Yesterday, I found myself meandering through my short story file and opening up some titles of work I didn’t recognize to see what they were.

Sometimes when I do this with an archival file of past writing, I find some pieces with hidden sparkle that I’m inspired to work on. But yesterday, several files that I uncovered brought me nothing but embarrassment and a slight tinge of shame. The situations I’d tried to fictionalize were too close to autobiographical for comfort, revealing truths I might have needed to process at the time, but likely did not have enough relevance or context to be useful, insightful, or enjoyable to outside readers.

And since I’m a big “what-if” fantasizer, I couldn’t help but worry about what might happen if somehow, after I was dead, these thinly disguised files were seen by the people involved. I didn’t want to risk being hurtful, especially with no way to explain, apologize, or make amends.

So I did a radical thing. Command A, Command C, Delete. Move to trash.

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Four key strokes. The words were gone, the files disappeared.

And then I worried. Had I been too rash in throwing away my work? Was there something salvageable in these pages I could use later? Was the impetus to toss generated by my (somewhat) objective writer-self, or my condemning inner critic, who probably thinks I should throw away everything?

Too late! They were gone.

And while I’m obviously having second thoughts, I do think it was the right decision, mostly because of the hurtful potential of these particular half-drafted stories. But also because they were all so old, I barely remembered them. And because I really was no longer drawn to write about these things. And if I am in the future, I think the stories will be better served starting afresh with whatever wisdom, perspective, and distance I’ve gained between then and now, enabling me to crystallize the issue and contextualize it in a way where the specific situation and actual cast of characters are no longer recognizable.

When you toss something right away, it’s usually because your inner critic is telling you it’s crap, and we all know how unreliable inner critics can be. So I wouldn’t recommend throwing away anything you’ve written in the last year–or maybe in the last five years, especially with the luxury of fairly unlimited electronic storage. But anything older than that–the choice is yours. Is there anything left in the piece that draws you? And if not, do you want this work to be part of whatever legacy you might want to leave?

So now I’m contemplating what else I should toss. A few months ago, a close friend from high school gave me a whole bunch of letters I’d written to her from the ages of 17 to 23. I read through them all and cringed, even if I could have had more compassion for that young, naive, and giddy girl, who comes off as so darn shallow. My first impulse was to build a fire and ritually burn them, as if putting them in the recycle box wouldn’t be good enough. But instead I buried them under a pile on my desk. A month later, I took more time when I re-read them, and was able to be a little more forgiving of my younger self’s flaws, but I’m still inclined to get rid of them soon–along with most of the contents in the boxes of journals in the attic, and the manila envelopes filled with letters friends wrote to me during my teenage years.

And at some point, I intend to go through more of my old writing and figure out what I want to keep, and what really doesn’t need to be anywhere in the universe, especially with my name on it.

Is it Swedish death cleaning, or more carefully constructing the legacy I want to leave? Perhaps a little of both. And yes, I admit to intentionally wanting to curate a picture of my better self, which may not be the whole truth. But how different is that, really, from waking up each day and trying to be that better self in real life?

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I’ve often joked that I can organize anything–as long as it isn’t tangible.

I’m skilled in creating focused agendas, facilitating unwieldy meetings, planning schedules, and tackling complicated logistics–all with the goal of keeping things on track.

And having spent the day on a variety of editing projects, I again feel thankful for my superpower–being easily able to make a sentence flow more smoothly into the next, and sensing how to move ideas around to create a more satisfying and compelling arc from beginning to end.

But if you dump a roomful of objects on the floor, even with a set of organizing containers from your local big box store, and tell me to put them away in a logical, accessible and attractive manner–I will scream. Or cry. Or both.

So, I understand the sense of overwhelm many writers have when trying to organize their ideas, even if the process comes to me somewhat intuitively–if not in the first draft, than usually in the beginning stages of revision. Yet, my empathy is not going help those who feel strangled by the vines in the jungle of their unruly mind, as I learned quite humbly, during all the years I worked in a university, attempting to “teach” students the basics of coherent and engaging writing. It’s still a struggle to break down the process of organizing ideas (or anything I do intuitively) into small replicable steps. And it’s even harder to think about how to do this for poets, fiction writers and CNF writers, whose projects depend on a certain degree of unbridled creativity. But here are some things I’ve learned from being in the trenches. I hope they’re helpful:

(1) When generating material, always trust your “wild mind,” and let the ideas flow where they will, even if you don’t immediately sense the connections. There will be plenty of time to rope in (or eliminate) tangents later. And the relationships between things you uncover will surprise you–in a good way.

(2) Don’t self-censor while you are drafting. Sometimes I’ll get to a place and think, I really don’t want to write about that. This could be because it’s irrelevant, too revealing, unpleasant, silly, emotional, etc. But even when I don’t use these blips of material, they often serve as a bridge to the real thing I want to write about. If I don’t let myself build that bridge, the seed of what really matters to me will never sprout.

(3) Once you have your generated material, be playful with it. Feel free to eliminate whatever you want (ideally without judging that material as “bad,” just not needed) and take time to rearrange what’s left several different ways, adding whatever you think needs more context, clarity, or overall “oomph.” This is the time to start thinking about flow and what’s holding the piece together–i.e. what you really want to write about, and the various ways you can get from the beginning of your writing path to the end.

(4) After you’ve done this a couple of times (or perhaps before Step #3, but definitely not before generating material), it may be time for an outline, especially if you have a longer project. For me, it helps to think of an outline as an aspiration and a way to help grasp “the big picture,” rather than as a directive from my inner dictator. This helps me deviate from and then revise my outline as much as necessary, or disregard it entirely once I know where I’m going and feel confident I can get there without it. (Yes, I am one of those people who often turns off the GPS!)

(5) Going through Step #3 several times–with or without an outline–will likely lead to even more cutting and rearranging, and you may be faced with eliminating a line, an image, or even a whole paragraph or several pages that you really love. It’s a writer’s curse–the idea that you have to “kill your darlings,” a phrase that has been attributed to Allen Ginsberg, William Faulkner, Stephen King, Oscar Wilde, Eudora Welty, G.K. Chesterton, and Chekhov, but was likely coined by the lesser known writer Arthur Quiller-Couch in 1914. But you don’t really need to “kill” those precious bits. Just give all the darlings a good home in a separate file on your computer to be potentially resurrected in another piece. Many of them may never see the light of rebirth, but they’ll still be in your files, and perhaps when you die, your archivist will discover all those unpublished little gems!

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But seriously, what I think is most important here is to have faith that you can get from Point A to Point B, even if you’re not confident in your sense of direction. It just may take you a little longer to find the path. And if you do get lost, make sure to enjoy the walk, rather than worry too much about where it’s taking you.

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