Forty thousand photos.
That's how many photos both Shannon and Janine discovered they have on their phones, give or take a couple hundred. The discovery immediately raised a question: if there are forty thousand photos in there, why can't you find the one you're actually looking for?
From puppy pictures and sunrise photos to garden snapshots and Wordle screenshots, they talk about what's filling up their camera rolls, why organizing photos feels so daunting, and the surprising role that decision-making plays in all of it.
Along the way, they share a few approaches they're considering, a couple of things that already help, and a realistic challenge for tackling the backlog without turning photo management into a full-time job.
What We Talk About
- 00:00 — Discovering they each have about 40,000 photos on their phones and wondering how that happened
- 02:23 — Janine's search for an old puppy picture of Bix and the frustration of knowing a photo exists but not being able to find it
- 03:25 — How perfectionism and the search for the "right" system can keep a project from ever getting started
- 04:13 — A photographers workflow, photo-culling tools, and the challenge of managing huge numbers of images
- 05:51 — A photo-organizing course they both enjoyed—and why having a good framework didn't make the work feel any less overwhelming
- 07:17 — The surprisingly big role that tiny decisions play when you're sorting through thousands of photos
- 13:46 — Shannon's strategy of adding captions to photos so they're easier to find later
- 18:15 — A three-month challenge to stop their photo collections from growing even larger
Key Takeaways
- Sometimes the hardest part of organizing photos is making thousands of low-stakes decisions.
- Captions can make future-you much happier when it's time to search for a specific photo.
- Small rules—like deleting photos of labels after you've read them—can reduce clutter without requiring a massive organizing project.
- Looking for tiny pockets of time may be more realistic than scheduling a long photo-organizing session.
- Maintaining new photos may be easier than trying to solve a backlog of 40,000 all at once.
- You don't need a perfect system before you start making things a little easier.
The Bottom Line
This conversation begins with a surprisingly specific problem—finding one photo among forty thousand—and quickly reveals that both Shannon and Janine are dealing with the same thing: a collection that's grown faster than any system they have for managing it.
Rather than searching for the perfect solution, they explore a few practical ideas, a few imperfect ones, and a few habits they might actually stick with. And that may just be enough. The next time you're waiting for an elevator, standing in line, or looking for a photo you know is in there somewhere, consider deleting a few duplicates, blurry images or mysterious shots you can't even identify.
Want More Like This
Episode 227: Making Tough Choices Easier
This episode explores the mental load of decision-making and ways to save your energy for the choices that matter most. If choosing between nearly identical photos feels oddly exhausting, you'll relate to this conversation.
Episode 92: Working Through a Backlog
Whether the backlog is paper, email, or photos, the challenge is often the same: figuring out how to make progress without feeling overwhelmed. This episode offers ideas for tackling accumulated projects one manageable step at a time.
Episode 66: Daily Habits
Shannon and Janine discuss how small, repeatable actions can make life easier. It's a nice companion to this episode's idea of handling photos a little at a time rather than waiting for the perfect organizing day.
Connect With Us
How do you manage your photos? Do you have a system—or are you staring at a camera roll full of poodles, sunrises, screenshots, and mysteries, too?
And if you know someone who has ever said, "I know I have a picture of that somewhere," send this episode their way.
