The #1 Lesson to Becoming a Brilliant Writer Revealed

What I learned from Joe was how to overcome writer’s block and let the words flow....

Back in the early 1970s a friend, Terry O’Connor, owned a small advertising agency in Lansing, Michigan. Terry and I put together a company to sell herbal teas, smoking mixtures, and potpourris and we ended up moving the company — which had started in my bedroom with Louise and me filling jars of tea by hand — into the old mansion built by R.E. Olds (the founder of Oldsmobile) in Okemos, Michigan.

The building, by that time, was in pretty bad shape, but Louise and I moved in there (our second child was born in that house) and Terry moved his ad agency in, along with what eventually became around 15 or 18 employees. Terry invited me to join his ad agency; he’d do the art if I could to the sales and write ad copy.

I was in my early 20s and this was my first exposure to the advertising industry. Ter Graphics had some large clients — Michigan National Bank and Kellogg’s, for example — so I went off on a search for the secrets of successful ads.

Back then Joe Sugarman was one of the most famous names in the business. In addition to running a successful mail-order company selling electronic gadgets, he also wrote the AdWeek Copywriting Handbook.

He could charge thousands of dollars to write a single sentence or paragraph for major national advertisers. And, as a favor to a friend from the old Donnelley publishing company, Joe had finally agreed to teach a weekend seminar on writing advertising copy.

I spent months saving the money to attend that weekend in New York, and it would be an understatement to say it just changed my life. It opened entirely new doors of opportunity to me.

The number one lesson I learned from Joe was how to write anything I’d like people to want to read, be it ad copy, a newspaper or magazine article, or a newsletter like this one on Substack.

“Most people make the number one writer’s mistake when they start,” he said, as I recall (and my memory of this is pretty vivid). “They think they’re talking to an audience. But there’s never an audience. Instead, people read everything from books to articles to ad copy one at a time. Each person is reading each word you write, sounding them out in their own heads, all alone.”

Therefore, Joe said, it’s essential to write in a style that’s personal and conversational. (There are exceptions, of course, like academic writing, but they’re few and far between.) And that’s where Joe’s little trick that I’ve found so handy throughout my life came into play.

“Think of somebody you know, you like, and who you think would be interested in your topic,” Joe told us. “Then roll a fresh piece of paper into your typewriter and put their name at the top, preceded by the word ‘Dear.’ Follow that with a sentence or two about anything that you’d normally write to that person about. And then tell them about your product.”

The example he gave, since he ran an electronics gadget mail-order business (JS&A Associates), was his Aunt Margaret, who he knew and liked but also knew was a gadget freak. He’d start out with “Dear Aunt Margaret,” and then ask how Uncle Harold and the kids were doing, along with a sentence or two about his family.

Then came the copy:

“But what I’m really writing to you about today, Aunt Margaret, is this incredible new product I came across when I was at the Consumer Electronics Show in Las Vegas. Imagine this, Aunt Margaret: you’re sitting in your living room and it’s so quiet you can hear the sound of traffic and faint conversation from the street outside.

“And then a wall of sound — Beethoven’s 5th Symphony — washes over your living room with such clarity that if you closed your eyes you’d swear you were in the front row of the Philharmonic Hall. It’s an incredible new digital audio technology called the “compact disk player” and I was able to pick up a few hundred of them from the manufacturer, so I can send you one for only $395.”

By writing his ad copy as a letter to somebody who met his three criteria, Joe discovered he could trick his brain from thinking (and writing) in a linear or technical way into a personal, conversational style.

He had us all practice it in the class, and I was astonished at how easy it became to produce ad copy that would actually work. It’s like re-programming your unconscious mind, flipping your entire perspective when writing from “here are the facts, this is it” to “let me tell you about this thing I know you’ll find amazing.”

But I hadn’t aspired to be an advertising copywriter my entire life; by the time I left my parent’s home at 16 I’d already papered the wall of my bedroom with 56 rejection slips from magazines for my submissions of poetry and short stories.

My parents were literature fans (they had over 20,000 books in our basement library where I carved out a bedroom among the bookshelves), my mom had her degree from MSU in English Literature and was an aspiring writer (of children’s books) herself. My dad was working toward being a history professor when I was born and he had to go to work in a steel plant, and he was president for years of a national group of antique book collectors. My Uncle King Saunders was a newspaperman in Charlevoix in the 1950s, and our family held him in awe.

In our house, there was no higher or more noble profession than being a journalist or author, so I’d been writing with publication in mind since I was around 10 years old.

So, when I got back to Michigan from Joe’s New York City seminar, I wrote an article about using raw licorice roots to stop smoking and used Joe’s strategy. I started it with “Dear Terry” and went on from there.

Terry was a smoker and we both knew it was killing him; he’d tried quitting dozens of times. (He died recently from mesothelioma.)

Licorice contains a stimulant drug called glycyrrhizin, which is reputed to make it easier to quit smoking tobacco because it pings some of the same receptors as nicotine (it’s also mildly addictive, which is why most licorice candy has been de-glycyrrhizinated), so I got a pound of dried raw roots, cut into 3-inch lengths, vaguely resembling woody cigarettes.

I presented Terry with the bag of roots and my article and, incredibly, six months later he’d been six months “clean” of tobacco and stayed that way the rest of his life (and chewed licorice roots for years). And I was hooked on this cool new way of writing.

Ever since then, pretty much every article I’ve written was written to one specific person. Although I’ve shared this story with him before in much shorter form, I wrote this one to Rohn Kenyatta, an incredibly talented writer who specializes in issues of race and politics, and has his own newsletter, LookingNWords, here on Substack.

Several of my books were entirely written to one person, sometimes even Louise or one of our kids, although for most I’ll write individual chapters to different people.

My spiritual autobiography, The Prophet’s Way, for example, is largely made up of letters (many never sent) that I’d written to friends, mentors, and family members over the years. My Hidden History books on Oligarchy and the Supreme Court were rather technical in their detail, so to make them super-readable I wrote different chapters to different people who I knew would be interested in the subsets of the overall story line.

I’ve been doing this so long that I no longer put the “Dear…” at the beginning; now I just visualize the person I’m writing to and start writing. It’s become largely automatic.

Which brings up the second big benefit of using Joe’s technique: it obliterates writer’s block.

I’m convinced that writer’s block, for most people, is a function of being intimidated by “the audience.” My HartmannReport.com newsletter, for example, is sent to around 65,000 people a day and the site gets over 2 million pageviews a month. I’ve given speeches before as many as 5,000 people, but two million is absolutely intimidating.

One single person — and someone I like, at that — is far less scary. It’s easier to begin a conversation with somebody you know, even if they don’t know it’s happening on your computer as you’re writing an article or blog post.

Something about that “Dear Ralph” and a couple of conversational sentences just washes away anything even remotely resembling writer’s block.

So, pick a person who you know, like, and believe would have an interest in your topic and get to it!