Over the past ten months I’ve been using a variety of To Do management applications to solve my personal task management woes. This blog post is a recap of the four best contenders that I have found, where they succeed, where they fail, and what needs to be on the table for me to be happy.

Laying the Ground Rules

As the lead UI designer behind our group task solution Stacks I can be a pretty harsh critic on things that don’t feel or work right. Also along this same line, I understand the difficulty of developing a product and trying to meet feature requests. It’s impossible to keep everyone happy, not to mention build features with time and care. For some of these apps the features I want might be coming, for others they aren’t part of the ballgame and never will be. I get that, but let’s still “talk it out”.

Required vs. Nice to Have

Must have:

• Well designed interface
• Quick task entry
• Repeating tasks
• Time based notifications/reminders
• Access to tasks at all times (ideally: mobile, desktop, ipad, and web)
• Cloud syncing

Nice to have:

• Categorization of tasks (long term, work, personal, etc.)
• Notes or sub-tasks
• File attachments
• An API
• Great keyboard shortcuts

Alright, let’s jump into the four selected contenders and see what they’ve brought to the table.

Simplenote

Done Well:

phenomenal cloud syncing, quick task entry, access to tasks at all times, notes/subtasks, an API

Lacking:

repeating tasks, reminders, categorization, great keybaord shortcuts

At first I felt a little bad including Simplenote as a task management app. The truth is that Simplenote was never meant to soley manage tasks. That said, it’s just too good at what it does to not have it on this list. First off, Simplenote is bar none the best cloud syncing application I’ve ever used. It’s never once lost my changes or updates and I’m using it on my computer, iPad, and iPhone. Also, in a pinch it has a web interface (that doesn’t suck) as well. On top of this it has an API (although it’s not fully public yet) which has allowed developers to tackle the interface in unique ways. For instance, Just Notes and Notational Velocity are independent apps that work great with the Simplenote API.

There are a few big hurdles you have to be willing to accept with Simplenote. First, it won’t be able to send you reminders in any way shape or form. This means you have to remember to check it to see what’s due. This became a deal breaker for me after a few months, but if you’re the type of person who’s disciplined, this may not be an issue. Second, Simplenote has no way to repeat tasks, so all those CC bills and monthly reminders need to be created every month.

If all you’re looking for a is a small To Do app that also has great note taking capabilities Simplenote is probably your best bet. Beautiful Helvtica type, a super clean and fast interface, and very proactive developers. If you need more than just a few lines of text, like me, then it’s onward to the next app.

Things

Done Well:

quick task entry, categorization/tagging, nice interface, access on multiple devices

Lacking:

Repeating tasks are terrible, badge only notifications, no cloud syncing

Things is perhaps the most well known Mac and iPhone task management solution. Culture Code, the creator of Things, has been featured on Apple’s developer site and has done well in a number of reviews. From the surface Things looks like a winner. Beautiful icon and interface, multiple device support, plus tagging and categorization. Yes it is expensive, $50 desktop + $10 iPhone + $20 iPad, but that’s sometimes worth it for a great experience. The problem is that Things felt off the whole time I used it. It’s not that it doesn’t have a few great features (ie: quick task entry via hotkey on the desktop version) but rather that the deep features trail off. The features that should be most thought out don’t seem to be at all. For instance, let’s look at creating a scheduled repeating task:

First off, the entire due field is uneditable so why does it even allow typing? Second, the wording is just ridiculous, ‘copies are due’ could just be ‘this task is due’. Further, why at the bottom do I have to say each copy has a due date, didn’t I just specify that up above when I said the day it’s due? Granted, maybe there is someone out there who needs to randomly assign tasks every month, on a given date, and doesn’t actually have a date that task is due. But really?! Even so, Culture Code should spend some time wording this better, as it is now it’s just insanity. Check out some better solutions that other developers created:

Second, Things doesn’t have cloud syncing. For an application that is meant to exist on three different devices it is extremely weird that there is no cloud connection. Instead, you have to have each device’s wifi on and then let them sync over a home/business wifi network. This, in my opinion, is a recipe for disaster. Router and wifi questions aside, what if I add 7 tasks on my laptop but am connected via ethernet, then take just my phone out of town for the weekend? My data is completely inaccessible. For a $50+ dollar set of apps I expect cloud syncing, even for a yearly cost.

Third, Things isn’t very good at reminding you about tasks. It shows you a badge of how many tasks you have but beyond that you have to go in and look at your tasks on a daily basis. Maybe some people do this but I don’t. Let me specify a time to be reminded and then show me an alert on my phone, simple enough?

End game, Things just doesn’t stack up for the price. If Culture Code works on usability and wording, allows cloud syncing, and gives a discount to users that own all the apps I’ll consider it again.

NotifyMe 2

Done Well:

beautiful mobile interface, push reminders, categorization, task notes, price

Lacking:

web interface might as well not exist, no desktop version, no API

NotifyMe 2 is the most recent application that I’ve been using. While it lacks a desktop client (which is a huge downfall) the mobile client is extremely good. The biggest and strongest pitch for NotifyMe is exactly what it’s name says: notifications. NotifyMe syncs your tasks to the cloud and then sends a push reminder to your phone when the task needs to be done. At that point you can either snooze it and be reminded later (at an interval you set) or check it off. Additionally, repeating tasks on NotifyMe are better than any other interface I’ve seen – especially considering it’s a mobile interface. You set the date and time the task is due, then how often it should repeat, you can do alternate weekdays, weeks, months, or years. Or, something like remind me every 45th day. The best part about this is the ease with which it works. You can tell the crew at PoweryBase sat down and really went through the steps.

Among the other nice things in NotifyMe are task notes and task sharing. Task notes are placed nicely within each task, a small icon appears next to tasks that have notes letting you know additional information exists. This seems small but the ability to add a few notes into a task is huge. For instance, I add a task to set up a doctor appointment easily, but remembering to bring my new insurance card and the new office address could be just as important. The ability to have notes fixes this problem. Additionally the app also has a sharing and friends feature. I haven’t tried it enough to know how well it works, but if it works as advertised (and I assume it does based on the rest of the app) then it should be a hit for married couples or families. The ability to assign notifications to others on the fly could be extremely useful.

The biggest knock against NotifyMe has to be their application web interface, webapp.notifymecloud.com. In fact, let’s be honest, it doesn’t even deserve to be called a web interface. It’s more like a pile of trash sitting online that is meant to somehow duplicate functionality of the mobile app. And, while technically it has the functionality, the feel and care of the mobile app is 100% absent. The icons are gross, the corners of the containers are rough and thrown together. The task fields are unstyled and unorganized. It’s literally like someone went into Dreamweaver and inserted a bunch of default text fields, added some terrible icons, and said “that’s good, I’m done”. The fact this application is so bad makes me terrified that PoweryBase doesn’t take their design seriously. If they are willing to put out something this bad on the web who’s to say the app might some day slip into the same void. Terrifying.

In conclusion, NotifyMe 2, from a mobile perspective, is the best task manager I’ve seen. This is big because if there is any place to have a great app it’s on the device that’s always with you. Sadly, the web app is not worthy of discussion. It’s unusable and beyond in a pinch circumstances, worthless. Let’s hope this gets addressed so I can give NotifyMe 2 the clear victory in the To Do application space.

The Hit List

Done Well:

best desktop experience of any app I have ever used, great keyboard shortcuts, tagging/categorization, extremely fast task creation, repeating tasks

Lacking:

vaporware iPhone version, an API

I’ve never been as excited about a program as I was about The Hit List. It’s beautiful, fast, easy to learn, and incredibly well thought out. Sadly two years into the product life cycle the announced iPhone app has never been released and the desktop version has never come out of beta. The developer has dropped off the face of the earth. While the desktop version is truly a marvel to be seen (even in beta), the lack of syncing, API access, or a mobile version render this app a dinosaur. Some people have gotten it to work with the 2Do via calendar syncing, but I’m just not willing to use some hack method for important tasks in my life.

Because I’m such a fan of The Hit List I believe it belongs in this showdown. For someone that only needs a desktop application there is nothing better on the table. Just check out this quick video I whipped up:

If The Hit List gets an iPhone app I will jump on it no matter what the cost. Though I’m a realist and therefore betting this app, sadly, won’t see the light of day.

The Final Conclusion

Considering it’s mid 2010 I’m astonished that someone hasn’t solved the GTD personal task solution in a way that meets the few goals I provided above. There is a lot of potential in the market but no superstar. I’d love to hear other people’s solutions to the GTD problem, maybe something’s out there that I don’t know about. Until then I’ll keep hoping for a better desktop or web version of NotifyMe2. Or, even better, the mystical unicorn Hit List iPhone application from Andy Kim.

Over the last several years I’ve tried a number of different approaches to make my day to day life more manageable. And, while I’ve found nice solutions for most challenges I deal with (remembering contact info, keeping appointments and meetings, managing tasks) I’ve still had one giant void.

A clean and easy way to take down and synchronize notes.

In my book a notes app only needs three things:

1. A nice simple mobile interface (this includes a nice typeface, ie: Helvetica.)
2. An easy way to access the app from any computer or device.
3. Easy and instant synching between mobile devices, computers, and the web. It’s only text after all!

In essence, let me write and access notes from anywhere without getting in my way.

For a while I tried to use Apple’s default Notes application. And, to be frank, it was one of the worst experiences I have ever had using an Apple product. For one, the Notes application is absolutely hideous. Second, it requires me using Mail App to manage notes from my computer. Now, I don’t know if you have ever used Mail App to do anything, but it sucks. It’s slow, clunky, and especially frustrating to use if you aren’t working with basic email.

Beyond just the default Notes app I also dabbled with EverNote. Now, to be fair, EverNote seems like a good application for certain uses. The problem I have with it is that it tries to do too much. I don’t need photos, voice notes, text transcribing, or any other of the other options it offers. The more options provided the more things to get in my way.

A Simpler Way

About a month and half ago I decided to start using Simplenote, a small, extremely simple, note taking application for the iPhone.

On top of a wonderfully simple interface Simplenote also has API access for third-party developers. This means there are several options for desktop based note applications. My personal choice is JustNotes, although I’ve also installed and used Notational Velocity and it’s a great choice as well. If you’re a dashboard fan you can try out DashNote.

The final benefit of Simplenote is website access your notes. In essence, allowing you to gain access to your notes from any computer on the web. While I don’t use this often (I always have my iPhone) I like the peace of mind it provides.

Over the last month and half simple note has drastically changed the way I record and access quick bits of information. It’s managed to squeak itself onto my iPhone’s home screen and even has a global shortcut on my Mac. I couldn’t be happier with the implementation.

As a long time user of OS X I’ve tacked on application after application to handle small, but essential, tasks.

Fluid for running my calendar and Stacks, JustNotes for syncing with simplenote, The Hist List for personal tasks, Quicksilver for application launching, and xScope for Web Development quickies.

Each of these applications has the option, and generally encourages, the use of global shortcuts. For those of you that don’t know, a global shortcut is a keyboard shortcut that can be can be used system wide.

The main advantage of this is the ability to access common features or tools without having to switch apps (i.e. switching songs in iTunes). However, many applications have default shortcuts that get overwritten by the global alternative. For instance, a common shortcut in Photoshop is cmd-option-d which is used to feather a selection. Yet, in OS X, trying to use this results in the dock getting hidden.

The best way around this issue is to create custom shortcuts for things that have conflicts or need quick access. However, before diving in and going crazy — “uh.. what did I set that shortcut to? *Click*click*click*, oh, right, cmd-option-shif-ctrl-F3″ — follow a simple framework to avoid headaches . Here’s what I recommend.

1. If possible leave the standard program shortcuts in place. This makes for less hassle down the road if you ever have to reinstall the OS or use multiple machines for task (i.e. a school computer lab).
2. Make all program based shortcuts cmd-ctrl-LETTER. To date I have not found any program in OS X that by default uses cmd-ctrl-LETTER shortcut’s. The first advantage to this is that you don’t have to worry about overwriting already-in-place shortcuts. Second, and most importantly, the cmd-ctrl keys are super easy to reach and use.
3. For custom global shortcuts use a standard. Preferably cmd-option-ctrl-LETTER. Similar to the last bullet, I have never found a pre-set shortcut that used cmd-option-ctrl-LETTER. Yes, it sound like a lot of keys, but it’s three right in a row and they’re easy to reach.

The point is, if you standardize pre-set, local, and global shortcuts you’ll never have to worry about the key combo, all you’ll have to do is remember the letter or number you used. Further, it’ll keep conflicts at a minimum and give you a lot of options for growth down the road.

I’d love to hear other tips on what people are using so don’t hesitate to comment with your suggestions.

1. We are extremely lucky to work in the industry we do. By having everything online, it’s just silly to not be able to work from home. When you have a group of trusted individuals who get their stuff done and are accountable for it, it is such a nice benefit to work from home. I find it funny with micromanagers in a big corporation who think working from home is an excuse to slack off. If that’s the case, you’re clearly not doing something right. But, micromanaging rants can be saved for another blog post.
2. When 2 of the 9 people in your office have swine flu, you can avoid them. Plus, you don’t actually have to take sick days. It’s so nice to stay home when you’re not feeling well, but still be able to get your work done and not cut into your vacation or personal time.
3. Fresh air and change of scenery. Everyone can use that.
4. It tests communication skills. Are we working in the most collaborative way? Does the weakness show more when we’re out of the office? If so, what do we do to solve the problem?
5. Nooners. Kidding. I swear.
6. It helps put work life vs. personal life in perspective. Some things that tend to stress me out when I’m in the office just aren’t that big of a deal and aren’t worth adding the extra years to my life. It’s good to get that periodic reality check.
7. Pajamas. Enough said. Well, not really. You also don’t have to put makeup on or do your hair…until George surprises you with a video chat. Course, it’s worse when he does that during #5. Ah, kidding again. Really.
8. For some reason, I feel like I can take a step back and become more strategic. I have the time to look at the big picture, our process, client goals, etc. I’m not sure why, but I do. Maybe it’s because I get to dodge phone calls for a day, and really focus on some of my own goals.
9. Healthier lunches. I LOVE going out to lunch with my colleagues. It provides a much-needed break in the day, and is a great time to talk about our shenanigans outside of work. However, with that comes lunches that are much larger and much higher in calories. I know, I know. With some discipline I’d be better when at work, but where’s the fun in that!?! At least when I’m home, I have a damn good reason for staying home to eat.
10. Everyone’s super duper excited to see you when you get back. It’s just one big love fest. Seriously.

What did I miss? What are you favorite things about working from home?

I’ve learned two valuable lessons recently: Don’t be lazy. Don’t be a brat. More specifically: add a subject line to your e-mails. It’s not that hard and it makes everyone’s life easier.

When I first started at Imulus, I was not accustomed to inter-office exchanges of e-mails. Most of the time if someone wanted me to complete a task, I would attach the completed item to an e-mail and send away. Naturally I would ignore the prompt asking me if I still wanted to send the e-mail without a subject line. After a while, my mail application would give up on me and stop the alerts.

Eventually, I was diplomatically informed by some of my co-workers that my neglect of subject lines may be a tad annoying. “Annoying?” I thought in my most indignant mental voice. “I’ll show them annoying.” After this cerebral conversation with myself, I proceed to add subject lines that had nothing to do with the actual e-mail. Subjects such as “sweet cuppin cakes” or “I like turtles” would crop up in my co-workers’s inbox giving them something to chuckle at or be irritated at.

My shenanigans ensued for around a year and a half until the day that cruel irony bit me square in the ass. During a dark day in Imulus’s history when we lost some information, I was doing my best as the diligent designer to help recover all that I could. This meant I had to look though old e-mails with my trusty search to help me. Side note: I am not a good organizer when it comes to my e-mail and I am a digital pack rat – bad combination. Anyway, back to our flustered heroine. As I was sorting through my old e-mails becoming increasingly murderous towards my past self I came to a harsh revelation – it’s not worth it. It’s not worth the inconvenience for maybe a couple of seconds of giggling at the silly subject line.

These days I have learned my lesson… Although occasionally I do like to slip in the old silliness, but only if it applies to the real subject line.