The real test of critical thinking is whether you can engage with arguments you hate
Thirteen essays in, and the toolkit is starting to look pretty solid. How your brain runs on faulty autopilot. How it takes shortcuts and defends its own ego. And then the logical tools – how to identify premises and conclusions, tell deduction from induction, surface hidden assumptions.
If you’ve been paying attention, you’re now extremely good at finding weaknesses in arguments you already disagree with.
Which is exactly the problem.
I’ll use myself as an example. Somebody from the other political tribe makes a claim, and I immediately start reconstructing their argument in the weakest possible form. Looking for the gaps, the fallacies, the hidden assumptions that fall apart under any real scrutiny. Building what philosophers call a straw man – a deliberately weak version of the argument that’s easy to knock down.
It feels good. It feels like thinking.
It’s actually the opposite of good critical thinking.
Nigel Warburton calls this out in Thinking from A to Z. The Principle of Charity demands interpreting arguments in their strongest possible form. Not the weakest. Not the easiest to dismiss. The best case that the person could reasonably be making.
This runs against every instinct the series has been building up to this point. But if the goal is actually figuring out whether an argument is sound, instead of just scoring points, you have to engage with the steel man, not the straw man.
Here’s what that looks like in practice.
Somebody argues that immigration should be reduced because it depresses wages for American workers. The straw man version of the response – “oh, so you just hate foreigners.” That’s satisfying. It completely sidesteps the economic claim, which was the actual point being made.
The steel man version – “you’re arguing that increasing labor supply in certain sectors reduces bargaining power for workers already in those sectors, and immigration policy should account for domestic labor market conditions.” Now there’s something to actually work with. You can examine the evidence. You can look at the trade-offs. You can engage with the real claim instead of calling somebody racist and walking away.
Notice what just happened. Being charitable doesn’t mean conceding the argument is correct. It just means stating the argument in a form where you can evaluate whether it’s correct.
This is what the philosopher Daniel Dennett calls the first step of productive criticism – you should be able to restate somebody’s position so clearly and fairly that they say “thanks, I wish I’d thought of putting it that way.” Until you can do that, you aren’t actually arguing against their position. You’re arguing against a version of their position you made up.
All of this is extremely difficult because it requires setting aside the confirmation bias from Essay 6.
When somebody encounters an argument from a person they already disagree with, their brain is primed to reject it before it’s even fully heard. System 1 is looking for reasons to dismiss it. The halo effect from Essay 8 is kicking in – if you dislike the person making the argument, you’re predisposed to find the argument stupid. If you like them, same thing in reverse.
Forcing yourself to construct the steel man version fights all of that. It forces slowing down. It engages System 2. It requires you to actually understand what’s being claimed before deciding whether it’s wrong.
Here’s the uncomfortable part.
When you apply this honestly, you’ll start to find that some arguments you thought were completely idiotic actually have more merit than you realized. Not necessarily that they’re right. Just that the strongest version is harder to dismiss than the weak version you’ve been attacking.
I tested this on myself with arguments for raising the minimum wage. My immediate reaction to business owners complaining was to dismiss them as greedy. That was the straw man. The steel man: “If your business model only works by paying employees wages so low they need government assistance to survive, you don’t have a profitable business – you have a scheme where taxpayers subsidize your labor costs. A real business should generate enough value to pay workers a livable wage.”
That’s the actual argument. You can disagree about what counts as “livable.” You can argue about regional cost of living differences. But you can’t just dismiss the whole thing as not understanding economics.
And this is where critical thinking gets genuinely hard. It’s not just about finding flaws in bad arguments. It’s about honestly engaging with GOOD arguments from people you disagree with, and doing the work of figuring out whether they have a point.
Warburton points out that being charitable is primarily an intellectual exercise. Your opponent in a real conversation might not even defend the reconstructed version of their own argument. But that isn’t the point. You can’t claim to be reasoning well if the only arguments you’re capable of defeating are ones nobody actually holds.
The Principle of Charity is a commitment to intellectual honesty. It says – I will engage with the strongest version of your argument before I dismiss it. I will assume you have reasons, even if I ultimately conclude those reasons aren’t sufficient. I will argue with what you actually believe, not with a cartoon of what you believe.
When the stakes are high, and you genuinely believe somebody’s position is causing real harm, being charitable can feel dangerous. It can feel like giving ground. But if you only know how to defeat straw men, you’re completely unprepared the moment somebody articulates the steel man version of the same argument.
Critical thinking isn’t a game where the goal is feeling superior. The goal is figuring out what’s actually true.
This is the real test.
Can you state your opponent’s position so well they’d thank you for the clarity? Or are you more interested in caricaturing their position so you can walk away feeling like you won?