There’s a category of task that lives permanently in the grey zone of my to-do list. It’s important. Sometimes it’s even exciting. And yet… I never do it, or rather, never do enough to finish it within a reasonable time. I just keep nudging the due date forward a few days at a time, like I’m playing a game of digital hopscotch.
You probably know the one I mean. It’s the proposal for a new project you believe in, the half-written blog post you meant to publish last month, the big but non-urgent refresh of your presentation slides, the long overdue documentation update, the portfolio redesign. There’s no external deadline as such, no boss breathing down your neck about it, no late fee, no disappointed client (for now, anyway). Just a vague sense of guilt and missed potential.
In this post, I want to explore why these “never-now” tasks are so hard to tackle—and what, if anything, we can do about them.
The Soft Deadline Problem
Let’s start with the obvious: soft deadlines. Yes, I’ve suggested that you use them as part of your overall arsenal but I think you already know they are not the best long-term solution. And yet you keep setting them. We convince ourselves that if we just pick a date—any date—we’ll be more likely to take action.
Sometimes that works. But often it doesn’t, and here’s why: deep down, we know the deadline isn’t real. And so, in the hierarchy of urgency, it always loses out to everything else.
A client email? Real.
A meeting invite? Real.
That thing you told your manager you'd get done by Thursday? Real.
Your own personal “I'll work on this by Friday” task? Fictional.
The moment your day fills up (which it always does), the soft deadline gets pushed back. And if you’re anything like me, you start playing a kind of psychological shell game, where you tell yourself you’ll definitely do it ‘next week’ or ‘when things quieten down,’ even though you know perfectly well those mythical empty weeks rarely arrive.
Why Are These Tasks So Slippery?
There are a few reasons:
No external accountability – Without someone waiting on the result, you’re the only one who notices the delay. And you’re surprisingly forgiving of yourself when busy.
Lack of clarity – These tasks are often big, fuzzy, and not clearly scoped. “Write a white paper” is much harder to start than “Draft outline for white paper (30 mins).”
They require ‘deep work’ – Because they matter to you, you want to give them your best. And that means you want an uninterrupted block of time. Which (spoiler alert) never magically appears on its own.
We overestimate the future – We imagine Future Us will have more time, more discipline, more inspiration. Future Us is a productivity god. But Present Us keeps leaving the mess behind.
So what can we actually Do? Over the years, I’ve tried lots of different tactics—some helpful, some gimmicky. Here are the ones that have stuck.
Make It Real (Even If It’s Fake)
I once scheduled a Teams call with a colleague where the only agenda item was: “Talk through Will’s blog post idea so he feels like someone expects him to write it.” OK, maybe not quite in so many words, but…that post got written within the week.
External accountability doesn’t have to be high-stakes. Sometimes just telling someone you plan to do something makes it feel more real.
If you work solo, try writing a status update for an imaginary stakeholder. Or send a quick message to a friend: “I’m aiming to finish that article draft by Thursday. Ask me about it?”
Use the ‘Start Even If’ Rule
One trick I’ve learned: commit to starting the task even if I can’t finish it perfectly or completely. The rule goes like this:
“I’ll start this task tomorrow at 10am even if I only have 20 minutes, even if I haven’t had my coffee, even if I haven’t figured out the whole structure yet, and even if there’s a client meeting at 10:30am.”
It’s a way of lowering the activation energy. Once I’m in, I usually keep going. But even 20 focused minutes is better than endless delay.
Separate Deadlines From Scheduling
If a task doesn’t have a hard deadline, perhaps don’t pretend it does. Instead, treat it as something you schedule deliberately, like a meeting with yourself.
For example, have a recurring “Focus Hour” every Wednesday afternoon, and drop in one of these slippery tasks into it. You’re not telling yourself it’s ‘due’ on Wednesday. You’re telling yourself, “This is when I’m going to work on it.”
This small shift helps you stop playing the artificial deadline game. Instead, you’re building a routine space for the kind of work you otherwise might usually neglect.
Break the Task’s Identity
Often, these tasks loom large because we think of them as projects, not tasks.
“Write book proposal” is a monster. “Write 100 words on the intro section” is not.
If I notice I’ve been avoiding something for weeks, I try to rename it to something less intimidating. Instead of “Update onboarding docs,” I’ll say: “List five things that are currently missing from the onboarding docs.”
That gets me moving.
Bundle With Low-Energy Time
This one might seem counterintuitive. We often reserve our low-energy time for admin or other less intensive work. But sometimes I’ve had more luck tackling these no-deadline tasks precisely when I’m too tired to care.
Why? Because my perfectionism is quieter then. I’m more willing to get something down instead of obsessing about doing it perfectly.
Try this: next time you hit a post-lunch slump, open the thing you’ve been putting off and just... fiddle with it. No pressure. Just fiddle.
Allow for ‘No Deadline’ Tasks—But Label Them Honestly
Stop giving fake due dates to certain tasks. Instead, just label them with a tag like ‘Someday’ or ‘Important but Floating’. Perhaps even move them into a separate part of your task list, where they’re reviewed weekly but not scheduled.
This way, you’re not constantly rescheduling them and feeling guilty. You’ve acknowledged that they’re important—but not urgent—and you can make a conscious decision about when to engage with them.
And when you do want to move them into your active work, just put them into the calendar, not onto a fictional deadline.
Let’s Be Honest: Some Things Just Don’t Happen
There’s a final point I want to make, and it’s a little uncomfortable.
Some of these tasks stick around because they feel important, but they’re not really. Or at least—they’re not important enough.
And that’s okay.
We don’t have to do everything. Sometimes, letting go of a no-deadline task is the most freeing thing we can do. Archive it. Cross it out. Say, “Maybe later,” and move on.
It’s not failure. It’s clarity.
In Summary
Dealing with important tasks that don’t have deadlines is one of the hardest challenges, especially so in hybrid and remote work. There’s no boss watching, no commute framing the day, sometimes even no clean boundaries between urgent and important.
But there are strategies:
Don’t lie to yourself with fake deadlines.
Schedule the work, not just the due date.
Break it down until it feels like something you can do now.
Involve others to make it feel real.
Know when to let go.
Above all, be kind to yourself. Some of the best things I’ve ever done started as messy, long-avoided, guilt-drenched “someday” tasks. And some of the best things I never did? They were just never meant to happen—and that’s okay too.