Mac Power Users 478: Journaling with Day One

Last week we had a wild animal attack in the Californian’s back yard, and this week we had hippie talk from the Tennessean.

MPU is definitely all about flipping your expectations!

As for journaling with Day One…

I’ve been keeping a daily journal for the past couple of weeks, and Day One really is good at its job. My only wish is for more keyboard shortcuts on the iPad, but that’s true of just about every iPad app right now. The sync seems to be really fast and reliable so far, and I really like being able to drop pictures into entries a lot more than I thought I would.

I thought David and Stephen did a good job talking about the transition to subscription, which I don’t think anyone would argue that Day One did not handle well. But that’s mostly behind us now, and the question is: do they keep adding enough features or providing enough of a service to make a subscription worth the price?

I’m on the “grand-fathered” plan, which is plenty for me, although I’ll miss some of the newer features (light/dark mode, for sure) when they are subscription-only. Frankly, I’m not sure it’d be worth ~$3/month for me to use Day One (right now I’ve really only got one journal). That said, I’d hate to see Day One go away, because I don’t think there’s another app that qualifies as a “close second” by a long shot.


I’ve been using Drafts + Shortcuts + DEVONthink To Go for the past couple of years now for my journaling. I have been able to get quite a bit of the metadata stuff working in conjunction with Shortcuts, so there isn’t anything I need from Day One for my use case (though I won’t fault anyone for using it).

This reminds me: I need to go write this up so I can share it. I’ll post it here when I get it done.


@MacSparky mentioned the Field Notes notebooks he carries in his pocket falling apart. I ran into the same problem, my solution was to switch to the Field Notes Expedition. It’s far, far more durable than the kraft paper they use in their regular notebooks.

One note of caution though: David mentioned tearing pages out and giving them to people. The paper in the Expedition is durable enough that wouldn’t be an option.

What is this business about Hippie stuff. I cringe each time I hear it. I think 1960’s … I was adult alive so I carry images from then.

Nobody has accused me of being up to date. What is the current definition and why the seeming embarrassment?

1 Like

Great episode. I’m really looking forward to the third installment of the journaling trilogy on Focused.

I really enjoyed this episode, I’m just happy to see other dudes who journal. I honestly didn’t start sooner because it felt to “girly” and not “MAN” enough. I used to work with other guys who would laugh at other men who kept a journal. I’ve since seen the light and the only thing I regret is not starting sooner.

I’m the type who rather use something simple and futureproof so count me out of Day One. I’ve seen far too many companies disappear and my biggest fear is losing all the notes I’ve collected. I do an average of 10k words a week and it’s a tool that I’ve come to depend on for my business.

I even tried to use TextEdit because it’s built in and the RTF format won’t be going away anytime soon. I had to stop using it because for some reason Spotlight or Windows Search can’t read an RTF file if it has images in it. It’s the craziest thing ever. One single image and Spotlight says it never existed.

So I end up using Bear Notes and exporting to PDF because Spotlight has no issue reading and indexing those.

I’ve also developed a way for me to link my notes to other notes in a future-proof way, as long as you have a way to search text it will always work. It also allows me to link things not in my notes like files on my computer just by putting a timestamp in the “comments” in the get info on MacOS files. If I need to refer back to a point in my journal I say “search for… whatever the time stamp is” and it not only takes me to that entry but also the exact spot in that entry. This has been so vital for me in my business as I test things out and need to refer back to the original test in my current week’s journal entry.

I’m very interested in @MacSparky’s current state of voice dictation. I’ve become quite comfortable dictating short emails and messages on my phone, and it occurs to me that I’m ready to take the next big step.

I don’t think this type of dictation is common, though it has become VERY routine for me; I am as comfortable and unthinking with it as I am writing in some other way. I was at a conference recently waiting for a meeting to start so I pulled out my phone and started reviewing email. I saw one that required an immediate response, so I tapped the microphone button on the keyboard, held the phone close to my mouth and started talking, like I have done a million times before. When was done, I saw a colleague look at me bewildered, as though I’d had cats jump out of my ears.

@ecophoscys Day One exports to PDF. Best of both worlds!

PS I thumb typed most of this message, but I dictated the last paragraph and this one.

@ecophoscys Out of curiosity, why did you write off Day One if you export to a PDF anyway? A portion of this show specifically addressed the ease of getting your information out of Day One…either if they shut down or on a regular basis.

Seems like you’re cutting yourself off from an app with great functionality, but the example you cite is supported by that app?

How do you handle location data with your setup? That’s one of the things I really like about day one; I use it as a location check in for myself. Candidly, that’s probably my primary use for it.

Loved it! The ‘Thoughts On’ diaries is a really cool idea.

I really enjoyed this episode - it’s clarified a lot of my thinking about journaling.

I’ve used Day One since around 2011 and am a semi-consistent with it. Their subscription model did make me question whether I’m using the correct tool - yet another subscription.

Also, very similar to @ecophoscys, the future-proof issue is my major concern. I want something that I know for sure will be available in 20 + years time.
I was about to go with this (inspired / copied from @nahumck -

  1. Write the journal entry in Drafts
  2. Have images ‘hosted’ in Dropbox
  3. Use Shortcuts to get the days details such as weather and location
  4. Save the Drafts entry as a PDF and store in folders within iCloud Drive
  5. Save a backup entry saved as a txt file in iCloud Drive

I really liked this set up - the end-game of having the PDF entry saved in a folder structure along with tags made a lot of sense to me. In 20 + years time, everything is where it should be.

To go all in on this I would have to export 1500 Day One entries into iCloud folders and give up the Day One features I can’t replicate elsewhere - this episode reminded me of those (end-to-end encryption is a big advantage Day One has). As @HobbyCollector points out, Day One is already future-proofed with the PDF export option.
So for now, I stick with Day One.

I guess the purpose of journaling is very individual - for me, it’s as much about clearing my mind as it is having an archive of entries to reflect on in years to come. So for that purpose, the tool actually isn’t where the value is, it’s the process of journaling which is. This episode taught me I was thinking too much how I journal rather than why I journal.

Thanks to @MacSparky and @ismh for a great episode.

Stephen Hackett’s idea to scan his Field Notes notebooks interested me. Instead of using a scanner though, I thought using ScannerPro or Office Lens might be quicker and does OCR (provided my writing is clean enough…).

Anyone have ideas/hacks on how to keep a Field Notes sized notebook open to the pages your photographing? Two pages at a time (left side, right side) are fine vs individual pages.

Thank you!

I manually trigger a shortcut which adds it. I’ll be posting about this soon, and it will have the shortcut available.

1 Like

The biggest reason I don’t use Day One is that they only allow 30 pictures per entry. That is not enough for me. I take a lot of screenshots for work along with other pictures and I can far out exceed 30 in one entry. My last entry was over 150 images with over 10k words, Day One can’t handle it.

Another reason is the price; Bear Notes is half of Day One.

1 Like

I wanted to share an issue and solution I just ran found with photos in Day One. I’ve been using an IFTTT to grab the latest photo from my camera roll and add it as an entry but it recently stopped working. After a long search for a solution I found out that Day One doesn’t support HEIC images.

I just upgraded from an iPhone 7 to an XR which uses HEIC as the default format. Turning off HEIC solved the Day One problem. I’m wondering though if there’s a way to still shoot HEIC and have a Siri Shortcut that will look for my latest photos, convert to JPG, create the Day One entry and delete the JPGs?

I’m not good enough at shortcuts to create one that will do this so if anyone has a suggestion on creating it or point me in the right direction I’d love to learn more.

Thanks for all the great feedback on this episode. As we finished the recording, I thought to myself, “Went way too hippy there.” Glad you got something out of it.


Going to try and get this written up at MacSparky this week.



Was talking about just this subject with a friend today. He’s all in on dragon and says it was never any good on the Mac compared with the PC version. He runs Windows in Parallels on his Mac just so he can use Dragon on Windows. He says he barely even types anymore – writes, edits and controls the PC all using Dragon!

It occurred to me that the first big hurdle a person needs to clear in using dictation is training one’s self to speak in complete sentences and paragraphs. Mostly we don’t do that when speaking; if you look at a transcript of actual spoken conversation, it’s a big load of run-on sentences and sentence fragments. So speaking in sentences and paragraphs is an unnatural act for most people. I believe I have trained myself to do that without conscious effort just by dictating emails and messages on the iPhone.

Also, I loved this column by Farhad Manjoo. Mind. Blown.


Greetings all,

I have yet to listen to this Podcast of discussion but I wanted to share how I am using the Day One app. I have never been an avid journal writer but when I do I thoroughly enjoy reading older posts.

After listening to a MPU episode where a guest had expressed his love of the Day One app and it’s features I started journaling more often; I already had the app. But, that practice became sporadic.

At this point in time, I use the app all the time. I started taking advantage of multiple journals. One of my headings is “ramblings of a girl on a permanent vacation”. I use this journal when I am feeling a bit philosophical. I started another listing when I lost a dear friend and needed to express that sorrow; writing down those thoughts helped me immensely.

Now, what brings me to the app daily is that I use it for my studies. I discovered it was useful for taking notes in my Spanish class. One journal contains cheat sheets so I have quick access to particular notes when needed. I also have a heading for questions so as I study I deposit my inquiries into that journal.

Often, while on a lunch date, I will whip out the phone and take quick photo within the Day One app; a picture tells it all. I am grandfathered into the cheaper subscription and definitely get my money’s worth. I really don’t worry about losing data and it syncs well between devices.

You might say, that I do love this app.


You win @colleenjuri. You win.