10 Beautiful Life Lessons From Reading Seneca's Masterpiece

A practical and pragmatic guide to living a virtuous and fulfilled life.

Seneca was a Roman philosopher who famously nurtured Emperor Nero until he ordered his tutor to death by suicide. He published several essential works on Stoicism and is considered to be a key Stoic philosopher alongside Marcus Aurelius and Epictetus.

I’ve read Marcus Aurelius’ Meditations but found this book wholly more enjoyable. Although Meditations is no doubt a classic. A peak behind an Emperor’s curtain, never meant for the eyes of anybody else I did find it often hard to get into. It’s full of wisdom but often they are anecdotes and soundbites, other times just pure rambling. Therefore I found it hard to read more than a few pages at a time. There is nothing wrong with this approach, but there was just too much to think about so it’s not really a book I read but rather a book I dipped in and out of.

Letters From a Stoic on the other hand was different. The letters range from a couple of pages to upwards of 15 and the running theme is that they are all to his friend Lucilius. The topics covered in the collection of letters include all the traditional Stoic virtues such as wisdom, temperance, justice and courage but also include how one should eat, bathe and walk. How we should act in illness. His opinion on liberal arts. Cold baths. Exercise. Perhaps because it’s meant to be for a reader I got more out of this book, but Seneca goes into great detail, oftentimes with great wit how he believes man (anybody) should live. I often found myself in awe at the beauty of his writing and envious of his mind

The book serves as a guide to navigating the complexities of human existence with grace and wisdom. Seneca's letters offer profound insights into the human condition, making "Letters From a Stoic" a timeless and influential work in the realm of philosophical literature.

I highlighted 10 letters as my favourites and picked out some of my favourite passages. Below are highlights from those 10 letters with some personal commentary.

Letter II

Nothing, to my way of thinking, is a better proof of a well ordered mind than a man’s ability to stop just where he is and pass some time in his own company. To be everywhere is to be nowhere.

In this letter, Seneca is praising Lucilius telling him he shows ‘great promise’ because he does not ‘tear from place to place.’

It’s interesting and sad to see that men and women from around Seneca’s time were having the same problems as men and women some 2 thousand years later. I only feel, as I’m sure Seneca did back then, that it’s amplified even more now. I have friends who can’t stand being in their own company. If you can’t be a best friend to yourself, who will? Some of the best advice I got from anybody was from a friend after a breakup. He said, “You need to spend some time being in your own company until you are comfortable doing so”. Interestingly, he was reading Stoicism before I was and passed on Seneca’s ‘On the Shortness of Life’.

‘A cheerful poverty’, he says ‘is an honourable state’. But if it is cheerful it is not poverty at all. It is not the man who has too little who is poor, but the one who hankers after more.

This is a common theme throughout the book with Seneca. What is enough? We live in an age where there are nearly 25 million, millionaires in America alone. Just over 7% of the population, yet depression rates, (18%) are the highest since records began. The internet is full of ‘bros’ ‘hustling’ and ‘grinding’ yet the arrow of unhappy people seems to be travelling in the wrong direction. Seneca has an answer for this:

You ask what is the proper limit to a person’s wealth? First, having what is essential, and second, having what is enough.

On the surface level this can seem as if it’s a rather socialist way of thinking and I for one don’t begrudge Capitalism. It’s what is allowing me to write this newsletter. Your enough may be a comfortable salary, it may be a few million a year. The lesson is in the word, enough. Spend some time thinking about that word.

Letter III

After friendship is formed you must trust, but before that, you must judge.

Facebook. Friend requests. People you have never met or heard of just slide into your inbox. The idea is it makes us more social. More connected. I don’t need to go down the social media rabbit hole, that’s a separate article in itself. Maybe a series. But for all that social media can provide it’s safe to say that it brings out the worst in people. Hooked on doom scrolling and dopamine injections we hide behind these fabricated facades. Some people set up accounts without anybody knowing who or what they are just to troll people.

How different these interactions online are than with real people. How easy it is for your message to be misconstrued when people don’t have the luxury of falling back on thousands of years of studying body language, tone and facial expressions. How easy it is to say something wrong and lose a career. Yet these people follow you. They’re supposed to be your friends. With real friends, you can say anything and they’ll tell you if you are right or wrong. Unless you’ve hidden away from them the fact that you’re a massive homophobe or racist they’ll still be your friend no matter what you say. Arguments and disagreements and all.

Seneca knew back then that friendships are something to be earned not just given away.

Letter V

Philosophy calls for simple living, not for doing penance, and the simple way of life need not be a crude one.

There are philosophers and some philosophies that call for a standard of living that even when they were advocating for it, thousands of years ago was sub-standard. Seneca’s approach is somewhat different, perhaps because he was high up in the Roman Empire, did he feel he needed to preach something different in case he came across as hypocritical? Perhaps it’s to make it more acceptable and approachable to more people? Letter V is his first letter where he speaks about philosophy. How people should act and dress. What they should eat with. Seneca’s idea is to sit right in the middle of the high and mighty and that of the mob, having no inclination to one side or the other.

Seneca rounds the letter off with some advice from Hecato about fear, hope and being present.

Limiting one’s desires actually helps to cure one of fear. ‘Cease to hope and you will cease to fear’. Wildly different though they are, the two of them march in unison like a prisoner and the escort he is handcuffed to. Fear keeps pace with hope. A number of our blessings do us harm, for memory brings back the agony of fear while foresight brings it on prematurely. No one confines his unhappiness to the present.

Letter XII

How nice it is to have outworn one’s desires and left them behind.

We all dread growing old. Moving through the different phases of life, life gets much harder with each passing one. Going from a kid to a teenager is exciting. A teenager who is old enough to go out with his friends is like winning the lottery. I’m sure there aren’t many elderly people who loved going from their 20’s & 30’s to their 60’s & 70’s. Yet Seneca thinks that people should rid themselves of this misconception that growing old is bad.

After all, one can not predict when you are to die.

The order in which we each receive our summons is not determined by our precedence in the register.

They say there are two guarantees in life. You die and you pay taxes. Only one of them is true, however. Living under this constraint need not shackle us. By thinking about death, about the death of a loved one, one can begin to appreciate life a little more. It’s uncomfortable but none more so than being on your deathbed wishing you had lived just a little bit more.

To live under constraint is a misfortune, but there is no constraint to live under constraint.

Letter XV

The life of folly is empty of gratitude, full of anxiety: it is focused wholly on the future.

In this letter, Seneca starts by speaking about exercise, both for the body and for the mind but the letter moves on to more philosophical questioning. Our wants and desires. We constantly compare ourselves to other people and we constantly compare what we have to other people as well. This is amplified millions of times in today’s digitally connected world but if you compare yourself to one or to many is it not the same?

Seneca urges us to be independent of fortune. To accept our lot.

When you look at all the people out in front of you, think of all the ones behind you. Set yourself a limit which you couldn’t even exceed if you wanted to, and say goodbye at last to those deceptive prizes more precious to those who hope for them than to those who have won them.

Letter XVI

Natural desires are limited; those which spring from false opinions nowhere to stop. For falsity has no point of termination.

In this letter, Seneca begins by talking about the pursuit of wisdom. He explains that to live a happy or even bearable life one must seek wisdom. The letter talks about self-scrutiny and natural vs artificial desires. Seneca states that nature provides us with all that is needed to live a good life but acknowledges things that people want can have no endpoint.

The same can be said for the opinions of people. If you seek approval from anyone and everyone there’s an endless sea of approval. Seneca quotes Epicurus, beautifully;

If you shape your life according to nature, you will never be poor; if according to people’s opinions, you will never be rich.

Letter XXVI

Rehearse death. To say this is to tell a person to rehearse his freedom. A person who has learned how to die has unlearned how to be a slave. He is above, or at any rate beyond the reach of, all political powers. What are prisons, warders, bars to him? He has an open door. There is but one chain holding us in fetters, and that is our love of life. There is no need to cast this love out altogether, but it does need to be lessened somewhat, so that, in the event of circumstances ever demanding this, nothing may stand in the way of being prepared to do at once what we must do at some time or other.

The Stoics are renowned for talking about death. They say we shouldn’t attach value to anything that can be taken away from us. That we should feel indifferent about such things. Wisdom, courage and temperance, however, are things that we can hone and things that can never be taken away from us, but life, whether our own or others can be snatched away from us in an instant.

At first, this can seem rather depressing and depending on which Stoic you read you’ll get the impression that this is all a bit cold-hearted and unpractical. To say that I shouldn’t get upset if my wife or dog dies because they are not mine doesn’t sit well we me. But I think the more you read what they say about it and how they say it you can begin to understand where they’re coming from. It’s because the Stoics rehearse death and meditate on losing your life or that of somebody you love that it can be used for the better. How many times a day do you stop to think about, deeply, the people most important to you in your life? I think of my wife throughout the day when I’m not with her but a lot of the time it’s routine. I’ll call to ask what we should make for tea. I’ll text to let her know I’m going gym after work. That sort of thing. If I sit there and think about what my life would be without her. How my days would be, it’s awful. It’s enough to make me well up. This is the point the Stoics make. It brings back into focus the things that are important to you instead of just going through the motions.

Think of yourself dying on your deathbed. It’ll conjure up thoughts on things you wished you would have done and things you wish you would have said. How sad and unfulfilled you might feel, but the beautiful thing about doing this every now and again is you’re not on your deathbed. You still have a chance to do and say those things. What you need is courage. Action.

This isn’t some depressing routine the Stoics preach to make themselves indestructible and cold-hearted. Stoicism is everywhere nowadays and a lot of it is misinterpreted and misguided. A lot of it is picked up by men with no direction and it’s used as a tool to shut yourself out and down and to turn yourself into some sort of mythical warrior who can run through walls. Physical and emotional ones. If you want to learn about Stoicism and some of its practices read the classics, not some Twitter bro.

Letter XXXIII

This is why I look on people like this as a spiritless lot - the people who are forever acting as interpreters and never as creators, always lurking in someone else’s shadows. They never venture to do for themselves the things that they have spent such a long time learning. They exercise their memories on things that are not their own. It is one thing, however, to remember, another to know. To remember is to safeguard something entrusted to your memory, whereas to know, by contrast, is actually to make each item your own, and not to be dependent on some original and be constantly looking to see what the master said. Besides, a man who follows someone else not only does not find anything, he is not even looking.

The Stoics believed in mentorship and understood the importance of it and up until a generation ago the net that anybody could turn to for mentorship was rather small. Where people once turned to close relatives, friends, teachers, books, and TV stars for people to look up to, there is now an unlimited amount. Never have we been so connected. If that’s what you can call it. The digital age has given anybody with an opinion a platform to share it. The good and the ugly. Finding a mentor has never been so easy. Finding the right one, never so hard.

I see this with books as well. At my fingertips is almost every book that is available in the world ready to be bought and delivered the next day or downloaded instantly to my digital devices. There is literally, an infinite amount of books that would take a biblical amount of time to read. The problem with this, and Seneca saw this with philosophy, is it’s much easier to sit on the sidelines as an observer than to act. We all love to sit on our phones and watch YouTube or other social media apps of people DOING. For some bizarre reason, it motivates us, until it doesn’t. But, guess what? I’ll just go back online and find some more stuff.

Reading a book a week is pointless if you’re not doing anything with the knowledge you’re digesting. How can you be when you’re right into another one, taking on new principles, and new ideas? It’s better to read a book you enjoyed 3 times than to read 3 average books. But it’s even better to act on things you find valuable whether from a book, a mentor or philosophy.

Letter XC

He has taught us not just to recognize but to obey the gods, and to accept all that happens exactly as if it were an order from above. He has told us not to listen to false opinions and has weighed and valued everything against standards which are true. He has condemned pleasures an inseparable element of which is subsequent regret, has condemned the good thing which will always satisfy, and for all to see has made the man who has no need of luck the luckiest man of all, and the man who is master of himself the master of all.

In this passage, Seneca asks the philosopher what has he investigated and this is possibly my favourite letter from the book, this letter speaks in great detail about acquiring philosophy. The letters towards the end of the book get more theoretical in their wording and questioning and encourage the reader to ask questions of themselves.

Letter CVIII

But enough, or before I know where I am I shall be slipping into the scholar’s or commentator’s shoes myself. My advice is really this: what we hear the philosophers saying and what we find in their writings should be applied in our pursuit of the happy life. We should hunt out the helpful pieces of teaching, and the spirited and noble-minded sayings which are capable of immediate practical application - not far-fetched or archaic expressions or extravagant metaphors and figures of speech - and learn them so well that words become works. Let me indicate here how men can prove that their words are their own: let them put their preaching into practice.

The world is full of anecdotes and soundbites. This isn’t lost on me. This article is based on bitesize quotes that are as easy to forget as there are to remember. As mentioned above when you acquire knowledge you need to put it to use otherwise you are but a mere talking memory box of other people’s opinions. Have mentors, have quotes, have knowledge, but make it your own. Practice. Do.

It seems that there are the same two types of people in this world today as there were 2 thousand years ago. Those who say, and those who do.