The Real Reason You Struggle with Estimating Work

“Can you give me a quick estimate on how long this will take?”

Cue internal panic.
A shrug.
A number pulled from the void.

Spoiler alert: You’re not bad at estimating.
You’re just being asked to predict the future… with incomplete information… under pressure… and sometimes with a meeting invite titled “quick chat.”

Estimation Isn’t Broken Because You’re Incompetent

It’s broken because:

Software is complex

Requirements are vague

Unknowns are everywhere

You’re being asked for numbers before understanding the problem

If you feel like you suck at estimating, you don’t. You’re just trying to do math in the middle of a magic trick.

The System Is Designed to Fail

Let’s be real:
Estimates often happen:

Before requirements are locked

Without input from the people doing the actual work

With pressure to “keep it under X hours/days/sprints”

In a culture where missing an estimate is treated like personal failure

It’s no wonder the estimates are wrong.
They were cursed from the start.

So How Do You Get Better?

You don’t need to be psychic.
You just need better patterns and better conversations:

Break down the work. Smaller is saner.
“Login system” is not an estimate—it’s a grab bag of nightmares.

Call out assumptions. Loudly.
“If we’re reusing the existing auth flow” is a very different estimate than “new integration with third-party OAuth.”

Estimate in ranges, not absolutes.
“2 to 3 days if nothing explodes” > “2 days.”

Pad for unknowns without shame.
Padding doesn’t mean you’re bad. It means you’ve been burned before.

Push back when asked too early.
“I can’t give a reliable estimate until I dig in” is a valid, professional response.

Your Job Isn’t to Be Perfect, It’s to Be Honest

Estimations go sideways when the culture demands precision without process.
You’re not a wizard. You’re a developer.
You can get better, but only if the system respects reality.

Estimating is hard because the system is rigged, not because you suck

Break it down, ask questions, and pad with confidence

Be honest about what you don’t know, early and often

It’s better to miss a padded estimate than lowball one and get burned