Week 17.21

  • This may have been the first time that an Apple event week coincided with my birthday week. Expectations of having a present to buy myself were high, but when it turned out that only the iPad Pro in 12.9” size would be getting the mini-LED display technology I’d been waiting for, and that the damned thing would cost me about S$3,000 in all (with AppleCare+, Pencil, and Magic Keyboard), I began to have second thoughts. After a little deliberation and rationalizing, I ordered myself last year’s iPad Air as a good enough substitute. Normally, you’d expect to receive it in a day or two, but perhaps because of Covid, its ETA was next week instead.
  • And then on the weekend, I started to doubt the wisdom of not buying the latest and greatest, because I knew it would grow to become a nagging dissatisfaction. It would only cost an additional S$360 to go from a 256GB WiFi iPad Air to a 256GB WiFi iPad Pro 11”. That money pays for (roughly in descending order of importance to me): a smoother and brighter ProMotion display; the M1 chip for more future-proof performance; Face ID; four speakers instead of two; LIDAR and additional cameras, including the new front-facing one with Center Stage; supposedly “studio-quality” microphones; and Thunderbolt/USB4 compatibility. Sounds like a good deal, doesn’t it? A pity about not having mini-LED on the 11”, but it’s clearly a better device regardless. So I’ve canceled the iPad Air and will have to wait at least another month for the Pro to go on sale.
  • The other nagging thought I had was that maybe some new features in iPadOS 15 this year will be exclusive to M1-bearing iPads. These iPads have 8/16GB of RAM for the first time (actually listed on Apple’s site!), which makes them the hardware equal of the M1 MacBooks. What if… developers of Mac apps could elect to publish quick iPad versions? I don’t have a Mac of my own anymore, and a way to occasionally manage and transfer files to hardware devices like my Kobo would be welcome, so any app interoperability would be amazing. What if you could run an iPad over two displays for double the multitasking? If any of this comes to pass but leaves the iPad Air out, I wouldn’t even be able to look at it, let alone use it for the next three years.
  • TL;DR: the iPad Air is great and more than enough to get stuff done, but if you want slightly nicer bits, you might want to pay more for the 11” Pro. And I’ve decided that I am the type of idiot who would wallow in eternal regret if he didn’t spring for the nice bits.
  • Because it’s a birthday month, the wanton overeating continued. Cake, pizza, cocktails, wagyu beef bourguignon, a lavish slab of kueh salat from a Michelin-starred restaurant, and a lovely bit of smoked pork collar at a wedding lunch I had the privilege to attend. Tonight, we’re going out for more Italian. There’s yakiniku scheduled in a few days. It’s irresponsible but no one has stepped in to stop me.
  • I’ve slowed down on Star Trek: Legends, mostly because it’s so bug ridden I think I’m better off waiting for another update before continuing.
  • I enjoyed some of Marvel’s Runaways comic series a few years back, but didn’t know it was turned into a TV show for Hulu. Three seasons of it are now available on our local Disney+ and it’s very bingeable, as we found out this weekend. The less you know going in, the better. Most synopses give away too much in the first sentence alone.
  • A few weeks ago, HEY.com started selling t-shirts with their logo on them. Knowing that they’re really ads for their service, they priced them low; apparently at cost. As an enthusiastic early adopter and current user, I had to get one. It finally arrived in Singapore on my birthday, which was a nice coincidence.

Hold up, HEY

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.

Continue reading “Hold up, HEY”

An early look at HEY email

(For Part 2 of this review, check out: Hold up, HEY)

I’ve been pretty keen to see HEY’s rethinking of email, and just got my early access invitation this week (I joined the queue back in February, perhaps on Day 2 of their recruitment drive). I was also an early adopter of Gmail back in 2004, and as they say on the manifesto page, there’s not been much innovation in the world of personal email since. If anything, email has been in decline and most of its use cases now belong to chat platforms (keeping up with friends), workplace project management/collaboration suites (enterprise communications), and services’ own portals (seeing account and order histories). The resurgence of newsletters is one bright spot, and displaying them is one of the main jobs of my email account.

Anyway, I get excited about new things quite easily. When the invitations started rolling out, I was obsessively checking my inbox, and I kid you not, literally dreaming about getting mine to the point where I was waking up in the middle of the night with the urge to check my mail! Part of the anxiety probably came from wanting needing to secure my address of choice, like I was lucky enough to do back in 2004 with Gmail. Just try getting your name now without adding random numbers; I don’t know how the poor kids today deal with the scarcity. My wife also wants any readers to know that she’s heard enough about my two username options, the pros and cons of both, and never wants to discuss email addresses again.

So now that I’ve used it for a little bit, I’m undecided if I should make this my primary email service. On one hand, everything they promise is true. The workflows are elegant, the way it puts you at the center of the experience is refreshing (no stranger can disturb your peace, OCD freaks can bundle threads together, etc.), and the emphasis on privacy and business model transparency is way better than any free alternative. On the other hand, it’s not entirely how I’d like to use email, and some edges are rough to the touch.

Continue reading “An early look at HEY email”