Thinking About Not-Knowing

Vaughn Tan wants to help you learn how to think and act better in situations of not-knowing.   

Vaughn Tan is writing a book about different types of not-knowing and what we can do about them — he’s figuring this out as he goes, and he wants fellow explorers to join him on his journey in his 14 episode salon series.

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In addition to series tickets, members get access to our community Discord (with a channel for this series to chat between events)—as well as free salon tickets each month, discounts, free members-only events, and more.

Every day, either personally or professionally, we confront big and small situations where we must act with partial information. This means that we keep encountering situations of not-knowing in which we must still do something. The most important types of work humans can do are those that navigate significant not-knowing. We are most human when we are responding to not-knowing, because anything that it fully known and knowable becomes routine and replaceable easily by machines.

This is why we reward leaders who (in theory) lead their companies and countries through unpredictable situations, why we respect startup founders who work with not-yet-understood technology and markets to create new companies, and why we esteem researchers who work at the edge of the known to create new knowledge.

But the last few years of a global pandemic, extreme weather, geopolitical insecurity, and economic disruption (among so many other things!) show that there are different types of situations of not-knowing. And they are growing in number, scope, and impact. Every one of us will have to learn how to adapt to this.

Learning how to live on and live well in spite of not-knowing is a path to surviving and flourishing in an increasingly uncertain world. The problem is that we’re poorly prepared to even understand not-knowing, let alone know how to respond to it. The rapid ascent, sudden demise, and flood of coverage of Effective Altruism, FTX, and Alameda Research captures how poorly not-knowing is understood even among those whose profession it is to navigate it (such as many philosophers, venture capitalists, finance industry professionals, and financial journalists).

We urgently need better tools for thinking and action in situations of not-knowing. This is what the book and salon series will explore. One of the underlying assumptions is that the same framework and approach for thinking clearly about not-knowing applies in both personal and professional life — what changes is the context to which that framework and approach is applied.

This series may be a good fit if you’re facing personal or professional situations of not-knowing, and want more pragmatic ways to understand what they are, what causes them, and therefore how to make better decisions (and take better actions) to affect them. Not-knowing raises questions about how to think and act, and from Vaughn’s personal experience in the last 15 years, some questions for which this series may be relevant include:

  • “What can I do to think through my personal identity at a time when my assumptions about what a good career is have been swept away by Covid / inflation / disillusionment / etc?”
  • “What can I do to design an organization that can build really innovative products when the board just wants the company to hit quarterly sales targets?”
  • “What can I do to figure out where I should live for the next month/year/decade?”
  • “What can I do to better manage innovation work?”
  • “What can I do to become more comfortable with trying and learning new things?”
  • “What should I do to live an ethically responsible life with a long-termist view?”

Before each of the 14 monthly sessions, Vaughn will send around a short extract from his book draft as a frame for thinking and a starting point for discussion.

During each session, expect discussions and thought experiments. Come with points of view and real-life situations of not-knowing to think about collectively. We will discuss serious things but try to avoid taking ourselves too seriously.

***NOTE: This salon series will be recorded.***

Date and Time: Third Thursday of every month at 8 PM CET

Already have a membership? Sign in to get your series ticket.

In addition to series tickets, members get access to our community Discord (with a channel for this series to chat between events)—as well as free salon tickets each month, discounts, free members-only events, and more.

Episode Table of Contents

#DateEpisode / Topic
1Jan. 19thIntroduction.
2Feb. 16thNot-knowing and happiness.
3Mar. 16thFear is the mind-killer.
4Apr. 20thMisnaming the beasts.
5May. 18thFalse advertising.
6Jun. 15thActions and results.
7Jul. 20thConnecting actions and their results.
8Aug. 17thWhat results are worth.
9Sep. 21stThe fog of time.
10Oct. 19thIntent, causation, and values.
11Nov. 16thMindset change.
12Dec. 21stBroad approaches.
13Jan. 18th
Tools for thought and action.
14Feb. 15thA clear view.

Episode Summaries

Section 1 (Episodes 1-2): Why Bother?

Here we set the stage for the rest of the series by considering why the world we inhabit is becoming more uncertain, how that forces us to think more clearly about not-knowing, and why doing so is a path to being happier and more successful.

1: Introduction. Why the world is becoming increasingly uncertain and unknowable as it becomes ever more complex and more interdependent. How this causes people to make poor decisions, have inaccurate expectations, and generally be less happy and successful than they could be. Thinking clearly about not-knowing is one path to happiness. Why this series is about a general way to think about and act in situations of not-knowing. Why it is not a series only about risk, uncertainty, complexity, chaos, or ambiguity (which all feed into not-knowing).

2: Not-knowing and happiness. Why thinking clearly about not-knowing makes us 1) more curious, 2) more free, 3) more effective, and 4) more content — and thus happier and more successful in an increasingly uncertain world.

Section 2 (Episodes 3-5): Clearing the Ground

To begin, we explore three obstacles to thinking clearly about not-knowing. First, our fear of the unknown (both from evolution and from social dynamics) which prevents us from looking closely at situations of not-knowing. Second, our long-standing habit of colloquially calling everything risk. Finally, the growing practice among computer scientists and technologists to claim that they have methods for dealing with true uncertainty (spoiler: they usually don’t).

3: Fear is the mindkiller. Humans viscerally fear the unknown in a way that usually prevents us from dwelling on it properly. We have an evolved, physiological aversion to the unknown that was very useful for survival thousands of years ago but is maladapted to the modern environment. On top of that, social norms and dynamics push us to pretend to be certain even when we’re not, because as social animals we’re deeply afraid of losing face in front of others.

4: Misnaming the beasts. We use the same word “risk” to describe many different situations of not-knowing, so we always mix them up without meaning to. Things end up being called “risk” (even when they aren’t) — usually this is to make them seem more knowable than they really are. This session will clarify the differences between several of the most common situations that are all called “risk,” and think through why they are important to distinguish from each other.

5: False advertising. At the same time, many approaches advertised as designed to deal with uncertainty actually deal with either very specific types of uncertainty or risk — usually this is to make them seem better at dealing with difficult problems of uncertainty than they actually are. By the end of this session, we might have a very healthy skepticism of technology that claims to deal properly with uncertainty.

Section 3 (Episodes 6-9): Laying the Foundations

After sweeping away the obstacles, we can start thinking clearly about the different kinds of not-knowing we face. Each of the next four sessions focuses on a different source of not-knowing. We’ll unpack each source’s implications to understand why and how to respond to it differently from the others. Each of the four sessions also asks what it means to take successful and effective action given that particular source of not-knowing.

6: Actions and results. The most easily understood type is simply not knowing what actions you can take and what outcomes are possible.
1) As technology advances, we have more and more tools at our disposal. This means that we often don’t know the full range of actions that we could take in a given situation.
2) As the world becomes more complex and interconnected, we also are unaware of many possible outcomes — in particular those outcomes that are created by conditions beyond our direct control.

7: Connecting actions and their results. Increasingly frequently, we also don’t know exactly how much one or more outcomes is connected to a given action. There are in fact at least four distinct sources of not-knowing in causation.
1) Quantification obsession and legibility obsession means we assign precise probabilities (or probability ranges) to outcomes without strong basis — this has become habitual and taken for granted.
2) When actions are unknown, we can’t know how likely they are to produce particular outcomes.
3) When outcomes are unknown, we cannot know when particular actions will produce them.
4) We are often only partly aware of the causal connections between an action and a range of simultaneously produced outcomes.

8: What results are worth. Not knowing how much particular outcomes are worth to you. This is the most under-explored, despite being the basis of expected value theory (which drives so much long-termist decision-making, including much of the Effective Altruism movement). Without valuing outcomes, it’s impossible to compare them and choose actions. Yet how we value outcomes often changes over time, for at least two reasons:
1) We learn about new outcomes to pursue which we value more, or which change how much we value existing outcomes.
2) We learn about new actions we can take, which change the cost of achieving particular outcomes.

9: The fog of time. The length of the time horizon also exacerbates not-knowing. Present actions affect future outcomes, but the environment in which actions are taken changes over time. The longer the time horizon, the more likely it is that we discover new actions and new outcomes, or that the environment changes so that causation and/or valuation changes.

Section 4 (Episodes 10-13): A Not-knowing Toolkit

We’ve become used to decision-making approaches and tools that are ultimately only appropriate for situations of formal risk. These approaches and tools are sharp-edged, legible, explicable, and easily put into books. Tooling up for other kinds of not-knowing is particularly hard because it requires fundamental changes in how we think about why we act (intent), how we think about taking action (causation), and how we understand success (values). The appropriate approaches and tools for other kinds of not-knowing look and feel different: They are more amorphous, less legible, and resist being grasped quickly. They rely a lot on tacit knowledge that only develops with practice and repetition

10: Intent, causation, and values. Not-knowing reverberates back and forth between actions, outcomes, causation, and valuation: A change in one of them can affect the others. This means that the approaches and tools of not-knowing must do their best to accommodate how a change in one of the four affects how you think about the rest. This requires a fundamentally different way of thinking about the world and how to take action in it; in other words, a mindset change.

11: Mindset change. An appropriate mindset is founded in clearly recognising different non-risk forms of not-knowing. Because of this it privileges thinking and acting in ways which increase degrees of freedom to act (a strategy of tactics) by exploring the interrelationships between actions, outcomes, causation, and values.

12: Broad approaches. Broad principles for dealing with not-knowing:

  • Small experiments instead of big bets.
  • Experiments which explore real spaces of not-knowing.
  • Stacking the deck.
  • Superordination of goals.

13: Tools for thought and action. Concrete tools for use in situations of not-knowing:

  • Superordination during goal-setting.
  • Clearly identifying non-goals.
  • Using forced choices to reveal tradeoffs.
  • Resisting false quantification.
  • Identifying highly loaded causation.
  • Desperation by design.
  • Implication analysis.
  • Question lists.

Section 5 (Episode 14): The Path Forward

14: A clear view. In the final session, we briefly review the arc of the salon series and then return to explore in more informed detail how clear thinking about not-knowing can be a vector for happiness.

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