A super simple, ridiculously easy way to keep your images organized! (video!)

Image  organization is one of those snoozefest topics that kind of makes you feel like you just took a Benedryl and can't keep your eyes open. But despite the dry nature of the subject, it is probably one of the most important things for any photographer (business owner or not) to nail down as soon as humanly possible when you start taking photos on a regular basis. 


When I first started practicing taking photos and experimenting with edits etc…my images were literally all over the place. I had NO clue what I was doing or how to properly organize my photos in a way that wouldn't make me want to pull my hair out. I was loosing things all the time and spending way too much time trying to nail down where a particular image was when I needed it. 

I knew I needed help and I knew I had to get this under control. 

I checked out the internet to see what other people were doing and took bits and pieces from lots of different workflows and strategies and made my own system that I knew would work for me. 

This is one of those things that will probably be slightly different for everyone based on what you shoot, how often you shoot and how your brain works with regard to organization. This works for me and I hope you can take a look and get inspired or use some of my ideas about organization to get your own images organized in order to save your hair from getting pulled out. 

Sort by date

The easiest way for me to think of systems is first by dates. My brain can remember timelines pretty well and I usually have a good sense of when things took place and so it only made sense for me to start with dates as a base for my organization. Some people like to use topic as a base and I think that makes sense as well, it just isn't the direction I decided to go. 

I start everything this exact way:  Year/Month/Day/Session

This way, if I'm looking for an image that was from Trevor and Mary's session, I know that I shot them around April or May of 2015 and so I can easily navigate to that folder and find what I'm looking for. 

In each session folder I house all of the RAW images from that session. I import them into Lightroom from this folder. (This way LR is using my organization system instead of me using theirs). Once all of the RAW images are in this folder, I back it up onto another external hard drive. 

Consistent System

Once I am done editing the session in Lightroom I need a system for the final images. I will likely have images for:

  • The client
  • The blog post
  • Social Media (facebook and instagram) 


I export images out of Lightroom into that same folder as the RAW images and I put them in a subfolder called 1-Client. These are full size, high resolution images that I will then upload into Shootproof for client delivery


Images for the blog are typically images chosen from my final set of images for the client that I put into blogstomp. Blogstomp will resize the images and I can put two verticals together for my preferred blogging style. Since blogstomp is resizing the images, I simply use the client images and copy them into BS and then once they are stomped, I put them into that same Session folder in a subfolder called 2-Blog. I can upload them to Squarespace for the blog post from there. 

Social Media

For SM, I do something slightly different. Since I am on the go quite often and also like to use my laptop, my desktop and my phone to access images, I have a folder in my Dropbox that houses any images that I might want to use on social media. I want them to be smaller in file size since I don’t need huge images for social media posting purposes. 

So in my Dropbox, I have a folder called "Social Media" that has the same organization as my hard drive. Year/Month/Day/Session. 


Then I simply export the entire session from Lightroom at low "quality" (60%), long edge 1024 and 72ppi into the folder on Dropbox. That way I will essentially always have every image available to me if I want to post it on IG or FB etc..and I don’t have to wait until I'm back at my desktop in order to find it and get it posted. 

This system works so well for me. Everything is easy to find and I have access at any time to most any images that I would need. I will caveat that to say that I do have 1 terabyte of storage on my Dropbox, but I haven't come anywhere close to using that much space yet in that place. 


Once everything has been exported and is in its correct spot, I backup the folders to my other external hard drive. This way I have images on two hard drives, in Shootproof and in Dropbox. 

Backing up your images is of utmost importance because all of this technology will eventually fail. Having things in multiple spots is just good business. Although I'm happy with my current backup plan, I think it could be even better and its something I'm considering revisiting in the near future! 

If you are more visual and would like to see a video of my whole organization system, just click below!

9-5 does not = Failure

It's ok to have a 9-5 job, I promise. 

I'm departing slightly from my usual nerdy teaching posts to talk about something that I've seen happening in our community. Granted, we all run in different circles and so you may not be as aware of this as I have been depending on your current "circle", but if you spend any amount of time hanging out where other small creative and online business owners hang out, you might have noticed it too. 

Your "dream" isn't really a dream unless you ditch the 9-5. 

And I'm here to tell you friends....that's a big fat lie. 

Its ok to have a 9-5 job | Entrepreneur Life | Cinnamon Wolfe Photography

Somehow we've all bought into this notion that life isn't life and we can't enjoy it and live out our dream if we are handcuffed by a 9-5 job. Where in the world did this come from??? Wasn't the dream from a while back to actually HAVE a job that would allow you to support yourself and your family? 

Now, I'm not saying it's a bad thing if your goal is to quit your 9-5 job and support yourself 100% though your own business. What I AM saying is that it's not the ONLY thing.

And I feel like (to an extent) our creative community has forgotten this. 

Sure, there is beauty and something to be learned from those who give it a go and make it work (thanks Tim Gunn) in full time small business entrepreneurship. But there is also beauty and something to be learned from those who juggle two different gigs, or a gig and being a full time-mom or two full time gigs and being a mom (or dad!) 

Your story may look so incredibly different from their story, but that doesn't mean your story is wrong. 

Cinnamon Wolfe Photography | NJ Wedding Photography

Let me tell you a little bit of my own story....

For anyone who doesn't know the backstory on how I became a photographer...it kind of happened as a result of pure circumstance. I don't have stories of me carrying around a camera everywhere I went as a 5 year old. I didn't dream of being my own boss or capturing love stories while I was slaving away at a corporate job. 

I received a Master's Degree in Human Resources from the University of New Mexico in 2004. I worked my way up to what I would consider a fantastic job at T-Mobile as Human Resource Business Partner throughout the next 8 years. I taught a few classes at UNM and also at Bellevue College on Organizational Behavior and Performance Management. I loved what I did, I was good at it and I aspired to do more especially in the area of teaching. 

Then the Army moved us to California. To a tiny little town with no "big" HR jobs. It wouldn't really work for me to work remotely. I wasn't horribly depressed about this but I was a little trepedatious. What in the would I do now? 

Backing up a few years....I got my first pink Canon point and shoot digital camera when I was planning a trip to Japan in 2007. I loved that camera and enjoyed taking photos that focused on interesting compositions rather than just pointing and shooting. 

5 years later as I sat in a friends house in California, jobless, I looked at her new-ish DSLR camera sitting on her kitchen table and thought, "Hey I have all this time now, I should learn how all this photography stuff actually works!" 

And that was the start. That was the birth of Cinnamon Wolfe Photography. I devoured every resource available. I read and read and read and read some more. I got a Canon t3i and practiced all the time. I practiced on some friends and started thinking....I have a business background...is it that impossible to think I could actually turn this into something? 

And I did.

Or, I am?

I guess I will always be...turning it into something....since owning your own business never really slows down or stops. You need to continually grow. Continually learn. Continually deal with things that get thrown at you (moving your business across the country anyone?) 

Why do I tell you this story? Because sometimes (actually maybe a lot of the time?) I wish I could just go back to that cushy 9-5 job. 

Yes, I said that (well, wrote it if we are being technical) out loud. 

I know of someone who actually HID the fact that she had a 9-5 job from industry friends (FRIENDS!!!) because she didn't want to appear like she didn't have enough of her stuff together to be full-time fancy. 

I know that personally, I have struggled with feeling like if I ever have to go back and "get a job" that would mean I am an utter and total failure at life and everyone else around me would be "living their dreams" while I had to "go back to work." 

That literally makes my heart want to cry. 

There is NOTHING wrong with having a job that pays your bills. There is nothing wrong with having a job and a creative business "on the side". There is nothing wrong with ENJOYING BOTH. 

We all have different goals and aspirations and dreams. Some of that may include being a full-time entrepreneur and some of that may include doing a full time job and another part time job at the same time. We need to be able to give each other (and ourselves) grace to be who we are and pursue what we think is best for our lives. 

I didn't choose to become a full-time photographer...it happened by accident. We are in a place right now where I don't have to pursue a different full time job outside of what I do in my business but let me tell you there are certainly times when I would rather just go to work and do my work all day and then come home and read a book! Or watch TV without feeling like I should be "working on my business". 

Cinnamon Wolfe Photography | North NJ Wedding Photographer

Because let me tell you friends, it doesn't stop. Its ALL you, ALL the time and there really are no breaks. It's hella hard to give yourself the ability to have some down time or off time because social media is screaming in your face that you will.never.catch.up with what so-and so is doing. 

But here's the thing. You don't HAVE to catch up. You don't HAVE to do what they did. You have your own wins and successes and even though you might think this is silly...there are people out there thinking they will.never.catch.up with YOU. 

To every single person who has a "corporate job" or a 9-5 and they think that it's dead-end and horrible....or even those who feel like in order to be seen as a "success" or "legit" that they have to give that job up.....I'm here to tell you, your DREAM doesn't have to be the same as everyone else's.

Entrepreneurship is flat out hard and not everyone who starts down the path will end up in the same place. Evaluate what you really want to accomplish and WHY you want to accomplish it and then take action to get you there. If that means you keep on thriving in your day job, then by all means...rock it out and don't let anyone else make you feel bad because of it. 

That's it friends. If you have read this whole post, I can't thank you enough for taking the time. And I hope that some of this was an encouragement and inspiration for you to really understand what it is that you want to do and the path you choose to get there will always be your path, not someone else's.