You’re Not an Enterprise (Premium)

In The DIY Personal Productivity Tech Stack (Premium) I discussed how one might take advantage of the boom in new productivity tools, many AI-based, and many increasingly from smaller companies that, to date, haven’t been struck dumb with enshittification. To be clear, this isn’t a new phenomenon, there have always been alternatives to whatever mainstream apps and services that most use out there. But it feels like we’ve entered a golden age for productivity tool alternatives.

If you’re familiar with my work, you almost certainly know I have a certain penchant for wordiness. This is something I sometimes struggle with, and as I noted in the most recent Ask Paul, it’s been a problem for as long as I can remember. I would routinely turn in 1000-to-1500 word editorials for an email newsletter I started writing in 1999, and my editor would routinely complain, one time reminding me that they only had to be 500 words in length. At the time, I felt that certain ideas required a certain amount of space to be expressed properly. Today, I’m not so sure. But all I can do is try.

I mention that because it factors into what I’m doing here.

While writing the DIY article, I was suddenly reminded of a confluence of intertwined ideas dating back to those days of 25-ish years ago. And it occurred to me that this thing I was writing, could head off in a slightly different direction. I had a few choices. I could add more content to the article, making it wordier, something I’m trying to avoid. I could rewrite it so that the focus was more on these new, intertwined thoughts, but that’s a tough thing to ask of any writer, and I felt pretty good about the article as it was. So I went with door number three, which you’re reading now. A follow-up to the original article, one that heads off in a slightly different direction.

This is going to take a lot of words. Sorry.

? Left turn number one: Office

I have referenced Steven Sinofsky’s book Hardcore Software repeatedly since I first read and then reviewed it one year ago. Indeed, I have re-read this book repeatedly over the past year, sometimes front-to-back, sometimes in reverse, and sometimes to read the chapters that cover specific time periods. On my most recent re-reading, I specifically went back to the time he spent in the Office organization. And while this observation wasn’t new to this go-round, what struck me most was how Office had evolved as a product, addressing different markets over time. And it’s relevant to the discussion we had in The DIY Personal Productivity Tech Stack (Premium).

Everyone probably has a rough idea about Microsoft’s progression from developer languages and tools to applications and then operating systems in the early years. And most are likewise familiar with the company’s early motto, “a computer on every desk” (which was internally and then publicly expanded to include “running Microsoft software”). Lost to time is that the original vision was for Microsoft software to run on every personal computing platform imaginable, and not just on the PC (which didn’t even exist until 6 years after Microsoft was founded).

But once word processors like WordStar and spreadsheets starting with VisiCalc transformed the earliest personal computers into productivity tools, Microsoft jumped into this new market, bringing its growing set of productivity apps to the relevant computers of the era. For example, a Commodore 64 user could have bought Microsoft Multiplan at a Toys ‘R’ Us in the early 1980s, unaware of how the world was about to change. The important point here is that this when the market Microsoft targeted shifted from enthusiasts, the hardy souls willing to spend hundreds if not thousands of dollars on a personal computer that may or may not ever “do” anything, to more mainstream users, or individuals.

By the mid-to-late 1980s, the personal computing world was basically the PC (and compatibles) and the Mac (really Apple, though Microsoft, like Apple, began ignoring the Apple II line once the Mac arrived). And so that became Microsoft’s focus, with its PC-based work shifting from MS-DOS and to Windows by the early 1990s. (Let’s not muddy the waters with Xenix and OS/2, two short-lived and ultimately fruitless alternative realities.)

This is when the first Microsoft apps that would later be associated with the Office brand appeared. It shipped Word, an update to Multi-Tool Word, on MS-DOS in 1983, to take on WordPerfect. And it shipped Excel, a spreadsheet and follow-up to Multiplan, on the Mac in 1985, to take on Lotus 1-2-3. And then it acquired Forethought, makers of a business presentation app called Presenter (for the Mac, later renamed to PowerPoint) in 1987 for $14 million, its first significant acquisition; Microsoft launched its first version of PowerPoint (1.01) that October on the Mac.

Bill Gates announced Microsoft Office at COMDEX in August 1988, but the first version of this bundle of Word, Excel, and PowerPoint didn’t ship until mid-1989, on the Mac. The first Windows version followed in late 1990. From there, Office went through a series of strategy shifts, with each release focusing on adding new features, a key issue that customers–and reviewers–were focused on at the time. The first shift was from bundle to suite, this is when the separate apps were integrated, visually and functionally, PowerPoint, which lagged the other products, was brought up to speed, and all the apps started being updated in lock-step when possible. Tied to the new features being added with each release, Microsoft also added new apps, like Schedule+ (which later morphed into Outlook) and Access. And it worked to ship Office versions in different countries and languages simultaneously.

Office was often asked to align its releases with Windows, then the center of the company and its broader strategies, but this was rarely possible. Part of the problem was that the Windows team (really, teams) was a chaotic mess that never hit their promised schedules. But Office had developed into a well-oiled machine that rarely missed schedules. This ideally positioned Office, as an organization, to make its next major shift. Instead of focusing on individuals, it shifted to the more lucrative business market. It expanded support timelines and it began offering subscription-based licensing.

Office got caught up in the Internet just like the rest of Microsoft in the late 1990s, and by then Sinofsky was leading that team and being criticized for not embracing HTML-based file formats and Java. But he realized that embracing new, unproven, and inferior technologies was a diversion and a dead-end, and that Office was perhaps best suited as a creation front-end for content that may or may not be displayed online. Microsoft acquired FrontPage maker Vermeer, created the OneNote note-taking solution, and expanded into servers, most notably with Exchange and then SharePoint. It kind of goes from there.

At one point, I identified the point in time in which Windows forever went in the wrong direction, rejecting its push into open, web-based technologies and embracing incompatible, proprietary solutions it had to build from scratch, setting it back years if not decades. Though it was hugely lucrative and probably inevitable, Office reached a similar milestone, or inflection point, at least from the perspective of those individuals who had come to rely on the products for work. And that came when it completed its shift to focusing on businesses with the release of Office 2000.

There were tons of new features, as always, but they targeted the needs of companies, not people. And not just companies, but enterprises. Microsoft’s Enterprise Agreements (EA) scheme, which by this time involved Windows (with Windows 2000 Server and on the client), resulted in record profits and revenues. Microsoft was concerned with meeting the needs of CIOs. And those CIOs were concerned with things like “total cost of ownership” (TCO), deployment, migration, and management. They were concerned with bloat, too, but unable to accept a less bloated Office that didn’t include all the features everyone needed. But one thing was missing from Office 2000. A single major new feature aimed at individuals, the real people who really used Office.

“The middle age of the PC was upon us,” Sinofsky writes on this era. “The age of designing for the individual, the lone hero using the PC as a tool of empowerment, was over. The tinkerer and influential end-user moved from the garage or basement to the office of the chief information officer, the new power seat in the boardroom. The PC was a tool of corporations, and Office needed to deliver that if it were to stay relevant. With Office 2000, the business results suggested that we were spectacularly relevant.”

To businesses. But not to individuals. And I wonder now how or why this didn’t trigger a disconnect with me and with others like me, the “tinkerer and influential end-user” who should have immediately felt slighted by this release and might have gone in a different direction.

If only there had been one.

?‍? Left turn number two: Going insane

Of course, by this time, I was working for an organization that had started as Windows NT Magazine and would morph into Windows IT Pro after a few branding pit stops along the way. And so in the same way that Office, and Microsoft more broadly, was embracing the needs of businesses and the lucrative revenues they delivered, I, too, was shifting. I was learning about, and writing about, business products and services, even though my heart and key interests never strayed from personal technology.

It’s interesting how these things happen. If you think back to the dawn of the personal computer era described in part above, it wasn’t until Dan Bricklin and his revolutionary VisiCalc spreadsheet app for the Apple II that these first personal computers were seen as tools instead of toys. Indeed, VisiCalc triggered a shift of its own when individuals who suddenly couldn’t understand doing their jobs without this miraculous new tool forced Apple IIs into their workplaces. The success of personal technology was driving adoption at work.

As interesting, this shift reversed itself with the popularity of PCs and Windows in the early 1990s. This triggered the adoption of PCs at home, where in essence having a PC with Windows and Office (or, at first, third-part apps) led to success of this platform at home. Just as alternatives like the Amiga and Atari ST crested and then imploded, Windows 3.0 arrived along with Office, and suddenly, everyone needed–wanted–a PC. The arrival of the game Doom triggered a similar boom of popularity, as did Windows 3.1 and then Windows 95, with the Internet then escalating this shift even more.

By the early 2000s, however, and the shift from individuals and smaller businesses, a market Microsoft called workgroups, to enterprises, computing went professional. And in my world, in the IT space, there was a sudden desire among people who frankly should have known better to run their home computing environments as if they were an enterprise. This made more sense–to them–as broadband and home networking capabilities arrived.

But this was always a mistake. It pains me to admit that I briefly went down a path in which I would have a Windows Server at home, running Active Directory, and that I saw a future in which each PC, and the family members who used them, would be managed from on-high. By me, the lord overseer of this insane system.

? You’re not an enterprise, and neither is your family

I did create that AD environment, and I maintained it for years. But I was saved from this foolhardy scheme by less formidable options, like Small Business Server (SBS) and then Home Server. And I never forced anything like this on my family. Who would have rightfully rejected this stupidity. But I know of many others, some at Microsoft, many outside of the company but in the IT space, who did do this sort of thing. It’s a dark period of which we will speak no further.

But I will say this. This head fake into the enterprise world was instructive. It showed me that there can be business software and solutions and that these things can happen in parallel, but separately, from software and solutions made for consumers, or individuals. People. Personal technology. And we also had a guiding light by this time to show us the way. Steve Jobs had come back to Apple and infused the Mac with an enterprise-grade OS, originally built on UNIX and designed for higher education and business, but morphed into something that real people could use. Apple delivered personal tools for people.

Over the ensuing years, Apple itself morphed into something else, too. It always landed neatly in this personal “niche,” which is arguably the biggest audience group there is in technology. But it expanded beyond PCs, first into MP3 players with the iPod, and then exploding the entire market by remaking the market with the iPhone. In doing so, Apple Computer became just Apple. And then it became the biggest company in the world, a dominant force in a market that for most of the previous three decades, had been controlled solely by Microsoft.

This, too, should have triggered a disconnect for people like us. But many of us resisted Apple, for reasons both understandable and not. And instead of buying Macs and iPods and iPads, many of us simply soldiered on with Windows PCs, which ended up OK, mostly. But also went down a lot of dead-ends with Microsoft products like Media Center, Zune, and Windows Phone. For reasons both understandable and not. These things are difficult to explain, even with the passage of time.

?️ The right tool for the job

Bringing this home, and combining the various thoughts expressed here–in the amount of space they needed to be properly expressed, one hopes but knows otherwise–with what I wrote previously in The DIY Personal Productivity Tech Stack (Premium), I think you can see that I’ve arrived at basically the same place. Albeit it from a slightly different direction.

We are awash in choices when it comes to personal productivity apps and services. These choices range from expensive, high-end products, typically provided by Big Tech, to mid-tier solutions from smaller companies like Notion and Proton, to one-off apps created by even smaller companies or even individuals. We can go all-in on some ecosystem, hand-pick individual apps and services, and everything in-between.

This is a personal decision. But when you think about what enshittification really means, and how this impacts you as an individual, I feel like we’re being pushed in an obvious direction.

One might argue, for example, that Office started down the path towards enshittification when Office 2000 focused solely on the needs of the enterprise. But surely the move towards subscription-based licensing, which came to consumers with Office 365 Home and Personal (now Microsoft 365 Family and Personal) in 2013, was a major milestone, too. Like most things, it’s not all bad: I have long argued that Microsoft 365 is a “no-brainer” for families, in particular, thanks to the online storage alone. But enshittification rarely arrives as a slap to the face, it’s usually a slow grind until you wake up one day and wonder where it all went south.

Put simply, enshittification is when a company–Big Tech or not–designs a product in such a way that it knowingly harms users or undermines their needs and wants specifically because it is more lucrative for it to do so. Applied to personal productivity products and services, one form of enshittification is when those things are not designed for your needs, but for others’ needs. This can mean they’re designed for businesses, not people. But it can also mean they’re priced for businesses, not people.

Stepping outside the Microsoft sphere, consider Adobe and its best-of-breed Creative Cloud products, especially Photoshop and Premiere Pro. For a long time, these were overly expensive standalone products that professionals gladly paid for. And Adobe even released–and still makes–less expensive Elements versions of those products that are still sold as what Microsoft describes as standalone, “perpetual” offerings. But the professional products are not. Adobe, like Microsoft, has embraced the subscription licensing model. And if you want to pay, you gotta pay. And then keep paying.

But there as in the more traditional productivity space, we have alternatives. I now use Affinity Photo 2 instead of Photoshop, for example, and I paid for it one time and can install and use it on as many PCs, Macs, and iPads as I want. This experience is so positive that I have no doubt I will gladly cough up whatever they ask for some future 3.0 product. Likewise, I used to use Adobe Premiere Elements, but I’ve since switched to Clipchamp, which is mostly free. Here, I do pay for a monthly subscription because I see the value in that, and I value the simplicity of the app. But there are so many good alternatives now, from professional grade but somehow free offerings like DaVinci Resolve to more consumer-friendly (and likewise free) offerings like CapCut. I use a free app called OBS Studio for my screen recordings, too.

Adobe, like Microsoft, has been quite successful targeting businesses and, in its case, what I’ll call professional creators. And I don’t begrudge either company those successes. They’re deserved. They’re serving real needs.

But maybe those needs aren’t our needs. Maybe we should be smarter and the products and services we choose and use. Maybe–probably–they won’t be the same solutions that businesses choose. And as I reflect on this now, I wonder why I ever thought differently. Again, these things are difficult to explain, even with the passage of time.

But it’s never too late to change. He says, having written over 3,000 words to express what is ultimately a simple concept. You’re not a business, let alone an enterprise. Maybe it’s time to stop pretending otherwise.