I have a tool for thinking I call “steelman solitaire” that I have found comes to much better conclusions than doing “free-style” thinking, so I thought I should share it with more people. In summary, it consists of arguing with yourself in the program Workflowy, alternating between writing a steelman of an argument, a steelman of a counter-argument, a steelman of a counter-counter-argument, etc. (I will explain steelmanning later in the post; in brief, it is the opposite of a strawman argument. Steelmanning means trying present the strongest possible version of an opposing view.) In this blog post I’ll first explain the broad steps, then list the benefits, and finally, go into more depth on how to do it.
The broad idea
Strawmanning means presenting the opposing view in the least charitable light, often so uncharitably that it does not resemble the view that the other side actually holds. The term of steelmanning was invented as a counter to this; it means taking the opposing view and trying to present it in its strongest form. This has sometimes been criticized because often the alternative belief proposed by a steelman also isn’t what the other people actually believe. For example, there’s a steelman argument that states that the reason organic food is good is because monopolies are generally bad and Monsanto having a monopoly on food could lead to disastrous consequences. This might indeed be a belief held by some people who are pro-organic, but a huge percentage of people are just falling prey to the naturalistic fallacy.
Nonetheless, while steelmanning may not be perfect for understanding people’s true reasons for believing propositions, it is very good for coming to more accurate beliefs yourself. If the reason you believe you don’t have to care about buying organic is because you believe that people only buy organic because of the naturalistic fallacy, you might be missing out on the fact that there’s a good reason for you to buy organic because you think monopolies on food are dangerous.
However, and this is where steelmanning back and forth comes in, what if buying organic doesn’t necessarily lead to breaking the monopoly? Maybe upon further investigation, Monsanto doesn’t have a monopoly? Or there are multiple organizations who have copyrighted different gene edits so there’s no true monopoly?
The idea behind steelmanning solitaire is to not stop at steelmanning the opposing view. It’s to steelman the counter-counter-argument as well. As has been said by more eloquent people than myself, you can’t consider an argument and counter-argument and consider yourself a virtuous rationalist. There are very long chains of counter^x arguments, and you want to consider the steelman of each of them. Don’t pick any side in advance. Just commit to trying to find the true answer.
This is all well and good in principle but can be challenging to keep it organized. This is where Workflowy comes in. Workflowy allows you to have counter-arguments nested under arguments, counter-counter-arguments nested under counter-arguments, and so forth. That way you can zoom in and out and focus on one particular line of reasoning, realize you’ve gone so deep you’ve lost the forest for the trees, zoom out, and realize what triggered the consideration in the first place. It also allows you to quickly look at the main arguments for and against. Here’s a worked example for a question.
Tips and tricks
That’s the broad-strokes explanation of the method. Below, I’ll list a few pointers that I follow, though please do experiment and tweak. This is by no means a final product.
Acknowledgements. I’d like to thank Spencer Greenberg for both inspiring the original idea with Clearer Thinking’s Belief Challenger tool and for coming up with a much better name for the concept than my original “steelmanning back and forth”.