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Thinking Themes

  • Physical, emotional, and mental health
  • Wisdom, knowledge, and information
  • Value chains
  • Becoming a writer
  • Confidence
  • Creating, editing, and ownership
  • Thinking more, talking less and more purposefully
  • Using early morning for creative work instead of task work
  • Companies as primary mechanism by which humans organize to solve problems
  • The oil deposits of knowledge waiting to be refined into gasoline
  • Extrinsic motivations vs. intrinsic motivations
  • Defining "modern work"

End of Year Journal Reflection

I’ve journaled for something like ten years. I average something like 70-120 entries at around 1,000 words an entry. Some directed writing, some stream of consciousness. I write to think in the moment. It’s extraordinarily clarifying to see my thoughts.

One thing I love doing is looking back at what I’ve written on the one, two, three year anniversary of whatever day it is I’m writing. It’s interesting to observe the plurality of the self across time. I’m also a big end-of-year ritual person. I cherish the time around the holidays because I slow down and think deeply about what I’m happy with and what I’d like to change. This year I tried something new with my end-of-year ritual. I decided to go back and read every single journal entry from 2018.

I opened a note as I read and created headings for each month. As I read, I took notes on themes and anything that generally or specifically struck me. I planned on reviewing all the notes at the end in some kind of meta review. After getting through January, I knew this was an awesome decision. I was pretty amazed at how much I forgot. I had some good ideas. I had some wrong ideas. I thought I was doing a good job as CEO in Jan 2018. In December that made me more than chuckle.

The whole exercise took me a week or so of hour long sessions. At the end, I found I consistently write about ~15 themes:

  • Confidence
  • Identity
  • Relationship with my business partner
  • The value of the past
  • The plurality of the self
  • Growth as a leader & CEO
  • My tendency to numb
  • Loneliness
  • New friends
  • "The barely awake"
  • Taking things too seriously
  • Systems for navigating life
  • Health
  • Gratitude
  • The state of the world

Big Events


  • Announced Holloway (Feb. 8, 2018); link
  • R2
  • Released first Holloway product, The Holloway Guide to Equity Compensation (Aug. 8, 2018); link
  • Finished the first full draft of The Holloway Guide to Raising Venture Capital, my first book-length piece of writing.



A new section this year.

  • Working out
  • Reading at lunch
  • Keeping away from alcohol during the week
  • Benchmarking health by resting heart rate



Kevin Kelly

Twitter Wisdom










Live music

  • Nils Frahm
  • The Punch Brothers
  • Nathaniel Rateliff & the Night Sweats
  • Lake Street Dive
  • Russ
  • Marshmello
  • Elizabeth Moen
  • Leon Bridges


Quarterly playlists

Created this year

Discovered this year



  • AutoSleep
  • HeartWatch
  • Waking Up
  • PowerThesarus
  • Dictionary (Webster's)
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