Everyone has one. A decision that's been sitting open for weeks. Whether to hire, which offer to take, whether to raise your prices, how to answer the hard email that keeps living in your drafts.
It's usually not that the decision is impossible. It's that you keep running the same loop in your head, hit the same two or three worries, and quietly set it back down. Thinking about it more hasn't helped, because you keep thinking about it the exact same way.
This is the use of AI that gets talked about the least and might be the most valuable. Not writing your emails or summarizing your PDFs, but helping you think. Used well, it's a patient second brain that asks the questions you'd skip on your own.
This week: how to use AI to work through a decision you've been avoiding, without handing over the decision itself.
🗞️ THIS WEEK IN AI
1. Claude's free version got a real upgrade
On June 30, Anthropic released Claude Sonnet 5 and made it the default for both free and paid users. The short version: the model most people get for free now performs close to the premium model Anthropic charged extra for just weeks ago, especially on reasoning and working through multi-step problems.
Why this matters: If you tried Claude a few months ago and found it just okay, the free version today is noticeably sharper at exactly the kind of think-through-a-problem work this issue is about. It costs nothing to test again.
2. ChatGPT got better at remembering what actually matters
OpenAI upgraded ChatGPT's memory so it updates on its own and does a better job holding onto the things that count, like your goals, your preferences, and the projects you're in the middle of. It also clears out stale or contradictory notes, so it stops "remembering" things that are no longer true. It's reaching Plus and Pro users in the US first, with free plans to follow.
Why this matters: A tool that remembers your situation gives more useful answers, because you stop re-explaining yourself every session. For decisions especially, that context is the difference between generic advice and advice that fits your actual life.
3. Most personal AI accounts are quietly doing work
A 2026 study from Harmonic Security found that across the major free AI tools, roughly 65% of activity on personal accounts is actually work, not personal use. A real chunk of that is "decision support," people talking through work choices with AI, and Claude got used for it more than ChatGPT did.
Why this matters: Using AI to think through work decisions is already normal, so you're not late to it. But if you're on a personal account, watch what you paste. Company specifics, client names, and anything confidential don't belong in a personal free tool.
🛠️ THIS WEEK'S TRICK
Talk a Stuck Decision Through With AI, Without Letting It Decide
You have a decision that keeps circling back and never resolves. The goal here isn't to let AI choose for you. It's to break the loop by getting the whole thing out of your head and onto the table where you can actually see it.
Step 1: Brain-dump the decision
Open a chat and just describe the situation the way you'd tell a friend. What you're deciding, what's making it hard, what you're afraid of. Messy and rambling is fine. You're not writing an essay, you're emptying your head.
Step 2: Run the thinking-partner prompt
Paste this into ChatGPT or Claude:
I'm trying to make a decision and I keep going in circles. Act as a thoughtful thinking partner, not a cheerleader.
The decision: [describe it in a sentence or two]
What's making it hard: [the worries, tradeoffs, or unknowns rattling around]
What matters most to me here: [money, time, stress, growth, family, whatever it actually is]
Help me by:
1. Playing back the real decision in one clear sentence, in case I'm actually deciding something different than I think.
2. Laying out my main options and the honest tradeoff of each.
3. Asking me 3 to 5 questions I haven't considered but should before I decide.
4. Naming any option I seem to be avoiding, and why that might be.
Do not tell me what to do yet. Help me see it clearly first.Step 3: Answer its questions honestly, then decide
The value is in step 3, not the first reply. Actually answer the questions it asks you, out loud or in the chat. That's where the thing you've been dodging usually surfaces. Then make the call, as a person, with a clearer picture than you had ten minutes ago.
What this works best for:
Decisions you've been sitting on for weeks
Choices where your gut and your spreadsheet disagree
Any "should I or shouldn't I" that keeps hijacking your attention
Pro tip: once you're leaning one way, ask it to "now make the strongest case for the option I'm leaning against." The point isn't to obey it. It's to finally hear the argument you've been avoiding.
🔧 TOOL OF THE WEEK
Claude — https://claude.ai
Claude is a general AI assistant from Anthropic that's especially good at the back-and-forth this issue is about: talking through a problem, weighing options, and asking real follow-up questions instead of just firing back an answer. Independent usage data this year found people reach for Claude for decision support more than any other major assistant.
With the free Sonnet 5 upgrade from this week's news, the version you get at no cost is now genuinely strong at this. If you already live in ChatGPT, the trick above works there too. The tool matters less than the habit.
Price: Free plan is enough for regular thinking-partner use. Paid plans start around $20/month for higher limits and priority access to the strongest models.
Best for: Anyone who wants a patient sounding board for decisions, plans, and the messy first draft of a thought.
Worth trying? Yes. It costs nothing to open a chat and talk through the decision you've been avoiding.
💡 PROMPT OF THE WEEK
Use this when you've basically decided and want a quick gut-check before you commit.
I've mostly decided to [your decision]. Before I commit, be my honest second opinion.
1. What's the strongest reason this is the right call?
2. What's the most likely way I regret this in six months?
3. Is there a smaller or reversible version I could try first instead of going all in?
Keep it short and direct. I don't need reassurance, I need clear eyes.Tip: if the "regret in six months" answer lands hard, that's worth sitting with for a day before you commit.
👋 THAT'S A WRAP
Most decisions don't stay stuck because they're genuinely impossible. They stay stuck because we keep circling them the same way. A thinking partner breaks the loop by asking the questions you'd skip and pointing at the option you've been quietly avoiding.
This week, pick the one decision that's been following you around. Brain-dump it, run the prompt, and answer the questions it asks you honestly. You don't have to decide today. You just have to see it clearly, which is usually the part that's been missing.
If you know someone stuck on a big call right now, hiring, quitting, pricing, moving, forward this to them. Sometimes the most useful thing isn't advice. It's a better question.
See you next Friday.