Your Favorite Messaging App Stinks

And So Does Mine

I’m gonna take a break this week from delivery a sermon on Universal Minimum Incomes and taxing the rich. I know, I know. That’s what you all come here for, but this is what’s on my brain at 2:49AM: Messaging Apps—why they all stink.

Now, when I say they stink it’s out of love for the concept of messaging. I love getting messages; I also love sending them. I’ve tried so many apps and they all have wonderful features, beautiful interfaces, and do their job… fine.

So what is the problem?

None of them have everything I want. I recognize that’s pretty self-absorbed, but it bugs me enough that I’m going to just spell it out right here.

1. My friends need to be on it.

2. I need to get notified of messages I want to see. I need to not get notified of messages I don’t want to see.

3. I need to be sure my conversations are private.

4. I can’t stand to be left unread/left on read.

5. I need rich media options.

6. I need to be able to find that one message from back whenever.

7. I need to be able to go back and edit my typos.

8. I need message threading, and I need it to be used.

9. I don’t even know who you are.

And what’s the best way to get what I want?

Buy it with your kind donation!

No! To whine about it where no one will ever see it.

My friends need to be on it.

This one is pretty obvious, right. What good is a messaging app if I have no one to send messages to?

Right now I think I have about a dozen messaging apps on my phone. When I want to message someone, the first thing I have to do is remember who is where, and then remember the limitations of that platform.

Back in the day, there was Trillian—and yes, I know it still exists. The glory of Trillian was that I could get all my ICQ, AIM, and MSN messages in one application. It was glorious, but no one uses any of those anymore. The modern incarnation is not particularly active, and while it can handle a range of the big messaging apps, it doesn’t do enough to make it viable for me.

I need to get notified of messages I want to see. I need to not get notified of messages I don’t want to see.

I really wanted to like Slack, Teams, Discord, Asana, choose your poison. I still do use some of them. But they all suffer from really poor notification management.

I admit, it’s probably my fault—but I know I’m not alone. Maybe somewhere in the settings there is something important I didn’t see. Regardless, half the time I get an important message I get no notification it was sent.

Is it because I had the client open at the time the message was sent? Perhaps on a different device? Is it my phone? A compatibility issue? Did I get the notification on my smartwatch and accidentally swipe it away?

Who knows. I didn’t get it.

And then there’s the other problem. 100 servers with 100 channels with 100 people sending 100 messages, and the App thinks I want all those notifications by default. Notification badges are great—and also completely useless if they are always on. I have a dozen of these apps: I can’t go through them all and manually set how I want all these notifications.

I need to be sure my conversations are private.

This one is so obvious it barely needs to be mentioned. Big brother is always watching.

I need a platform that is encrypted and secure, and I also need it to be owned by a company that isn’t cozying up with Fascist tyrants, secret police, and state security forces. That seems to be a pretty high hurdle to clear in this age.

Left unread, left on read.

Maybe this is a layer 8 problem. Maybe imperfect humans are not designed for an always on age. I know I certainly am not. But there is nothing more frustrating than sending an important message and not getting a reply.

Whether the message hasn’t been received, or my recipient is sitting on it, it is incredibly frustrating to just wait and hope for a response.

Did you actually see it?
Did you forget about it?
Did you not think it was important?
Are you too busy right now?
Are you mad at me?
Am I annoying you by sending too many messages?

And then obviously the same is true in reverse. You sent me an important message and I’m not responding.

Did I miss the notification?
Did I turn off the feature to display when I’m active?
Is it so complex I need time to respond appropriately?

Who knows. All we see is “read” or “unread,” or maybe not even that. Why not let me put a comment on that message, or a TODO, or mark my message as urgent. Let me bump it to the top of our conversation to show I am still waiting on an answer.

Or perhaps waiting on a donation…

I need rich media options.

I need to be able to say emojis.
I need to be able to send messages in non-English characters.
I need markdown and the ability to modify font styles.
I need to send a picture.
I need to send a large video.
I need to find and send a funny gif or meme.

I need to send you this link.
I need it to have a thumbnail, but not that thumbnail.

And if I can’t do whichever of those I want, right now, I’m going to delete this stupid app.

I need to be able to find that one message from back whenever.

I sent it to you in meeting chat—or was it private chat? Group chat? When? In which app? You know, maybe it was an email. I think I pinned it in one of those places. Did someone unpin it?

That search box is for servers; you need to use the one for messages. No not that one, that’s for messages in this specific chat. No, it’s not that one either: that’s for usernames. Now you are searching just this mailbox; no! you just searched every mailbox.

This app only saves messages sent on this specific device; this one deletes them after 30 days. This one has no search function at all; this one’s search has blindspots.

You need to write your query using this language that is specific to this app—oh and it doesn’t have that particular filter: that’s only in that other app.

I need to be able to go back and edit my typos.

I type fast. I use my phone to type. I use autocorrect. I use slide-typing. I use predictive input. And, oops. That wasn’t the word I wanted, and I already hit send. If I can’t correct my message, do I have to send a half dozen more messages correcting the first one? Ick.

I need message threading, and I need it to be usable.

Ah, the whole reason I wanted to write this post. I’m here at last.

My mom and I talk are kind of scatterbrained in conversation. Topics come and go, they get left alone for a while, and then suddenly they are back. They get missed entirely, or we don’t know how to respond. I was thinking about that first message, and three more came in while I was responding to it.

Threading is key. And getting people to use it is worse than pulling teeth.

First off, reply functions are ok, the ones that quote the original message. It’s clear what you are referring to, and it lets me go back to something I still want to talk about when you’ve moved on. They also take up a lot of real estate and bury a big chunk of other messages. Not ideal.

So here are the capital sins of threading implementations:

1. Threads are not collapsible and don’t automatically collapse

2. Old threads with new messages and no way to know there is new content

3. Threaded messages with no notifications

4. Threaded messages that are hard to reply to, in thread.

And the feature I’ve never seen anywhere:

Adding a message to an existing thread, after it was written.

I dream of apps where messages thread automatically. One where unanswered or unacknowledged messages float at the bottom, swimming between larger threads actively being discussed. Of threads that can be closed and marked resolved, but then reopened when there is something important to add. Dragging a message into the thread it belongs in. Muting a thread I don’t care about at all.

But then I awake and have to scroll back 50 pages to see if anyone responded to my question—and no one did.

I don’t even know who you are.

Who is this person?
They changed their handle and their avatar.
We messaged a lot, years ago, but now I don’t know where I know them from.
Was this the person who was really triggered by that?

My app needs to let me leave notes on people—that they can’t see or change—and I need to be able to search and filter those. Also, I’m going to forget to, so maybe help me remember to add those notes?

Naomi, just make it yourself. You’re an app developer.

I’m working on it. Give me another decade or two.

I appreciate all of you who put up with this little rant. I know in the big scheme of things these are minor inconveniences that everyone deals with or doesn’t even notice. For me, the chance to get it in writing is important, so that I can think out loud and hear what others think about my rant.

Don’t worry, I’ll be sharing solutions to the big problems in society again next week.