To be a teacher is to shove all housekeeping tasks to those tight windows of time when the grading goes away. All semester long, dirty laundry piles up. The lawn grows unchecked. And then, just after my semester ends in December, or May, or August, I schedule long-overdue oil changes and haircuts and dental appointments.

A few weeks ago, at the close of the university’s finals week, I sat in my home office and took stock of the clutter I’d allowed to build while immersed in teaching’s daily tedium: the piles of unread (and hopefully non-urgent) mail, the stacks of magazines, the abandoned safety pins from various 5K bibs, the old printer-paper boxes now stuffed with…who knows what? And I convinced myself that now, with a hint of free time before classes resume, I would finally de-clutter.

Except, well, putting things away wasn’t as easy as I’d imagined.

I’m expected to be part of the generation for which iTunes purchases are a first option, the generation that can do everything on the phone (completely paper-free). But my dirty secret is that I do struggle to go digital. My desk is littered with Post-its that—were I more technologically adept—might instead be rendered in some task-list app.

It wasn’t until last year that I finally switched to e-statements for my bank account, and my phone bills (still delivered via postal service) contain each month some new snarky message about how I’m killing the environment by not going paper-free. (Every month I try to log in and change this, only to be rebuffed by forgotten usernames and passwords and…aw hell, what with identity theft and the 200 passwords I must remember to avoid it, and with deep fears of a Revolution-style power outage that dissipates the cloud and all of my data, it’s a wonder I do anything paperless.) I’m 33, and feel like I’m living in a generational No Man’s Land between digital dependency and digital illiteracy.

After all, it’s considered okay for my parents to have boxes of old home movies, to have decades-old field guides to snails and mushrooms, but I am expected to be above any such attachment to outdated mediums or print artifacts. Heck, I used to make fun of my father’s bulky record collection (stored, no joke, in an old phone booth that my parents keep in their foyer), or my mother’s full bookshelf dedicated to 1970s encyclopedias. I snottily bemoaned their collections of old crap; I’d grown up with Microsoft Encarta in the ‘90s, then made my seamless transition to Google searches and Wikipedia in the 2000s. How foolish to own encyclopedias!

But now the joke’s on me. Unlike the younger, paper-free iGeneration, I’ve mostly lived a pre-cloud life. My ‘90s were consumed with CD purchasing, and so I have shelves of discs from middle and high school (Hey look, the Wayne’s World soundtrack!); my wife’s CDs are there, too, the entire catalogue of Backstreet Boys and Boyz II Men. My generation popularized Napster and the MP3 movement, sure, but we also have boxes of leftover Goo Goo Dolls and TLC CDs, the fixtures of a normal turn-of-the-century life. Not long ago, the homes of my generational peers were also cluttered with DVDs that we shouldn’t have purchased (see: the ALF boxed set), and with video rental boxes we had to keep in prominent places so that we wouldn’t forget to return them, thus accruing late fees.

Clutter felt…normal. But now, there’s no Blockbuster, and entertainment is streamlined by Netflix and Hulu, a world of cinema accessible through iPads and Blu-ray players…we’re not supposed to own physical objects…But still, many of us are burdened by those tons of plastic discs and cases.

But for someone my age, it’s the photographs that are the worst.  

There are old photo albums in my home office that…well, quick question: Who still buys physical photo albums? The crunchy plastic pages…the awkward triangular shape that disrupted the perfect line of books on your shelf? Much is made about how quickly kids grow up in the Facebook Era, but here’s where kids have it good: They don’t have to open their scanners and, over and over again, transfer printed photograph to digital file…15-year-old photos that were once prized possessions, but whose quality is worse than the accidental pictures you take on your iPhone.

Let me be clear: I’m not a hoarder. I want to live digital and uncluttered. But just when I make progress with conversions, some other physical object is made irrelevant by a new app or web site. My generation is expected to negotiate the spaces between print and digital, to convert to digital what had been physical for a lifetime, but we don’t get the “pass” that is handed out to someone 10 years older…we’re not the old Mom joining Facebook and accidentally tagging her son in a picture of her dog…if it wasn’t for us, there would be no Facebook.

This year, to unclutter my office, I finally scanned the stacks of photos I’d shoe-boxed for years. And for one full day this December, I plugged my camcorder into my computer and transferred two years’ worth of videos. My son running around in his Where the Wild Things Are Halloween costume, or riding It’s a Small World at Disney and (justifiably) crying in terror. My dog belly-flopping into the pool. I rotated videos. Created folders. Renamed files. Yes, it was tiresome, but not nearly so terrible as in the days of videocassettes. The current generation will never know the awfulness of searching boxes of VHS home movies to find “Easter ‘89” for their nostalgic mothers.

Still, despite how amazing it sounds to live in the cloud, the digital uncluttering has become not liberating but exhausting. When the photos are scanned and the CDs are ripped, will I then spend full weekends “uncluttering my desktop,” endlessly organizing folders on my devices, trying to make the digital information ever more accessible, editing “Easter ‘89” to perfection, searching for the most recent digital task-list that I commended myself for having typed on my phone…but which has long since disappeared into the haze of clutter obscuring the screens of my devices?

Perhaps. Or maybe I have nothing to fear. If I just procrastinate long enough, maybe photo albums and VHS tapes will come back into style.

Nathan Holic teaches in University of Central Florida’s Department of Writing & Rhetoric. He can be reached at