Sharing Is (Still) Hard

I understand your specific pain ;) I suppose a quick "hack" would be to allow creating "managed" accounts where you can easily have management access over a sub-section of family/friend accounts without knowing their password, etc. That doesn't solve the underlying problem, though.

Maybe there is room for a single-click-install desktop software app that simply takes the name/email of the destination contact for the arbitrary content and then crawls provider APIs to quickly determine how best to get the content to that person and orchestrates it using the APIs so that the end-user doesn't need to learn configuration screens and confusing (to them) UX.

What's wrong with uploading 200 photos to Flickr? Sharing 1.8GB of photos more than once on Dropbox (who deletes things like this?) means you need a paid Dropbox account. So even if this was in the Past when Flickr didn't have an "unlimited" free account, you'd still need to pay for something.

The only way I've found Flickr isn't good at sharing a large number of photos if you want/expect some people to have high res versions of all or a large percentage of those photos on their computer so they could print them offline or something.

Still an unsolved problem there, but if all you were going to do was "host them on a hostname", I'm not how Flickr doesn't address the need very well.

I bet he wouldn't have had any problems emailing that folder to you. I know when I need to send a few documents or photos, I without even thinking try to do it via email, only to be met with messages of exceeding size limits.

Is there a service that ties both the action of emailing with the process of syncing via dropbox? If not, I could see it being incredibly useful for people like your dad, and mine. An app whereby you go through all the same motions of creating a new email, attaching a few documents/folders, and in the background those attachments are being synced to some dropbox folder.

Of course, email services could expand their size limits, but I'm sure there's a reason why they're not.

I agree that Dropbox is not very good at sharing photos. The solution really has to start much earlier in the tool chain, ideally with the camera itself, or the tool that downloads them. Smart phones are great with this, since you see share options right after snapping a photo. iPhoto also has fairly decent sharing options (resizes images, creates web albums, etc). But once you're outside of the realm of camera and photo apps and working with general purpose tools like Dropbox, it gets a lot more difficult.

I've worked with users that are anywhere from 15 to 85. You've hit on a lot of key issues. Sometimes they ask questions like "What's a browser?" and then you have to remind yourself that the average middle America user is so far from the demands of a silicon valley user.

Disclaimer: We make a solution in this space. http://eversnapapp.com

I'm curious to get your thoughts on it. Well written piece.

What is wrong with FTP? Or scp if you prefer?

scp -r pictures dad@my.son.computer.org:~/pictures

Oh right: this would go directly from your dad's computer to hour own computer, encrypted, without passing by the NSA case and without your dad's pictures scanned for terrorism.

I came to this conclusion as well when my Dad was looking for a way to share travel photos.

Another issue: I imagine it would take a lot of time for the Dropbox client to sync 1.6GB of data, even for people with fast Internet connections.

true fact: I didn't share the images in this blog post correctly the first time. I used the Dropbox links from the shared folder view, not the shared link view. It's obvious what I put it that way, right?