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Posted by MonkeyClub 1/26/2026

Painless Software Schedules (2000)(www.joelonsoftware.com)
67 points | 36 comments
SyneRyder 1/26/2026|
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.

eweise 7 days ago||
Here's a real schedule: CEO: we need to launch x end of Q2 PM: Here are the four monthly milestones Engineer Mgr: Let's estimate the stories. Now put them into eight sprints Go!
awesan 7 days ago||
I have done the monte carlo thing in practice with a team and it works well under some conditions.

The most important is that the team needs to actually use the task board (or whatever data source you use to get your inputs) to track their work actively. It cannot be an afterthought that gets looked at every now and then, it actually needs to be something the team uses.

My current team kind of doesn't like task boards because people tend to work in small groups on projects where they can keep that stuff in their own heads. This requires some more communication but that happens naturally anyway. They are still productive, but this kind of forecasting doesn't work then.

rwmj 7 days ago||
I hate this whole thing with me having to use some tool to track the work (usually Jira which is a PoS). My entire output is data, why can't a tool automatically summarise what I'm doing? It seems an ideal task for an AI actually.
maccard 7 days ago||
Jira is fine.

Jira is excel for task management. OOTB setup works absolutely great, and then someone comes along who wants a custom field on tasks to support <something that they read about elsewhere> and now you have to fill in that custom field. they leave, and someone else comes in and adds a new one. 5 years later you have 11 new fields that partially overlap, some are needed for some views, some are needed for other, but you can't use default boards because person Y decided that they wanted to call Epics Feat's, and made a custom issue type.

And in the end, the people who actualy use those boards just export a filter to excel and work there...

People. The problem is people.

arrsingh 7 days ago||
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.

robshippr 7 days ago||
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.
allknowingfrog 7 days ago||
"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.

maccard 7 days ago||
It's also the most valuable part of the entire article, and is true whether you're using waterfall, scrum, Extreme Programming, Kanban, or whatever. It's also the only thing that reliably works - the better you are at breaking down your work the better your estimates will be. As you said though, breaking down the work is oftentimes the largest part of the work because it requires _starting_ the work in the first place.
eterm 7 days ago||
It's the opposite of free, it's valuable.

Even for features that stay on the cutting-room floor. Especially for features that stay on the cutting-room floor.

MoreQARespect 7 days ago||
I find that 80% of the time the assumptions i made doing detailed planning are invalidated when doing the actual work.

Usually whole subtasks need to be junked and others created.

petcat 7 days ago||
> 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.

bryanrasmussen 7 days ago|
I mean if Netscape had been in any kind of condition to defend itself maybe MS wouldn't have succeeded.
petcat 7 days ago||
Netscape made mistakes, but they didn't lose 60% of their market share in just two years because they didn't ship a major update. They lost it because Microsoft bundled a "good enough" browser with their operating system already installed on the computers out of the box.
bryanrasmussen 7 days ago||
Well first off I remember Netscape of that time, it was a disaster, and this was the time when most peoples computer browser stuff was handled by their nerdy relative. I had plenty of people I could have put Netscape on their computers but I didn't because it was just such a shitshow.

So I'm not sure about that loss of market share being just due to MS. IE at the time was just better than Netscape. You had to be a masochist to use Netscape. It would crash badly at the silliest little things, and since websites were made with even less professional standards than nowadays those silly little things were quite frequent.

You might have gotten IE preinstalled, but even for devs who went and installed Netscape it just made more sense to use IE, because it was better.

MS preinstalled IE, but Netscape made sure only the truly dedicated would actually download and use it.

Without Netscape's mess-up I can totally see them only losing 30% of their share, and being in a good place to recuperate when MS got slapped down in court.

commandlinefan 7 days ago||
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.
dmux 7 days ago|
How can breaking a task into sub-tasks that themselves are measured in hours take longer than the implementation of those features?
thinkzilla 6 days ago||
Making estimates is fine, but we should be clear that they are (provably) just opinions.

http://scribblethink.org/Work/kcsest.pdf

https://news.ycombinator.com/item?id=13731975

https://www.amazon.ca/Limits-Software-People-Projects-Perspe...

cratermoon 7 days ago||
4) Only the programmer who is going to write the code can schedule it.

This item makes Joel's scheduling idea a no-go at most companies. Schedules are set by management or sales and programmers are expected to meet the date or get PIP'd.

xtracto 7 days ago||
This was written at a time were Software Engineering (not Developers) was valued more.

I had my first programming job around this time, and there wasn't scrum and all that crap. I was a Jr engineer, still in the last semesters of univ. And yet, we were treated like you read in the post: We were handed a feature and asked to do it. First estimate it , then ask the Design guys for UI and finally start coding it.

Now Software dev feels like sweatshops, business people think we are sewing jeans. And Software Developers became code monkeys.

Its quite sad.

cratermoon 7 days ago||
I've been in the industry since before this article was written. Notice I said most companies. Back when programmers were valued more, we still didn't always get much say in schedules. Certainly more than we do now. Your term "sweatshop" is on the mark, too. Since the advent of "open plan" offices, we even look like rows of tailors sitting at sewing machines stitching together jeans.
pan69 7 days ago||
Exactly the reason why such organisations tend to fail.
mandeepj 7 days ago||
Are you saying companies where the schedule is set by management tend to fail?
wtallis 7 days ago||
The companies don't always fail, but the software projects frequently do. When was the last time you saw a headline about a massive software project and the outcome was that it was early and under budget with all planned features working?
avadodin 1/26/2026||
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.
akgoel 7 days ago||
The stackoverflow investors (Prosus) have licensed their data to the AI companies for training. They are most likely doing fine.
stuxnet79 7 days ago||
What additional data is worth paying for that wasn't already freely given awaY? Right now you can download the entire corpus of Stack Exchange content for local review off of the Kiwix library. Because it's primarily text the dataset isn't even that large.
simongray 7 days ago||
> What's the saying? Time in the market vs timing the market.

Seems like he managed both.

cs_sorcerer 7 days ago|
It is always interesting to me how Joel’s writing is so relevant despite how long ago it’s been written.

It has to be interpreted through modernity sometimes to account for changes but overall his stuff feels really solid

The_Fox 7 days ago|
Agreed- just a month ago I told my team to read https://www.joelonsoftware.com/2006/06/16/my-first-billg-rev... and note how Spolsky knew the details of his application (weird date issues in Excel and VB). If you want to be a senior engineer, you need to know where are the odd edge cases in your app. I don't want to be the only one on the team who remembers that stuff.
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