How would that work? Sounds interesting.
Let us know; I’d consider downgrading to Pro if it works. I also have the Team plan, so I have plenty of options.
Also, though I can’t imagine how this would make a difference, could there be a difference in the PDF created by Goodnotes versus Apple Notes that would affect Claude’s transcription accuracy?
I finally gave this a try. I subscribe to Perplexity Pro, so I selected Claude Sonnet 4.5 and uploaded the image of my handwriting. I asked it to transcribe to markdown text and it did a perfect job.
I also compared it to what Apple Notes did when I selected text in the Note. Apple got the words right, but it didn’t do the markdown part, so Claude for the win!
1 Like
I had Opus 4.6 do it, just now, and the results were mixed. I believe the difference this time compared to the last (which made no sense at all) was instead of using an external OCR service to read the large journal, Claude converted the 67 pages to image files and transcribed them visually. It seemed to start well but get progressively worse as it went on.
This was the journal entry:
This is what Claude thought it was:
These are just Morning Pages I wrote in GoodNotes. I write them fast, so my handwriting is not great, but I don’t think this is usable.
Also of note: The usage for this task was 32% of my current session limit and 6% of my weekly usage limit.
You can now take that reasonable transcription and have Claude clean it up. Two passes with Claude should do it! 
I just had a revelation, confirmed by Claude. (Somehow, that sounds more theological than I intended! 
)
Historically, I have disliked markdown editors because I find the markdown syntax for citations and URLs distracting. Then it dawned on me: “Can I avoid the clutter by having Claude insert what I need?” Sure enough, it can. Below is an example generated completely by Claude. Note, none of the text is mine. That is not the point. The point is that Claude can create the references and links without me doing so as I write. I only need to add enough parenthetical information for Claude to find the information and create the footnotes and links. Now that is what I call saving both time and clutter. I think I am getting to like this whole AI thing.
From Rough Draft to Clean Markdown: An Example
Below is an example of how a raw draft in iA Writer might look, followed by what Claude would produce after an editorial pass. The draft uses plain-language breadcrumbs for citations and links. Claude converts them into properly formatted reference-style Markdown with footnotes and URLs collected at the bottom of the document.
NOTE: If you click on the gray boxes with the *** you’ll see the footnotes.
The Draft
The Christian leader must understand that suffering is not an interruption of the calling but a confirmation of it. As Bonhoeffer argued, discipleship that avoids suffering is no discipleship at all (cite Bonhoeffer, The Cost of Discipleship, chapter on suffering). The Apostle Paul understood this with complete clarity when he described his afflictions not as obstacles but as credentials (cite 2 Corinthians 11:23-28). Leaders in our schools would do well to revisit this passage frequently.
The tendency in modern evangelical leadership is to treat difficulty as a sign of misalignment rather than faithfulness. Tim Keller addressed this in his work on suffering (cite Keller, Walking with God through Pain and Suffering), and his arguments remain compelling. For a helpful overview of how Reformed theologians have historically understood the role of affliction in leadership, the Gospel Coalition published an excellent essay last year (link to Gospel Coalition article on suffering and leadership).
After Claude’s Editorial Pass
The Christian leader must understand that suffering is not an interruption of the calling but a confirmation of it. As Bonhoeffer argued, discipleship that avoids suffering is no discipleship at all.[1] The Apostle Paul understood this with complete clarity when he described his afflictions not as obstacles but as credentials.[2] Leaders in our schools would do well to revisit this passage frequently.
The tendency in modern evangelical leadership is to treat difficulty as a sign of misalignment rather than faithfulness. Tim Keller addressed this in his work on suffering,[3] and his arguments remain compelling. For a helpful overview of how Reformed theologians have historically understood the role of affliction in leadership, the Gospel Coalition published an excellent essay on the subject.
As always, you need to confirm accuracy but overall, I’m impressed.
How would you prompt Claude to clean it up?
The nature of those entries will present a challenge to AI because it would require inferring meaning and intent, but I took your image and told Claude: “Claude, clean this up correcting for typos, grammar, structure, paragraphs, etc. Give this to me in raw markdown.” Below is what I received. I have no idea if this is better or not, but that is essentially how I’d handled it.
Journal Entry — January 18 — 5:41 AM
Page Two
Not entirely bases, like a best plan. A lot of things just checking it — great — its notes, and I hope it is not to ever make, to customize this, but are using our streaming service. It could be valuable.
I am logging the time we watch in Letterboxd. I would say that I also like how we watched it as well as a life system for Patricia. I should also write up a natural synopsis in Day One.
I am still making my way through Extreme Ownership and can still try to hear, but it just represents how to capture it. Where I want to keep those notes, it will take more time. Like the system again, I would use Google Sheets. It is cloud-based, it is lightweight, it is there, it is everywhere. Anywhere I am, to this point I have controlled some data effectively, so I am extending to use Sheets. Stretching or becoming —
I would also like to do more polished reviews in Day One. I already have a “Palace of Everything” journal set up. Of thought. There is no exact goal or need for it. It is not a set of tasks, but add a Docs collection into that specific journal.
I think my handwriting may be too bad for this to work. This is my hand-written page actually says:
Claude’s rendering of my handwriting is too far apart from the original text to be useful to me.
That may be the case. Have you tried ChatGPT or Gemini?
Unfortunately, the PDFs are over 100mb, so Gemini (Pro) won’t take it, as it is too large. I did upload it to ChatGPT (free version) and it would accept the file, but it says I reached my data analysis limit and encouraged me to upgrade to a paid plan.
I think I may have to wait for the technology to improve before I try it again, which isn’t a big deal seeing as these are just Morning Pages journal entries from the past and I don’t urgently need them in Obsidian. I am only attempting it because I have on “On This Day” section in my daily note and it’s fun to see what I was thinking about on this specific day over the past 8 years I have been journaling.
1 Like
I just fed a PNG of your sample note into Gemini 3 and got the following plain text version in about 20 seconds:
01/18 - pagetwo - 5:41
…that actually seems like a solid plan. A list always gives clarification. If grouped into months and recompiled at the start of each month to accommodate films that are arriving on our streaming services, it could be valuable.
I am logging the films we watch in Letterboxd, which lets me note the day we watched it, as well as a star system for reviews. I should also be writing a review/synopsis in Day One.
I’m still moving through Experience Curating, and am still trying to figure out what experiences I want to capture and where I want to keep those notes. If I was making the author’s system my own, I would use Google Sheets. It’s cloud-based, it’s ubiquitous, it’s free, it’s not going anywhere. I am, to this point, not comfortable using spreadsheets, so I’m stretching to use Sheets. Stretching can be a good thing.
I would also like to toss more detailed reviews into Day One. I already have a “Reviews Of Everything” journal set up, though I’ve never added an entry to it. It is time. I need to set up a Drafts action into that specific journal.
Is it closer to the original?
1 Like
That is perfect! So, maybe if I convert my large PDFs to PNG files I could upload them to Gemini and get good results. Thank you!
Some general improvements I’d like to see. (Not every improvement is a fit for every app, some already have some of this, and the developers might have even better ideas):
- export full boards/canvases/notes as an image, not a PDF, and optimized for handwriting OCR.
- Handwriting improvement toggle in the third party apps.
- Export linked collections of boards/canvases as a unified file.
- Export metadata along with image to aid OCR/analysis by the model. This would be JSON or markdown that could be pasted in along with the image.
- Major fantasy: integrate with models and generate the OCRed outline right from the app! This would especially be nice when Apple’s Foundation Model framework becomes stronger, so it could all happen on device at the necessary quality.
1 Like
Update: Using the Apple Preview app split the PDF in half and uploaded it to Gemini, which was very accurate. I think this is the way forward for this project. Thanks for the suggestions.
1 Like
I prefer Claude for a number of tasks, but OCR and handwriting recognition is one place where Gemini really shines.
PS - I admire your dedication to Morning Pages! I have never been able to get them to stick …
1 Like
Looks like you have some freelance coding to do!
1 Like
That is good to know for my future reference as well.
Thanks for sharing your workflow. Like everyone else, I think it’s excellent.
I have a question from a slightly different angle. I’ve been trying to figure out if I’m more productive and retain more by writing with a fountain pen on paper or with an Apple Pencil on iPad.
Does anyone have any comments on that? In a typical day, I’ll do journal writing both by hand and on the computer, and I find that handwriting evokes a different level of insight and thought.
My question is specifically about the fountain pen and/or Apple Pencil. Given the opportunity, I’ll always go for the fountain pen. Just wondering what other people’s experiences have been.
*I wrote this using Wispr Flow edited by Claude $20 a month version
I love the idea of using a fountain pen, but I have not found them practical. I am always cleaning them and often have difficulty writing with them. Consequently, I have defaulted to a high-end mechanical pencil for analog work, though I often use the Apple Pencil on my iPad. I prefer the iPad in general because whatever I write is available on all of my devices. But there are times when a mechanical pencil with a Levenger notebook or a Field Notes notebook is helpful.
Dictated with Superwhisper.