The Curious Engineer

All blogs / Essays / personal

Jason Shen

jasonshen.com

I help YC founders repair their partnerships and win the inner game so they can build generational companies with people they trust.

Essays / personalEngineering management / careers

’10’15’20’25
Posts
412 from 27 Jun 2009 to 3 Sep 2026
Posting
monthly (12 in the last year)
Kind
personal blog
Feed
https://www.jasonshen.com/rss/

2026 8

  1. The Billion-Dollar Question (Simone Stolzoff)
  2. Self-Comparison is a Waste of Time
  3. Tinder's Founder Conflict
  4. Forty Lessons at Forty
  5. 287: Silent failures are deadly
  6. 286: Expertise is a river
  7. 285: The world needs difficult people
  8. 284: No Objective Truth

2025 34

  1. 283: Control is sublinear
  2. 282: There is no best choice
  3. 281: Rest as hard as you work
  4. 280: Optionality Is a Trap
  5. 279: Confidence as the progressive overload of risk
  6. 278: The Conformity Trap
  7. 277: Go to More Parties
  8. 276: Don't Be a Hungry Ghost
  9. 275: Winner's Mindset
  10. 274: From Zero to Unicorn
  11. 273: Take Pride [Book Notes]
  12. 272: Evaluating Judgment
  13. 271: Manhood & Fatherhood
  14. 270: Make the Case
  15. 269: The New Thirty (From Full to None)
  16. 268: Validation is a Relationship Superskill
  17. 267: Snake Oil
  18. 266: Making a Real Difference
  19. 265: What's the Point?
  20. 264: Signaling Quality
  21. 263: The Tyranny of Thirty
  22. 262: Diminishing Returns on Merit Badges
  23. 261: Making Gut Calls
  24. 260: Fraught Conversations
  25. 259: Off Track at 30
  26. 258: Manager Initiative [Ask Jason]
  27. 257: Threshold Checkpoint Goalsetting
  28. 256: I'm Your Daddy
  29. 255: The Dizziness of Freedom
  30. 235: A Brief Interlude
  31. Pre-Fatherhood 🎬
  32. 234: How to Reset
  33. 233: Analogies are OP
  34. 232: Why Founder Mode Works

2024 48

  1. 231: The Early-Stage Crucible
  2. 230: Choosing Better Customers
  3. 229: Lessons & Anti-Lessons from Gymnastics
  4. 228: Building 10x Better
  5. 227: The History in Our Habits
  6. 226: Write It Out
  7. 225: What Should We Talk About?
  8. 224: Uncovering Your Patterns
  9. 223: Book Advice
  10. 222: Treading Water
  11. 221: Best Practice
  12. 220: Productivity Judo
  13. 219: Long Term Conviction & Short Term Confidence
  14. 218: How to Conference Better
  15. 217: Read This Before You Hire an Executive / Founder Coach
  16. 216: Learning to Speak Naturally
  17. 215: "You Have to Be a Little Delusional"
  18. 214: A Weirdly Brilliant FAQ
  19. 213: Two tech interviews that are four decades apart
  20. 212: Writing a book in 30 days
  21. 211: "Good writing is the Grammarly fixes you ignore"
  22. 210: How come some longtime couples get divorced when they’re old?
  23. 209: Your Talents Will Not Be Appreciated By Everyone
  24. 208: There is no penalty for asking
  25. 207: "Your body language reflects your mental state"
  26. 206: Babe wake up I got a text from the founder of Product Hunt
  27. 205: A smarter way to make friends in a new city
  28. 204: A simple way to jumpstart your creative process
  29. 203: Why are most people so stubborn about certain ideas?
  30. 202: What Great Investors and Successful Outliers Share
  31. 201: One of the most popular tv shows of all-time was nearly cancelled
  32. 200: Resilience → Outliers
  33. 199: Why Books Still Matter
  34. 198: Improvising is OP
  35. 197: Two Pivots
  36. 196: Chosen Suffering
  37. 195: I Wrote a Book
  38. 194: On PG's Essays
  39. 193: What Happens in Coaching?
  40. 192: Getting to Exec (Mind Map)
  41. 191: Hiring Reality Check
  42. 190: How to Do Great Work
  43. 189: Deadlines are Magic
  44. 188: Join the Club
  45. 187: My Kind of Eggs
  46. 186: The Outlier Interview
  47. 185: Personal Bios
  48. 184: No Difference, No Distinction

2023 33

  1. 183: Face Plants
  2. 182: Kryptonite
  3. 181: Strong Suit
  4. 180: Antidiscipline
  5. 179: Being an Outlier
  6. 178: Getting the Whole Story
  7. 177: Contagious Beliefs
  8. 176: No Complaining
  9. 175: Rebuilding a Computer Lab
  10. 174: Give the Money Back
  11. 173: Take the (incremental) W
  12. What is the most underrated management skill?
  13. 172: Professional Courage
  14. 171: Good Conversation
  15. 171: Good Conversation
  16. 170: No Guarantees
  17. 170: No Guarantees
  18. 169: 📦 From Warehouse Associate → OpenAI
  19. 168: 🔮 Don't Be a Glass Cannon
  20. 167: 🧘🏻‍♂️ Modest Insights
  21. 166: 🎡 Building a Flywheel
  22. 165: 🛫 Taking the Leap
  23. 164: Physical Courage
  24. 163: High Intensity
  25. 162: I See You [On Better Meetings]
  26. 161: Showing Up
  27. 160: A Mindfulness Grab Bag
  28. 159: Sitting in Silence
  29. 153: Timeless Wisdom
  30. The Psychology of Money: Timeless Lessons On Wealth, Greed, and Happiness
  31. Dark Horse: Achieving Success through the Pursuit of Fulfillment
  32. 140: Process > Outcome
  33. 135: A Self-Paced Annual Review

2022 8

  1. 131: How to Be Human in the Age of Generative AI
  2. 127: 3 Times I F*cked Up
  3. 125: The Double Loop Pivot
  4. 120: Burned Out Tech CEO → Warehouse Associate
  5. 118: Creative Output
  6. 109: Cut & Run
  7. 104: Turning 36
  8. 102: How to Facilitate a Great Workshop

2021 18

  1. 083—What's one thing you're proud of doing this year?
  2. 082—Why does software change so fast?
  3. 081: Sources of meaning
  4. The Impact of "Traditional Masculinity" on Physical and Mental Health
  5. 079: The Story of How I Switched to Ghost
  6. 078: Why Does Tech Seem to Burn People Out So Quickly?
  7. 076: How an Ex-Stanford Dean Learned to Embrace Her Child's Struggle
  8. 075: How to Ask for Help (According to Science)
  9. Deep Survival: Who Lives, Who Dies, and Why
  10. 066: How Masculine Ideals Affect Resilience
  11. The response to Simone Biles’ exit shows we still have a long way to go on mental health
  12. 060: Brett Kavanaugh's Resilience (Or Lack Thereof)
  13. 053: The Document Arms Race Intensifies
  14. 050: One Year In
  15. 49: Finding Your Edge
  16. 047: The Wisdom of Deb Liu
  17. 044: 🖼 With Softness and Power
  18. 042: 🧠 How Near Misses and Failures Lead to Success

2020 5

  1. MC#032: Keep the Flame Alive
  2. MC#020: The Sweat Edition
  3. Welcome to Making Connections
  4. Finding Your Edge
  5. Solve for the Harder Problem [Interview with Bilal Mahmood]

2016 2

  1. Getting Turned Down By Google Helped Me Get Hired At Etsy
  2. Play to Your Strengths

2015 4

  1. The 10x Job Application
  2. Until You Ship, Communication Is the Deliverable
  3. The Extraordinary Power of Self-Reflection
  4. The Success Equation, Untangling Skill and Luck in Business, Sports, and Investing.

2013 2

  1. Why Practice Actually Makes Perfect
  2. Using Variable Rewards to Drive Behavior Change

2012 1

  1. Good Strategy / Bad Strategy: The Difference and Why it Matters

2009 1

  1. College Summit

Undated 248

  1. https://www.jasonshen.com/077/
  2. https://www.jasonshen.com/072/
  3. https://www.jasonshen.com/071/
  4. https://www.jasonshen.com/073/
  5. https://www.jasonshen.com/074/
  6. https://www.jasonshen.com/070/
  7. https://www.jasonshen.com/069/
  8. https://www.jasonshen.com/063/
  9. https://www.jasonshen.com/158/
  10. https://www.jasonshen.com/157/
  11. https://www.jasonshen.com/156/
  12. https://www.jasonshen.com/155/
  13. 2010 the rejection therapy challenge final review
  14. So you want to try doing rejection therapy eh heres my advice
  15. 2010 the rejection therapy challenge week 2
  16. 2010 the rejection therapy challenge week 1
  17. https://www.jasonshen.com/154/
  18. https://www.jasonshen.com/152/
  19. https://www.jasonshen.com/151/
  20. 2023 readership survey
  21. https://www.jasonshen.com/100/
  22. Workshop facilitation
  23. Give get icebreaker
  24. https://www.jasonshen.com/150/
  25. https://www.jasonshen.com/149/
  26. https://www.jasonshen.com/148/
  27. https://www.jasonshen.com/146/
  28. https://www.jasonshen.com/147/
  29. https://www.jasonshen.com/145/
  30. https://www.jasonshen.com/144/
  31. https://www.jasonshen.com/143/
  32. https://www.jasonshen.com/095/
  33. https://www.jasonshen.com/142/
  34. https://www.jasonshen.com/141/
  35. https://www.jasonshen.com/139/
  36. Upstream
  37. https://www.jasonshen.com/138/
  38. https://www.jasonshen.com/136/
  39. https://www.jasonshen.com/137/
  40. Sf vs nyc
  41. First keynote speech
  42. https://www.jasonshen.com/134/
  43. https://www.jasonshen.com/129/
  44. https://www.jasonshen.com/128/
  45. https://www.jasonshen.com/124/
  46. https://www.jasonshen.com/122/
  47. https://www.jasonshen.com/121/
  48. https://www.jasonshen.com/119/
  49. https://www.jasonshen.com/116/
  50. https://www.jasonshen.com/115/
  51. https://www.jasonshen.com/114/
  52. https://www.jasonshen.com/113/
  53. https://www.jasonshen.com/112/
  54. https://www.jasonshen.com/111/
  55. https://www.jasonshen.com/110/
  56. https://www.jasonshen.com/108/
  57. https://www.jasonshen.com/107/
  58. https://www.jasonshen.com/103/
  59. https://www.jasonshen.com/096/
  60. https://www.jasonshen.com/133/
  61. https://www.jasonshen.com/132/
  62. https://www.jasonshen.com/130/
  63. Goodbye etsy hello world
  64. https://www.jasonshen.com/126/
  65. Mc011 the gymnastics edition
  66. https://www.jasonshen.com/123/
  67. A new adventure working at the smithsonian as a presidential innovation fellow
  68. 2012 how coffee meetings power silicon valley
  69. 2013 becoming a free agent
  70. 2011 blogging luck surface area
  71. How a potluck brunch led to my new job at percolate
  72. You had one job
  73. https://www.jasonshen.com/117/
  74. Blew out knee win national championship
  75. https://www.jasonshen.com/35/
  76. Resilience isnt who you are its what you do
  77. How to become more adaptable
  78. Range why generalists triumph
  79. My op ed in vox
  80. Long hours are bs
  81. https://www.jasonshen.com/106/
  82. https://www.jasonshen.com/105/
  83. https://www.jasonshen.com/101/
  84. 048 the dangers of returning from
  85. 045 bill gs masterclass on framing
  86. 043 dashboard envy
  87. 041 maya most advanced yet acceptable
  88. 040 the fortress tim built
  89. 039 the story of sidras startup
  90. 038 the big trouble trifecta
  91. 037 technologys side effects
  92. Mc036 raise this wounded world
  93. 035 how the pandemic hurt restaurants
  94. Mc033 the social science theory that
  95. 031 winning teams
  96. 030 planning theory vs practice
  97. Mc028 escaping short term thinking
  98. Mc027 counting
  99. Mc026 its a fine line
  100. Mc025 reorgs
  101. Mc023 effort vs impact
  102. Mc21 the three skills of resilience
  103. Mc019 the mindfulness edition
  104. Mc018 and this is my masterclass
  105. Mc017 tradeoffs
  106. Mc016 fidelity vs functionality
  107. Mc015 brains are weird
  108. Mc014 our spreadsheet overlords
  109. Mc013 breaking rules breaking stereotypes
  110. Mc012 the humor edition
  111. Mc008 not so secret memo
  112. Mc005 protest edition
  113. https://www.jasonshen.com/099/
  114. https://www.jasonshen.com/098/
  115. https://www.jasonshen.com/097/
  116. https://www.jasonshen.com/094/
  117. https://www.jasonshen.com/093/
  118. https://www.jasonshen.com/092/
  119. 058 sometimes you gotta punch back
  120. The fuzzy and the techie
  121. Remote
  122. The year without pants
  123. https://www.jasonshen.com/091/
  124. The advantage
  125. https://www.jasonshen.com/090/
  126. https://www.jasonshen.com/089/
  127. https://www.jasonshen.com/088/
  128. https://www.jasonshen.com/087/
  129. https://www.jasonshen.com/086/
  130. https://www.jasonshen.com/085/
  131. https://www.jasonshen.com/084/
  132. Switching to ghost
  133. Five five
  134. No silver bullets
  135. 067 how not to die in the wild
  136. 068 how music gets you in the zone
  137. How to give your product personality
  138. How to be relentlessly resourceful
  139. A request and giveaway for my twenty sixth birthday 2
  140. https://www.jasonshen.com/26/
  141. Listen to everyone then make up your own mind
  142. Earning co founder trust
  143. Crafting the ridejoy mobile app a ux design case study for startups
  144. Why learning to code is important
  145. Learning to code with treehouse
  146. Theres nothing to complain about
  147. Hartls ruby on rails tutorial
  148. https://www.jasonshen.com/27/
  149. Sarah allens little rules for working life
  150. Training to dunk
  151. 17 essential best practices for making things happen
  152. One womans incredible startup journey in peru
  153. Training makes it possible
  154. The minimum viable transaction
  155. https://www.jasonshen.com/28/
  156. Three days with magic
  157. https://www.jasonshen.com/29/
  158. Goodbye percolate hello etsy
  159. Six blistering bodyweight workouts you can do in under 30 mins
  160. First impressions etsy
  161. The rise and fall of product lines
  162. The biggest challenge with building products is uncertainty
  163. Learning from volkswagen
  164. Readership survey
  165. What makes effective problem solving teams
  166. The new napster how sci hub is blowing up the academic publishing industry
  167. https://www.jasonshen.com/30/
  168. Beyond the 10000 hour rule
  169. What the black lives matter movement means to me
  170. Product insights from pokemon go
  171. An open letter to managers of women
  172. Ridejoy lessons learned
  173. https://www.jasonshen.com/31/
  174. https://www.jasonshen.com/32/
  175. How to facilitate with piper anderson
  176. Starting over
  177. Lessons on persistence from dean karnazes
  178. Conflict isnt always bad
  179. Techstars alexa
  180. Burnout recharging for batteries not people
  181. Captains log
  182. Whats going to change
  183. Prolific than perfect
  184. Adaptability is no joke
  185. Gymnastics lessons performing under pressure
  186. My experience with toastmasters
  187. Introducing headlight
  188. The difference between a prototype and a demo
  189. Office perk
  190. Midgames next chapter
  191. Why being real matters
  192. Startups as chemical reactions
  193. Lean in
  194. Eleven compelling startup pitch archetypes
  195. The dip
  196. Dont call it that
  197. Zero to one
  198. The little book of talent
  199. How google works
  200. Great by choice
  201. Tribe junger
  202. The inevitable
  203. The alliance
  204. Elements of content strategy
  205. Make sense of any mess
  206. Smart choices
  207. What we should learn from the away scandal
  208. https://www.jasonshen.com/33/
  209. Community is friendship
  210. On protests and movements
  211. The product genius behind jackbox games
  212. What i learned from my first blunder filled marathon
  213. Two feelings you need before starting a startup
  214. Getting your groove back
  215. Taking cold showers
  216. Value of ongoing conversations
  217. How tech workers are finding their footing in a pandemic
  218. Product design for the web randy hunt
  219. 26 3
  220. Gymnastics lessons overcoming fear
  221. Gymnastics lessons skill acquisition
  222. A request and giveaway for my twenty sixth birthday
  223. 065 massive aspirational and public
  224. 064 the lost art of speaking to strangers
  225. 062 drivers of asian hate
  226. 061 a healthy breakdown of order
  227. 059 mapping the impact of change
  228. 057 good advice from kevin kelly
  229. 056 a structure to present strategy
  230. 055 the resilience rules framework
  231. 54 lessons learned at 35
  232. 052 we should copy more
  233. 051 every knowledge worker should
  234. 046 what was your internet like
  235. Mc034 leadership in turbulent times
  236. 029 personal best
  237. Mc024 a taxonomy of visual diagrams
  238. Mc022 the docs edition
  239. Mc010 seeking a benign violator
  240. Mc009 decade of insights
  241. Mc007 the infant mindset
  242. My pandemic burnout piece in fast
  243. Mc006 the exponential
  244. Making connections 003 what opportunity
  245. Making connections 003 biological
  246. Making connections 002 purpose iteration
  247. Making connections 001
  248. Making connections 001 audio