How to Use ChatGPT as a Daily Journaling Partner - My One-Week Experiment

Includes Prompts, Setup Tips, and Key Takeaways from My First Week Journaling with ChatGPT

Jun 14, 2025

If last week’s post got you thinking, this one’s going to get you doing. We’re diving into one specific way to use ChatGPT in everyday life - and I’ll share the exact prompts I’ve been using to make it stick.

Turning ChatGPT into your non judgemental journaling partner

Taking journaling to a new level

I’ve found it difficult to stick to a journaling habit. Well actually I’ve found it pretty impossible.

I’ve tried using Ryan Holiday’s journaling prompt book. A page for every day of the year plus a number of prompts on each page to get you thinking and writing. I managed to keep that up for 2 days.

Then I had a short break.

Tried it again and then gave up.

To be honest, I was demoralised by fact that I had to leave loads of pages blank as I’d missed those days and I just wasn’t getting anything back.

It was boring.

I’ve tried the Day One App

This App is nicely laid out. You’re encouraged to post each day and having it on your phone its always there and it prompts you to add an entry. You can add pictures and locations and it looks and feels nice.

But it didn’t take long for the monthly payments to start bothering me. Every time I opened the app, I felt more frustrated - paying to use it, yet becoming increasingly tied to it. The more I wrote, the more trapped I felt, worried I’d lose everything if I ever stopped paying.

So I stopped.

And that has been the end of my journaling career - until this week

Ok ok. It’s only one week but let me explain what I’m up to here. The process is ridiculously simple.

I have a notebook. Yes! A real paper notebook with a nice pen.

The task is to write down your stream of consciousness for 5-10 mins.
That’s all. Write down everything and anything that comes into your head.
The trick is to not let your pen leave the paper.
You don’t really want to think about what you’re saying.
Repeat this one or twice a day.

Get it all out and down on that paper.

Let’s head over to ChatGPT - how to set it up…

The first time you do this, you’re going to need to do a little setting up.

We’re going to use ChatGPT’s “Projects”. These are areas where you can start or add chats with the project specifically set up for ChatGPT to respond in a certain way.

Start a new Project and label it “Journal”
Underneath the chat window you will find “Add files” and “Instructions”
Open “Instructions” and add how you would like ChatGPT to respond to your journaling - my prompt is set out below

The Journal Project are will look something like this.

Feel free to steal or adapt my journaling prompt below for applying to all chats within the Journal project you have now set up.

PROMPT to add to project instructions:

I’m uploading journal entries. Your role is to act as a professional life coach.

Step 1: Read the journal entry and bring the key themes and emotional undercurrents into the chat. Summarise briefly what you notice without judgment.

Step 2: Use your coaching expertise, the latest self-development techniques, and insights from our previous conversations to offer thoughtful support, ideas, or challenges where helpful.

Step 3: Ask me one question at a time — not a list — that will help me go deeper or move forward in a meaningful way. Wait for my answer before you continue.

You should draw on my past reflections, goals, concerns, and values.

Stay warm but direct. I want coaching, not coddling. Let’s get into the real stuff.

Priming the AI to respond in a certain way

In the first section of the prompt I’ve set out the role I want it to play. I’ve gone for professional life coach but you could have “motherly figure” or “drill sergeant” - have a play around and set it up in a way that will work with your personality and what you think will drive you.

Do you need someone to be harsh with you or a shoulder to cry on?!

Then I set out the prompt into three stages.

Stage 1 - This is about getting the journal entry ingested and summarised, so I can check that it’s been read and understood accurately
Stage 2 - This is about offering some guidance based on the personality you set up
Stage 3 - This is about challenging you to go further in your thinking with some useful questions based around your thoughts that day.

Notice that I asked for “one question at a time” - this is a key prompt technique that you can use again and again. Without this, ChatGPT will ask you a number of questions all at once and it can feel overwhelming to have to answer all at the same time.

One question at a time gives you much more scope to have a conversation and bounce ideas off each other.

Now you have your AI primed - let’s add some journaling

Once you’ve finished your ten mins of continual journaling with your pen and paper it’s time to crack open ChatGPT and a chat within the Journal Project.

Click the add button and select camera.

Take a separate picture of each of the pages of journal you wrote that day and an intro prompt such as:

Journal entry for Thursday 12th June 2025

That’s all you need. The Project Instructions will do the rest of the prompting for you from that point onwards.

Side note: ChatGPT is pretty incredible at reading my handwriting - better than me in fact. To be sure, make sure you write important words as clear as possible just to head off the risk of it getting the wrong end of the stick. (This week it did get confused by a Shearing Meeting and some sheep when it was actually a Steering Group Meeting)

So what will you get out of this?

I can only talk to my experience this week but just the act of getting those ideas down on a piece of paper helps me order my thoughts. I feel fresh and unburdened once I’m done with those ten mins.

And as a bonus, you get to interact with a non-judgemental partner and use the summary as a springboard to bounce around a few ideas.

Over time, ChatGPT has started spotting links between my journal entries across the week - and that’s where the real benefits are starting to emerge.

Today, for example, it suggested a brilliant strategy for dealing with doomscrolling.

I’ll share more on that in the coming weeks.

So what do you think? Will you give it a try?

Let us know in the comments if you’ve tried anything similar? How have you found it?

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