I Have 20 Years of Digital Files. What Do I Do With Them?

There are thousands of documents saved on my computer. Deciding what to keep took me on an unexpected journey.

By Robbie Shell, Wall Street Journal, April 8, 2025

I started with “A” and a Word document labeled “Advicetokids.” It was followed by 149 files—and that was just the A’s.

This was going to be a huge project.

The A’s were the kickoff to downsizing what I came to call my “digital basement,” the cluttered home to thousands of Word files, some dating back to 2001, most no longer relevant or particularly interesting.

The practical goal: to end up with a much smaller document folder that I could easily navigate without getting tripped up by enigmatic file names like “zucc,” “facts” and “orourke.”

But I sensed from the beginning that this would be more than a routine housekeeping chore. It would be a journey through the past several decades of my life—the digital equivalent of a time machine—reconnecting me to people and events I hadn’t thought about for years and stirring up memories of unfinished projects and unfulfilled ambitions.

Equally important: I wanted to create a streamlined, curated folder that would offer my children, when the time came, a more accessible window into my life, and by extension, theirs.

The downsizing promised to be a slog. After all, our baby boomer generation is the first to have technology allowing us to effortlessly create a digital archive with the small and large details of our existence. It’s a mixed blessing given the unlimited space that technology offers and my preference for storing files alphabetically rather than in defined folders. With the ability to save every proposal, draft, report, idea, reference or random thought, whether deserving or not, I had created a monster.

The easy stuff

I started by deleting most of my work-related files along with early drafts of essays and a published novel. Another easy lift: saving the more practical files—contact information for people and places, medical records and recommendations for books.

From there, many of the files I ended up saving were simply evocative reminders of time and place. “Advicetokids” was a letter to my sons I wrote shortly after the Covid lockdown began in March 2020. “The suggestions below are…random insights I feel the need to share now, in the summer of 2020, when life itself has never seemed so defenseless,” recalling once again the vulnerability and dread we felt during the peak of the pandemic. My sons might never read this letter, but the file will be there just in case.

“Memorieskids,” created in 2010, followed a request from our sons to write down memories of their childhoods. My husband and I responded with three single-spaced pages, most of them recalling happy memories—watching shooting stars from the deck of a North Carolina beach house; tiptoeing through one son’s “Santa trap”—a house of cards set up next to the fireplace designed to prove once and for all that Santa wasn’t eating the milk and cookies (it failed); listening to both boys spontaneously belting out “I Am a Pirate King” in our front hallway. Other memories were harder—three of us eating the leftovers of a hospital cafeteria’s Thanksgiving dinner while our older son was recovering from surgery for a ruptured spleen.

I have sent this file to my sons over the years and hope that they do the same for their own children, should they ask. The file even offers some clues about child rearing—things we as parents did well (encouraging one son to participate in a wilderness program out West, encouraging another to take up a musical instrument in fourth grade), and things I wish I had the opportunity to do over.

One of the best memories was in a file I hadn’t remembered saving called “scavengerclues.” It has the 10 rhyming four-line clues I wrote one Easter for my husband and sons, continuing a tradition I started in 1998 and kept doing until the kids were grown. Each clue contained one or two randomly chosen words that hinted obliquely at where the next clue, always accompanied by a small gift, would be found. It’s a tradition I hope my sons continue with their own children and find the same joy being together that I found with mine.

“Nednettie” is a tribute I wrote in 2009 to my younger son’s nanny whom he stayed close to until the day Nettie’s daughter called him in his college dorm room and asked him to come to the hospital. Nettie, 84, was dying. My son talked to her and held her hand while they disconnected the life-support system. I sometimes found myself a little jealous of their love for each other all that time, especially during the teenage years when children begin the process of separating from their parents. He never separated from Nettie, calling her when he was on summer-abroad programs, taking her for slow walks around her neighborhood when he was home on vacation. I never had such an uncomplicated, nurturing relationship with an adult when I was growing up. I remain forever grateful that he did.

A ride best forgotten

Several files were in-depth journals I kept during trips around the U.S. and abroad. One dating back to 2000 describes the terrifying state-of-the-art roller coaster ride I persuaded my then-10-year-old son to go on at an amusement park outside Stockholm. My theory was it would help us conquer our mutual fear of such rides, but I knew from the moment we were locked into our seat that it was a huge mistake. Arms linked, we shut our eyes and screamed the whole way down. While I can laugh about it now, I also remember that day as the dawning of a hard realization—that as a parent, I had screwed up, that a plan I thought was so wise and “parental” (in this case, “face your fears head on”) could simply be wrong.

Other files I read through reintroduced me to people I met while volunteering with local organizations. One is a profile of a man in a specialty nursing care facility who eventually died of complications from progressive multiple sclerosis. He had once traveled the world advising high-school language teachers on their curricula before he lost the ability to walk and speak. During visits to his room, I would pick out one of his favorite books and read a few pages to him before he fell asleep. I still visit this facility most weeks. When I leave, I feel thankful that I am able to play a limited but I hope meaningful role in some remarkable people’s lives.   

In the end, having saved just 200 files out of several thousand, I realized that the exercise was more than decluttering. It also taught me there is much to be learned by looking, not only forward, but back as well. All these files and others that remain are like letters written to myself, saved in the same way I used to save handwritten letters from friends long before computers made them close to obsolete. Each letter, each file, is a piece of gold hidden deep in a river bed—a discovery whose value grows and changes each time I hold it up to the light. 

Source: Robbie Shell, Wall Street Journal, April 8, 2025