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5 Tips on Making You a Tough (& Better) Writer

Becoming a masochist early on – embracing the pain to the point of enjoyment - may be the single best investment an aspiring writer can make. The pain takes many shapes, all of them useful along the writer’s path.

Publishing a book is an unpredictable process, but it does come with some constants.

One of those are the confessions.

They’ll come from all over one’s social network. The people making them will invariably speak of this “book” that’s been “inside” of them for years. Most will expect the author to deliver some kind of formula – a key to opening literary floodgates that have unfairly been kept shut to date.

This guest post is by Frederick Pinto, an intellectual property lawyer and writer based in Montreal. He is the co-founder of Uprise.FM - a new, artist-centric streaming platform focused on live and unique recordings, co-founded with 11-time Grammy award winning producer Daniel Lanois. He is a contributor to the Huffington Post, and has written articles on music, culture and entertainment for peer reviewed law journals, magazines and newspapers. In 2012 he published The Sabbatical, a novel based in today's music industry.


By far the most damaging thought I’ve heard from the confessors - and other authors have told me the same thing over and over - is the expectation that writing should be a “fun” or “leisurely” activity. Pop culture reinforces this by perpetuating the image of the writer as a mega-talented, but lazy and self-indulgent buffoon (think Hank Moody).

And so, many overcome the first hurdle – deciding to start - ready for the magic to happen. Expecting it all to emerge, freshly baked and ready for primetime.

Then, of course, it doesn’t.

Then anxiety kicks in.

Fear of judgment by others, doubts about one’s abilities. Mounting frustration as to why it’s so much slower and more agonising than one expected.

The plain truth is, writing is a predictably painful process. It is far more hard labor than careless play.

And it's not like the greats haven't warned us.

Becoming a masochist early on – embracing the pain to the point of enjoyment - may be the single best investment an aspiring writer can make.

The pain takes many shapes, all of them useful along the writer’s path.

[The Top 10 Elements of a Book People Want to Read


1. Embrace the Road to Hell

As Hemingway once so elegantly put it, "the first draft of anything is shit."

And that’s only when one produces something so elaborate as to be called a “draft”.

Most of the time, writing remains stillborn, in a kind of literary purgatory. Outlines, random notes, sketches, hackneyed bits and pieces – they have a way of quickly prematurely bursting into life, only to suddenly stop breathing and just hang there.

Philip Roth was slightly more inclusive when he said “the road to hell is paved with works-in-progress.”

Both Hemingway and Roth touch on the elemental truth of all writing: it's not good.

At least not at first.

Kerouac’s celestial typewriter notwithstanding, good writing doesn’t just naturally “babble flow”. And when it does, it’s usually shit.

Get over this quickly, and take the next step in the journey. The one where you get to murder children.

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2. Kill Your Darlings

Getting rid of bad writing - while essential - is not even the worst part. You’re supposed to identify and scrap the bad stuff.

Far more agonizing is eliminating the good stuff that doesn't fit.

In his masterful memoir On Writing, Stephen King calls this part of the process “killing your darlings”.

This crucial tidbit of advice has, over the years, been attributed to writers as diverse as William Faulkner, Oscar Wilde, Eudora Welty, G.K. Chesterton, and Anton Chekov[1] , but King gave it its most poignant modern iteration:

“Kill your darlings, kill your darlings, even when it breaks your egocentric little scribbler’s heart, kill your darlings.”

To the pain of writing must be layered the pain of deleting.

When in doubt, heed King’s reassuring nod.

“It must be done.”

[Learn the 4 Successful Approaches You Should Consider for the First Chapter of Your Novel]

3. Connect to the Pain of Others

Pain is not, however, an end in itself.

Its purpose is often times to link the writer to the pain felt by others. Most entertainment distracts us from the pains of daily life. Writing and reading, can, at their best, be about placing those pains under a shining light.

Anais Nin implores us that “if you do not breathe through writing, if you do not cry out in writing, or sing in writing, then don’t write. Because our culture has no use for it."

Likewise, for Kurt Vonnegut, the pain of writing is a mere reflection of the pain of existence – you provide others with relief by admitting to the suffering publicly.

“Do you realize that all great literature is all about what a bummer it is to be a human being?” Vonnegut asks. “Isn’t it such a relief to have somebody say that?”

One of the tragedies of social media has been its penchant for turning writing into oceans of brainless typing – another trivial form of expression in a culture filled with them.

But, at its core, writing is – and perhaps always has been – a cathartic activity.

Those who disagree would do well to keep Nin’s advice handy.

4. Follow your obsessions

When writing seriously, there’s an invisible, yet persistent pressure to conform to perceived social standards.

The rise of countless writing programs and “how to” books only reinforces this. So does the consolidation of the publishing industry – the merger of Random House and Penguin making the process all but complete.

Sure, there are advantages to all of this – streamlining and efficiency and technique are not bad things per se.

But the barrage of rules and procedures can just as easily distance the writer from the primal urges that gave rise to the need to write in the first place.

Kafka speaks of “the pains of doing what's real, in jest of literary conventions, and no matter whether it will result in a publishing deal.”

The irony, in today’s supposedly “free” environment, is that there are still tons of over-editing, conforming, and self-censorship going on – especially by writers with hopes of being commercially published.

“Don’t bend; don’t water it down; don’t try to make it logical; don’t edit your own soul according to the fashion.” Kafka expounds. “Rather, follow your most intense obsessions mercilessly.”

Writing is not just technique. It is also, at least equally, an obsession.

[Understanding Book Contracts: Learn what’s negotiable and what’s not.]

5. Sometimes, it’s just a Disease

In some cases, the warnings are literal.

Orwell called writing a book a "horrible, exhausting struggle, like a long bout of some painful illness."

William Carlos Williams goes even further, saying "I think all writing is a disease. You can't stop it."

Contrary to appearance, these are not “negative” views of writing. Rather, I see these statements as Orwell and Williams seeking to abandon themselves to the destiny of being writers – something they don’t fully understand, but that is nonetheless drilled into their DNA. Something they’ll pursue through thick and thin.

The process of writing can challenge us to the core. It more than hurts us – it afflicts us.

But maybe that’s part of the price. To give the world something truly valuable, one must sacrifice from the flesh. With this in mind, it actually helps if one believes this to be an inevitable part of one’s destiny.


Every part of the process involves a different form of hardship that must ultimately be embraced if one is to move on.

The expectation of immediate joy and pleasurable sensations probably kills more literature than any other thought.

The literary masochists got it right - pain is something to be embraced, enjoyed and accepted as an integral part of the writing life.

When you inevitably feel it, I tell my confessors, don’t stop. Smile, as you’ve just met your most reliable companion on the road to literary completion.

Other writing/publishing articles & links for you:

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Brian A. Klems is the editor of this blog, online editor of Writer's Digest and author of the popular gift bookOh Boy, You're Having a Girl: A Dad's Survival Guide to Raising Daughters.

Follow Brian on Twitter: @BrianKlems
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