The Way I Work With Paper, Documents & Photos: iCloud Vs Dropbox

Ever since reading the Paperless book by David Sparks last year, I have been on a path to becoming entirely paperless within my own workflows. And the final push for me was the decluttering course I started in January. While cleaning out all of the cupboards in my office, I realised how many junk pieces of paper I had accumulated over the years and how at the same time, if I needed to find an important document urgently to prevent missing a deadline, I'd never be able to find it in time.

I purchased a Fujitsu Scansnap S1300i and a shredder and got started with the mountains of paper. Anything that didn't need to be scanned got shredded and anything of importance (major or minor) got scanned. Following the advice of David in the Paperless book, I created an Action folder in the Documents directory of my MacBook Pro and made sure every scan got sent to that folder.

Just like with organising my emails, it took some time to get every document scanned and appropriately labelled. I followed the standard of yyyy-mm-dd - company - document for every document. For example, 2015-04-12 - barclays - appsolute pixels accounts for march-april.pdf. The critical format is .pdf because of its ease of use and popularity amongst any application. Moreover, the Fujitsu scanner does Optical Character Recognition on each PDF so it's extremely easy to not only locate a file, but to locate text within a file.

I am a folder guy by nature; everything I do involves folders and subsets of folders. It's the only way my brain operates. So I created a hierarchy of folders within my Documents structure on my MacBook Pro. For example:

  • Documents
    * Documents
          * Personal
                * Finances
                      * Receipts
    * Personal Projects

The receipts folder contained all of the receipts I have accumulated over the years in paper and through emails. The Paperless book has an important guide with how to save an email as a PDF quickly. And that is an important feature I require when looking for an email application for iOS so I can maintain Inbox Zero and triage on the move.

After a few weeks, I had scanned every file I needed to keep and shredded every file I didn't. Each file was labelled appropriately and my documents were now completely organised. I now needed a location to have them stored so that I could easily access them anywhere.

iCloud Vs Dropbox for Documents

I had been utilising iCloud payments for quite a few months to backup my iPhone and iPad with the 200Gb plan for £2.49 per month. At the same time, I was also paying £9.99 per month for Dropbox because when I signed up a few years ago, I thought I'd need the 1Tb storage eventually. At this stage, I had never used more than 1.3% of the 1Tb.

The decluttering course made me realise the mistake of paying for services I did not require, so Dropbox was the first to go. I still needed iCloud because of the backing up of my iOS devices so I decided to go all in with iCloud Drive.

iCloud Drive works in a slightly different way to Dropbox; each application that uses iCloud has its own application folder and your documents for that application are stored in the folder for that application. You can also just create folders of your own. I copied my Documents folder across to iCloud Drive and to the Documents 5 by Readle (henceforth DBR) folder. So my structure was:

  • iCloud Drive
    • Documents
      • Documents
        • Personal

You get the idea. This was efficient because I could use the iCloud Drive app on iOS or the DBR app and be able to access my files anywhere. The best part about this set up was the two-way sync with the DBR app. I could access a PDF stored in iCloud Drive within this app, sign it and within seconds, that change had synced across to iCloud Drive on my Mac and iPad. It also worked in the reverse direction. If I wanted to use Dropbox with DBR, I would have to download the file, annotate it and then re-upload it to the Dropbox folder, replacing the original. This was a bonus point for iCloud Drive.

Because PDF Expert is an application made by Readdle as well, they have brought PDF annotating capabilities to DBR just by having PDF Expert installed on the device. Using DBR was also extremely helpful for reading through a Swift development book. I would start a chapter on my iPad, highlight passages and examples and have those synced across instantly. I could then follow the highlighted examples in Xcode when I returned to the MacBook.

For a few months, I had a solution that worked really well with my documents and iCloud Drive. I could access any important document from anywhere and send it on as an email or share it appropriately if required. This access has saved me a few times, including when a hotel in Greece couldn't find my booking; I accessed iCloud Drive through the DBR app and pulled up my reservation as a PDF. That prevented a frustrating start to the trip.


iCloud Drive had been working really well for me with documents. With the introduction of the and iCloud Photo Library, iCloud had the potential to solve another problem: photo management. With a Mac Mini connected to a Drobo (external hard drive), I placed my Photos library onto the Drobo and added in thousands of photos separated per album. I have added in my entire wedding collection of photographs, and all of the holidays I've been on with my wife over the last 6 years. The beautiful thing about this is the fact that this is always with me and I can access the pictures on any of my iOS devices. I have added in 37,000 photos without any issues and each photo and album has synchronised across to my iPhone and iPad.

Apple have done an excellent job with iCloud and it really solved some of the problems I've been facing.

A Few Remaining Problems Causing a Return to Dropbox

At this point, I had both photos and documents working well with iCloud. That is until I showed my wife our wedding holiday albums in my on my iPhone. Because we're signed into different iCloud accounts (because of contacts and calendars), I couldn't just give her access to the photos. And while I could create a shared folder, it is not realistic to create 71 shared folders and transfer 37,000 photos. I looked into Apple's Family Sharing but at the moment, it doesn't cover the feature I'd like here; one library shared amongst two iCloud accounts.

I have also received requests from family members to send the photos from the recent family weddings and combined holidays. This adds up to about 4,000 photos. There's no current way to do this from iCloud. With these issues, I began seeing a few shortcomings with iCloud: the lack of being able to share links out to an album or folder of important documents and the lack of sharing entire libraries amongst my family.

After a fair amount of pro & con planning between iCloud and Dropbox, I decided to sign up to the Dropbox Pro again for £7.99 per month. This is one service I'm paying for monthly, for the first month to see if it is a solution I can make work before I commit to an annual payment. After decluttering, I now only pay for services annually.

My list of Pros for Dropbox included the following:

  • Share entire marriage albums with my wife (by her signing into my Dropbox account)
  • Share albums with friends and families with the Dropbox link
  • Share a set of multiple documents with third-parties like an accountant
  • Revision history (I can change a file and have the older version accessible on the Dropbox website)
  • Two-way sync with the new version of Documents by Readdle which will be released by the end of April

The big point against Dropbox is that I am now paying for an extra service. iCloud Drive did a fantastic job of helping me manage my documents and photos. Dropbox also doesn't have any granular pricing. I could easily get away with just 300Gb of Dropbox Storage rather than paying for 1Tb.

Required iCloud Features

I have nothing against iCloud and it has worked really well for me. I would however love to see iCloud gaining a few features before I'm able to return to it full-time for documents and photos: Library and Link Sharing and Revision History. I would love for my wife to be able to share my iCloud Photo Library in its entirety and have every photo in the across her devices rather than having to navigate through my almost endless list of folders within the Dropbox app.

It would be so efficient to also have the ability to send a link to a specific iCloud album/folder and to be able to see changes across documents in iCloud Drive with a revision history. I'll pay for Dropbox for two months to see what Apple potentially announce at WWDC relating to iCloud. I have also come across Dropbox Project Infinite this morning which could be a game changer for using Dropbox with lots of files and just a small MacBook Pro hard drive of 256Gb.

I am continuing to pay for iCloud Drive (still 200Gb) which I am using for backing up my devices and because accessing iCloud Photo Library through the Apple TV is a beautiful thing. We've spent hours looking through our holiday photos over the past few weeks; something we never did even though each photo was in an album on my computer. And 37,000 photos is taking up about 110 Gb, leaving me with plenty of space in my iCloud Storage.

The next few months will be interesting. If Apple do not announce shared libraries, I could still solve that problem when my wife purchases a new iMac; we could easily add the entire library again to that computer and synchronise it using her iCloud account. But I would love for Apple to make this easier because I would much rather pay for one service. I'm also extremely happy with iCloud and its potential. I hope someone from Apple reads this.