09/03/2026
We spend a lot of time asking AI to make creative work easier.
Maybe we should ask it to make things harder once in a while.
Instead of asking for another idea, another draft or another answer, try asking AI to challenge the one you already have.
Find the holes. Be the skeptical client. Make the strongest case against it. Ask the question you're hoping nobody asks.
Because sometimes the most useful creative partner isn't the one that agrees with you. It's the one that gives you something worth reacting to.
New in Trajectory: AI Is Better When It Pushes Back
We keep asking AI to make creative work easier. Sometimes what we really need is resistance.