Thinking with AI
Not just asking it things. Actually thinking better.
There's a version of using AI where you type a question, get an answer, and move on. That's fine. It's useful the way a calculator is useful.
But there's another version. One where AI doesn't just answer your questions. It changes the quality of your questions. It helps you see things you couldn't see alone. It becomes a thinking partner that makes you sharper, not just faster.
Most people never get to the second version because nobody showed them it was possible.
The difference between asking and thinking
Asking mode
You give instructions. AI follows them. You need a draft, a summary, or a list. Transaction complete. Quality depends on how good your instructions are.
Thinking mode
You share a situation. AI helps you explore it. You're looking for clarity, not output. Quality depends on how willing you are to be surprised.
Five ways to think with AI
These are techniques that most people never try, but they produce the highest value.
This works because you're not asking AI to think FOR you. You're asking it to think ABOUT your thinking. It becomes a mirror that shows you your blind spots. The key is the brain dump. Don't clean up your thoughts first.
"Here's everything in my head about this project right now. It's messy. Don't try to organize it yet. Just read it and tell me: what am I not seeing? What assumptions am I making that I haven't questioned? What's the weakest part of my thinking?"
The meta-skill: knowing when to stop
There's a trap in thinking with AI. It's comfortable. The conversation keeps going. You feel productive. But at some point, more thinking isn't what you need. Doing is what you need.
Rule: After 3-4 rounds of back-and-forth, ask yourself: do I know enough to act? If yes, close the tab and act.
What changes when you think with AI regularly
People who use AI primarily for output get faster. People who use AI primarily for thinking get smarter.
The practice of externalizing your thinking, having it reflected back, and defending it against challenges makes your thinking cleaner. The AI is a training partner. The muscle you're building is yours.
Combining thinking with systems
Something to try today
Pick a decision you're currently facing. Something real. Open Claude. Don't ask it to decide. Instead, type:
"I'm trying to decide [your situation]. I'm leaning toward [your current instinct]. Before I commit, help me think through this. What am I probably not considering? What's the strongest argument against my instinct? And what question should I be asking that I haven't asked yet?"
Have the conversation. Go 3-4 rounds. Then close the tab and make your decision. Notice how different that feels from just asking "what should I do?"
Where to go from here
One more thing
The most underrated use of AI is generating clarity.
Most people are drowning in information and starving for thinking. AI can help with the information part, but it can also help with the thinking part (blind spots, objections, patterns, projections), and that's where the real leverage lives.
The free newsletter is where I explore this intersection every week. Not "here's how to generate more content with AI." How to think better, build better, and stay unmistakably human.