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Stop the ride, I want to get off

Posted in Design and Tools

I never thought I’d see the day, but Daring Fireball’s take on the latest Dropbox announcement is exactly how I feel about it.

If iCloud Drive folder sharing works as well as promised when it ships this fall, I’ll probably ditch Dropbox completely.

Dropbox is getting messier and messier as time goes by. I wondered what was going on when they announced their rebrand a couple of years ago and things haven’t gotten any better since. In fact, I went to find that link to their rebrand article and went to their blog first, before realising it had been posted on Medium. I had no idea what was going on…

  • Why is it called ‘Work in progress’ rather than ‘Blog’? Is this some kind of landing page?
  • What do I click/tap? There are no affordances; no underlines, not even any colour or typeface weight differentiation on links. There are some ‘ghost’ buttons though…
  • There’s so much animation and movement that I have no idea what to concentrate on
  • Why does my cursor turn into the word ‘Read’ when I hover over an image? Is that present or past tense?
  • It’s an interesting layout, but it detracts from the content, rather than presenting it clearly
  • Are any posts in chronological order? It jumps from what seems like a hero post at the top to some against a white background, then a bunch of ‘Featured Topic’ and ‘Featured Collection’ posts. Then three more Featured Topic groups for good measure
  • Why is the subscribe link in the footer (that provides no indication that it’s a link beyond a hand/pointer cursor on hover) a moving target?

It seems to me symptomatic of a company that has no idea what it is anymore.

Part of Dropbox’s genius was its simplicity, and Steve Jobs’ assertion that Dropbox was a feature seems more accurate as time passes and they add more features on top of their (admittedly amazing) original ‘feature’. Those features feel ill-informed, unnecessary and detract from what Dropbox actually is.

I’m a big fan of the ‘do one thing well’ approach to pretty much anything. Dropbox have lost that focus.

Even that one thing isn’t working as well as it should: it’s hogging system resources where it should be quietly and efficiently working away in the background.

Dropbox’s new features

I’ll admit, at first glance I quite liked one of Dropbox’s new features: Shortcuts. The idea that what are currently browser bookmarks could become part of my file system seemed clever. Until I properly thought about it. Being able to have clients’ Trello boards could live alongside their user journey diagrams, UI mockups and icon source files would be convenient, but I use the Trello app so the ‘shortcuts’ would bypass the app and open in my browser, which would be annoying to navigate back to while working. For me, apps are where work should happen, not the browser.

And the rest of the new features, like Slack and Zoom integration, seem completely pointless. Zoom integration in particular looks like even more of a mistake in light of their recent security issue.


Eight years ago, I wrote about why Dropbox was my most useful app. Back then syncing files was relatively novel, and Dropbox did it best: it kept everything in sync and gave me an easy way to share files with clients and other people I was working on a project with. I happily paid for it each month.

Come 2017, I downgraded to the free version. I had unlocked plenty of free space through referrals when I first started using it so I had more than enough to cover syncing a handful of apps and storing client work so it was easy to share files and folders when necessary. Where did I put the rest of my files? iCloud Drive.

Moving to iCloud

Back when I wrote that article about Dropbox and how useful it was to me, iCloud had only been around for about six months and was very much an MVP. iCloud Drive was announced in 2014,but it wasn’t until late 2016 that it became a serious Dropbox alternative.

Apple and privacy

Apple make a big deal about privacy. Their business model isn’t centred on selling their users’ information to marketers, it’s mainly about their users buying their not-inexpensive products. I trust Apple more than any other company with my data.

iCloud Drive is a space saver

iCloud Drive did most things Dropbox offered, but there was one thing that it did better. In the same way that Photos does, it promised to free up hard drive space by clearing files I didn’t use very often from my machine. They’d still be visible in my Finder but it would only download what I need when I need it.

That last bit was key. Dropbox has Selective Sync where you manually select folders that won’t be pulled down to your machine, a bit like archiving them. The problem was, the non-synced folders aren’t shown in Finder, so I’d forget they existed! On the odd occasion when I needed one of those files it was nowhere to be seen so, thinking I’d lost them, I sometimes found myself doing extra work to redraw a diagram or asking a client to re-send their logo files.

I think Dropbox now offer auto-clearing of files on the paid plan, but there’s another issue on that front: cost.

iCloud is cheaper than Dropbox

In 2017 I moved from full-time freelance to full-time employment. I kept a handful of clients on my books, but my overall income from freelance was much reduced, so I began to look for ways to keep operating costs down to maximise the income I did make from working evenings/weekends.

Dropbox’s lowest paid tier offers a whopping 1TB of storage on a rolling £9.99 per month. I’d never come close to that in all my years of paying for Dropbox and I had always wondered why they didn’t offer less storage for less cost. iCloud offers an ample 200GB of storage for just £2.49 per month; I was already paying 79p for 50GB so the £1.70 jump was trivial.

Downsizing my business was a big motivator for this shift, but even if I was still full-time I’d’ve made this move eventually.

Family Sharing

Another good thing about iCloud is that it offers Family Sharing, where you can share your storage allowance between the other members of your family. Once I start hitting up against that 200GB limit I’ll be able to upgrade, share the 1TB with my wife and cancel her individual storage plan.

Kind on my battery

Finally, I’m very happy that iCloud shows absolutely none of the signs of being a hog on my system resources in the same way Dropbox does. If I could remove the Dropbox app from my Mac my battery would last longer.

Digging its heels in

I’d’ve ditched Dropbox altogether back in 2017 but a few things have kept me hanging on in there.

One daft thing I’d really miss

I’ll start with the relatively trivial: without Dropbox I’d have no idea if I was online or not! I’ve always relied on Dropbox’s menu bar icon as a quick way of knowing if I have an internet connection or not.

The wi-fi icon tells me if I’m connected to a wi-fi network, but that doesn’t necessarily mean there’s an internet connection beyond that. When I’m not connected, the Dropbox icon is greyed-out, so I know to restart my modem, look for a better wi-fi network, or tether to my phone. Without Dropbox, I’ll be in the dark.

The convenience of sending large files

One thing Dropbox is excellent for was giving every file its own URL that can be sent over email. The recipient just follows the link and downloads the file. I’ve used that a lot over the years – I’d be working out of a folder in Dropbox anyway so when I was ready to share some work I’d just right click and click ‘Copy Dropbox Link’. Easy.

But I’m thinking back to the last time used it and struggling. I send most files, large or small, in Slack, Trello or a tool like that. The odd time where email is the only way I can send something, I use Apple’s Mail Drop, where attachments are stored in iCloud for 30 days instead of being sent over email.

If I really need to send a link it’s possible with iCloud as long as the recipient has an Apple ID. If they don’t, that’s where Dropbox comes in. Though if Dropbox weren’t running on my Mac I’d be able to use its web interface or a similar tool like WeTransfer, so this feature isn’t something I couldn’t work around.

Syncing for apps

Most apps that have shared configuration or info that syncs between devices offer syncing via iCloud or Dropbox. Over the years, I’ve moved all of this over to iCloud, bar one app: 1Password.

I use 1Password’s iCloud syncing for my ‘Primary’ vault, but my other vaults are synced via Dropbox. It’s possible to store a 1Password vault in a normal folder on the Mac app but not on iOS. This is the biggie, really.

Even if the iOS app had the ability to sync over a regular folder via the Files app, I have a couple of vaults that I share with other people. Those vaults would have to wait for Folder Syncing to arrive in iCloud Drive this autumn, but it’s all moot until 1Password add the feature.

One big barrier

The negatives of using Dropbox are now outweighing the positives. It’s not costing me anything financially, but it’s something I’d like to do without entirely. 1Password’s reliance on it for vault syncing means I’m stuck with it until:

  • 1Password add ‘Folder’ as a syncing mechanism for their iOS app
  • 1Password allow for more than one vault to be synced via regular iCloud
  • I move to a different password management service

Perhaps it’s not mission critical that I see those vaults on iOS; maybe they’re fine just on my Mac, so Catalina’s Folder Syncing would solve the problem.

Dropbox are adding features in a desperate attempt to justify their existence, pushing their users away while forgetting that their first amazing ‘feature’ and clear message was why everyone fell in love with them in the first place. Stop the ride, I want to get off!

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