I hope Microsoft's Cortana can rescue me from my chaotic digital life

There are some people whose computers resemble carefully curated gardens, with each and every properly-named file saved to a properly-titled folder, placed in a perfectly sensible order.

I am not one of those people. I suspect I am not alone.

When I need to find a coupon, I sift through my Gmail. When I need to find a picture that I downloaded, it's a mad scramble through files and folders to figure out where it went. My Dropbox account is a wasteland of expired rebate forms, ancient term papers, and memes that I must have thought were funny at some point.

It's only accelerating, too: IBM says that every day, humanity creates 2.5 quintillion bytes of information, with 90% of the world's data being created in the last two years alone.

As mobile devices proliferate, there are tons of people with tons of stuff sitting in apps and in cloud storage that's difficult to sift through on a tiny screen.

This problem has not gone unnoticed. And it turns out the simplest solution is to make it a conversation.

Magna Cortana

If you can ask your device for something, in plain English, and it can give you the answer you were looking for - well, that's the holy grail. It's not just about voice recognition; it's about the ability to "read" a sentence and know what you're talking about.

It started with IBM's own Watson, which was able to fake "knowing" English well enough to clean up on Jeopardy (I've had the chance to play Jeopardy against Watson, once or twice, and I can confirm it wasn't a fluke).

The idea hit the mainstream with Apple's Siri virtual digital assistant, paving the way towards Google Now and Microsoft's Cortana. Siri is a little long in the tooth these days, with hardly a major update to her smarts in some time.

But Google and Microsoft are aggressively focusing on this problem: Both of their digital assistants try to scrape what you probably need to know based on the contents of your e-mail and search history. They're still pretty far from that holy grail, these days, with their abilities to answer complex questions getting very limited.

But both of them are getting smarter. Personally, I prefer Cortana, because Microsoft wisely assigned her a little bit more of a personality, based on a character from the popular Halo games for the Xbox.

Holy Grail

The coolest part of Cortana, to my mind, is the fact that Microsoft is putting her to work as part of the company's newfound focus on productivity.

Microsoft's Cortana Analytics Suite lets a business user take their data and ask simple questions ("Which product sold the most in which stores?"), without the need for any kind of specialized know-how. IBM does something similar with its Watson Analytics.

On a more day-to-day level, Microsoft's GigJam is a Cortana-powered skunkworks project that lets you ask Cortana for very specific files ("Where's my expense report from last July?") and ask her to share it with colleagues for you.

In both cases, Cortana speeds up the time it takes to find answers to what you're looking for. It's your files and your data, but it's faster.

Blueprint

There is, of course, a huge caveat here, and it's the reason these companies are investing in this in the first place.

Microsoft's Cortana will be able to work with Google Drive and Dropbox, but only on Lenovo PCs. Everybody else will be out in the cold. In the meanwhile, Google Now has been aggressively partnering with companies like Runkeeper and Zipcar to get more data pulled into its service.

In other words, it's another platform war. If you choose Google Now, it's a strong argument for keeping your digital life (and your personal data) with Google, since it'll be way more useful to you that way.

If you choose Cortana, well, she's better with Microsoft's own services, which is a major growth area for the company. This is also a big part of why Cortana is built straight into Windows 10 (you can use Google Now from a browser on any computer). It's also why she's coming to Android and iOS.

These digital assistants are the future, giving us the interface we'll need to swim in our deepening seas of data. Just remember that there's no such thing as a free lunch.