Ask HN: Programs that wasted you 100 hours?

121 points by lioeters ↗ HN
In the spirit of "Programs that saved you 100 hours?" ¹, - I'm curious to hear of experiences with software systems, languages, apps, or services that led you down an unproductive rabbit hole, only to come out at the other end (if ever) with not much to show for the effort.

¹ https://news.ycombinator.com/item?id=22849208

260 comments

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Microsoft Powerpoint (and to a lesser extent Word). I lost count of the number of days I spent trying to make my presentations and documents look good (which for me means pixel perfect).

To be clear, this isn’t a failing of the software per se. PowerPoint is powerful and lets you do a lot of stuff, but I took desktop publishing lessons in high school, and I’m a bit obsessive to start with. I just have to have everything lined up and evenly spaced and just so. Which PowerPoint lets you do easily enough, but then you need to add another box to your diagram... and resize and reposition everything more or less manually.

Similar story for Word, which almost lets you do professional(ish) documents once you know where all the typesetting options are hidden. I’ve given up on Word for technical documents and now use Markdown + pandoc to convert to Latex and then pdf.

TBH doing it all in LaTeX you end up down the same rabbit hole, looking for the One True Way to do this and that, at least for me. I do enjoy it a lot as it teaches me about typesetting internals, but it's not faster with one or the other technology.
Because the bottleneck is not the tool, but rather your decision making process.
You do presentations for your audience. Adjust the contents, adjust the style.

If your audience doesn't need pixel perfect, don't do it. In my experience, the speed of adapting a PP presentation is more important than it's "beauty" by some abstract definition.

Aesthetics help to be taken seriously. But are you delivering the content or the design?

Same experience here. On PowerPoint, when there is repetitive work (weey presentation etc) i try to get a correct template, but most of the time I spend too much time on it, it's just a pain, and the corporate templates are horrible.

Everytime I can go away with a very simple presentation I do it, but for some reason we are partly judged on powerpoint appearance. I once did an animated background for a presentation as a joke, and was praised by everyone for it instead of my team being blamed for doing useless things on work time.

And I don't really see an alternative. It's more of a cultural issue.

I have a hard time using word, and corporate templates used to be good and complete but aren't anymore. Fortunately we usually have competent secretaries who do the formatting and some editing work.

For less official work I use markdown or latex most of the time.

At my current company, Powerpoint is used as the main medium for communication and reporting. Powerpoint slide decks are even considered some form of documentation by many, even though they are not really suited for that: Bullet points instead of coherent prose and explanations, ambiguity on the audience of the presentation (internal vs customer), general clunkiness of a ppt files. For many projects, documentation is just a shared directory with a number of powerpoint files from various stages of the project. I hate it and I want to change it, but I am still new to the organization and this behavior is deeply ingrained.

Besides that, Powerpoint is pretty good if you actually want to do a presentation.

So do you have any go to tips or shortcut (keys) that are your favorite?
On the flip side, I've noticed PowerPoint can bring immense efficiency gains to environments where the standard is to write to a detailed report for every little thing. You don't need a detailed user guide of 20 pages of text if a few ppt do the same job.
Every program in the Microsoft Office suite.
Even OneNote? Outlook/Exchange?
Compared to what?
Exactly. I'd love something that works better but gave up on Libre/Open officer after sending people's dozens of docs that opened looking a complete mess.
Exactly. I love the spirit and motivation behind Office Libre, but Excel and Word just _work_ for most basic tasks and an amazing number of corner cases. Open-source products just don't even come close.

The only tools people don't complain about are the ones that no one uses.

At least Libre Writer has sane ways to anchor a picture to a paragraph / section / page.

I've lost my 100 hours trying to get Word to consistently place images in technical docs, only to wind up fighting some of the most unpredictable placement calculations I've ever encountered. I want to punch my screen right now just thinking about it.

I just gave up years ago and put all pictures inline.
The sad thing is that LaTeX can be quite temperamental with image placement too.
I think one of the big problem of Word is that it is routinely used for things it was not designed for and which are still out of Microsoft target.

It's a tool for not too long technical documents, for secretarial work, for basic marketing text, for quick an dirty but decently presented invoices, for writing a resume.

It has never been meant for writing novels, for page setting, for writing hundreds of pages of technical documentation, and yet... it is used for that. Everyday.

Simply because it's available everywhere.

But mainly because there are no viable alternatives that are available in multiple platforms, cost less or the same than Word, and do things significantly better.

InDesign is infinitely better for typesetting, but you're the learning curve to get something presentable is higher than LaTeX, because you have to know design, and more expensive than Word.

LyX is the only tool that comes close to replacing Word. It's free, significantly better typesetting, easy to use, and available in most platforms.

Not using them. Its amazing what you can accomplish with a plain text editor and your brain. Ever seen a presentation that didn’t rely on PowerPoint? It’s such a refreshing thing to witness. How many Excel “applications” have you used that actually worked as intended consistently and weren’t just a giant time suck that would be better spent building a simple form over data app?

Ask yourself this: When was the last time you truly needed MS Office to produce something of value? Not imaginary enterprise “I look busy so I must be getting things done” value... but true value.

Tell me how you format your PhD thesis in a plain text editor without wasting countless hours on LaTEX?

Sure, designers create beautiful presentations outside PowerPoint, but I can grab master slides, plomp down the stuff that I wrote in a plain text file and bam - presentation ready in 10 minutes.

Excel - I'm a programmer but even I use Excel for quick data tasks - cleanup, remove duplicates, create histogram and summary, build a pipeline for data where I see intermediate values for every step for every data point. I might be an exception but I sometimes even copy data from an SQL client to Excel to drill into it.

Or Access? Entire departments of non-technical people are running on this stuff.

If Office didn't provide anything of value nobody would use it.

Perceived value isn't the same as actual value, especially in the enterprise and academia.
> Tell me how you format your PhD thesis in a plain text editor without wasting countless hours on LaTEX?

I've never written a thesis (at all, let alone for a PhD), but my impression from people who have is that the academic institution typically already has a LaTeX .sty or template or whatever, so literally all you're doing is writing content (and the minimal amount of markup necessary for document structure).

That said, I can see how this might quickly go sideways as soon as you start using TikZ, or if you do indeed have to create your own style (though in the latter case the defaults seem reasonable, and indeed seem common if the numerous academic papers I've read over the years are any indication). I've written my fair share of technical documentation with LaTeX and it can definitely be a rabbit hole, albeit usually a self-inflicted one.

And that's definitely true about Excel and Access. Virtually every company has at least one Excel spreadsheet or Access database that's effectively mission-critical, lol.

Google Sheets and Apple Pages/Keynote, for me. They work so much better. I don't have any facts or list of features to back this up, they are just less stressful to use and don't bother me about licenses or corrupt files.
Microsoft Windows. I lose 10-20 minutes 1-5x a day just logging in to Windows in the NHS...
I second that. I loose 5 to 10 minutes every time I want to change a network setting. No idea how it got messed up so bad. What used to be two mouse clicks away from the desktop in XP is now hidden away by the "settings" app that doesn't contain any settings at all.
Funny thing is, the real settings app in windows is still more or less the same as xp and still just two clicks away. I think they just put the new fake settings app in there to fool people.
You can still open Control Panel in Win10 and get the prior behavior, almost. I just Start menu search for it and done.
I hope the other side of this pandemic NHS finally get their computer system replaced and not reliant on a single proprietary OS or DB.

I imagine if one were to add up all the estimated time wasted using that system and compare it to writing a client agnostic one from scratch it would probably turn out to be a massive saving.

I hope they don't try and do another massive centralised system. It failed before and will fail again.
And then when you just want to shut down your laptop so you can put it away but Windows insists on spending 20 hours installing updates first...
I remember one site where I would arrive in the morning and login. Then go downstairs, cross the street to Starbucks, queue up, buy a cup of coffee and if I was lucky the login would have finished by the time I got back.
I think it's commonly accepted that it's the NHS IT infrastructure that's b0rked, and not Windows per se.
WYSIWYG editors...

worst: confluence, bottom: desktop office suites, still bad: google docs

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Oh my goodness: #### that WYSIWYG editor in Confluence hard. It's like an extremely buggy version of Word 95. I've outright banned its use in our company.
And I can't count the hours I spent converting from org-mode or markdown to WYSIWYG, only to be stripped of my beloved editing tool at the point I need to share a doc.
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Perhaps a loose interpretation of “wasted”, but multiple different games have wasted a lot of time I would otherwise have spent doing more productive things. E.g. currently I have a side project that is actually really interesting to me but I have been spending my limited free time (with a toddler and an infant to keep up with) playing Deus Ex Mankind Divided. I may not end up spending an actual 100 hours in it, but I did a few years back with its predecessor Human Revolution.
Try to give yourself some slack. I too enjoy those games and have a toddler and an interesting side project. What works for me is to let myself unwind with some game time. And similarly reframe any time put into the side project as a win, even just a few minutes.

While I do get a rush from being productive it can be exhausting to always be 'on'. Games are one way to turn 'off', bring some variety to life, and experiment without guilt. Just remember that you don't have to finish the game or win every match.

Leisure and fun are often unproductive, some people include "unproductive" as part of their definitions.
LaTeX. Compiler errors, add-ons from the 80s, and unhelpful defaults. No problem to write Chinese chara… oh, in this environment? Sorry.

C++ compiler (or even better: linker) errors. They are just not meant to be read by humans, lacking any pointers on what's really the issue.

Also the Makefile. I still cannot write customized Makefile for my side project now
I apologize for saying this in advance but I'd have to say for me it's GIMP.

Even after all its feature and popularity I find it extremely hard to use and often end up wasting hours trying to create a simple graphic. As a last resort I always end up booting Windows just to use Photoshop to do the same. I have been trying to move away from Windows to linux and so far I'm super happy with everything. But Photoshop is the only reason I have to keep Windows alive (or atleast use wine)

IMHO, Gimp was much easier to use before they revamped the GUI to imitate Photoshop. For those who didn’t try it, it looked like this: https://commons.m.wikimedia.org/wiki/File:Cleaning_up_Fourie...
The menu layout and structure looks exactly the same, except it's floating, which you get in modern GIMP by default. Can you explain in more depth how it's tangibly different?
The icons are different which still throw me off. The colour select tool is weirdly now stacked behind the cropping tool or some other selection tool.
That's why you learn keyboard shortcuts.
Shit, that's exactly what photoshop used to look like (photoshop 7)
It might've been for you. No discernible difference for me.
Um... I think they need a copy of Photoshop if they're going to try to "imitate" it. They imitated it as closely as chopping onions is similar to learning how to drive a car. I checked it out in January, while doing a month of open source alternatives to Adobe. That's a big no.

Adobe is pricey but that money is pumped very well into UI. After playing with some of the open source alternatives... yea, $55 a month is now cheap to me since I now know what crappy UI and ass backwards workflows really look like.

There was recently a post on HN about a GIMP fork called glimpse which aims to improve UI/UX: https://github.com/glimpse-editor/Glimpse or project page at https://glimpse-editor.org/
It's great to see that, but I doubt they can do much about the big UI issues, which come from the way GIMP's internals work. The fact that you still can't select more than one layer, not even to move them around, is a 100% deal-breaker for me and everyone I've shown GIMP to.

Fortunately, Krita has gotten extremely good, even for photo work. If anyone has a shot at clawing back some Adobe market share, it's then.

It’s interesting you say that, because I find myself to be quite productive in GIMP.

I think the basic set of tools are pretty easy to use, and the one or two other windows you need open (like the tool-specific settings) are also pretty understandable. When I stumble upon something new I often find pretty good official docs on the topic.

I don't know man maybe you're right.. But just today I had to edit a small screenshot and draw an arrow from text to a button and after trying all sorts of things like downloading scm scripts from defunct sites to reading two9 tutorials I couldn't do it. Maybe I lack knowledge to understand it. I kinda wasted more than 20 minutes and still don't know how to make arrow. Would take me 10s to do it in PS (plus boot time of Windows).

Regardless I do appreciate the hard work the guys have put in. I feel like such an ingrate to make comments like this about free software. I guess it's time to find an online course and learn it properly and if I still don't get it then that's that.

I'll echo this. Every time I use GIMP, I have to google and re-google what I want to do, skip through a Youtube video for the pertinent parts, discover that the youtube video is for an outdated version, google again, yaddy yadda yadda. Even for something as simple as putting red text over an image, or cropping down a picture, it just takes forever to figure out the magic incantations to get google to return something like what I am looking to do. Yes, I am sure that it is great for complicated image manipulation once I have been using it for a few months. I've even sat down to learn it before, spending a few evenings for a few months trying to grok it. But 95% of the time that I need image processing it's for incredibly simple stuff. Honestly, MSpaint is sufficient for ~90% of my needs and it takes 1/20th of the time just to load, let alone get anything done. GIMP makes great stuff faster than anything else. But I do not want to make great stuff, I just want to put an arrow pointing at a button on a screen capture.
Know what you mean, I rarely have to do image editing, if I can't do it in preview, I groan, because it usually means I have to go to GIMP and waste hours doing something that seems very simple. I think last time it was just adding a black border to an image, there seemed to be a border tool, but it insisted on making a picture frame effect and I could not understand why it just couldn't do a simple single colour border. And it seems slow, moving around the image, things like that, it should be far better.
Agree, I kinda hated the GIMP but then I learned it's logic and I started to like it. The problem is when you used Photoshop before. Some things that you can do there with one click take quite tedious procedure in GIMP. For instance drawing simple rectangle with fill facepalm.
Have you tried photopea.com? Not affiliated but I use it and switched off Photoshop to this and it works for most purposes.
For raster drawing there's Krita, for vector drawing there's InkScape, for raster manipulation there's GIMP. GIMP is really not for drawing and is cumbersome for those purposes. Just like you really wouldn't use InkScape for photo manipulation.
This is always surprising to hear, because for me GIMP is substantially more intuitive and productive and easy than Photoshop ever was. Maybe things have changed lately, but every time I've tried to use Photoshop my eyes glossed over, whereas whenever I fire up GIMP I'm pretty quickly able to figure out how to do something. This is especially true with "single window mode" enabled (which pulls those weird sidebar windows into the main window).

I definitely get that if you're already used to Photoshop then GIMP's gonna be an adjustment (and vice versa), and my GIMPing is admittedly not very complicated (mostly just making memes), but it's just weird to hear of people who think that Photoshop's actually easier to use given that I've experienced the exact opposite by pretty much every metric.

> because for me GIMP is substantially more intuitive and productive and easy than Photoshop ever was.

It took me some time to adjust, but yeah I felt the same.

> I definitely get that if you're already used to Photoshop then GIMP's gonna be an adjustment (and vice versa)

In fact the argument of people finding GIMP unintuitive is that Photoshop is better.

I mainly complain about GIMP's updates breaking changes though.

Only problem with GIMP is their idiotic decision to split saving and exporting.
A bit unintuitive, yes, but it makes sense. In PS, if I save as PSD, do some work, save as PNG, do some more work and save again, it'll be saving into the PNG, not PSD, which will effectively make me lose my work.

Their "Export and overwrite" menu makes it very convenient to do quick edits where you only care about the raster, and the split avoids the above mentioned stupidity when working on bigger projects.

Wow. So glad to hear I am not the only one who struggles with GIMP.

I find myself spending hours to do the most simple of tasks. Anytime I have to search for a tutorial on GIMP, I cringe. I am waiting for that UI/UX fork to come out for Mac.

What other alternatives are there that work on Mac besides Inkscape and Krita???

Program that saved me 100 hours: using LaTeX to write a scientific paper.

Program that wasted me 100 hours: using LaTeX to make the poster for said scientific paper.

LaTeX is great for when you need to focus on your content and don't have much time to spend on the presentation. However, once the presentation is the entire point, LaTeX is not the right tool.

Well, except if you like boring posters.

For me personally, my slides improved significantly when I started using Latex. Imo Latex forces you to give clean, concise presentations. If there is content that takes a lot of fiddling, your presentation is probably overloaded with things that won't reach the audience anyway.
You’ve never had to give a talk with a video inside ? Or have you gotten that to work in latex ?
Tab out to the video. Play. Tab back to presentation.

Video is included as a separate attachment in the email sent around.

Jira and confluence
I'd say Atlassian products in general. Jira has had a notorious bug for nearly a decade (still ongoing, I believe) that would delete a description/comment if you accidentally hit escape in the middle of writing it. Bitbucket also changed the term "blame" to "annotate" because "blame" was a strong word that hurts feelings (seriously, this is the reason) and didn't bother telling anyone until people started wondering why blame wasn't supported. Also there was the time they displayed a huge ascii rainbow logo every time you pushed a commit, which is pretty distracting, considering you're expecting to find info related to your push while you're working (you had to turn off this info altogether to stop seeing this logo). I could go on, but basically, Atlassian isn't terribly interested in your productivity.
Jira is slowwwwwwwww. Like using index cards on a whiteboard would be faster.

If you want to make sure no one ever reads a document, put it in Confluence. Unless you've bookmarked it, you'll never find it again, let alone anyone else.

All atlassian tools. I wonder how many layers of abstraction are involved in typing a comment...
SAS

Minecraft

Minecraft has potential to develop creativity though :D It's a hard one to quantify, but I think sometimes things like MineCraft, lego can boost cognition if used in a deliberate way and one actually takes some learnings from it.
MS Sharepoint takes the cake. Impossible to navigate, hysterically difficult to use for storing and maintaining content repositories / wiki's.

Also the outlook/skype/teams/lync universe of communication tools is laughably inconsistent, it's very difficult for me to do very simple tasks in these tools.

As someone about to (reluctantly) go down this rabbit hole, I'm not feeling reassured. ;(
I was playing around with Sharepoint Online, the latest version. It was my first time looking at sharepoint and I had something usable working in about 30 minutes. Maybe they fixed things with the cloud version?
I've disliked Sharepoint in the past, and recently also had good experiences. Yes, perhaps they have cleaned up their act.
I burned 4 years making SharePoint intranet sites inside a big corporation. None of those skills transferred to modern development.
I work with SharePoint professionally and it's incredibly frustrating. If I'm trying to find out which list a document was uploaded to, it could be in 3+ locations. Much of my time with SP has been spent figuring out where stuff is and WHY it was uploaded there in the first place.
Without a blink, McAfee.

This abomination has the ability to put more than decent computer into a miserable slug. I cannot imagine how much my client would have saved in productivity from all its employees and contractors if that thing was uninstalled.

On a similar note, Norton.
Instana. It helped me troubleshoot some really nasty bugs in production but it always takes me ages to find the information I'm looking for.
Excel.

Mostly because it makes you think you can do anything, and you can. It's a rope to hang yourself with.

While Excel is a great prototyping tool, it's really not great for production use. I've seen so many financial calculations attempted on Excel that ended up creating a huge ball of spaghetti, references going all over, VBA code mixed in with DLLs, VLOOKUPS all over, sometimes $A$1 sometimes A$1 (copying behaviour), huge Rube Goldberg contraptions.

And people love it, they often don't think about maintainability or ease of understanding for newcomers.

I'm with you. My org tries to do so many things with excel, despite that fact that is fails and breaks on us ever single day. What is worse, is that we use excel sheets and a shared folder to monitor projects, tasks, and even track casework. I hate it so much.
Yeah don't get me started on versioning, lol.

bondspricing_final_2_withswaptions_final_final5.xls. In a folder with 25 similarly named files. Good luck tracing the diffs.

But I guess that's not specifically Excel that causes this, it's people not understanding versioning.

But they all have timestamps, right? Newest is current, and then you have a time history of prior work....

(How it was explained to me once... that person swore they were worked to the bone to keep everything updated but they were SO inefficient and refused to listen to any constructive input because THIS IS HOW I HAVE TO DO IT.)

Blame the software industry for still not having a decent GUI for version control.

Version control has been "solved" for the better part of 20 years but the tools are awkward and only make sense if you're a software developer.

People unironically suggest you should learn more about tree structures to understand and work with git. That's just about acceptable for developers, but for non-developers that's a complete no-go.

One day there'll be a killer GUI for git or svn (or even just basic whole-file linear version histories) but until then, people are doomed to email files named like Presentation_FINAL_2_EJB_Edit.xlsx sitting under a "FINAL - DO NOT DELETE" folder.

I have gotten a pretty good workflow down on Excel sheets and version control thanks to gnumeric's ssconvert. Worth looking into IMHO.
Microsoft Access. I think the main problem is I keep expecting it to behave like a normal database. Perhaps if you go in without those expectations you'll have a better time? I don't know, and hopefully I'll never have to find out.

When I had to work with it on a semi-regular basis I kept this list of WTFs that I'd add to each time I finished tearing my hair out trying to fix some seemingly simple thing https://github.com/bourbonspecial/AccessFail/blob/master/why...

The Unity game engine. Backwards compatibility is low; documentation is scant or out-dated; error messages are misleading or opaque; stack traces for crashes are sometimes impossible to reason about.
Microsoft Outlook, no question:

- It hangs all the time for a few seconds at a time,

- The search is moronic (how about you look on the server and on my computer at the same time instead of hanging for a while and then displaying that dumbass message offering the option to search on my computer instead when there's a problem with the connection?),

- Switching to the unread message view regularly results in a progress doofer that never disappears until you switch to a different view and switch back

- The message list font size gets corrupted by moving between Windows of different DPIs forcing you to switch to a different folder then switch back again to make everything readable

- It asks you whether you want to save changes just because you've clicked a link in a calendar appointment

- Got thousands of emails? It's slow, slow, SLOW, SLOW(!!!), SLOOOOOOOOOOW!!!!!

- Too many modal dialogs

- It's clunky as hell when juggling calendar appointments, booking rooms, etc.

- When opening a meeting series it asks me whether I want to open the whole series or a single meeting every single time. Can I just have a modifier key for this, please, so that I can open whichever way I choose without being prompted?

- Inconsistent and unpredictable behaviour when it comes to inserting images as attachments versus inline in an email

- Losing messages in conversation view

- Difficult to follow conversations/find all messages if you don't use conversation view(!)

- Inconsistent behaviour around contact auto-completion: sometimes people end up in the auto-complete list, sometimes they don't

I could go on. I won't.

Ah, I see you have never had the pleasure of using Lotus Notes. These problems might seem insignificant in comparison.
Haha - yes, you're probably right. Company I contracted at a few years ago (and a big enterprise at that) still had a PC running a long unsupported version of Lotus Notes for obscure, but apparently business critical purposes, and it was becoming a huge problem for them. Fortunately not one that fell under the purview of the team I was on.
The one feature I love about Outlook is that the inbox can be sorted by Received time, ascending. And the list focus defaults to the most recent entry.

Every SMS and email client that has 'most recent on top' as the only view drives me f*g nuts.

I want my oldest conversations on top so I can see which ones have been awaiting a response or are done and can be archived/deleted, but apparently that's not how anybody works anymore.

That’s a really great way to get to emails I’m going to try it
I do that too. Hardcoded defaults is a pain. I acctually like desktop Outlook and I wish it just froze in time forever so I don't have to relearn it. I hate when the UIs are changed and I have to relearn where all the buttons are in a program I don't really care much for.
The new web-based Outlook 365 is a lot better, but still quite buggy and massively lacking compared to Fastmail.
I've used Outlook at a lot of companies and can't say I share most of these experiences.

10s of thousands of emails? Not slow.

Hangs for a few seconds? Not in my experience.

Whole series vs a single meeting? Only when editing, which makes sense. Opening to grab the conference ID? I don't get asked that question.

I've had to use Outlook in some way for the last 20 years, and I just live with it, but I'm also saying... what you describe hasn't been normal for me for a long time, at a lot of different companies. Maybe it's something to do with whoever runs your Exchange..?

> Maybe it's something to do with whoever runs your Exchange..?

Well it's 365 so that, unfortunately, is Microsoft.

I used to love Outlook until my work switched over to Office 365 version of Outlook. Now it is driving me nuts. The small things such as the animations when switching between mail and calendar, the way it displays conversations, the way it searches. I could go on, but I think we are on the same sinking boat here.
I think you're right: company I'm with has been using Office 365 since I joined back in 2017. In many ways it's decent but Outlook is just full of small irritations that really start to add up when you find yourself having to spend a lot of time in it.
The last good version of Outlook was 2010. Ever since they re-wrote the UI form 2013 onward, it's got more progressively worse.
MS Windows, any version except 3.1 or earlier. MS Outlook, MS Word, MS Excel, McAffe crap, KDE, Gnome, Pulseaudio, CMake (you don't need to configure anything). Android any version. MS would be proud to have the same amount of brain damage as in Android. Any Google software.
If you have any third-party Outlook add-ins enabled, you might try disabling them.

There are a lot of poorly written add-ins out there.

It hasn't changed much in the twenty years since I last used it then.
You should give the online version at https://outlook.com a try. I've been using it since the corona outbreak and it's actually better than the desktop version imo.
My company has recently switched to G Suite from Office, and I'm actually starting to consider this as an actual perk of working somewhere, just to avoid Office (Outlook above all, but also Sharepoint, etc…).
Wow! Had a CEO once try to convert the company from Gsuit to office/teams so he could use Outlook. Figured it was great...
Factorio?

More seriously, the absolute worst developer experience I've ever had was a weird proprietary environment called "OpenAT" for a mobile module system. Admittely we were in the beta programme because we needed features, but every new firmware update would fix some features of the operating system and break others. At one point while trying to debug terrible sound we noticed that the volume control wasn't at all linear but a sawtooth: the top few bits were getting lost somewhere. Development required Eclipse, and the reboot-download-reboot cycle took several minutes. No real JTAG, only debug logging over USB. Crashes would, however, lose the log buffer, so you couldn't be quite sure where the program crashed, and all the important bits were real-time so couldn't be single-stepped. Debugging all that was extremely slow.

A hundred hours is only just under three work weeks. It's very easy to get led into a dead end that wastes that much development effort on a feature that turns out to be infeasible or a bad idea, or an intractable bug. I think I've had one of those incidents at every job, not necessarily every year but frequent enough that they're not all memorable.

Factorio is great, I don’t see it as a waste! It’s given me a new respect for logistics and advanced planning. I think the whole idea is a massive exercise in programming, producing functions, changing structures and then debugging the problem/expanding the bottle neck. But yeah it’s still a game.
This is why I avoid the more complex games where you build things (Factorio, Kerbal space program, etc.) Playing them scratches some of the same itches I get from writing software. So I avoid playing them and re-direct that energy into using an actual programming language to build a real thing.

There are upsides and downsides. The challenges in a game are designed to be overcome, but the satisfaction of solving real problems is even better than solving puzzles in-game.

Sometimes the parallels for me are uncanny. I'm faffing about with OpenSSL right now and it feels like nothing so much as a badly designed game sub-system. Can somebody please fix OpenSSL so I can get back to the core game please? :)

I used to say that Unity3D is Minecraft for programmers.

True. Factorio shows how complicated and power wasting logistics are. And it's already generous enough by not having items that can expire, it makes logistics exponentially harder
Somewhere on the back of an envelope I have written "bipolar train-sistor", as the start of an attempt to do computation in Factorio without using any of the features intended for the purpose like the circuit network. Never got round to actually building it.

(An unloaded train is clearly a "hole" charge carrier..)

In a similar vein, DwarfFortress

I usually play it with DfHack to handle all the labour assignments automatically, and then I play it usually up to the point that I'm tapped into a magma shoot and flooding the magma with water to obtain obsidian.

Then I lose interest, and play the same biome on adventure mode where I attempt to find the ruin of the mine I created before and plunder it.

Yeah I've probably wasted 100 hours on Factorio.

The other 900 hours were great though!

:D

Factorio is such a great game! I have easily “wasted” more than 500 hours in that game. It’s one of the most satisfying games out there. The one thing that is incredible is that sometimes your layouts end up looking like circuit boards when zoomed out.
Datadog on Kubernetes, lately. Its blackbox nature creates tricky issues in my company's infrastructure.

OTOH, I used New Relic with PHP website 6..8 years ago, and it was awesome in everything, except the price.

I guess it all depends on the context.

In addition to the already mentioned MS Office pieces:

• Android programming. Tried it once, wasted many days trying to make sure the app works on all phone models ranging from $10 to $1000. There were some hardware-related parts that are poorly standardized and abused by the manufacturers a lot. And yeah, the $10-$1000 range coverage is a bit too much for such a poorly designed platform.

• Inkscape: if you are a perfectionist who regularly checks the SVG sources generated by Inkscape, then... you may develop insomnia. The bloody thing will stuff the file with garbage by some 90%, and will get all your coordinates un-rouned to some unreasonably distorted numbers. No, it's not the "floating point thing", it's worse. A few times I ened up writing up the SVG file by hand from scratch, while checking it in the browser. Inkscape is outrageously bad.

> Android programming.

Android Studio and Gradle can both die in a fire - how anyone manages to actually write a decent app with those two, is completely beyond me.

Wow! I'm honestly surprised. I find that environment to be great and nearly trouble free. Used it on Windows to build a native multiplayer game.
I always chuckle when I see a huge franchise app just crashing because I have worked with android and understand how frustrating it can be. It just tells me that I was not the only one struggling with the android development.
Tools without good open standards forcing me in to their UI or restricted file formats:

jira, microsoft exchange, horribly sceumorphic PDF, anything with DRM

Microsoft Defender. It gradually went from an invisible safety check to a massive tax on battery, I/O and productivity.

I disabled it recently after it got into an incomprehensible endless CPU loop. It's suddenly like having a new computer - it boots faster, I can switch tabs without grinding, just everything is faster.

I can't think how much time it must have cost me - on every interaction in years.

I've become wiser over the years, but the top 3 were

3: Windows/Symantec Defrag (pre-Vista era) When I had 10-40GB hdds it used to be mesmerising watching the blocks fly around the screen. Eventually I find something else to do and pretend the computer's broken.

2: Macromedia/Adobe Flash. Sometimes animations just didn't want to work. Tweens are notoriously random with complex drawings. Delete and start all over again.

1: Editing HTML after using a WYSIWYG editor. Code clean-up. It takes ages.

that brought back memories of early teen.
Defrag felt so good knowing things were getting put where they belonged.