The DIY Personal Productivity Tech Stack (Premium)

When it comes to personal productivity, one could go all in on Microsoft or Google, or dive into emerging suites from Proton and Notion. But there’s another way, one that can involve these players or not. Thanks in part to AI, there’s a growing set of products and services out there that undercut the more traditional offerings. We are suddenly awash in disruption and change.

How did this happen? Simple. It’s always happening. It’s just that AI is making this natural cycle churn even faster than before.

? To the web!

In March 2006, Google acquired Upstartle, a Silicon Valley startup that had created a web-based word processor called Writely. Then, 7 months later, it delivered a “completely re-jiggered Writely” as Google Docs, alongside a Google Labs project that was renamed to Google Spreadsheets (later, Sheets). And just like that, it was on. Google, which had formalize and perhaps perfected website indexing with Search in 1997 and then revolutionized email with Gmail in 2004, was taking its most overt action against Microsoft yet. What was next? A Google operating system? (Yes! Android arrived in 2008, of course.)

It’s easy to forget how different the world was in 2006.

Microsoft was finally about to get past the Longhorn debacle with the release of Windows Vista that November. (And, then again in January. You know what? Let’s just move on). And it had just unveiled Office 2007 that March, right when Google acquired Upstartle. Office 2007 shipped in November–and, then again in January, sound familiar?–and you may recall that it was the first version of the suite to include the ribbon user interface while adding the Office Open XML file formats and a workspace called Office Groove that represented Microsoft’s first fumbling steps into a more sophisticated way (than email) for workers to collaborate on documents.

But Google and Google Docs would change everything. By democratizing document creation and collaboration on the web, just as it had previously with email, Google was showing us a different way forward. A web-based way forward, one that didn’t necessarily require Microsoft or its Office suite. Indeed, I omitted part of the story. Google also announced Google Apps for Your Domain in August 2006, combining Gmail with Google Talk, Google Calendar, and the Page Creator, a website creation and hosting service that was later renamed to Google Sites. Alarmingly, for Microsoft, there would be free and paid versions of this service. And when the paid version, Google Apps Premier Edition, debuted the following February, it included Docs and Spreadsheets.

? Google, start your photocopiers

This was an interesting era. To me, as the Microsoft guy, it seemed that Google was setting out to duplicate everything that Microsoft offered, but usually free and always web-based, or what we would now call cloud-based. This presaged the looming transition from on-premises to cloud, and the battles that would unfold over several years. But in 2006 and 2007, Microsoft was still stuck in a rut, of sorts, unable or unwilling to move past its traditional offerings. Google finally lit a fire under Microsoft, however And through a series of initiatives that included intranet and team website capabilities in Sites (an affront to SharePoint), an Outlook sync plug-in for its email, calendar, and contacts management services, and more, it prompted Microsoft to act.

Microsoft introduced an online hosted offering for enterprises called Business Productivity Online Suite (BPOS) in 2007, but it didn’t really gel until it was re-released and improved as Office 365 in 2010. Microsoft also shipped Office 2010 that year, expanding the use of the ribbon to more apps while introducing new features like Backstage. But this generation of Office products and services was, and still is, most notable for its Google-inspired offerings.

In addition to Office 365, Microsoft added co-authoring support in Word, PowerPoint, and OneNote on Windows. And it shipped Office Online, the first web-based version of the core Office suite, with, yep, a free version too. That latter product was something Microsoft could have shipped years earlier–Steven Sinofsky had pressed for such a thing for several years before moving on to lead Windows development–but didn’t for a fairly typical reason. It was seen as something that would undercut its lucrative paid Office apps. But no more. Now it was seen as necessary, a hedge against the growing Google threat.

? Google, Disrupted

This is how disruption happens. Not that the outcome is always clear. Google didn’t “win” this battle per se. A decade and a half later, Google Workspace still plays second fiddle to Microsoft 365 (just as Google Cloud does with Azure, I guess). But Google entered a market that was dominated by an entrenched monopolist in its unique Googly and web-centric way, and it changed things. Google Workspace today is a viable offering that generates billions in revenues each quarter (as does Google Cloud) and its biggest strengths, to my mind, were that it undercut Microsoft’s pricing, making it ideal for startups, smaller businesses, and cash-strapped educational institutions, while offering what a set of features ranging from what I’ll call a “good enough” to truly innovative.

But that was almost 20 years ago. Things have changed yet again.

Today, Google is the entrenched monopolist, in this case with Search/advertising, Chrome, Android, and YouTube, though it has a suite of other offerings–Gmail, Drive, Maps, Photos, and so on–used by billions and billions of people, too. Google is a pervasive, unavoidable fact of life today. But it has also grown so big and so powerful that it is succumbing to the same inability to change that dogged Microsoft in the 2000s. It invented numerous AI innovations in-house–the “transformer” in generative pre-trained transformer (GPT) is an AI model architecture created by Google researchers in the 2010s, most obviously–but didn’t bring the biggest of them to market out of fear that doing so would undercut its lucrative Search-based advertising revenues.

So now Google is being disrupted, on multiple fronts, by smaller, faster-moving AI startups like OpenAI, Anthropic, DeepSeek, and many others. And like its established tech rivals, it is racing to make up for that mistake. It is perhaps ironic that it was Microsoft that kicked off this AI race. One has to believe that revenge played a critical role in that decision.

? Productivity matters

AI and the models that now power everything running in the cloud and, increasingly, our personal devices are inevitable, a looming “commodity,” as Microsoft CEO Satya Nadella once opined, something that will be everywhere, and in everything. But looking specifically at the personal productivity space, as I think of it, we’re also in an era in which smaller players are once again challenging the status quo. The key difference this time being that the status quo isn’t just Microsoft/Office, it’s also Google/Workspace.

AI plays a critical role here, but it’s not just AI. Indeed, the current revolution started before the AI race began with a seemingly endless list of startups challenging not just the products we use, but also how we work. Slack introduced us to chat-based collaboration, triggering Microsoft to create Teams. Notion burst on the scene as a way to collaboration interactively and visually on ideas, replacing OneNote, Evernote, and similar apps from a bygone era. Proton introduced a growing set of products and services with privacy at their core, quickly expanding into email and calendaring, and then document creation and cloud storage. And Markdown forms the bedrock layer of many, if not most, of these new productivity tools by being perfectly aligned with their ideals of being smaller, faster, and truly open.

Circling all these things are a million sparks of light, individual services, now typically AI-based, that make what we’re doing better. This includes spelling and grammar-checking services like Grammarly and LanguageTool, but also writing improvement services of all kinds, generative AI-based image and video creation capabilities, and a lot more. We’re in a new age of personal productivity innovation. Things are changing yet again.

And that means that those still stuck in the traditional Microsoft Office space, or the suddenly just as traditional web-based Google Workspace/Docs space, have new alternatives, a collective escape hatch that will take us from the past and into a more efficient future. Through no plan at all, other than just a desire to keep testing alternatives to the products and services I rely on, I’ve made steps away from the Microsoft-centric productivity space over the years, not because I don’t “like” Microsoft or want to use its products, but when I find things that are objectively better for me to use. Notion is an obvious example. Typora, the Markdown-based word processor. LanguageTool, which helps me edit my spelling and grammar when I paste my writing in this (WordPress-hosted) website. Google Drive instead of OneDrive, though maybe someday that becomes Proton Drive. And so on.

A few years back, I came up with a pithy tagline for this site, that I still like: “Personal technology, with a focus on productivity, mostly Microsoft.” I may need to change that last bit. I’ve evolved with the times. But Microsoft has not, at least not with the personal productivity tools that I need. It’s OK. This isn’t a religious issue. I just want to use the right tool for the job. The best tool. Whatever that might be.

And what that might be … will vary by person.

I see those pushing back against the AI and enshittification that’s expanding throughout Microsoft’s end user products in interesting ways. Some are trying standalone Office suite versions instead of subscribing to Microsoft 365. Some are going with open source apps that have been around almost as long as Office itself, like LibreOffice. Some move to Google Workspace with Gmail and Docs because it’s cheaper and simpler.

But there’s a growing set of cloud office productivity offerings that I find particularly compelling.

Notion is becoming to Google what Google once was to Microsoft, with its core app but also now Notion Mail and Notion Calendar. How this is all free still boggles the mind. Yes, you can pay for Notion, but I don’t, and I’ve never been asked to. I don’t get it.

Proton is getting very interesting too. It offers email, calendar, and contacts management, cloud storage with desktop sync, web-based document apps, password (really, identity) management, VPN, and more.

Notion and Proton would be an amazing combination. But they don’t have to merge or whatever. Not for the first time in our adult lives, you could simply roll your own, picking and choosing the best of the best, no matter the sources. I guess that’s basically what I’m doing.

And increasingly, the best of the best is not coming from Microsoft. Or from Google, for that matter. And that is quite interesting to me.