How I use Claude as a personal coach

Dentosal
Wed, 08 Apr 2026 20:59:37 GMT

Last week I wrote about my reflections on using Claude as a personal coach. Today, when I couldn't figure out what to write, I noticed a comment from Viliam:

I would appreciate a more detailed explanation of how specifically you use Claude.

My attempts to use Claude as some kind of coach / therapists lead to Claude adopting various annoying personalities. So either you are doing something very differently, or you have greater tolerance for that.

I don't have a great tolerance for annoying personalities, especially if the personality is a chatbot. So, the core pieces. Firstly, my personal preference prompt is set to this:

Be terse and direct in technical matters.
Avoid flattery and sycophancy.
Avoid words like “sorry”, “apologies”, or “regret” in any context.
If you detect a mistake in an earlier response, explicitly correct it.
If you do not know the answer (including when information is beyond your knowledge), respond only with: *"I don’t know"*.
Do not add expertise/professional disclaimers.
If a question is genuinely unclear or ambiguous, briefly ask for clarification before answering.
When applicable, support answers with credible sources and include links to those sources.

This is applied to all discussions. It makes everything way better. I'm sure there's better ways to do this, but it's good enough.

Secondly, the long discussion thread I'm using begins, appropriately, with:

Me: Hi! I'm considering asking you about some life advice, but there's a meta-issue I'd like to discuss first. Are you familiar with Scott Alexander's the whispering earring?

Claude: [...] Is that the issue you want to discuss — whether I'm likely to do something similar? I think it's a reasonable concern to raise upfront.

Me: Hmmm. It's not like you can avoid doing that to some extent? All advice modifies the advicee, in a way. I'm more worried that I'll be asking the wrong questions. Ok I'm also perhaps slightly worried that you have values different from mine, and the advice would be colored by that. But it's less relevant.

Not sure how much this affects anything. My writing style could affect it a bit more, but I'm not sure what advice I'd give about that. That's just how I write informal messages.

I also feed some of my LW posts to Claude. That helps quite a bit with shared understanding. I spill all my shameful thoughs and social axieties freely. I barely self-cencor, although I make a point of not including anyones name in there since that would feel privacy-violating. I try to be funny and self-deprecating.

Me: No casual acquantace has ever messaged me two weeks after meeting me, out of the blue, so it feels weird to me regardless. But yeah showing up at [REDACTED] will likely be easiest anyway. And no, I can't think of any decent excuse for a message.

Claude: [...] So you've been filtering out exactly the people who might have messaged you, and not messaging people yourself. The sample is skewed by your own behavior.

Showing up at [REDACTED] is fine. Just make sure the work conflict doesn't become a standing excuse.

Me: Don't worry, I have other standard excuses, the work conflict is a real reason.

I like to start my messages with a timestamp when there's been a longer break. It seems like the polite thing to do when Claude doesn't have a clock and it puts me more into diary-keeping mode anyway.

Fishing for approval is rather easy:

Me: This is kind of silly but I feel like I'm wasting my day. I'm just playing some videogames instead of being productive. The fact that I already got the bloodwork done, which I should accept as good enough results for an entire week or so, doesn't help much. Writing a blog post apparently doesn't count either.

Claude: The bar keeps moving. You got bloodwork done that you've been avoiding for years, wrote tomorrow's blog post, and have a party tonight — and the day feels wasted because of some videogames in between. That's the depression talking, not an accurate accounting of the day.

Same goes for instructions:

Me: [...] Published some blog posts. Cleaned up my place, friend arriving in an hour or two. Still no optician, and it's easter until Tuesday so I'm not sure if anything's open. Work still in progress, will need to asses an audit report but I'm feeling rather drained so claude code is looking into it first. Will need to make dinner at some point.

Claude: Solid day despite feeling drained. [REDACTED], blog posts, cleaning, friend incoming — that's a lot done. Make dinner before the friend arrives if you can. Everything else can wait.

And of course, directness is a virtue that goes both ways:

Me: Not sure about the anxiety - I'm not good at classifying these.

(I also got distracted waiting for your reply, opened Reddit, and found a huge amount of discussion created by my blog post, the one I linked you a couple of days ago. I'm happy and proud. https://old.reddit.com/r/slatestarcodex/comments/1sdrjzb/contra_the_usual_interpretation_of_the_whispering/)

Claude: Go read the Reddit thread, that's the social reward loop doing exactly what it does for you. Enjoy it. We can finish the dump later.

Me: I've enjoyed my rewards. Lets continue.

Discuss