The Picture I Wish I Had Asked About

After I left my corporate career in IT project management and before I began my new chapter in real estate, I found myself in an in-between space. I didn’t know exactly what I wanted to do next. I knew I needed to do something joyful and purposeful in my next career.

That year, understanding it would take me time to figure it out, I turned my attention to something long overdue: our family photographs.

There were thousands of prints, negatives, envelopes from the photo lab, and albums collected over the years. When we raised our children, there were no phones to document daily life. Everything was on film, and everything had to be printed, regardless of whether it was a keeper. I had also inherited or made duplicates of photos of my parents, grandparents, great-grandparents, weddings, and family gatherings from generations past. 

I sat on the floor surrounded by bags and boxes of pictures. I sorted through them. I discarded blurry shots, duplicates, and forgotten scenic views from places we no longer remembered. I scanned the photos we wanted to keep with meticulous care and attention. I purchased a scanner, learned the software, and labeled every file with both dates and relevant keywords. I created metadata so we could find pictures by person, place, or event. It was my quiet project, my transitional therapy.

Today, every member of my family carries this visual history in their pocket on their phone. Decades of memories are now digitized and enriched with recent additions to our digital lives. I can pull up a picture of my grandmother or my great-grandmother with just a few taps on my iPhone. I can see my kids as toddlers, teenagers, and now adults anytime I want.

Yet, as meaningful as those images are, they also raise questions.

There’s one photo that has stayed with me. It’s of my paternal grandmother, Rose. She’s sitting in a rowboat, gripping the oars with determination. Her two young children, my father and my aunt, are with her, along with two other people I don’t recognize. She’s wearing a confident expression, her eyes gleaming with mischief and strength.

She was a force. Rose was short in stature, about five feet tall, yet mighty in every other way. Rose was opinionated, fiercely loving, and quick-witted. Looking at that photo, I can feel her spirit. I can’t help wondering: Where were they? What was that day like? Was this adventure in the 1930s something women typically ‌did on their own?

And then there’s another image, one I saw only once and which seems to have vanished.  Rose is in an office, surrounded by a dozen men, all smiling down at her. She’s seated in the center, smiling radiantly. One man has his hand resting near her shoulder in a way that looks friendly, perhaps protective.

What was she doing there? She stayed home all of her life, raising her kids while her husband worked as a milkman. But here she was, looking entirely at ease in what appeared to be a work setting. Did she take a job later in life? Was this a family business gathering? A club? A reunion?

I wish I had asked.

Those photos remind me how much legacy lives in the details we often overlook: the curve of a smile, the way someone dresses, and the people surrounding them. And yet, those pictures can only tell us so much.

Legacy writing is about filling in the gaps. We bring images to life with context, emotion, memory, and a sense of curiosity. Sometimes, we are lucky enough to sit down and ask questions when the storytellers are still here. At other times, we examine what’s left and piece together what we can.

That’s love. That’s honoring what remains.

Looking back, I’m grateful for the time I took to digitize those photographs. But more than anything, I’m thankful that those pictures continue to spark wonder and storytelling.

If you’ve ever found an old photo and wondered about the story behind it, take the time now to ask someone or to write what you know. Your wish to know their stories will delight your family. They will happily share them with you. Generations that follow will thank you. 

Not every photograph comes with a caption. 

Yet, every photograph is part of a story.