Deep Questions with Cal Newport

Episode 384: What Should I Read for a Deeper New Year?
Date: December 22, 2025
Host: Cal Newport

Episode Overview

In this special holiday episode, Cal Newport shifts the spotlight to listener questions and focuses his opening deep dive on a timely query: What should I read to start 2025 off right? Cal handpicks six influential, non-self-help books from his own shelves that offer profound wisdom for living a deeper, more meaningful life. The episode then opens up the lines to an international audience, offering rapid-fire, practical advice on digital distractions, deep living, creative work, time management, and more—all steeped in Cal’s hallmark blend of pragmatism, philosophical insight, and wry wit.

Main Theme:

How can reading—not just self-help, but deeper, intellectually rich and philosophically provocative books—nourish your pursuit of a deeper life in the New Year?

Key Discussion Points & Insights

1. Six Books for a Deeper New Year

(Cal’s book selections and why each matters)

[05:15] 1. Walden (Henry David Thoreau)

• Misunderstood Classic: Not just nature writing or an argument for leaving civilization, but "one of the first books to tackle the idea of lifestyle centric planning."
  • "Let me try to fix an understanding of what I want my life to be like and then work backwards from that systematically to figure out how I get there." (Cal, 08:25)
• Thoreau’s Experiment: Pinning down the minimum needed for survival, then selectively and consciously adding back “the good stuff.”
• Actionable Wisdom: Run similar experiments in your life—identify what’s truly essential, and build meaning from there.

[14:10] 2. Lincoln’s Virtues (William Lee Miller)

• Moral Biography: Chronicles how Abraham Lincoln developed his moral intelligence through reading, reflection, and actively organizing and debating his thoughts.
  • "You have to develop your moral intuitions into actual moral intelligence if you really want to leave a positive impact on the world. That takes work, but it’s meaningful work and it’s work that needs to be done." (Cal, 16:35)
• Contemporary Resonance: Contrasts Lincoln’s lifelong exercise of thinking hard and organizing ideas with today’s impulsive digital outsourcing of thought.

[19:30] 3. The Case for God (Karen Armstrong)

• Restoring the Transcendent: Explores how modern, Enlightenment-era thinking misframes religion. True engagement with the transcendent requires a “pre-modern mind”—humility before mysteries and ritual-action, not merely assent to empirical claims.
  • “You need a pre-Enlightenment mind to approach religion. And when you do… you realize all the ancient books from the main wisdom traditions see God as ineffable, too complicated for your puny human minds to understand.” (Cal, 22:20)
• Cultural Context: Points to a hunger for transcendence and meaning in our nihilistic, postmodern digital era.

[35:40] 4. You Are Not a Gadget (Jaron Lanier)

• Humanism in Technology: A call to prioritize human flourishing and individuality above the dehumanizing, homogenizing effects of Big Tech and platform capitalism.
  • “What Lanier brought into the discussion of technology was humanism...It’s dehumanizing us… Technology should serve [human flourishing] and if we’re not careful, it will come in and squash that without even thinking about it.” (Cal, 36:40)
• Celebrating Communities: Lanier and Cal both praise the magic of eccentric, homemade forums and communities—contrasted with algorithm-driven feeds.

[42:13] 5. The Shallows (Nicholas Carr)

• Neuroscience of Distraction: First to sound the alarm on how the Internet physiologically rewires our brains, degrading our capacity for sustained thought.
  • “He basically said, look, I don’t know if you’ve noticed this, but I’m having a harder time reading…These new technologies…could rewire your brain in a way that’s permanent.” (Cal, 43:32)
• Legacy: Paved the way for today’s growing concerns about technology, distraction, and diminishing cognitive ability.

[46:51] 6. Falling Upward (Richard Rohr)

• Wisdom for Life's Stages: Rohr, a Franciscan priest, describes life as two great arcs—initial ascent (career/family/achievement), followed by hardship, then a deeper second phase of wisdom, connection, and service.
  • “It’s the hardship that happens, like, as you approach midlife, that you emerge out of, and then you have this second peak that is much more built around deeper wisdom...connection to others, helping others.” (Cal, 47:08)
• Practical Philosophy: Equips listeners with a healthy frame for processing suffering—one sorely lacking in our present culture.

2. Cal’s Quick Tips: Reading for Depth

• Don’t aim to finish all six quickly—pick one that resonates and commit to reading it in the first week of the new year as a gateway to sustained, intentional reading in 2025. (51:30)

Listener Q&A: Calls from Around the World

(All ad segments, sponsor mentions, and intros/outros have been omitted.)

[54:10] Q1: Parenting through Digital Distraction

Henrik from Norway: How do I help my young kids resist screen addiction when their mother and grandparents use iPads as pacifiers? How do we “shame” their mother into joining Team Dad (screen-free)?

• Cal’s answer is compassionate, practical, and tongue-in-cheek (ref. "Shame the bastard into submission").
• Cal’s Parenting Tech Rules:
  • Draw clear boundaries: no smartphones or unrestricted iPads before high school age (or Norwegian equivalent); devices live in the kitchen, not bedrooms.
  • “An iPad is just an inconveniently large iPhone...If they have an iPad, it lives in the kitchen too. It’s completely locked down until they’re 16.” (Cal, 59:44)
  • Hold the parental line; you’re giving your kids an “enormous competitive advantage” in flourishing.
  • Don’t expect to change other adults’ behavior directly in the household.

[01:03:55] Q2: Living Deeply with Multiple Creative Identities

Christian from Arizona: How can I sustain deep creative work across multiple crafts (writing, photography, DJing) when my day job already drains my creative energy?

• Key Advice: Accept the need for slow, steady progress. Pursue “slow productivity”—don’t judge progress by the week, but by the year.
• Use strong context-switch cues between jobs (e.g., exercise, dedicated spaces) and consider backing off day job hours if feasible.
  • “I’m expanding out to what did I do this year, not what did I get done this week... It’s a slow productivity.” (Cal, 1:07:13)

[01:09:27] Q3: Time Blocking for Self-Employed Schedules

Caller: When my inspiration doesn’t match my planned time blocks, should I force myself to stick with the block or switch?

• Cal’s Pragmatic Compromise: Don’t over-plan in advance; make a broad weekly plan, then time-block each day flexibly.
  • “Time block each day as you get there, leave yourself flexibility... if you’ve just made a plan for that day, stick with it.” (Cal, 1:13:40)
• For more flexibility, check Cal’s interview with Oliver Burkeman.

[01:18:32] Q4: Can You Have a Deep Life in a Non-Knowledge Job?

Joe from Jerusalem: How do you pursue the “deep life” if your job isn’t knowledge work but, say, sales or a role demanding constant attention?

• Clarification: The “deep life” is about intentionally designing a life focused on what matters to you.
• Deep work theory is separate: If your job doesn’t involve creating value through focused thinking, don’t worry about context switching.
  • “You can be a believer in the ideas I talk about without feeling like you’re doing something wrong… if you’re in a job that’s communication-based.” (Cal, 1:21:45)
• If part of your job does require deep work (proposals, etc.), carve out focused time.

[01:25:11] Q5: Digital Disintermediation and Overwhelm

Caller: How did we arrive at our current state—everyone, regardless of age, is expected to be their own IT support in an overwhelming digital world? Where are we headed?

• Historical Analysis: In the personal computer era, businesses tried to save on salary costs by firing support staff and offloading all tasks onto remaining employees—ignoring how human brains actually function and the cost of constant context shifts.
  • “The management class focused myopically on salary… They were entirely indifferent to… the attention capital someone has… It was a complete myopic view of productivity.” (Cal, 1:27:54)
• Resulted in inefficiency, lost human flourishing, and left “a lot of economic growth on the table.”

[01:31:54] Q6: Concerns about AI—How to Talk About Real Risks

Caller: How can I bring up valid AI concerns (career loss, skill atrophy, environmental cost) without sounding like a cranky Luddite?

• Cal’s Rule: Stick to evidence-based, real-world impacts—don’t react to sci-fi or hypothetical futures.
  • “Focus on the things that are happening now. There’s so much happening now with AI… Look at short-form video technologies—these are causing harms right now.” (Cal, 1:34:40)
• The “storytelling” around AI (e.g., superintelligence, mass unemployment) can be a smokescreen, distracting from urgent current harms (e.g., real psychological damage, IP theft, energy impact).

[01:39:23] Q7: Starting Deep Work When Distractions Fill the Void

Caller: If someone wants to start deep work but doesn’t know what else to do if they stop their distractions, what’s your advice?

• The “Bigger, Better Offer”: People stick with their distractions because there’s no compelling alternative.
  • “Without that bigger, better offer, people say, I’ll take the devil I know because it’s kind of fun, than the devil I don’t, which is staring into the pit of existential despair.” (Cal, 1:41:10)
• The way out is lifestyle-centric planning: envision what an ideal daily life looks like across all buckets (not just work) and systematically move toward it, bucket by bucket.
  • “Have a vision for your ideal lifestyle—what do you want in each area? Then navigate the obstacles and opportunities you face.” (Cal, 1:44:33)
• As your life grows deeper and richer, the allure of digital distraction fades.

Notable Quotes & Memorable Moments

• On Walden’s true lesson:
  “It is instead, in my opinion, one of the first books to tackle the idea of lifestyle centric planning.”
  (Cal, 08:25)

• On technology and the mind:
  “We’re running away from actually using our brain. Lincoln ran towards using his brain and it made him a moral giant.”
  (Cal, 17:41)

• On modern religion and meaning:
  “You need a pre-Enlightenment mind to approach religion...Through action you get intimations of what is actually true.”
  (Cal, 22:20)

• On social media’s corrosive standardization:
  “He wasn’t talking about [tech] robbing you of data. He was talking about it robbing us of our humanity… Technology should serve [human flourishing].”
  (Cal, 36:40)

• On creative ambition and energy:
  “I’m expanding out to what did I do this year, not what did I get done this week...It’s a slow productivity.”
  (Cal, 1:07:13)

Timestamps for Key Segments

• 00:06 – Intro: Holiday episode mission
• 05:15 – Six books for a deeper New Year (Walden)
• 14:10 – Lincoln’s Virtues
• 19:30 – The Case for God
• 35:40 – You Are Not a Gadget
• 42:13 – The Shallows
• 46:51 – Falling Upward
• 51:30 – Cal’s advice on reading practice
• 54:10 – Parenting against screens
• 01:03:55 – Multimodal creative life
• 01:09:27 – Time block or follow inspiration?
• 01:18:32 – Deep life for non-knowledge workers
• 01:25:11 – Workplace disintermediation
• 01:31:54 – How to talk about real cost of AI
• 01:39:23 – How to get started with deep work

Episode Tone & Language

• Tone: Warm, pragmatic, philosophical, gently humorous.
• Language: Clear, explanatory with moments of scholarly depth, always accessible. Offers empathy and context; avoids shaming or prescriptivism; lightly self-deprecating.

Final Thoughts

This holiday episode serves as both a practical reading guide and a philosophical roadmap for anyone seeking to begin 2025 living more deeply—offering not just book recommendations, but a call to pursue wisdom, intentionality, and meaning in an age of distraction. Through hand-picked book wisdom, practical digital minimalism, and responsive advice for real listener concerns, Cal Newport demonstrates what it means to engineer a “deep life” amidst the noise.