Through many years and many computer systems, I’ve always been the sort of person who likes to tweak and customize my setup. I’m not happy just to make do with the programs that come preinstalled or shipped in shrinkwrap. I acknowledge a point of diminishing returns in this sort of thing, of course; I’ve never taken the effort to learn how to use Linux, for instance, or for that matter even to dip into Terminal on my Mac… but I do like to be able to do my own basic troubleshooting.  I don’t script my own utilities… but on the other hand, I do know how to dig up, install, and use custom scripts created by others, whether I use ’em through Automator in OS X or through Greasemonkey in Firefox or what-have-you.

Nor have I ever had the inclination (or money or time) to be an early adopter of every new thing that comes along… but that just makes it all the more important to put in the time and effort to properly research and configure my choice of tools and workflow when I do make a change, because it’s probably something I’m going to be sticking with for a while.

So I’ve always been in sort of a middle ground… I’m by no means a Power User compared to the kind of folks who post on SlashDot, but OTOH I am one compared to probably 90+ percent of day-to-day computer users.

With all that said, one might imagine that finding a way (in the course of my latest nearly-from-scratch rebuild of my system) to handle basic PIM functionality wouldn’t be that big a deal, right? After all, managing data like contacts, calendars, and to-do lists is at the very heart of what people do with computers, and there’s been user-friendly software for the purpose for over 20 years. You’d think finding a solution now would be a no-brainer.

Think again…

Here’s what I want to be able to do: I want to be able to record and organize the contact information for people I know; my calendar of upcoming events, appointments, and activities; and my list(s) of important tasks and projects; and to integrate all that information in a single, user-friendly interface. I don’t think it’s that much to expect:  after all, I was doing all of that quite happily back in the early ’90s with DayMaker.

Granted, things are a little more complicated today, since a lot of us expect to be able to carry that information around with us on our various “mobile devices.” (A term which always sounds a bit risqué, IMHO… but I digress.) Then again, that’s not exactly new either, and Palm managed to pull it all off reasonably elegantly by the time the late ’90s rolled around.

Today, though? Things really seem to have regressed. Let me tell you what I had to do.

(Some of this I’ve covered before, some I haven’t, but let me take it from the top.)

First of all, Mac OS X runs something called “Sync Services” behind the scenes, which is supposed to coordinate all of this information. It’s automatically tied in with Apple’s built-in programs — Mail, iCal, and Address Book (and thus, through iTunes, with Apple’s built-in iPhone apps, Contacts and Calendar)— but third-party developers are allowed to tap into it as well.

That’s good, because as much as I love my Mac and its OS, I really don’t like Apple’s built-in programs these days. They suffer from ugly and inconsistent visual design, their feature sets and configuration options are painfully limited, and data input is unnecessarily cumbersome. (Just for the record, on the Windows side, MS Outlook sucks in lots of ways too.)

As I’ve discussed earlier, I wound up settling on Entourage 2004 (a Mac-only part of the MS Office suite) to handle my e-mail. It posed some complications in terms of backup, and it does have a tendency to crash arbitrarily from time to time, but at least it always gets back up and running without losing data or causing any larger problems. As it turns out, I’m also using Entourage for contact management, since it can be configured for an automatic two-way sync via Sync Services, and thus with my phone. In addition, I’ve decided to use a free account on Plaxo to keep all my contact info available online, just as a safety measure. (Plaxo also ties into Sync Services, and it allows me to import data from other sources like LinkedIn as well… plus, contacts who are also Plaxo members can self-update their info.)

I don’t use Entourage for calendaring or task management. Its functionality in these areas actually isn’t too bad, but unfortunately Microsoft uses the (IMHO sensible) approach of designating categories for events and tasks, whereas iCal (and thus Sync Services) sort them into “calendars,” with each item able to live in only one calendar. And categories don’t map to calendars, so any and all Entourage items would lose their categories during the sync process and land in a single “Entourage” calendar in iCal.

Instead, after much waffling and weighing of alternatives, I’ve settled on using BusyCal for calendaring. It’s designed by the guys who worked on Now Contact and Up-to-Date back in the day. Its interface is similar to iCal (right down to the multiple-calendars thing), but it’s more polished in several ways:

  • It does a seamless two-way sync with Google calendars, rather than merely subscribing like iCal
  • It allows data entry in a sidebar box rather than an annoying modal window, and understands intuitive entries like (e.g.) “7p” for 7:00 pm rather than requiring you to tab through each element of a time setting
  • It includes a List view along with Day, Week, and Month
  • While it doesn’t technically allow multiple categories, it does allow you to assign tags to items (unlike iCal), which is almost as good
  • It puts task items with deadlines on the calendar itself, where they logically belong, rather than isolating them in a separate list (like not just iCal but Entourage and Outlook)
  • It understands recurring task items (e.g., balance your checkbook each month)

None of these features is exactly revolutionary, but for whatever reason neither Apple’s offering nor most other competitors include them these days, so BusyCal wins by default. I sync most of my BusyCal calendars to my Google calendar, which I otherwise don’t touch—it’s just there for online backup, and to facilitate sharing (a couple of specific calendars) with my girlfriend’s Google calendar, sparing us some duplicate data entry.

So far, it’s all still fairly simple. Beyond this is where I started having to draw up charts and diagrams.

BusyCal has decent task management features, but not great ones… and what’s worse, there’s no way to get them onto my iPhone, since neither Sync Services nor Google Calendars map them correctly (with recurrences, etc.) to any existing iPhone app. (Indeed, Apple’s sad little built-in Calendar app for the phone doesn’t even include a Week view, never mind to-do items.)

There are lots of different viewpoints about how best to handle task management. One of the trendy approaches these days is called “Getting Things Done” (GTD), which to make a long story short allows you to process and sort tasks quickly by a number of different kinds of descriptors—Context (e.g., where you do it: Phone, Computer, On-the-go), Projects (with subtasks), Areas (e.g, Family, Work), Deadlines, and more. I haven’t bought the book or become a diehard devotee, but because GTD is trendy a lot of programs in recent years have been designed to accommodate it, so it was really impossible to compare programs without at least learning the basics. The thing is, different programs implement this basic schema in very different ways.

The ne plus ultra of this sort of thing is allegedly OmniFocus, but the price is ridiculous. Two other popular programs are Things and The Hit List, and I tried trial versions of both, but quite simply didn’t like them. They’re desktop programs, and they have the advantage of being able to sync with iCal (although function mapping remains a problem), but I just didn’t care for either user interface (UI). Hit List is technically still a beta, and IMHO it shows. EasyTask is another desktop app that I liked rather better (and it’s also only $20), but its feature set just didn’t quite measure up… so I turned to online “web app” alternatives. Two popular contenders there are Remember The Milk and Toodledo, and I chose the latter. In fact, I strongly recommend it to anyone looking for robust, customizable task-management functionality. RTM has a more attractive UI, but it’s anything but user-friendly. Toodledo’s UI is frankly ugly as sin, but it’s at least fairly logical and possible to figure out with modest effort. And it rewards that effort, because Toodledo is a very feature-rich application, allowing you to organize your tasks in almost any way you can imagine.

It also has several other advantages:

  • It’s completely free (a $15 annual subscription brings some extra capabilities, but more bell-and-whistles than anything essential)
  • It has a handy Firefox add-on that allows for quick data entry and lets you view and sort  your list(s) in a sidebar
  • It can synchronize with no less than three competing iPhone apps

Those iPhone apps are the native Toodledoo app ($3), Appigo’s ToDo ($10), and Pocket Informant ($10). After comparing trial versions, I decided that Pocket Informant has everything I wanted, in an attractive interface, and with a dedicated and responsive developer behind it to boot. In a single app, it integrates both calendar and task management features either of which on their own are better than most competing products. It’s easy to use and highly customizable. It can do automatic cloud-based syncs with Google calendars and with Toodledo, and it matches them feature-for-feature with few if any awkward feature-mapping kludges.

Frankly, this $10 iPhone app does practically everything I was looking for in a desktop app, but couldn’t find. I can’t help thinking that a lot of desktop software developers should be ashamed of themselves… starting with Apple.

My main complaint here is simply that Toodledo is a web app. I’m not a big fan of web apps, since they live in a browser, rather than on my desktop. It’s possible to break it out into a simulated desktop client that runs in a “site-specific window” and can have its own Dock icon, using a utility like Fluid (with a Safari runtime) or Prism (with a Firefox runtime), but that’s still a workaround, and still requires me to be online to use it.

So, at the end of the day, the setup I’ve worked out is this (take a deep breath!):

My contacts (in Entourage) and calendar events (in BusyCal) sync through Sync Services to AddressBook and iCal (which I don’t actually use), and from there through iTunes to the Contacts app on my iPhone (as well as the Calendar app, which I don’t actually use). They also sync via the internet to Plaxo and Google Calendars respectively (allowing me to share and synchronize data without actually using those interfaces… unless I happen to find myself at a remote computer, in which case the web access is handy). Meanwhile, my tasks (in Toodledo) sync automatically with Pocket Informant on my iPhone, which integrates them with the calendar info it syncs from Google Calendar.

Simple, right? 🙄

(Right now, the main downside to all this is that Toodledo doesn’t sync with Sync Services, so I can no longer get at my task items in BusyCal. I can subscribe to them via a webdav link, but that’s a one-way thing; I can only view them, I can’t actually make changes in BusyCal that will be reflected in Toodledo. However, the makers of Pocket Informant promise that a future update of that app will allow WiFi syncing with iCal (and thus likewise BusyCal)… so assuming they work out the feature-mapping issues to get around iCal’s deficiencies, I may soon be able to achieve that two-way relationship through the other end of the sync chain.)

It works. Pretty much, anyway; I can get at my data when and where I need it, and I haven’t run into any significant synchronization dropout or duplication issues. It requires me to use a lot more programs than I’d ideally prefer, though, and the only place all the data is really integrated is (IMHO ironically) on my phone, which is of course the least convenient place for data entry.

Moreover, figuring out what to use and how to set it up took no small amount of time and effort, as you might surmise. I didn’t entirely mind that commitment, for the reasons I described at the outset. I have absolutely no idea, however, what the “average user” is supposed to do who just wants to be able to take the kind of data he/she used to jot down in a Filofax back in the day and use his/her computer(s) to keep track of it, without having to pursue a friggin’ degree in the subject.

(Side note: If I were trying to run a small business I’d probably look into the DayLite CRM/time management suite, but that’s a full client-server solution with a price to match, so it’s overkill for an individual.)

This sort of thing ought to be easy and intuitive. Seriously. Someone is missing a major business opportunity here.

Then again, if some new offering really does leapfrog my customized setup, I’ll probably sulk in a pool of buyer’s remorse for all my wasted time and energy…

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3 Responses to “On PIM software and life as a “Power User””
  1. I don’t know whether it’s just me or if everyone else experiencing issues with your website.
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  2. Sometimes I sympathize with the “average user,” sometimes I don’t. A lot of that depends on whether someone’s at least willing to look under the hood, as it were. Otherwise they’re like the people who buy an expensive HDTV because it looks nice in the store, then take it home and plug in old-style AV cables and never calibrate the color.

    Anyway… as to UIs, I think this is one of the ways the Internet, love it though I do, has been a mixed blessing. Back before the mid-90s, your computing experience was limited to programs actually loaded onto your own computer (or, at least, your office network). The technical capabilities of the end user’s system were therefore fairly clear to developers, as were the UI guidelines of the OS in question… leading to quite a few programs that were simultaneously very capable, very attractive, and very easy to use. (Even earlier versions of Windows, for all its clunkiness, had better UI integration than current ones… including among MS products.)

    With the advent of web browsers, though, everyone who could put up a web site got to invent his or her own interface for visitors, from scratch. Moreover, there were a wide range of users with different kinds of systems and software who would all be accessing those sites, so there was literally no single model to which to adhere anyway. (The best one could point to were HTML standards, but no browser has ever actually been completely standards-compliant anyway.)

    The best developers brought their UI design skills with them from earlier days, and created sites that could be capable, attractive, and intuitive for a wide range of visitors, even while keeping up with evolving Web technologies. The other 99.5%… didn’t.

    Of course there are always pluses to balance the negatives. The ‘net enabled the whole open-source movement, which has made it far easier than it once was to get good, affordable software at little or no cost… and for that matter to try it before you commit. (Yes, shareware existed in the pre-net days, but actually getting it was frequently more trouble than it was worth.)

    I’m not sure what the long-term effects of the iPhone’s App Store will be. It’s a fascinating hybrid of a development environment that’s simultaneously closed (a single hardware platform; Apple’s control of distribution) and open (anyone and everyone can develop for that platform, and their work is easily and often freely available). At this particular juncture, though, I’m not so concerned about how the iPad might change this as I am about Apple devising some improved interface just to help sift the wheat from the chaff within the App Store…

  3. RAB says:

    The failings of Apple’s bundled apps are all the more irksome when one considers that folks like us — with any inclination and/or skills to wade through all these third-party alternatives — may be a shrinking percentage of the growing Mac user base. The majority of new users see there is a mail app, there is a calendar app, they don’t have to pay extra for those…so they’re not inclined to investigate something they might have to pay for…if they even knew where to look for one. They might never even realize the user experience is bad if they haven’t known something better.

    (Despite its controlled nature and its many failings for developers, the iPhone app store has been a real force in getting shareware in front of users and encouraging them to try stuff out.)

    I’m glad you mentioned the weakness of the UI on most of these: that’s one of my biggest frustrations. I’m really hoping the next OS X update is going to take some visual cues from the iPhone OS and that Mac developers will start learning from design successes in that area. That said, maybe the greatest blessing of the iPhone in UI terms is the discipline required by the tiny screen real estate, forcing designers to cut what doesn’t work. It’ll be interesting to see if iPad apps stay as relatively clean, or if they succumb to the visual clunkiness we used to deride as “un-Mac-like” back in the day…

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