Thinking Outside the Box

Purpose
Sometimes an argument is built on hidden rules or values. “Thinking outside the box” means stepping outside the way the argument is set up so you can see it from a new angle. This can help you find blind spots, unfair rules, or hidden trade-offs.


Quick Example

Them: “Everyone should eat lunch at the same time so the team bonds more.”
You: “What if the managers had to eat on a staggered schedule so they could meet more people one-on-one? Would that help bonding too?” (Flip the Script)
Them: “Hmm, maybe not.”
You: “Or what if the rule was for interns instead of the full team? Would it work the same?” (Change the Cast)
Them: “That’s different…”
You: “What if the main goal was productivity instead of bonding—would the same lunch rule make sense?” (Switch the Goal)


The Three Main Moves

1. Flip the Script (Trigger: Reverse)

  • What it is: Switch who has the benefit and who has the burden.
  • Why it helps: Shows if the rule is fair both ways.
  • Example: If teachers had to wear uniforms instead of students, would it still make sense?
  • Ask after: “What’s different when the roles are switched?”

2. Change the Cast (Trigger: Swap)

  • What it is: Keep the same rule, but change who it applies to.
  • Why it helps: Finds out if the argument only works for certain people or groups.
  • Example: If part-time workers had to follow the same office rules as full-time staff, would it still be fair?
  • Ask after: “What’s the real difference between these groups?”

3. Switch the Goal (Trigger: Reframe)

  • What it is: Look at the same situation but with a different main value in mind.
  • Why it helps: Shows what we’re really choosing to prioritize.
  • Example: If the main goal is creativity instead of discipline, would uniforms help or hurt?
  • Ask after: “Which goal is most important here, and why?”

How to Use This in Conversation

  1. Hear them out — repeat their point back to be sure you understand.
  2. Pick one move — flip the script, change the cast, or switch the goal.
  3. Give your short reframe — 1–2 sentences is enough.
  4. Ask the follow-up question — this keeps it a real discussion, not a “gotcha.”

Tips

  • Use examples from neutral areas (sports, games, cooking) so people focus on the idea, not their feelings.
  • Say what you’re doing: “Let’s flip the roles for a second…”
  • Be ready to come back into their frame after—you’re not running away from the topic, you’re stress-testing it.

The Purpose of Dialogue

Open Question: What is the purpose of dialogue?

  • People generally only change their minds when in conversation with someone that loves them. How many conversations are we having with people we love?
  • Maybe the point of conversation is to change our own minds. If we aren’t coming from that place, are we in dialogue at all?
  • Trying to change other people’s mind is often a futile exercise. If true, then why bother having any dialogue at all?

Related: Agree to Disagree or Fight, Really Reading Means Being Open To Change, Arguing for a Different Reality, Celebrating Our Differences, and others.

How To Have A Good Conversation

“1. Set up the conversational premise so you, and the other person, have easy outs, if it is not a good match.

2. Don’t assume the conversation will last an hour.  Rapidly signal what kind of conversation you are good at, if anything going overboard in the preferred direction, again to establish whether the proper conversational match is in place.

3. If you notice something you want to say, say it.

4. Be worthy of a good conversation…

…I would stress the basic point that most conversations are bad, so your proper goal is to make them worse (so they can end) rather than better.”

—Tyler Cowan, “How to have a good conversation.” Marginal Revolution. September 23, 2018.

One theory, if you cut down on conversations you don’t want, you’ll have more you do want. Another theory, you’ll just have fewer conversations, but the overall quality of your conversations will go up.

So, win/win?

Interintellect

“Interintellect Salons are relaxed, evening-length, moderated discussions in video calls that anyone can join. 

During an ii Salon you will be given a short reading list and some pointers, and invited to take part in an open-ended, facilitated, friendly and diverse exchange about a specific topic.”

Interintellect

Illiberalism, Cancel Culture, Free Speech, and The Internet

“Bad faith is the condition of the modern internet, and shitposting is its lingua franca. On—yes—both sides. Look: A professional Twitter troll is president. Trolling won. Perhaps it’s time to acknowledge that despite their centrality, online platforms aren’t suited to the earnest exchange of big ideas.”

—Lili Loofbourow, “Illiberalism Isn’t to Blame for the Death of Good-Faith Debate.” Slate. July 12, 2020.