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Book Projects Arc (2021 → 2023 → 2024+)

The evolution of Jason's book concepts across five years — three distinct pitches, one published book, and two shelved manuscripts whose ideas live on in coaching, newsletters, and yet-to-be-written future work. This page is the master index of Jason-as-author, showing how his thinking has narrowed from universal resilience to founder-specific pivots, and what that narrowing cost and gained.

The Arc in One Paragraph

2021: Resilience Rules, a pan-adult book on adapting to adverse change, grounded in Eastern philosophy + social science. 2023: A three-way decision with book coach Rachel Jepsen between Memoir, Pivot, and Founders in Transition — Jason chose Pivot. 2024: The Path to Pivot (written, published). Currently dormant: the Memoir and Founders in Transition material, plus Resilience Rules as a whole. 2026 hint: a nascent "Wide Ambition" concept emerging from interview prep with Tony Stubblebine.

Phase 1 (2021): Resilience Rules

Full treatment in resilience-rules-archive. The short version:

  • Scope: Universal (any person, any adverse change)
  • Framework: 4 skills × 3 chapters = 12 chapters (Respond, Restore, Reflect, Rebuild)
  • Voice: Philosophical, multidisciplinary, cross-cultural
  • Audience: Knowledge workers + leaders + parents + educators + athletic departments
  • Comps: Switch, Option B, The Obstacle Is the Way, Transitions, The Upside of Stress
  • Status: Proposal complete, never sold, shelved

This was Jason's most philosophical book attempt. It used Eastern philosophy (Buddhism, Daoism, Confucianism, Japanese aesthetics) as structural spine. It was ambitious: to write the canonical resilience book for ordinary people.

Phase 2 (2023): The Three-Way Decision

In early 2023, Jason worked with editor/book coach Rachel Jepsen to evaluate three distinct book concepts. The planning doc (raw/gdrive-writing-projects/jasons-book-planning-doc-2023.md) lays out the comparison:

Option A — Memoir

  • Core question: Is it too late to try something different? Can I still be a big success if I haven't succeeded in prior endeavors?
  • Scenes Jason knew he'd include: Meta layoffs, meeting surrogate, baby's heartbeat/birth, leaving Facebook, 7-day meditation retreat, client stories (Kevin, Charley, Edmar)
  • Voice aspiration: Lyrical, story-driven (vs. his usual tactical style — an explicit craft stretch)
  • Why now: Challenge himself. Become a "real" writer.
  • Target outcome: Mainstream publisher, bestseller status
  • Audience: Family, memoir readers, Asian American readers, creative people

Option B — Pivot

  • Core question: How do you know if you should pivot? How long does it take? What makes it successful?
  • Content: Ridejoy pivot, Headlight pivot, famous pivots (Slack, Discord, Twitch, etc.)
  • Voice: Authoritative, peer-to-peer, actionable
  • Why now: "No definitive book on this." Could be to tech what The Mom Test, Venture Deals, Founders at Work are.
  • Target outcome: Canonical Silicon Valley reference
  • Audience: Founders, investors, startup execs

Option C — Founders in Transition

  • Core question: I left my company, now what? Who am I if not a founder of X?
  • Content: Client stories, exit journeys, sabbatical reflections
  • Structure: Ending → Messy Middle → Beginning (elegant, understudied)
  • Voice: Memoir-advice hybrid
  • Why now: When you exit, no footholds; wandering, exploring; therapists and family don't understand
  • Target outcome: "Classic beyond Silicon Valley" — reach creative/entrepreneurial people broadly
  • Audience: Post-exit founders, artists, anyone facing identity-after-achievement

Rachel Jepsen's Framing Questions

Rachel structured the decision-making around a standard book-coach diagnostic:

  • What am I writing about? / What question does my book answer?
  • Why am I writing this? / Why am I writing this now?
  • Why is my book important? / Who is it important to?
  • What scenes/stories do you already know you'll include?
  • What feeling do you want readers to have? / What qualities should the narrator have?
  • What's the driving force (personal transformation, unpacking complexity, revealing mystery)?
  • What structure works (chronological, starting-at-end, step-by-step, complexity-layering)?
  • Where's the climax? The ending?

This is a reusable framework for anyone evaluating a book idea — Jason has since applied versions of it in coaching clients who are considering writing.

The Decision: Pivot

Jason chose Option B. The planning doc doesn't explicitly announce the decision but the evidence is clear: The Path to Pivot exists; Founder Memoir and Founders in Transition do not.

Why Pivot won:

  1. Market size + specificity. Pivot reaches all founders (broad); Founders in Transition reaches only exiting ones (narrow). Memoir was niche by definition.
  2. Coaching synergy. Pivot could be written and practiced simultaneously — every coaching client working on a pivot became live case study material.
  3. Canonical positioning. Jason explicitly targeted "the next Mom Test / Venture Deals." Memoir and Founders in Transition didn't have equivalent reference points.
  4. Execution readiness. Pivot had clear structure (case studies + frameworks); Memoir required lyrical prose mastery Jason was still developing.
  5. Time-to-market. Pivot was most directly executable with existing material.

Phase 3 (2024): The Path to Pivot Written

Jason completed The Path to Pivot. The book's material lives in startup-pivots, narrowing-as-strategy, and zombie-startups-and-failure. Core structure inferred from chapter draft fragments (raw/ Chapter 8: Narrow Down; Chapter Recaps - Revised):

  • Introduction: What happens when you lose conviction as a founder
  • Chapter 1: Shoot The Zombie — Diagnosing the zombie startup condition, Morrill's Referly → Mattermark
  • Further chapters — The Pivot Pilot approach, case studies (Slack, Discord, Twitch, GOAT, Lyft, IBM, HP), and frameworks for narrowing down, choosing better customers, and communicating through the transition

The framework itself is now live coaching material, referenced across client engagements (see client-case-studies). Ridejoy, Headlight, and Midgame are personal case studies embedded throughout.

What Didn't Get Written (and the Material That Persists)

From Memoir (Abandoned)

  • Meta layoffs and the personal reckoning that followed
  • Client stories: Kevin Kim's transition to agency founder, Charley, Edmar
  • Amanda Phingbodhipakkiya — wife, fertility journey, meeting the surrogate, the baby's heartbeat
  • Parents' immigrant journey (Anping and Amy) as framing device
  • Caryn, Hamilton, Shruthi — the coaches who shaped Jason's own practice
  • Geographic stories: China → Newton MA → Stanford → Silicon Valley → New York → Brooklyn
  • The lyrical, introspective prose Jason wanted to practice
  • The "bigger than self" question: what does success mean after exiting?

Some of this appears in family-and-personal-history, fatherhood-and-commitment, and coaching-journey. The memoir voice is still undeveloped.

From Founders in Transition (Abandoned)

  • The Ending → Middle → Beginning structure (elegant, underused)
  • Sabbatical as a legitimate transformation tool, not just rest
  • Identity reconstruction after founder exit (who are you without the company?)
  • The 7-day meditation retreat
  • Support systems for founders in the void (therapists, friends, family who don't understand)
  • The opportunity to become "classic beyond Silicon Valley" — literary, broad

Some of this shows up in current coaching work, especially with clients like Brooke Hartley Moy (Infactory wind-down), Nick Confrey (Tome wind-down), and Thomas Scaria (Lore acquisition). See client-case-studies and winddown-and-acquisition-coaching.

Phase 4 (2026 hint): "Wide Ambition"

A new book concept is surfacing in 2026, anchored by interviews with Tony Stubblebine (CEO of Medium). The interview prep doc (raw/gdrive-coaching-docs/tony-stubblebine-interview.md) lays out the thesis:

"Wide Ambition" — a critique of Silicon Valley's preference for tall ambition (80-hour weeks, narrow vertical success, money-first) in favor of wide ambition (multiple life dimensions simultaneously: Medium CEO + 32-mile Manhattan walk + fitter at 47 than at 30 + life upstate with his wife). The thesis in one line: "He's not grinding 80-hour weeks. He's wide, not tall."

Tony is a thesis-proving case study. Jason's move: interview a handful of "wide" people (Tony Stubblebine, others TBD) and extract a working philosophy. The angle Tony provided that Jason found most interesting: the "poor overachiever with real financial fears" gap between ambition and bank account — the kind of detail that breaks the perfect-founder myth open.

This is early. It may not become a book. But it's a live thread.

The Evolution: What Jason-as-Author Has Figured Out

2021 → 2024:

  • From universal → founder-specific
  • From philosophical → practical
  • From cross-cultural scaffolding → American-Silicon-Valley idiom
  • From multi-modal brand plans (video, quiz, manifesto) → text-first with newsletter amplification

2024 → 2026 (forecasted):

  • Potentially from single-founder frame → multiple-lives-per-person frame (Wide Ambition)
  • Possibly from startup-specific → broader creative and professional class

What's stable across all phases:

  • Primacy of story and case study over abstract theory
  • Multiple perspectives on the same pattern
  • Research citation is light — one named researcher per idea, not a stack
  • A consistent writer's voice: specific anecdote → principle → reversal → takeaway
  • Respect for the reader as a peer

See jason-voice-and-style for the craft signatures that run through everything.

Why This Page Exists

Books are artifacts. Book projects are intellectual habitats. Keeping the abandoned habitats on record matters because:

  1. Coaching draws on all of them. The Resilience Rules framework, the Memoir material, the Founders in Transition structure — all of it shows up in live client sessions. The books are the slow version; the coaching is the fast version.

  2. Future books may recombine the parts. The Wide Ambition concept is already doing this implicitly — it could borrow the structural elegance of Founders in Transition, the personal voice Memoir was meant to develop, and the actionable framework style from Pivot.

  3. The arc is evidence of judgment. Jason narrowed his focus deliberately and strategically. Seeing the map of what he chose not to do is part of understanding his craft decisions.

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