The card on my screen says 21, but my gut feels like a 1. Actually, that’s a lie. My gut feels like I’ve been sitting in this ergonomic chair for 101 minutes too long, watching a digital progress bar that never moves while we debate the architectural weight of a button. Olaf S.-J. is on the other side of the laggy video feed, and I can see him doing that thing where he clicks a retractable pen repeatedly. He told me earlier he tested all 31 pens in his drawer this morning to find the one with the most satisfying ‘click.’ For a dyslexia intervention specialist, the tactile world is far more honest than the digital one. He deals in phonemes and the physical friction of graphite on paper; I deal in ‘complexity units’ that have as much substance as a ghost’s promise.
We are currently stuck in the middle of a sprint planning session. It is the 11th one I have attended this quarter, and the atmosphere is thick with the kind of performative logic that only exists in corporate software development.
Sarah is a pragmatist. She sees the code. I see the technical debt underneath the code, the 101 potential ways this migration could trigger a cascade of failures in our legacy API.
The Broken Shield
I find myself staring at the wall, wondering when we decided that human intuition needed to be translated into a modified Fibonacci sequence to be valid. The original intention of story pointing was supposed to be a shield. It was a way to prevent management from saying, ‘You said this would take exactly 3.1 days,’ and instead allowing us to say, ‘This is roughly this big.’
But like every good tool, we’ve sharpened it until it cut our own fingers off. Now, the point is the product. We are no longer building software; we are manufacturing velocity.
The Illusion of Quantification
Software development is closer to writing a novel than an assembly line. Yet, we argue over abstract numerical values.
Unpredictable (55%)
Discovery (35%)
Maintenance (10%)
The Need for Data-Driven Lies
I remember a time, maybe 11 years ago, when we didn’t do this. We just talked. We said, ‘This looks hard,’ or ‘I can get this done by Tuesday.’ There was a trust there that has been eroded by the need for ‘data-driven’ decision-making. Management wants a dashboard. They want a line that goes up and to the right. And because they can’t measure the quality of a refactor or the elegance of a solution, they measure points.
“This looks hard.”
“It’s a 21.”
This obsession with estimation reveals a deep-seated desire to treat complex, creative work like a predictable factory. We want the world to be neat. Sometimes a task that looks like a 1 ends up taking 51 hours because you discover a bug in a third-party library that hasn’t been updated since 2011. Other times, a 21-point behemoth is solved by a single line of configuration change.
When we spend two hours arguing about 11 versus 21, we aren’t actually talking about the work. We are performing a ritual to appease the gods of the Gantt chart. It’s a form of anxiety management.
The Need for Transparent Data
I think about the way we consume information elsewhere. When I’m looking for something practical, like a new appliance, I don’t want a ‘complexity score.’ I want the truth, not a story point. This is why I appreciate platforms like
Bomba.md because they provide clear, direct data-the kind of transparency that our planning sessions lack. There’s no philosophical debate about whether a washing machine is a ‘medium’ or a ‘large’ in an abstract sense; you see the capacity, you see the efficiency, and you make a choice. In software, we’ve buried that clarity under layers of ‘poker cards’ and ‘velocity averages.’
The realization: Story pointing is about translation, not estimation.
I made a mistake once, early in my career, where I tried to be too honest. I told a project manager that a task would take ‘as long as it takes.’ […] He needed a number. So I gave him 21. Why 21? Because it felt large enough to give me breathing room but small enough not to trigger a high-level meeting. It was a total lie. But it was a lie he could put in a spreadsheet, and that made it ‘true’ in the eyes of the organization.
– The Cost of Compliance
The Feedback Loop of Inefficiency
Olaf S.-J. finally stops clicking his pen. […] The Scrum Master records it with a satisfied nod. Our velocity is preserved. The dashboard is safe for another two weeks.
Inefficiency Ratio (Estimated Time vs. Work Time)
85% Estimation Overhead
We’ve spent 101 person-hours this week alone just talking about the work we’re going to do. If we had spent that time actually doing the work, we wouldn’t need to worry about the estimation. It’s a feedback loop of inefficiency.
[The point is not the point.]
Embracing the Unknown
Software is a series of unknowns. Every time you write a function, you are venturing into a space that didn’t exist before. […] Every time you fix a bug, you are solving a puzzle that someone else-possibly a past version of yourself-accidentally created. It is an act of discovery. And you cannot schedule discovery. You cannot put a 21-point value on a ‘Eureka’ moment.
We need to get back to a place where we value the outcome more than the prediction. We need to trust that when we hire talented people, they want to do a good job. They don’t need a Fibonacci sequence to motivate them. They need space, they need tools, and they need to be allowed to say, ‘I don’t know yet.’
Sailing the Wind
Olaf S.-J. is right about the pens. Sometimes, you just need to find the one that works and start writing. You don’t need to categorize the ink flow or estimate how many words you can get out of a single cartridge. You just write. And if the ink runs out, you get another pen.
As I close the Jira tab, I feel a strange sense of relief. The ritual is over. I have 11 days until I have to do it again. In those 11 days, I will actually build the thing. I will struggle, I will fail, and eventually, I will succeed. None of that will be reflected in the 21 points we assigned today. Those points will remain static, a tiny monument to a conversation that didn’t really happen, while the real work happens in the quiet moments between the clicks of a pen.
We pretend that the numbers give us control, but they really just give us a distraction. They give us something to talk about so we don’t have to face the terrifying reality that we are all just making it up as we go along. Maybe we should stop trying to measure the wind and just start sailing.
I check my watch. It’s 11:01. The meeting is finally over. […] He isn’t counting points. He’s just helping someone read. And that, I think, is a far better way to spend 61 minutes.