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What Wisdom Requires
The Five Whys
Welcome to The Stoa Letter, the newsletter on Stoic theory and practice. Today’s letter is from Michael Tremblay – taken from his new course in the Stoa app Be Wise.
🏛️ Theory
There is an exercise in design thinking, the field dedicated towards creative solutions to novel problems, called the 5 Whys.
To do the 5 Whys, when encountering any problem we always ask why it is happening at least five times, almost like a young child does.
A common example involves a local government frustrated that a symbolic statue is constantly dirtied with bird droppings. They want to know how to stop this problem.
So you ask why is it covered in droppings? Because there are many birds around it.
Why are there so many birds? Because they swarm the statue at night.
Why do they do that? Because there are many bugs at night they like to eat.
Why are there so many bugs at night? Because we shine lights on the statues at night that attract the bugs.
Why do we shine the light? Because we want to make the statue visible.
By doing this exercise, a new context is revealed. The real question is not how do we remove the birds, but do we have a better way of making the statue visible at night or is it worth the bird droppings to keep things how they are?
This is an example of a wisdom exercise. One the Stoics would connect to the sub-component of virtue called situational awareness.
Situational awareness is about understanding the context of things.
Consider the example of a boss with coworkers fighting, Alex the more senior and Jaime the more junior. A wise choice here makes all the difference in a happy workplace.
Right aim is the target. The Stoic would aim at being a good boss. Achieving the right outcome to fit that role.
But you can’t hit your target or aim without understanding the situation.
Situational awareness is the next part of living with wisdom.
Is there a history here you were missing? Are people telling the truth? Is there something in the way the work is set up that makes their jobs conflict with each other?
These are the kind of questions we must ask and answer in order to understand the circumstances we face.
Marcus was Emperor of Rome. He encountered situations much more complex than Jaime and Alex’s fight. Marcus praised this quality of situational awareness in his adoptive father, saying that he admired:
His searching questions at meetings. A kind of single-mindedness, almost, never content with first impressions, or breaking off the discussion prematurely.
Consider how to be more like Marcus’ father in your own life. Never satisfied with first impressions, when presented with a conflict you would seek to understand what is really going on. You would gather information from both sides, compare conflicting stories, and question your own assumptions about what needs to be done.
Be like Marcus’ father. Don’t be content with first impressions. Always be searching. Understand what is happening and why.
🎯 Action
Pause today and perform the 5 whys exercise.
🔗 Links
We just launched a new set of routines on Wisdom in the Stoa app. Download the app here (if you haven’t already).

As always, if you truly cannot afford the app, but want to continue using it. Send us an email and we will set you up.
What parts of Stoic wisdom do we most need today? |
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