PLANNED MEDIOCRITY: THE BENEFITS OF ORGANIZING INTENTIONAL IMPERFECTION

Every day people struggle to get to the gym. They look in the mirror and sigh, hoping that their sweat and tears finally etch themselves onto their body. Is that an ab line, or just a hope of one?

Imagine instead if you knew that it took 10,000 crunches to gain a 6 pack. Or if you needed to deny 230 urges to become a non-smoker?

Feels more manageable, doesn’t it?

WORKING PROFESSIONALS

My partner Lydia has always been an organizer. And that’s a good thing - as a Senior Editor at USA Today’s online travel site 10 Best, and the production manager for their Readers’ Choice Awards, she’s got a lot on her plate. The Readers’ Choice is a national award that’s highly sought after. Cities have written articles and put out TV ads to help turn out votes. She’s responsible for promos, newsletters, producing YouTube videos, contacting experts, sourcing photos, updating PR contacts, assigning articles, weekly strategy sessions, and writing articles herself. In her spare time, she writes for another publication, is an officer in the Society of American Travel Writers where she helps organize conferences, and volunteers as a Crisis Text Line counselor. 

She does all of this, week after week, seated next to me as though it’s nothing. It is mind boggling.

For her, organizing is a necessity and one that gives her “control over the chaos.” Which makes sense on many levels. In one study on sleep hygiene, writing tomorrow’s to-do list actually helped off-load worry, helping subjects sleep better. Her Sunday planning session is a relaxing ritual.

When things are finite, long-range planning like this allows you to measure the void.

The so-called “hardcore” or “pragmatic” dharma movement applies similar approaches to Buddhist meditation. According to them, practitioners tend to get lost, floating around for decades without any real progress because no progress is ascribed. While they may come and do the work, forward momentum is never quite reached. It’s a feeling I’ve likened to churning in the mud. Lots of daily work is done, but the percentage towards completion isn’t ever clear. And so completion may never come.

This is the opposite ethic of true working professionals.

The high mark of mastering a craft means delivering products on a schedule. Most experience this in tasks with clear objectives, those often handed down by bosses in normal jobs. But it starts to disappear once things get vague - like in the arts, with self development, freelancing, getting in shape, or with writing.

The process writers tend to emphasize deadlines. Legendarily productive science fiction writer Brandon Sanderson does this visually with percentage bars at the top of his site. They clearly denote how far along he is with drafts, outlining, or proofing. Writing author and teacher Holly Lisle can estimate with high accuracy when she’ll complete a novel. She writes everything, as writing coach Donald Murray would describe, “to deadline” by measuring, with buffers, how long projects will take.

George R. R. Martin, on the other hand, has famously had problems with this over the years. 

In an interview with Stephen King, this difference becomes clear.

“How the fuck do you write that many books?” Martin asks. “I’ve had a really good 6 months [and] I’ve written 3 chapters and you’ve written 3 books in that time!”

King responds that he tries – despite entropy and real life intruding – to get 6 pages done a day, no matter what. And he sticks with it.

While George and I aren’t on par as writers – I find him to be an amazing one – I do get how he feels. Unlike Lydia, I’m not a natural planner, nor was I forced to be one. This seeps into almost every aspect of my life - from writing to travel planning. And while this suggests a certain freedom, it really means that I feel I’m running around with my head cut off most of the time. There’s a panic that no matter what I do in a day, it will never be enough. I just have to blindly (and rather hopelessly) march on and on.

What Lydia advises is to write down all tasks and break them into components. Estimate a time for each task, then estimate a timetable for them using a basic understanding of how you work in a day. Include flex time. Include additional tasks if you exceed expected deadlines. And adjust timings as you get a better grasp of how long they will take across projects.

She helped me to do this with the massive task now in front of me - a book proposal. The first proposal I completed was excruciating, taking 9 months to complete. I didn’t know what to do at all.

This is my third or fourth proposal. I know exactly what needs doing, and thanks to process writing, I know how to do it. And yet, it still feels equally uncertain. I can’t answer basic questions regarding a timetable. And it feels like it will last forever. And when I switch tasks, I feel totally lost.

I broke up everything with her help, overestimating the amount of time for each task, using my 20 minute Pomodoro sessions and deep focus protocol.  Of course the calculations will be off the first time, but when we inputted a buffer, took out weekends and my upcoming birthday this massive, behemoth task ended up taking…16 days.

I’m still stunned.

Why haven’t I done this before? 

INTENTIONAL IMPERFECTION

Backing up a moment into theory, I initially thought that creating “Finiteness” – therefore predictability in long-term goals – might be another Element of Change. It allows our minds to grasp and lock on to discrete things. In that it’s similar to metrics. This “chunking” bakes in the pressure to actually complete the task in the requisite amount of time - and try to beat it. It’s an odd sense of gamification and self-competitiveness that all good metrics encourage. 

If I were to think of it as another combination of elements it would be:

Intentional Imperfection, or “shittyness” is the element I ended up adding to the Elements of Change. Anne Lamott includes a chapter in Bird by Bird (her book on writing) on “Shitty First Drafts”. I am a huge fan of this concept. Like Tiny Behaviors, which drop quantity, Intentional Imperfection harnesses lowered quality to gain consistency. By creating a System of preplanned (Bypassing Decisions) Tiny Behaviors that you can define Metrically, you gain Momentum. Writing down what you need to do (Implementation Intention) and planning on less than optimal times for task completion (Intentional Imperfection) you suddenly have the ability to plan in advance. Adding a system of check marks or progress bars can act as a Reward.

Just the idea of such a timetable seems eminently relaxing. It makes me want to trust the process more when there are not only waypoints and progress reports but an end clearly in sight. The giddiness of seeing that number – 16 days – is unparalleled. And it doesn’t derive simply from making molehill out of a mountain. It frees me up to plan 3 or 4 steps down the line instead of hoping and praying that the task in front of me actually gets done. This also builds in the pressure to conform (Conformity is another element I’ve thought about adding), so that I can actually do the next step. I’ve always wondered how freelance writers could pitch an article about an event months in advance, and also take into account a 3 month lead time for publication after submitting the article. 

I guess that’s called “strategy”.

As with all elements or new techniques, I like to see how they can be applied to other processes. With eating well, like with writing and meditation, it would be great to actually create a map of mastering eating based on the research I’ve done on quitting other habits. Financial planning in long-term steady investment strategies like the Bogelhead philosophy, gifts predictive power - rather than hoping you’ll be rich or poor if your investments fluctuate, you know how much money you’ll probably have in X number of years. For body building it’s macrocycles - being able to shift from bulking to cutting and knowing when to do it.

I have never used planners. And anytime I’ve attempted it I’ve abandoned them in short order, just like with habits as a kid. It’s almost like I grow bored or forgetful of them. Lydia believes this has to do with confronting fear. She says with planning you have to write all the things you have to do up front, and that idea is something that engages all my well honed avoidance measures. But she thinks it will ironically result in the greatest LOSS of fear in my life. When I wondered out loud how I could could counter that avoidance she gave me a measured look as if to say …isn’t your whole project about habits? Have you ever made a habit of this?

The obstacle is the way and the only way is through.

PLANNED MEDIOCRITY

I have already fallen far behind the mark of 16 days. I think the biggest reason why is that I wasn’t planning for the less than optimal. And I think this is the key to the entire process, and why I’ve always abandoned planners. In the past, I used planning as a visual intention of optimism. I COULD get everything done by next Thursday. If I put maximal effort in, I COULD finish my project TOMORROW. When I inevitably failed at the task, the next ones I had lined up collapsed, as did my adherence to the planners.

As with Tiny Habits and lowered minimums, planning for under average performance nets greater gains through predictive power and consistency.

At some point I will have to sort out a planner. Lydia tried the Savor the Success Planner from Angela Jia Kim. She didn’t like it as much because it had too many bells and whistles and was too zoomed in on each day. But I like how Kim includes the 3 Ships concept from Chellie Campbell’s The Wealthy Spirit. This is particularly helpful for entrepreneur’s (whom the organizer is geared towards) and could be adapted easily to people who are pitching, like me. Lydia settled on the Ink + Volt planner, which she has been using for at least 4 years. She likes that it is relatively minimalist and has a built in revisiting of yearly and monthly goals.

Whatever the planner, the important thing for me is to formalize a planning habit. As I mentioned before, for Lydia this involves a Sunday morning ritual with coffee, writing a to-do list for the week, first of repetitive tasks, and then adding others, including anomalous events.

As a skeptic and cynic, depressed and anxious, the horizon has always held a vague sense of potential menace, just waiting to be unleashed. But Lydia’s planning, with all of its progress bars and completion times, is a tool to chop and dice the infinite. And for once I feel oddly relieved.

photocred: planner by Duc Ly, chess by Tristan Martin