The Endgame of the Self

If you write for long enough you will eventually realize that committing plans to a page grants them a strange power. Whether this is truly mystical or just a psychological tool for honing intent, I’m unsure. But from a utilitarian standpoint, it doesn’t matter why it works–it just does.

That’s why I keep what I call “The Ledger,” usually a handsome leather-bound journal in which each day is granted a single page. At the front of The Ledger I’ve specified my ideal daily routine. I then check each day against this ideal to make sure I’m at least getting close, if not following it to the letter. At the back, I’ve listed what goals could theoretically be achieved if I continued the routine and adhered to The Ledger throughout my lifetime.

Thanks to the laws of compound interest (which applies to far more than just finance), the holistic result is pretty daunting. It describes a me that is a stranger, in many ways, to the current me. This future self is a near-Herculean specimen, not just a guy in OK shape. He’d be pretty comfortable in a post-apocalyptic setting, what with those bowhunting and martial arts skills, all why maintaining the composure of Yoda because he’s a meditation master and has shed almost all material attachments. In a stable world he works a lot of hours but not primarily for money, because through investments he’s learned how to earn while he sleeps. He’s less of the introvert that he used to be and more of an omnivert, in that he maintains close connections with the art and tech worlds where he has a “discrete, behind-the-scenes specialist” reputation. He does much of this work remotely, while seeking the authentic experience of various locales. If he’s known to the public at all, it’s for being that guy who publishes way too many books in way too many different genres. But for the most part, he’s an elusive ghost flitting between airports.

Partly to further empower The Ledger by making it public, and partly to provide a template for how others might approach mapping their “Endgame of the Self,” I’m including the crucial front and back of my Ledger below. A part of me blushes to do so, because I am (as the lack of strike-throughs will show) decades & orders of magnitude in mental toughness away from accomplishing all of this. But I honestly believe it is all do-able in this lifetime–probably by or before the age of 50 (I’m 25 now). Factoring in Murphy’s Law, maybe a couple won’t get the coveted strike-through–but I aim to take as many of these scalps as possible, or go down trying. I’ll also repost this list at least once a year to update the strike-throughs and stay accountable.

(Sorry if the formatting’s wonky–it looks better in a Word doc).


The Routine

On weekdays—

In the mornings,

  • Cold Shower
  • Exercise (Push, Crunch, KB Swing, KB Curl, KB Press, KB Squat, Bench, Dead, Overhead), M-W-F


  • Meditate, T-Th


During the day,

  • Earn $ for food/clothes, shelter/transportation, savings/investments


  • Study on a scholarship/stipend


In the evenings,

  • Read books/take online courses


  • Write


On weekends—

  • reenact my weekday evening routine


  • relax with family/gaming


The Diet


  • D3
  • Natural T AM
  • B12
  • 48 oz water
  • Whey protein & milk
  • Tea or coffee if necessary
  • Metrx bar(s) or eggs
  • Avocado(s)


  • 48 oz Water x2
  • 10-25 oz chicken or beef
  • Mixed vegetables & greens
  • Chili if necessary
  • Peanut butter sandwich if necessary
  • Natural T PM capsule
  • Homemade dessert once every other week

Big Picture:


220-240 lbs

10-15% Body fat


Goals Met via the Routine


  • 50 Pushup Set
  • 100 Pushup Set
  • 150 lbs Benchpress & 200 lbs Deadlift
  • ½ hr meditation
  • 1hr meditation
  • Black Belt


  • Emergency Fund
  • IRA
  • Mutual/ETF funds
  • Cryptos
  • Vehicle paid off
  • Reach maximal minimalism*
  • Experience India & China
  • Experience UK & Russia
  • Experience Grecorome
  • Experience Israel & Egypt
  • Experience Thailand & Japan


  • Undergrad
  • Master’s or JD
  • Competent coder
  • Competent cook/baker
  • Competent gardener
  • Competent archer


  • Compilations
  • Editor
  • Poetry**
  • Novel(s)
  • Copywrite
  • Research/Report
  • Lyrics on album
  • Story as film/game
  • Teacher/Professor
  • Pulitzer/Nobel/MacArthur/Honorary Degree, Etc
  • Code original software
  • Entrepreneur

*to own nothing but my kettlebells, pot&pan, toolbox, suitcase (clothes), backpack (books & laptop), couple pairs of shoes/boots, & possibly a vehicle if indispensable.

**this one’s strikethrough is pending.

2 thoughts on “The Endgame of the Self

  1. You go, Son, you go!! ☺

    From: Christopher Lee Winn Reply-To: Christopher Lee Winn Date: Friday, October 12, 2018 at 8:45 PM To: Subject: [New post] The Endgame of the Self

    clwblog posted: “If you write for long enough you will eventually realize that committing plans to a page grants them a strange power. Whether this is truly mystical or just a psychological tool for honing intent, I’m unsure. But from a utilitarian standpoint, it doesn’t “


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