ChatGPT rolled out an update that I think makes AI a little easier to understand, especially if you don't care about memorizing model names or digging through complicated settings.

The basic idea: you can now more clearly choose between getting a quick answer and asking ChatGPT to spend more time thinking something through. Free users are also getting a new Think button for more complicated questions.

That might not sound like a huge deal, but it raises a really useful question:

When should we ask AI to think harder?

Not every task needs the same amount of effort. Here's a simple way to look at it.

🟢 Green: A normal response is probably enough

Use this for lower-stakes stuff like:

• Rewriting an email
• Brainstorming dinner ideas
• Summarizing notes
• Making a packing list

A decent first answer gets you most of the way there, and mistakes are pretty easy to spot and fix.

🟡 Yellow: Ask AI to think more carefully

This is for things like:

• Comparing several products
• Building a realistic schedule
• Planning a complicated project
• Weighing the pros and cons of a decision

These involve multiple moving pieces, so it helps to ask AI to slow down, consider the tradeoffs, and point out what info might be missing.

🔴 Red: Think, verify, and bring in a pro when needed

This includes:

• Financial decisions
• Medical questions
• Legal issues
• Anything involving personal safety

AI can be incredibly helpful for explaining unfamiliar terms, helping you prep questions, or showing you where to start.

But it shouldn't make the final call for you.

A recent Gallup survey found that about one in five Americans who sought financial guidance in the past year used AI. But only 3% of adults said they had a great deal of confidence in its financial expertise.

Honestly? That feels about right. AI can help us get better informed. That doesn't mean we should blindly trust it.

One prompt to try this week

Help me think through [describe your decision]. Separate the facts, assumptions and unknowns. Give me the strongest case for and against each option, identify what information is missing and list anything I should verify before deciding. Do not make the final decision for me.

The big takeaway

Being good at AI isn't just knowing how to get an answer.

It's knowing when the first answer is probably enough, when to ask for deeper thinking, and when your own judgment (or a qualified professional) needs to take over.

That's a way more useful skill than memorizing which model has the best benchmark score this week.

Chat with y'all again soon!

– Steve

Want to get comfortable using AI every day, minus the overwhelm? That's exactly what AI Unlocked is for: 10 short, hands-on modules in plain English.

This post originally went out to my email list on August 10, 2026.