Using Dropbox to improve my backup strategy and file management

Combining physical and cloud storage

Every backup solution always starts with personal drama. You are working on this important project, you are already struggling to meet its deadline and, of course, you overlook how all your effort is being saved. These days my apps are already taking care about my documents, saving them somewhere far away. Simplenote, iA Writer and even the old TextEdit have some type of cloud integration, meaning my work is kept safe elsewhere. I also have a dedicated external drive with Time Machine, which I sync regularly to ensure all my preferences and desktop organisation is maintained, should the worst happen.

And then it happens. Returning from a holiday I realise how my MacBook Air has spent all the week sleeping on that power nap mode. It feels sluggish and clunky. Not having upgraded yet to Mavericks, I run a quick Mac App Store update to be told my machine's SSDs are in bad shape — apparently Apple shipped MacBook Airs with dodgy drives. Without a working laptop, at least I have a Time Machine copy and pretty much every document from work on a USB flash drive. The Time Machine drive will only work with the Mac it's backing up, so that's out of the picture. As I try to work using the USB flash drive contents, it decides to give up and pass to a better life.

Rethinking your habits: the backstory

In summary: one laptop down, one flash drive dead and 1TB of Time Machine that will only restore to its original machine. All of the sudden, my simplistic workflow is broken. My backup strategy chain is missing not one, but three key links. Knowing my documents will be waiting for me at work on Monday, I cannot be bothered to start to work on new ones from scratch. There's nothing I can do over the weekend other than draft a new backup strategy. What I need a reliable way to transfer files from work to home and vice versa. Ideally, I'd like to have both physical and digital backup copies updated without the least effort.

Note from the writer: I'm just sharing what I've come up with, with all its redundancies that might inspire others. This is far from a master class on how to tweak your setup. I'm also hoping some kind reader will spot things I'm missing and complete the puzzle for me!

At this point I can imagine your face shocked about my silly errors and workarounds. I'm not alone. It turns out a lot of teachers face the same situation: school IT departments aren't too keen on allowing staff to take stuff home but every teacher in the department does. Even if the shared drive on the school network was accessible from home, most teachers would continue using the USB drives to work on their lessons during the weekend. Others try to email files to themselves but Microsoft Exchange webmail and large attachments aren't very good friends.

After some thinking and testing I managed to create a foolproof backup and file management system with a minimal budget. All you need is:

  1. A proper USB flash drive (£13 from Amazon)
  2. A free Dropbox account
  3. A copy of Quicksand for Mac (donation)
  4. A Time Machine external drive (how to get started)

A proper USB flash drive

As surprising as it may sound, I want to keep a flash drive to transfer files between my PC at work and my laptop at home. It sounds low-tech, but I still feel the flash drive should be in the mix because it saves a lot of trouble. Having a physical object when you have to change classroom without notice, plug it in a PC and be able to start the lesson without logins is priceless.

The bad part is that flash drives fail. They also tend to be forgotten in classrooms full of children or worse, at the staff room! The easiest solution is to get one from a proper brand that already comes with encryption stuff, password and its own cloud sync.


I went for this SanDisk, which is still quite cheap (LaCie is also one of my favourites). It comes with USB 3.0 support and the gimmicks I wanted. Even if this model cannot take the beating of everyday use, I plan to renew it every six months: this is to ensure I have a new drive less prone to failure but also keep an old copy at home — you'd be surprised to see how much of those lessons are recycled year after year.

Next time I lose or break the flash drive I'll be relieved knowing the content is password-protected and the stored on the clunky website from the manufacturer. But of course, a flash drive alone is not going to fix my problem.

A free Dropbox account

If you've managed to read this far without skipping you'll be asking yourself about Dropbox. You see, IT overlords aren't too keen on that either. There's a lot of pupil sensitive stuff and data protection policies. What I'll do is to create a Dropbox account for PowerPoint presentations and Word documents without any private data — just lessons and assignments to print.

Adding a cloud element will make my files available everywhere, which will be a great emergency option if:

  • I forget to transfer a copy of the latest document to my flash drive.

  • I happen to lose, break or forget my flash drive at home or work.

  • I accidentally delete the file I was working on.

Uploading documents to Dropbox will allow me to access files from work and home without relying on emailing things to myself or looking for the flash drive in my bag. The main drawback — and this is a big one — is to remember to upload the most recent files to Dropbox.

Quicksand automation

Here's where everything finally comes together. I already have a flash drive that takes care of itself and a cloud storage folder to put my documents to access them everywhere. If I cannot remember to drag and drop tomorrow's lesson to an external drive, how am I even going to keep Dropbox up to date?

Fortunately there's a young developer who has thought about that. Sebastian Hallum Clarke of Zibity has built a piece of software that will sync your 50 most recently opened files with your online storage of choice. Quicksand can sync every 30 seconds the files you save on your desktop of documents folder, for example, ignoring things you don't need to backup such as music or videos.

I have been using Quicksand for a couple of weeks just to make sure it works as intended. It does. My only nitpick is that if you delete a file from your Mac; Quicksand will mirror this behaviour and delete it on Dropbox. This is not a massive issue because you can always access the Dropbox web interface and restore deleted items; it makes you a bit nervous when you don't realise what's really happening though.

Both Dropbox and Quicksand run as a login items and take up one slot on the menubar — a small sacrifice in exchange for the peace of mind. Originally this bothered me a lot but I managed to get used to it. The thing is that when you see the icons up and running you know everything should be working as intended.

A great start

As I continue to use this system I hope to find other improvements I might have overlooked. Overall I'm quite happy of what I've accomplished, because it all started with pen and paper drawing something similar to the sketches that illustrate this post.

I must admit that I should have read more about the topic before even designing my own backup strategy. Even when I was writing this I feared I would look stupid having missed some key detail. Well, this is what I came up with and is here exactly as I imagined it and implemented. I would be very happy if this helps you to organise your digital files better and would more most grateful if you cared to tweet @appfreak with suggestions. I promise get in touch and try.