Is planning counter-productive for certain goals?

In the wake of my Feb 1 realization that I had already missed a resolution milestone, I’ve been trying to figure out how to re-plan and regroup.  It suddenly struck me that one of my big goals was to cultivate mindfulness and stop fretting anxiously about the possibilities of an unknown future.  How do you reconcile those two impulses?  So it was a funny coincidence that an article popped up in my feed about the perils of planning!

There are 3 commonly cited arguments for why planning can be counter-productive. 

1. Planning, more often than not, stresses you out and makes you feel like a failure. 

The famous Zen Habits went from being a goal-oriented productivity blog to a declaration of goal-free living for this very reason.  

But on a more basic level, you just CANNOT PLAN FOR EVERYTHING. I have no idea what my life will be like a month from now, when a newborn baby completely fucks up my daily routine, my meticulously curated Japanese flash cards, and all the beautiful habit chains that I only recently established.  This really really really freaks me out.  I understand though that trying to prepare and plan under a set of rules and goals (I mean, beyond the feed him/ change him/ love him/ don’t shake him etc) will just make things stressful.   

2. Planning misses the point.

More basically, planning is really just our attempt to tidy up our emotional, human unpredictability for neat little concrete goals. In fact, on another favorite blog, Oliver Burkeman’s book The Antidote: Happiness for People Who Can’t Stand Positive Thinking was recently featured.  One argument in the book is that our obsession with goals and planning are really just our way of handling a deep fear of uncertainty. These fail because we artificially try to single out one aspect of our life from the larger picture. 

I’ve been reflecting on this recently too.  My goals are not isolated, singular nuggets of hope for the future but are snapshots from a much messier conglomeration of anxieties, doubts, and dreams.  “Self Improvement” then is always inherently about self-knowledge and emotional management, much more-so than the simple To-Do-List-Building tips or workspace organization. Focusing too much on narrow planning can sometimes miss the forest for the trees.  

3. Planning doesn’t work for creative tasks.

First of all, simple to-do enumeration doesn’t really work for many creative or intellectual tasks.  You can still chart writing times or word count, just to push ahead, but it doesn’t necessarily lead you to something satisfying.  And related to the previous point, if you obsess over a chapter word count then you might forget that the real point is to become an intellectually fecund writer.   

Also, a month or so ago, we had a “distinguished alumni” speaker come to our campus to give a talk.  We were startled to learn that his talk had nothing to do with any of his recently published research but was a brand new topic that he had never presented on, vulnerable and raw and brand new. And much of his talk was done on the fly.  Why?  Because it was an opportunity to push himself forward into uncharted territory, to pry open a neat compact power-point at the seams to discover a totally new beast.  This was something that a respected professor (R.R.) mentioned once –but memorably– in seminar.  Academics in particular are so nervous, so anxious to demonstrate their expertise that they close out ambiguity and uncertainty in their analyses. It kills creative inquiry.


Brain Pickings has probably dozens and dozens of entries that celebrate the value of uncertainty but they haven’t translated into a teachable lesson for me on a day-to-day level. I’m going to sleep on this one and try to work it out over the next day or two.

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