“Each passing year converts some of this experience into automatic routine which we hardly note at all, the days and the weeks smooth themselves out in recollection to contentless units, and the years grow hollow and collapse.”

Perhaps this is what I am experiencing right now. Either way, everything feels like chaos.

I’ve probably gone a bit crazy over the last few months — I’ve purchased more than a few things for the summer and fall ahead. The list of things to touch one is growing, and now includes:

• A Wandrd Prvke 31L backpack (bought used from a friend, OK? OK?!)
• A Peak Design Roller Pro (I promise, it was on sale)
• An M5 11-inch iPad Pro (I sold off the old iPad Pro, and with the latest price increases, I basically got it for free).
• An Apple Watch Series 11 (my experiment with the Google FitBit Air had to pay off somehow, right?)

All in all, I have thoughts. I can’t touch on all of them today, but I’ll attempt to in the coming weeks.

I’ve also recently been dabbling in an Andy Matuschak’s Working Notes-styled writing project in Obsidian. It’s been a few weeks of now of near-daily evening writing, culminating in some reflections, some prayer, some observations of the world around me, and some questions I have for Future Josh to answer or ponder. It’s been a wonderful little experiment that has provided additional structure to my writing and thinking. Will it ever see the light of day? It depends. The papers are for me and likely shouldn’t be public material. But we’ll see. To write is to teach, so perhaps it’s best for someone to view it at some point.

For today, though, I wanted to discuss my experience adding a new Apple Watch to an iOS 27 beta phone, and why I likely won’t ever download a beta like this again.

I am no longer on the iOS 27 iPhone beta

See above. I traded in my original Apple Watch Ultra for a new Series 11 Apple Watch. Why now, ahead of a pending update in September? A few reasons:

1. The trade-in value for my Watch Ultra was still reasonable, and this saved me from losing that inevitable slide in trade-in price in September.
2. Apple conspicuously left the iPhone and Apple Watch off the list of price increases, likely suggesting higher prices are coming in September for both product lines.
3. I learned what I liked and didn’t like about my Watch Ultra with the Google FitBit Air experiment, which pointed me directly at the current Series 11 feature set.
4. Rumours are suggesting a minor Apple Watch update in September, so I am taking my chances on being satisfied over the summer rather than waiting for a mediocre update.

I excitedly walked into the Polo Park Apple Store yesterday, tried on the 46 mm Apple Watch, instantly fell in love with the thin and light size, and aptly traded in my Watch Ultra. It was a pretty smooth process all in all, one I would do again.

At least until I tried to fire up the Series 11 Watch and pair it with my iPhone. What a debacle.

I was never going to be able to avoid iOS 27 beta software. Once I came off the Siri AI waitlist, I was genuinely impressed — Siri AI made its way to home screen nearly instantly, and I was using new Siri for questions I had never, ever imagined I’d be able to ask it. What’s coming September (or later? Probably later.) will be genuinely exciting for billions of iPhone and iPad users.

But that beta software seems to have gotten in the way. As soon as I attempted the pairing process with the new Watch, everything ground to a halt. I was stuck on the fire-up screen on the Watch, with no way forward. I walked back to the Apple Store, where the Store staff immediately said it was because of the beta software. Online hadn’t suggested these sorts of problems, so I took their answer to be the “easy way out” and put the onus right back on me. Fair, I suppose. I still wasn’t happy.

All in all, I ended up having to downgrade from iOS 27. I had no idea how difficult it would be to revert to iOS 26. Downloading an IPSW file. Using the Option key to restore through Finder (you know you’re in deep trouble when you’re using the Option key in Finder). The whole nine yards.

I’m probably not going to be downloading beta software like this again. I could see waiting for public betas over the summer, but developer betas are officially off the table for my iPhone.

Mexico 2026

It took me ages, but I finally put together a photo gallery of our first family vacation. The Leica Q2 continues to be one of my favourite tangible treasures — it produces imagery effortlessly.

Quote of the Week

“It’s fun to say the perfect thing at the perfect time. The problem is that then you have to bend over and pick up the microphone. Conversations take more effort but tend to be worth it.”

— Seth Godin

Fresh Links Roundup

Here were a few things I shared from the past week. If you want to stay on top of the list throughout the week, don’t be afraid to subscribe via RSS.

• Lettera for Mac
• John Gruber on Om Malik
• Mode Designs’s Summer 2026 Update

Happy Sunday. I hope you have a wonderful week ahead.

P.S. — If you’d like to see this in your email inbox, please subscribe below. If you have trouble subscribing, shoot me an email, and I’ll get you on the list. Thanks for the consideration!

Being a father is easily the most rewarding role in the world. Early on, it’s a grind — sleep, poop, eat, sleep, poop, eat… it gets to you (and is far harder on mothers, to be sure). But that so quickly turns into new best friends you didn’t know you needed. I’m in this “new best friends” discovery phase right now. Where I thought it was fun to be a dad when my girls were newborns and infants, it pales in comparison to the joys of young childhood.

Fatherhood is the best. It is a responsibility. It requires you to die to yourself to serve others. But it is a wholehearted privilege in the most divine way possible.

I Returned the Google FitBit Air

I owned Google’s new FitBit Air for a total of 10 days. I had it for such a short period of time that I don’t have any proper photography to showcase the Air. Which is a shame, really — the Google FitBit Air was an excellent introduction to the Google ecosystem, one which I would like to see Apple flat-out rip-off at some point in the future. What the FitBit Air did, it did well. For me, it’s what it didn’t do well that had it on an airplane destined to be recycled.

I was expecting better inter-operability between Google Health and Apple Health, third-party apps, and third-party hardware. When I did my initial reading of the FitBit Air’s capabilities, there was an explicit direction that Google Health would in some way connect with Apple Health. Which, of course, is true — you can read a number of Apple Health data in Google Health. But you can’t read Google Health data in Apple Health. Writing to Apple Health was a no-go. Which meant sleep tracking and fitness tracking stayed in Google Health and went effectively no further.

This meant I couldn’t measure sleep scores in Bevel or workouts in the Peloton app, the two pieces of health and fitness software I rely on. The inability to write to these apps from the onset quickly became a death knell for my FitBit Air.

And I wouldn’t be surprised if my expectations were premature that Google will soon open up writing into Apple Health and better connectivity with apps like Bevel and Peloton. It even sounded like rumours had started to swirl that better compatibility was already being worked on. For those who are on the fence, perhaps some patience is warranted to see if these sorts of compatibilities ultimately see the light of day.

The last major blow was the poor connectivity with our Peloton Bike. We have an original Bike, which is now upwards of six or seven years old. The technology is by no means new, but I’m not willing to respond the $4,500 to update it. Our Apple Watches continue to connect wonderfully with the Bike, and can even grab data from the Bike and app to track progress in our heart rate zones and send the data to Bevel for further analysis. I had genuinely hoped the FitBit Air could take the place of the Watch, feeding heart rate data in during a ride, and feeding workout data into other health and fitness apps. In short, I was able to see the FitBit Air in the Bluetooth view, but could go no further. At no point did tracked-data feed into the Bike.

I have it on good authority that the connection does work better with new Bikes, such as the Bike+. For me, the lack of proper connectivity was the final straw.

The single biggest positive Google’s FitBit Air provided in the 10 days of ownership: I have a newfound appreciation for my original Apple Watch Ultra. I’ve even started to wear the Ultra for sleep tracking at night. The upcoming software support discontinuation for the original Watch Ultra all but guarantees I’m retiring this Watch in the coming months, but you can be sure I’m replacing it with another Apple Watch. The question is whether I upgrade now to a Series 11 (which doesn’t appear to have a lot new coming in Series 12) or wait for the bigger, chunkier Ultra Series 4 (which is said to have many large upgrades coming).

Overall, the Google FitBit Air experiment was a truly great experience. I learned I appreciate being able to tell the time and check the weather on my wrist more than I thought. I learned about some major disconnects between Apple’s and Google’s walled gardens. And I learned the Apple Watch has snuck into “must-have” device territory for me. That is a great 10-day experiment.

Quote of the Week

“Society grows great when old men plant trees whose shade they know they shall never sit in.”

— An old Greek proverb.

Fresh Links Roundup

Here were a few things I shared from the past week. If you want to stay on top of the list throughout the week, don’t be afraid to subscribe via RSS.

• Cohort Size Matters When Measuring Wealth Across Generations
• Learning On The Shop Floor
• Hold on to Your Hardware

Happy Sunday. I hope you have a wonderful week ahead.

P.S. — If you’d like to see this in your email inbox, please subscribe below. If you have trouble subscribing, shoot me an email, and I’ll get you on the list. Thanks for the consideration!

In a different life, I would have called myself a “product reviewer”. I never hit it like many incredible YouTubers now, but I paid for school with the earnings. It was a thing for me. And it resulted in a backlog of stuff — I reviewed everything from pens and paper to lunch bags to iPads. I have more bits and bobs than anyone should have.

You know what’s cool about that, though? I still, to this day, use a bunch of that gear. I use a 15-year-old 11-inch MacBook Air leather case to tote around this new 11-inch iPad Pro. I still use the Bellroy System Work briefcase. I still often pack this PowerCube when I head on a trip.

I thought it might be fun to revisit some of these old product reviews; to see how the products have held up over time, how the product fit into my life in the long-term, or whether I replaced the product with a new and improved option.

First up, my first ever product reviews for Tools & Toys.

The Hellbrand Leatherworks Field Notes Cover

Field Notes COLORS Editions were a thing, guys. They might actually still be a thing — I still get emails from Field Notes Brand with the latest limited edition releases. When I was first starting out, I found a niche inside the Field Notes club, and I wrote a lot about memo books, paper, and pens. This Field Notes cover was the first leather cover I ever purchased, and the first I ever reviewed.

Well, I no longer use Field Notes memo books to take notes — I now use a reMarkable Paper Pro Move. But you know who constantly find themselves drawing, writing, and sketching in the house? My daughters. I have a severe backlog of unused Field Notes memo books, and my daughters are slowly eating through them. And this Hellbrand cover continues to be practical.

How has it held up? It doesn’t look exactly the way it did when I first reviewed it in 2014, that’s for sure. Frankly, it looks better. I’ve bent it this way and that way to bring out character in the leather. It has a few nicks now, along with a few marker stains from the girls. But it looks spectacular.

Hellbrand Leatherworks doesn’t exist anymore. In fact, they seemed to disappear just a short period after I wrote this review. You can likely find an option on Etsy today, though I feel strongly you’d have a hard time finding this type of longevity. I can directly compare it now to the Bellroy Field Notes cover (the Bellroy option pales in comparison, specifically in terms of leather thickness) or the Traveller’s Notebook (which is a thicker, more beautiful leather and is the only leather I own that has held up better than the Hellbrand cover).

The lesson this Hellbrand Leatherworks Field Notes cover taught me: Buying something once can mean a 20-plus-year lifespan. Products can last a lifetime. Some purchases are literally heirloom quality. Never once has the Hellbrand cover let me down. Unfortunately, there aren’t too many options as good as the Hellbrand on the market today.

Quote of the Week

“Onetime choices—like buying a better mattress or enrolling in an automatic savings plan—are single actions that automate your future habits and deliver increasing returns over time.”

James Clear, Atomic Habits

Fresh Links Roundup

Here were a few things I shared from the past week. If you want to stay on top of the list throughout the week, don’t be afraid to subscribe via RSS.

• Seth Godin on Value Creation
• The Patient Cash Bucket: AI Winners Watchlist & Deployment Tracker
• Bay Street Titan and Astronaut Attempt to Hack Mortality
• A Short and Quick One-Week Look at Claude’s Fable 5

Happy Sunday. I hope you have a wonderful week ahead.

P.S. — If you’d like to see this in your email inbox, please subscribe below. If you have trouble subscribing, shoot me an email, and I’ll get you on the list. Thanks for the consideration!

In some ways, it reminds me of Ray Dalio’s machine discussions in Principles.

This extended “sabbatical” provided some time to ponder what The Sunday Edition has become and where I think it properly fits. Sunday Editions have a precise 24-hour lifespan. They are time-specific, context-specific, and can rarely capture a larger thought process. They are a fair bit easier to produce, mind you, and the barrier to entry (the barrier being my energy) is a fair bit lower than a longer, dedicated blog post.

I’ll probably need more than a few weeks to ponder this. Even after 12+ years of writing this blog, I still don’t know what I want it to be. I hope, above all else, this is a sign of maturity and changes in the seasons of life, and not an overall poor author.

The Idol of the Bucket List

I once attended a funeral for a well-known businessman. He was well-known for a reason — if you ventured through his store, you always left knowing you were taken care of, that you were served, and that you could return someday for your next need. In so many ways, this gentleman embodied small-town grace — always connecting and working through his customers into the greater community and beyond.

With each story told at his funeral, however, an over-arching theme emerged: Once those doors closed at the end of the workday, this business owner hit the road in the pursuit of making memories.

Few people would say this with a negative connotation. On its face, making memories and living a full, well-lived life paints a beautiful picture. Modern society tells us memories are the ultimate currency. We’re supposed to purchase flights, not things; to collect moments, not possessions; to live now, not tomorrow. That collection of memories wraps itself around the very fabric of our modern lives, and will be fiercely protected as unique and worth every investment.

You’ve likely heard “You don’t take your bank account with you” when you pass away. You know what else you don’t take with you? Your memories.

As soon as you take that last breath, that vast archive you’ve spent a lifetime building — major investments in time and money — vanish. Your memories cease, and at best live on in the lives of those you’ve invested in. Once they’ve passed on, your memories— their memories — are no more. In 100 years, effectively nobody will remember you.

The only thing you take across that final destination is your faith. You develop that faith here, through things seen and unseen, and you use that faith there when you stand before your Father in heaven.

There’s a trap here, to be sure. Where the last 20 years have produced this anti-possession, pro-minimalist approach to building a full life, we’ve converted our love of possessions into a love of experiences. Minimalism, meet experientialism. Making memories can become an idol just as easily as any individual possession or hoarding wealth. Our bucket lists become our own personal creeds, our own personal doctrines that we live by, swear by, and will die by.

In reality, experiences — just like possessions — make terrible gods. The high of a new experience is extraordinarily fleeting and leave you more hungry for an even better trip, an even better ride, and an even better high. These things cannot be the foundation of our lives; we cannot have goals to maximize our personal good vibes archive. This misses the point of why we were created. Our purpose is far greater: to serve He who created us and who created this Earth.

Quote of the Week

“When you sprint, you sprint hard. When you rest, you rest hard. The most successful people apply this same approach to life. They aren't grazing for hours. They sprint, then rest.”

— Sahil Bloom

In line with my current modus operanda, if I do say so myself.

Other Thoughts

I’ve been posting a few other pieces here and there, under their own dedicated titles so they are easier to find in the future (not just for SEO, to be clear; I’m having a hard time finding all the things I’ve written about on The Sunday Edition and need a better system.)

Bauhaus Clock for iPhone and iPad

The Bauhaus Clock app for iPhone and iPad is a beautifully crafted, premium time-telling tool that delights users with its meticulous attention to visual, haptic, and audio details.

Rules and Standards

Reflecting on a quote by baseball coach Tim Corbin, I’d argue that striving for higher standards and living by the spirit of a rule is far more valuable than rigidly obsessing over technicalities.

Use a Scaled Virtual Machine Resolution in Parallels and Enjoy the Speed

In which I explain that switching a Parallels virtual machine to a "Scaled" resolution drastically improves system performance and software usability.

The Google FitBit Air is My First-Ever Google Product

This is my first experience with a Google product. In this, I note that despite an enthusiastic pre-order, the unboxing, setup, and syncing experiences felt cheaper, more rigid, and less seamless than what I’m accustomed to in the Apple ecosystem.

Fresh Links Roundup

Here were a few things I shared from the past few weeks (months!, yeesh, it’s been awhile). If you want to stay on top of the list throughout the week, don’t be afraid to subscribe via RSS.

• Oliur's iPhone ProRAW Neutral Collection Presets
• Fun Illustration of MLB's Lack of Salary Cap
• Star Fox for Switch 2 Trailer
• Leveraging My Second Brain to Build a Chief of Staff (and Secretary)
• Bubbles Briefing

Happy Sunday. I hope you have a wonderful week ahead.

P.S. — If you’d like to see this in your email inbox, please subscribe below. If you have trouble subscribing, shoot me an email, and I’ll get you on the list. Thanks for the consideration!

I have never pre-ordered a product as fast as I pre-ordered the Google FitBit Air. No Apple product. No Bellroy product. No Harry Rosen product. I didn’t do any research. I saw the header image, noted it was a Whoop-competitor, and ordered. The fastest and most alluring pre-ordered product in my life is a Google product, and it happened to be the first Google product I’ve ever owned.

As a very heavily invested Apple customer, I quickly treasured the opportunity to compare the two tech behemoths. Each of these companies produce more than a product — they produce an experience, from the packaging and unboxing experience, through to the setup experience and the usage experience.

The Google FitBit Air is my first chance to compare this set of experiences. Its simple purpose (health and fitness tracking) combined with its accessible price tag (only $100 USD/$130 CAD) made for a perfect opportunity to dip my toe in the ocean.

I have some thoughts.

On Unboxing Experiences

My experience with Apple product unboxings ranges from those years of plastic shrink-wrapped boxes through to the current system with a pull tab or two. Familiarity helps to ensure I know what I’m looking for in a new Apple box, so I’m always looking for those pull tabs from the start.

I didn’t know how to handle a Google box. The FitBit Air comes in a tiny box. I flipped it around and over a few times looking for the pull tab but, oddly, didn’t find anything immediately obvious. After a few moments, I decided I’d try to tear the box gently open. I haven’t torn an Apple box in years. (I did ultimately find the tab and kind of slapped my head for missing it.)

Inside, the FitBit Air wristband was wrapped around a kraft coloured holder in the box. Various parts of the FitBit were wrapped in a translucent wrapping, very akin to the wrapping around chargers and cables inside Apple boxes.

Documentation was in the box as well — a thick notebook, which seemed to amount to warranty information and various QR codes to scan. It’s thick! I haven’t seen a little notebook like this from Apple ever.

This unboxing experience — probably my fault to an extent, due to unfamiliarity — set me on the wrong path, in my opinion. From the onset, I felt the experience was cheaper than Apple’s; less attention has been given to details, and this box is far, far easier to chuck in the garbage.

On First Wear and Setup Experiences

I’m going by memory here, but the initial FitBit Air setup also had some differences from my experiences with Apple products. I had zero issue with Bluetooth connection to my iPhone, though this was just a “simple connection” — there weren’t any specific custom popover views like you would get with a pair of AirPods or the Apple Pencil on iPad (I’m well aware this is a Google product connecting to an Apple product; those first-party experiences shouldn’t be expected when going cross-platform).

Where things really differed was in the dreaded “update before you use experience”. After downloading the Google Health app and initially connecting, I had to hold the FitBit Air close to my iPhone while a mandatory update hit the FitBit Air before I could use it. I’ve grown so used to not having to update a device the moment I unbox it.

Shades of updates-past. I thought we had grown past this insanity.

On Syncing Data Experiences

Though I’ll talk more in depth at some point about the FitBit Air’s syncing differences (I won’t call them “shortcomings”, as I expect my issues are cross-platform based and not limitations), I’ve been surprised at the FitBit Air’s lack of integration into third-party apps and accessories. The FitBit Air is supposed to be a health and fitness tracker, but I can’t have it properly connect to any app or service or accessory outside the Google Health app itself.

Take the Peloton Bike for example. Am I crazy to think the Peloton Bike would be a perfect accessory for the FitBit Air to feed data into and receive data from? I have been able to see the FitBit Air and connect (I think it was connected, at least), but heart rate data doesn’t feed into the Bike, and no data apart from “Workout” ended up inside Google Health. No cardio load, no cardio zone information — nothing. Just “Workout”.

I have done some — borderline a lot — of research as to how the FitBit Air syncs to various services. Early on, I read there should be no issue connecting to the Peloton. I also read how you can transfer data through Apple Health into Google Health, and then use Google Health Premium’s AI features to act as a proper coach for you. What I’ve experienced are poor to no data sync, limited data transfer, and a Google Health Premium AI coach that says I worked out strenuously during my Wednesday evening round of golf.

Ha! “Strenuously.”

Overall, my first experiences with a Google product have been, well, different. So far, my experiences remind me more of those early years of trying to connect various accessories and softwares to a Windows computer, wherein you’d have to update and duct tape your way to a result. In Apple land — yes, I recognize there are some hiccups — things just tend to work. Seamlessly. Without thinking.

The promise of the wide world outside Apple’s cemented garden of Eden has always been one of flexibility, functionality, and customizability. Perhaps this is the case. The FitBit Air, though? Yeah, no. My experiences have been torn, intermittent, and rigid.

I don’t expect the FitBit Air to fit. If you know what I mean.