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Tool update: Matt goes digital! Plus a few Mac productivity lessons

Since switching to Macintosh I've been trying out tools for GTD, playing with productivity tools, and generally being very pleased with the move from Windows. In addition, I decided to switch from my paper-based action management system to a digital one, and wanted to share with you results from both. I'd love to hear your Mac tips and tricks for productivity too.

Tools I switched to

In no particular order:

  • Contacts: I entered my ~1,000 contacts into the built-in Address Book program. Creating and editing using this program is painful [1], but well worth it: Address Book + Spotlight = fast. command-space, type a few letters, down-arrow (if necessary), hit return, ta da. Also, because Address Book is the inter-application standard for contacts, every program uses it for synchronization, so no other choice, really [2].
  • Calendar: I switched from a paper calendar to iCal, which went rather smoothly. iCal has importantly limitations, but, like Address Book, is usable. And again, it's the standard for inter-app communication of events.
  • Lists: Hand-in-hand with the calendar switch was my move from paper lists to electronic ones. Rapid list creation, search, and completion is central to the work I teach, so this tool choice was harder than the previous ones. Because the Mac attracts creative programmers (why is that?) there's a huge number of GTD-compatible programs available. I won't go into detail, but I found them either too complex or too limited. For me, Things showed the most promise. I'll give it another look after its release. As a result, I decided on a vanilla implementation using iCal's To Do feature, and the "one calendar per list" approach (i.e., creating separate calendars for actions, projects, etc.) Works well with some tweaks and add-ons [3], and led to a sweet little happy accident [4]. Same note re: iCal being the standard for task interoperability.
  • Portability/PDA: What good is a digital implementation without an expensive and fragile tool to take with you? Since Address Book and iCal are standards for synchronization, I had some flexibility. Sadly, unless you use an iPhone [5], you need to buy a third party program called The Missing Sync. In my case I bought a used HP iPAQ h4155 Pocket PC, which syncs, but in a "I'm not sure if it worked this time" way. Not great. Unfortunately, Palm sync support is at least as poor. Still, from a former paper guy, the two killer features are alarms, and all my contacts.

Other Mac productivity goodies

In addition to the "bread and butter" tools above, I found other great work enhancers, including:

  • Spotlight: Like Apple's initial "you have to buy a Mac for one feature" hit (desktop publishing) I'd have to say Spotlight almost justifies buying a Mac by itself. It has fundamentally changed how I use my computer - launching apps, finding files, and looking up contacts, events, and to do items. Apple absolutely hit this one out of the ballpark. And almost every program you buy integrates with the Spotlight database. Extremely powerful.
  • Quicksilver: Quicksilver is a Spotlight-like program that lets you operate on data (files, contacts, events, etc) in a contextual Noun Verb manner. For example, to send a file you'd invoke Quicksilver (control-option-command-space on my Mac), search for the file ala Spotlight, and select an action, such as "Email to..." There's a lot of potential here, but be forewarned: This tool is complex to set up and really get your head around. That said, there is one killer app that I couldn't live without: a very fast iCal front-end to events and to dos. More below [6].
  • TextExpander: After trying the major text expansion tools I found TextExpander to be the best for me. (I just use it simply for abbreviations - nothing fancy.) Does the job and works like you'd expect out of the box.
  • Screen sharing: If your mother uses computers, buy her a Mac. Why? In addition to "simple and works," iChat's built-in screen sharing is a tech support dream come true. Yes the same feature is available for PCs, but this is zero set-up, and easy to use. Plus, it makes for some great April Fools Day pranks. (Video chat's another argument for mom.)

Mac productivity tips

Finally, here are a few tips I've collected. Some are found elsewhere, but in case they're new to you:

  • Global: F11: Your single-key "get focused" tool. Hides all windows and shows just the desktop. Great if you're on the phone and want to work on the project in front of you, or avoid EMV (E-Mail Voice - see Overly Wired? There's a Word for It, from CrazyBusy). Related: option-command-h (hide others). More shortcuts here.
  • Global: command-shift-/: This is a very cool UI trick, and allows you to search menu items without knowing which menu they're located in. Hit the shortcut, type part of a menu item, down-arrow to it, and hit return. Bonus: Slick animation + you can see the direct keyboard shortcut for next time.
  • Firefox: command-return in find mode: This took forever to find: When in find mode (command-f), command-return toggles the "Highlight all" button.


  • [1] I find Address Book usable but frustrating, esp. for creating and editing. I ranted a bit about it here.
  • [2] I looked at Entourage 2008, but found far too many enough issues to decide against it, in spite of a strong integrated feature set.
  • [3] iCal lacks a list-based "control center" that shows today's events + To Dos. I worked around this using Dashboard and two widgets: iCal Events and DoBeDo ToDo. Side-by-side they give me an interim solution. For rapid entry, see the Quicksliver section above.
  • [4] When I printed my to dos I accidentally got them in random order. After a short "crud" moment I realized this was good: It made me look at each one fresh, a kind of "enforced" daily review. A keeper!
  • [5] I'll no doubt get one, but not until a) they support Verizon (best service in my area), and b) they get To Do lists (!), something everybody's speculating about.
  • [6] I searched pretty hard for a smart command-line front end to creating events and to dos - rapid capture is crucial to maintaining focus, and keeping lists up-to-date. The closest I've found is Quicksilver's iCal support. To create an event 1) invoke QS (control-option-command-space on my machine), 2) type "." to enter text mode, 3) type the to do or even text in compliant format (e.g., "tue 2pm call matt"), 4) type tab, 5) type "ev" or "to" to get to get "Create iCal Event" or "Create iCal To Do", and 6) type return. Not bad, and a big improvement over using the mouse in iCal. More at How To: Add a new iCal event from Quicksilver.

Reader Comments (11)

Please consider trying my custom php/mysql GTD program! I'd be happy to set up a demo installation for you and let you noodle around with it. My wife has been using iGTD with iCal and her palm on Mac OS X and finally had enough. After one day of using my program she was elated.

I'd also be happy to walk you through it. Unfortunately, it won't really sync with your handheld, though I do have a mobile web interface for it. If syncing is a must-have, it won't do the trick.

April 21, 2008 | Unregistered CommenterBrock Tice

Thanks for the offer, Brock. Sounds like a powerhouse. Syncing is definitely a requirement, though. Thanks for your comment, and good luck!

April 21, 2008 | Unregistered Commentermatthewcornell

This was interesting to read, since I switched from Entourage to Address Book and iCal when Spotlight came out. And some of the items in your Address Book rant frustrate me, too - but not enough that I'd use anything else.

I'm still looking for a list answer that I really like. (One of the items on my list is to try out some of the many options I know about!)

And here's a request for the details about your concerns with Entourage 2008.

April 21, 2008 | Unregistered CommenterJeri Dansky


I would definitely check out www.circusponies.com Notebook. It has sync with iCal and AddressBook capabilities and is just an all around amazing digital InBox.

I also really like MacJournal from http://danschimpf.com/.

Good luck with your GTD.


April 22, 2008 | Unregistered CommenterMarshall Huwe

Thanks for your comment, Jeri.

some of the items in your Address Book rant frustrate me, too - but not enough that I'd use anything else. Ditto. I think entering 1,000 contacts pushed me over the edge, but now they're relatively minor annoyances and I know how to work around them.

And here's a request for the details about your concerns with Entourage 2008. Thanks for asking. Now that I think about it, it's more a lack of trust of Office and Microsoft in general. For example, I wasn't comfortable allowing Engourage access to iCal and Address Book - synchronizing wasn't consistent when I tried it. Also, I was worried about corruption (during sync) and getting locked into Engourage. I suspect I need to re-evaluate it. It's got a nice array of "one stop" features, including calendar, tasks, and projects... Please let me know if you work with it.

April 24, 2008 | Unregistered Commentermatthewcornell

I appreciate the pointers, Marshall. I did briefly try Notebook2 and a bunch of others, but ended up not blown away by any one in particular. I'm tough to please, though - I have specific ideas about how a note-taking program should work. Links should be central, for example. The coolest little program I found is [ VoodooPad | http://flyingmeat.com/voodoopad/ ].

What's great about the Mac is there's such a wide variety of programs in this genre.

Thanks for reading!

April 24, 2008 | Unregistered Commentermatthewcornell

An update re: Entourage: As my edit above shows, I was too hasty in my assessment. Here's what I told a reader who emailed me:

I went back to give it another look after I realized my assessment was too uninformed. The biggest issues for me are synchronization with the built-in tools - Address Book and iCal, and a general lack of trust of Microsoft programs. I've already had to remove and re-install to get the updater to work, and crashes do happen. There's a user-based support forum that's active, which helps offset the issues a bit. That said, the integration of email, tasks, calendar, projects, and people is compelling. In the end I went with the basic tools. Doing this reflects my desire to keep it simple, and to do a bit of science: Controlling how much I change at once.

April 24, 2008 | Unregistered Commentermatthewcornell

I devised an approach at http://www.gtdagenda.com, and you are welcome to use the application.

You first need to set Goals in each of your life categories. Although David doesn’t call them categories and goals, but “levels of focus, altitude views, areas of responsability etc”, it’s the same thing.

Then you create Projects in each goal, these being sub-goals that when completed move you forward to the completion of the goal.

Then you have Tasks, actionable steps in each project. Here you can set the famous Next Actions, and also associate the tasks to your Contexts.

Checklists section is great for your repetitive tasks (daily, weekly, monthly or yearly). It generates a series of checkboxes and you check them off as you do the tasks.

Schedules are for the scheduled blocks of time. Even if GTD does not promote scheduling we all have schedules (at work, at school, self-imposed etc). The activities here can be associated with the existing projects.

Calendar section is for events that need to be done or remembered of at a specific date.


April 26, 2008 | Unregistered CommenterDanGTD

Dan, I really like the coverage of GTD, and your solidification of the goals "missing link." Well done, and thanks for the comment.

April 26, 2008 | Unregistered Commentermatthewcornell

Hi - great article and thought I would share my experiences.

I've been playing with QS for a while to quickly create iCal Events and ToDo's since I got made redundant and no longer had my office Outlook synching with my iPhone. Despite some limitations, iCal ToDo's work very well when you use the Events at the same time and are MUCH more visible to use than ToodleDo which I was using previously synched with Appigo's ToDo which also now has a free iCal synch tool.

Anyway, as you probably know, the syntax you need to use in QS is:
priority subject - US format date hh:mm am/pm

Personally I found this quite frustrating to use as it would always go into the last calendar and also required a number of commands to bring up. I tried assigning a trigger but it never worked quite how I wanted it to. Whilst trying to fix this I stumbled across the TUAW article on Automator and creating your own .apps which are actually workflows. I used this to create 2 workflow apps, one for new ToDo and one for new Event, which both bring up the relevant dialog box without requiring iCal to be running. Next I used QS to assign triggers to each app, so now I have CTRL+ALT+E for New Event and CTRL+ALT+T for New To Do. Works like a charm!

Oh and one last productivity tip - you can tell QS to use a double-tap on any of the modifier keys (Command, Control, Caps Lock etc.) instead of a key combo such as CTRL+SPACE or whatever. I personally went for Command double-tapped which works wonderfully especially as I also have "Hide if already visible" also enabled - double-tap to open and again to close. So far, no accidental openings have occurred.


January 21, 2009 | Unregistered CommenterGingerNinja

I like that Appigo's ToDo syncs with iCal (looks like it's pending Apple approval) and your Automator/QS workflow - slick. Ditto for the QS double-tap; I didn't know about that. I appreciate your reading, and for the citations :-)

January 22, 2009 | Unregistered Commentermatthewcornell

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