The Art of Humor Writing

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Cal Newport (calnewport.com) is an associate professor of computer science at Georgetown University who previously earned his PhD from MIT. His scholarship focuses on the theory of distributed systems, while his general-audience writing explores intersections of culture and technology.

Cal is the author of seven books, including, most recently, Deep Work, Digital Minimalism, and A World Without Email. He is also a contributing writer for The New Yorker and the host of the Deep Questions podcast.

Please enjoy!

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The one lesson from comedian, actor, author, and mean banjoist Steve Martin that hit Cal “like a lightning bolt.” [05:40]

What does it mean to be living “the deep life?” [08:17]

The story of Cal’s Study Hacks blog, why he needed to write his first three books, the unique way he went about securing his first book deal as an unproven 20-year-old, and how he signed with the agent who’s been with him for the past 20 years. [11:20]

What was Cal’s focus in high school and college? [24:03]

How did Cal consciously set out to sharpen his writing skills in college, and what part have humor and mathematics played in their evolution? [26:14]

What advice does Cal have for someone who wants to hone their funny bone for humor writing? [31:14]

Fresh thoughts on slow productivity. [40:47]

There’s no way to know if someone like Isaac Newton would have achieved greatness had he lived in the present day — when slow productivity isn’t the social default. But are there any contemporary examples of people who have mastered slow productivity in spite of 21st-century distractions? [46:36]

These days, Cal is well-known for eschewing the temptations of social media. But why did he initially refuse to sign up for Facebook when it was the shiny new thing everyone was talking about? [53:11]

Documents and disciplines Cal and I find instrumental in crafting the lives we desire. [58:41]

How Cal integrates seasonality into his routine for ample periods of downtime, where he roams to recharge and reset, and his pen of choice for taking notes both literary and mathematical. [1:06:11]

Why Cal and I are big fans of Scrivener software for writing. [1:13:37]

How Cal uses Trello to organize tasks under the different hats he wears throughout the day. [1:17:17]

Books in the “anti-productivity” category Cal thinks might be worth your while. [1:21:34]

Who was John Newport? [1:28:18]

Who Paul Tillich was, an explanation of the confusing term “Christian apologist,” and understanding why Cal describes himself as a concentration apologist. [1:30:53]

How does Cal focus on contemplation and matters of the soul? Why does he believe someone who’s quick to dismiss a philosophy or religion without trying to understand its most basic foundation does themselves a disservice? What are his thoughts on the takes Sam Harris and Jordan Peterson have on moral frameworks, and what need is satisfied by such contemplations? [1:33:06]

Considering the spiritual as an exercise of meticulous craft and creation, and understanding that some materials serve the purpose better than others. [1:41:09]

With so many options from which to choose, how might someone who has had either bad experiences with religion, no experience with religion, or no interest in religion explore spirituality? Are we programmed to seek out religion? [1:45:44]

Can you make it through Cal’s 30-day digital minimalism declutter? Here’s how to set the rules that are right for you and give it a whirl. [1:54:13]

What shutdown ritual does Cal use at the end of his workday? [2:03:06]

Parting thoughts. [2:05:07]

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Past guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, Balaji Srinivasan, Sarah Silverman, Dr. Andrew Huberman, Dr. Michio Kaku, and many more.

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