I thought deadlines were perfect to inject urgency and boost my productivity.

Guess what? I ended up putting deadlines on ALL of my tasks.

Big mistake.

I felt more stress looking at all the looming deadlines on my to-do list. I eventually postpone 90% of them. Deadlines became more of “When I WISHED I can finish it” instead of “When I MUST complete it.”

Don’t get me wrong…

Deadlines are still a powerful tool to use.

But because it is sooooo powerful, you must use it sparingly.

The less you use it, the more important it becomes and the more it gets respected.

This is key if you want deadlines to work for you.

Ideally, you should only see a 1–3 deadline-driven tasks on Things 3. It makes the UI feel so much cleaner, less stress inducing and best of all?

You get more agency in choosing the tasks.

Once you get to choose what to do, when to do, this sense of control will make your work day feel more in control.

Especially if you have side projects that you answer to no one, this concept is super effective.

Deadlines are best used only when you know something bad will happen if you miss it.

Examples are things like client deliverables, project launches, even simple things like “Buy X item before DATE to save 30%.”

External deadlines carry real consequences . Miss them and you face embarrassment, damaged reputation, or worse, lost income.

This creates a social pressure that forces you to commit to doing it.

Internal tasks are different. These are the things you add to your list.

There are no external parties mandating you to complete them by a certain date:

For these, deadlines become a trap.

Here’s what happens:

You set a deadline. You miss it. Then you forgive yourself (because who’s watching?) and push it to next week.

We’re WIRED to do this. Our ego protects itself. It’s easier to say “I’ll do it another day” than to face the uncomfortable truth.

And once you postpone a deadline once, it loses all its power. Then it gets easier to postpone it twice, thrice…until it maybe you chance upon a new productivity tool.

You’ve lost respect for your tasks.

Before I add a deadline to any task, I ask myself:

“Am I really answering to someone else, or just to myself?”

If it’s just me? No deadline.

Instead, I let three things guide when I do the task:

This approach comes from within. It’s more intentional, transparent and lets me face reality instead of setting up artificial deadlines and say “next time!”

When you don’t use deadlines for tasks, something interesting happens: you can’t hide anymore.

If you keep postponing that side project week after week, you can’t blame the deadline.

You can’t say “Never mind, I’ll just shift the deadline to next week.”

You have to face the real reason:

That ownership is being honest with yourself about time and priority.

I’d rather face that discomfort than keep lying to myself with fake deadlines.

There’s a grey area: tasks that feel internal but have external elements.

Like if you’re learning to drive because you need it for a job opportunity. Or building a portfolio because you’re job hunting.

For these, I still default to no deadlines and in doing so, I take a deeper look at the why behind the task.

When you can truly see its importance, the drive to do it becomes bigger.

Which brings me to this email itself.

Writing about productivity isn’t my usual thing. I run a newsletter about email copywriting.

But I wrote this because the principle of respecting deadlines (by using fewer of them) is exactly how I will try to be more consistent with this newsletter.