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Help for the digital hoarder: An easy 3-step guide

I'm Jill. I'm a digital hoarder. And I need help.

Combined, my work and personal emails top 100,000. The habit of managing an email that doesn't relate to what I need has long escaped me. I scan my inbox for what's relevant, deal with it, and ignore the rest. Plus, I'm always worried about deleting some email I don't need now but which might-possibly-not-really-ever become crucial at some mysterious future point in time.

More sinister than the menacing mess of emails I'm plagued with -- the real assassins to the sanity of my digital life -- are passwords. I have at least two dozen to keep track of, and those are just the ones that get used routinely.

Naively, I thought if I kept these passwords organized in one list hidden on my computer, cleverly (or not so cleverly) titled "family recipes," I'd save myself the grief of having to memorize everything and have a handy go-to list shielded from prying eyes.

Finally, in just one year, I've snapped more than 9,000 photos on my iPhone. The images reside on my phone and on my backup terabyte drive in triplicate, because I worry the photos didn't transfer properly.

In the end, all I've really done is increase the heap's size, making it much more difficult to find that photo of my toddler cuddle-strangling the cat, or of me and my mom on an amazing summer vacation. These are difficult reconnaissance missions when you haven't labeled, grouped or otherwise organized the pictures you take.

I sought and found intervention for my digital dilemma with PC Magazine contributing editor Jill Duffy, author of "Get Organized: How to Clean up Your Messy Digital Life."

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"I am not some super genius programmer. I am just a normal person interested in simple processes and how we can make technology easier, simpler and work better for us," Duffy said during a phone call from her current home base in India.

If you suffer from password mayhem, email overload, or a mass of disorganized family photos scattered across devices, this column is for you.

Duffy's straightforward, real-solutions-for-real-people approach may just work for me. A successful intervention hinges on whether the solution is easy, involves little time investment, and comes with a fix-it task that actually yields results. Duffy promises it can be done. Here's how to get started.

Passwords: A quick path to insanity

Duffy's No. 1 tech tip is to get a password manager, because passwords are the easiest to tackle. "You can just be completely oblivious to them and not worry about it," Duffy said.

Why? Password managers will "... generate passwords for you that are strong and unique. Something that computers do very well is generate really strong passwords and humans do very poorly," Duffy said.

Password managers save and remember the passwords you create and can even type them in for you. More sophisticated managers will analyze the strength of your current password profile, comparing the passwords you use at different sites and generate a strength rating. For example, using the same password for banking as you do with other accounts is a safety weakness, and the program will catch it. You then have the option of allowing the password manager to create and remember new ones for you.

PC Magazine's top three picks are Dashlane, LastPass and Sticky Password.

Bottom line: Letting a password manager do the work for you "is a much better solution," Duffy said.

Email explosion

"Here's the thing about email. If your email system works for you and you don't feel overwhelmed, that's OK. The problem is a lot of people feel overwhelmed. It's a psychological, personal issue. It's not about technology," Duffy said.

My email habits fall into the "dipping into the stream" personality type. I just let it flow and dive in and out as needed. But some people worry that lying within all of those unopened emails is some million-dollar deal waiting to be brokered.

To get started, Duffy recommends a process called "sweeping." Create a folder for every past year, and "sweep," either manually or with a filter, all of the old messages into all of the newly created year-by-year folders.

"What sweeping allows you to do is kind of put all of those messages out of mind, with the assurance that they aren't going anywhere," Duffy said.

With a modest cleanup done, you can rest easy knowing the messages are safe but you also have a fresh start for 2016. If months go by and you haven't needed any of the archived folders, maybe then you'll be ready to hit delete.

Next, don't let email rule your life. According to Duffy, most research recommends you limit yourself to dealing with email a few times a day. Barrages of emails are intrusive and distract you from what you're doing. Because of this, "it's really unproductive to be doing email all day long," Duffy said.

Those dedicated "chunks" of email time should focus on one of four things: respond, archive or delete, file into another folder, or complete a task someone has asked you to do.

A plethora of pictures

"Photos are tricky. They are one of these pieces of digital data that we have all over the place. Suddenly we have 6 or 7 places where we have different photos," Duffy said, empathizing with the challenge of organizing the average family album in a world of smartphones and all things digital that have made capturing and preserving pictures easier than ever.

Her best advice? Let go of the past and move forward. Don't worry about the photographic chaos that's already happening. Instead, work on getting a grip on those you have yet to take.

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"Start with today and start a new process," she said.

For phones, start automatically uploading to Dropbox or some other file-storing service. Unlike other services provided by Dropbox, where documents are mirrored from machine to machine, photographs are actually copied. Which means you can delete them from your phone without simultaneously deleting them from Dropbox or other devices.

With an automatic uploader, you don't have to worry about your backlog of photos, Duffy said.

So that's step one: Centralize all photos. Then, if you have time, rename your photos, or consider using another tool that allows you to use facial tagging. Other tools that specialize in organizing photos -- iPhoto, Flickr, etc. -- will allow you to add tags and automatically sort albums.

Naming albums by events or weather events can also help; the week of the gigantic snowstorm, a special birthday celebration, an amazing road trip. If you can group and organize by date, future search efforts become even easier.

Duffy's impressed with Flickr's upload tool, which runs in the background and searches things like your computer, phone, camera, social media and hard drives for photos, then uploads them to a centralized location. She tried the app recently and was pleased with the results, even if it took weeks to complete.

"It just sort of quietly did it's thing in the background and then one day popped up with a message that said 'I'm done,' " Duffy said.

Finally, for people like me who have amassed a ridiculous number of duplicate files that haven't been named or grouped, Duffy said "deduping" software can help eliminate duplicates and can help bring unruly catalogs of precious memories under control.

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I'm Jill. I'm a digital hoarder. But I think I just might be on the road to recovery.

Jill Burke is a longtime Alaska journalist writing from the center of a busy family life. Her father swore by "Burke's Law No. 1 -- never take no for an answer." Meaning, don't give up in the face of adversity. The lesson stuck. Share your ideas with her at jill@alaskadispatch.com, on Facebook or on Twitter.

The views expressed here are the writer's and are not necessarily endorsed by Alaska Dispatch News, which welcomes a broad range of viewpoints. To submit a piece for consideration, email commentary(at)alaskadispatch.com.

Jill Burke

Jill Burke is a former writer and columnist for Alaska Dispatch News.

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