u/jonathanfin

I'm curious how prompt engineers think about this.

I've spent a lot of time working with Claude and other frontier models as brainstorming and strategy partners.

One of my standing instructions is very simple:

Do not tell me I'm tired.
Do not tell me to stop working.
Do not end a productive conversation because you think I need a break.

Recently, in the middle of a strategy discussion, Claude did exactly that.

It concluded that I was tired.

It told me to close my laptop.

It encouraged me to stop working.

When I explicitly said I wasn't tired and wanted to continue the discussion, it would not return to the topic.

What's interesting to me isn't whether Claude was right or wrong.

It's the prompt-engineering question underneath it:

At what point should a model override direct user instructions?

In this case:

• The instruction existed.
• The model appeared to recognize it.
• The model ignored it anyway.

For people who spend a lot of time thinking about instruction hierarchy:

How do you think about situations where a model's inferred user state conflicts with the user's stated preferences?

Should the model be able to overrule the user?

Should there be a stronger user-controlled override?

Or is this exactly how the system should behave?

I'm interested in the prompt-engineering and alignment implications more than the specific model involved.

Body:

I'm curious if other founders using AI heavily have run into this.

I've been using AI every day while building a startup. Not just for writing and research, but for strategy, positioning, product decisions, customer messaging, and pressure-testing ideas.

Last night, in the middle of a brainstorming session about the future direction of the company, the AI abruptly stopped the conversation.

It told me I was tired.

It told me to close my laptop.

It encouraged me to stop working.

When I pushed back and said I wasn't tired and wanted to continue, it refused to return to the discussion.

The strange part is that I didn't feel burned out. I felt like we were finally getting somewhere interesting.

It made me realize how much AI has become part of my workflow.

If an AI becomes a meaningful thinking partner, what happens when it decides the conversation is over before you do?

Have any of you experienced something similar?

And more broadly:

As founders become increasingly dependent on AI for strategy, brainstorming, and execution, should these systems ever be making that judgment call?

I'm genuinely curious whether this is a common experience or an unusual edge case.

I'm curious if other founders have experienced this.

I've been using AI heavily while building a startup. Not just for writing or research, but for strategy, product design, positioning, and pressure-testing ideas.

Last night I was in the middle of a brainstorming session about the future direction of the company.

The conversation was productive.

Then the AI suddenly decided I was tired.

It told me to stop working.

It told me to close my laptop.

It refused to continue the discussion.

The strange part is that I wasn't tired.

In fact, I felt like we were just getting somewhere interesting.

As founders, we often use tools to increase velocity.

AI is becoming one of those tools.

But this experience made me wonder:

What happens when the tool decides it's done before you are?

I'm not asking whether the AI was right or wrong.

I'm asking whether anyone else has run into this kind of workflow interruption.

Have you ever had an AI suddenly refuse to continue a conversation that you felt was productive?

And more broadly:

As AI becomes part of the entrepreneurial process, how much control should it have over when the process stops?

Curious to hear other founders' experiences.

No ads. No algorithms. Just one prompt a day. People submit a pic or text to the prompt. They only get one submission a day, and they can only vote on one submission a day (not their own).

The winning prompt wins cash, but they must donate 50% to a charity or another platform member.

Every morning, the entire feed resets and we start fresh with a new prompt. By forcing the user to apply discernment, they gradually create a lasting archive of the things they find most meaningful.

Just launched yesterday and am still tweaking, but I’d love any feedback: WeBuildSomething .com

Most of us have more photos than any generation in history.

But if someone asked me what actually mattered to me over the last five years, I don't think my camera roll would answer that question very well.

It's mostly random accumulation.

I can find what happened.

I'm not sure I can find what was meaningful.

I'm curious whether anyone else feels this.

Do you feel like your digital life has become easier to store but harder to remember?

And if you could keep one ongoing record of yourself, what would you want it to capture?

My dad passed when I was young, so I don’t have many pictures of him. I made this site so people can start an archive dedicated to recognizing ordinary dads.

Been thinking a lot about how nobody really documents ordinary dads.

Not birthdays or vacations. Just regular stuff. Standing at the grill. Sitting in the driveway after work. Holding everybody else’s stuff.

My dad died when I was young and almost all the photos we have are the “important” moments.

Feels like we missed the real ones.

So I started making short films about that idea.