I liked this idea when it came out, and there was some software that implemented it. Mr Schedule by Andrew Pietschy added outliner functionality to Joel's idea, so you could see how much time a group of subtasks would take (and if you should maybe drop that feature group to make your deadline). It had some keyboard driven shortcuts that made it faster to move around in than Excel, while making things simpler.

Unfortunately Mr Schedule and the pietschy.com website disappeared. I made my own recreation using REALbasic / Xojo at the time, but never released it and faded from using it.

Joel Spolsky expanded the idea later with Evidence Based Scheduling:

https://www.joelonsoftware.com/2007/10/26/evidence-based-sch...

That takes the estimates from Painless Software Schedules, but runs a Monte Carlo simulation using your estimates & data on actual time taken, to create a confidence distribution curve graph of when you'll be finished.

I miss his writing, I haven't seen a post by him in a while. His blog and Coding Horror are what I used to read all the time in my undergrad.

I actually did this (around 2006) after reading this article by Joel and I was skeptical but I used excel and wrote down all the tasks that needed to be done and kept breaking it down till each task was in hours.

It took me a few hours to do and as Joel says in the article, it was not a fun thing to do (jumping right into code was more fun) but I stuck with it and did the whole thing.

Then I followed that list of tasks and kept track of when tasks started and ended and I was pleasantly surprised when after a few weeks the project was done right on schedule as predicted by the excel sheet. So my experience (data point of 1) was that it works if you do it exactly how he says to do it in the blog post.

I did it only that one time so take that for what it is.

The article mentions milestones twice, and assumes their existence. But the scheduling methodology described has nothing to say about where these come from or how to think about them. So it’s missing something that makes it at least a little less simple.

"When you have to pick fine grained tasks, you are forcing yourself to actually figure out what steps you are going to have to take."

That process isn't free. For many features, it's the largest share of the work.

As always, the only way anybody has ever thought of to "plan" software is:

    1) write down everything you're going to do
    2) write down how long that's going to take
    3) add them all up and voila!  You have a schedule!

The ways this breaks down in practice would be comical if not for the fact that everybody takes it so seriously. The biggest problem is that step 1 takes longer than the actual software development task all the time, every time. That might not be _so_ bad other than the fact that it's also always completely wrong.

> Netscape has seen its browser share go from about 80% to about 20% during this time, all the while it could do nothing to address competitive concerns, because their key software product was disassembled in 1000 pieces on the floor and was in no shape to drive anywhere. That single bad decision, more than anything else, was the nuclear bomb Netscape blew itself up with.

This post from spolsky is always amusing to me because it came 6 months after Microsoft was convicted of antitrust violations to crush Netscape. So it's funny that he claims Netscape killed themselves, when the courts actually said that Microsoft killed Netscape. Obviously Netscape made critical bad decisions, but Microsoft's illegal behavior was what actually killed them.

Was wondering how StockOverflow guy was doing these days and it turns out he sold the company for $2B in 2021. What's the saying? Time in the market vs timing the market. Good for him but imagine being one of the investors.

I really miss Joel writings. His wit was unmatchable

For many of us, the way we manage software projects has changed has changed so much since the days when Joel wrote this.

It was a different age, with different products. I’m sure there are still products built the old ways, but Joel was writing before SaaS and CI/CD and endless roadmaps.