little quick win with Chris.
If you'd like to listen to the full interview, you
can find a link to that in the show notes.
If you like today's show, make sure you get 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 Cooler Nation
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