Think Again

Knowing What You Don’t Know

Author: Adam Grant

Recommended by current tennis buddy and future VC Joycelyn Feng after I complained I didn’t want to read any of the books I bought.

This wasn’t a mind-blowing book, but still thought provoking as over the last year I’ve found myself knowing that I don’t know, hopefully that changes soon :)

Below are some of my key takeaways.

Individual Rethinking

The act of revisiting and revising solutions empirically improves outcomes.

This isn’t due to alternate solutions being inherently better; Rather, the act of rethinking increases the probability of finding an alternate solution with stronger evidence or outcomes.

Expressed simply, it is not:

• Rethink → new idea → change belief → better outcome

Rather:

• Rethink → new idea → better outcome → change belief

Of course, not all reassessments of existing beliefs will be better or “more correct” - further elevating the importance of adopting an actively open-minded mindset in hope that a subset of those will evolve into better beliefs.

In static realms, intelligence is the ability to think and learn; In turbulent realms, intelligence is the ability to rethink and unlearn.

Interestingly, static realm intelligence introduces two main biases that build inertia against turbulent realm intelligence.

• Confirmation bias - seeing what we expect to see

• Desirability bias - seeing what we want to see

The “smarter” you are (rather, think you are), the better your ability to be self-assured in your beliefs and the harder it can be to see your own limitations.

The remedy is humility with an intellectual twist.

Humility is knowing that you don’t know

• I do think this is a natural onramp as it can become obvious by simply observing how brilliant other people are - and if it’s not obvious, perhaps it’s time to hop to a bigger pond.

Intelligent humility is knowing what you don’t know

• Still trying to figure this one out, I’ll get back to this hopefully.

• Obviously there’s levels to this - it’s quite easy to say “I don’t understand Buddhism”, it’s harder to say “I don’t know why despite intellectually understanding the Buddhist doctrine of impermanence, I still harbor desires that lead to suffering”.

Short-term Pessimism, Long-term Optimism

Navigating the world with doubts about every belief you hold seems like a nice way to develop a debilitating inferiority complex.

The “Confidence Sweet Spot” is introduced as a secure belief in yourself with an uncertain belief in your tools. I’m not sure I like this phrasing as it introduces a duality between you and your methods where I don’t think there is one.

Capturing a more non-dual, participatory stance between an individual and reality, I think this is better expressed as adopting a short-term pessimism and long-term optimism. Hypothesize how your ideas will affect reality, and in turn see how what happened in reality affected you; reality (or your beliefs about reality) may not have improved for now, but you’ve certainly improved your understanding of your connectedness to the world around you.

Associated with this evolution should be a deepening of the decision process, increasing its expressiveness in explaining reality as you accumulate counter-examples to your prior beliefs.

Interpersonal Rethinking

I don’t dance but here’s an analogy anyways.

In an attempt to consolidate this section succinctly, I’ll lean on the dance analogy that was introduced but don’t think was fleshed out properly. What I like about this analogy is it blurs monism and dualism - the boundary between two individuals still exists, but in a nebulous sense - each parter is free to move as they wish, but both are influenced by and hold the ability to influence their partner.

Acknowledging this freedom is important - if you force your partner to move in certain ways, they will stop dancing and walk away.

Instead, if you use your action not to invoke action, but suggest the possibility of action (affordances) - your partner will be be free to form hypotheses around the affordances of your actions and test them on you, leading to an ever improving intellectual dance of beliefs.

In short - work collaboratively and ask good questions :)

Collective Rethinking

Binary bias is the human tendency to seek clarity by binarizing complex spectrums.

Changing someone’s binary viewpoint is difficult - but by introducing complexity and acknowledge multitude and nebulosity of a topic, you also lower the friction of rethinking; now, instead of flipping one’s entire viewpoint, you afford them the possibility of ever-so-slightly tweaking one dimension of their belief without the added burden of simultaneously tackling all other dimensions at once.

This intuitively translates to the collective level (organizations, communities, etc.) as success are often expressed in terms of a limited set of metrics, but the complexity of how each member contributed to each process is lost if we rely on a binarized (or “dollarized”) outcome.

You can’t make a collective successful by telling it to do better. You make it successful by accounting for and constantly rethinking every process.