Summary
Seneca writes to Lucilius about defending a friend who has chosen retirement over climbing the career ladder. People are calling this friend lazy and a quitter, but Seneca argues he's made the wisest choice possible. Prosperity, Seneca explains, is like a violent storm that tosses people around, driving some toward power, others toward luxury, puffing some up and completely draining others. Those who seem to 'handle success well' are just like people who can hold their liquor—it doesn't mean the alcohol isn't still poison. The friend who chose retirement is like wine that tastes harsh when young but ages into something magnificent, while the people-pleasers are like wine that tastes sweet at first but turns to vinegar with time. Seneca emphasizes that now is the perfect time for this friend to learn and grow, not the surface-level knowledge you sprinkle on yourself at parties, but the deep wisdom that soaks into your bones. The ultimate skill to master? Contempt of death—not because death is good, but because fearing it makes you a slave to everything else. When you stop fearing the worst thing that can happen, you become truly free. Seneca points out that even children and people with mental illness don't fear death, so surely rational adults can learn the same peace of mind through wisdom rather than ignorance.
Coming Up in Chapter 37
In the next letter, Seneca explores what it means to make a promise to live virtuously and why breaking that commitment to yourself is worse than defaulting on any financial debt. He'll reveal why your word to yourself is the strongest chain that binds you to wisdom.
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An excerpt from the original text.(~500 words)
L←etter 35. On the friendship of kindred mindsMoral letters to Luciliusby Seneca, translated by Richard Mott GummereLetter 36. On the value of retirementLetter 37. On allegiance to virtue→483005Moral letters to Lucilius — Letter 36. On the value of retirementRichard Mott GummereSeneca ​ XXXVI. ON THE VALUE OF RETIREMENT 1. Encourage your friend to despise stout-heartedly those who upbraid him because he has sought the shade of retirement and has abdicated his career of honours, and, though he might have attained more, has preferred tranquillity to them all. Let him prove daily to these detractors how wisely he has looked out for his own interests. Those whom men envy will continue to march past him; some will be pushed out of the ranks, and others will fall. Prosperity is a turbulent thing; it torments itself. It stirs the brain in more ways than one, goading men on to various aims,—some to power, and others to high living. Some it puffs up; others it slackens and wholly enervates. 2. “But,” the retort comes, “so-and-so carries his prosperity well.” Yes; just as he carries his liquor. So you need not let this class of men persuade you that one who is besieged by the crowd is happy; they run to him as crowds rush for a pool of water, rendering it muddy while they drain it. But you say: “Men call our friend a trifler and a sluggard.” There are men, you know, whose speech is awry, who use the contrary[1] terms. They called him happy; what of it? Was he happy? 3. Even the fact that to certain persons he seems a man of a very rough and gloomy cast of mind, does not trouble me. Aristo[2] used to say that he preferred a youth of stern disposition to one who was a jolly fellow and agreeable to the crowd. “For,” he added, “wine which, when new, seemed harsh and sour, becomes good wine; but that which tasted well at the vintage ​cannot stand age.” So let them call him stern and a foe to his own advancement. It is just this sternness that will go well when it is aged, provided only that he continues to cherish virtue and to absorb thoroughly the studies which make for culture,—not those with which it is sufficient for a man to sprinkle himself, but those in which the mind should be steeped. 4. Now is the time to learn. “What? Is there any time when a man should not learn?” By no means; but just as it is creditable for every age to study, so it is not creditable for every age to be instructed. An old man learning his A B C is a disgraceful and absurd object; the young man must store up, the old man must use. You will therefore be doing a thing most helpful to yourself if you make this friend of yours as good a man as possible; those kindnesses, they tell us, are to be both sought for and bestowed,...
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Intelligence Amplifier™ Analysis
The Road of Strategic Retreat
Society punishes those who refuse to play status games, but walking away from toxic competition is often the wisest choice.
Why This Matters
Connect literature to life
This chapter teaches how to recognize when society punishes strategic retreats while celebrating self-destructive advancement.
Practice This Today
This week, notice when someone gets criticized for setting boundaries or choosing stability over status—ask yourself if they might be the only one thinking clearly.
Now let's explore the literary elements.
Terms to Know
Retirement (in Stoic context)
In ancient Rome, this meant stepping back from public office and political ambition to focus on philosophy and personal wisdom. It wasn't about age or stopping work—it was about choosing inner development over external status.
Modern Usage:
Today we see this when people leave high-stress corporate jobs to teach, start small businesses, or prioritize family over climbing the ladder.
Career of Honours
The Roman political ladder where men competed for increasingly prestigious government positions. Success meant wealth, power, and social status, but also constant political scheming and public pressure.
Modern Usage:
This is like today's corporate ladder or political career track—the more you climb, the more enemies you make and stress you carry.
Prosperity as Turbulent
Seneca's view that success and wealth don't bring peace—they create chaos. The more you have, the more you worry about losing it, and the more people want to take it from you.
Modern Usage:
We see this with celebrities, lottery winners, or anyone who gets sudden wealth—more money often means more problems, not fewer.
Contempt of Death
A core Stoic practice meaning to accept death as natural and stop fearing it. Not wanting to die, but not letting fear of death control your choices and make you desperate.
Modern Usage:
This shows up in people who take meaningful risks—starting businesses, speaking truth to power, or leaving bad relationships—because they're not paralyzed by worst-case scenarios.
Moral Letters
Seneca's collection of philosophical advice letters to his friend Lucilius. They weren't meant to be published originally—they were real guidance for living well, written in practical, everyday language.
Modern Usage:
These are like the best advice texts or emails you get from a wise mentor—personal, honest, and focused on real-life problems.
The Crowd's Judgment
Seneca argues that popular opinion is usually wrong because most people don't think deeply. They call wise choices foolish and foolish choices smart, especially around money and status.
Modern Usage:
This is why people mock others for choosing teaching over finance, or staying home with kids over pursuing executive roles—the crowd values the wrong things.
Characters in This Chapter
Seneca
Philosophical mentor and letter writer
He's defending his friend's choice to step back from career ambition and teaching Lucilius how to handle social criticism. Shows wisdom through practical examples and analogies that make complex ideas accessible.
Modern Equivalent:
The experienced mentor who's been through the corporate grind and now helps younger people see what really matters
Lucilius
Student and letter recipient
He's learning how to support a friend who made an unpopular but wise choice. Represents someone trying to understand deeper life principles while still living in the everyday world.
Modern Equivalent:
The friend asking for advice about how to support someone who's making choices others don't understand
The Friend in Retirement
Example of wise choice-making
He chose personal peace over public success and is being criticized for it. His story illustrates that doing the right thing often looks wrong to others, especially early on.
Modern Equivalent:
The person who leaves a prestigious job to do something meaningful but lower-paying, facing family and social pressure
The Detractors
Critics and social pressure
They represent conventional wisdom that equates busyness with virtue and retirement with laziness. Their criticism reveals how society often values the wrong things.
Modern Equivalent:
The relatives and former colleagues who question why someone would 'waste their potential' by choosing a simpler life
Key Quotes & Analysis
"Prosperity is a turbulent thing; it torments itself."
Context: Explaining why his friend was smart to avoid the rat race
This reveals that success isn't peaceful—it creates its own problems and anxieties. Seneca shows that what looks like winning is actually a form of suffering that people inflict on themselves.
In Today's Words:
Success is exhausting—the more you get, the more stressed out you become trying to keep it all together.
"Just as he carries his liquor."
Context: Responding to people who say someone 'handles prosperity well'
This analogy cuts through the illusion that some people are immune to the corrupting effects of wealth and power. Even if they look fine on the outside, the damage is still happening.
In Today's Words:
Just because someone doesn't look drunk doesn't mean the alcohol isn't poisoning them.
"They run to him as crowds rush for a pool of water, rendering it muddy while they drain it."
Context: Describing how crowds ruin what they seek
This image shows how popularity destroys the very thing people are attracted to. The successful person becomes a resource that gets depleted by everyone wanting a piece of them.
In Today's Words:
Everyone wants to get close to successful people, but all that attention ends up ruining what made them special in the first place.
Thematic Threads
Social Expectations
In This Chapter
Seneca defends his friend's choice to retire against social criticism and labels of laziness
Development
Building on earlier themes of independence, now explicitly addressing social pressure to conform
In Your Life:
You might feel this when family questions your career choices or friends pressure you to keep up with their lifestyle
Class
In This Chapter
The distinction between those who chase prosperity and those who choose wisdom over wealth
Development
Continues Seneca's critique of material pursuits, now focusing on the social dynamics of success
In Your Life:
You see this in workplace hierarchies where climbing the ladder often means sacrificing what matters most to you
Personal Growth
In This Chapter
Deep learning that 'soaks into your bones' versus superficial knowledge for social display
Development
Evolving from individual self-improvement to distinguishing authentic growth from performance
In Your Life:
This shows up when you choose real skill development over credentials that just look good on paper
Identity
In This Chapter
The friend's identity as someone who chose retirement over career advancement despite social judgment
Development
Expanding on self-definition themes to include resistance to external pressure
In Your Life:
You experience this when you have to decide whether to be who others expect or who you actually are
Human Relationships
In This Chapter
Seneca's loyalty in defending his friend against critics and social pressure
Development
Introduced here as theme of supporting others who make unconventional but wise choices
In Your Life:
This appears when you need to decide whether to defend someone making unpopular but smart decisions
You now have the context. Time to form your own thoughts.
Discussion Questions
- 1
Why do people call Seneca's friend lazy for choosing retirement over career advancement?
analysis • surface - 2
What does Seneca mean when he compares prosperity to a violent storm, and why does he think people who 'handle success well' are like people who can hold their liquor?
analysis • medium - 3
Where do you see this pattern today - people being criticized for stepping away from status games or refusing to chase conventional success?
application • medium - 4
Think about a time when you felt pressure to pursue something everyone else thought you should want. How would you handle that situation differently after reading this chapter?
application • deep - 5
Why does Seneca connect mastering 'contempt of death' to becoming truly free? What does this reveal about how fear controls our choices?
reflection • deep
Critical Thinking Exercise
Map Your Own Status Traps
Make a list of three opportunities or expectations in your life that everyone thinks you should pursue. For each one, write down what it would cost you that you can't get back, what compromises you'd have to make, and what you'd have to defend afterward. Then identify which ones serve your actual values versus which ones just impress other people.
Consider:
- •Consider both obvious costs (time, money) and hidden costs (stress, relationships, personal integrity)
- •Think about the difference between what you genuinely want and what you think you should want
- •Remember that saying no to one thing means saying yes to something else - what would you gain by stepping away?
Journaling Prompt
Write about a time when you chose the path that disappointed others but felt right to you. What did you learn about yourself? How did it turn out in the long run?
Coming Up Next...
Chapter 37: The Soldier's Oath to Virtue
The coming pages reveal commitment to personal growth requires the same dedication as military service, and teach us to distinguish between what you can control and what you must endure. These discoveries help us navigate similar situations in our own lives.