Link to submit questions: bit.ly/3U3sTvo

- Deep Dive: Quiet Quitting [4:00]

- How can I motivate my kids to have Cal’s work ethic? [24:28]
- What are Cal’s tips for writing better articles? [34:48]
- Are someday/maybe lists worth it? [44:33]
- How can a researcher embrace slow productivity? [48:24]
- Why did Cal switch from Roam to Obsidian note-taking software? [53:47]

CASE STUDY: A World Without Email got my team through a crisis [57:01]

- How can I concentrate on work with so many bad things happening in the world? [1:09:31]
- What if I don’t enjoy the deep life I designed? [1:20:16]

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Thanks to Jesse Miller for production, Jay Kerstens for the intro music, and Mark Miles for mastering.

- Deep Dive: The art of “no” [7:06]

- CALL: Anxiety and timeblock planning [27:38] 
- How do I choose a hobby to master? [37:01]
- Should I leave my job? [43:31]
- How do I break into a knowledge work? [49:00]
- How do I overcome career anxiety? [53:55]
 
CASE STUDY: Closet Office [1:05:10]

- CALL: Thoughts on Monday.com [1:13:38]
- What’s the difference between a quarterly and strategic plan? [1:21:45]
- How do I figure out my values? [1:23:10]

Thanks to our Sponsors:

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Thanks to Jesse Miller for production, Jay Kerstens for the intro music, and Mark Miles for mastering.

- Deep Dive: Will 4-Day Weeks Solve Burnout? [7:01]

- How do I know if I’m doing too much? [24:03]
- Who invented the idea to “follow your passion”? [34:11]
- How can an ER doctor manage his schedule? [41:46]
- CALL: How do you know when it’s time to rest? [45:48]
- Nerd Alert: Is the future of computing more local? [49:59]

- Books Cal read in August 2022 [59:31]

- CALL: What watch does Cal use? [1:16:51]
- How do I create a Feedback Council? [1:25:04]
- Did Jordan Peterson and Bret Weinstein get weirder after leaving academia? [1:28:06]

Thanks to our Sponsors:

This podcast is sponsored by BetterHelp.

expressvpn.com/deep
betterhelp.com/deepquestions
ladderlife.com/deep
mybodytutor.com

Thanks to Jesse Miller for production, Jay Kerstens for the intro music, and Mark Miles for mastering.

- Deep Dive: How does Cal organize his life? [4:47]

- How do I improve my estimates of how long a task will take?  [27:49]
- How does Cal feel about open office spaces? [30:01] 
- Does listening to a podcast count as reading? [40:54]
- How do I plan a wedding without drowning in minutia? [43:40]
- I lost my love for work. Should I try to get it back? [50:03]

- Does Cal struggle with comparing himself to others? [59:18]
- How do I reset my ambitions after buring out? [1:08:06]

Thanks to our Sponsors:

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Thanks to Jesse Miller for production, Jay Kerstens for the intro music, and Mark Miles for mastering.

Please take a moment to provide feedback on the podcast using this survey:
bit.ly/3zMTLXp

DEEP DIVE: Loops, Networks, and Links [5:32]

DEEP WORK QUESTIONS

- How do I track a long-term project? [30:52]
- How often should I check email? [36:23]
- How do I get my workplace to be less “hyperactive”? [42:14]

LISTENER CASE STUDY: Diane rents an office near her house [46:08]

DEEP LIFE ACADEMY: Lifestyle-centric career planning [53:39]

—

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Thanks to Jesse Miller for production, Jay Kerstens for the intro music, and Mark Miles for mastering.

Click Here To Take Cal’s Survey: https://bit.ly/3zMTLXp

Cal reacts to the news: TikTok and the Fall of the Social Media Giants [3:05]

- How long should I wait for someone to respond to my email? [32:21]
- Do you recommend having multiple email accounts? [35:21]
- Is there a place for “Inbox Zero” in Cal’s productivity system? [38:15]

Habit Tune-Up: Docket Clearing Meetings [44:44]

- How do I balance my many interests after quitting my job? [55:33]
- Why am I stuck in my pursuit of depth?  [1:01:30]
- How can we convince the masses to live deeper? [1:06:57]

Thanks to our Sponsors:

Blinkist.com/Deep
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Thanks to Jesse Miller for production, Jay Kerstens for the intro music, and Mark Miles for mastering.

Habit Tune-Up: To-Do Lists Are Inhumane [2:03]

- Is distracted deep work the same as shallow work? [18:10]
- How does Cal do quarterly reviews? [23:03]
- What should I include in my quarterly plan? [25:03]
- How do I save my failing productivity system? [27:34]
- Can I sell a book without social media? [36:12]

The Five Books Cal Read in July 2022  [47:56]

- How do I manage the anxiety of not achieving a goal? [1:11:22]
- How do I handle having too many ideas? [1:15:05]

Thanks to our Sponsors:

Blinkist.com/Deep
Eightsleep.com/Deep
ExpressVPN.com/Deep
PolicyGenius.com


Thanks to Jesse Miller for production, Jay Kerstens for the intro music, and Mark Miles for mastering.

In today’s episode, we try something different: a special two-part conversation in which Cal coaches his longtime friend, comedian and podcast pioneer Jamie Kilstein, through a digital declutter. The first part of the conversation ends with Cal’s prescription for Jamie, while the second part picks up six weeks later to check in on how things actually went.


Thanks to our Sponsors:

Miracle.com/Cal
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Thanks to Jesse Miller for production, Jay Kerstens for the intro music, and Mark Miles for mastering.

With Cal away on vacation, he decides to tackle 8 questions in a row, all in one take, with no breaks!
 
Ian Fleming’s writing process [1:13]
 
- How can I get a tech job without credentials? [8:04]
- How do I make progress on tasks in a chaotic job? [10:52]
- Why do you have a problem with social media? [16:07]
- What should I do to succeed in my first internship? [24:16]
- What does Cal think about YouTube shorts? [26:37]
- Is it possible to avoid studying all the time in medical school? [29:14]
- What do you think of Oliver Burkeman’s work on productivity in Four Thousand Weeks? [37:51]
- Can I maintain a social life if I move to the country? [43:41]
 
 
Thanks to our Sponsors:
 
Blinkist.com/Deep
Wren.co/Deep
Zocdoc.com/Deep
Ladderlife.com/Deep
 
Thanks to Jesse Miller for production, Jay Kerstens for the intro music, and Mark Miles 
for mastering.

With Jesse away on vacation, Cal decides to tackle 10 questions in a row, all in one take, with no breaks, covering everything from complaints about Cal’s inaccessibility, to teaching deep work in schools, to a long pontification (read: rant) on the podcasting industry.

- Finding time to self-study [5:38]
- Why Cal is a bad correspondent [11:44]
- Can everyone become so good they can’t be ignored? [25:32]
- Should temperament affect job choice? [29:06]
- Teaching deep work in schools [33:20]
- When does Cal listen to podcasts? [37:46]
- How do I succeed in podcasting? [38:57]
- Why is Cal so contrarian? [56:22]
- How do I stay a digital minimalist after having a baby? [59:31]
- How do I teach my family and friends about the deep life? [1:02:23]

Thanks to our Sponsors:

MyBodyTutor.com
EightSleep.com/Deep
ZBiotics.com/Cal
Blinkist.com/Deep

Thanks to Jesse Miller for production, Jay Kerstens for the intro music, and Mark Miles for mastering.