Progress Out Of Digital Photo Organizing Hell

From the comments, tweets, and emails I got on yesterday’s post My Travels In Digital Photo Organizing Hell it appears I have a common problem. Basically, the existing photo approaches – in general – have created a massive mess. Apple and Google have just made this worse by continuously changing their underlying tools and approaches.

Buried deep in the comments was one from Darla DeMorrow. And it’s a gem.

“Hey, Brad. You’ve got a better handle on this situation than the average bear, but it’s still tricky, no matter what platform you use. And guaranteed it will change tomorrow, which makes us all crazy. But I’ve found a solution that I can recommend to my clients, who depend on professionals like me to keep them sane. Check out It’s a cloud-enabled service (not cloud-based) that allows you to organize in your own space, sync across devices, and only store in their cloud if you want to. It’s platform independent, sort of like the Evernote of photo organizing. You can throw stuff in the photo pile (making you happy), and it will automatically organize, to a point, making Amy happy. I’m happy to talk with you if you want to know more. You can find me online.”

I’ve been playing with Mylio for about 90 minutes on my Mac and iPhone. So far it is amazing – basically what I was looking for when I started this journey.

All my photos are still in Dropbox. I can access them, move them around, edit them, do whatever I want from a beautiful UX. Amy will be able to run this app on her Mac independently but see the same photo store and do whatever she wants. There are numerous backup options that preserve the directory structure and do NOT force me to use the cloud. I can sync with all my devices seamlessly. It knows how to import stuff like my Facebook photos, Aperture, and iPhoto. It works with Lightroom. It’s extremely fast.

It’s not free but I’m happy to pay for something that actually works. Thanks Darla!

  • jamesoliverjr


  • Yessss

  • I’d love to know how you’re getting on… I just went through this this past weekend as well. Amazing timing. I have 80,000 photos to walk through… All on Dropbox right now.

  • Oh my goodness! Thank you for posting this. I have been in the same awful spot for waaaaay too long. As a scrapbooker, traveler, mom of 3, then mom blogger and now wine writer and startup entrepreneur, I have a LOT of photos and am in need off help. Can’t wait to check this out!

    • Darla DeMorrow

      Amy, I’m in the same place. As a mom, organizer and designer, and blogger, I have more pictures than I really want to care for. But now they are all in one place, and accessible all the time. As I have time to go and delete some that I don’t need, the deletes propagate into all my other devices when I open them all up to sync back through Mylio. What a sanity saver. It’s pretty cool.

  • Try migrating from Dropbox (or Google or Box) to any other service with complex media files that have licensed assets inside.

    Pure hell.

    • That is a version of hell I don’t look forward to.

      • No kidding. Adobe – wants to update and break back compatibility, Dropbox mangles files, and Google gives false positives on “is a file done syncing.”

  • Jennifer Lee Kirk

    You should give SmugMug a try. You can easy move photos from Picassa and/or uploading from Dropbox directly. If you do all of the uploading in one batch, the system will watch duplicates by filename. Its also very easy to organize thanks to keyword/tags you create and search their image archive. Plus you have control over how to share and protect your images – passwords, watermarks, what guest email address is able to access an image, etc.

    I was introduced to them by my good friend who is a popular pro photographer (and full disclosure I *just* started working for them 2 weeks ago, but I wouldn’t have done it if I wasn’t impressed by their services for my own use too) and sings their praises to high heaven. My dad just signed up over Christmas too – they are having a 40% off promotion. You should check them out. Happy to answer any questions/help you troubleshoot more issues you are looking to solve!

    • I’m all in on Mylio at this point. I’ve been using it for 24 hours and it’s amazing and just what I was looking for when I started this walk down photo hell.

  • Here’s something new from AWS for $12/year (just discovered it, so I don’t know if it’s any good):

    • Just looked. That’s going to be a whole lot of no fun as it’s just uploading everything from the desktop to the cloud. Maybe as a backup solution so there’s another backup besides the Dropbox and multiple computer backup, but I feel like just having a backup harddrive in a safe that is periodically refreshed is a better answer.

  • Mylio looks cool! I’ve been collecting digital photos for about 15 years and have a pretty decent collection that I’ve fairly ruthlessly organised into folders. I’ve tried Google Photos, Picasa, etc but in the end decided I didn’t like all of them mostly because of the struggles you’ve had with them.

    Does Mylio do anything about consistency checking between your libraries across devices?

    A few years back I decided that my photo collection was the only digital data I really cared about and couldn’t afford to lose and started thinking about backups and their integrity.

    I’ve been working on a tool on and off for a few years to try to address this issue – it’s less of an organising tool and more of an integrity tool that allows you to ensure each of your backups is actually what you think it is.

    Since I’ve started using it, there’s been three separate occasions where I’ve discovered corrupted photos due to bitrot on various drives. Almost certainly would never have noticed and might’ve ended up with more bad images as the drives failed harder over time.

    While it started just as a simple tool to verify backups it was pretty trivial to add duplicate detection (both exact & perceptual hash based) which has been useful for saving space.

    I’ve been tempted to try to get it to the point where it’s useful for other people but so many people seem to use cloud services like Dropbox now and are totally happy to trust and rely on their service to maintain their collections. Not sure how many people are panicky enough about their photo collection any more to justify any more effort on it though!

  • Matthew Zeiler

    Hey Brad, if you want an easy way on your phone to find your photos using the latest AI, give Forevery a shot: You can even teach it things like the name of your family, friends, pet, etc. and it’ll auto-tag them going forward. Let us know what you think!

    • Yes, would love to hear what you think about Forvery Brad. It auto organizes your photos based on what it recognizes inside of them – people, things, place, emotions, etc.

      • I’m liking it in general (per my note above). It does a good job with the auto-organizing, but it still feels very limited across everything. It’s fine on my phone, but not doing much else.

        • Thanks for the feedback Brad. Lots of people have asked for integration with Dropbox and others. We are looking at that now. Have also received a few requests for a desktop version. I’ll keep you updated as we evolve.

    • I downloaded it shortly after Fred Wilson sent out a note about it. I like it, but it’s not the total answer across 22k photos.

  • I tried something similar called Shoebox. Free unlimited image storage/backup with easy to use navigation. Like a Dropbox for images. I ended up quitting because the backup size in the free plan was not the original image size (plus, it didn’t have the search functionality I wanted).

    I’m willing to give Mylio a demo but there are some big questions left unanswered on their website. Any monthly upload/download bandwith restrictions? Do my Mylio edits get synced back to Lightroom and my original file? And, if they’re just syncing copies of my images, how much storage do I get in the cloud if I want all my images off my laptop? What about sharing on social and embedding image links in blog posts? I guess I’ll just have to give it a whirl 🙂

  • Reading the Mylio site, I felt a surge of hope. Then just as quickly as I saw Mylio as the salvation to my epic photo problems; I felt a pang of anxiety that this service would get bought by Google and get messed up and shut down. Nervously dipping my toe into these waters.

    • Darla DeMorrow

      Yoav, the best thing about Mylio is that YOU always keep your photos. So if Mylio goes under or, as you pointed out, more likely gets bought, all of the organization that you already created on your photos stays with your photos on your drives and devices. You wouldn’t lose anything except future sync capabilities if you decide to stop using it. This is a win for us finally being back in control of our own data. Let me know what you think of it.

  • Ryan S.

    Brad, now that you’ve had five days with Mylio anything you learned about how to manage your photos? Did you watch existing folders or fully move them into Mylio and let it manage everything (still on the file system)? I have a Sinology NAS that I’ve added for original storage and decided to let Mylio manage everything since having watched folders to a NAS isn’t wise (and Mylio thoughtfully doesn’t support it)…plus it seems like the most commonly supported scenario so is probably the simplest to ensure always works long term.

    • Long post coming tomorrow as I accidentally deleted all my photos today (fortunately, I had a backup, and Dropbox also did a perfect job of Restoring the deleted photos.)

      Other than me misconfiguring Mylio (in conjunction with Dropbox), I love it. They need to spend some time figuring out how to message “this is what you should do if you have things on Dropbox.” The issue was with Watch Folder, and it didn’t occur to me how a cascading delete (when I misconfigured a new machine) would roll through everything.

      I’m in the midst of having Dropbox restore everything. Then I’ll try again.

  • Joseph Kolchinsky

    Brad – have you heard of EverPresent?

    We’ve used them extensively now with our technology management clients – we wrote about them and their founder, Eric Niloff, on our site (

    They use Mylio to manage your photo library for you, getting to know you and your family, and providing a framework in which your photos can be organized from the perspective of sharing and retrieving them easily over the long-term. They’re excellent for vacations – before you get back they’ll have all your photos sorted and edited – ready for you to enjoy or share.

    Let me know if you’d like an introduction – we know them well.

    • I don’t know them – sounds like good folks. I don’t think I need an intro, but will holler in the future if I want one.