Progress update: My Dropbox to iCloud Drive experiment

To catch everyone up: A while ago, I wrote about paying for too many clouds that are getting too Venn-diagram-y for my comfort and wallet. Dropbox and iCloud are two of my most expensive and overlapping clouds, but I can leave Dropbox easier than iCloud, so I decided to try just that.

My plan is:

  • Phase 1: copy the roughly 70GB of stuff I have in Dropbox to iCloud Drive
  • Phase 1 part deux: backup the hell out of everything
  • Phase 2: test the hell out of changing my file-based workflows with iCloud Drive
  • Phase 3: Delete everything from Dropbox, except folders I’m collaborating on
  • Phase 4: fall back to Dropbox’s free tier for what little collaboration I still do with it, and to support the apps I use that sync only via Dropbox

Because of how much stuff I have, I’ve been paying $10 per month per service, so I hope to save $120/year.

If 70GB doesn’t sound like much to you, I have about 110GB of photos in iCloud Photo Library, and probably 1+ TB of purchased iTunes music and movies, and around 440 apps from over the years. But I generally don’t consider that stuff “data I need downloaded and backed up,” at least not in Dropbox or iCloud Drive. I have an external iTunes drive that I hook up once every few months, and I download my recent purchases ‘just in case.’ I also have a Time Capsule at home to which I backup my entire Mac, including both Dropbox and iCloud Drive, also just in case.

Part of the impetus for this experiment, beyond saving money and simplifying where I store stuff, is that I realized most of my collaboration now happens in Quip and task apps like Todoist, Trello, and Basecamp. In other words, I mostly collaborate in systems and apps these days, not raw files and folders. Being that I’m a much bigger fan of using various apps for most of my work, this fits my style. Obviously, your mileage may vary.

Status report

As of about September 23 or so, phases 1 and 1 part deux are done. I finished copying all my Dropbox files into iCloud Drive, then ran a Time Machine backup to cover my ass. Then another, mostly because I’m human and I still don’t trust these things. Also, no, I’m not blind or deaf to the, shall we call it, “ever so slightly turbulent road” iCloud has taken to get where it is today.

I am also what I would consider a pretty good way through phase 2—testing iCloud Drive for my day-to-day needs. I’m mostly iOS these days, so when I do things like scan travel receipts into a PDF for expenses, I now save to a folder in iCloud Drive. On my Mac, I moved the Dropbox item in the Finder sidebar down, and put iCloud Drive in its place.

So far, it’s gone pretty well. Saving and accessing files in iCloud Drive feels about as fast as Dropbox. Watching the file upload/sync process to iCloud Drive feels fine too.

Of course, one major feature iCloud Drive lacks for my needs is collaboration—it can’t share folders or even individual files with others (sure, MailDrop is a smart feature that might suffice in some cases, but.. eh, it’s just not the same). Being that my content strategy business is client-based, it’s a prime argument for why I still should keep around at least a free Dropbox account for the near future. I also have a handful of apps that still sync only via Dropbox, so I hope the free tier accommodates them too. Gradually, I’ll ask those devs to support iCloud Drive (if they don’t already), and possibly seek out alternatives that do. But if the free Dropbox space works for now, it isn’t a high priority, at least not just yet.

Naturally, I hope Apple is working on addressing these collaboration features which pretty much feel like a necessity these days. Considering it already has features like calendar sharing and a whole feature umbrella called Family Sharing, I think Apple gets it. I just want to see it move faster; it’s already way behind here.

I feel pretty good about moving ahead with phase 3 and 4, so I might take care of that this weekend. I’ll write a follow-up once the dust settles.