The art of tidying up your digital life

My Facebook posts echoed many of the articles hitting the Internet about people feeling happier and experiencing a stronger sense of well-being in their personal spaces.

However, that magical lightness evaporated immediately when I moved from my Facebook tab to my inbox, a lawless land overrun with nearly 12,000 unopened emails. I hastily made my way back to Facebook and asked my friends if their digital clutter weighed on them the same way the mess under their bed does.

While some people saw managing their virtual space as a way to wrangle their real world anxiety, others found their quest for “Inbox Zero” hopeless, and some said the digital disorganization doesn’t bother them in the least. When they shut their laptops the mess is out of sight and therefore out of mind. 

One person pointed out that storage is fairly inexpensive, so why bother worrying about how much virtual space you’re consuming? They’re not wrong. Vivek Sharma breaks it down for us on the USC Marshall School of Business blog: “In 1960, the cost of storing one GB was an astounding $2 million. For the same digital storage, costs decreased to $200,000 in the 1980s, $7.70 by the early 2000s, and, incredibly, just two cents by 2017.”

Technological advancements have made digital storage space more affordable than ever for consumers. So, it’s true it will cost you very little to sprawl out with your data. But if you're not mindful about it, you risk finding yourself at some period in the undetermined future stressed out about your digital mess.

Zack Pennington, sales manager for the data intelligence firm EdjSports, applies a bit of wisdom from those in the medical profession to his digital life, “The only difference between hoarders and collectors is organization.”

Pennington’s default tactic is to save everything. He’s hanging on to as much of his data as he can for the same reason scrapbooking is a 2.5 billion dollar industry: he wants something to look back on when he’s older. His hope is that he’ll be able to “recreate the memories of [his] youth if the data exists somewhere.” And anyone who’s ever been asked by Facebook to tag themselves in a photo uploaded by someone else can sense his dream isn’t too far off from reality. So, Pennington suggests, “Capture the data, then process and organize it later.”

Conor Woods, Dropbox project manager focused on collaboration tools, agrees that the issue isn’t what you save, it’s how you save it, “One thing that’s really important to me is having good naming conventions just so that I can search for stuff effectively.” Unlike a physical storage unit, Woods says when you use good naming conventions “it doesn’t matter if all your stuff is in one horrible pile” because you can type exactly what you need into a search box and retrieve it right away.

Also, the machine intelligence powering the modern cloud platform search function is more likely to serve up the file most relevant to your needs, and not some obscure thing you tossed in a folder years ago but has kind of the same file name.

And that’s just your personal digital space—what about the mess that can happen with everyone swapping and sharing files in the workplace? Woods says this is where good design and good habits come together, “Consistency is key.

That's why we designed Dropbox Business in a way that ensured everyone saw the team's folder structure the same way. Otherwise you'd get all of these people asking, 'Where's that folder? I don't see it,' because everyone set up their accounts differently. This way, the team has a structure that works for them, and everything else falls into line."

It doesn’t matter if it’s personal or professional data, Woods says the rules don’t change, “I think the thing I keep emphasizing is picking a system or a structure — whether it's an organizational pattern, a file naming convention, or something else — and sticking with it.” If you’re ready to take on the horrible pile, Woods who likes to keep things organize online and off, has some tips.

Woods says, “People let their digital lives get cluttered for the same reason they let their physical lives get cluttered. Things start to accumulate pretty slowly and then eventually it reaches a point where it feels like too much work to actually do anything about.” 

If you’re at that point, Woods recommends starting with the most attainable segment of your digital life. Photos can be daunting, but general documents are more manageable, “I call it life administrative stuff, like tax receipts or when you get your car serviced and they give you that little slip of paper that falls under the floor mat of your car and you never check it out again.”

To save those documents from becoming lost or cluttering up your physical space, Woods’ fix is to create a Dropbox folder labeled “My Documents” and store all those docs there. He’s noticed many documents, like instruction manuals and warranties, now come in a digital format, but if they don’t he just scans the docs right from his phone using the Dropbox app.

In your “My Documents” folder you can create sub-folders for Home, Family, Financial and Car. And it’s easy to give anyone who needs it access to these important folders, which can really make a difference when families are faced with navigating a crisis or a loss. If you have no interest in seeing your massive life archive Dropbox folder, you can “uncheck” it through selective sync and it won’t be visible from your computer.

I had a few mom-friends on my Facebook thread concerned about the thousands of photos on their phone, but they were loathe to sort through them all and resistant to mass deleting them because they didn’t want to accidentally get rid of any of the precious moments they’d captured of their children.

Woods’ tips for organizing your photos is to begin by sorting them by year. Then sort each year by month. Review each month’s worth of photos at a pace that’s comfortable for you. Going forward, he also recommends creating a folder for each member of your family and dropping the photos in the appropriate folders as you take them.

To effectively launch your organization efforts, Woods encourages you to use the energy created by “life transition moments” to get you going. This could be the start of a new year, a birthday, a new job or even just purchasing a new laptop.

When I bought a new laptop in December, I decided I needed to go through all the files on my old one and only transfer what I really needed to my new laptop. This process dragged on for so long, the battery finally started to die on my old laptop and I was forced to transition everything over to my new one. 

In the end, I decided a perspective shift was easier than actually facing my digital clutter. I’m now looking at all these emails, photos and miscellaneous files as a digital time capsule I look forward to unpacking in the future. Don’t tell Marie Kondo.