(Start with Part 1 here, if you want)

Part 2:  Quest for Solutions

In Which Our Heroine Searches the World (Wide Web) and Shares What She Finds.

Good news: There are tons of options out there, so it should be easy to find something that works for almost any need.

My criteria again: I want something that is

• free or very low cost
• groups to-do items in categories
• assigns due dates/deadlines
• has priority levels, preferably visual
• lets me estimate how much time each task will take
• has easy integration into daily life, email/calendar
• can be worked on online or offline
• is syncable to ipod Touch
• is easy to use
• and did I mention free or nearly free?

Yep, I am one tough cupcake.  So here’s what I tried.

Task List from Google Labs

Because I’m a dedicated gmail and google calendar user, I was excited to try this brand-new feature, just launched in December 2008.

Setup and learning curve: assuming you already have gmail, 5 to 15 minutes.

Pros: Integration integration integration!

• I *love* having my to-dos be right in my gmail window, which is the web page I look at dozens of times a day.  I can choose whether to have the list be subtle, down the left-hand column along with the Chat and Label areas, or more in-my-face, popped up on the bottom right like a live chat.
• It’s very easy to click on an email and turn it into a “task,” which then shows up in the Task List by the subject line of the email, and also has a link back to the email itself, even if I’ve already archived the email.
• Basic task creation is nice, simple, easy and intuitive to use.

Cons: Key features missing.

• I so wish this could be integrated with google calendar and not just gmail.  You can set a due date (though it’s kind of hidden, so at first I thought you couldn’t), but there is no way to link the due date to your google calendar, which just seems silly.
• More suitable for a few items than for dozens; it’s just too unwieldy to put everything into one big long list.  You can make subcategories, sort of, by indenting; and you can set priorities, sort of, by moving items up and down the list.  But not really.
• The interface is kind of tiny and I kept having the task and the due-date calendar overlap so that I couldn’t actually make it work. Plus you can’t see your other tasks while you’re creating a due date for a new task, which I need to do in order to see when I have time for the new task. Very fidgety.

Bottom line: I’m keeping it installed, and I am using it as a kind of extra flagging system for emails that need action, or things I remember while I’m in my email. If you love gmail and you’re not trying to do much project management via your to-do list, it might work for you. But for my overall needs, it’s not sufficient.

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So then I surfed around and quickly found Brian Benziger’s 25 To Do Lists To Stay Productive, which is a fabulous starting place.  I agree with most of his notes but his list is from 2006, so a couple of the lists that he lists (say wha? yeah, I said the lists that he lists) are no longer extant, while others have been developed and now do much more. Many of these, like the popular Ta-Da, were great in and of themselves but still too simple for my confused, I mean complex, needs. (You might like ’em though, so do check out Brian’s list.)  Brian led me to…

Rough Underbelly

Setup and learning curve: 10 to 15 minutes; requires registration.

Pros: Very fun!  Makes work into a game.

• You assign 1 to 10 “points” to each task.  You can use either their system (“billable” work or getting new business gets you 10 points, whereas maintaining a professional relationship gets you 1 point) or you can make up your own mental list about how you assign value to your tasks.  When you finish a task, you “get” the points.  Then you get to see a cute little line graph showing you how awesomely productive you were today.  Fun!
• Also has a nice little timer, so if you keep it onscreen as you work through your tasks, you can see how long you are taking on each task.

Cons:

• Can’t categorize tasks (other than by the number of points assigned). I need categories, cuz I can’t wrap my brain around assigning relative importance to items in diverse areas of my life. Is “buy cat food” worth more or fewer points than “write pitch letter to Terry Gross”?  I’d hate to see my cat and my publicist battle that one out.
• Again, no due dates.

Bottom line: Excellent for what it is, a productivity booster for your one-person small business or single project. Not for multifunctional me.

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Rough Underbelly is based on, and led me to, the Printable CEO, where someone even more obsessive than me has created a bunch of download-and-print productivity forms. They are designed for you to keep next to you as you work.  I can’t really review them because I haven’t used it yet, but it’s intriguing enough to mention.  I will try out the Emergent Task Planner at some point, I think, which is billed as  “realistic” daily planner.  Yes, that IS what I need.  It takes a little time to click around the site and understand what the different tools are and how to use them, but he has a neat approach that basically involves turning your day into 15-minute chunks of time and then accomplishing things bit by bit, which makes total fabulous sense.

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Back at Brian’s top-25 list, I tried a few more things and then landed at:

Remember The Milk

Setup and learning curve: 10 to 30 minutes; requires registration; more to explore after that, if you want.

Pros: Lotsa functions, integration … task-list heaven.  I’ve already set it as my home page.

• At the free level, this site lets me input basically everything I was looking for: tasks, categories, due dates, visual priority levels (1,2,3), and how much time each task will take. Hoorah!
• I love that I can create several different lists. I can also create “tags” to group items across categories. For example, I’ve tagged items “phone” so that when I have a window of time to make phone calls, I can pull up “make hair appointment” and “call marketing person” even though those relate to different lists (Personal and Book).
• The “Location” feature lets you map your tasks geographically.  For me, I’ve started using it to identify things I’ll want to do in New York vs things I’ll want to do in DC. Then I can view all my New York items together, whether they involve personal friends or book tour business or something else.
• I love having lots of options for how I want to look at my tasks — just today’s tasks, for example, no matter what list I put them on.
• Calendaring:  A quick installation, and now my to-do items show up my google calendar, where tasks due on a particular day appear as a collapsible list at the top of the day with a little checkmark icon (sort of like the weather, if you’ve added a weather calendar).  I can edit the list, add tasks, and check them off as completed without leaving google calendar.
• Offline access: This is great for when I’ll be on an airplane trying to get work done, but without internet.
• Reminders: Option to get pinged in advance of tasks being due, via email, mobile, or your instant-message system.
• Upgrade to the $29 Pro level promises syncing with my iPod Touch (or iPhone).  Haven’t shelled out for this feature yet but if it works as well as everything else here, I’ll be delighted.

Cons:

• I have some quibbles with the user interface. For example, a checkmark in the empty box next to a task intuitively, to me, should mean the task is completed. Instead it means the task is “selected,” and I have to click on something else to actually mark it completed. Hmm. There are several things like this that are just slightly annoying.
• Several of the functions seem to only be accessible via keyboard shortcuts, with no menus. This makes the learning curve steeper than it needs to be, since it requires memorizing “m” for multiple-item selection mode, etc. Not quite as intuitive as it could be.

Bottom line: THE WINNER! Even though I’m a vegan, and not so crazy about looking at the little exploited cow icon every time I sign on (kidding… sort of…), Remember the Milk is the site for me. It’s so very functional that I’m willing to invest extra time in learning how to use it and overlook the slight awkwardness of the interface.  And I keep finding new uses for it.

And that is so much more than you ever wanted to know about to-do lists, isn’t it?

Next time, the million-dollar question:  Is all this actually making me  more productive????