Welcome to Live with Mollie. It is Tuesday, August 5th, and I’m here to be your photo organizer, resource, and helper. I truly love helping people feel confident and motivated in saving their family memories. During this live episode, you can definitely post questions in the comments area and I’ll try to answer them. I’m curious if anyone will chime in today, or maybe later when watching the recording. I think people often struggle when it comes to knowing what questions they should be asking. Honestly, I hadn’t thought much about that before, but I’ll dive into it in just a second. Before we get there, I want to remind those of you listening on Spotify or elsewhere that we are also on YouTube, where I share visuals that may help you follow along.
I have a few announcements today. First, we are passionate about reminding people to save last month’s photos. This habit is so important for building structure in your photo collection, saving the pictures that truly matter, and giving yourself a small but meaningful win each month. I know it’s easier said than done. For example, I’m actually showing my pictures from June today because I still haven’t saved July’s photos yet. Last month I lost a phone, got an Android for work, and also had a replacement iPhone—it has been a juggle, even for me, and I do this every day! Still, I try to have last month’s photos saved by the fifth of each month, which happens to be today, so that’s my personal goal for later. I want to encourage you to adopt this practice as well. At the end of the year, when you’ve consistently saved photos month by month, you’ll be amazed at how much easier it is to create folders, albums, or even projects with only the photos that really matter.
My second announcement is that registration is now open for the Save Your Photos Virtual Bootcamp. I’ll post the link in the comments if you’d like to learn more. This event helps you take action on your photo projects, which is also the best way to know what questions to ask. It starts with “Get Prepared Monday” on September 15th, where you’ll join online for an hour session with tips to get ready for the bootcamp. The actual bootcamp begins Friday, September 26th, with an evening session, then continues all day Saturday, September 27th, from 9:00 to 3:00, with additional time afterward for those who want to keep working. You can attend virtually for $119 through August 15th, or in person here in Milwaukee for $149 before the 15th. Prices increase after that. I’m especially excited because my former business partner and Pixologie co-founder, Ann Matthews, will be joining me, and we always have a lot of fun helping people save their photos.
Another upcoming event is our photo organizing cruise, scheduled for February 16th through the 21st. I’ll share the video link with details, but the idea is to create a relaxed environment where you can enjoy time away while also working on your photos. You’ll be able to pick my brain and also my friend Krista Kowalczyk’s, and it’s designed to be a no-pressure, enjoyable experience.
I also want to let you know there will be no Live with Mollie next Tuesday. On the second Tuesday of each month, I’m with my PixPlan group for a three-hour workshop. And again, I’ll say it: once you start working on your pictures, that’s when you begin to discover what questions you really need to ask.
That brings me to a story. I answer questions all the time—on the phone, in my office, over Zoom, on YouTube. But recently, on one of my PixPlan support calls, a member named Pam leaned in close to her computer and asked me something I had never been asked before. She said, “Mollie, what questions do you want us to ask you?” It caught me off guard because I had to think about it. At the same time, another member was describing her overwhelm—OneDrive issues, boxes of photos, not being sure if her prints were even organized chronologically. She didn’t even have a specific question, and that’s the thing: sometimes you don’t know what to ask when the project feels so big.
Here’s the truth: when people have photo organizing questions, I know they are actually doing the work. In my community, when I see lots of questions, I know people are putting in time—sometimes hours a week—on their photos. And when questions aren’t coming, that usually means people aren’t engaged with their collections. So my advice is this: whether you’re organizing digital or print photos, keep a clipboard by your side. Take notes on your progress and also write down questions as they come up. Don’t try to hold it all in your head. I especially need that now that I’m over 50 and forget things more easily!
When it comes to photo organizing questions, I see three main categories: technical, structural, and process. Technical questions are about equipment and programs, like “Is my computer good enough?” In general, if your computer is less than three years old, has at least 16 GB of memory, and plenty of storage, you’re in good shape. Another common one is “How do I digitize old VHS tapes?” My honest answer is: don’t do it at home. It’s a frustrating process, and the quality usually isn’t great. We recommend sending them out to companies that specialize in digitization, like FOREVER, because they can actually improve the video quality during the transfer. Another technical question is “What’s the difference between iCloud and OneDrive?” Simply put: iCloud is Apple’s cloud, OneDrive is Microsoft’s, and Google also has Google Drive. Having more than one can get messy if you don’t fully understand what’s saving where.
Structural questions are about how your collection is set up. Are you using folders? Albums? Just one big gallery? Structure matters because it makes your photos findable. A common question is “How should I label my folders?” The formula I recommend is: year, dash, month, day, and then a description (for example, 2024-08-05 Beach Trip). You can adapt this depending on what you’re organizing. Another big one is “How many photos should go in each folder?” My guideline is between 25 and 250 so that folders stay manageable. Typically, you’ll set up a layered structure: decades at the top level, years within those, then months inside the years. Another question I often hear is “Can I organize photos by person?” The short answer is yes, but I don’t recommend it. I’ll be covering that topic more deeply in the next episode on August 19th.
The last category is process—how we actually get things done. For example, people ask, “Why isn’t my duplicate finder working?” Usually it’s because of a messy folder structure or missed steps. Duplicate finders are powerful but work best when paired with solid structure. Another process question I hear less often but think about a lot is, “Can AI help with photo organizing?” At this point, I don’t think AI is very useful for the actual organizing process, especially when it comes to handling duplicates. Where AI is showing up more is in creative features, like MyHeritage’s “Live Memory,” which can animate old photos with effects. Google Photos is also adding AI-powered features like turning photos into videos. Personally, I see these as distractions from the real work of organizing. That said, AI is evolving fast, and companies like FOREVER are planning to use it in the future for things like generating photo books or life stories—after your photos are already organized.
So here’s the bottom line: questions are a sign of progress. If you’re not asking any, it likely means you’re getting work done, which is still a win. But as you dig in, questions will naturally start to appear. My advice is simple: start working on your photos and write your questions down as they come.
That’s everything I wanted to cover today. Thank you, Sierra Francesca, for your kind comment—it really means a lot. I know so many people out there feel overwhelmed by their pictures and don’t know where to start, or even what to ask. So remember the two takeaways: start working on your photos, and write your questions down. I’ll see you in two weeks, on August 19th, when we’ll talk about why you don’t even need to know who’s in your photos to organize them. Until then, make sure you subscribe so you don’t miss future videos. Take care, and have a great week!
