[HN Gopher] Painless Software Schedules (2000)
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       Painless Software Schedules (2000)
        
       Author : MonkeyClub
       Score  : 54 points
       Date   : 2026-01-26 11:08 UTC (4 days ago)
        
 (HTM) web link (www.joelonsoftware.com)
 (TXT) w3m dump (www.joelonsoftware.com)
        
       | SyneRyder wrote:
       | 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.
        
         | awesan wrote:
         | 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 wrote:
           | 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.
        
         | eweise wrote:
         | 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!
        
       | avadodin wrote:
       | 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 wrote:
         | The stackoverflow investors (Prosus) have licensed their data
         | to the AI companies for training. They are most likely doing
         | fine.
        
           | stuxnet79 wrote:
           | 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 wrote:
         | > What's the saying? Time in the market vs timing the market.
         | 
         | Seems like he managed both.
        
       | cratermoon wrote:
       | 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.
        
         | pan69 wrote:
         | Exactly the reason why such organisations tend to fail.
        
           | mandeepj wrote:
           | Are you saying companies where the schedule is set by
           | management tend to fail?
        
             | wtallis wrote:
             | 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?
        
         | xtracto wrote:
         | 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 wrote:
           | 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.
        
       | stevoski wrote:
       | 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.
        
         | j45 wrote:
         | Reading into Joel, he was building SaaS. Fogbugz to name one.
         | 
         | He seems to have other posts on the lifecycle of software and
         | product budding. Maybe it wasn't mainstream then but some folks
         | were doing meaningful parts of it.
        
           | stevoski wrote:
           | Fogbugz, if the first version even existed in 2000, was not a
           | SaaS. Nor was Jira, by the way.
           | 
           | Both products were initially once-off purchases that you had
           | to install and run on your own infrastructure, and with new,
           | major versions packed with new features that you had to buy
           | if you wanted, but could ignore if you didn't.
           | 
           | The move to a SaaS model came years later for both products.
        
       | allknowingfrog wrote:
       | "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.
        
         | eterm wrote:
         | 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.
        
       | petcat wrote:
       | > 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 wrote:
         | I mean if Netscape had been in any kind of condition to defend
         | itself maybe MS wouldn't have succeeded.
        
           | petcat wrote:
           | 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 wrote:
             | 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.
        
       | cs_sorcerer wrote:
       | 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 wrote:
         | 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.
        
       | jillesvangurp wrote:
       | Don Reinertsen did some nice work on what he calls lean 2.0. Part
       | of that is basically doing cost estimations for work. Cost
       | estimations basically just boil down to hours times cost per
       | hour. The nice thing of thinking in dollars instead of hours is
       | that it suddenly becomes a money game. Now there is a stake.
       | Because companies are usually budget constrained and while they
       | can pretend there are more than 24 hours in day, pretending there
       | are more dollars in the bank is a lot harder. The tradeoffs get a
       | lot more real.
       | 
       | One of the points he makes that a bad estimate is better than no
       | estimate. If you have no estimates, you literally can't plan.
       | Even if you are going to be off by 3x it's better than not
       | knowing. A lot of the companies have no clue about the cost of
       | what they are doing. So, he fixes that by making them predict
       | cost of their plans. Which in turn forces them to do time
       | estimates. Like Joel says, breaking things down helps making
       | better estimates.
       | 
       | Another point he makes is that different people can come up with
       | wildly different cost predictions for the same thing. That's
       | still a lot better than not having any cost at all. Whenever you
       | get wild divergence in cost estimates, that signals that there's
       | no collective understanding of what a team is doing. That's a
       | problem that needs fixing or somebody needs a reality check with
       | their expectations (e.g. managers). If they are low balling an
       | expensive thing, they are going to look pretty bad when that
       | doesn't happen repeatedly.
       | 
       | And then he introduces a concept called "cost of delay" which is
       | a simple potential revenue based mechanism for calculating what
       | it would cost if feature X ships 3 months late. Now you get money
       | based prioritization. We make more money if we do X before Y.
       | 
       | And a final point he makes is that empowering people to come up
       | with money saving measures can actually be hugely beneficial.
       | Some things get cheaper if you rethink a design, maybe re-
       | implement some thing, etc. Instead of making people beg for
       | permission to do that, it's much more cost effective to let
       | people figure things out. Up to a certain dollar amount. That
       | amount can go up or down as people gain experience. But the point
       | is that rewarding people for things that are profitable is a very
       | sane thing to do for companies. And usually the experts have the
       | best understanding of where the potential gains are.
       | 
       | All very simple ideas conceptually. But the thing is, many
       | software shops have no clue about any of this. They don't
       | understand their own cost. They don't understand the dollar
       | impact of choices they make; including important things like
       | prioritization.
       | 
       | I don't actually practice any of this. But it's an intriguing way
       | to look at estimations. Well worth checking out his work.
        
       | commandlinefan wrote:
       | 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.
        
       | neves wrote:
       | I really miss Joel writings. His wit was unmatchable
        
       | robshippr wrote:
       | 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.
        
       | arrsingh wrote:
       | 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.
        
       | robotresearcher wrote:
       | 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.
        
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