From Dropbox to iCloud Drive: An Unexpected Experiment

A while ago, I realized I’m going through death by 1,000 clouds. I pay for too many cloud services, many of them redundant, and I’d like to find a way both to simplify and to go easier on my wallet.

I’ve cut back on a service here and there, but now I’m trying an experiment: copying all my files from Dropbox to iCloud Drive, and downgrading Dropbox to a free account. My goals are:

  • Simplify where I keep most of my files
  • Keep a free Dropbox account (for now) so I can still get and share files
  • Pay for only one cloud locker and save around $100 per year

iCloud Drive and Dropbox are two of my most expensive clouds which have the most overlap. However, I’m pretty embedded in Apple’s ecosystem and generally happy—a large part being iCloud Photo Library—while Dropbox is more of a generic, replaceable cloud locker. In other words: between the two, I can leave Dropbox easier than iCloud.

As I write this, I’m uploading just over 100GB from my Dropbox to iCloud Drive (my screenshot shows only 45GB because I don’t need the rest readily available; I can finish uploading it later in a separate batch). Since I’m beta testing macOS Sierra and iOS 10, I went all the way and switched on the new iCloud feature that syncs my local Desktop and Documents folders with iCloud, too.

Now, Apple’s cloud has become much more reliable for me in the past couple years, but I won’t put all my chickens in one basket, not for a while. I use a Time Capsule at home to backup my entire Mac, including my cloud directories. I’m also considering firing up one of my other previous backup drives because, let’s face it—you can never have too many backups.

I’ll keep my free Dropbox account mostly because I still collaborate with clients and on various projects. But my hope is that the free 2GB, plus whatever extra free space I’ve earned over the years, will be enough.

Who knows, maybe this will work, maybe it won’t. If it does, I’ll gain some simplicity and save a little extra cash each year. To me, that is at least worth taking a shot.