Day One Frustrations

I dumped Day One two years ago for similar frustrations. Went with Diarly which has a much narrower feature set but it’s much cheaper and it works. I’m currently in the process of moving journals to Obsidian anyway, which is even cheaper… and removes one more app from my list.

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I have heard that Notability is good for journaling also.

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Out of curiosity, what don’t you like about Diarly? Was looking to migrate there as I’m cutting back my subscriptions. Day One on chopping block for me…

The entire app feels dated.

  • The layout of the list view of entries is a visual mess. That the headlines and text preview of entries that contain media get pushed to the right is just bad interface design. Why not right align the media previews?

  • Why does the iPad (esp. the 12.9") not show the journal list permanently?

  • Typography- and whitespace-wise the app is just noisy and distracting.

I do like the widgets, but are they worth the yearly high subscription price? :confused:
Pretty torn about it.

Good Notes is great for this too, I prefer it over Notability but they are both great alternatives to specific Diary apps.

Oh, I like Diarly! It’s just that I don’t want to silo my journal outside my Zettelkasten. I sometimes have beginnings of ideas in my journal that I would like to connect to my PKM, that’s why I’m bringing it to Obsidian. But otherwise, I would absolutely stay with the app.

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I have to say the team at Day One has been really helpful. I have been sending them screenshots, issues, on a regular basis for the last 5 days. A lot of has to do with the issues I face in syncing on Mac or iPad or iPhone. Some issues I had seem to be dependent on which device I start on. I have less issues when doing everything on the Mac (versus iOS). They escalated a few issues to their engineering team to see why some things were taking place. For all the complaining I did initially, I was happy to see that the customer support didn’t just “drop me” to the side. I am still continuing with Day One for the time being, I spent time looking at other apps but I wasn’t content with the experience. However, this all lead to some questions and exploration for myself. I was attempting to add a video (little bit larger than required), and I thought to myself. I can just add the iCloud link instead. Then…the inevitable happened.

  • Do you add the iCloud link for that large video? for all videos?
  • Do you add the video file link that goes to the Synology?

My journaling was for me, but now I also think of my family accessing it in the future. (I reached out to Day One and they mentioned they plan on having ‘shared journals’ as a feature in 2021). I think this might be a separate topic post. We have discussed leaving passwords for family members, but what about accessing journals. How many of us have family members who would have no idea how to access or what to do on a NAS for example.

Which brings back that age old question, journal on a specific app? or find something more open and general, but then you lose in features.

It’s a shame to read this. I’ve just jumped on board… especially as the podcast hosts swear by it…

I really like it so far!

Do you guys use/have any good templates? Trying so hard to get into journaling.

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I’m planning to switch from Day One for similar reasons to many - fewer subscriptions, simplification etc. I’d rather get good with a few apps than scratch the surface of lots.

I use DEVONthink and Craft, and I’m sure one of those could be a good alternative, if not a complete replacement. Although Day One is really good at what it does, I don’t really need all the features.

Of course, the issue comes down to moving existing data to another app, as is often the case. I experimented a bit with the Share and Export options in Day One, and found that the best result was sharing to DEVONthink. Unfortunately however the location and weather information didn’t export.

Sharing to Craft produced a document with just the photos in the original entry but no text. Going to Craft via markdown export preserved all the text, including location and weather, but didn’t include the photos. That said, I could re-add them manually from the folder of images that Day One exported along with the markdown text file.

Has anyone got a good alternative process to easily move exiting content from Day One to Craft or DEVONthink? I should add that I don’t include video or audio content. Just text/images. Worst case I suppose I could just create a PDF from Day One with all the historical data and just use either Craft or DEVONthink for new entries.

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I’ve been told Bear has a good Day One importer, and from Bear you can then export to Markdown.

Also, this script will supposedly migrate Day One entries to DevonThink.

I have not tried either option personally, but it’s on my “someday/maybe” list.

I am going opposite direction for now but keen to know more about the users’ experience on Day One.

At the moment, I am using Obsidian for my daily bullet journal. It works well and it obviously connected well to other points within Obsidian. This is no issue if this journaling is used by myself only. I am thinking of passing on my journal as a legacy for my family. They would have hard time operating Obsidian. Also I want a media rich journal that contains photos, Twitter quotes, videos, email clippings etc. There may be Obsidian plug-ins that enable that but it is going to be very messy

I want a neat solution as part of my digital asset (or legacy) that I can easily pass on to my family. I am hoping that I end up with a collection of 20-30 years of fond memories captured in the journal.

I tried using other apps including Journey, Diarly but none of them are as feature rich as Day One. I also try to use Goodnotes but again not as elegant

I am on the 7 day trial of Day one. I am hoping that users on this forum can share more experience (good or bad) and is it worth the premium subscription fee. Has this been raised every year?

I posted here a brief summary of how I export from Day One into DEVONThink and, on the Hazel forums, a more detailed description of the role of Hazel in that process.

The only disadvantage of that process is that Day One tags are not exported but you can overcome that by using hastags in Day One and then use the DT option to convert hashtags to tags on import. I did at one stage use Bear but find my current process much speedier and more reliable.

Talking of reliability, I have used Day One for seven years but, on several occasions, had horrendous problems with the Day One sync service. I eventually found that so unreliable (e.g., in not picking up minor corrections to a number of old entries and then stopping working altogether) that I’ve stopped using Day One sync and simply now create all entries on my Mac. If at any time in future I have to use my iPad to create entries I’ll work out at the time how to transfer those few entries to my Mac—even if it involves some rather crude cutting and pasting! I’m not unduly concerned about that as my Mac travels with me 99% of the time.

The beauty of having all diary entries in DT is the wonderful search facility (which I use on my diary entries several times every day), the ability to add photos without slowing down the app and, perhaps above all, the ability to script (fe.g., to replace Day One links—to other entries—with DT links).


I also expect my journal to be a legacy. And I have switched over to Obsidian from paper journals. I handle the rich media by transcluding those media into the journal files. Right now It’s by moving a copy of the photo or email into Obsidian as attachments and then embed a link into my journal.

I am exploring whether I can link directly to the picture file in the place I store my photos where the link will have the fully cataloged filename. In my case I use LightRoom for cataloging and I have the picture files themselves on our server. The filename embeds data about the picture and the whole dataset is well organized. A typical filename is RG002_iPhone8_2021-01-18_3712.JPG or RG002_iPhone13Pro_2021-10-31_4964 The RG is the resource group to with that picture belongs, in my case my personal digital images. I’m looking at symlinks as an option but not clear yet on the final choice.

For me the whole cloud nature and inbility to easily and simply get stuff out of Day one made it a non-starter for me.

obviously every person has a different need. The fact that it is a cloud service means that it is relatively easy to access or inherit for my non tech family

I don’t really have much family. In my case the legacy would end up being part of the Historical society and for that a more robust way to move the data from one system to another and a simple format that is likely to be usable decades in the future is far more important.

As much as I love Day One (or used to) it has become increasingly frustrating. Lately, I have been considering not syncing my journals on my iPhone/iPad and going only with the Mac. It takes a good 30GB of space on my phone. In a world where iPhone storage isn’t cheap (versus a computer), not to mention the sync issues. I wasted hours a few months ago because all 3 devices had different amounts of storage, but the same number of notes. Several times, I get broken images that I need to re-add. This has caused a problem because lately I am trying to offload my photos off my phone and direct to my NAS. I got so irritated that I don’t think I journaled since December.

maybe you can consider setting up as follow for the iPhone


Before enabling Optimize Device Storage, please verify your data is synced by checking the Server Dashboard. See here: How do I know if my data is synced?

Open Day One > Settings > Sync > _Storage _and choose either Optimize Device Storage or Download All Media.

_Please note ​that with the optimize device storage option enabled, full resolution media may not be included in the iCloud device backups. Only media that is stored locally. _

I have moved to DEVONthink. It’s goes with my theme of trying to simplify everything. However mainly I trust the encryption on DEVONthink more, and it is stored in iCloud rather than their servers.

I didn’t know DEVONThink had implemented their own server system to store files. Not going toget me to go back but interesting if accurate.

DEVONThink doesn’t offer that (would love it)–I think acertree just meant that DT went in the iCloud direction instead, not that they offer both options.