Let's talk about journaling

Plus: What's next for Alexa, a big Windows update, and fresh iPhone photo tricks.

  Jared Newman  |  September 27, 2023  | Read online

Hey folks, for this week's feature column, I'm pleased to introduce Jeremy Caplan, who writes the excellent Wonder Tools newsletter.

I last featured Jeremy's work in January ("9 ways to tame your email"), and I enjoyed his recent post on digital journaling so much that I wanted to publish it here as well. It's certainly inspired me to consider a digital journal myself. Take it away, Jeremy!

Why I use Day One for journaling

By Jeremy Caplan

Day One is the best simple, easy-to-use, free app for digital journaling. Read on for five of its most valuable features, along with its limitations and alternatives.

Get your journal printed as a book 📖

I like that Day One lets me order a physical book with my journal entries. I do it every two years or so. A paper book feels more substantial than a digital file, and I like Day One's print quality. Books are 5.5" by 8.5”—they start at $20 for 50 color pages—plus 10 cents per additional page. They’re capped at 400 pages.

Include audio and video 🎧🎥

In years past I used only text in my journals. Now I like the surprise of encountering a little audio or video snippet when I look back on something I may not have fully captured in words. (Day One transcribes the audio into text as well.)

  • I like that I can record directly into the app, or I can upload other recordings, like my children’s music performances. I like to record conversations with family members to preserve their thoughts and voices.
  • I appreciate being able to add photos along with these audio recordings. In addition to audio, I occasionally add video snippets.

Create multiple journals 📚

I like maintaining multiple journals so I can print just my personal journal and keep my work notes in a separate thread, with its own distinct template.

  • In addition to my primary personal journal, I keep a book diary, or a BOB (book of books). Each entry is about a recent read, with a few thoughts, quotes and pictures of key passages, photos or illustrations.
  • I have another journal about teaching, where I jot down observations, ideas, and adjustments for next time. It's helpful for incremental improvement.

Add to your journal with email or SMS 💬

Each journal gets a custom email address, so I can email a journal entry into Day One or forward an amusing email. Or I can text in a thought, quote or image.

Import social media automatically w/ IFTTT 🦄

You can connect Day One to online services like YouTube, Instapaper, Instagram, and Spotify with a tool called IFTTTRead more about why IFTTT is so useful.

  • Example: when I like a video on YouTube, IFTTT triggers an action to create a new Day One entry with that YouTube video in my resonance journal, where I collect online things I like to review, reflect on, or write about later.
  • Here are the IFTTT recipes I use for YouTubeSpotifyTwitter, and Instapaper. You can also create a Day One entry when you post to Facebook.

Additional features ➕

  • You can automatically add metadata to your journal entries to include your location, weather, the music playing on your laptop, and your step count.
  • You can password-protect your journal.
  • You can set up multiple reminders and prompts to nudge yourself to be consistent about writing.
  • You can export a nice-looking PDF to back up your journal or print one or more entries.


  • Stagnant product. Updates have been rare and minor in recent years, so the software hasn’t improved as much as it did in its early days.
  • No Windows version. Windows users can use Day One’s Web version, or an alternative app like Life Journal, which syncs with Day One, recommended by Rohit Kamat.
  • Weak built-in templates. There are a few templates built-in for starting journal entries, but they’re simple and haven’t improved much since 2019.
  • No Web sharing. An earlier version of Day One allowed me to share links to individual posts with family members. Now sharing means sending a PDF of a post or text. Given that Day One was acquired in 2021 by Automattic, which owns Wordpress.com and Tumblr, I’m surprised that the Web sharing capabilities are so weak and haven’t improved since the acquisition.
  • Limited design options. I’m happy with text, bullets, links, and photos. But if you like the fancier design options you have with Medium, Notion, or other new online services — for embedded content, for example— Day One isn’t quite there.
  • Book printing works only on iOS, not on Android, and not on Day One Mac.

Pricing 💰

Day One offers a robust free version, but I pay for the $35 annual subscription to benefit from the following premium features:

  • Multiple journals
  • Syncing across multiple devices
  • Multiple photos and videos per post
  • Voice recording and voice-to-text transcription
  • 25% book-printing discount


Craft isn’t a journaling app per se, but it’s terrifically designed for writing and it’s easy to create, organize and share entries to make a diary with it. Here’s an example of a travel journal template and a resulting travel diary.

Diarium is a simple journal app that works on Windows, Mac, Android, and iOS. It’s easy to use and costs less than $10 on each platform for lifetime pro access.

Diarium can automatically pull in your content from social & fitness platforms

Apple Journal was supposed to arrive with iOS 17, but has been delayed. Apple device users should keep an eye out for it.

Paper: I bought this 5-Minute Journal to support a daily paper writing habit. I like its hardcover form factor and appreciate that it has space to respond to three simple prompts each morning, though it’s a splurge at $25 compared with the $6 blank notebook I usually use to journal or sketch out ideas.

Not sure where to start with journaling? I've written a companion Medium piece on 9 distinct approaches to take.

Thanks again to Jeremy Caplan for this week's feature column! Check out his free Wonder Tools newsletter for more deep dives into the best productivity and creativity tools.

Need to know

What's next for Alexa: Amazon announced a bunch of new gadgets last week, along with new features coming to its Alexa voice assistant. Engadget has a good summary of everything, but here are the highlights:

  • The Echo Hub (pictured above) is a $180 smart home control panel designed for wall mounting.
  • The Fire TV Stick 4K and 4K Max are getting refreshed, as I mentioned in Cord Cutter Weekly.
  • Alexa's conversational skills are getting a generative AI overhaul, but not anytime soon. Expect a limited "preview" later this year and some kind of broader launch in 2024.
  • "Map View" will let you create a home floor plan for Alexa devices. If you're cool with Amazon having that info, it should make smart home management a bit easier.
  • The Eero Max 7 is extreme Wi-Fi router overkill, but hopefully it'll push down prices for other Eero systems, like my beloved Pro 6.
  • Bad news: Alexa's smoke and security alarm detection will require a subscription starting next year.
  • Amazon still thinks you'll wear glasses frames with Alexa in them.

A big Windows update: Microsoft is rolling out a new version of Windows 11 with only one feature that I truly care about: It finally brings back the "Never Combine" option for taskbar icons, so that each window can have its own text label. I previously used an app called Explorer Patcher for this purpose—one of several Windows 11 tweaks I've recommended—but have uninstalled it for now.

Of course, Microsoft is focusing more on the AI angle for this update, which includes a built-in chatbot called Copilot, invoked by pressing Win+C. You can use it to search for info or control Windows settings, but I've found it to be kind of sluggish.

Alongside the Windows updates, Microsoft also announced a second-gen Surface Laptop Studio, by far its fanciest laptop at $1,999, and a third-gen Surface Laptop Go, which is pricier than earlier versions at $799 but has better specs.

Tip of the moment

New iPhone photo tricks: I'm still digging into the iOS 17 update, which launched last week, but one thing that stands out already is how many neat photo- and camera-related features it includes. Here's a roundup:

  • Quick pics in Messages: To send a photo in Messages, you must now tap the + button, then select "Photos." But if you hold the + button instead, you'll jump directly to the photo picker.
  • Camera level: Head to Settings > Camera, then enable "Level." Keep the camera still, and a horizontal line will show whether your phone is level with the ground.
  • Crop with ease: Zoom in on any photo in your gallery, and you'll see a crop button in the top-right corner. It beats having to back out to the "Edit" menu first.
  • Create a contact poster: In the Contacts app, head to My Card > Contact Photo & Poster. From here you can set a full-screen image that contacts will see when you call them, assuming they also have iPhones. (But good luck trying to look as stylish as Apple's sample subjects.)
  • Make your own stickers: As before, you can remove backgrounds from photos by long-pressing any object within. Now, you can turn those subjects into iMessage stickers. After long-pressing, just hit "Add Sticker." You'll find the stickers in the Messages app by hitting + and selecting "Stickers."
  • Extended wallpapers: Want to use a photo on your lock screen, but the clock is in the way? Just pinch to zoom out, and a gradient pattern will fill in the space beyond the photo's borders. (Remember: You can add any photo as a wallpaper by hitting the Share button, then selecting "Use as Wallpaper.")

Note that Apple isn't pushing iOS 17 too aggressively yet, so if you want it now, you'll have to seek it out under Settings > General > Software Update.

Around the web

Spend wisely

I've had eyes on Anker's Soundcore Space A40 earbuds ever since writing about Bluetooth Multipoint a couple months ago. They're received solid reviews for their sound quality and noise cancellation, and Multipoint means they can toggle between two paired devices without any fiddling in Bluetooth menus.

Anyway, Newegg has them for $60 with promo code SSCW2543, down from a street price around $80 and beating Prime Day pricing. Plus you get a $5 Newegg gift card to go with it. The deal runs through the end of the day.

Other notable deals:

Thanks for your support!

One last thanks to Jeremy Caplan for this week's feature column on digital journaling. If you enjoyed it, check out his free Wonder Tools newsletter as well.

As a reminder, this week's newsletter is arriving a day later than usual. We'll be back to the regular Tuesday schedule next week. In the meantime, send your most pressing tech questions my way by replying to this email!

Until next week,

This has been Advisorator, written by Jared Newman and made possible by readers like you. Manage your subscription by clicking here, or reply to this email with "Unsubscribe " in the subject to cancel your membership.