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The Art of the Good Life: 52 Surprising Shortcuts to Happiness, Wealth, and Success

🌱 This post is in the growth phase. It may still be useful as it grows up.

1 Mental Accounting

How to Turn a Loss into a Win

Related post: Chan Spot

2 The Fine Art of Correction

Why We Overestimate Setup


Preparation. Then presence.

I’ve felt this most in my evolution as a conversationalist — I can’t say “podcaster”.

My best conversations are when I prepare in advance. But, in the moment, be perfectly present — not thinking about directing or framing — just being there.

Thoughts with friends

  • ma says that he thinks i’m good at this — actually changing my mind readily when better information is presented
    • he suggestions the notion that small changes can be harder than big changes — changing a destination vs correcting the path
  • em mentions something she heard in a message “long obedience in the same direction”
    • there is no moment of arrival
  • dustin admits the need to adjust feeling like a failure
    • identifies with the books line about “doing away with the stigma around constant correction”
  • dan identifies with a tendency to overvalue upfront costs
    • uses a term a like “when your plans meet other people”, in describing when and why plans often need correction
  • i share about my excitement over learning this balance of “preparation and presence”
    • used as as example of a success on this front — careful upfront planning followed by presence in every episode, willingness to review and correct, and adapt
  • emily identifies the need for “emotional preparation to adapt”
  • ma connects “rabbit holes”, in the language of Shape Up
    • identifying things that will probably go wrong or take to long
  • i share mine and nellie’s “worked/didn’t” framework
  • dan inquiries about when the reversal of this principle. posits that “first impressions” are something that are difficult to course carrect
  • i share that i visualize first impressions creating a moat around a castle. good first ones make that relationship easy to revisit. bad ones can require require heroing effort to overcome
  • dan “and sometimes you storm that castle to find nothing in the treasury”

3 The Pledge

Inflexibility as a Strategem


”Precided” — decided, until proven undecided Decision over choice

If you want to orient toward efficacy, you have to make decisions before you’ve seen all the choices.
If we don’t the choices — once we realize them — will make us useless.

Thoughts with friends

  • ma says he has nothing that is non-negotiable. “I have nothing hard in my life” [snicker]
  • allie is not in a position to be inflexible. grieves the loss of the stage of life where this was a luxury
  • dan feels this is in opposition of with the previous lesson rule on being flexible
  • allie references “things i will never do” concept by Shauna Niequist — “present over perfect”
  • i mention the most important section of my todo list being the “things i’m not doin today” section at the top. it’s a sacrifice on the alter of the things i want to do that day
  • dan mentions how absolute commitment is a good defense against decision fatigue
    • Ego depletion
    • me: trap is the setup overestimation issue
      • dave rams budget as an example of a pledge that has to be regularly corrected
  • i share my stupid metaphore about pipes, wires, and conduit
    • conduit is rigid pipes to guide flexible wire. pledges are the framework that guard and direct unstructured work. they are the pillars. when you re-think them, it means the structures they protect will also be brought into question.
  • dan: “achievement thru repeatedly doing the same thing”
    • warren buffet
  • allie says we falsy equiate rigidity with being brittle. rigid things can still elasticity
    • roller coasters and airplane wings
  • ma asks if it’s necessary to have things that you just absolutely won’t budge on
  • i mention that, beyond our wedding vows, nellie and i have a much more casual agreement “cheat on me and I will dump your ass”
    • if cheating were to ever happen, my i could forgive here but the boundary is clearly stated from “go”
    • established houndaries make breaking them an intentional decision
  • ma says “I have all things are in brain at all times”. he doesn’t live with a feeling of the inflexibility of any of these things
    • i say “decision” is a tactic for survival. i make functional (and knowingly wrong) decisions on things until they’re more important
  • em says she is someone who is projecting doom and planning to avoid. wants rules to “hold the line” (safety). constantly deciding “rigid” until not
  • dan suggests that it might be easier when applying these things to trivial things
  • em says “coffee is a functional non-negotiable”
  • i go off for a bit about the etymology of “decision”, which means “to cut off” and something stupid about “tri-tips being a weird cut of beef that dissallow other cuts from being made”
  • concept [lost attribution] freelancing and camping
  • i suggest “preciding” as the functional value of “pledges"
    • "decided until proven undecided”

4 Block Box Thinking

Reality Doesn’t Care About Your Feelings; or, Why Every False Step Improves Your Life


Quick pain; quick progress

”Stay with the pain; don’t shut this out. This is your pain. This is your burning hand. It’s right here.” — Tyler Durden

We have to fight against pain avoidence.
We have to run into the spike.
We have to be brutal with ourselves if we plan to progress.
Pain is progress.


  • the success after a failing. researchers mind. what is the virtuous change we can make
  • ”in aviation, everything we know is because someone died”
  • radical exceptance
  • unhappiness shifts it’s focus
  • Obscurantist: the practice of deliberately presenting information in an imprecise, abstruse manner designed to limit further inquiry and understanding.
  • “nothing is more fatiguing and more exasperating than the daily effort of believe things that daily become more incredible…” — Bertrand Russell, The Conquest of Happiness
  • “consider calmly the hypothesis that they are bad plays”
  • seeing others more clearly than we do ourselves.
    • i’ve had a strategy at times to say to trusted advisors “i will do exactly what you tell me to do”
  • if you can’t see where you’ve got a foot wrong, you will fall flat on your face again.
  • ”don’t wait for the consequences to unfold. if you don’t deal with reality, it will deal with you"
  • "problems don’t improve with age”

Thoughts with friends

  • em is annoyed that he said we don’t see our flaws clearly. feels just as critical of herself as of others
    • ally agrees and feels the author has a “tone of authority as if everyone is the same”
  • i interpret it as “it’s easier to see when someone else is in the weeds than when we ourselves are”
  • ma thinks it’s so much easier to deconstruct when others went wrong
    • i suggest that we tende to put “us” and “them” on opposite ends of a continuum: “it’s easy to see where things went wrong <------> it’s complicated”
    • allie feels the opposite. she sees where she went wrong and can easily justify why ‘it’s complicated’ for others
  • ma shares journaling as a tool for objectively noting your own life
  • emily likes guided practice of “document what happened” not “how it felt”
    • easy to identify self as source of personal anxiety
    • ma’s therapist says “you’re telling the story wrong”
  • i mention what a cool fucking word “obscurantist” is — de-focusing the core of your problem as a way to avoid finding a solution
    • observing my own thoughts “i was the person who inserted the connective tissue between these two objectively unrelated things”
  • allie harkens back to the first chapter“lying to yourself with or without intention”?
  • ma calls this “back-solving”. does this really well at work but not in personal life
  • i’m an effective historian at planning center… wait, that’s always been a liability. shit. maybe i should stop and just do that publicly instead. at least focus it to only things that can be generalized
    • emily feels bad at this for work. has to reconstruct history every time
  • i mention the line “in aviation, everything we know is because someone died”. feels true but an extreme version of truth
    • dma asks “can we ever have enough data?“
    • i suggest that we can always measure first. don’t have to have all data but definitely enough to prove a thesis
      • american hubris likes to “intentionally throw out the black box”
        • the practical effects of that is that, when we have problems, we don’t have the tools or capacity to have “productive thought” (ref to allie)
      • ma consideres airline vs uber/lyft (prop 22). airlines feel effects immediately
      • i say that airlines front-loaded the pain and then developed a practice that informed every day after that. quick pain; quick progress. vs hubris first, solutions later.
      • ma says (of work) it’s easier to write fixes than to sit with the pain

5 Counterproductivity

Why Timesavers Are Often Timewasters


The things own eventually own us

Nothing is intrinsicly valuable.
If we know a thing is valuable in our life, use it.
But interogate your assumptions around optimization.
Know the full cost before saying yes — especially with technology which is “self-enlarging”.


  • Car
    • the total cost of a thing
    • car average speed is walking pace
  • ”counter-productivity”
    • savings vanishes once you do a “full cost analysis”
  • Email
    • spam, irrelevant messages, cost of computer and updates
    • $1/email
  • Presentations
    • sinking hours into presentation, not communication
    • ”arms race effect” — lost impact
    • hours lost to software
  • Peacock
    • every additional centimeter of plumage has a counter-productivity effect
  • Smart homes are a horror movie scenario
  • Digital Cameras
    • The overwhelm of choice and editing
    • Exploitable
    • Hard drives
  • Technology is self-enlarging
  • If it doesn’t enhance your life, don’t use it
  • ”Try switching on your brain instead of reaching for the nearest gadget”

Thoughts with friends

  • Dan has already internalized this as “what’s the full cost of this thing?“
    • asks “but do i just want to drive a car?"
    • "oops. i forgot onions. i’ll just jump back in the car and get those”
  • i posit that this creation of emergencies thru lack of planning and presence might be an enabled habit
    • example: nellie “streaming” a grocery list to me in real time vs us planning
  • dan says “we feel like we’re good with money. but we spent more than we made this month and we don’t know what it was on”
    • paper cut expenses
    • Amazon Prime as an enabler
  • em offers a counterpoint: when things aren’t easy, we tend to over-maximize on planning. “we’re getting groceries. let’s get together with so-n-so and do this that and the other thing”
    • not present in everything because you’re “maximizing” — hyper productivity
    • paying for it the next day in “recovery”
    • it’s emotionally challenging to intentionally not optimizing trips
  • ma asks how we can applying em’s experiences (the discipline required to live far from everything) to a person who lives close to a grocery store
  • i complain a but about the practicals not considered in the author’s equition: “do a want to walk 16 miles to work? instead of working?“
    • ma suggests that theme of the chapter is “are you questioning your assumptions”
  • ma calls out credit cards as a strong counterproductivityy area
  • i suggest a mental trigger: in a moment when you think to yourself “nailed it” ask “but did you?“
  • dan harkens back to the “inboxers” group:
    • tactics for combating notification lies: “you’ll never miss anything” and resulting anxiety
  • i channel C.S. Lewis for a second and blert out “the abolition of cleverness”
    • we see this is code a lot — the cost of cleverness
  • i go on a stupid tangent about Jane Jacobs again and the difference between observing artifacts and organism is in whether or not you account for time and the catholic principle of subsidiarity.
  • dan adds a book reference “Seeing like a State”
  • ma shares and i summarize here as “optimizations and interrogations” — inquiring of your assumptions
    • dan inquires “is productivity the actual bottleneck?“
      • we agree that communication is the the bottleneck
    • i suggest that we over-indexing on personal productivity over corporate productivity (communication)
  • ma almost loses me by incorporating an old trope: “maybe the real productivity is the friends we made along the way”

6 The Negative Art of the Good Life

  • There are bold pilots and there are old pilots.There are no bold, old pilots.
    • before: focus on the downside
    • the up-side will take care of itself
  • Tennis
    • in ameteur tennis, matches aren’t won, they’re lost
    • ”negative theology”
    • you don’t control the outcome. you control the inputs

7 The Ovarian Lottery

8 Thi Introspection Illusion

9 The Authenticity Trap

10 The Five-Second No

11 The Focusing Illusion

12 The Things You Buy Leave No Real Trace

13 Fuck-You Money

14 The Circle of Competence

15 The Secret of Persistence

16 The Tyranny of a Calling

17 The Prison of a Good Reputation

18 The “End of History” Illusion

19 The Smaller Meaning of Life

20 Your Two Selves

21 The Memory Bank

22 Life Stories Are Lies

23 The “Good Death” Fallacy

24 The Spiral of Self-Pity

25 Hedonism and Eudemonia

26 The Circle of Dignity — Part I

27 The Circle of Dignity — Part II

28 The Circle of Dignity — Part III

29 The Books of Worries

30 The Opinion Valcano

31 Your Mental Fortress

32 Envy

33 Prevention

34 Mental Relief Work

35 The Focus Trap

36 Read Less, But Twice—on Principles

37 The Dogma Trap

38 Mental Subtraction

39 The Point of Maximum Deliberation

40 Other People’s Shoes

41 The Illusion of Changing the World — Part I

42 The Illusion of Changing the World — Part II

43 The “Just World” Fallacy

44 Cargo Cults

45 If You Run Your Own Race, You Can’t Lose

46 The Arms Race

47 Making Friends with Weirdos

48 The Secretary Problemw

49 Managing Expectations

50 Sturgeon’s Law

51 In Praise of Modesty

52 Inner Success