Skin in the Game

Core knowledge: List of common human goals
Part 1: Exploration-Exploitation
Part 1a: The application of the secretary problem to real life dating
Part 1b: adding and removing complexity from models
Part 2: Bargaining Trade-offs to your brain.
Part 2a.1: A strategy against the call of the void.
Part 2a.2: The call of the void
Part 2b.1: Empirical time management
Part 2b.2: Memory and notepads
Part 3: The time that you have
Part 3a: A purpose finding exercise
Part 3b: Schelling points, trajectories and iteration cycles
Part 4: What does that look like in practice?
Part 4a: Lost purposes – Doing what’s easy or what’s important
Part 4b.1: In support of yak shaving
Part 4b.2: Yak shaving 2
Part 4c: Filter on the way in, Filter on the way out…
Part 4d.1: Scientific method
Part 4d.2: Quantified self
Part 5: Skin in the game
Part 6
Call to action

A note about the contents list; you can find the list in the main parts, the a,b,c parts are linked to from the main posts.  If you understand them in the context they are mentioned you can probably skip them, but if you need the explanation, click through.


We describe armchair philosophers, the likes of classical philosophers who really didn’t have access to science the way we do today.  All they could do is sit in their chairs and ponder.  It gives images of Freud in his study full of books.  The thinker, great people sitting back and thinking.

But then there’s the dark side of the armchair philosopher.  The likes of the junk-food only dieting,  children-in-adult bodies.  People not in control of their environments.  Some sort of gratification haven setup.  People who talk the talk more than they walk the walk.  Spending more time theorising about evolutionary psychology and what it suggests about social interaction than actually going out and practicing social interaction.  I mean…  Do they even walk?  Do they even run?  Do they even lift?  Could they answer if asked why we even lift?  Yes.  I am talking about your average chat-room, forum, tweeting, Click-tivist, anti-social, keeps to themselves and brooding against the world.

This post is about a very specific failure mode – not having skin in the game, as it aligns with myself and Lesswrong.  This post is mostly to help me look at myself and send a message that I am not working hard enough (remembering that advice comes on a spectrum and you should sometimes reverse the advice that you hear).  And for that I say, I am sorry and I am going to try and work harder.


I get a lot of joy from climbing the abstraction ladder, and being able to comment on a phenomena without actually being concrete.  Then I get a lot of joy out of being concrete and specifying how ideas relate to the real world.  I often share with people that I am a collector of models of thinking (one day I will write a list) – the lenses through which one can see the world and understand what they see.

We know from mental contrasting that when we imagine a goal and only achieving the goal we don’t necessarily get motivated to further achieve the goal.  instead it’s a matter of imagining the contrast between the goal and the barriers or also the goal and what it might feel like to not succeed.  Just visualising the positive doesn’t encourage you to reach the goal.  Looking at whether you should share your goals through this lens starts to make more sense now.

I bring up mental contrasting to warn about the hazard of too much armchair activity.  Really embodied in the click-tivist trolley problem –


There is more to this problem than meets the eye, it’s not just that armchair activism is laaame and doesn’t actually “do” things, it’s also that you have a trade-off, there is an opportunity cost between your choices of what you do with your time.  You trade off maybe saving a life with maybe alerting more people to save a life.  If you can alert 11 people with a 10% chance each of actually saving a life, instead of saving the life yourself, by doing some math, you can statistically save 110% of each life when you do that.  Unfortunately in some branches of the multiverse that means that 0 people are saved, however in other branches – 11 lives or more are saved.

Everything you are doing with your time is also conversely everything you are choosing not to do with your time.  Your revealed preferences already show you previously didn’t want to do plenty of things with your time.

If you are just sharpening the saw you are only doing half of the puzzle.  If you are only cutting a tree down with a blunt saw you are also only doing half of the puzzle.  Both are failure modes.

If you only ever sit in your click-tivist chair and you have never done any exercises in rationality, you don’t have your skin in the game.


I bring this up with an apology, I am more at fault than most.  I have this crazy habit of writing out a to-do list and then (assuming I finish writing the list), putting the list down and doing something different.  Insanity would be to do the same thing again and expecting a different result.

I call this problem a problem of not having skin in the game.  The ability to talk very seriously about everything that is broken and then go on to do nothing.  Among many in the list:

  • Converting people to donate to EA
  • Sticking to your diet even on bad days
  • Actually doing exercises you find in rationality posts
  • Voting for the political party that you think will actually change things.
  • Noticing when things surprise you and then changing the way you think, updating your models of understanding so that you are less surprised in the future.

In this sense having a system (having a strategy), writing a to-do list is a good move, but not actually being connected to it is a broken system.


Skin in the game classically applies to betting on the stock market.  How many people today are saying, “I wish I bought bitcoin early on, I wish I bought some Microsoft shares…”.  As a guy sitting on the sidelines of a football match you don’t get tackled by other people playing the game, but you also never score a goal, never take home points for your team.  On the one hand it’s very safe to be on the sidelines.  You don’t get tackled.  But it also means you can never win.  No touchdown to your name.

Football not your game.  That’s okay.  We can’t all be winning football players.  But I guarantee there is something out there for which you do want to be in the game.  It might not be the same game as other people.  And that’s okay.  Life is an endless trade off between what we have time to do and what we don’t have time to do.  And for a lot of life you can get away with not playing the same game.  I want to encourage you to do that.  For all of the bits that you can avoid wasting time on, avoid wasting time on them.  But you don’t want to be the knife thrower who shows up to play Russian roulette.

Which is to say that there are probably some metrics by which you need to measure yourself whether you like it or not.  And this is not about comparing yourself to your neighbour, (which if done from a place of safety – can be very valuable) but in fact this is about comparing yourself to yourself.

Here are some:

  • Am I as healthy as I could be?  As I want to be?
  • Am I as secure as I could be?  As I want to be?
  • Am I as wealthy as I could be?  As I want to be?
  • Am I as happy as I could be? As I want to be?
  • Am I as fulfilled as I could be?  As I want to be?
  • Am I as productive as I could be?  As I want to be?
  • Am I reaching the goals that I could be?  That I want to be?
  • Am I learning everything I could be learning?  That I want to be?
  • (as efficiently as I could be?  As I want to be?)

Having skin in the game is about taking that look at yourself in the mirror.  Look at yourself and see if you are where you want to be.  If you are actually as connected in your intentions as you want to be.  Are you doing what you want to be doing?  Are you really using your time the way you want to be using your time?

Exercise: Take 5 minutes, make two lists:

  • a list of the things that matter
  • a list of things that don’t matter

Come up with your own ideas before looking at this list but – here are some examples of things that might matter or might not matter:

  • Maintaining a spiritual connection
  • Spending an hour a day learning
  • Spending an hour a day with good company
  • Practising a musical instrument
  • Being in control of your emotions, not being angry or upset too often
  • Being healthy
  • Having an hour a day dedicated to writing or drawing or knitting or some other craft or creativity
  • Spending an hour a day exercising
  • Eating good food
  • Doing exciting things, having exciting experiences
  • Not being stuck in too many commitments
  • Being committed to lots of things
  • Feeling romantically fulfilled
  • Obtaining fame or a following
  • Seeking political success
  • Having a family or community
  • The world is a fair place
  • I am happy
  •  I have friends
  • I see reality for what it is
  • The world is a better place in the future
  • I see things that are worth seeing
  • I have lots of money
  • I have lots of time to do what I want.

I can’t really say what’s important for you, but maybe with these ideas and your own in mind, you can set out and ask yourself about the things that matter.

Am I doing enough about this? Am I properly invested into the things I care about?  Is my skin in the game on all the things that matter to me?


Meta: I have developed some bad habits around not liking my writing enough and getting stuck making many revisions.  I also have some bad habits around having high impulsivity and being disconnected from my expectancy of the value that these things will yield.  I really think that writing is important but I seem to forget that I care about it.  This took a cumulative 7+ hours to write but due to said problems above I feel like it’s not higher quality but took longer than usual to write.


Core knowledge: List of common human goals
Part 1: Exploration-Exploitation
Part 1a: The application of the secretary problem to real life dating
Part 1b: adding and removing complexity from models
Part 2: Bargaining Trade-offs to your brain.
Part 2a.1: A strategy against the call of the void.
Part 2a.2: The call of the void
Part 2b.1: Empirical time management
Part 2b.2: Memory and notepads
Part 3: The time that you have
Part 3a: A purpose finding exercise
Part 3b: Schelling points, trajectories and iteration cycles
Part 4: What does that look like in practice?
Part 4a: Lost purposes – Doing what’s easy or what’s important
Part 4b.1: In support of yak shaving
Part 4b.2: Yak shaving 2
Part 4c: Filter on the way in, Filter on the way out…
Part 4d.1: Scientific method
Part 4d.2: Quantified self
Part 5: Skin in the game
Part 6
Call to action

A note about the contents list; you can find the list in the main parts, the a,b,c parts are linked to from the main posts.  If you understand them in the context they are mentioned you can probably skip them, but if you need the explanation, click through.

Next: Part 6Call to action

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