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January 25th, 2019

Someone recently remarked: “The more often I have plans, the more I realize they don’t work out.”


There is a lot of wisdom in this observation.


At first glance there emerges the simple realization that flexible plans that can adapt as circumstances develop is perhaps indicative of a better strategy.  We might be able to pivot with more agility if our plans are of a shorter concrete nature.  Or rather, our very next action should be as straightforward and definite as possible, but beyond that, our plans should immediately get hazy and more conceptual so that we can integrate whatever feedback that next step yields.  If our plans are too definite too far into the future than we are more likely to ignore feedback from our next step if it is not in accord with those long term designs.  This is how an axiomatic error compounds into a circumstance we have many phrases for: ‘a wake up call’, ‘a slap in the face’, ‘when the bottom falls out’.


We are prescribed by productivity gurus to have definite goals.  This is perhaps poor phrasing because it can easily be misconstrued into ‘have definite plans,’ which is a very laborious process for failure.


What the productivity guru is trying to say is something along the lines of “when you think about going on vacation, make sure you pick a destination!” 


The travel vacation is ironically a very ripe analogy for goal-oriented productivity.  For one simple reason:  what’s the worst part of the travel vacation?  The actual travelling.  Lost bags, delayed flights, cancelled flights, broken down trains, flat tires.  We attempt to plan the travel portion of our vacation like a computer program, where each leg of the journey trips the activation of the next leg of the journey.  We do this so that we can fit the actual travelling part of the trip into a window of time that’s as small as possible in order to maximize the amount of time we spend at the actual destination.  This makes sense in theory, but a walk through the airport any day of the year will evince how often this breaks down in practice.  It’s rare to ask how someone’s vacation went and get the report that the actual travelling part of it was incredibly smooth.


Now compare that somewhat masochistic situation with the opportunity to have open-ended plans?  How often to open-ended plans not work out?  It’s somewhat fundamentally impossible for an open-ended plan to not work out due to the very nature that it’s open-ended.   With such framing, any delay turns into an opportunity to enjoy the current location.  Even an airport can be a wonderful location if we bring along audiobooks or remember we have several dozen hours of podcasts we’d like to investigate, or some writing we could do, or even just sitting and meditating, even if it’s for the first time.  Anyone who has the ability to read or listen to this has the ability to google an introduction to mindfulness and begin developing a new skill.


If we compare both frames of mind, which one is more likely to think themselves…lucky?  Certainly someone who views their life as a series of failed plans is not going to think of themselves as lucky.  But someone who gives up this fear-driven dependence on plans is far more likely to see opportunity in any given circumstance.  Imagine that for a moment.  What if every situation in life suddenly seemed to come ripe with opportunity.  How lucky would you feel?  And yet does it not seem like this is possible if we reinterpret the way that the concept of ‘plans’ effects our life?


While the word ‘plan’ derives from the Proto-Indo-European root pele- meaning to ‘to spread, flat’, which is eventually evocative of the image of spreading a paper drawing or diagram flat in order to see it clearly, it’s worthy to note that it did come through the French language via the word ‘plant’, as in to plant something in the flat ground.


We might ask, do the roots of a plant follow a plan?  Or do they follow an open-ended strategy that changes depending on the soil and circumstance?


Perhaps we would do better to feel our way forward like a plant and plan on no plans.



This episode references Episode 243: Roots, Episode 72: Persevere vs. Pivot and Episode 278: Axiomatic Mistake.

Check out the Tinkered Thinking   Reading List

Dive in to the Archives

Podcast Ep. 285: Plan on no Plans

Tinkered Thinking

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