Reading Seasons

I’ve noticed my reading follows natural seasons—not just calendar seasons, but curiosity seasons. Sometimes I’m in a building mood, sometimes I need perspective, sometimes I just want to understand how things work.

Here’s my reading list organized by the season I’m in and where I’m headed next.

Current Season: Foundation Building

Dec 2025 - Feb 2026

The vibe: Strengthening core skills and mindsets that compound over time.

Currently Reading

  • The Power of Now by Eckhart Tolle
    Why now: Balancing my future-focused planning with present-moment effectiveness

Next in Season

  • Thinking, Fast and Slow by Daniel Kahneman
    Foundation: Better decision-making frameworks
  • Digital Minimalism by Cal Newport
    Foundation: Protecting deep work and focus

Season Theme: Building systems that serve me long-term

Next Season: Execution & Building

Mar 2025 - May 2026

The vibe: Time to ship, create, and apply what I’ve learned.

Planned Reading

  • The Hard Thing About Hard Things by Ben Horowitz
  • The Mom Test by Rob Fitzpatrick
  • Shape Up by Ryan Singer (Basecamp)
  • Atomic Habits by James Clear
  • Deep Work by Cal Newport
  • The 7 Habits of Highly Effective People by Stephen Covey
  • The Marshmallow Test by Walter Mischel

Season Theme: Turning ideas into reality

Future Seasons in Queue

Deep Dive Season (Summer 2026)

Focus: Go deep on 2-3 complex topics rather than breadth

  • Gödel, Escher, Bach by Douglas Hofstadter
  • Sapiens by Yuval Noah Harari
  • The Righteous Mind by Jonathan Haidt

Story Season (Fall 2026)

Focus: Fiction and narrative to feed creativity

  • Project Hail Mary by Andy Weir
  • The Name of the Wind by Patrick Rothfuss
  • Klara and the Sun by Kazuo Ishiguro

Reflection Season (Winter 2026)

Focus: Philosophy and looking inward

  • Letters from a Stoic by Seneca
  • Man’s Search for Meaning by Viktor Frankl
  • The Tao of Physics by Fritjof Capra

Reading Weather Patterns

When I Reach for Different Types of Books:

Rainy Day Reads (When energy is low)

  • Biographies and memoirs
  • Essays and short collections
  • Re-reading favorites

High Energy Reads (When I’m motivated)

  • Dense business/psychology books
  • Technical skill-building
  • Challenging non-fiction

Evening Wind-Down (Before bed)

  • Fiction and narratives
  • Philosophy and reflection
  • Poetry and short pieces

Lightning Round (Quick insights needed)

  • Blog posts and articles
  • Book summaries and reviews
  • Podcasts about books

Seasonal Transitions

How I Know It’s Time to Change Seasons:

From Foundation → Execution:

  • When I catch myself over-researching instead of doing
  • When I have more insights than implementations
  • When I start feeling restless about taking action

From Execution → Deep Dive:

  • When I’m shipping but losing depth
  • When I need fresh perspectives on old problems
  • When I crave intellectual challenge

From Deep Dive → Story:

  • When my brain feels saturated with concepts
  • When I need to feed creativity and imagination
  • When I want to see ideas through different lenses

From Story → Reflection:

  • When I need to process and integrate experiences
  • When I’m feeling overwhelmed by input
  • When big life questions are surfacing

Reading Season Goals

Current Season (Foundation Building) Success Metrics:

  • Establish morning reading routine (15+ min daily)
  • Complete 2-3 foundational books fully
  • Write actionable notes for each book
  • Implement at least 1 concept from each book

Cross-Season Intentions:

  • Variety: Balance heavy non-fiction with lighter reads
  • Application: Try concepts before moving to the next book
  • Connection: Look for threads between different season’s books
  • Documentation: Track what works and what doesn’t

The Reading Cycle

Foundation Building → Execution & Building → Deep Dive → Story → Reflection
        ↑                                                            ↓
        ←←←←←←←←←← Back to Foundation (with new perspective) ←←←←←←←←←←

Key insight: Each season informs the next. The stories I read influence how I build. The building experiences shape what foundations I need. The cycle spirals upward.

Season Notes

Current Season Discoveries:

  • Morning reading (6-7 AM) works better than evening
  • Taking notes by hand increases retention
  • Discussing books with others doubles the value

Next Season Experiments:

  • Try audio books for execution/building phase
  • Schedule implementation breaks between books
  • Find an accountability partner for this season

What season is your reading in right now? I’d love to hear about the natural rhythms you’ve discovered in your own learning journey.

Last updated: December 24, 2025