Using Day One to scratch that Timehop itch

Over the past few years I’ve tried to curtail my use of social media. I’ve unfollowed a ton of accounts on Instagram and Twitter, deleted my Facebook account, and mostly lurk in general. I’ve also deleted all of my old posts – I know that stuff is still searchable for Twitter if you are so inclined but at least by default it’s not hanging out there.

But I’m still a person who enjoys looking back at what I was doing and thinking retrospectively. When I was a heavier user of social, Timehop notifications were something I always looked forward to and got a lot of joy out of.

What I’ve done instead is committed to posting daily in Day One. I’ve been using the app for about 10 years now but have really leaned into it in the past 3 years. My daily posts don’t have to be anything super deep or insightful, but just document what’s going on in my life or what’s in my head. The app has a really neat daily prompt feature that you can enable that will either simply say “hey remember to post”, or even tee up a post idea for you to get started with. You can create templates and tag posts to help for future discoverability as well. I also have configured a monthly retrospective notification that reminds me to reflect on my job, relationship, family life and more.

Once you start writing daily, you become more mindful of the world around you. When I don’t have anything super important going on day-to-day my fallback daily post is typically a gratitude reflection. Spending even 5 minutes thinking about what happened that day that I’m grateful for brings me immediate peace and balance but it’s also beneficial when I review them years in the future. And obviously, since it’s private and only I can read the posts, I can cover way more ground that I ever could posting on social and reviewing in Timehop.

For every day that you have a post from the same day in the past, you can get a notification to review all of those posts. I really enjoy going back through simple moments as well as family vacations I’ve taken. I try to capture the little moments that stood out from those days and they bring me a lot of joy. As a parent, I know my time with my kids is so precious and being able to reflect on those as they grow up is priceless.

I think there’s still a place for social media in your life if you are doing it right, but these days it’s pretty rare that I want to go there first. Obviously, writing on your own website has a similar “yelling into the void” aspect that something like Twitter does, but I like the pace of blogging compared to something like Twitter for the most part. I also realize I just spent a few hundred words telling you that journaling can be beneficial, but if you’re like me and get tremendous value from “looking back”, a digital journaling service like Day One will bring tremendous value to your life.

Apple Music has betrayed its most loyal listeners

From Jason Snell at Macworld:

So this is where we are: Apple’s decision to put things that are not songs amid its collections of songs have made Apple Music’s curated playlists and algorithmic radio stations substantially worse. And at the same time, the Music app has proven utterly unable to help people who don’t want their music mixed in with promos and happy talk.

The way forward for Apple Music is simple: Turn off the ads and promos until your app is capable of letting us opt out from hearing them. But until then, if you insist on foisting this not-music on us, I curse you to an eternity of listening to nothing but the Kars for Kids jingle. You heard me.

I really hope we get the option to disable this type of content in stations and playlists. I haven’t encountered any of this so far but it’s a slippery slope to Apple Music becoming what Spotify is – an app focused on engagement instead of music.

Rediscovering the Mac

From Federico Viticci at MacStories:

The new MacBook Pro with M1 Max is an incredible machine that takes pride in being a computer built for people who want versatility. This computer has a clear identity; you can tell it was designed by people who love the Mac for people who had grown dissatisfied with the Mac over the past few years. This machine is a love letter to win back those users. Everything about the new MacBook Pro – from the screen and battery life to the keyboard and ports and its raw performance – is a testament to how fundamental Apple silicon is and will be for the future of Apple’s computers. If you’re a longtime Mac user, there’s never been a better time to fall in love with the Mac all over again than right now. Apple silicon is the perfect comeback story for Apple’s Mac lineup.

This is a great article, written by someone who has been “the iPad guy” for the past few years. I appreciate the way he walked through what he loves about the iPad and iPadOS and how the Mac gives him options to do things the way he wants to. There’s a lot of good links to tools he’s using and wishes for what the iPad could be if it adopted some of the things that make a Mac great so I recommend giving it a look even if you’re already a seasoned Mac user.

I recently upgraded from a 2018 Macbook Pro with it’s hot, battery sucking CPU, sub-par keyboard, lack of ports and touchbar to a new 16″ Macbook Pro and it has really rekindled my appreciation of the Mac as well. I have an iPad Pro that I use a lot around the house and like Viticci wish I could do even more with it. But at a certain point I think we have to accept the fact that letting each device class be true to itself is actually the best way to work in the Apple ecosystem.

Which Apple apps or services are truly great?

I was recently reading this article about how Apple’s services are often creaky, slow and feel half assed and it got me thinking: for any given app or service, what is the best in breed for that area? I’ll skip some smaller utilities and such, and focus more on the core apps and services.

Apple Maps

Do I use it? Sometimes
What is the best? Google Maps
Why? The gap has closed significantly, with Apple Maps actually being better in many ways (turn by turn UI, overall UX, speed), but still lagging in search results and POI info like how busy the location is, and the list functionality is not on par with what you can do with Google. Also, bike mapping & overall global rollout is lagging. Ask me again in a year or two, though. Apple is catching up, fast.


Do I use it? Sometimes. Almost all of the time on mobile, rarely on desktop
What is the best? Google Chrome on desktop, Safari on iOS (only because of extensions)
Why? I want to like Safari, I really do. But it just feels so fiddly sometimes. Questionable UX decisions on desktop and mobile, tabs are flushed from memory too frequently, the extension model (downloading an app just to have an extension), relatively slow development / lack of focus on modern web app features all make it hard to really love it. I use Safari on iOS only because it’s the only way to use extensions on those platforms. I’ve been impressed with the recent investment in improving Webkit so I’m hopeful the apps will get further spit and polish so I can stop using Chrome or Brave while at work. Philosophically, I don’t want to support a monolithic rendering engine world and I do appreciate Apple’s stance on privacy.


Do I use it? Yes
What is the best? Unclear, it depends
Why? Notes is great as a simple note taking app with a few sneaky-pro features like sharing, locked notes and tagging. It does everything I need, and they tend to improve it incrementally over time. There are small details I hope to see improved like rich links when pasting in URLs, more themeing options and linking notes for more power-user types but I’m really happy with Notes.


Do I use it? Yes on iOS/iPad, no on desktop
What is the best? Depends – Gmail app, Spark, Outlook
Why? Mail is simple and does what I need but it’s missing nearly every modern mail client feature. That’s probably okay for most people and I’ve never really cared enough to stick with any of the 3rd party clients. I use Fastmail for my personal email and Gmail for work, so I tend to use the stock app on my devices and the webapps on my laptop.


Do I use it? No
What is the best? Fantastical
Why? Calendar is fine, but doesn’t do much beyond the basics. Fantastical isn’t cheap but even the free version looks and functions better than Apple’s Calendar app. Better integration with video calls and more intuitive calendar views on mobile would make them a better match for Fantastical but right now it’s not really close. But for non-business users who only have a few calendar events here or there it’s really a great app.


Do I use it? Yes
What is the best? Probably Whatsapp
Why? Messages is pretty solid but I think the gold standard is Whatsapp. It’s a top 3 or so service though and I think people are generally happy with the features and functionality. I wish they’d adopt RCS, make group texting a bit more intuitive


Do I use it? No
What is the best? Things
Why? Reminders is fine for most people and it has been improving over time. Lots of new features have come out in the past few years to make is a good option for many people (shared lists, tagging, smart views and more). I use Things but that’s mostly because I have so many projects going on at work that I need to organize. If that wasn’t a concern I could see myself using Reminders. I really appreciate the fact that they use an open API that any app can plug into, and hope they continue to expand that over time. I also hope we see a defaults preference for Siri one day where when I say “Remind me to..” it would just dump the request into my app of choice.


Do I use it? 75% of the time
What is the best? The Kindle app offers a better ecosystem but Books is a better app.
Why? This one is complicated. Books is a better app in most ways. It feels good to use, is fast, has lots of neat features like reading goals and has a generally good UX. The Kindle app feels clunkier but boasts a better ecosystem. It also struggles with IAP due to Apple’s rules. I tend to look for the best deal on eBooks and all things being equal, will choose Books.


Do I use it? Sometimes
What is the best? Google Photos
Why? I use photos as my defacto library and use iCloud Photo Sync along with a few shared albums to send photos of my kids to family, but tend to use Google Photos as the front end as it’s faster, has more layout options, the slideshows/memories features are better and sharing is cross platform. Photos is a really great service on both platforms, I just think Google Photos is one of Google’s best products.


Do I use it? Yes
What is the best? Zoom
Why? Zoom is cross platform. I know FaceTime has the basic web link functionality now, but until they release a full fledged app and more filtering options, I think Zoom is the best for both professional and personal use.


Do I use it? No
What is the best? Overcast, Pocket Casts and Castro are all better.
Why? The one thing I like about Apple’s podcasts app is the recommendation engine, so they score points there. It suggests one-off episodes you might like and that is super helpful for discovery. Overcast, Pocket Casts and Castro are all infinitely better from an organization, performance and UX perspective, though. This is one app that I feel like is getting slightly worse over time and unfortunately they’re letting Spotify take over as a result.


Do I use it? Yes, mainly via Control Center on iOS
What is the best? Home
Why? Fortunately, the Home app is mostly a frontend for the HomeKit APIs so there are other apps that can do most of the things other than Control Center integration. I’m hopeful we see that area open up to 3rd party developers so I could use Home or HomeWidget more frequently. Both of those apps have better, more customizable UIs and allow you to prioritize info the way that you prefer for your home.


Do I use it? Yes
What is the best? Apple Music
Why? This one might rankle a few feathers but for me, Apple Music is the best but only barely. I’ve written about this in the past, but the album-focused nature of Music along with the APIs that allow amazing apps like Albums, Marvis Pro and Soor to exist means it’s the best for me. Add to that the great but flawed control center integration and controlling music in my home is easier w/ Apple Music and Sonos / HomePods. However, Music is slow, kind of poorly laid out, and is super creaky from decades of tech debt from the old iTunes store. I don’t know how you fix this other than a total rewrite on the Mac.


Do I use it? Yes
What is the best? Peloton? Depends, but I think this app is really good.
Why? I use the Fitness service from time to time and I think it’s likely their best service right now, especially given how relatively young it still is. The fitness app does a good job of tracking workouts, the videos and integration with the watch is great, and it motivates me to work out more frequently. We also subscribe to Peloton so I use that service for biking but otherwise it’s Fitness for me.


Do I use it? Yes
What is the best? Toss up between Flipboard, Google News and Apple News depending on your needs
Why? I wrote about this a while back, but I think people dunk on Apple News for some strange reasons. I really like the audio stories and magazines portions of the “plus” service, and the actual news feed does a good job of learning what type of stuff you read and offering up similar topics from time to time. My biggest complaints are the browsing experience for magazines and audio stories is kind of clunky, it’s hard to organize topics you follow, the Mac app isn’t great, and I wish you weren’t so locked into the app for reading stories but could instead bounce out to the webpage when possible. Flipboard and Google News are also great services, and I use those as well.


Do I use it? Yes
What is the best? It’s kind of a category of it’s own…
Why? There’s a lot to love and a lot to hate about this app. I love the ‘up next’ queue but unfortunately you’re at the whim of services and apps on if that’s integrated. But it’s nice having a way to quickly add shows or movies to my queue from the universal search UI. I wish there were a dedicated widget just for that purpose. Being able to be notified when new shows, movies or sporting events are happening is pretty awesome. The app itself is kind of a mess. It’s about a dozen or so infinitely side-scrolling lists that don’t make a ton of sense when browsing. It’d be cool to see the APIs for “up next” to be opened up so we could see some 3rd party clients take a stab at it, and I hope Netflix and other major services use the queue in the future.

Arcade / Game Center

Do I use it? Yes
What is the best? No real competition here
Why? It’s the best because nothing else really does what they’re doing. However, the fact that the Arcade apps are tucked inside of a tab on the App store is kind of strange. What I’d love to see is a standalone app that has special parental controls that allow you to freely download any game with certain ratings so I could essentially hand my kids an iPad, have them open up the Arcade app, and they can play whatever they want as long as it’s within a certain age range. I’d also love to see Arcades-game-specific data management rules. For instance, any game that hasn’t been played in x number of days could be offloaded to save space. In addition, the app could have better integration with Game Center, which could show more info about games your friends are playing, achievements you’ve unlocked, etc. Apple Arcade is actually a great service that I’ve grown to appreciate as my kids have gotten older and can play more of the offerings but the way to get to them is super clunky. So this one is tricky, much like the TV app. Nobody else does it so they’re technically “the best”, but I don’t feel like they’re doing that great of a job, either.

Wrapping up

So I think my conclusion is in line with the linked article from Benjamin Mayo. Apple’s apps and services are fine, with a few really solid showings for that 80% of users they’re trying to satisfy. However, many of my complaints aren’t about lack of functionality. It’s more about bad UX, slow interfaces or creaky tech debt. For a company that sweats every millimeter on the hardware side, I expect more on the software side. If they can’t or won’t address those concerns I hope they at least move down a path of adding more APIs that allow 3rd parties to address those needs. Apple doesn’t need to build every app or service that I use, but when they have a unique position that they’ve created and then don’t deliver, that’s a problem.

My worry is that all of the EU and US regulation that seems to be gaining traction is going to force the company to take their eyes off of the ball even further over the coming years and users of iOS and Android are going to see limited innovation as engineers on those platform scurry to build experiences that match the new laws coming out.

Albums 4.4 Released

Albums 4.4 was released this week, and it’s another feature-packed one. The 2 biggest additions for me is the ability to rate songs from within the app and the history import. The import in particular is awesome, as it gives the app the ability to build up a list of albums you have played but aren’t in your library as well as build up a historical “top albums played” in years prior to you using the app. As you may know, the way Apple Music tracks plays is simply incrementing play counts by 1, so frequency of listens is hard to do without a custom database. Fortunately, Albums does just that, and now it can backfill previous album listens along with the way it already tracks listening frequency.

Over the past few years Albums has become one of my most-used apps and I’ve really enjoyed seeing all of the love and attention Adam Linder has put into the app. I wrote about this a little while ago, but for me the ability to work through albums and see stats on what I’ve listened to and when has really made Apple Music that much better of a service to me. I rediscover music I haven’t heard in a long time as well as get insight into my listening habits in a way I haven’t been able to in other apps/services.

Albums is free for most of the functionality, and a $0.99/mo subscription for all of the bells and whistles.

WWDC 2022 Wishlist

Almost every year, I post a list of things I hope that Apple announces this year from the software side. Here is last year’s list, and I’ll be porting over a ton of the wishes from last year once again with the knowledge that they’re likely not going to happen this time, either. Without further delay, my top 40 requests:

iOS / iPadOS

  • Improve notifications by adding a notification history, easier actions and smarter prioritization. Clearing a notification should clear the badge.
  • Allow users to have more control over blocking images in email. For example, people in my contacts should be exempt.
  • Allow 3rd party rendering engines for web browsers. I want to see Chrome and Firefox push Apple to make Safari better.  Barring that, what about extensions in 3rd party browsers?
  • Find a way to manage spam texts and calls. They mostly fixed calls with the “Silence Unknown Callers”, but texts are still a big issue. It’s become really bad in the past year and I feel like Apple isn’t even trying here.
  • Allow apps to integrate with control center. Could you imagine all of the amazing Shortcuts and app actions you could see there if Apple provided an API for it?
  • “Tracker blocker” API similar to content blockers. We should have something like little snitch for iOS.
  • Better grouping options for Airplay2 devices. I have a ton of speakers & TVs and scrolling through that list is unwieldy. 
  • Allow me to set more defaults for reminders, maps, notes, etc.
  • Photos widget: I hate the change to the music-driven slideshow. I’ve replaced the widget with a Google Photos one.


  • External monitor support on iPadOS. Like, REAL external support. Maybe you could run more than just 2 apps at a time in this setup?
  • Make use of the “status bar” on iPadOS. Notification icons? Menubar options?
  • Global keyboard shortcuts – preferably user-configurable. I’d love to wire up Shortcuts to keyboard commands.
  • Make a better Lock Screen that rolls in notification updates as well as possibly widgets.
  • Key repeat settings for iPadOS. I hate how long it takes to backspace through things.
  • Better multitasking on iPadOS. What they did last year was an improvement to be sure, but I hope to see further refinements in this area to make it easier to jump between apps.


  • Improve the Siri watch face. I like the idea of cards popping up but I wonder if it’d make more sense to just have a type of complication you can show on ANY face to be a Siri suggestion?
  • It’s time for a stand-alone watch with apps to match. Expand on the family setup mode from a few years ago.

Apple Music

  • SPEED. Make everything from search to loading to scrolling on the Mac faster. It’s by far my biggest complaint about the service.
  • Collaborative playlists
  • Allow widgets to do some simple actions like play/pause of audio.
  • Better play count sync between devices. This seems to be super inconsistent and makes smart playlists hard to rely on
  • Allow users to create smart playlists on iOS devices
  • Genius playlists. I love the “daily mix” feature that Spotify has, and the radio station Apple provides is very good. However, I’d love to see it segmented out to multiple genres based on my history/taste.
  • Fix UX issues (better playlist grouping options, more condensed playlist list view, fewer items behind swipes/3 dots)

Apple News

  • Auto mark as read after finishing bookmarked News article
  • Improve the queue for audio stories so that it’s easier to bulk manage and triage the list of audio stories.


  • Siri should handle more commands without an internet connection when possible. Last year was a huge improvement but there’s a long way to go.
  • More robust Shortcuts actions for media playback at home. I’d love a shortcut that could adjust my home speakers volume to a set level and play a playlist on all of the speakers.
  • Siri needs “continued conversations” on all platforms like Alexa and Assistant.
  • Similarly, Siri needs to be able to combine commands “turn on the lights AND set a timer for 30 minutes”.


  • A redesigned Home app that’s a bit more useful. Better automations, easier to navigate and more information dense.
  • Timers set on one HomePod should be controllable from any HomePod as well as notify all HomePods if the timer isn’t turned off at the source.
  • Allow me to create “named groups” of speakers to start music to. Currently it’s limited to floors or rooms, which can be a bit tedious to invoke via Siri.


  • Rethink the tab groups. Make them all viewable from the main tab bar similar to how Chrome handles theirs. Currently it’s tucked away in the sidebar or in the dropdown and harder to get to.
  • Allow content blockers to work across any webview.
  • Better tab persistence, especially on iPadOS. So much RAM, and tabs just feel flimsy.
  • PWA improvements to allow people to create PWAs for certain types of apps that don’t really need to go into the App Store. Would be great for the web community but also for their antitrust case.
  • Extension updates shouldn’t force me to restart my browser.


  • Selective sync. I don’t want to sync all of my personal documents to my work computer, but do want to stay logged into iCloud and leverage the cloud sync functionality.

How Apple could turn HomePod mini into a delightful and adorable smart display

From Parker Ortolani at 9to5Mac:

Apple’s home strategy has been all over the place, but the company appears to finally have a hit with the HomePod mini. Rumors have been floated about Apple making a HomePod with a display, but word on the street is that the product being tested looks a lot like an iPad mounted to a speaker. Instead of making a Frankenstein product very similar to Google and Amazon’s products, Apple should take the blueprint it’s laid out with HomePod mini and use it as a basis for a unique ambient smart display.

Overall, an interesting take on what a HomePod Mini with a display could look like. From my perspective, I don’t know if it would really move the needle as I’d prefer something to replace what we have in our kitchen right now – a Nest Hub that can display family photos and still do the basic timer / music functions. I briefly touched on this a while back, mentioning something like a “HomePod Video” would be a game-changer for me.

Google Now, Glass, & Wear — The future we lost by making watches miniature phones

From Abner Li, 9to5Google:

What could have been starts with Google Now, a proactive feed that showed the weather, upcoming calendar events, birthdays, commute and travel information, package alerts, movies/concerts you might like, nearby events/places/restaurants, news updates, and much more, including information from third-party apps.

All this was displayed via a powerful card metaphor that showed just the relevant pieces of information. Users had one feed accessible to the left of the main Android homescreen or quickly launched by swiping up from the home button to keep track of their day and see what was next.

You didn’t have to jump into different apps to see upcoming flight details, check email to see when a package was arriving, or open a multitude of first and third-party apps to see your information. In those applications, you’re subjected to different layouts and have to learn different behaviors to access what is fundamentally your information.

Google Now was the high water mark of the “smart assistant” craze that started in the early teens. Since then, we’ve seen both smart home speakers and smart watches move toward more of a “question and answer” approach where you query your device for information or you’re pushed information about your tastes in a “feed” of some kind. I have a number of smart speakers in my house (and I’ve tried Siri, Google and Alexa) but I’ll be honest – I almost never use them becuase they’re a pain in the ass to use and they’re not very smart. At this point I bet 90% of my commands are comprised of adjusting volume, turning on/off a few lights and setting timers. Not exactly an intelligent assitant.

What I wish we saw more of was the Google Now approach – proactive data, notifications and reminders about things going on in your world. The watch is a great place for this because the interruptions can be unobtrusive, customizable and almost always with you. Apple has a Siri watch face that tries to accomplish what Google Now was going for but it feels like a ghost town – no real updates have been made in a long time.

I’m hopeful that increaesd competition in the watch field with Google giving their strategy a reboot will allow for more experimentation and pressure to make both platforms better digital assitants than some speaker could ever be.

Concept: Rethinking Safari in iOS 15 with the same core design principles and goals

From Parker Ortolani at 9to5Mac:

Apple’s newest Safari design in iOS 15 has been controversial, to say the least. It’s a complete overhaul of one of the iPhone’s most popular apps that follows entirely different design philosophies. Countless folks, including myself, have tried to come up with ways to “fix” the new design and make it more familiar and comfortable to use. This is my latest try. What I wanted to do was to follow the same principles and aim for the same goal. A mobile browser that’s easy to use in one hand and one that makes switching between sites on the fly a breeze.

This is very nicely done. This approach accomplishes a lot of what Apple says they’re trying to do with the new Safari on iOS but handles it in a manner that allows users to actually have an discoverable, enhanced experience.

Twitter is shutting down Fleets, its expiring tweets feature

From The Verge:

Twitter’s decision to axe Fleets is not just an admission that the feature didn’t work, but that the company still hasn’t figured out how to get people tweeting more. For years, Twitter has struggled to get new users to post regularly and not just consume other people’s tweets. Fleets was its shot at using Stories, the popular social media format invented by Snapchat and further popularized by Instagram, to lower the pressure around tweeting.

I think a better way to have created auto-expiring Tweets is to simply show them inline with some sort of designation that they are ephemeral. Even better, make expiring Tweets the default and find a way to allow users to “pin” tweets to their timeline.

I currently use Jumbo to auto-delete my Tweets after a few months and would love that feature to be baked in by default.