Sharing Is (Still) Hard

My dad had a simple request. He just took a trip, and wants to share photos. Crazy, right? The 200 photos totaling 1.6GB was “too much for flickr”, so he wants to host off of a subdomain of No problem, just get me the photos.

The problems start. Me:

The simplest way to do that is to share a dropbox folder with me.

  1. Make a folder in your dropbox
  2. put the photos there
  3. Find the folder in, and share the link


OK, but how do I do that?

These interfaces are not obvious to most people. If you’re reading this, you’re probably in a bubble, doing things with technology that most people couldn’t. Keep in mind that this guy had a computer at work for 30 years. You don’t forecast the value of an oil field 50 years into the future with a slide rule.

He managed to create a Dropbox account and put his photos in it. Now I need to explain how to get them to me. I figured sending a shared folder invitation with instructions would help.


I just sent an invite to a shared folder. It has two images it in describing how to share a folder

Here they are, clear as a bell, right?

Step 1

Step 2


OK, I opened and “agreed” to share on your invite. Now, what?


Move your folder of photos into the one I sent.


It sounds simple … but, I do not know what to do.

Eventually, Dad:

Well, I am giving up on this thing I am putting selected photos on Flickr.

Instead of sharing 200 photos, he shared just a few. And it took hours to get to this point. Next time you make fun of someone working on “some photos startup”, step back and realize that most people could really use a better solution.

Sure, Instagram and Facebook are amazing… at sharing a one or two photos. One per day, if that. Anything more is still a pain in the ass. Add video into the mix, and it’s clear no one has a good solution for sharing a single video. They’ve chosen to cripple the video options in Vine & Instagram instead of solving the complexity.

Another lesson here is that it is hard to find a solution. If it were easy, Flickr, Instagram, Facebook, Twitter, Dropbox, or a hundred other contenders would have solved this problem already.

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