I'm a list maker by nature - my wife sniggers at me sometimes as I add something to my to-do list that I've already done, only to mark it completed immediately (I like having a record of those things).

For years, my to-do list flow was something like this:
  • Remember just before bed that there are a couple important things I need to do the next day.
  • Grab a piece of paper (blank paper, a bill, whatever's laying around).
  • Make a quick to-do list in the corner, rip it off the full paper and put it with my wallet.
  • Come home from work the next day and find the piece of paper with my wallet with most of the tasks undone.
When I got an iPhone a couple of years ago, I decided I was going to start using a better system.

For the past couple of years, I have used Remember the Milk, a fantastic to-do list manager that has a great iPhone application.  It has some benefits and drawbacks though:

Remember the Milk Benefits:
  • Easy to use
  • Keyboard commands
  • Great iPhone app
  • Reminders
  • Repeating Tasks
  • Tasks can be set for a specific time as well as date
Remember the Milk Drawbacks:
  • iPhone app requires a $25/year Pro membership
  • Email reminders are only for that day's tasks, not for anything that's overdue
  • Can't reorder tasks other than using priority or the like
When the time came for renewal of my $25 Pro membership this year, I decided to look around.  My only major requirement was that whatever I did needed to have a native app on the iPhone so it could remind me about tasks.

I discovered Wunderlist fairly quickly, due to the amount of buzz around it and gave it a try.  I really really wanted to like it.  I went all in, migrating by hand my entire existing list of short term and long term tasks.  I gave it a full month before I finally threw my hands up and had to go back to Remember the Milk.

Wunderlist Benefits over Remember the Milk:
  • Reorder tasks to your heart's content
  • Native Mac App
  • FREE
Wunderlist Drawbacks:
  • Reminders only worked when adding tasks from the iPhone app (if you set them at all).
    • Any tasks added from the web interface don't get a reminder email.
  • Can't set a time on a reminder (Call John at 1pm tomorrow)
  • No repeating tasks
These drawbacks all ended up becoming an overall deal breaker for me.  I need my to-do list to remind me every month when various bills are due, every 6 months to renew my auto insurance, etc.  I need to be able to be reminded at a specific time about something.  Finally, I needed to be reminded when I had something due, regardless of where I entered the task.

I hope Wunderlist can add these features someday and if so, I'll give them another shot.  For now though, I am happily back at Remember the Milk as a Pro member again.  It's just not that important for me to be able to reorder tasks and save $25/year.

Now if Remember the Milk could just let me reorder tasks and add subtasks into the mix, I'll be a member for life!