Imaginary deadlines | Amit @NextFive

My deadlines are just as arbitrary as this image. How real are yours?

I was stuck in traffic couple of Saturdays back with the expected arrival time at home showing up as around 9 PM on Google Maps. This was a problem.

I’d decided to post on HackerNews that day - a “Show HN” for a small tool I’d built. And I wanted to post between 6:30-7:30 PM. Why? Because my research said that was the optimal time for Show HN posts.

By the time I got home it was late. I hadn’t written the intro for the post. I was tired. And a bit bummed out because now I had to wait yet another week.

Then, halfway through dinner, I realized how stupid the entire thing was.

The deadline was totally made up. Nobody was waiting. No real consequences. It was just me creating arbitrary pressure on myself.

We treat our own deadlines like some real constraints when they’re not.

This creates two problems:

First, we feel like failures when we “miss” these imaginary deadlines.
Second - and this is the more insidious one - we use timelines as excuses not to start or continue to move forward (I only have 20 minutes; not enough time for the morning run; guess I’ll skip today)

The timeline becomes a blocker. We wait for that perfect zen-block of time when we can enter that flow state and get everything done in one shot.

Only there will always be something And meanwhile, we’re not moving at all.

If tasks aren’t getting done, the timeline isn’t the problem.

Of course, there’s the dopamine hit from checking things off. There’s that momentum of done tool. But if you are consistently failing to get that closure on tasks, either they’re not small enough. Or you have too many projects competing for attention. Or something else in life needs addressing.

The timeline is a symptom, not the cause.

Two ways I’ve found to handle this:

Either don’t get fixated on a deadline. Instead of a hard “I’ll launch by December”, ask “What’s the smallest next step I can take right now?” If you’re not taking it, why? Too big? Wrong project? Something blocking you emotionally?

That usually gets me moving. And if it does not happen in December? No harm done. January’s just as good.

Or be flexible on the scope. If you have a real deadline, be flexible on scope. Don’t ask “How long will this take?” and set an arbitrary deadline. Effort estimates are frequently wrong. Instead Ask “How much time do I want to spend?” - that’s your real deadline. And then stay flexible on what you can get done in that time. Fix your appetite.

A 10 mins jog in the 20 mins you have is still better than skipping entirely. Showing up dailyish matters.

Oh, and that Show HN post I was supposed to do? Well, I posted it last weekend, and guess what? Crickets. Zero engagement :D

But I got it done. And I’ll try again with the next version on any regular day. No drama.

Btw, here’s the tool I was sharing, just in case you were wondering.