Key Moments

Full Length Episode | #182 | March 17, 2022 | Deep Questions Podcast with Cal Newport

Deep Questions with Cal NewportDeep Questions with Cal Newport
People & Blogs4 min read62 min video
Mar 17, 2022|1,484 views|30|2
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TL;DR

Cal Newport discusses writing, productivity, business models, and overcoming procrastination.

Key Insights

1

Proposal writing is disliked by many authors due to its lack of craft and signaling nature.

2

Adopting a slow productivity method, like John McPhee's 500 words a day, can lead to significant long-term output.

3

Cal Newport's business model operates on a flywheel: strong book sales lead to a richer life, which fuels an engaging online platform, which in turn boosts book sales.

4

Effective training involves identifying and resolving points of confusion during the learning process.

5

Deep procrastination arises from a combination of extrinsic motivation and excessive cognitive toil, and can be overcome by shifting to intrinsic motivation and reducing workload.

6

Improving non-technical writing skills involves dissecting admired authors' styles and practicing emulation, ideally with editorial feedback.

THE GRUELING REALITY OF WRITING PROPOSALS

Cal Newport begins by expressing his relief in shifting from writing book proposals to working on a New Yorker article. He explains that proposal writing is generally disliked by authors because it lacks the craft and narrative engagement found in other forms of writing. Instead, it resembles a business plan, focusing on information delivery rather than stylistic flair. The often speculative and "signaling" nature of proposals, where authors discuss potential outcomes and marketing strategies, can also feel hollow and frustrating. This mechanistic and signaling-heavy process is a stark contrast to the creative and structural challenges of crafting compelling articles.

EMBRACING THE MCÍFEE METHOD FOR SUSTAINABLE PRODUCTIVITY

Newport contrasts his own writing process with that of author John McPhee, who, despite immense success, rarely writes more than 500 words a day. This 'slow productivity' approach, where consistent small efforts accumulate into significant output over time, is highlighted as a more sustainable model than the high-volume output of writers like Brandon Sanderson. Newport is considering adopting McPhee's method for his own work, particularly as he anticipates a period of dedicated book writing. He emphasizes that impact over time does not necessarily stem from busyness or exhaustion but from a focused, consistent practice, embodying the idea that 'if you keep adding an ounce to a bucket, you will eventually have a quart'.

CAL NEWPORT'S FLYWHEEL BUSINESS MODEL

Richard from California inquires about Cal Newport's business model. Newport explains it using Jim Collins' flywheel metaphor, where core book and New Yorker writing fuels a richer, deeper personal life. This enhanced life then makes his online platforms, primarily his email newsletter and podcast, more interesting. The growth of these platforms, in turn, allows his books to achieve greater reach and financial success, further enriching his life and enabling more compelling content. The income generated is primarily valued for the autonomy and flexibility it provides, such as the ability to pay his own salary during summers, rather than for direct financial gain.

STRATEGIES FOR EFFECTIVE TRAINING AND KNOWLEDGE RETENTION

Spencer, a security engineer, asks for advice on tackling an intense week-long security training. Newport recommends against pre-reading syllabus chapters, suggesting instead a 'question resolution method' during the training. He advises attendees to meticulously mark topics they don't fully understand on their printed syllabus or notes. The key is to actively identify knowledge gaps and then promptly seek to fill them through instructor interaction or by consulting the material. This ensures that by the end of the training, all concepts have been understood, providing a solid foundation for future review rather than struggling to learn from scratch.

DECODING AND CONQUERING DEEP PROCRASTINATION

Abhishek inquires about writing non-technical articles and emulating authors like Bill Bellevue. Newport suggests a two-pronged approach: dissecting admired authors' styles to understand their formulas and then practicing emulation. This practice develops stylistic muscles, with the suggestion that it's most effective when done for editing, providing external pressure and feedback. He also fondly recalls the early days of the internet, referencing his previous work on his 'Study Hacks' blog and the value of RSS feeds for curating content from interesting bloggers, a period he sees as a high point for online production before its consolidation into current social media forms.

ADDRESSING DEEP PROCRASTINATION IN STUDENTS AND PROFESSIONALS

Cal Newport addresses deep procrastination, a term he coined to describe students losing their ability to complete academic work. He explains it stems from a combination of extrinsic motivation (high achievement for external validation) and excessive cognitive toil (demanding academic load). For students, the solution lies in shifting to intrinsic motivation by aligning studies with a personal lifestyle vision and reducing the cognitive load through simplification of schedules and majors. For professionals, the principles are similar: reorienting work towards a personal vision and reducing chronic overload by doing less and being more intentional about new tasks, differentiating it from depression which requires clinical attention.

NAVIGATING NEW YEAR'S RESOLUTIONS AND PLANNING

Matt, a wealth advisor, asks about integrating New Year's resolutions with time-blocking and guiding documents. Newport simplifies this by suggesting that annual plans and resolutions can be integrated directly into quarterly plans, visualized as a header. He recommends maintaining a separate values document reviewed weekly. The core strategy remains multi-scale planning: daily time-blocking informed by weekly plans, which are based on quarterly plans. This hierarchical structure ensures that resolutions and overarching goals are consistently considered and acted upon across different planning horizons, making the system more manageable and less fragmented.

Training & Learning Strategies

Practical takeaways from this episode

Do This

Print the syllabus and notes in advance.
Mark topics you don't fully understand with a clear symbol (e.g., '?').
Prioritize filling knowledge gaps immediately after a session by consulting instructors or materials.
For intense training, focus solely on the material: eat well, stay hydrated, get rest, and avoid other demanding cognitive work.
When learning to write, dissect authors you admire and emulate their style.
If possible, practice emulation by writing for editing to receive feedback and improve.
For deep procrastination, reduce extrinsic motivation and cognitive toil.
For professionals, reshape your work life towards an intrinsic, lifestyle-centric vision.
Reduce chronic overload by doing less and practicing a 'pull' rather than 'push' approach to new tasks.
Apply good habits: time blocking, weekly/quarterly planning, and effective to-do systems.
Review your values document weekly.
Integrate annual plans and resolutions into your quarterly planning documents.

Avoid This

Don't over-prepare by reading textbook chapters in advance of a training session unless explicitly required.
Don't aim to learn entirely new material during exam preparation; focus on reviewing what you've already grasped.
Don't assume a difficult course schedule or many extracurriculars will impress future employers; focus on core requirements and manageable loads.
Don't confuse deep procrastination with depression; seek clinical help for depression.
Don't let non-writing activities consume excessive time; constrain their footprint.
Don't treat income as solely a scorecard; view it as a tool for flexibility, remarkability, and a deeper life.

Writer Productivity Comparison

Data extracted from this episode

AuthorDaily Word CountTotal BooksNotable Achievements/Accolades
John McPhee~500 words29Pulitzer Prize, National Book Award nominations
Brandon Sanderson2,000-3,000 wordsMultiple (produces ~2 books/year)Prolific genre author

Common Questions

Cal Newport finds book proposal writing frustrating because it lacks craft, focusing more on business planning and signaling than good writing. The content often feels hollow and bombastic, and it's not the style of writing he enjoys doing.

Topics

Mentioned in this video

People
Tim Ferriss

Mentioned as an example of someone whose content Cal Newport might read while procrastinating, and who is associated with the 'deep procrastination' topic.

Wendell Berry

Mentioned alongside John McPhee as an example of an author who retreats from public life to focus on their work, appealing to a desire for focused creation.

Bill Bellevue

Nature writer whose peaceful and relaxing style is emulated by a listener seeking to improve their non-technical writing.

Strunk and White

Authors of 'The Elements of Style,' mentioned as helpful for technical writing, contrasting with the desire to improve non-technical writing.

John McPhee

Author whose method of writing only 500 words per day Cal Newport finds inspiring and potentially sustainable for his own work.

Brandon Sanderson

Author mentioned as a comparison for high productivity, writing 2,000-3,000 words a day, contrasting with McPhee's 500-word approach.

Neil Stephenson

Author whose strategy of focusing on regular book releases rather than conference appearances is cited as a model.

William Zinsser

Author of 'On Writing Well,' recommended for improving non-technical writing and understanding authorial style.

Leo Babauta

Minimalist blogger from the 'Zen Habits' era, mentioned fondly by Cal Newport as part of the early, high-quality web content.

Cal Newport

Host of the Deep Questions podcast, discussing his writing process, business model, and productivity strategies.

Malcolm Gladwell

Author whose writing style Cal Newport dissected in the past to learn idea-driven non-fiction.

David Remnick

Current editor-in-chief of The New Yorker who also took John McPhee's nonfiction writing class at Princeton.

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