Quick honesty check. How many thousands of photos are sitting on your phone right now, completely unsorted, that you have not looked at in over a year? No judgment. Mine is embarrassing too.
Today's issue is a lighter one, and I think it might be one of the most immediately satisfying ones we have done. AI has quietly gotten very good at helping with the photo chaos most of us are sitting on, whether that is ten thousand phone photos or a dusty shoebox of prints from your parents' basement.
A quick word on privacy first
Family photos often include kids, other relatives, and identifiable details like street signs or licence plates—people who never agreed to have their photo uploaded anywhere. Stick to tools built into your phone or a reputable, well-known app for anything involving photos of other people, especially children, and take a look at what that app actually does with your photos before you upload a big batch. A little caution here goes a long way.
Four things to try this week
1. Use the search you already have and probably never touch
This is the one most people do not know they already own. Both Google Photos and Apple Photos now let you search using plain, everyday language instead of scrolling forever. You can type something like “the dog at the cabin” or “birthday cake” and it will actually find the right photos, no folders, no tags, no work required on your part.
Marion in Kamloops was trying to find a specific photo of her grandson's first time in the lake for a slideshow she was putting together. Instead of scrolling through three summers of photos, she typed “grandson swimming lake” into Google Photos search and found it in about four seconds. She had genuinely never used the search bar for anything before that day.
“[PERSON'S NAME OR RELATION] at [PLACE OR EVENT]” — for example, “mom's birthday cake” or “kids at the cottage.”
2. Build yourself a simple plan for tackling the backlog
If the idea of organizing years of photos feels overwhelming, that feeling is exactly why it never gets done. Ask AI to break the whole mess into a simple, realistic plan you can actually follow, a little at a time, instead of trying to fix it all in one exhausting weekend.
Fatima in Mississauga had roughly six years of unsorted phone photos and was about to move, which made the thought of dealing with it even more stressful. She asked ChatGPT to build her a simple weekly plan for sorting through them a year at a time, deleting duplicates and blurry shots, and creating a few basic albums. She gave herself fifteen minutes a night and had it done within a month.
“I have roughly [AMOUNT OR TIME PERIOD] of unsorted photos and it feels overwhelming. Can you build me a simple, realistic plan for sorting through them a little at a time, using about [TIME AVAILABLE] per session, so it does not feel like one huge project?”
“I have roughly six years of unsorted phone photos and it feels overwhelming. Can you build me a simple, realistic plan for sorting through them a little at a time, using about fifteen minutes per session, so it does not feel like one huge project?”
3. Write down the family history before it disappears with you
This one is less about tidiness and more about something that actually matters. If you are digitizing old family prints, you likely know details nobody else does: who is in the photo, where it was taken, what was happening that day. Once you write that down, ask AI to help turn your rough notes into a clean, organized caption or short family history entry that will actually make sense to someone reading it in twenty years.
Walter in Trois-Rivières spent a weekend scanning his late father's photo box, most of it from the 1960s, with nothing written on the back. He jotted down whatever he remembered his father telling him about each one, sometimes just a name and a rough year, and asked Claude to help organize his scattered notes into a simple, readable caption for each photo. What used to be a box of mystery faces is now something his kids can actually understand.
“I am digitizing old family photos and have some rough notes about each one. Can you help me turn these into clean, simple captions that explain who is in the photo and what is happening, in a way that would make sense to a family member reading it years from now? [PASTE YOUR ROUGH NOTES]”
“I am digitizing old family photos and have some rough notes about each one. Can you help me turn these into clean, simple captions that explain who is in the photo and what is happening, in a way that would make sense to a family member reading it years from now? Notes: this one is dad and his brother Real at the cabin, maybe 1968, before it burned down the next winter.”
4. Bring an old, faded photo back to life
Tools like Canva and the image features in ChatGPT and Gemini can now clean up scratches, restore faded colour, and sharpen old blurry prints. This is not the same as a professional restoration, and it works better on some photos than others, but for a scanned print that has faded badly, it can genuinely bring back detail you thought was gone for good. This is squarely a “photos of family you already have full rights to” situation, not something to try with photos of strangers or public figures.
A reader in Charlottetown had a badly faded wedding photo of her parents from the early 1970s. The colours had gone almost entirely orange with age. She scanned it and used Canva's photo restoration tool to bring back the colour and clean up some scratches. It was not perfect, but it was good enough to frame for her mother's eightieth birthday.
“Can you restore this old photo, fixing fading, scratches, and blur where possible, while keeping it looking natural and not overly edited?”
Your challenge this week
Pick one photo you have been meaning to find, restore, or write something about, and just do that one thing today. You do not need to fix the whole backlog this week. Start with the search bar. It genuinely takes four seconds and might be the easiest win in this entire newsletter so far.
Coming up next issue
Next issue we are back to business. If you invoice anyone for anything, even occasionally, we are looking at how AI can help you write invoices and, just as importantly, follow up on the ones that never seem to get paid on time.
Whatever AI produces for you, always read it, verify it, and make it sound like you. AI is an incredible first draft machine. Your judgment, your voice, and your values are always the final layer.