How I Simplified My Digital Life

I hate confusion, I hate unnecessary complication, and I hate, I hate disorganization.

So when I realized that my digital life was becoming increasingly complicated and requiring way too much of my time, I knew I had to take some action.

We need to clear up one caveat about technology before we proceed: contrary to popular belief, technology never promises to save us time. Technology is “the practical application of knowledge especially in a particular area” (from Merriam-Webster). If anything, the promise is that it’s supposed to make things easier by providing a better tool to do something, but that doesn’t inherently save time. However, that doesn’t mean technology taking up time is a good or neutral thing. Anything that takes time aware from our core activities – for me: faith, family, writing, reading, and chill time – should be inspected carefully to see if it’s worth keeping. Hence my dilemma: too much of my time was going to non-essentials instead of the essentials.

So I decided to completely revamp my file strategy, backups, and even the devices I use. I’ll share the process below, but keep the following in mind as you read:

  1. This particular plan worked best for me. Yours may need to be different depending on what services and hardware you use.
  2. I’m pretty integrated in Google, but if you’re integrated in Apple or Linux, or even if you’re a mix, some of the basic ideas can still apply.
  3. This was a long process – probably spanning two to four months. If you’re committed to this, be in it for the long haul. It’s a half marathon, not a sprint.

If you’re ready for simplification, read on!




The first step to any large-scale endeavor is planning. If you want it to be successful, you have to plan it out. And to be honest, it didn’t take that long for me – maybe an hour or two. Here’s what I did:

First, I looked at my current file strategy and wrote down what was important to me: did I want access to all of my documents from anywhere? Did I want access to all my pictures or just some? What about backups from Steam games? Here’s what I decided:

Very important to me:

  • Documents: I wanted essentially all my documents accessible from everywhere. (Some key documents were already in Google Drive.)
  • Pictures: At least some, but preferably all, accessible from everywhere. (Very small amount on Google Plus Photos, some still on my phone and tablet, most not uploaded.)
  • Music: All, accessible from everywhere. (All music already on Google Play Music.)

Pretty important to me:

  • Games: All game saves and non-Steam games I would like to access anywhere, but would settle for local access. (Saves currently local, non-Steam games were local).
  • Videos: Wanted some to most of my videos (mostly digital copies of movies I’d purchased) to be accessed anywhere, but would settle for local, shared access (visible on our Roku through Plex Media Server, or on a future Google or smart HDTV).

That gave me a good beginning idea of where I was and what I wanted.

Second, because I’m mostly a visual/kinesthetic learner, I created a couple of diagrams. This was really useful for me because it gave me an idea of what my current file sharing and backup strategy was and what I wanted it to be. I drew images for the different computers and the “cloud,” used arrows for backup/sharing connections, and wrote descriptions where appropriate. Comparing the “Currently” and “Ideal” diagrams helped me see the solutions that would best fit where I wanted to be when the process was all said and done. (There’s still a lot of detail in the “Ideal” diagram below, but the setup itself is much more simplified.)

Initially I had another option that combined using Drive and DreamHost, but that wasn’t simple enough for me. I wanted to get rid of as much as possible to allow as simple a file backup and access strategy as possible. As you can see in my “Ideal” diagram above, I ended up going exclusively with Google. (I go into further detail on that choice in the “Files and backups” section below.)

Third, once I settled on a strategy I wrote down a step-by-step plan. It was pretty straightforward – since I’m very much a list kind of guy, I just wanted a series of action items that I could cross off as I completed them. Here’s the list I created:

  1. Media server:
    1. Delete and organize files. (This is where I got rid of extraneous files and made sure what was left was organized how I wanted it.)
    2. Backup everything (desktop, wife’s laptop, and media server) to external hard drive.
    3. Separate primary files (Pics, Downloads (half), Videos (some), Games (some)) from secondary files (Music, Videos (most), Games (most), Downloads (half)). (I also did some planning here and figured out how much space the primary files would take up on Drive. While I had guessed 63.86 GB would need to be uploaded (thus helping me choose Google’s 100 GB plan), I ended up using 70.9 GB of my 125 GB allowance.)
    4. Format 1 TB drive that won’t be used – store to the side and label. (This was an extra 1 TB drive in my media server that had remained blank, or used as an extra backup.)
  2. Google Drive:
    1. Upgrade storage to 100 GB ($4.99/month).
    2. Create folders for primary files (ended up realizing this was not needed – you can upload entire folders to Drive, and it keeps the names of the folder and all subfolders).
  3. Media Server:
    1. Upload primary files to Drive.
    2. Remove hard drive (still contained primary and secondary files) and label and store (stored this 1 TB drive on-site; my external that contained all my backups (primary and secondary files, wife’s laptop, etc.) is at a safe, off-site location).
  4. Wife’s laptop:
    1. Setup Drive folder to auto-upload to Drive and configure Drive folder as primary file save location OR don’t automatically backup, just manually backup once a year or every other month (ending up going with the second option).
  5. Other:
    1. Copy save games to Drive.

While that gives you a good idea of what my planning, preparation, and steps were like, what about my decisions? Why did I choose Google, what did I move over, what devices did I choose, etc.? And did my planning work out like I hoped it would?


Files and backups



Probably the first decision I made for simplifying my digital life was regarding Evernote. Previously, I used Evernote for both quick notes and “I access these all the time” notes, and Drive for long-term note storage. But that didn’t really make sense – why manage two services when one can handle it fine?

So I made the decision to move completely over to Google services for note-taking. I kept long-term note storage in Drive, moved “access all the time” notes to Drive, and used Keep for quick notes (mostly to-do items). While you could argue I’m still using two products for notes, bringing all the notes under the Google banner still simplifies the access. Practically, I have Drive and Keep as dedicated tabs in Chrome, and it’s very easy to pull them up and takes 0 effort to manage them.

Google Play Music

This was perhaps the easiest decision to make. Originally, I used iTunes as my primary medium for playing music and movies. I would purchase and download MP3s through Amazon or Google Play Music, organize them in the proper folder in the My Music folder on my desktop, then import them into iTunes. Too many steps.

So when Google offered to upload up to 20,000 songs to Play Music for free (an offer that still stands), I jumped at the chance. I uploaded everything (4,000+), spent a little time organizing it, and now I can access my entire collection anywhere. I mostly listen to music from my phone while in the car, so I just stream Play Music or Pandora and I’m good to go. If I wanted to listen on my computer I’d just go to the website and play one of my favorite playlists. Nice and simple.

Google Drive

This was easily the hardest decision in the entire process. I had to decide between so many different services and variables it became a headache. As I saw it, here were the options:

  • As-is with added access:
    • Already using Drive for long-term note storage and major files. Not too much on there. (Cost: $0.)
    • Using Backblaze as my “if my house burns down what’ll I do” backup strategy. (Cost: $3.96/month for 2 years (have to pay $95 up front).)
    • I wanted at least access to all my main files from anywhere, and it would’ve been nice to have my own website landing page for content. Thought about adding DreamHost for those capabilities, especially since you’re allowed “unlimited backups.” However, due to file access constraints, DreamHost asks you to not use the basic plan for primary file backups and access. (Cost: $3.95/month for 2 years, then $8.95/month.)
  • As-is with Google backup:
    • Keep Backblaze for “house burns down” backup strategy. (Cost: $3.96/month for 2 years (have to pay $95 up front).)
    • Upgrade my Drive storage and backup all my main files there. (Cost: $4.99/month.)
  • Google-centric:
    • Use Drive for all main storage, archive the rest, full backup from Drive yearly. (Cost: $4.99/month.)

I ended up going with with the Google-centric plan for a couple main reasons:

  1. Price. Of the above, the Google-centric model was the cheapest. While it could be argued that for pure storage needs some other companies provide a better price per GB stored, I needed easy access to these files, which leads me to:
  2. Ease of access. I didn’t want to just dump these files and forget about them (that’s what my long-term archival strategy was for). I wanted easy, daily access to all of my main files (~60 GB). Since I’m used to using Google’s services, it’s easy to access them (web or mobile device; even locally, with the Drive program), and it was easy to add storage to Drive, it eventually became a no-brainer (after a couple of hours of headache). Add in the myriad of ways Drive can integrate with existing services and devices and it eventually became an easy decision.

There was one added bonus I didn’t think about until implementing this plan:

  1. Article archiving and storage. While our site has a great backup plan implemented, I like having personal copies of my own work. I now use Drive to save a copy of the article in TXT format, as well as any images I used or considered using. It’s useful not just for article backups but for accessing those files later when updating or creating articles.

This is where your preference for services and storage will come in. I’d enjoyed using Drive enough that I felt comfortable placing all my main files in their cloud, but you may prefer iCloud or the like. They’re your files, so it’s up to you – just make sure you give it some good thought.

Old papers

One of the great bonuses of simplifying my digital life was my decision to electron-ify my old papers. I had a lot of papers from college (some related to my senior thesis, and some with info that would be great for future research) and some random others. I borrowed a fast scanner, scanned everything to an electronic format, and saved it to my archived hard drive (1 TB on-site drive). Originally I was going to upload everything to Drive, but it ended up being much larger than I anticipated. If I decide to increase my Drive storage in the future ($9.99/month for 200 GB or $19.99/month for 400 GB) I’ll probably upload it then.

Old blog websites

This was one of my final decisions – what to do with my old blog websites (have a technology-related blog site and a theology-related one). I had custom URLs for them, and they still see a pretty good bit of traffic, but it was one other thing to manage.

In the end I decided to keep them both. While it’s a little extra money ($1/month per site), they are visited pretty frequently, and I didn’t want to cut people off from some helpful posts. It would’ve been a pain to put in “go to this URL now” notices on each post and try to get everyone moved over to public documents on Drive. If the usage decreases enough I may remove them or replant them, but for now I’ll keep them.




Media server

This is the main device I wanted to get rid of. Trying to manage a file server is a pain in the butt. I had all my files on it, I used it to stream my media through my Roku to our TV, and managing monthly backups was a nightmare. It took too much of my time for not enough benefit. And the extra heat dissipation made the room too hot.

In the end, moving to Drive made the decision for me. Once all my main files were on Drive, I didn’t have a need for a main file storage location. I moved my primary files to Drive, kept the primary and secondary files on a hard drive from the media server, removed it, labeled it, and stored it in on-site (external with all backups is off-site). That way I have the files if I really need them, and I can backup to it from Drive once a year if I choose.

Wife’s laptop

My wife’s laptop became an anomaly – do I provide an automated backup that puts my Drive credentials on another machine, or manually back it up every other month or so?

I decided on the latter – not because I wanted to be lazy, but because it ended up being simpler. She doesn’t have a lot on it, so every so often I’ll just back it all up to Drive in a folder for her, and she’ll be good to go.

Smartphone / Tablet / Chromebook

This was another hard – yet fun! – decision.

Previously, I’d been using a Samsung Galaxy Nexus for mobile connectivity and an ASUS TF300T Android tablet for mobile productivity. Really any smartphone could provide the level of mobile connectivity I wanted, but my Galaxy Nexus had started having some battery issues (possibly because of my own charging strategy, which I’ve since changed). And I had high hopes for the Android tablet, but the lack of a desktop-style browser still made it difficult to edit articles and be as productive as I wanted/needed.

In the midst of looking for replacements I did a review of the Samsung Galaxy Note II and fell in love with it. Then it hit me: why not get a Note II and use it for all it’s worth (added productivity with the stylus, which has been very handy), and get a Chromebook to take care of writing/editing articles on the go?

So that’s the plan I set in motion. First up was the Note II, which I got on the cheap through price-matching and trading in my Galaxy Nexus. It took a little longer to sell my TF300T through Craigslist (also had some hits on Swappa), but that eventually worked out. I used the money to get the Chromebook ($249 Samsung model from Best Buy; generally the higher-rated of the cheaper Chromebooks), and couldn’t be happier. As far as this article is concerned, the main benefit of the Chromebook was simplicity and manageability – I literally have to do nothing to manage it. Since I already use Chrome on my desktop and I’m signed in, all my information and settings are transferred across devices, including the Chromebook. I just open the lid, after a few seconds sign in, and I’m there. The desktop-style browser is also a huge plus – it’s much easier to work on articles on that instead of a mobile browser.

Another side topic related to my smartphone was that of cataloging the installed apps. In order to know what to reinstall whenever I flashed a new ROM or changed devices, I created a couple documents (one for Cell Phones, one for Tablets) that included details about the devices as well as their installed apps. This became a huge pain to manage – imagine removing and deleting app entries every time you installed one. In the midst of this simplification process I realized that Google keeps track of installed apps for me (both what’s on the device as well as a larger list for anything I’ve ever installed or bought), so I just deleted those documents altogether. As an added bonus, I use TitaniumBackup to backup my app data, so I can always use that list to reinstall if I need to.


What my digital routine looks like now


I think it’d be helpful to take a moment and go over what my digital routine looks like post-implementation:


  • I get a couple of emails every day that I either save or save attachments from. I use the Chrome Drive extension to save those files directly to Drive (automatically saves to the main folder). (Time: seconds.)
  • Any other “daily”-type files get saved directly to Drive. (Time: seconds.)
  • Whenever I install a program I want to use on a pretty regular basis, I save the EXE in Drive (as long as it’s not too large; then I move it off for the archive hard drive). (Time: upload time.)
  • Typical email, life-related (bills, etc.), and gaming actions.

Weekly/whenever I remember or notice (don’t put any pressure on myself for these):

  • I put the files from the emails in their proper folders in Drive. (Time: about a minute, depending on the amount.)
  • I play games pretty frequently (just started with Skyrim), and if the game doesn’t auto-save to Steam I’ll save the saved games in Drive. (Time: half a minute.)


  • I perform my regularly-scheduled Bi-Monthly Maintenance. Includes things like doing a full scan with Windows Defender, Disk Cleanup, making sure Windows Updates have been installed, defrag wife’s laptop (my desktop has SSDs), etc. (Time: half an hour for all devices.)


  • I perform my regularly-scheduled Bi-Yearly Maintenance. Includes mostly deep-cleaning procedures like opening up my desktop and using a can of air to blow out any dust. (Time: half an hour for all devices.)


  • Bring back my external hard drive from off-site storage and backup everything from my desktop, my wife’s laptop, and Drive. (Time: unknown; setup will probably take 5 minutes, downloading/backing up will probably take a few hours, but I won’t have to sit and watch it.)
  • Copy that backup to an additional archived hard drive (the 1 TB one that contains previous primary and secondary files) that I keep on-site. (Still debating this one; probably won’t implement since I’m already saving everything off-site and main files are in Drive.)

That may still seem like a lot, and in some ways it needs to be fine-tuned, but it’s a much better routine than what I had previously implemented. At the very least it’s much simpler and a decent time-saver. (Especially dealing with daily files – I just save them to Drive now.)




Overall, I’m incredibly satisfied with the move to more of a cloud-based file storage, access, and backup method. After being on this method for around a month, I’d say these are the pros and cons:


  • File access. Since my main files are on Drive, I can use essentially any computer and device in the world to access my files (barring the 2-factor authentication step, which adds a minute or so to accessing files on any new computer; haven’t needed to do that yet).
  • File backup. This is both a pro and con. On the pro side, I just save all primary files to Drive, which is a near-foolproof backup method. Google takes care of the data replication, so I don’t have to worry about losing a thing.
  • Devices with purpose. I now know exactly how I want to use each of my devices – main desktop for day-to-day computing, no file storage; smartphone for mobile connectivity and mild productivity (stylus, etc.); and the Chromebook for mobile productivity.
  • Time. I used to have a Monthly Maintenance calendar event that listed everything I needed to do on my desktop, media server, phone, etc. every month in order to keep it working properly. Since implementing these simplification steps I’ve not only significantly reduced the number of items in the list, but I’ve made it a Bi-Monthly Maintenance calendar event instead (I also have a Bi-Yearly Maintenance list, but it’s mostly dust cleaning-related).


  • File backup. There is a con side to this – manageability and trust. If I’m saving all my primary files to Drive, that means my secondary files need to go elsewhere. While this hasn’t been an issue yet, no doubt I’ll start getting a pile of files on my main desktop that I’ll have to wait to move off until my yearly archive day. Speaking of which, is that day going to become the bane of my existence? I haven’t created a plan for that yet, which I need to if I want to keep my sanity. On the trust side, I’m trusting Google with the main chunk of my data. I’m not speaking to privacy here (cf. their Privacy policy, which has gotten some good press recently), I’m speaking about data replication. Essentially, I’m trusting their servers to keep my data safe from corruption and deletion. That seems to be pretty reasonable, but just to make sure, that yearly archiving should keep me as safe as possible.

Was this a perfect plan? Of course not. I need to tweak my file archiving through a managed plan, and I need to make sure my wife’s laptop gets backed up regularly. But all my daily, needed solutions have been taken care of, and then some.

Is this plan for you? It just might be, or at least a portion of it. I’d suggest asking yourself the following questions:

  • What are my digital needs?
  • What is my current digital strategy? (How am I using and backing up files?)
  • Where would I like to be in my digital life?

If you can answer those questions, get a good plan going, and implement it, you’ll be breathing a pretty big sigh of relief.

Trust me, it’s worth it!

Nate Humphries

Nate Humphries

Tech Editor at CultureMass
My two personal passions in life are technology and theology. If you sneaked a peek at my life you'd see me hanging out with my wife, our Dachshund Bella, and our snake Phoenix; playing Skyrim/Civ:BE/F3/FNV/BL/Rage/GW2/SRIV; watching movies; reading on my Kindle (sci-fi or theology research); or playing on my Moto 360/Samsung Galaxy Note II.
Nate Humphries
Nate Humphries

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