The Fine Art of Screwing Up

A few years ago a therapist suggested I buy myself a day planner. She argued that having a calendar filled with a list of things I needed to do would help control some anxiety I was having. And for a few years, she was right—I was best friends with my day planner. It was always in my purse, I had tabs on important dates, page-long to-do lists, even a $20 reward if I ever lost it. I wrote down important phone numbers and addresses (in case my phone ever got lost—a wonderful foresight when I left my phone in a NYC cab once), and had every friend’s birthday decorated on a page. College was a breeze with this thing—I knew exactly when assignments were due (which, as a life-long procrastinator, often crept up on me), and I had countdowns to finals. Life made sense with a planner.

And then disaster struck when I got a smartphone.

At first, I expected my life to get easier. I started with an iPhone 4s, and Siri was supposed to be my personal assistant—she’d help me stay organized just by talking to her. A dream of Steve Jobs, I’m sure, but harder to execute in reality. I rarely opened the calendar app (a clunky, annoying piece of technology—adding daily shifts was difficult), and I almost never used any of the reminders (plus, talking to Siri always feels silly). I stuck with my planner, and things stayed strong for a while. Until my old technology and my new technology butted heads. A smartphone made it easier to access data, so I didn’t really need my friend’s birthday’s handwritten anymore. Most of my contacts could save addresses, so the address book at the back of the planner was all but useless (and as my peers moved and married, out-of-date quickly). More and more I’d leave my shifts on post-it notes hidden in my wallet or stuck to the week’s page in my planner, and I’d stick important dates (lunch dates, parties, events) in my head rather than in writing. The whole thing got confusing fast.

When I finally found a great smartphone calendar app (Sunrise) I thought my life would look up again. Finally, everything would be in one place—Facebook birthdays, events, my work schedule, my bills, Gmail invites, Mac Calendars—easy to access and easy to maneuver.

Perhaps I can’t really blame my smartphone. It did its thing well, and for a good while I had my life together. As soon as someone invited me somewhere, I added it to my phone: it’s a date, set in stone, or I guess, set in 1s and 0s. I had all of my work shifts ready on the first day of the week, and I could make plans with just a few clicks. But now that I’ve quit my job, now that I don’t technically need a planner every day, well, it’s a pretty useless piece of technology.

On a whim I am visiting my sister in Cincinnati this week, and already I’ve missed two important dates—two concerts I was really excited to see (Owen Pallett, I’m SO SO SO SO SO SORRY). Because I don’t need to open Sunrise every day, there isn’t any real reason why I would have known about these things. If we’re keeping score, it’s Me-0, Life-All.

I can’t decide what will make me happier. Is having a tight schedule, writing out my hourly to-do lists helpful or cumbersome? Is parsing out my life into chunks ultimately going to give me a sense of control? And how will I find that balance? Should I have it all stuffed into my smartphone, available from anywhere on a moment’s notice? Or is there something true to the idea that writing stuff down really does make it click better? If that’s the case, how does this pocket-sized Moleskine compare to the full-sized one I’ve used in years past?

When I’m organized, I feel great. I feel like I have my life together, there are no big surprises (“we were supposed to hang out, tonight??”). But paying attention to that really does take effort. Perhaps its time I start doing that again, even without a job. I’m pretty sure the anxiety will come down, that’s for sure.

Whatever the answer, I think the key is having everything in one place. Straddling the old and the new has caused me more grief than I care to say. It’s time to either devote to the handwritten planner (and thus a giant purse to carry it in), or to ditch it altogether and accept the changing times.

How do you stay organized? Are you a technology person, or do you stand by the pen and paper method? Let me know!



  1. PEN AND PAPER! Stay true to your craft! I have a small (very thin) planner at work that is not only necessary, it’s essential to my mental well-being. I highly recommend this – even sans-job. There is something so immensely satisfying about crossing things off your to-do list. Even if you are just writing things like “search for new jobs; take a run; buy cat litter,” I find it really helps to have things written down and subsequently, checked off. Because accomplishments.

    1. I make a to do list on a post it note every day at the office. Definitely helps keep me organized, and feels great to check things off at the end of the day

      1. There is a resounding “pen and paper” group. I agree. Writing stuff down is the easiest way for me to keep stuff in my head. Also, you two are dorks, and I love you.

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