You've successfully subscribed to Not Overthinking
Great! Next, complete checkout for full access to Not Overthinking
Welcome back! You've successfully signed in.
Success! Your account is fully activated, you now have access to all content.
Success! Your billing info is updated.
Billing info update failed.

Disappointment, Seriousness and Sincerity

Disappointment, Seriousness and Sincerity
In this episode, Ali shares a disappointing moment from his week when System 1 thinking took hold of him.

In this episode, Ali shares a disappointing moment from his week when System 1 thinking took hold of him. We then discuss Alan Watts' famous framing of life as a game with two modes of operation - serious vs sincere. Taimur shares some lessons from his therapy sessions, and we end with an elaborate description of a problematic meme. Enjoy!

Here are some of the highlights from our discussion:

Alan Watts suggested that we should frame life as being like a game with two modes of playing – you can play the game sincerely or you can play it seriously. Someone who plays the game seriously is someone who forgets that it’s a game whereas those who play the game sincerely play it properly but recognise that it is still just a game. Our inflated sense of disappointment often arises when we fall into playing the life ‘game’ too seriously. The extent to which we treat things like a game depends upon how regularly we remind ourselves that we are playing it as a game.

When we’re trying to change our values, no amount of simple deliberation will change any particular value for you. You have to aspire towards the value by having some practical experience. There’s no amount of deliberation that will change this, you just have to hear the music a bunch of times. There’s no amount of deliberation that is going to instantly click in your brain that you’ll suddenly be motivated to do the thing. It comes from aspiring towards that and taking action and course correcting each time you take action.

With many of these things, it’s one thing knowing it intellectually and it’s another thing knowing it intuitively.

It’s helpful to have discussions to break down the thought process behind our gut reactions. If we don’t have the habit of questioning our moral intuitions, there’s no way to improve our thinking and move towards this aspirational future where our mindset shifts to something more legitimate.

It’s a mistake to think that we value everything that we believe valuable. Our capacity to believe that things are valuable far outstrips our capacity for personally investing ourselves in things we feel our valuable. In order to value something, we must engage with it in a way that takes time, effort and practice. Given our finite time and resources, we cannot devote ourselves to all the things we see as valuable.

The litmus test of people’s real values is what actually provokes an emotional response within you. Our mind often gravitates to what we think should be good values (not to lie, be kind) but this can diverge from how we actually behave in the moment. It is those things that we react to that are truly valuable to each of us.

This episode is kindly supported by Skillshare. Sign up at

Become a Not Overthinker

We've got a fun little members-only community where we have a private Slack channel, and host weekly (ish) Zoom hangouts. Click here if you fancy joining.

Leave us a Review

If you enjoy listening to the podcast, we'd love for you to leave us a review on iTunes / Apple Podcasts. Here's a link that works even if you're not on an iPhone :)

Send us an Audio Message

We really want to include more listener comments and questions in our episodes. If you've got any thoughts on this episode, or if you've got a conundrum or question you'd like us to discuss, send an audio file / voice note to