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A Drop in the Box

I use Dropbox—almost exclusively—for digital storage of all my photos, documents, syllabi, manuscripts, invoices, and to-do lists. I bought a subscription to this service nearly a decade ago to allow me to switch seamlessly back and forth from my campus computer in the basement office I shared with two other researchers, and my slow-running laptop back at home, as I worked on my dissertation.

At the time, I didn’t think much of the service. That doesn’t mean I thought poorly of it; just that I didn’t think much about it. And after five or so years of use, it started to show how little I thought about it. When you opened my Dropbox, you saw absolute chaos—no order, duplicate files, endless photos, an unprecedented deluge of loose documents all named “Meg Myers Morgan” and on and on. Every time I opened it—which was no less than five times a day—I was hit with a pang of anxiety, which quickly turned—as my anxiety is wont to do—into shame.

But over the years, I had resigned myself to the anxiety and shame because I was too busy living my life to spend any time organizing it. I couldn’t possibly sit down and try to arrange all the files when my child needed to eat, my students needed their syllabus, or my accountant needed our W2s. So instead of tackling the organization, I just decided that every day, dozens of times per day, I would hunt through the mess with word-searching and educated guesses until I found the one file I was looking for—often 15 minutes later.

And on and on my life went over the years—finishing my PhD, having our second child, writing a book, accepting a faculty position, writing another book, getting certified in executive coaching, taking on a handful of clients, and working on a third book.

And that third book halted everything.

More specifically, it halted my understanding of myself as a writer. Not because writing was emotionally taxing or that the publishing industry is onerous (though both are true). But because I couldn’t see who I was as a writer anymore. One of the tough aspects of my writing career is that it has been much more haphazard than intentional. Which is to say, it’s developed with me, grown with me, changed with me. It was never, not ever, a far off target I’ve been trying to hit. It has always been a progression of my life, my thoughts, and my feelings.

My first book was a collection of (hopefully) humorous essays about motherhood, marriage, and the ups and downs of trying to grow a career. My second book was a professional development book about the negotiations women make in their career (especially with the pulls of personal life). Currently, I’m contributing to magazines about effective communication and coaching on a regular basis. I am still publishing on my blog a decade after starting it. But, now what? I feel galaxies away from my dissertation research, a thousand miles away from the angst of new and early motherhood, and, currently, a town over from being a woman negotiating for more. Each project feels a bit like the dust from under your back wheels clouding your vision out the rearview mirror. And yet writers should be known for something. Some kind of predictable vein. If Stephen King started writing poetry, would we follow? If Tina Fey started writing romance novels, would we buy them? (To be clear, I would.)

Then the pandemic hit. And my world both came to a screeching halt and ramped up in exhausting ways (I’m an elementary school teacher and full-time cook now!). And in that mix of slow motion and warp speed, I felt my own ability to see my writing career clearly begin to slip away as I worked to learn Eureka Math and what different combinations of cans to dump in the crock pot.

No matter how much I feel the need to write, I often find myself not knowing what to write about. Like the pandemic, I am both empty and full, making it nearly impossible to know what to write next. What kind of writer am I? A humorist? An essayist? A nonfiction writer? A self-help author? A magazine writer? A blogger? My husband always holds my hand when I feel this lost about my writing and simply says: “You write about the human condition.” It’s a beautiful true north, but it doesn’t help me know what to do next. Where to go next. How do I build a writing career in a straight line when I’ve never felt anything but tangled?

For months during this pandemic, I started and stopped dozens of drafts of various projects. So many ideas I had. So many beautiful sentences I had nowhere to put. So many passages I couldn’t bring to the surface. And all that starting and stopping got me was more clutter in my already unruly Dropbox.

And the Dropbox screen—a visual representation of my own messy, undefined writing career—taunted me. So one day, two months ago, while sitting at my desk for the writing time I have committed to every day for the past two decades, I couldn’t go on. I couldn’t figure out what to write. And worse, I feared I had somehow taken the wrong path in writing. Wrote the wrong things. Should have turned right when I turned left. What if I should have been a fiction writer, I thought to myself as tears rolled down. A sitcom writer? A playwright? The great American novelist? And, worse: What if I never publish anything again?

This sadness, this angst, is an occupational hazard, of course. I’ve felt this way before in my writing career, and I’ll sure as hell feel it again. But what I felt more than anything was that I could not see a path forward. Agents, editors, publishing houses—they want to know what you are. What is your brand? What do you sell? And who buys it? The most famous industry question asked is: What shelf does your book sit on? Which is essentially saying: What box does your life fit in? And what if you want to be all over the bookstore? What if customers could find you in the humor, self-help, and fiction aisles? Until, of course, you’re big enough to earn a kiosk in the middle of the store—the sign a writer has ascended all shelves.

I don’t blame the industry. I love the industry. It works hard to get good work out to the masses. When the pandemic hit, book sales reached an all-time high—which is to say, when we are at our most afraid, concerned, and uncertain, we turn to artists and writers. So what happens when the artists and writers feel afraid, concerned, and uncertain?

Well, for this writer, I turned to my Dropbox. If I was going to sit at the desk and stare at the laptop, I might as well organize the damn thing. And so for three solid days, instead of writing, I organized. I did more double clicking, renaming, and dragging things to the cute little digital trashcan than I thought possible. And a funny thing happened as I did all this. My career—my life—started to take shape. Aspects of it started to shift into folders, and those folders started to collapse and be renamed, and that renaming started to spark something inside me—a feeling of pride in what was there, and ambition and energy for what needs to come.

My life, as it turns out, has five main folders: Teaching, Speaking, Coaching, Volunteering, and Writing. And when you click on the Writing folder, it’s as beautiful and mystifying as splitting open the atom. In it, you see a subfolder for Magazine Articles, one for my Blog, one for Books, and one for Plays (I’ve written only one full-length stage play, but adding that “s” gives me the permission to write as many more as I’d like). And finally, a folder labeled Ideas. Double click on that and you are shown a world of possibilities that, when neatly organized, feels less like the messy mind of a writer struggling to find her next piece, and more like the sharp mind of an artist whose ideas are so plentiful they must be thrown into their own folder for another day as she’s too busy writing the current great thing today.

When the organization was complete, I walked across the house to find Jim. He was sitting at the dining room table tending his own work. He looked up and saw my face. “Ooh!” he said, smiling, “That’s the face you have when you’ve finished writing something!”

I shook my head. “No, no writing,” I explained, my expression unmoving. “But I need you to see something, and I need you to understand the weight of it before you do.”

He looked at me quizzically. “So, not writing?”

I shook my head again. “No, but equally important.”

I walked him to my writing desk, sat down in front of the laptop and opened my Dropbox. “Oh wow…” he whispered. “That’s an improvement.” The biggest joy of marriage, to me, is the witness someone serves not just to your accomplishments, but to those things you seem unable to accomplish. Jim has long known about my frustration with my Dropbox. He feels similarly about how messy I let our closet get, but that one doesn’t ever seem to bother me.

“I know it’s silly,” I said, looking at the computer screen with the same loving gaze I gave both my children when they emerged from me in the hospital. “But it’s made me realize something.”

“That tasks we tend to avoid because they seem daunting take very little effort and time in actuality?” he smirked.

I ignored that. “That when you look at all my folders—the dozens of courses I’ve taught and their syllabi and assignments; the speeches I’ve delivered and their accompanying slides; the session notes of my clients and their invoices; and all the board packets and meeting minutes in my volunteer folder….” I paused, looking up at him before continuing, “…the Writing folder is the biggest.”

He laughed and rubbed my back encouragingly. “And so what does that mean for your current writing dilemma?”

“I think my Dropbox was a good indication of how I live my life. Just every day throwing stuff at it as it came to me. An essay here, the first three chapters of a novel there, a new syllabus here, a new speech there. It’s so clear that I’ve never been as intentional as I’d allowed myself to believe I was all these years. I just do as I go and throw it all in together.”

He nodded.

“And when I saw it all organized, I realized something about my writing career I’ve never known before.”


“I’ve been stuck because I don’t know what to make of my writing. I never stopped to realize that my writing has made me. It has not only been my biggest source of professional pleasure during my life...”

I looked back at the screen, files bursting at the digital seams.

“…but when you look at the folder, it’s clear to me now: my writing takes up the most memory.”


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