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Deep Questions with Cal Newport

IN-DEPTH: The Art of Non-Conformity (w/ Chris Guillebeau)

Deep Questions with Cal Newport

Cal Newport

Technology, Self-improvement, Education

4.81.3K Ratings

🗓️ 12 June 2025

⏱️ 68 minutes

🧾️ Download transcript

Summary

In this episode of IN-DEPTH, Cal is joined by Chris Guillebeau, the author of the new book, TIME ANXIETY, and creator of the beloved Art of Non-Conformity blog and World Domination Summit annual conferences. Cal and Chris reminisce about their old days as early advice bloggers and dive into his new ideas about re-thinking our relationship with time.

Transcript

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0:00.0

I'm Cal Newport, and this is In-depth, a semi-regular series in which I talk to interesting people about the quest to cultivate a deep life.

0:17.1

I'm excited about today's guest. It is the author Chris Grubeau.

0:22.5

He has a new book out called Time, Anxiety, The Illusion of Urgency and a Better Way

0:28.1

to Live.

0:28.8

So clearly this book topic is one that you know I'm going to be interested in, and we

0:32.7

have a good conversation about it.

0:34.9

But I was also excited to have Chris on the show because he's a blast from the past for me.

0:40.9

We intersect strongly back in that early stage of my career, the 2000s, when I was blogging. I'd written my first student books and I had the study hacks blog. And I knew Chris from back in that world. So we sort of go

0:56.9

back and relive a little bit what that early stage of new media was like where blogs reigns

1:02.2

supreme. We talk about these fantastic conferences that Chris organized called the World

1:07.0

Domination Summit, including this famous one within sort of our circles, I think it was

1:13.4

the 2011 or 2012 World Domination Summit. You can find my video of me talking about so good they can't

1:18.6

ignore you. It's online, but it's just like 800 person venue. And it brought together all of these

1:24.2

different people at early stages in their career that would go on to do really

1:27.9

interesting things so you know i was there talking uh bernay brown was there as well that was like

1:33.0

one of a couple different there's a period there i was doing multiple different stuff with bernay

1:36.4

gretchen rubin i think was there uh susan kane from uh quiet was there it was just like this this really interesting period of where people are coming together.

1:47.9

That's where I met the minimalist for the first time.

1:49.7

Like they were just coming up and it was all this energy at this one place.

1:53.8

So we have a lot of interesting discussions, not just about his new book, Time Anxiety, which is great.

1:58.7

You should check it out.

1:59.4

But also about what was that world like, that world of online ideas like in that pre-social media age?

...

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