A Woeful State of Planning

I have a problem with planners. Last year I purchased three, and none during Planner Season (November through January), when one has their pick from a bounty of pre-dated agendas that make you think: Yes, now I can confidently conquer this calendar year and emerge a better, more goal-oriented version of myself.

I waited until March, when all that’s left is florally bullshit or planners with no dates. Obviously, I opted for the latter.

The first was a 5×8, teal specimen made by Ardium. I probably fell victim to a facebook ad in a moment of organizational vulnerability and was appropriately punished for my spontaneity: the Ardium was charming, but too stiff. It wouldn’t stay open on its own, which made it challenging to do all the tedious writing-in of dates required in a dateless calendar. I used it for three weeks. It had to go.

The second was a Passion Planner, which I read about on Esmé Weijun Wang’s blog. It was stunning: large, pliable, strategically interspersed with goal-setting guides that would naturally stand in as life coaches, zapping me throughout the year with volts of inspiration. At the back, a stack of crisp, blank grid paper waited to be messily polluted with ideas. I made lists of albums I wanted to buy, sketched the blueprint of a coffee table I’m unqualified to build. From April to September I carried the Passion with me everywhere until one day at Barnes and Noble I spotted a

Red Moleskine Pocket Planner. I’ve always wanted to be the kind of person that keeps a planner in the back pocket of her jeans! And a red one, no less: a color that would fool strangers into thinking I’m more exciting than my wardrobe suggests. I used it for exactly two months because tiny planners are meant for tiny people with tiny ideas and I am neither.

Disillusioned, I went back to the Passion. It made the most dimensional sense, and also I couldn’t live with having wasted upwards of $70 on planners I didn’t use. The benefit of a dateless planner is that you can break from it for any length of time and have wasted no space. The dateless planner is like an obedient dog waiting outside the convenient store while you decide whether fingertip Bandaids are worth the extra two bucks (they are). The dog doesn’t care; it’ll be there waiting when you come out with your fancy butterfly bandages.

The planners of my past faced much less scrutiny. Aside from a diehard At-A-Glance phase, I have often used whatever planner was supplied to me by an educational institution. The last planner I purchased before this period of turbulence was a sort of travel-themed chunky number with little sketches of bicycles throughout; I decoupaged its mediocre cover but over time grew fond of its cutesy insides with their quotes about wanderlust. I used it to capacity and even got a little sentimental at its passing.

Here’s what I think changed: most planning has moved to the web. My work meetings appear on a dreadfully utilitarian Outlook calendar, my personal stuff on Google, and local events stay in Facebook, where I will be periodically reminded of their impeding occurrence. (“Why don’t you just put everything on your Outlook calendar?” my boss asks. I look at her as though she has asked why I don’t buy a pair of velcro power-walker sneakers.) I balk at web calendars but keep them active because, as a person existing in whatever this era is called, that is expected of me. By this point I should have distilled all matter of my existence into one device that never leaves my person. Its constant companionship provides me with immediate access to meeting times, phone numbers, birthdays, recipes, library due dates, and lists of whatever junk I currently need from Target. This is, admittedly, convenient, but also epically dissatisfying and un-fun.

And—cloud or no cloud—I’ll never believe the stuff of my phone has any degree of permanence.

But this is not quite about my luddism. On a luddism scale of 1 to 10—one being the kind of person with a smart doorbell and 10 being that guy who lived in isolation in the Maine wilderness for 27 years—I’m somewhere around a 6.5.  I own a smartphone, but won’t use Siri. I’m appalled at the discontinuation of things like the headphone jack and the optical disc drive. The thought of getting an entire uncooked meal delivered to my door feels no different than paying a homeless person to shine my shoes. And I just referenced Siri though have no idea if that software is still relevant or if it’s even referred to as “software.”

This middle-of-the-road modern luddism is not a simple curmudgeonly refusal to embrace new technology; it is a terrible in-betweenness, a sticky tar of romance and nostalgia. I buy into specific technologies when it becomes clear that it is harder not to, but until then, I exist in this liminal space darkened by the presence of useless objects whose former relevancy lingers like a sad ghost.

The planner, I suppose, nearly lost its place in the hierarchy of needed objects but was resurrected, much like vinyl, by those of us unwilling to accept its ruin. It has been reimagined as something artistic and inspiring and fun, like that cool girl you meet at a party who wears overalls and plays clarinet in a marching band (consequently, this was me at 13, and back then it was far from cool—what changed???). Planners are a quiet riot against the onslaught of digital organization, a reminder that crossing things off an actual list will always be more satiating than its modern counterpart. (If you’re not convinced just watch this FUN VIDEO.)

And yet, I am still woefully dissatisfied with the state of my planning. Given that plans predominantly come to being on the web, maintaining a planner is now a chore of copying things into reality. I prefer paper but also prefer a life in which I don’t have to work so hard to exercise this preference. My struggle to find the perfect planner is actually a struggle to deny the planner’s evolution, to stave off a future in which planners go the way of 35mm film. This will be a sad, colorless time built on the precariousness of a digital fantasy.

In the meantime, I return to my Passion Planner and its tangible heft, its expansive white spaces hungry for my ink and my dates and my ambitions. If I forget to update it, I write reminders on post-its that I stick to my laptop. The whole cycle is a masterpiece of mixed-media, guiding my voyage through whatever this era is called.