Matt Galligan

When iMessage was announced, I immediately thought it was brilliant. Not only for getting away from the ancient SMS protocol, but as a method of delivery of messages across multiple devices. Now that plenty of people had both an iPhone and an iPad, how great would it be if I could message friends, and receive messages on all of my devices? The intention of the feature was to be very fluid, and it does perform nicely whenever a message is sent from a phone to phone through phone numbers and gracefully degrades to SMS when no data is available.

Now that iMessage is finally in the wild and thanks to iOS 5 upgrades, available to most everyone with an iPhone I was able to test its functionality.

Man, was I disappointed in the user experience nightmare that followed.

Sending and Receiving using iPhone

First off, let’s cover how iMessages are sent and received. On the iPhone, you have the option of using your phone number (of course), but also the Apple ID (or iCloud ID) to which your device is registered. We’ll call that an iMessage address for simplicity’s sake. This allows iMessages to be received at either the phone number or iMessage address. When you send a message however, one of those two has to be the sender. This is known simply as the “Caller ID”.

The gist is that if I send a message from my phone (using my number as caller ID) to another iMessage device using a phone number as the recipient it starts to send as an iMessage over data. This is represented by the “send” button being blue, and the subsequent message background as blue too. However, if for some reason the message can’t be sent via data, a phone number-to-phone number message will fall back on SMS.

However, if I set my “caller ID” to my iMessage address and send a message to another phone number things start to get hairy. Let’s say I send a message as I just described - iMessage addy to phone number. The recipient now wants to send a reply to that message - it will be replying to the iMessage address, not the phone number. Now, in the event that my phone drops out of data coverage (which can be quite often while traveling), I won’t receive that message. Nor will it fall back on SMS.

iMessage on iPad

The promise of iMessage - receiving messages across devices - doesn’t quite work as smoothly as one might think.

In the event that someone sends me an iMessage to my iPhone’s phone number it will not show up on my iPad. Furthermore, if I’m identifying my iPhone’s caller ID as my phone number, it will never get to my iPad. However, if I change that to the iMessage address, I can begin to receive messages across both devices. Though as I described above, if I use an iMessage address as my caller ID, in the event that data is not available, it won’t fall back to SMS.

I’ve made a chart to help explain this insanity:

Click to enlarge

iMessage in Practice

Some might think these are edge cases to which I would answer “absolutely not”. Sending messages to phone numbers is what people are used to. Changing that behavior will probably prove quite difficult. Knowing that a message won’t arrive to me if I’m not on data and using my iMessage address as Caller ID disturbs me a bit.

I recently sent some iMessages back and forth with a friend of mine who was traveling. He happened to be on a plane with WiFi and was sending messages with his iPad. Robert was excited that he was able to send these messages but I was getting confused when my messages to him weren’t arriving. Later when I looked back, I realized I had four separate message groups from him: an iMessage address, second iMessage address, Google Voice SMS and iMessage (but sent from a phone number Caller ID).

To illustrate the confusion when he wasn’t receiving certain messages here’s our correspondence:

Clearly this makes for some incredibly confusing and disjointed conversations - not to mention the potential of not seeing messages at all.

The Solution

Apple could have easily avoided these problems with a few very simple processes:

• When authenticating an iMessage address (or multiple), the phone number from one (or more) iPhones get added into that account. This way, regardless of what device someone is using one could receive a message to a phone number via an iPad since it’s working through the iMessage protocol first, then SMS.

• Allow me to send messages from the iPad using the Caller ID of my iPhone. This way, whenever someone receives the message, even from my iPad, it identifies as my phone number, not an iMessage address.

• Fall back to SMS any time a message is not confirmed as received including when a message is sent to an iMessage address. Considering my first point, when confirming iMessage addresses and phone numbers together, this shouldn’t be hard.

Conclusion

Apple has a really interesting product with iMessage. The problems described above make for a very poor user experience currently, but the solutions are primarily technical and definitely not insurmountable.

There has been some rumor that Apple will begin to include iMessage in iChat or another messaging app on Mac OS X. It’s imperative that they clear up some of these issues before that happens or there will be a lot of confusion around where messages are delivered and why they’re not received when data’s not available.

I can only hope that Apple has already figured this much out and is working on a solution. But until that solution is shown, I’ll continue to be harping on why iMessage has such an incredibly poor user experience. Come on, Apple. You’re better than this!

Confession: I’m a horrible procrastinator.

In high school, I’d wait until literally the last 24-48 hours to write my papers, sometimes not even getting them done. I hated busy work. That trend continued through college, only that time the impact was far worse. Through my working career, I’ve noticed similar trends. I tended to wait until the last minute to get stuff done…and that’s IF I remembered when the last minute actually was.

I’ve tried for years to get this under control, but had never found the right solution. I’ve tried so many software tools (read: every one of them) that helped with organization and task completion. But the thing that I noticed was that most of these tools are horribly overcomplicated for most people and tend to make the problems even worse.

Let’s look at a couple of examples:

Here’s OmniFocus. It’s insanely complicated, does everything under the kitchen sink and has the looks of an overflowing desk. Though to be fair, I’m sure that it absolutely works for some people.

Here’s Things, the “easy” one of the bunch. Forget that they haven’t had over-the-air device syncing and still don’t, the “ease” still isn’t quite there to me. Here’s an example of them outlining simple “explanations” of the many features in a few marketing graphics.

After many years of trying to over optimize and conform to the software to get my shit done, I finally gave up and went for paper. Here was the result:

What did I find out? I actually got shit done. I didn’t need over the air syncing because, well, I just carried my notebook around and wrote it all done. I didn’t need tagging, or all the other stuff. It also felt incredibly satisfying to just cross stuff off when it was accomplished. This method has really worked for me for the last few months, up until my iPhone 4S.

Enter the iOS 5 Reminders App. It didn’t have tags. It didn’t have milestones, no concept of “areas of responsibility”, no starring, not much more than tasks and due dates. At first, I cringed, thinking “wow, how could they release software that had 10% the features of Things and OmniFocus and Wunderlist and blah blah. Then I realized what Apple did: they re-created my paper notebook in an app. No bullshit, just tasks.

But then they went a step further and added the next killer feature:

Siri

Now, no matter what I was doing - whether with my phone in and hand or over bluetooth while out and about, I could log the tasks that I needed to accomplish. Siri can set my reminder, as well as when I should be notified about it.

Then, while still adhering to simplicity, they made it more useful with the location-enabled reminders. I could say things like “Siri, remind me to take out the trash when I get home” and then, as soon as I drove up to my house, I would get notified to take the trash out. Seems simple, and maybe superfluous, but it’s powerful. Trust me.

It underscored to me what Apple’s motto has been for a long time and why I love them so much - get rid of the bullshit, simplify. I realized I didn’t need tags, or a lot of the other crap that the various To Do apps out there provided. I just needed something to get my work done and then get out of my way, not create more work for myself.

After a few months with the paper, and now the Reminders app, I can safely say that my life is far more organized and I’m feeling GREAT just checking stuff off the list. Removing features made the software far more usable. This is certainly the mantra of Apple, but also lots of other companies, like 37 Signals. I just wish more people adhered to that philosophy.

Remembering that I’ll be dead soon is the most important tool I’ve ever encountered to help me make the big choices in life. Because almost everything — all external expectations, all pride, all fear of embarrassment or failure - these things just fall away in the face of death, leaving only what is truly important. Remembering that you are going to die is the best way I know to avoid the trap of thinking you have something to lose. You are already naked. There is no reason not to follow your heart.

This was the closest I’ve been to facing death, and I hope it’s the closest I get for a few more decades. Having lived through it, I can now say this to you with a bit more certainty than when death was a useful but purely intellectual concept:

No one wants to die. Even people who want to go to heaven don’t want to die to get there. And yet death is the destination we all share. No one has ever escaped it. And that is as it should be, because Death is very likely the single best invention of Life. It is Life’s change agent. It clears out the old to make way for the new. Right now the new is you, but someday not too long from now, you will gradually become the old and be cleared away. Sorry to be so dramatic, but it is quite true.

Steve Jobs - June 12, 2005

There is something profound that I feel right now. I’ve never in my life met Steve Jobs. Yet he had one of the greatest impacts on my life as anyone else. He taught me about emotion through design. He taught me to just be me, ignore the critics, and do what I feel is right. And he taught me to fight for life. Take every single breath as though it was my last, and ensure that the importance I place behind legacy continues to be greater than that of currency.

It’s a very sad day in the world. We lost one of the greatest human beings to have ever graced this planet. We won’t get him back. But the influence that he’s had on the world can be seen everywhere. Though the world won’t be the same without him, we’ll continue to live up to his dream of a more perfect world through design and challenging the status quo.

So “[h]ere’s to the crazy ones. The rebels. The troublemakers. The ones who see things differently. While some may see them as the crazy ones, we see genius. Because the people who are crazy enough to think they can change the world, are the ones who do.”

Goodbye, Steve. We’ll miss you.