We seek self-improvement in many areas:  in physical fitness, language proficiency, travel,  stimulating intercourse with women, professional advancement, and in growth of character and worldly wisdom.  Our premise is that development in all these areas makes us better and more successful men.  It is relatively simple to measure our progress in the first five areas I have just listed.  They are readily quantifiable fields of endeavor.  Years ago, when I wanted to maximize my score on the Marine Corps physical fitness test, for example, I would work towards running three miles in eighteen minutes, doing eighty sit-ups in two minutes, and doing twenty pull-ups.

But how is it possible to “measure” our progress in developing character and wisdom?  Is there any meaningful metric that can be used?  The question is an important one.  Without some method of regular self-examination, we will inevitably make things easier on ourselves; we will  slide into complacency.  Advancement will come to a halt.  We will become like the weight-lifter whose progress has reached a plateau, and then just fizzles out.

There are some signs that can be used as indicators of progress in worldly wisdom.  If you are aware of what they are, you will be more likely to notice them.  As you continue your humanistic studies, and (more importantly!) the flesh-and-blood school of hard knocks, you will begin to notice one or more of the following signs of maturing wisdom.

You begin making regular contributions and additions to your philosophy of life.  Wisdom accretes slowly, like mineral formations building slowly in a cave from the steady dripping of water.  As the poet Hesiod says in Works and Days (361-362):  “If to a little you keep adding a little, and do so frequently, it will soon be a lot.”  You build your house of wisdom slowly, one timber and one shingle at a time.


You begin to notice connections between things (ideas, places, personalities, emotions, etc.) previously not perceived.  Increasing wisdom and virtue opens doors of perception that were previously closed.

You begin to lose enthusiasm for being around people without ambition or purpose.  Abandoning people or things that add no value to your life is an important step in forward progress.  Keeping company with dullards, fools, and dissolute people will bring you to ruin sooner or later.

Depressions of the mind or spirit become less frequent and more tolerable.  The philosopher Plotinus, seeing that his pupil Porphyry was suffering from extreme depression, encouraged him to take an extended vacation in Sicily.  The change in routine did him wonders, and accelerated his forward progress in Neoplatonism.

You are less and less disturbed by the foolishness, absurdities, and cruelties of the world.  A major sign of progress is to maintain one’s calm in the face of the avalanche of nonsense which the world throws at us.  I confess I need much improvement in this area.

Your style of discourse (in speaking and writing) begins to change.  Refinement will inevitably become a feature of your discourse.  As the gem becomes more polished and cut, it gleams more brightly.

You begin to lose your inflexibility in holding on to your cherished beliefs.  What we once saw as doctrine, we begin to see as only one perspective.   Certainty is the mark of a closed mind, and is murderous.  The key lesson of philosophy is perspective.

You no longer feel the need to convince or convert people to your position.  People will arrive at the truth in their own time, and on the backs of their own horses.  Losing an argument or debate with another man will mean nothing to you.  Aristippus, after being verbally lashed by another man, said “I who have been beaten in an argument will have a better night’s sleep than my victor.”


You become less governed by your passions, and more governed by reflection and reason.  Unformed spirits are slaves to their fear, greed, envy, and rage.  As a man makes progress in acquiring wisdom, he shifts his focus from the baser passions to the milder, less serious ones.  Advancement of wisdom takes the edge off the destructive passions.  Consider what the humanist Francesco Filelfo (Letter to Poggio and Valla, 1453) said about the destructive power of excessive passion:

We do in fact commonly abandon reason from time to time and freely follow our passions.  This often happens when we are taken in by the advice of friends who secretly hate us or are out for revenge for themselves:  they goad us to fury, bringing us to such heights of passion that we upset all laws human and divine…Can there be any injury so grave as to drive you mad?  For the man who lies is mad enough.  This surely is the nature—the violence, the rage, the fury—of a troubled soul, that it knows no restraint…For as long as a man is deprived of reason’s light, he perceives nothing clearly and judges nothing rightly.  So it comes about that he is as one walking through deepest shadow, his road before and behind, his very destination unknown.

You become more focused on action, and less focused on excuses.  The wise man knows that nothing in this world is attained without effort and struggle.  He spends less time in fantasy, and more time in execution.

You begin to seek out other wise men and value their company.  As Plutarch says, “And a young man improving in character instinctively loves nothing better than to take pride and pleasure in the company of good and noble men…”


You become more focused on attending to details.  Carelessness and frivolity are feminine traits.  The wise man, who seeks progress through study of philosophy, will begin to realize that this world is a serious place, requiring a certain sense of sobriety and application.  The responsibilities of life should be embraced, not shirked.

You begin to see the unity of all things, and the love of this unity growing within you.  As the great Nicolas of Cusa says (Sermon 144),

Love turns into devotion by way of love, so that it is dissolved in tears.  For it is like a fire that is applied to green wood, which burns one part while leaving another moist.  Thus does love act upon the frigid soul…Therefore, love is the cause of order.  When it ceases, order does too.

You become more and more drawn to the study of philosophy.  If you care about the world and about yourself, then you care about philosophy.  Its study will raise you to heights undreamed of.  As Valerius Maximus says, in a brilliant aside in his Memorable Doings and Sayings (III.3):

There is another strong and resolute soldiering of the spirit, powerful through letters, priestess of the venerable rites of learning:  philosophy.  Once received in the heart, she drives away every unseemly and useless emotion, confirms its entirety with the bulwark of solid virtue, [and] makes it more powerful than fear and pain.

There is an inescapable balance in life.  The more difficult a goal is to achieve, the more worthwhile it will be.  Acquiring worldly wisdom is the most difficult of all.  You will mostly feel lost, bewildered, and confused.  You will often feel like abandoning the pursuit altogether.  But even in these moments, remember that you are progressing, even if you believe you are not.  Watch for the signposts on the road, as I have listed them above, and continue on your journey.  Allow others to help you.  As the great humanist Lorenzo Valla said, “To take pleasure in the success of the good and the wise falls only to the lot of one who is himself good and a lover of wisdom.”

Read More:  The Life Of A Location Independent Traveler


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