How to Approach Paradox

Shawn Steggink
6 min readNov 3, 2020

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Maybe this is far fetched, but imagine you’re graduating college and applying to jobs in the middle of a global pandemic.

A dynamic you’re likely to run into is that many of these jobs require experience, but how do you get relevant experience without first having that job? This example may be a modern problem but the underlying need to navigate contradictions in a complex world has been contemplated by philosophers for thousands of years, stretching back at least to Heraclitus, a thinker from the 5th Century BCE. Clearly, there is something important to understand about these dynamics.

Although frustrating, contradiction is often a signal that you’re close to something fundamental about life. To fully understand it, you must learn to hold contradictory concepts in the mind simultaneously.

Let’s illustrate this by breaking down a few examples.

Idealism vs Pragmatism

These are two extremes with respect to how people orient themselves in a complex world. On one end are those who subscribe to their values and ideas about how the world should be without much regard to how the world is. These people often don’t succeed in life since success requires a more robust connection with reality.

On the other end are people take rules, customs, and traditions at face value rather than evaluating their worth. Although often successful in life, these people can reach a psychological breaking point since their values are not reflected in how they orient themselves in the world.

So how do we integrate these opposites? Consider what we’re doing in each moment as we think, perceive and act in the world: We’re continually building a picture of reality, forming beliefs, expectations, and desires based on our experience, to inform our actions. Which is to say that when we perceive through our senses we revise our mental model of the world and when we act we mold the world to our picture of it.

The problem arises when we identify too strongly with one of these worlds by ignoring feedback from reality or refusing to question it. There are no final versions of either so we must accustom ourselves to the process of living at the frontier between them. Doing so creates space for something greater to emerge than what you expect of the world or what the world expects of you.

Act Boldly or Prepare

Let’s say you’re debating whether to get a job or go to school. You’ll get contradictory advice depending on who you ask: some say you should simply dive in and learn by doing. Others say you must spend time sharpening the ax. So what to do?

First, let’s consider a poem, called “The Bell and the Black Bird”, by David Whyte encapsulating this dynamic.

The sound of a bell
Still reverberating,
or a blackbird calling
from a corner of the field,
asking you to wake
into this life,
or inviting you deeper
into the one that waits.

Either way
takes courage,
either way wants you
to be nothing
but that self that
is no self at all,
wants you to walk
to the place
where you find
you already know
how to give
every last thing
away.

The approach
that is also
the meeting
itself,
without any
meeting
at all.

That radiance
you have always
carried with you
as you walk
both alone
and completely
accompanied
in friendship
by every corner
of the world
crying
Allelujah.

The bell is a “call to prayer”, an invitation to silence, to depth, to another context beneath the context that you’ve established in the world. This is seeing your circumstances with new eyes, framing things differently, understanding yourself and reality more fully. It’s getting another degree before entering the job market.

The black bird represents the call of a new life, or of reality just as you find it and just as it finds you. This is seeing new things with the same eyes, it’s getting a job rather than a degree or playing rather than practicing.

So which call do you heed? Let’s zoom out by imagining your life on an X,Y axis with the X-axis as time and the Y-axis as action (above zero) versus study (below zero). As you progress through life you’ll notice a pattern emerge: you never really stay above or below zero for long. You inevitably cycle between preparing (lessons from parents, schooling, informal education) and acting (play, internships, jobs).

What this means is that when you are confronted with a choice between a new life and deepening into your current circumstances you should account for where you are in the cycle.

You must because these phases feed off of each other to produce value: introspection is only useful if you have raw material to work with from interacting with the world. Similarly, you must spend time in introspection to process and integrate raw material to thereby show up for others as your most powerful self. Resisting or ignoring this natural cycle leads to burnt-out and boring one-dimensional people. You know the kind.

Relativism vs. Absolutism

This paradox has been debated since at least the time of Plato. The Platonic conception is that there are absolute and timeless forms of things inhabiting a plane of existence not bound by space or time. These things include numbers, gods, and morality and are accessible to us through rational thought.

The other school, begun by Plato’s student Aristotle, considers things relative: all we can ever know about truth boils down to the evidence presented to us. Therefore, we can never know anything for certain since it’s impossible to have truly complete evidence. Truth, then, is relative to your experience — what is good or true for me isn’t necessarily good or true for you. Anything goes.

The workaround here is to instead consider the range of contexts in which things are true or useful. To do this consider two contexts on opposite ends of the spectrum. On one hand we have individual preferences, such as things I consider fun or not. These are true for me but break down as soon as we leave the context of my body.

On the other we have the laws of physics. These seem to hold universally: across planets, solar systems, galaxies. However, even physical laws have only been observed in a specific context: from our little planet using mammalian mental machinery while the universe is expanding. We have no idea if these rules would hold up if the universe stopped expanding, for example, all we can say is that we haven’t disproved them yet.

In any case, the laws of physics are consistent enough to make them highly useful leading to this insight: the probability of something being true is all that matters, not whether it’s universally true. And that probability distribution depends on the range of contexts in which something is useful.

We can be pretty confident that physical laws will hold in all of the contexts we are likely to encounter as a species. The truth of other things, like opinions or moral imperatives, depend on their context which also means that some opinions and morals are more “true” than others. There are more contexts in which stealing is acceptable than murder, for example.

So, when establishing the truth of an idea or the benefit of a proposal you should consider the range of contexts in which it would hold or prove beneficial, and how that answer relates to you and your goals specifically, rather than getting tangled in abstractions.

There are two themes that surface as we consider how to address paradoxes. First, the way forward is almost always to hold contradictory concepts in the mind simultaneously by zooming out to see the larger picture. Doing so allows you to see the subtle links between opposing ideas.

However, seeing the larger picture is only helpful if you know how it applies to your situation. And that is the second and more important theme: in order to resolve paradox and complexity, you must heed the oldest advice in the book: know thyself.

Only through self-knowledge can you understand where you are in life’s cycles and how to best engage with the world around you. Strategies for doing that will be the subject of a future article.

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