Words Matter: How the Quality of Your Writing Signals Your Clarity of Thought

Charles Wheelan

May 18, 2022

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Writing for life requires composing your thoughts in a way that gets your desired response, whether that is laughs in a comedy club, a raise from your boss, a large donation to a food pantry, or something else. This is a crucial life skill.


Language is how we interact with other humans. Words matter.

Politicians use language to sell their ideas and capabilities. Hope and Change. With just three words, Barack Obama embodied the promise of his presidency. Make America Great Again did the same thing for Donald Trump. That’s four words, and I suspect you responded to them with strong emotion.

Journalists write to inform us as succinctly and accurately as possible. Columnists write to persuade us, or to inspire us to think in new ways. Comedians spend months or years crafting a joke. One misplaced word and the joke falls flat. Entrepreneurs write business plans to attract investors. Dave Girouard, former president of Google Apps and the founder and CEO of Upstart, feels so strongly about the importance of good writing in business that he wrote a manifesto, A Founder’s Guide to Writing Well. He declared, “Of the many skills attributed to successful entrepreneurs—vision, execution, persuasion, perseverance, grit, resilience—effective writing inevitably fails to make the list. Yet I submit to you that the quality of your writing contributes to the outcomes you experience as a founder and executive day in and day out.”1 Judges use language to render decisions. There is a winner and a loser in every case, but those verdicts also provide guidance for other courts. When the Supreme Court renders a decision, such as a verdict on the role of affirmative action in college admissions, the language in the majority opinion is an instruction manual for the lower courts. The clearer the language, the less confusion there will be around that legal issue in future decades.

Sloppy writing sows confusion. The Second Amendment to the US Constitution reads: “A well regulated Militia, being necessary to the security of a free State, the right of the people to keep and bear Arms, shall not be infringed.” I have great admiration for the Constitution, but that sentence was not the framers’ best work. What exactly does that cumbersome, passive sentence tell us about whether Washington, D.C., can ban handguns? Legal scholars and policymakers have been arguing about the meaning of the Second Amendment for as long as I have been alive.When President George W. Bush nominated White House Counsel Harriet Miers to serve on the Supreme Court in 2005, New York Times columnist David Brooks wrote a scathing appraisal of her qualification to serve on the high court. His complaint was not based on Miers’s ideology or her legal experience. He objected to her abysmally poor writing, which he believed indicated a lack of clear thinking. Brooks cited passages like this one: “We have to understand and appreciate that achieving justice for all is in jeopardy before a call to arms to assist in obtaining support for the justice system will be effective. Achieving the necessary understanding and appreciation of why the challenge is so important, we can then turn to the task of providing the much needed support.”2

It is hard to finish those sentences without skimming; I’ve read them repeatedly and I still have no idea what they mean. Brooks, a wonderful columnist, wrote, “Surely the threshold skill required of a Supreme Court justice is the ability to write clearly and argue incisively. Miers’s columns provide no evidence of that.” President George W. Bush ultimately withdrew the Miers nomination. There were a lot of reasons for that, but the trail of opaque legal writing did not help.

What does great legal writing look like? Elena Kagan is the best writer on the current Supreme Court, says Jennifer Sargent, a colleague of mine at Dartmouth College who teaches legal writing. “Kagan is the most persuasive writer, and that’s the job of a jurist,” Sargent explains. Justice Kagan has an aptitude for writing majority opinions, which require language that can hold a coalition of justices together, like a diplomat finding common ground and avoiding points of disagreement.3 But Elena Kagan’s dissents are where her writing soars. Dissenting opinions are written by justices in the minority— the losers in a particular case. These opinions are less constrained because there is no need to hold together a coalition. They are meant to find fault with the majority decision, often with an eye to history. “Like good journalism, the best dissents are often colloquial, as if the writer were telling a story about the case to friends over dinner,” says Jeffrey Rosen, the legal editor of the New Republic.4

Elena Kagan’s writing is not brilliant because she uses fancy words and makes esoteric historical references. Rather, she uses the tools that I describe in my new book: clear, straightforward language; a coherent narrative structure; rigorous editing; and even humor if it serves to make a point. Justice Kagan cited Dr. Seuss (One Fish Two Fish Red Fish Blue Fish) in a 2015 case involving illegal fishing.5 She is one of only two justices in the history of the court to use the word “chutzpah” in an opinion. (Antonin Scalia, another great legal writer, was the first.)6

Ironically, great writing can be deliberately opaque. Former US senator George Mitchell played a crucial role in negotiating the agreement that ended the violent conflict between Protestants and Catholics in Northern Ireland, the Good Friday Agreement. Mitchell wrote in his memoir that vague language was essential to getting the final agreement approved. The parties had been at war for so long, and the various constituencies had developed such hardened positions, that no agreement was possible “unless the language was sufficiently elastic to allow it to be read differently by opposing sides.”7 The murky language in the Good Friday Agreement became known as “constructive ambiguity.” The prose was so convoluted in places that it spawned a joke: “What do you get if you cross the Northern Ireland peace process with the mafia?” Answer: “An offer you can’t refuse and can’t understand.”

Writing is how we give directions, file criminal complaints, compose love letters, report the news, pitch investment ideas, complain to our landlords, and undertake most other important life endeavors. Language is the code of life; writing is how we make that code clear and effective. Bad writing is like bad computer code: it obscures, confuses, and works against what we are trying to accomplish (unless unclear writing is essential to what we are trying to accomplish).

The spoken word matters, too. Franklin Roosevelt used language to assuage Americans’ fears during the Great Depression. His medium was radio; the tool was succinct, powerful, and inspiring language. Writing and speaking are two sides of the same coin; they both require using language to good effect. I have been involved with that coin in various ways for my entire career. Twice I have worked as a speechwriter, first for the governor of Maine and later for former Chicago mayor Richard M. Daley. Writing is always hard; putting words in someone else’s mouth is uniquely stressful. I recall a particularly scathing critique by the governor as he reviewed the draft of a speech. “Is this supposed to be funny?” he asked angrily. “Because if it is, it isn’t.” His word choice was clever, albeit devastating to me in that moment.

I worked for five years as the Midwest correspondent for The Economist, a British weekly news magazine. My job was to report on topics across the American Midwest and produce succinct stories, rarely more than a thousand words. Years later, I ran for Congress in Chicago during the depths of the financial crisis. I gave speech after speech explaining what I stood for as a candidate and why I ought to be elected. (I wasn’t.) I have worked as a columnist, using analysis and data and humor to try to explain complex topics like health care and tax policy, and I have written books on economics and statistics and monetary policy. I don’t know more about those topics than other academics; I have been able to write about them in ways that make them understandable and even enjoyable for lay readers.

For all that, what motivated me to write my new book, Write for Your Life, is my teaching. For nearly twenty years, I have taught public policy to graduate students and under-graduates, first at the University of Chicago and now at Dartmouth College. My students are invariably bright and motivated; however, many of them do not write well enough to thrive in a professional setting.

This should not be a great surprise. Most writing assignments in school are, by necessity, somewhat artificial: reports, essays, and term papers. That is not writing for the real world. Most people do not make a living by writing ten pages on whales or by describing the symbolism in Paradise Lost (with the obvious exception of nature writers and book reviewers).

Writing for life is different. It requires composing your thoughts in a way that gets your desired response, whether that is laughs in a comedy club, a raise from your boss, a large donation to a food pantry, or something else. This is a crucial life skill. As Upstart CEO Dave Girouard points out in his manifesto, “Poor writing can harm you in so many ways: logic is hidden, points are lost, news is buried, intent is misread, feelings are hurt, credibility suffers. And that assumes anybody actually reads what you wrote.” Remember, he’s not an English teacher; he runs companies for a living.

What kind of writing for life might you do? You might start a company, as Dave Girouard did with Upstart. How cool would it be to design crucial software for a self- driving car or to engineer a medical device that makes surgery safer and more effective?

Here is how you would get started: by writing your business plan. Long before your product gets to market, you will need to raise millions of dollars to fund your startup. You cannot do that by inviting investors to your parents’ basement and exclaiming, “Bro, you have no idea how awesome this idea is!” Rather, you will write a business plan that explains to investors in explicit detail how your product will work, how it will be different from related products on the market, who will buy it, how much they will pay, and, most important, what kind of return your investors will make if all goes as planned (and how much they will lose if it doesn’t). The most prominent venture capital firms get about a hundred business plans for every one they invest in. You might be thinking: The ideas that get passed up must be lousy. We don’t know that. What we know is that the ideas that get passed up are not compelling as described in the business plan.

You might have some modest suggestion for how the world could be made better: a new crosswalk near your home; a change in zoning laws; legislation to improve policing. How do you set those changes in motion? You write to the officials who are in a position to authorize or vote on them. Your letter or email will be stacked with hundreds of other ideas that range from sensible to insane. To move your idea to the top of that pile, you may circulate a petition or write an opinion piece for the local newspaper (both of which will require clear, succinct, compelling language). All political and social change is rooted in effective communication, from small projects at the local level to decades- long national movements.

When Martin Luther King Jr. was arrested in Birmingham, Alabama, in 1963, he wrote the Letter from Birmingham Jail. This was not a long complaint about the food. It was a letter to explain the purpose and value of his nonviolent civil disobedience campaign, particularly to white clergy who had been critical of his efforts. The letter is compelling enough that it was published as a pamphlet, reprinted in publications like Ebony and the New York Post, and introduced as testimony in the US House of Representatives.8

In 1995, Hillary Clinton gave a speech in Beijing at a United Nations conference on Women in which she famously declared, “Women’s rights are human rights, and human rights are women’s rights.”9 As I will discuss later, the speech was much more than one powerful line, but the overall effect was to reframe the way women’s rights are perceived around the globe. “It was Hillary Clinton’s declaration that jump started a global movement,” says Allida Black, a historian and founding editor of the Eleanor Roosevelt Papers Project.

Okay, you may not lead a social movement, and one hopes you won’t be incarcerated in Alabama. But you are likely to have a job of some sort. Every facet of that work will require clarity of communication: with your customers; with your coworkers; with your boss.

For ideas big and small, the quality of your writing will signal your clarity of thought. Harriet Miers is not currently on the Supreme Court; Elena Kagan is.

Your writing will sell others on your plans: Dave Girouard’s company Upstart went public in 2020 and was valued at roughly $1.5 billion.

And writing will play a crucial role in your overall success. The white clergy on the receiving end of Martin Luther King’s letter from jail became an important source of support in the larger civil rights movement.

Whatever you do, good writing will help.


Reprinted from Write For Your Life: A Guide to Clear and Purposeful Writing (and Presentations).
Copyright (c) 2022 by Charles Wheelan.
Used with permission of the publisher, W. W. Norton & Company, Inc.
All rights reserved.



Charles Wheelan is the author of the best-selling Naked Statistics and Naked Economics and is a former correspondent for The Economist. He teaches public policy and economics at Dartmouth College and lives in Hanover, New Hampshire, with his family.


1. Dave Girouard, “A Founder’s Guide to Writing Well,”$2unders-$2ide-$2-$2iting-$2ll/.
2. David Brooks, “In Her Own Words,” New York Times, October 13, 2005.
3. Jeffrey Rosen, “Strong Opinions,” New Republic, July 28, 2011.
4. Rosen, “Strong Opinions.”
5. Mark Joseph Stern, “Supreme Court Fish Case: Alito Saves the Day, Kagan Cites Dr. Seuss,” Slate, February 25, 2015.
6. Rosen, “Strong Opinions.”
7. The Northern Ireland examples were compiled by a group of Dart-mouth students in a class on the Northern Ireland peace process. David Brooks et al., “Insights from Peace and Reconciliation in Northern Ire-land,” Task Force Report, Fall 2014, 49, https://rockefeller.dartmouth. edu/sites/rockefeller.drupalmulti-$ _ireland_2014.pdf.
8. “Letter from Birmingham Jail,” April 16, 1963, Martin Luther King, Jr. Ency-clopedia, Stanford Martin Luther King, Jr. Research and Education Institute,$2rmingham-$2il.
9. Remarks of First Lady Hillary Rodham Clinton at the Fourth Women’s Conference in Beijing, China, September 5, 1995, com/watch?v=xXM4E23Efvk.

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