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Jared Sinclair’s post today about Glassboard got me to thinking about this type of app in general. I call them project collaboration apps because they deal more with discussions than planning. (Whereas project management apps deal more with planning than discussion.)

The best project collaboration apps I have found are:

• Glassboard
• Quip
• Slack
• Basecamp

The problem is that I simply cannot tell you which of these is the best because they all have issues and strengths. In short, here’s how I see these apps stacking up:

• Glassboard: Designed around the one idea at a time approach. A users posts a new message and there is a thread of other users responding to that message. It’s best thought of as a thread on a message board. The obvious benefit being that threads are usually very on topic and to the point. The down side being that there is less room for a conversation around a general topic, as messages are designed to be more specific than that. Should you want to be more general you will quickly get lost in all the comments on messages.
• Quip: Designed around files. Think of it like Editorially for Word documents. Quip is all about collaborating on documents, so if you are only sharing Word-like files, you cannot get anything better than Quip. It’s far better than track changes if you ask me.
• Slack: Designed around conversation topics. The newest kid on the block is very well received (I use it multiple times a day). You create #channels that have set topics. Everything flows like a more natural conversation in those rooms — like in chat rooms. Files can also be uploaded into a room, where files then get a specific comments thread for each file. Overall Slack excels at water cooler talk, and general discussion. Where it lacks is focus. If you wanted to talk specifically about one design element of an app (like a button, instead of the app design in general), it is quick and easy for that to be derailed, and then hard to track the conversation about just one specific element.
• Basecamp: The OG of this type of app is designed with a more traditional project management focus. Though, in recent updates, the app is slowly shifting to project collaboration. I’m of the opinion that Basecamp combines Quip and Glassboard, but doesn’t do either function better than those apps. Basecamp for the most part still lacks a freeform chat, which was previously built into the product with the help of Campfire. Basecamp excels at structure, but lacks in allowing structureless conversation.

In a nut shell, each app has strong reasons to use it, but none of them are there yet — to me this is evidenced by the fact that I use all four of them weekly (if not everyday). I’ve been trying to think about what is missing from these apps, or what the perfect app would be, and I’ve come up with some core ideas that I think are missing (in some form) from some, or all, of these apps:

1. Give me a way to have conversations around one central theme. Something somewhat general like ‘design’. Slack excels at this, and though you could do that with multiple boards in Glassboard, it’s not setup for free form conversation. Again, Slack is the perfect example of this. This type of loose conversation is ideal for brainstorming, and also perfect for roughing out where a project is. It’s the tool you want to keep to get the project off the ground, and then gives you a place to vent as the prject gets closer to completion.
2. Allow me to define a specific topic within a conversation. This is where Glassboard and Basecamp excel, and Slack suffers. Going back to my earlier example, if I want to talk about button design within a ‘design’ conversation I should be able to track just that discussion without being sidetracked by side discussions. For that the Topic > Comment framework is ideal. While you could create more #channels in Slack, that’s a hack of a solution. I’d like these specific topics to be visible within a main conversation, but then to later be able to just view the specific conversation on a topic. This is critical once a project is under way, and all the way through completion.
3. Commenting on files and images is crucial. Each of these apps handle this in some way, all different, but I think Basecamp handles this the best. I like that I can have a conversation on a topic in Basecamp and attach any file. In Slack you can do that, but then that file can have specific comments on just a file — which is confusing. If you are swapping mockups for one design element, it all needs to be maintained in the same thread — as Basecamp does. I should be able to upload a mockup, and each person responding should be able to comment on that, and upload iterations of that mockup all on the same ‘thread’. Again, crucial for most projects that are underway.
4. I need to collaborate on text. Basecamp has a really poor implementation of collaborating on text, and it’s so bad I don’t want to talk about it any more. Quip, clearly, does the best job here, but the app is so niche it is hard to assimilate into a workflow. Every project invovles writing something at somepoint — it should be natural part of such an app.
5. Private messages are a must, and Slack really does a good job at that. It’s nice to be able to talk directly to a team member in a private setting, but not be beeping their phone with each message. I want to be able to leave work when I leave work. I want to be able to use my comptuer without getting bugged by work. To that end, I want the private messages within the app, instead of IM or Text messages.
6. Notifications need to be smart. The app should be able to tell me when things are directed at me, and what I have and have not read. Again, Slack does a very good job at this. I talked above about how Glassboard doesn’t handle this well, and I personally think the dashboard view of Basecamp doesn’t handle this well either. Slack needs to centralize these notifications, but does the best job of the lot. I also need to have quiet hours, to turn off the notifications, but get a summary when I get back to work.
7. Bookmarks. Most of the apps have a way of bookmarking a topic, or message, but I always wish it went further. I’d love to be able to send different things within each topic/discussion to a reference folder of sorts. To be able to quickly cull together excellent ideas, tasks, and important notes in one place that is only visible to me. Something like a montage of important pits from all the things going on within the app.
8. Allow me to get old stuff out of my face: a.k.a. give me an archive buttons that works. I still want to be able to see it if I need it, but I don’t want to see something that just isn’t active anymore. Once we design that button, I only need that conversation for posterity and not for active discussion. Remove the mental overhead of seeing that discussion when I login.
9. Allow me to take any one message, or thread of messages (or files, etc) and turn it into a task for a team member. Most task systems ask you to create the task first, and then discuss it. I think that is backwards. I say, lets talk about the button design and then when we get it all figured out, assign the implementation to one person.

That’s my quick and dirty list of things that need to be addressed in project collaboration tools. Perhaps you don’t think this is all that important — these are niche tools — but to think that seems to be sticking yourself with the idea that going into the office will always mean: going into a physical office where all your coworkers are. That’s changing, and changing fast, and these tools are becoming vital to that change.

I hope they get better and get better faster than they are right now, because using four apps at once is tiring.

Most of the year I spend reacting to things going on at work, news on the web, and opportunities as they present themselves. So while I used to be a big GTD nerd, of late I tend to just be a reactionary fool. About once a year I stop working, dump everything rattling in my brain on something, and then reevaluate it all.

My goal is instead of forcing myself to work in a rigid way which may actually not work for me, I try to set habits once a year and let those habits slowly change throughout the year as I need. Then at some point I stop and reevaluate it all.

It just so happens that this once a year period is right now for me.

The first up for my changes in habits are in how I work at my desk, and on my desktop. As you can see in the picture I keep my desk very tidy, so here’s a quick rundown of what’s going on.

Left Side

On the left side of my desk I keep my camera, my iPad, my stylus, and a pen. I’m left handed so it only feels natural to keep those items on my left.

iPad & Stylus

When I get to work I layout my iPad and Bamboo Stylus as you see in the picture. I also open up the Notability app, with a “scratch” document open and ready (but the iPad off). I’ve long tried different ways of entering quick notes into my Mac (notes you might take while on a phone call), but in practice it doesn’t work to use a keyboard. Typing with one hand just is annoying.

Pen and paper are fastest, but I can’t stand a pen and paper. Instead I use Notability as the paper, and the stylus as my pen.

I keep one running file of notes in Notability, which archive once a month. This allows me to scribble phone numbers much easier than typing with one hand while on a phone call, like I would on paper, but with the added flexibility that a digital system offers.

So far this works well.

An additional note: I keep the smart cover as you see in the picture. This allows my left hand/wrist to anchor the iPad in position while I write — and keeps the iPad feeling much thinner (hand is held higher because of the cover and iPad is lower than if the cover was folded behind it) than if I were to fold the cover back behind the iPad. So while it looks a bit silly, it works much better this way and feels more comfortable.

As for the stylus: a necessary evil. I like the Cosmonaut, but the rubber makes my hand smell funny so I don’t ever use it. The Bamboo stylus is small, looks nice, and writes well.

So there you are, I guess I am an iPad stylus guy after all.

Pen

I’m currently using 1.0mm Uniball Jetstream pens with blue ink. Original documents are best signed in blue ink and that’s pretty much the only reason I have the pen: signing contracts and checks. I don’t care to hear about other pen choices, I literally just use it to sign things.

Camera

While my camera isn’t always on my desk, it usually is 60% of the time which is why I included it in the picture. There’s no reason for the camera to be on my desk, other than to serve as a reminder of what I would rather be doing.

Center

Central to my desk is my retina MacBook Pro, CODE Keyboard, trackpad, and DJ stand for my Mac. The stand is to get the computer high enough, the Mac always has Flow open and ready to go. That CODE keyboard, she’s a thing of beauty. (Also trackpad, because I don’t like the scratching sounds of a mouse sliding on my desk.)

Right Side

Off to the right I keep my iPhone. This reason is two fold: I tend to answer my phone with my right hand, and it is easiest to move when someone wants to come set papers down for me to review. That and the left side is really crowded as is.

Boring

On the face of it this is all rather boring to talk about, but the biggest revelation for me was using Notability. I’ve long used the app in meetings, but making a place for my iPad & stylus on my desk has really helped me keep working without trying to type one handed, remember things, or search for paper.

For me adding in the iPad in this way wasn’t obvious, but felt natural once I did it. It takes a lot of space on the desk, but just works brilliantly. I’ve tried many other apps, but I like the way Notability works, and so it stuck.

Most people like to keep a scratch piece of paper handy, and I truly do too, but I don’t like dealing with that paper afterwards. Using my iPad I get 85% of the way to that paper, with the added benefit of not having to deal with the paper after I am done with it.

I also find leaving the cover open, feels like it is an open notepad awaiting my scribbles. And yes, sometimes I just use it to doodle while on the phone — but I typically switch to Paper for that.

Mikael Cho recently moved to a standing desk, but found the experience short lived. Cho:

After two weeks, I was able to stand for about four hours a day, but I still needed to take multiple breaks. This was fine with me because I often need breaks throughout the day to refresh and maintain a good flow.
And:
If a standing desk works for you that’s great. But if it doesn’t, don’t force it — especially if it negatively impacts your work. Standing while working might not be for you. It wasn’t for me. And that’s okay. Standing for long periods of time isn’t much better than sitting anyway.

Cho gets really in-depth into the standing desk ideology, and what he has done in hopes of making his sitting desk situation better. Even though I don’t agree with Cho, this is an article that I think everyone who works at a desk should read.

That said, it is my opinion that he went about standing to work all wrong. At the beginning of 2011 I started standing full-time. I wrote my reasoning in that linked post, but you all know why already: standing is healthier.

But standing hurts right? Cho was driven nuts, my buddy Shawn Blanc couldn’t bear to stand all day (Shawn corrected me) much preferred to sit while writing, than he did standing. It’s a pain in the foot to stand all day. But only for a little while.

Like anything in life you have to ease into standing to work, and then even after that it will take a while to build up the strength to stand all day — trust me. It is three years later and I still stand to work, but even at that I get tired.

My journey to standing all day looked like this:

• Day One: stood for two hours, and didn’t get much work done. Finally sat down and just wanted to cry.
• Day Two: basically the same thing as day one for the next week.
• Week Two: Things were better.
• Month Two: I can now stand for about 6 hours a day, but more importantly I have finally broken the urge to sit down when I need to concentrate on something.
• Month Four: I stand all day, and can work effectively now while I stand. I still go home with sore feet and legs.
• Month Eight: The soreness is mostly gone and I can stand fine.
• Year Two: I can’t focus as well when I sit, and my legs/feet rarely feel sore. I’ve also ditched the anti-fatigue matt.
• Year Three: It feels weird, and too loungey, to sit and work.

In other words, it takes more than a year to fully adapt the standing habit. Think about how much you hated sitting a desks when you were a kid to work, but then you got used to it — now you are trying to undo all of that training.

The biggest issues you will face when trying to move to a standing desk are:

• Sore feet, knees, legs, and lower back. This is common, and is due to you not being used to working those muscles all day like this.
• Trouble focusing on detailed tasks while standing. You just aren’t used to standing and so standing itself is taking some of your concentration.
• People won’t get why you are doing it and will constantly remind you how comfortable sitting is.
• Your chair is right there — calling to you.

Standing all day isn’t easy, but I firmly believe that it is a lifestyle choice that will pay off in spades long-term. So, here are my top tips for getting started with a standing desk:

• Wait at least six months before you build/buy any sort of a permanent standing desk. There are tons of ways to build a makeshift standing desk for pennies. Just search around. After that you can get something nice, but I waited until just recently to buy and actual standing desk.
• Wear comfortable shoes, like athletic shoes, for at least the first month. Even if you can’t wear those for you job, bring a pair to switch into while working. Don’t try to go bare foot.
• Don’t be afraid to take your shoes on and off as you feel you need to do.
• Anti-fatigue mats are nice, especially if the floor in your office isn’t carpet.
• Your feet will swell, so be sure to wear shoes with laces so that you can loosen them.
• Don’t try to stand for more than an hour for the first week.
• Then, if I were to do it again, I would add 90 minutes to my standing time each week until I got to eight hours.
• BUT, break up that time in halves. Stand when you first get to work, and right after lunch. Sit the rest of the time.
• If you need to sit, sit. Don’t force standing, but also try to have enough discipline to hit your standing time goal each day.
• Marvel at how much shorter “meetings at your desk” are now that others are forced to stand too.
• Don’t eat while standing.

Most important: give it time. Six months in, you should have a good sense if standing is going to work for you, but it won’t be until about a year in that you are fully comfortable with standing.

These days I stand for about 85% of my working day and sit for the rest. If I am tired from the kids keeping me up, I just sit. There’s no reason to have my work suffer just so I can stand, but I still try very hard to stand as much as possible.

Even an hour a day of standing is better than no standing. Keep that in mind and go easy.

The biggest downside to standing is how much faster you wear our your shoes and socks. I go through socks like crazy now.

I’ve been using Writer Pro a lot since it came out, but recently found myself back in Ulysses III (a topic for another post). Recently though Writer Pro got a very important update, this update adds the first ever ‘night mode’ theme to Writer Pro.

It’s very well done, and very welcomed. I prefer to write fullscreen with a dark background, and so Ulysses always fit the bill there better. But this new night mode for Writer Pro has much better colors — it’s very well done.

(Luckily Ulyesses allows you to edit the themes it uses, so this should be a no-brainer.)

Either way, if you bought Writer Pro already you are really going to dig the new night mode.