rebelling against low expectations

5 Things Aspiring Writers Can Learn from G.K. Chesterton


Rarely has a mastery of so many tenets of literary pursuit been so demonstrated by a single author than that which is apparent in the voluminous writings of one Gilbert Keith Chesterton.

G.K. Chesterton was the jovial turn of the (20th) century English writer who penned numerous books, articles, comic verses, and everything in between, all to varying but invariably considerable degrees of success. He approached everything he wrote about and, if his biographers are even half true, many things about which he did not write, with much of the wonder he so admired in the child paired almost seamlessly with the incisive wisdom and wit of our most capable philosophers. Any hopeful writer would be astoundingly fortunate to rival Chesterton’s enduring popularity and influence, let alone the beauty and truth represented in his writings.

What you’re about to read is a synopsis of five practices and virtues all of which we consider to have been contributing factors to that brilliance which was Chesterton’s, some were even explicitly endorsed and described by the man himself. We believe these can prove invaluable for the young writer who admires composition as art and aspires to put his or her hand to the plough – a worthy aspiration indeed. In applying with discretion which of these best pertain to our own writing, we have found great pleasure and profit and believe you will too. Enjoy!

1. Read Well

“The first use of good literature is that it prevents a man from being merely modern. To be merely modern is to condemn oneself to an ultimate narrowness.” – G.K. Chesterton

It is said, and said truly, that a good writer is first a good reader.

G. K. Chesterton is well known, among many other things, for his biographies and literary criticisms. The remarkable feature of his approach to historical works is that, rather than attempting to record the past through the lens of the present, he managed by having immersed himself in the works of the men he studied rather to view the present with the borrowed lenses of men of the past, and thus to explore the timeless truths of their lives and works.
It is tempting, in the age of the internet, to devalue this experiential approach to truth.

‘Why should I learn about Whitman when I can google his name?’

‘Why should I read ‘Paradise Lost’ when I have the Cliff Notes at my fingertips?’

The answer to both of these questions, aside from the sheer joy of experiencing good art, lies in the fact that, for better or for worse, the things we pursue and appreciate shape our identity and our observations. By immersing ourselves in the greatest art of the past and present, we may also in part adopt the lenses through which their respective creators viewed their own world.

We may look momentarily upon Dickens’ London and Hugo’s Paris. We may gaze on the romanticized adventures in Stevenson’s south seas, enjoy the serenity of Alcott’s New England, stand transfixed in the harrowing reality of Baldwin’s Brooklyn, and perhaps even marvel at a fantastical representation of an unknown distant planet. This sharing of others’ adventures, in both fiction and non-fiction, has the potential to transfix us and impress upon our imagination new sights, sounds, and sensations of wonder. These borrowed lenses we may then apply to our own surroundings, finding in New York, Buenos Aires, or whatever seemingly commonplace hamlet the complexities of Dickensian characters. We may, upon closer examination, find all the warmth of ‘Little Women’ on our own hearth and all the excitement of Treasure Island in the inconveniences of everyday life.

As writers who draw from the wealth of literature so readily available to us today, we may thus discover the strands of humanity that constitute each of us, and are the lifeblood of good literature. And with them weave a tapestry that can translate the complexities of our environments and neighbors to us, and in turn, help us convey our observations and tiny wisdoms to the world.

2. Be Observant

“Do not look at the faces in the illustrated papers, look at the faces in the street.” -G.K. Chesterton

One of Chesterton’s most successful and broadly inspirational novels; The Napoleon of Notting Hill, was entirely the result of one single, simple observation: namely that one particular and very modern set of shops on Notting Hill in London would make a fantastic independent fortification in the unlikely event of a medieval military siege. What a thought! So unexpected yet unexpectedly apropos.

Likewise, the entirety of Chesterton’s 1912 novel Manalive is centered on his realization that “the way to love anything is to recognize that it may be lost” – a simple and ordinary observation, yet profound. Chesterton was thus exceptional. He understood his world because he really, truly lived in it, because he delighted in its mundanity and wondered at the complexity of all of its delightful obscurities. He refused to allow society’s expectations and manufactured normalities to determine what he observed in his world or even how he went about doing so.

The greatest test of creativity is not to invent new worlds, but rather to truly see the wonder and potential of the world we already inhabit. Creation is already far more strange and beautiful than anything we could independently originate! Its only limitation is the imagination required to see it. A myriad of wonders and profundities are coded into your environment waiting to be found, all you have to do is keep your eyes open long enough to see them.

The world will never starve for want of wonders, but only for want of wonder. - G.K. Chesterton Share on X

As Chesterton himself said, “The world will never starve for want of wonders, but only for want of wonder.”

3. Be Authentic

Any youthful, aspiring writer can perhaps draw from this point of observation – Chesterton was not at all afraid to be himself. Indeed, numerous accounts exist of him loudly and publicly laughing at his own jokes as he wrote them, volubly conversing with invisible interlocutors whilst swinging a sword in his back garden, among other similar anecdotes. He was at home in his personhood, and such sound certainty is perhaps a helpful departure point for our own journeys into the world of composition.

Chesterton could express himself because he knew himself, both who he was and who he could be. This allowed him to be unapologetic in that expression and to articulate what he honestly felt was true in his own original way. This does not mean that he was always intransigent in his positions and never changed his mind, because he did – sometimes drastically but never disingenuously.

Chesterton championed authenticity both in his life and work. We draw from his example the following principle: Honesty with oneself about oneself is a crucial piece in many of life’s puzzles especially in matters of self-expression of which writing is one of the highest modes. Chesterton believed that this authenticity is often manifested in how we represent our opinions, arguing that having a strong opinion about something was generally more honest than pretending not to. He went so far as to claim that “Impartiality is a pompous name for indifference, which is an elegant name for ignorance.”

When you write, write honestly and with conviction. Don’t just write what you think certain people want to hear when it goes against your internal compass. Avoid rearticulating popular dogmas merely because they’re popular. Do not pedal noisome and aimless sensationalism, which is always popular but rarely useful and never completely genuine. Write with the confidence of knowing that you wholeheartedly believe what you are writing, because after all, if you cannot believe it yourself, how can you expect others to? Share on X

4. Be Respectful

Chesterton displayed a quality unique to exemplary writers – it is best described as respect. In all of his literary and artistic productions, he maintained this remarkable sense of respect for everything that is respectable. He respected his audience, his predecessors, himself, his God, and perhaps notably, his detractors. Before he destroyed anything he made sure to find out why it was there in the first place and before he built anything new he made sure it was something that could serve a purpose.

When Chesterton engaged his enemies and detractors this respect for what was respectable in them, he rendered his withering critiques and masterful rejoinders all the more potent for possessing none of that contumelious vitriol to which those who write critically but without respect must resort. And when he attempted new works of fiction, it was with a deeply imbued respect for all the components of storytelling; audience, imagination, language, creation, and so forth.

It is important for writers, most especially Christian writers, to be respectful when we write so that God is glorified and truth can take center stage without too much of ourselves getting in the way. Our observations will be brighter when we, to some degree, understand the world that we observe and respect what is respectable in the environment our observations must encounter after we make them. Even our stronger words and honest criticisms will be more palatable and more likely to achieve an honest purpose if respect permeates our every expression.

Chesterton exemplifies this attribute when he said, “Love means loving the unlovable or it is no virtue at all.”

5. Be Humorous

“Humor, like wit, is related however indirectly, to truth and the eternal virtues: as it is the greatest incongruity of all to be serious about humor, so it is the worst sort of pomposity to be monotonously proud of humor, for it is itself the chief antidote to pride, and has been, ever since the book of Proverbs, the hammer of fools.” – G.K. Chesterton

Perhaps one of the most easily recognizable Chestertonian traits is his constant employment of humor as both a rhetorical and narrative device. He defined this commendable virtue as “a term which not only refuses to be defined, but in a sense boasts of being indefinable” (and it would commonly be regarded as a deficiency in humor to search for a definition of humor).

Humor is a fundamentally important component of balanced life and discourse. Not because it makes light of heavy things or contrasts severity with frivolity but because it is essentially an outpouring of humility and thereby graces difficult topics and heavy situations with an approachable, almost bearable aspect. It acts as a brake both against falling too low or assuming to ascend too high. By being the silver lining to dark clouds and the proverbial sugar to assist the ingestion of medicine, humor is a failsafe antidote to the enduring damages of tragedy, pride, and heartbreak. In a cosmic paradox, humor realizes humility to locate the risible in everything. As said Chesterton:

“He is a sane man who can have tragedy in his heart and comedy in his head.”

Chesterton wielded his firm grasp of the utility and nuances of humor to great effect throughout his life. This is evidenced both in his writings directly on the subject itself, and his effortless employment of its devices which permeates his entire body of work. When he wrote stories, humor gave them just enough whimsy to be really real. When he wrote essays, humor buoyed his wisdom and flavored his expressions. And when he debated, expressive humor demonstrated the depth of his understanding.

As authors we may hope to emulate this quality by, like Chesterton, ensuring that we do not become the center of our own stories. When we focus more on our representation of truth than the truth we represent, we abandon our sacred charge. When we abandon the humility of humor we leave behind the truth of humility along with it. Thus we must cultivate that essential humor by maintaining our resolve to tell the truth; especially as it relates to ourselves.

Because truth itself is the source of all humor, you cannot fully understand the truth about anything until you are able to joke about it.


Our admiration for Chesterton as a writer lies within not only what he created but in what he inspires us to create. He testifies to the tremendous effect writing can have; he gives us for a single moment the bliss of credulity, even if expressed incredulously. He permits us to momentarily make ourselves small so that the world might grow large around us, that the grass may become as large as trees and the trees as large as the fabled beanstalk reaching to the heavens, as large and as magical.

Chesterton displays what any writer can be and any writer can do, each in his or her own distinctive, idiosyncratic, and even eccentric way. He thus invites us on a journey as writers, one beginning with immersion and adventuring through reading, one that calls us to embrace our authentic selves, one that holds us to a high and noble ethic of respect, and last but not least, one that encourages us to embrace humor as the lifeblood within our veins and as the merriest of balms to our soul.

If we may end on a note of indulgence, it is only to marvel at the genius with which Chesterton imbued his work. Chesterton invites us to see the beauty in a sunset for the very first time, but only by watching it for the thousandth time. He demonstrates that one may, and indeed should discover new lands if only to discover that it is their homeland. He implores us through his writing to discover Christ, only to recognize that it is Christ who has discovered us. He proclaims with a startling and fresh newness that everything is as it always has been. He informs us in a reckless abandon of surprise and delight that the sun has risen yet again, and doubled the miracle of it having risen yesterday. He announces in sheer childlike fascination and joy that the grass is green and the sky is not, that the world is round and that it goes on. At every turn, He affirms loudly and even defiantly that when God said “it is good” he actually meant it, and “of such is the kingdom of heaven.”

If you would like to become better acquainted with the life and works of the man himself; please contact the authors by email at ‘[email protected]’ as they would be delighted to assist you towards that end by any necessary means.

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About the author

U.S. O'Terry and E.M. Milioni

U. S. O'Terry is a 21 year old aspiring normal person and the eldest of 11. He has been informed by very smart people that he was born in Eugene Oregon and in a colossal act of faith believes them. He currently resides in the preposterous state of Michigan and is in possession of certain compelling proofs to that effect. He can be found spending too much money at the local used bookstore or pontificating on the mysterious wonders of the universe in various locales.

E.M. Milioni is an aspiring idealist, and private librarian. He may often be found near any considerable supply of antiquated literature in the greater Boston area, or in the more ancient culinary establishments in their near vicinity. He enjoys anything which is communicatively transcendent, including particularly delightful cups of black coffee.

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rebelling against low expectations

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