Migrate 100s pages of MS Word notes to Obsidian

What I’m trying to do

I am a new user of Obsidian and excited by the possibilities. I’ve played around with it and have watched tutorials. I would appreciate any guidance on how to be proceed with my specific use case, examples and questions below:

Requirement: By searching for tags, that only the relevant paragraphs (not the entire note) appear in search so I can copy search results to a new note and start writing a blog with the tag search results.


  1. Should I use daily notes or monthly/yearly (about 30 pages total annually)?
  2. How do I convert my current date format into one that Obsidian would recognize and treat as the note date? (I’m technical, so coding or process advice welcomed. I don’t know Python but could learn for this task, as a last resort).

I currently have single annual MS Word documents with semi-daily thoughts that look like this:

1/1/22 my thoughts for today #fun. Many sentences of random thoughts and rare brilliance. etc. Many sentences of random thoughts and rare brilliance. etc. Many sentences of random thoughts and rare brilliance. etc.
1/3/22 some bad #jokes 
1/4/22 many thoughts about my family and life, long paragraphs.

Thank you ~

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By default, search shows an excerpt of the block (paragraph, list item, heading) that contains the search match. Multiple matches in a single note are shown under a heading for the note. You can expand the results to show the whole block or collapse them to show only the note names. There’s a button to copy search results.

If you like your current year-long files, then use yearly notes (that would be too long for my taste, but I’m not you). You could add headings for the months and enable folding headings if you like. If yearly feels too big, break a year into months and see how it feels. If that still feels too big, or if you want to link to dates, break a month into days and see how it feels (you can link to dates in a longer file using block links, it’s just a bit more of a hassle).

(As you probably know, using monthly or yearly notes requires the Periodic Notes plugin if you want a button to take you to the current one).

If you use yearly notes you don’t need to worry about it.

I think you can choose your date format in settings, but you’ll want to at least change the slashes to something else. I think the default format is YYYY-MM-DD, which is a good international standard that sorts chronologically when sorted by name.

To convert, use search-replace in an app that supports regular expressions, or the Regex Find/Replace plugin (or grep, on the command line). Syntax can vary depending on the app, but these 3 in order should work in the plugin (assuming your dates are all in this millennium):

  1. Find ^(..?)/(..?)/(..) Replace 20$3-$1-$2
  2. Find ^(20..)-(.)-(..?) Replace $1-0$2-$3
  3. Find ^(20..-..)-(.) Replace $1-0$2
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thank you, all good suggestions

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