Identity

How My Phone Saved Me From Feeling Like a Constant Failure

Making an endless to-do list made me feel like a failure—until an iPhone app helped me see the difference between taking out the trash and tackling my bigger life goals.

by Crissy Milazzo
Feb 11 2019, 5:22pm

Photo by Maggie West.

This Is Fine. is Broadly's weekly newsletter about the previously private and highly personal tactics people use to make the world less harrowing. In this week's newsletter, Crissy Milazzo wrote about the risks and rewards of making lists—and how to do that without stressing yourself out even more. Sign up here to receive a newsletter with a new dealing-with-life strategy each Sunday evening.

I’ve grown to loathe writing personal essays, but I’ve also grown to realize that I’m not decent at doing much else: I started my writing career by working at a sort of content farm, trotting out everything that had ever happened to me in clickbait-y listicle form. 19 Things Sarcastic Girls Say When They’re Secretly In Love With You. 21 Things Girls Hate Doing During Sex. The posts themselves were written to serve their headlines—not the other way around. Heteronormative, thought-defeating, cheap-ass bullshit: That it was.

It didn’t feel good. Even if I didn’t understand every nuance of the insidious, harmless-seeming stuff I was doing, I understood having to consistently perform for a cheap return. As you might expect, I didn’t make good money doing it. I did it for the “exposure.” And, oh man, do I now, all these years later, feel exposed—and not in the good way (if there even is one). It feels obvious to me that I was seeking attention and connection more than I was looking to develop as a writer, or make money, or have a career. (The notion that everyone knew then what I feel like I know now—and that it somehow matters—is the kind of paranoid thought I have to push back by telling myself, over and over, “No one cares.”)

My life became an endless loop of content to generate. Saying “no” was a failure. I put way too much pressure on myself to be A Great Writer and get out of the clickbait swamp, but looking back, I can see that I had no idea what kind of writer I wanted to be, or what I wanted to learn. I had zero patience for my own inexperience. That internalized idea of, I should already be great! made me feel like I was already behind: I felt like I should take every opportunity, and I felt like I should’ve been able to write anything (I couldn’t!), and I needed money, so I tried. I took gigs, I took on credit card debt, I was sloppy, I kept going.

Frantically, I filled notebooks with to-do lists. I’d heard that one way to soothe before-bed anxiety was to write down everything making you anxious in a notebook. So, for most of my adolescent and adult life, I’ve always written down everything bothering me—essentially everything I felt I needed to do in life—before going to sleep. And then I barely slept, and then I looked at the to-do list when I woke up, and then I added more to-dos to the list, and then I didn’t do a bunch of those things, because now there were 37 things, and then I added more so that I could get them out of my head so that I could rest. And then I didn’t rest, wondering, instead, how I could be so stupid, useless, and generally fucking disappointing.

Languish, ridicule, repeat. To make matters worse, I often lost the to-do list itself, causing me to spiral about what both what I knew I’d left undone and all the things I’d never remember. It sounds melodramatic, but it was real to me: My endless to-do list-making was a small, but very telling part of what was making me miserable all the time.

As you might’ve assumed, I had a few other issues to address. This is the part where I tell you that I did not address those issues for quite some time, but that I did eventually. I started going to therapy after a close friend of mine died. Life felt very pointless. That feeling wasn’t new, and I needed to admit that if I was going to continue to live. Through therapy, I realized that I wasn’t uniquely depraved or stupid: Though refusing to see my own self-destructive shit for many years was pretty dumb, it wasn’t special. I learned that what I believed about myself (and the universe) was not only factually incorrect, but was also only hurting me and the people close to me.

One of those patterns was writing down every single thing I “needed” to do. (I’m putting “needed” in quotes because I could barely separate a want or a ‘should’ from a ‘must’.) My therapist usually nudged me softly into reflection whenever I’d mention a task I’d been putting off forever, whether it was writing a book proposal or emailing someone I’d forgotten to respond to eight months ago: “Why is that necessary? Why do you need to do it?”

Every calculation my brain did put every task or desire on the levels of life or death, good and evil: “I need to do the dishes and I haven’t done them, so I am a horrible person and I don’t deserve to eat dinner and I need to write five posts, by the way, because I want to be a writer and I can’t tell you why I want that but if I don’t write the posts now, I am an idiot, and tomorrow I will be more of an idiot and I am behind and I’m awful, is there an event with an open bar where I can go to drink myself into a stupor?” Three years ago, if you described that thought process to me, I might’ve called it “sad,” “loser shit,” or, worse, “fucking stupid.” Now, I’d call it “pretty bad anxiety and depression,” in addition to those things.

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The happy ending is that I’ve found a way to make to-do lists that make sense: ones that don’t equate “taking out the trash” with “determining exactly what to do for money that doesn’t make me feel like a cheap hack” or “apologize to everyone I’ve ever wronged,” etc. I use the Apple Reminders app, which lets you store multiple bullet-pointed lists of stuff. You can attach dates and times to them if you want, which I try to do when it makes sense, e.g., “Pay rent before the first.” When you’re on desktop, you can click, drag, and drop those items from list to list, which is helpful if, like me, you need to sort things out: “to do today,” “stuff I want to get better at,” “things in apartment I need to fix,” “friends I wanna see more,” “health stuff.” The list of lists can go on, but it isn’t never-ending. Maybe it’s just less delusional.

This was supposed to be an essay about how using the Reminders app helped me put space between myself and what needed to be done; how having systems helped me be consistent in having pragmatism and realism in my planning; how being neurotic and self-hating about those things used to feel necessary and now rightfully feels wrong. Once I started writing it, though, it became clear that even my simple use of a simple to-do list app is fraught with all of this Me Shit. It’s infuriatingly personal and simple, all at once. I’m learning to manage that whole to-do.