Project 8086 Part II: Real Mode Productivity; or, 8,086 Reasons to Get a Newer Computer

MS-DOS Correspondent Kevin Lipe reporting again from the trailing edge of computing. When I was last with you, we discussed the Pocket 8086. If you don’t remember what the Pocket 8086 is, or who I am, or what any of this has to do with everyone’s favorite Apple blog, I’d refer you to part one of that series, as it will sort of answer maybe two of those questions.

I was pretty ambivalent about whether the Pocket 8086 was good at what it was trying to do, because I didn’t really think there was much of a goal for the project other than “hey this is cool.” But as someone who always loves a good deep dive into old software tools to see what I can learn about how to work with new ones, I have to admit that I felt a strong urge to see if I could actually find some thing to use it for.

So that’s what we’re doing here: exploring the questions “what do I really do with computers?” and “what happens if I try to do those things on a Pocket 8086?”

The pain points with this machine were all with the hardware: the terrible keyboard, the lack of mouse emulation, the fact that Windows is on here even though the V30 processor only supports Real Mode applications–all of those things are still true, and they make any attempt to do any “real” work that much more painful on this device.

And yet: it is a computer, and a computer is a tool, so surely this one has its place too, right?

Let Me Tell You All About My Productivity System

…not really. Listen, I was a 43 Folders reader just like you were, and you really don’t want me to peel back the curtains on my GTD-flavored personal productivity vortex. (I’ll just drop the nugget here that all of my first-draft writing happens in Org mode and let you draw your own conclusions.) But what when I think about “productivity” I think about the things I use a computer for, and that’s a pretty simple list at the end of the day:

• I keep track of my work in the form of tasks and projects.
• I write in both text files and in word processing documents. (My day job involves a lot of PowerPoint, and I am going to continue not to acknowledge that here.)
• I model things and analyze problems in spreadsheets.
• I do a lot of email, and I do it in Outlook. (Unfortunately, I am one of Those People.)
• I also do quite a bit of outlining, project planning, and mind mapping.

I use a lot of very normal tools to do this stuff for the most part. Todoist is my list manager of choice at the moment. It could be something else by the the time Stephen publishes this article.

I use Emacs and I use Word, and I use Pandoc to turn Org files into Markdown, and even LaTeX every now and then.

Spreadsheets are always in Excel, because that’s the only real spreadsheet application, and I use it in R1C1 mode, the way that God intended.

The outlining and planning happens in Org mode, happens in Xmind, or sometimes even Microsoft Planner, which still isn’t as good as Trello, but is what I have access to. I don’t feel like these tools are really all that spectacular.

Sure, I also use Logseq, Syncthing running on a private file server, a lot of private git repositories, and all kinds of other nerdy stuff as infrastructure, but on the whole, that’s not really where work happens; rather, that stuff all functions to support the work.

Tools of the Trade

So, let’s say I want do to some of my “normal” stuff on my very “normal” PC/XT-class tiny laptop. What does that look like? How might that even work?

Master Control Program, or Whatever

Let’s start with the operating system: MS-DOS, version 6.22. This is the final version of DOS that was sold as a retail product, so it would make sense that this was the version selected by the makers of the Pocket 8086 as the operating system for their device, even if it is a little too “new” to be period-correct.¹

According to WinWorld and all the other sources I could find, DOS 6.22 was released in June 1994. This means that the operating system on the Pocket 8086 is more than ten years newer than the hardware base on which its running. I think that’s actually pretty remarkable, both that such an “advanced” version of DOS would run on such ancient hardware, and that even at such a late date in its evolution the operating system was so simple that it was able to run on such ancient hardware without much compromise. It’s a two-way surprise.

So even if 6.22 isn’t quite right for this machine, it means users can access a wider range of supported software and it certainly smooths out some of the rougher edges in earlier versions.

The (Pirated) Arrows in my Software Quiver

Let’s go down the list of use cases and talk about what applications I think might be a good fit for each.

Task lists and work tracking: This seems like a natural fit for Lotus Agenda, a cult classic in the genre and, if I’m honest, the tool that made me want to write this installment of our Pocket 8086 guide in the first place so I’d have an excuse to play with it.

Writing: Since I do this in two different ways–text files and documents–it seems natural to look at using two different tools for it on the DOS side. For a text editor, Borland Sprint seems solid, and for a word processor, since I tried WordStar and found it so inscrutable that I had to give up in despair (and, mind you, this is from a guy who uses Emacs!), I’m going to cheat a little and use a tool I already know a little bit: the legendary WordPerfect 5.1.

Spreadsheets: Nowadays, spreadsheets are very much a monoculture: there are people who use Excel, and there are unserious people who think Google Sheets is a spreadsheet application. In the DOS days, this was much less settled, and there was actually quite a bit of competition. There was VisiCalc, ported over from being the killer app for the Apple II family, but there was also Lotus’ 1-2-3, there was Borland’s Quattro, and several others that all gained significant amounts of market share. For some reason, Boeing even released its own spreadsheet application.² Microsoft’s Multiplan had its following, but Lotus became the biggest and most “standard” of these tools. But standard is boring, so I’m going to try to use Quattro Pro.

Email: Considering that I don’t really have a way to connect this thing to a network and I’m not motivated to try to do it over a serial port, just forget it. Email existed in the DOS era, but I’m just going to have to pretend it didn’t.

Outlining and projects: There were outliners for DOS–ThinkTank made an appearance, and MaxThing–but since I’m ultimately a lover of a Gantt chart, I’m going to take the DOS version of MS Project for a spin.

It’s Time to Go to Work

So, armed with these applications and the Pocket 8086, I sat down to try to actually do … some stuff. You know, computer stuff. Here’s how it went, in order from least interesting to most interesting.

Sprint

Borland Sprint calls itself a word processor, but in reality it’s a perfectly acceptable text editor, with a pretty simple user interface. I actually stuck some .txt files from my laptop on the Pocket 8086’s CompactFlash card, opened them in Sprint, and was able to get right to typing. I didn’t do it long, because the keyboard was too painful, but I have to say: Sprint is a totally fine text editor, and it’s from a time when that was not necessarily an easy task. It’s good, and I like it. It’ll stay on the machine, and I’ll use it whenever I need to edit a text file. That’s much higher praise than it probably sounds like!

Microsoft Project

…I mean, look at this thing. It’s inscrutable. The original GUI version was for Windows 2, and from the screenshots I can find on the internet, looks like it made more sense. But I didn’t try that version, I tried version 3 for DOS, and gave up after about two minutes. The current desktop version of MS Project isn’t exactly a paragon of simplicity or ease of use, but frankly in 2025 the DOS version feels like a toy. I would love to hear if anyone actually used this, even when it was new, because it seems very unlikely.

Project planning of this kind isn’t something I do often enough, and when I do, I’m sure not going to do it on my magic little DOS computer if it sucks this much.

Quattro Pro

I looked at several different versions of Quattro Pro before landing on version 3, which is from 1991. That’s probably a little too new for what I’m trying to do here–this version is very “GUI-ified” and works well with a mouse–but it seemed like a solid choice since I was bucking the trend and not using Lotus 1-2-3. There’s a little more backstory here: Borland was sued by Lotus for copying 1-2-3’s menus, and this is the first version after that lawsuit. The result is very polished, although the Lotus-style menus are still accessible (Note: this Quattro Pro screenshot is from WinWorld because I couldn’t get DOSBox-X to cooperate):

After trying to create one spreadsheet to track how much I was spending on some car repairs this week, my verdict is simple: Mac users had it a lot better than they realized in the late 80s and early 90s.

The early Mac versions of Excel are limited, sure, but they have simple interfaces, they’re easy to use, and they’re logical. Even the later versions of Excel (after we started calling it “Mac OS” instead of “System”) which were basically just ports of the Windows version are pretty straightforward.

It could very well be that twenty-plus years of using Microsoft Excel (I started counting from my high school Computer Applications class) have just hardwired my brain not to work well with any other spreadsheet application… I have the same odd dysphoria when I try to do something with LibreOffice Calc. But Quattro is just too dang hard to use for me to feel comfortable opening it to noodle some calculations the way I do all the time with Excel. It’s functional, sure–it’s clearly a good application, and Borland put a lot of time and effort into it, and because of that I’d be shocked if it doesn’t still have a fan club.

This is probably the one category of tool where I’m just too tainted by modernity to render an accurate judgement, so I’ll follow advice I heard Merlin Mann give on a podcast once and just say, “it’s not for me.”

WordPerfect

This is a tool that has inspired a lot of internet fandom from people who are still using it after all these years, constantly having to tweak and reconfigure to keep the thing working in whatever environment they’re in at the moment. There’s a book about where it came from, which I think Stephen read and did not like. And it has to be said: this is a good word processor, once you figure out how to do anything in it.

One of the challenges of working in the DOS environment is that since there’s no GUI, no standard interface for applications, everybody had to just make up their own and hope people figured it out. This is why the manuals had to be so much bigger: because nothing was very discoverable. Whereas Sprint is a new enough tool to have adopted some of the common user interface conventions from popular DOS tools, WordPerfect was old and big enough to still have its own, and the only way to know how to do anything is to look it up. (F7 quits, if you get lost. It’s still way easier to use than Vim.)

Spend a little time with WordPerfect 5.1 and you see why it inspired (and inspires) such a loyal following: it’s really pleasant to use. The white-on-blue text and the lack of much else on the screen besides your words, the thing you’re working on, make it feel very “minimal writing environment” while still containing enough word processing functionality–this was a very powerful package, especially for the time–to do just about anything. If I’m being honest, I still missed Word, which I’ve always liked (especially Word 5 for the classic Mac, as discussed), but WordPerfect feels lived-in, like a flexible and capable tool. I came away very impressed by how much was already available to users nearly 40 years ago.

Lotus Agenda

Lotus Agenda is an application which has fascinated me for years. I’ve always been obsessed with My System, since whenever I first became a GTD head in college (43F reader, remember?). As such, I’ve used just about everything–from the original Kinkless GTD OmniOutliner scripts and the prerelease sneak previews of OmniFocus, to Remember the Milk,³ to Org mode text files, to a brief dalliance with Taskwarrior, to Todoist in several different stints, Amazing Marvin, even Outlook Tasks and Microsoft To Do.

As stated previously, I’m in Todoist these days, but I’ve always wondered: what if I had a tool that wasn’t cloud based that did everything I wanted, and could run on a very minimal set of hardware and software requirements?

In college I was the main Apple Certified Macintosh Technician at the oldest independent Apple dealer in the state of Tennessee.⁴ Since 1978 these folks had been selling Apple products, but of course, they’d also sold Cromemco CP/M systems, various DOS stuff in the 80s, and whatever else there’d been market demand for back when that was a thing.

As a parting gift when I left that job, I got a fully working Apple II+ with an Applied Engineering Z-80 card and a full set of manuals that is now a permanent part of Stephen’s collection.

I also got this:

Evaluation Copy, indeed…

At the time I’d heard of a modern attempt at recreating Agenda and was inspired to see what all the fuss was about. Problem was, I didn’t have a DOS computer and I didn’t have anything with a floppy drive (even though this copy helpfully came with 5.25″ and 3.5″ disks along with the full set of manuals). It was years before I could actually use the thing thanks to DOSBox. Yes, that’s cheating a little bit: I’ve already used this tool before. But the version I had access to at the time was version 2, which Tavis Ormandy also wrote about excellently here. My disks are actually an evaluation copy of version 1, which I finally found on WinWorld when preparing for this project. Since I have a physical copy of this one, and I have all of the manuals–which Stephen and I may yet scan for the Internet Archive–that’s what I’m using. (I doubt it’s worth sending in the registration cards thirty-five years later, but who knows.)

My apologies to Robert Harmening. Your version of Lotus Agenda has been pirated for decades, apparently.

It’s considerably less colorful than the newer version, of course, white-on-black instead of the soothing blues and grays of version 2. Launching Agenda blind, without reading a lot of documentation first, feels a bit like you’ve stepped into some alien retrofuture where the computer is waiting a command that you don’t know how to give.

Agenda is a very cool application, and for making a simple list of things to do and then looking at it every so often, it’s pretty good! I use a lot of repeating tasks in whatever tool I’m using and Agenda is pretty smart about them. I was impressed by the depth of thought that went into the tool, but even with hundreds of pages of printed manuals at my disposal, it’s just so hard to use compared to even Org mode’s agenda views that I really struggled to use it for a full morning before giving up.

Here’s the reality: I’m already prone to working on my system more than working my system. I love to tweak, fiddle, reorganize, and recategorize my tasks instead of actually doing them. If ADHD is a superpower, call me the Martian Man Hunter. But using Agenda to keep track of tasks, on a system that isn’t multitasking, when so many of my other tasks have to be done on the same computer that can only run one app at a time, just doesn’t make a lot of sense. Agenda is truly a weapon for a more civilized age: you could fire it up, look at your list of stuff to do, probably print it out, and then make your phone calls or do whatever other “not on the computer” stuff people used to do back before screen time ate all of our brains.

The small business owner or sales professional of 1988 probably loved this thing. For me, it was too much work to force it to be what I wanted, but I’m willing to admit that in all likelihood that’s about me and not about Lotus Agenda.

Sidebar: The Cult of Agenda

So I’ve had Agenda on my radar for a while, dating back to the aforementioned 43F post. There are a lot of other people out there with fond remembrances of the application, like this Redditor. There are resources out there for people who still use the application. Certainly it’s had some inspiration on things like Taskwarrior and Org mode, whether the authors of those tools are even aware of it.

As mentioned, Ormandy’s Agenda 2 writeup is excellent. That dedicated core of users is kind of what inspired me to attempt this installment of the series in the first place: some people really loved these tools and have never found anything that gives them the same feelings of clarity and control. For me, that’s probably still Word 5 on the Mac, but it’s very easy for me to understand how it might be a DOS-only PIM app for others.

People get attached to their tools; it’s human nature. We take care of them because they take care of us, and that goes to the root of what it is to use computers to do things–the whole reason we have them in the first place. It warms my heart to see these applications, decades later, still have admirers, and thanks to the quality of modern emulators, they’ll probably be able to run them in some form or fashion until we all run out of electricity and/or fresh water.

(So, another five years or so, right?)

In Conclusion: Is Any of This Stuff Useful to Me?

I’m trying to separate the experience of using these applications from the experience of using them on the Pocket 8086, because I really, really want to love it, but the godawful keyboard just makes that an impossibility.

That’s actually the most disappointing thing here. I wanted to be able to use the Pocket 8086 the same way I used my beloved Handspring Visor: a little helper that I could consult as needed to get me through my day, telling me what was on my priority list and serving as a little scratchpad for ideas and calculations throughout the day.⁵

It was impossible because the thing was just too damn painful to actually type on, and that’s before you account for the fact that I couldn’t figure out how to use Colemak on the thing. The rest of the hardware is fine! I like the size, and the screen is perfectly acceptable. But the main method of interacting with the thing is even worse than I said it was in my initial review.

I wasn’t planning on addressing the Mac at all in this series, or really even spending much time thinking about it. But my main takeaway from this installment is that Mac users, in the late 80’s, had it a lot better than DOS users, even though the applications available on DOS might have been more capable. The Mac versions of Word and Excel are easy to use, and easy to figure out. For basic text editing, you already had BBEdit not long after this era, but even before then, the options were fine. There were more and better outliners available (that wasn’t even a MORE reference, but that’s a great app). The only thing I couldn’t find an analog for on the Mac that I like better was Agenda, and it might be fun to make one!

I really wanted to come away with this newfound love of DOS applications. In a way I did, but what I really wanted to do was get back to the days when I wrote an entire short novel in Word 5 in Basilisk II. (Even if Stephen would prefer AppleWorks)

These tools are capable, powerful, and flexible, but they’re just too hard for my little brain to use in an intuitive way, and they’re all so different. There’s a lot to be said for everybody having to use “Command S” to save.

What I’m really hearing myself say is that I need to buy another PowerBook 180. Maybe Stephen’s got an extra; that eMate of his used to live at my house, after all. Or maybe I need to put new batteries in my Visor. Or, maybe, I just need to use the tools that I like to use and look to the future instead of the past? That one seems unlikely.

Up Next

On deck for the next (and final) part of the series: what is permacomputing, and what does it have to do with a Chinese-made PC/XT clone in a netbook case?