Steelman Solitaire: How Self-Debate in Workflowy/Roam Beats Freestyle Thinking

​I have a tool for thinking that I call “steelman solitaire”. I have found that it 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/Roam/any infinitely-nesting-bullet-points software, alternating between writing a steelman of an argument, a steelman of a counter-argument, a steelman of a counter-counter-argument, etc. 

In this post I’ll first list the benefits, then explain the broad steps, and finally, go into more depth on how to do it.

Benefits

1. Structure forces you to do the thing you know you should do anyway. Most people reading this already know that it’s important to consider the best arguments on all sides instead of just considering the weakest on the other. Many already know that you can’t just consider a counter-argument then consider yourself done. However, it’s easy to forget to do so. The structure of this method makes you much more likely to follow through with your existing rational aspirations.
2. Clarifies thinking. I’m sure everybody has experienced a discussion that’s gone all over the place, and by the end, you’re more confused than when you started. Some points get lost and forgotten while others dominate. This approach helps to organize and clarify your thinking, revealing holes and strengths in different lines of thought.
3. More likely to change your mind. As much as we aspire not to, most people, even the most competent rationalists, will often become entrenched in a position due to the nature of conversations. In steelman solitaire, there’s no other person to lose face to or to hurt your feelings. This often makes it more likely to change your mind than a lot of other methods.
4. Makes you think much more deeply than usual. A common feature of people I would describe as “deep thinkers” is that they’ve often already thought of my counter-argument, and the counter-counter-counter-etc-argument. This method will make you really dig deep into an issue.
5. Dealing with steelmen that are compelling to you. A problem with a lot of debates is that what is convincing to the other person isn’t convincing to you, even though there are actually good arguments out there. This method allows you to think of those reasons instead of getting caught up with what another person thinks should convince you.
6. You can look back at why you came to the belief you have. Like most intellectually-oriented people, I have a lot of opinions. Sometimes so many that I forget why I came to hold them in the first place (but I vaguely remember that it was a good reason, I’m sure). Writing things down can help you refer back to them later and re-evaluate.
7. Better at coming to the truth than most methods. For the above reasons, I think that this method makes you more likely to come to accurate beliefs.
   
   

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 that 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. 

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 that 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 maybe multiple organizations have copyrighted different gene edits, so there’s no true monopoly.

The idea behind steelman 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 organized. This is where Workflowy or Roam 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
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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.  

1. Name your arguments. Instead of just saying “we should buy organic because Monsanto is forming a monopoly and monopolies can lead to abuses of power”, call it “monopoly argument” in bold at the front of the bullet point then write the full argument in normal font. Naming arguments condenses the argument and gives you more cognitive workspace to play around with. It also allows you to see your arguments from a bird’s eye view.
2. Insult yourself sometimes. I usually (always) make fun of myself or my arguments while using this technique, just because it’s funny. Making your deep thinking more enjoyable makes you more likely to do it instead of putting it off forever, much like including a jelly bean in your vitamin regimen to incentivize you to take that giant gross pill you know you should take.
3. Mark arguments as resolved as they become resolved. If you dive deep into an argument and come to the conclusion that it’s not compelling, then mark it clearly as done. I write “rsv” at the beginning of the entry to remind me, but you can use anything that will remind you that you’re no longer concerned with that argument. Follow up with a little note at the beginning of the thread giving either a short explanation detailing why it’s ruled out, or, ideally, just the named argument that beat it.
4. Prioritize ruling out arguments. This is a good general approach to life and one we use in our research at Charity Entrepreneurship. Try to find out as soon as possible whether something isn’t going to work. Take a moment when you’re thinking of arguments to think of the angles that are most likely to destroy something quickly, then prioritize investigating those. That will allow you to get through more arguments faster, and thus, come to more correct conclusions over your lifetime.
5. Start with the trigger. Start with a section where you describe what triggered the thought. This can often help you get to the true question you’re trying to answer. A huge trick to coming to correct conclusions is asking the right questions in the first place.
6. Use in spreadsheet decision-making. If you’re using the spreadsheet decision-making system, then you can play steelman solitaire to help you fill in the cells comparing different options.
7. Use for decisions and problem-solving generally. This method can be used for claims about how the universe is, but it can also be applied to decision-making and problem-solving generally. Just start with a problem statement or decision you’re contemplating, make a list of possible solutions, then play steelman solitaire on those options.

Conclusion

In summary, steelman solitaire means steelmanning arguments back and forth repeatedly. It helps with:

• Coming to more correct beliefs
• Getting out of unproductive conversations
• Making sure you do epistemically virtuous things that you already know you should do

The method to follow is to make a claim, make a steelman against that claim, then a steelman against that claim, and on and on until you can’t anymore or are convinced one way or the other.

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