What made the service so refreshing at the start was its dedication to art and quality, stickiness and engagement metrics be damned. You paid a subscription fee, and got access to a peaceful library of games that didn’t try to milk wallet-attached endorphins out of your brain. We got delightful little experiences like Assemble with Care and WHAT THE GOLF?, and I stuck around on the promise that we’d get a steady stream of those. Well, it seems that train has stopped because somebody upstairs wants more addictive games that will keep people subscribed past the free trial.
One example of what Apple wants, according to Bloomberg, is Grindstone. I personally love it; a fun pick-up-and-play puzzler, and an evergreen game you could easily be playing years from now. But not every game needs to be a Grindstone, and there’s only room for one or two Grindstones in my life at any time. These are games you use to soak up free time, go-to icons for when a moment appears while in line for something, or on the bus. There are plenty of them already on the App Store, so Apple Arcade should supply a breadth of other experiences.
I see the potential of Apple Arcade as analogous to the Apple TV+ strategy : quality over quantity, unique visions only. A change of course so soon comes across as a lack of courage. It’s a long game, so to speak. If people aren’t staying past the trial, maybe they’re not reaching enough of the right people who’ll be their early adopters. Even Airpods didn’t take off immediately.
I now have a suspicion that Calibre also causes problems with iCloud Drive, so I’m leaving this here for anyone it might affect. Some scenarios for the search engines below:
If you store your Calibre Library folder on iCloud Drive, and have noticed that your remaining space does not reflect the storage you’re using, this is for you.
If you have deleted files on iCloud Drive but find that the free space reported by iCloud.com or your device does not immediately update to reflect the deletion, or…
If you have removed everything on iCloud Drive but still find space allocated to “Documents” in the “Manage Storage” section of iCloud settings on your iPhone/iPad — in other words, if you expect to have free space, and have done everything including a check of the “Recently Deleted” area and emptied your Recycle Bin, but the amount of free space is still inaccurate, I know that feeling.
This seems to happen to a lot of people, perhaps for other reasons, but it happens. Skip ahead to “Is it you, Calibre?” if you just want my conclusion.
So here’s my experience. A couple of years ago, I had this issue, and had to call Apple Support. It took several calls to resolve, because they wanted me to sign out of iCloud on every device (not an insignificant hassle with multiple devices), and when that established that the issue was on their servers, it had to be escalated to Engineering, and the eventual fix was they wiped everything on my Drive and reset it. I had to backup all my files locally (requires a Mac!) first. I believe I still suffered some data loss.
After that, it was all good, but my confidence in iCloud Drive was shaken, and I didn’t want to use it as storage for anything important. Every year since then, they’ve made enhancements to iCloud Drive, and to the Files.app on iOS, which has made me slowly more willing to embrace it again as a cloud file system worthy of My Stuff.
And then this happened again. 13GB of space just wouldn’t come back after I’d deleted files. The files were gone, the space was not reclaimed. After putting it off for two weeks, I got on the phone with Apple again, and two calls later, they managed to “repair” my Drive using some standard tools they have (Engineering was not involved this time). So, a slightly better experience than before.
Is it you, Calibre?
I’ll say upfront that this is a hunch. I don’t have the strength anymore to experiment on my iCloud account and conclusively prove anything.
Both times this happened to my iCloud Drive, I was using it quite “normally”. Nothing fancy, except that my Calibre Library folder was on it, and I knew that the Calibre app was actively updating files on it whenever I added/removed ebooks. This last time, the problem appeared after I’d deleted a ton of files THROUGH Calibre, and as best I can recall, a similar situation took place years ago.
With the Amazon Kindle problem, there’s something about the way that Calibre writes files to the Kindle’s drive that causes it. In other words, Calibre (which is a sluggish cross-platform app that behaves in a very non-Maclike way) may have some non-standard ways of interacting with the OS and filesystem. I think the way that it writes/deletes files isn’t the same as if you manually dragged files around yourself via the Finder. It might be through some low-level UNIX operations, but this is where I’m out of my depth.
So it’s not a stretch to imagine that when you delete ebooks in Calibre, it deletes them from your drive in a way that may cause issues. Deletes them in a way that is invisible to iCloud, so it doesn’t know that the files are gone and it should give you the space back. On a local drive? It works fine, and that’s how it’s used by millions anyway. But on a weird aliased virtual cloud drive that Apple hacked together inside a folder called “Mobile Documents”? Maybe not fine!
Here’s what I’d suggest trying if you have this problem: move your Calibre Library off iCloud Drive. I’ve put mine on Dropbox and it seems fine. Do NOT put it on Google Drive. Call Apple, and have them repair or reset your drive. Some luck is required here, but they’re your only hope. Once you get your missing space back, don’t use Calibre with it again.
I’ll be here with crossed fingers too, waiting to see if this happens again.
The debut of HEY email has been an interesting case study in launching a new service, in part because it took place on social media — a two-way street that led to them getting public feedback that’s already led to significant changes. As others have done in recent years, the launch was a staggered rollout with invite codes and a waitlist, and the resulting members-only feel and scarcity drove tens of thousands more to join the waitlist. Some say this is intentional marketing, but it’s also legitimately done to manage the experience when someone isn’t sure how much interest there will be.
I took notes on my hands-on experience in a previous post, and have spent a week now getting to grips with it, trying to picture it as my primary email service for the foreseeable future. The commitment isn’t just a new email address to inform people about; it’s also paying a perpetual premium service fee. After 16 years of “free” Gmail, that’s a big decision. Yes, you’re free to leave any time and they’ll forward all emails sent to you anywhere else you’d like, but I wouldn’t use a @hey.com address if I wasn’t actually using HEY.
Everybody’s got opinions
But before the details of my decision (like, who cares, right?), I wanted to comment on the fascinating public launch of HEY that we’ve been spectators to, and how its creators have had to walk back some of their design decisions after product met reality.
As my friend YJ says above, Basecamp and HEY are heavily opinionated products by opinionated people; it’s what allows them to take a well-established thing like email, with its standard organizing paradigms of Inbox, Outbox, Sent, Spam, and Trash folders, and try something new. It’s only meant to satisfy a certain type of user with certain needs and preferences.
It’s not easy building something out of new ideas, at huge scale, and making sure it’s robust enough to carry the personal and business correspondence of paying customers who’ll depend on it for time-sensitive messages. By Basecamp’s account, they’ve been working quietly on HEY for two years before this month’s semi-public launch. I think they deserve a tremendous amount of credit both for attempting it and for how stable it has been.
When we design services, we know we won’t catch everything or get it right the first time. It’s about having priorities and principles, and optimizing against them every step of the way. If you’ve defined and studied your target audience, and care about pleasing them to the exception of everyone else, then you can make decisions based on their needs. If you put in the work to develop a core experience that will set your business apart, then that becomes the thing you protect even if Apple or anyone else tries to make you change it. Some companies famously put speed over certainty, and while it dazzled a lot of CIOs and inspired them to try and do the same, its pitfalls are now well known.
We don’t know what HEY’s development process looked like, or what they prioritized, and so we can only guess from what they actually shipped and what they’ve done since. Upon contact with the wider marketplace, some of those opinionated ideas are now being challenged as problematic or discriminatory. Could more user research and testing have caught them before launch? Probably. Was catching them before launch a priority for the team, or did they intend to test them in public and fix unintended consequences as they were discovered? To their credit again, they’ve fixed a lot of things very fast in the past week. From adding disposable functionality suggested by Apple to dumping fully built, non-trivial features… their responsiveness has been impressive.
Things that came broken
Let’s look at a couple of Twitter exchanges and changes I’ve spotted. On my first day with HEY, I noticed an unusual option in the “More” menu on every email thread. It was a button labeled something like “Generate Public Link”. This actually published the entire email conversation thread to a public webpage, allowing any third party to read and follow the exchange. I used it to help share a problem I was seeing with their support team, which is a nice way of enabling them to help customers without giving full access to all mail. And while you could always share private emails to a third party with copy/paste, screenshots, PDFs, etc. there was something unsettling about this. None of the other people would receive any notification that they were being “listened in on”, and anyone with the link would be able to see not just all previous emails, but any new ones added to the thread for as long as it was publicly shared.
You could be in a conversation with 20 people and not know if any one of them had generated a link and leaked it. When I explained this in a group chat, there was some disbelief. One person called it a “built-in whistleblower feature”. After others complained on Twitter about the potential for abuse, this feature was completely removed.
In my last update here, three long months ago, I’d just set up a new WiFi system with enough reach to connect our largely neglected study, which gave me a new place to hang out and play music too loudly.
Shortly thereafter, I decided the acoustics of that room were too boomy for the Beolit speaker I’d put in, and picked up a little Sonos which can be tuned to suit the space (it’s much better).
Shortly thereafter, a measure of hell broke loose everywhere, which I don’t need to explain. In the tiny window before nationwide lockdown was called, my wife and I decided to celebrate our anniversary with a staycation since getting away was impossible. We booked ourselves in for a weekend, visited the buffets, had cocktails in the lounge, and sat by the pool that first day reading more news and feeling something in the wind.
Literally overnight, we saw the hotel reconfigure their club lounge for social distancing, cutting the capacity in half. With not much else to do but eat canapés and drink while watching the news, I distinctly recall the numbers then: 380,000 infections worldwide. Yesterday, I saw that number in the news again, for global deaths.
According to the log my teammates have been keeping, we started working from home in the third week of March, later than our other colleagues not attached to client projects at the time. For that period of about a week, showing up at a reduced occupancy office building/mall was surreal, recalling Ling Ma’s novel Severance, where the protagonist keeps going to work at her Manhattan office long after the city stops working, and we were glad when the call was made to not take any more chances.
That move to make our home study more usable/livable/enjoyable just before this hit, which on hindsight was just down to luck and the High Fidelity TV series, was probably the most well-timed decision I’ll make all year. It’s given me a separate workspace from my wife who’s taken to occupying the living room’s solar-facing counter. Given that we’re both on calls a lot now, if I had to be nearby for WiFi purposes, I think there’d be trouble.
A lot of what we do with clients and their customers in the business of design used to happen in person. Speaking with people, watching them at work, communicating ideas — it takes a lot of channels to supply the necessary bandwidth, from spoken words and scribblings on a board to body language and moving things around in space. It’s also true for many other professions, and is probably why many fantasize that VR will be the long-term answer in the event that there won’t be a vaccine, if we agree that plexiglass shields in the office aren’t a solution for getting back to work.
We started working from home on a Wednesday and had to figure out how we’d start interviewing people the very next day; interviews that were originally planned to be in-person conversations. For a bunch of reasons, it wasn’t as easy as sending a Zoom meeting link. We ended up keeping those sessions simple and voice only; better to get the basics right and extract some good data than get fancy and fuck it all up.
Two months later, between us and other teams across the studio, I think we’re beginning to see how many of the old activities can be done virtually. The next step will be to devise new activities that aren’t constrained by assumptions about how work should be done. Maybe we’ll go back, maybe we won’t. One thing about remote work of this sort, technology constraints (including literacy) have a huge impact on who you can involve and co-create with. Almost anyone can pick up a pen or gesture at a thing. Now try to get them to manipulate content on a Miro or Mural board using an aging laptop. Now try to get them doing it in VR. What’s the equivalent of a Post-It note for virtual work: the simplest, most flexible atom of a tool for thinking aloud with anyone? Texting in a group chat?
Otherwise, I’ve done some of the usual quarantine things. I’ve tried cutting my own hair (bought some clippers for it). I’ve been making cold brew coffee (bought a Hario bottle for it). We made that dalgona coffee one time but it was foul (already had turns out we actually bought the apocalypse-ready instant coffee for it). I’ve been making more cocktails and drinking IPAs at home instead of at the bar (bought the ingredients and ordered the cases, respectively). I’ve put on weight (bought a lot of takeout for it). I’ve been reading more (bought a Kobo reader for it). I’ve played upwards of 110 hours of Animal Crossing New Horizons (bought the game day one for it). Uh… having made that list, I am a little disgusted. Clearly, if life gives me lemons, I buy a juicer.
The national lockdown here in Singapore ends in name next Monday, but the cautious re-opening will surely take more than a couple of months. The first people to be allowed back into office buildings at first will be those who haven’t been able to do their jobs from home for legal or technical reasons, and I think it’ll be September before most white-collared types find out what their leaders think about ending the great WFH experiment vs. saving a ton on commercial rent.
Note: This post contains a couple of Amazon affiliate links, which I’m trying out… again? I have a vague memory of using them on a couple of my sites before.
As I write this update, I’m listening to Joni Mitchell’s Little Green at possibly too high a volume for 11 o’clock at night, but I have no idea how thick these walls are, so let’s find out. This unusually unneighborly behavior has been brought on by watching the new High Fidelity TV series (yes, based on that Nick Hornby book), starring Zoe Kravitz in the role played by John Cusack in the 2000 film, and look, the whole thing is sublime. Watch it, because it’ll remind you that you were once young and played your music loud. And that it’s been too damn long since you’ve heard Darondo’s Didn’t I.
This is also made possible by the fact that I’ve finally traded in our aging Asus router for a pair of Netgear Orbi mesh routers. Only 1.5 years after moving in. And so the internet is now flowing into a part of the house that I’d neglected before because what in the hell am I supposed to do in a room with no WiFi? This room is now going to be a place where I can sit in near darkness, streaming really warm sounds out of a cranky first-gen Beolit speaker, writing on my iPad, and drinking. Aww yes.
Speaking of Little Green…
I spent most of last year getting up to speed on personal finance basics at the ripe old age of a̷l̷m̷o̷s̷t̷ 4̷0̷. For most of my working life, money and investing was an essential resource that I never fully understood, and I was mostly happy to have it sit in that blind spot, content that simple saving would do alright “for now” and nervously assuming that the “for later” part would sort itself out in the end.
I put some blame on the false absolutes we were taught in school: kids are sorted into separate paths focusing on either sciences, economics, or the arts around 14, if I recall correctly, and it’s too easy to let that define you to yourself. I ended up with the thinking that money was for the money people. Of course, I accept the residual blame for hiding behind that lazy excuse all these years.
So when I read Ramit Sethi’s approachable book “I Will Teach You to be Rich” last month, I was relieved to find that I already knew the majority of its lessons. As he puts it, the best time for me to have started investing was 15 years ago; the second-best time is now. Another practice that made sense to me: setting up monthly financial check-ins as a family. Even if there’s no news to update each other about, it sets aside time to think and plan.
In any case, it certainly seems like personal finance is being discussed a lot more frequently in casual conversation today than it was when I was growing up, or even in the past 10 years, for that matter. Financial literacy has probably never been higher.
I attribute this to the rise of fintech startups, how many there are, and how visible their services are in our Instagram feeds. If you live in Singapore and haven’t seen a StashAway/Endowus/Syfe/Kristal ad, then I’ve got a referral code to offer you.
For the unfamiliar, these are all so-called roboadvisors, usually helping you to buy into a portfolio of ETFs based on your asset allocation preferences/risk appetite, while taking a sub-0.8% cut for management fees. It’s remarkably easy to get started once you’ve educated yourself and decided you want in — whereas back in my day, before online banking (let alone mobile banking), starting a trading account was an arcane art that required serious capital.
Based on what I’ve seen, the equivalent offerings from traditional banks (DBS, UOB, OCBC) are only playing catch-up, both in terms of fees and design. It would be fun to do some research on how the boundaries of trust have moved and what Singaporeans’ financial behaviors look like now. I used to wonder what the big deal was with the local licensing exercise around digital banks, but now that I think about it, there’s obviously blood in the water.