Deadlines Are (Usually) Dumb

I haven't set a real deadline in years.

And you know what?

The work still gets done.

Actually, I think it gets done better.

Here's the thing about deadlines: they're mostly fiction.

They're artificial pressure points we create because we think we need them.

But what they really do is teach us to ignore reality.

The Problem with Deadlines

When you set a deadline, you're essentially saying "This thing must be done by this date."

But why?

Based on what?

Usually, it's just a guess.

And guesses shouldn't be promises.

What happens when something more important comes up? What if you discover a critical flaw two days before your deadline?

What if a key insight emerges that could make the project 10x better, but it would take an extra week?

With a deadline, you're forced to make a horrible choice:

• Miss the deadline (and feel like a failure)

• Ignore the new important thing (and actually fail)

• Rush and do poor work (and create future failures)

None of these are good options. And they all stem from the same flawed premise: that we can predict the future.

Don’t even get me started on project management tools like Clickup having a “Due Date’ as a field.

Everyone fills it out, no one pays attention to it.

Completely worthless.

Priority > Deadline

Instead of deadlines, I work with priorities. It's a simple system:

1. What's most important right now?

2. Work on that

3. Repeat

That's it. No arbitrary dates. No artificial pressure. Just honest work on what matters most.

Sure, there are exceptions.

If you're speaking at a conference, the event has a real date.

If you're launching before a holiday shopping season, there's a natural timeframe.

But these are rare cases where external reality creates the deadline, not your imagination.

The Freedom of No Deadlines

When you drop arbitrary deadlines, something interesting happens. You start paying attention to what actually matters. You become more responsive to reality. You do better work.

Instead of asking "Will this be done by Friday?" you ask "Is this the most important thing I could be working on right now?"

That's a much better question.

You also stop doing this weird thing where you pretend time estimates are accurate.

We all know they're not. A task you think will take 2 days might take 2 hours or 2 weeks.

By focusing on priorities instead of deadlines, you can adapt to reality instead of fighting it.

But What About Accountability?

People often say "But without deadlines, how do you make sure things get done?"

Simple: you trust in priorities and progress. If something is truly important, it will stay at the top of your priority list until it's done. If it keeps getting bumped by more important things... well, then maybe it wasn't that important after all.

Progress is visible.

Work is visible.

You don't need artificial deadlines to see if things are moving forward.

Real Life Isn't a Series of Deadlines

Look at your own life.

Do you set deadlines for making dinner?

For having good conversations?

For learning new things?

No.

You just do these things when they need to be done, based on their importance and the natural rhythm of life.

Work can be the same way.

Try it.

Drop the deadlines. Focus on priorities. Watch how your work improves when you stop pretending you can predict the future.

Yallah Habibi,

Jon