Paul Graham on Writing: What Went Wrong

Paul Graham essays are usually highly acclaimed. But his latest, “Write Simply,” ( got a lot of criticism in the comments compared to the typical column. So what went wrong.

There are several problems:

Some readers noted in the comments that using only simple, short words and short sentences can come across as jarring by breaking the ‘flow,’ which actually makes the writing harder to read and process than a varied writing style that combines long and short sentences and words. One needn’t deliberately choose simple words or write short sentences, but rather choose the vocabulary and sentence structure that best conveys the message to its intended audience, and comes across as natural to the writer. I n this passage I use compound sentences because they are efficient for isolating ideas within a sentence instead of using unnecessary words.

Second, Paul’s great career success and his plain writing style, although correlated, is insufficient to prove causation. His success as a writer is in no small part attributable to his success as a venture capitalist; notably, his seed investments in Airbnb and Dropbox, both of which have earned him presumably hundreds of millions or billions of dollars. If not for those investments, would he still be as successful as a writer as he is now, with as many readers as he has presently? Maybe not. Same for Peter Thiel, whose massive Facebook windfall is a reason why so many people take him seriously as an intelltual and writer. Having invested $500,000 Facebook in 2005 when the social network was just a year old, made him a billionaire, and with his newfound celebrity status, expanded his brand to include other activities such as politics and writing. Another example is Bill Gates, whose success as a writer having in 1995 published the best-seller The Road Ahead, in which he makes predictions about technology, is in large part an extension of his success with Microsoft.

The best of writers are unable to avail themselves of non-writing successes as a substitute for raw talent and skill, which is not to say that writers who have non-writing successes are untalented or bad at writing, but having name recognition from non-writing endeavors helps immensely in terms of building a readership and gaining recognition. Without such help, it’s sink or swim by virtue of the message and how it is conveyed through the writing alone. Which is very hard to do and few succeed at it. This is why writing guides are useless. You don’ t need guides. You just need to read stuff by writers who succeeded through their writing alone and then try to learn from what they did to become successful.

Like Moldbug. He found a successful niche despite otherwise being unknown by writing 10-thousand word treatises on political philosophy. He established a rubric that longer is better. Same for Tim Urban of WaitButWhy, who in 2013 captivated a readership in the hundreds of thousands by writing book-length essays about non-mainstream stuff like Cryonics. 500-word articles are a dime a dozen, but something that is 5,000 or 10,000 words, establishes implicitly to the reader that what they are about to read is a substantive, serious piece of work that merits more than a glancing consideration, as substantial time, effort, and thought went into it. Interestingly, in keeping with this trend, the above essay was also Graham’s shortest at just 510 words, but the essay that preceded it “What I Worked On,” weighing in at 13,800 words, got a universally favorable reception.

Another example is Scott, who began blogging over a decade ago while studying to become a therapist, succeeding at both and building a massive readership by the power of his writing alone. Scott is a skillful writer in that he is able to articulate his views in such a way that he is able get people who would disagree with him, to respect and like him and even become frequent readers of his content. Most writers cannot do that and just come across as irritating or grating to anyone who is not their intended audience. Scott can cross ideological divides in ways few other writers can, while at the same time not relying on the crutch of being neutral. Scott can takes sides by opposing Trump and still retain the retain the respect of Trump supporters, who may disagree with Scott’s conclusions but concede that he raised valid points and is a worthy intellectual opponent. It involves a combination of earnestness and humility and a concerted intellectual effort to understand the opposing side, that most writers fail at (such as by misconstruing or uncharitably interpreting the opposing side’s argument, which is an automatic disqualification as far as credibility and persuasion is concerned). Most opinion/editorial writers write in order to win an argument, usually against an imaginary opponent that is conceived to lose and make the writer look smart (the so-called strawman), or by preaching to the choir that is their tribe/ingroup, not to persuade the opposing side or the most skeptical of readers.