LWM 16 - Yes, No & Maybe - A good strategy

In this episode of Live with Mollie, I’m joined by my friend and colleague Lori Lafferty of Photo Legacy Digital Solutions for a real-life case study that so many of you will recognize. We dive into the popular “Yes, No & Maybe” photo sorting strategy, why it feels so right at first, where it can break down, and how to turn that growing maybe pile into real progress instead of frustration.

Lori generously shares her own family photo project, including inherited boxes filled with photos, negatives, slides, newspaper clippings, and memorabilia. Together, we talk through what actually works when you’re overwhelmed, grieving, short on time, or unsure who’s even in the photos anymore. This episode is full of practical organizing advice, mindset shifts, and permission to slow down and do it the right way so your family memories are preserved and enjoyed for generations.

As always, I also answer viewer questions about organizing, digitizing, scanning oversized items, videos vs. photos, and even digital photo frames. If you’ve ever felt stuck staring at boxes of mixed memories, this episode will give you clarity and a path forward.

0:00 Welcome & letting viewers join
3:44 Show intro & mission of Live with Mollie
4:13 Announcements: Upcoming cruise & live course updates
6:47 Guest introduction: Lori Lafferty & her memory preservation work
9:07 Introducing the “Yes, No & Maybe” sorting strategy
10:20 Why the maybe pile grows out of control
12:53 The emotional challenge of unidentified photos
16:17 The 3-step system: Organize → Digitize → Preserve
18:22 Why organizing is the hardest (and most important) step
21:12 Real-life example: Gathering everything into one place
22:09 Sorting by family groups and categories
23:30 What organized photo boxes really look like
24:22 Creating batches for scanning & folder structures
26:46 Viewing and discussing Lori’s family photos
29:01 Newspaper clippings, memorabilia & unexpected discoveries
31:03 Talking with aging parents about photos & dementia insights
33:16 Why future generations will care about your photos
34:11 Sorting photos to share fairly with family members
35:36 Practical tips: labeling piles & working with limited space
37:07 A meaningful family milestone photo
38:30 Q&A: Scanning newspaper articles & oversized items
40:27 Q&A: Deleting photos from an iPhone after transfer
43:07 Q&A: Organizing videos vs. photos
46:11 Q&A: Digital photo frames vs. smart TVs
48:01 Final advice: Don’t wait to work on your memories
48:25 Preview of next episode & wrap-up

LINKS MENTIONED IN THE EPISODE

Submit questions for future episodes email: [email protected]

Watch Episode 16 on YouTube - https://youtube.com/live/dzqwLZ8bMb4?

Cheers!

Mollie