Stop me if you heard this one before: my inbox/Google Drive/hard drive is a mess.

While everyone out there is not a collector or hoarder, I’m sure than more of a few of us have opened our computers and gone searching for whatever needle is in whatever haystack that we know we have, but damn if we don’t know where we put it. And if you are like me, you have files that are old enough to have children.

I bring this up because last week, I bought a new laptop (thus checking something off my “50 Before 50” list). My wife told me about a massive sale Dell was having and I could not pass up the chance to get a laptop at nearly 50% list price. Setup was easy. Porting files from my old laptop was a simple copy/paste from an external hard drive I’d been using since my old laptop was showing signs of dying (in fact, it took three tries to start it up so I could clear out all my files). But then I had to go through what I brought over and clean it up a bit. A number of folders were disorganized or redundant and there were simply files that I knew I was not going to need on the new computer and could stay on that backup drive.

Then there’s the stuff that’s simply … well, old. And what do I do with that?

I guess i don’t need those agent query letters from 2009. And a folder labeled “correspondence”? What am I, some 19th Century industrialist whose family is going to preserve my letters for when people tour my mansion after I’m dead? Yeah, much like boxes of old work or water bills from four years ago, some things definitely needed to go.

I’m not going to walk you through the process of deleting files. It’s not exactly exciting. But there were some things that I’d forgotten I held onto. I think the “why” of them falls into two categories: things I wanted and things I forgot I had. Like old Skype recordings and raw podcast files, some of which are fine on backups and others don’t need to be preserved, like repeated calls to the Skype Sound Testing Service. I think my relationship with her is in the past. Or the four folders of backups from old thumb drives and work computers. I think that the statute of limitations on the journalism course I taught from 2005-2008 has passed, and despite my love for it, I think that I probably am never going to teach All Quiet on the Western Front anytime soon. And resumes from 20 years ago? Okay, I probably just left those there and forgot I’d never deleted them.

But what about the more interesting stuff? You know, the things that made me pause for a moment and open a few files? Well, here’s a few along with what I did with them.

Email Forwards from College. Remember freshman year of college when you got your first email address and you’d send anything to anyone for the sheer novelty of it? We passed around so many forwards, many of which were random lists like “50 Ways to Mess With Your Roommate” or “100 Signs You Grew up in the Eighties.” And purity tests where you and everyone on the floor sat around and confessed whether or not you performed various sex acts. Then there were those emotional essays about going to college and being on your own for the first time. I was a sentimental mess when I was a teenager and fell for those like crazy.

I actually shared a number of these on Pop Culture Affidavit in 2014, so I didn’t feel the need to keep them around and deleted them from my hard drive. But I also just had a kid go through their freshman year of college and they have a love for memes (many of which I don’t understand) and I know they made friends by bonding over random things. And that was the point of those forwards, right? You’re in a new place with new people and you seek out people who have the same sense of humor or who don’t mind having oddly deep conversations until 2:00 on a Saturday night.

My College Papers. Yes, I still had every single paper I wrote in college, neatly organized by year and then by course. Same can be said for graduate school. I’ve pulled one or two out over the years to show my students what MLA formatting looks like and my student teacher and I last year showed examples of well-written and overwritten thesis paragraphs. Otherwise, they’ve just sat there. And while I am impressed at how well I was writing 10-20-page papers by the time I hit my senior year, I don’t know if anyone really cares about my 25-pager on comic books as modern mythology from my Honors Senior Seminar course at Loyola.

I did, however, keep all of the creative writing class files. There were some old poems and short stories in there that are worth holding onto as past examples of work. Well, except for the crap I wrote in a “Writing for the Stage” course my junior year. That was the year I had horrific writer’s block and it showed (in that and my fiction-writing class). It’s not like I’ll be submitting any of those anytime soon, but it’s nice to have an archive.

The Remains of My Teacher Blog. So in 2021, I wrote an entry called “When I Was a Teacher Blogger” where I went through my history of writing and tweeting as a teacher, then came to the conclusion that maybe I’m better off not writing about teaching because it had a negative effect on my mental health, contributing to my anxiety along with propagating a huge chip on my shoulder when it came to teachers who were self-proclaimed “Thought Leaders” and “Innovative Educators.” The blogs were taken down a long time ago, but I’d downloaded the raw text before doing that, probably as a record of what I had written and for possible inspiration for an essay or two on teaching.

I still would love to write about teaching in some capacity. I have a whole archive of ramblings I’d kept in a notebook over the last few years that were outlets for my frustration at various things in education, and there’s a book in my head somewhere (just like every other teacher). There’s some of the same sentiments and ideas, but I feel like those old blog entries are a past me that I’m comfortable with leaving in the past. Not out of shame, but out of acknowledgment that I’ve grown as both a teacher and a person and I don’t need to hold myself to how I was in my twenties or thirties.

Published Stuff. I’m obviously going to keep this folder. It contains anything that was published in some form beyond my blogs, such as articles I wrote for school and local newspapers, odd essays I wrote for websites that no longer exist, an op-ed about free speech and high school yearbooks I wrote for Education Week years ago, and a couple of poems that were actually published somewhere. Where, I can’t remember, but they were published. I’m hoping to add to this one.

Old Manuscripts and Book Ideas. I’m writing a novel right now. It’s in its second draft and I’m enjoying it because I’m not putting pressure on myself to publish. I’ll definitely try, but my motivation is just to have fun and tell a story. That being said, there are four other novel-length manuscripts on my computer that I wrote between 1998 and 2012. Two of them were for NaNoWriMo. Three of them feature the same characters. I’ve gone back and re-read them and out of the four, I see that two of them might be worth another look, maybe even a rewrite. The other two aren’t. One was my second NaNoWriMo novel that I never went on to finish because by the end of that endeavor, I wasn’t really into the book. The other had some great stuff but I abandoned it in the middle of a revision because it just wasn’t working. Maybe that one has some things to pick up? Yes, some of it is definitely cringe-worthy, but unlike the teacher blog stuff, I don’t feel like I need to leave it behind in a “that’s not me” sort of way.

Genealogy Research. I’ve been researching my family tree on and off for the past 37 years, ever since I had to do the family tree project in my seventh grade social studies class. It’s something I’ve collaborated on with a few members of my family–mainly my mom and my sister–and something I continue to do. In fact, ever since I discovered that my local library has free access to Ancestry.com I’ve gone when I can to do all sorts of searches and have gone a little deeper into my Italian and German backgrounds. Plus, I’m looking into dual citizenship in Canada since my grandmother was born in Newfoundland. It’s a bummer that I’m going to have to pay for another version of Family Tree Maker, but that’s okay because these are fun rabbit holes to fall down (and have provided the occasional research/information for some of my fiction).

The “Sayville 1995-1996” Folder. Okay, so you see the image at the top of this post. It’s of this folder I’ve had since I was in high school that was originally saved to a floppy disk. In fact, I think that some of the files predate 1995 and I know at least a few of them were written using WordPerfect. Plus, the file names are a little ambiguous because these were all created back when file names could only have eight characters.

I feel like this needs a deeper dive, to be honest. And not everything will be shown because I’m pretty sure that some of these files are love letters and love poems for old girlfriends. Some of them are assignments from senior year creative writing, like the file “Ballad,” which is a poem called “A Ballad of a Summer Forgotten” and tells the story about how the romance between a boy and a girl left his guy friends in the dust. I think I was going for Brenda and Eddie from “Scenes from an Italian Restaurant.” There is a “scenes” short story called “Scenes from a High School Prom.” That one made its way into my high school literary magazine and is actually where characters from more than a few short stories and unpublished novels come from.

And poetry. Oh, the shitty, shitty poetry. I think I’ve written enough about that, although there’s probably more in that well. I mean, this is all extra cringe-worthy and I will probably delete at least some of these as I do that deeper dive.

I guess it’s a cheat that I didn’t bother to delete any of this stuff from my backup drive (because I’m lazy), but I feel like doing this bit of digital decluttering helped at least a little.

Now, about my inboxes and Google Drives …