Week 16 of the Clever Girl Organizing Challenge: Managing Your Digital Life

If you can believe it, we are in our final week of this 16 Week Challenge to reclaim your home and reclaim your life!  Whether you followed along perfectly or just made progress here and there, I hope it’s been a valuable way for you to spend your time and energy so far this year! I want to thank each and every one of you for diving in and inviting me into your homes and helping you get some order into your life!  And, don’t forget about my Virtual Organizing services if you want to continue to work with me, and get personalized and tailored help, delivered right to your computer screen!

In our final challenge, we’re going to address our digital assets.  If that doesn’t mean anything to you, let me be a bit more clear:

  • E-mails
  • Photos on the computer
  • Photos (and other things) on the phone / tablet
  • Electronic files and documents
  • Music in your iTunes (or other) library
  • eBooks in your Kindle (or other) library
  • Passwords and online account management

One of the reasons Digital Assets quickly become Digital Clutter is because they don’t seem to take up valuable space in our home, or are something that we find too detestable to look at every day.  It becomes INVISIBLE CLUTTER, but it’s clutter, nonetheless.  And deep down, you know this is true.

Now, you may think of these and think they ALL need work, or you may find only one or two that thinking about it makes the hair on the back of your neck. As this is Week 16, you may turn this into your own extended challenge for a few weeks, tackling some of it each week.  Whatever you decide, start to take some action to make a difference in this space for yourself and your family today!

Our goal: 

Make sure we have what we need, organized in a manner such that we can find it when we need it, and that it is protected from loss – whether that is human error, disaster, or fraudulent activity. 

(By the way — be sure to come back to the strategy post that I’ll share later this week on managing your digital assets in the event you’re unable to do so — like, if you die or are incapacitated, or your significant other does, do you or someone else know how to find and manage all the important information and accounts?)


16 challenge

Week 16:  Managing Your Digital Life

Level 1 Challenge: Get rid of what you don’t need, and organize what you do. The first step is really acknowledging for yourself which of the category of digital assets is the one that needs the most work.  It may be:

  • Your photos (“I want to get them organized, all in one place, so that I could do something with them”)
  • Your emails (“I have 1200 unread emails in my inbox”)
  • Your digital files (“I have files from previous jobs that are 8 years old, and they’re just taking valuable space on my hard drive, or coming up unnecessarily when I’m trying to search for something important.“)   

But there’s a good chance that something in there has been neglected.  It may take time to address the work that is required here.  So, this week’s Level 1 Challenge is about investing the time and patience it takes to get these current assets under control.

How to tackle this one: First, pick what you think your hottest button is.  You probably know what is in the biggest need, and it’s the one you’ve been putting off a long time.  This week, make it your slave.  Make it work FOR you, and not against you. 

If you are tackling emails, the goal is probably to get to Inbox Zero.  I’ve written about this in the past, so I’ll send you here

If you are looking to get your photos under control, your steps may include getting your photos OFF your phone and tablet and saved with your other digital photos on your computer, and then finding a way to meaningfully organize them.  And I’m going to start with a controversial statement for you to consider:  You don’t need to keep every photo you’ve taken.  You can delete them. Really.  Between de-duplicating for exact copies, and deciding that not every single version of that double rainbow you took 3 years ago that time you were driving through the country, if you really looked at each photo critically to say, “Do I need this?  Do I lose something of my memory of this day or event if I delete it?  Is this even an event that’s important to preserve?” you’ll find yourself being okay with deleting items. Why is this important?  Because storage of photos can be expensive (though there are ways of getting great deals) and more importantly, because it doesn’t help you find what you want when you want it, when you have to thumb through so many other less important items to get there.

You’ll want to consider where you store them (on your own device? or in the cloud?) and how they get ordered (chronologically? by another meaningful order?) and how you name or tag them.  Tagging will allow you to not care too much about what order you save them in, if you want to recall them all in a moment. This means you can tag “Christmas” in pictures, but it doesn’t matter how they’re stored; if you want all the photos of Christmas over time, you can find them all with a tag search.  Facial recognition is just like a tag, only a smart and intelligent way for the computer to do it for you. (By the way…. if you want help with photos — digital or physical or both — consider that you can actually hire and expert to help you! Check out the Association for Personal Photo Organizers to find a certified organizer near you!) 

If you are getting your documents and files, you’ll want to first determine what you truly need to keep, and then, understand if you’re storing them in way that makes it easy to find what you need, when you need it.  Today’s search technology makes it so easy to look EVERYWHERE on your system for items, so it’s not as critical as it might be, but that’s only if you really know WHAT to search for.  If you’re searching for everything related to high school, but you have it abbreviated as “H.S.”, it’s not going to come up if you type “High school”.   And, similarly, you’ll want to think about the best permanent and safe storage for your files.  

If you’re going to challenge your music or ebook library, more of the same advice as above, especially the advice on whether not you need to keep them. Just because you added the album to your library 10 years ago, doesn’t mean it needs to stay there. If you’re treating it like something you’ve collected, rather than something you enjoy, think about whether or not it’s just taking up space. 

Level 2 Challenge: Back Up Your Important Assets.  
This one is all about creating protection for that one moment that is out of your control, and something happens:

– Hard Drive crash
– Virus infection 
– E-mail account hijacked
– Phone lost or destroyed

– Accidental “Yes” to “Delete all?”
– Fire or water damage to your devices


How to tackle this one:  For this challenge, again, choose the hottest button for you. What’s the hottest button?  “If I lost everything here in a moment, I’d feel the most pain.” Then determine a protection strategy (even if this means reaching out to an expert for help) that works best for you and your needs. This could mean:

  • Setting up a regular system and routine to back up your phone/tablet items to your computer, or your computer items to an external hard drive, and making sure you keep another copy in a place that, if there were a fire, you wouldn’t lose BOTH copies
  • Making greater use of cloud offerings like Google Drive and Drop Box and iCloud or Amazon to have off-site storage of your most important documents and photos
  • Consider subscribing to an automatic back up system like Carbonite or Backblaze or Mozy that will automatically create copies of your computer (when you set it up correctly — sometimes you need to take extra steps to make sure your email is backed up)
  • Ensure your phone is being backed up regularly, so that if you lost it suddenly, all you’d need is a new device, but the rest is recoverable. 
  • If you’ve been going “paperless” lately, or if last week’s challenge inspired you to start to try, research the best practices on how to create a good and strong filing structure, so that you know where to put things, so that you can find them when you need them. This could include how you name files, how you use tags, or how you set up folder structures.  It could mean utilizing a system like Evernote or OneNote to help you manage your digital assets off your computer entirely. 


How The Challenge Works:
As With Every Week, Your mission:

1) Take on Level 1, and if you’re feeling up to the challenge, Level 2. If you’ve already got those covered, identify a challenge for yourself that you know you should be tackling.

2) Whenever possible, take BEFORE and AFTER pictures. You don’t have to share them with anyone but yourself, but it is a fantastic way to (a) identify clutter that’s become invisible to you over time and (b) truly measure and appreciate your progress. 

3) We’re all about letting things go…  be critical about what you’re keeping and why you’re keeping it.  Always ask yourself these critical questions to help decide if you should hold onto items: 

  • Is using this item part of my current life or likely future?
  • If I didn’t have this item and needed it for some reason, is it easily replaced or borrowed?
  • Can someone else use this more than I seem to be using it now? 
  • Am I keeping it for a “maybe some day” or a “just in case” option? How likely is that situation? And am I keeping more in that category than I should, given the space constraints I have?
  • Is it part of my past, and holding onto it reminds me of a former self? And am I keeping more in that category than I should, given the space constraints I have?

4) Stay FOCUSED on this task.  Know what FINISHED looks like, and don’t get distracted by other projects or areas of attention that cross your path while you’re on this assignment.  

5) Have a plan on where things will go — give away to someone you know, donate, sell, recycle or trash. This Challenge isn’t just about creating new piles that don’t have a future!

6) Work in manageable chunks of time and energy. It’s a marathon, not a sprint! 

7) Join in the conversation over in the 2016 Clever Girl Organizing Challenge Facebook Group to share before and afters, “what should I do with this?”, “should I keep this?” or any other parts of tackling this challenge you think might benefit the rest of Clever Girl Nation. 

8) Celebrate and reward yourself for a job well done!




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