Estimates aren’t bolted in concrete, they’re bogus and dysfunctional

The worst question someone could ask us is:

How long will it take you to do this?

Because predicting scheduling is not a skill most humans possess. There are some people with extraordinary executive functioning who don’t suffer from time blindness. Good for them.

For the vast majority of us, estimation is basically impossible.

Like my civil engineer friend likes to say, there are two kinds of estimates, those that are wrong, and those you don’t yet know are wrong.

Hell, even if we’ve done a certain task many times before, most of us have no idea how long a thing is going to take until we’ve done it. Somewhere in between twenty minutes and seventeen weeks.

I bet if I analyzed the last thirty tasks on my to do list, there would still be zero correlation between the time estimate and how long the work actually took.

The planning fallacy is too strong. Human beings are in denial about how time works. Our optimism bias creates the tendency to underestimate the time and cost required to complete things.

I remember back before the pandemic when working in offices every day was still a thing, people would always ask each other, so how’s your commute?

My answer would always be:

Well it depends. Without any train delays, maybe eighteen minutes. But if there’s some mechanical issue, inclement weather, a homeless guy taking a dump in the middle of the car, the local line is running express for a holiday, there’s track maintenance, or my regular station is closed and I have to walk eleven blocks in the snow to the next nearest stop, then getting to the office could take over an hour.

It’s fair to say I don’t know how long my commute is, or ever was, for any job I’ve had. Too many variables, too many unknowns.

Even working at home has no guarantees. Sometimes in the morning, my wife intercepts me en route to my desk for five minutes of cuddling. It feels wonderful, but technically, if you do the math, my seven second commute to the office has just increased by four thousand percent. So much for time estimation.

It seems the ability to determine how long something will take is some line of sorcery. I don’t know how people do it. It’s a mix between experience, guessing and magic, and then multiplying that estimate by pi.

The problem is, when someone asks you how long something is going to take, telling them that you have no idea is deeply unsatisfying. It leaves them nowhere to go. Nothing concrete to hang their hats on. You can always pull the zen card and say something esoteric like, it takes as long as it takes. But in my experience, most people don’t possess the equanimity to accept that interpretation of reality. They only grow more infuriated.

Holub, the computer engineer and agile expert, once gave a fabled speech about how estimation has no value at all. Here are a few passages from his presentation that I found insightful:

*Estimates are always based on guesswork, because what you’re implementing is something that hasn’t been implemented before. Bosses think estimates are bolted in concrete, but they’re bogus, dysfunctional and lead to irrational schedule which are destroying our lives in every way possible.

*As soon as you put estimates on the scene, you can’t have a sustainable pace anymore, because as soon as you have estimates you have deadlines, and as soon as you have deadlines, you have people working eighteen hour days in order to meet them.

*The solution is, do good work at a steady pace that you can sustain your indefinitely. Where you’re working at a rate at which the you never get exhausted, and you never come in the morning so tired that you can’t actually get work done.

Wow, just imagine if more organizations adopted this principle. Wouldn’t you love to see a section on the careers page of a corporate website that reads:

“Our company believe estimates always inaccurate and therefore pointless. Instead of wasting valuable time and money guessing how long everything is going to take, we merely begin the work.”

Man, that company’s weekly application volume would skyrocket. Every top candidate on the job hunt would kill to work there. Because they would see very clearly, now here’s a company that’s at least somewhat rational. How refreshing, considering we now live in a world where our favorite pastime is denying reality.

Covid taught us many lessons, not the least of which was that human beings have a powerful subconscious defense mechanism to deny. We will refuse to acknowledge unwanted or unpleasant facts, realities, thoughts, or feelings.

And we will avidly discount scientific consensus. As long as that helps us avoid psychologically uncomfortable truths.

Who needs reality when we’ve got conspiracy theories and shocking absurdities?

What’s fascinating to me is, there’s no one group, one side of the aisle, or one political party with a monopoly on this behavior. We all do it. Myself included.

Which means the healthiest thing we can is to stop being in denial of denial. That’s step one. Like the twelve steppers say, recovery begins with the admission that we have a problem, and it’s become unmanageable.

We look ourselves in the mirror and say, yep, I am full of shit, and I know it.

If more of us were honest about the fact that we’re just guessing, about everything, just making up these bullshit estimates, then maybe we’d actually get somewhere.

How long will it take you to do this?

I don’t know. It doesn’t matter. Let me just begin the work and let it teach me.

Tom Petty famously said the song about learning to fly. Here’s my favorite lyric.

I started out, for god knows where, but I guess I’ll know, when I get there.

Tell me that’s not the best project management mantra of all time. It’s a steady, sustainable pace that’s rooted in reality on reality’s terms.

We accept the fact that human being can’t control anything, that we’re poor predictors of almost everything, and then we crack on and do the best work we can.

Are you estimating your way into a stress related illness?