Due Dates, not "Want to Do" Dates

January 14, 2024 by Stephen Dolan

Ben recently tagged me in a post on X asking about Due Dates:

This is the first reactionary step most people who have semi-working systems take when they begin to fall off the wagon.

And the worst part is - it kind of works. You probably won’t miss too many commitments, and you’ll complete tasks each day that felt urgent at some point.

This middle ground unfortunately isn’t painful enough (to yourself or others you work with) to push you to get back on the wagon. I’ve coached people who have been in this failure mode for weeks, months, or even years.

The easy answer

Stop using Due Dates for things that aren’t really due on that date!

It’s just that easy, right?

Unfortunately, this is really just reframing the problem as a desired outcome. To achieve that outcome, I’ve found two things to be most impactful for clients I’ve worked with.

Have a usable list of your options to work on

Many people revert to abusing Due Dates because it naturally creates a smaller subset of the tasks they’ve captured that they can actually maintain. Most to-do lists use flashy colors, alert badges, etc. to make the number of things you need/want to do very obvious.

The problem is, this leaves everything else in your system completely out of view. Didn’t put a Due Date on that inbox item you captured and forgot to clarify a week ago? Whoops; missed it!

An absolutely critical part of any productivity system is having a single, trusted list you can go to when you want to answer the question “What do I work on next?”

For me, that’s my Next perspective in OmniFocus, which you can download here.

If you don’t have a list that shows you the options you have to work on, of course you’re going to make a fake one with due dates. Where else would you go?

If you do have a list like this but it has too many options, slim it down!

  • Snooze or delete Projects that you’re not realistically going to get to in the next 3 months.
  • Delegate tasks that you don’t personally have to do to progress the project.
  • Spend an hour running through the list, completing anything that will take less than 5 minutes (use a timer for this).
  • Renegotiate commitments that you might have optimistically made with others but can’t realistically keep.

This is the single most effective step you can take towards stopping the misuse of Due Dates. If you have a list with a reasonable-to-you number of items to pick from that you look at every day, you won’t need the safety blanket of attaching arbitrary Due Dates to tasks. Simply review your list, pick the next most important thing (or the thing with a real due date), and do it.

It’s also the most time-consuming way to resolve the issue, and unfortunately only takes more time and effort the longer your system has been in this state. If you want help digging out of a hole like this, I can help with 1-on-1 coaching!

Un-ugh-ify your tasks

This part of Ben’s post really stuck out to me:

when it’s an ugh-y task I push it out another day and avoid.

When our systems aren’t in a highly-maintained state (through regular Weekly Reviews), another side effect that’s easy to ignore is that we start committing to things that we don’t want to do or don’t really even think are worth doing (or, as Ben put it, are “ugh-y”).

Why are you working on this thing? What outcome (Project) are you trying to achieve?

If that outcome doesn’t matter to you or excite you:

  • Make it matter with more optimistic, inspiring naming. “Call Joel” (a single task) becomes “Maintain a meaningful relationship with my best friend” (a Project) with a Next Action to “Call Joel”.
  • Make it smaller with a more concrete, defined scope. “Join gym” could become “Open https://thegym.com/sign-up and create an account”. Make it matter by putting it in a Project called “Improve the odds that I can watch my niece get married” (or something smaller, if that’s too lofty to actually motivate you).
  • Make it go away by having difficult, direct conversations. Don’t think that delivering this report to your boss actually matters at all? Tell them (kindly, with empathy) and let them know that it’ll help you produce better output if you can agree on the value it brings. You might end up agreeing to do something else that does matter, and this thing you didn’t want to do can go away.

Want five of the most powerful lessons I teach to my clients sent straight to your inbox?