Peter John McLean

Writing to Entertain (Writing)

Any idiot can teach something. Well, maybe not gym teachers, but everyone else can. The problem with just aiming to be informative is that no one really cares about it. There is such a surplus of information available that simply solving a problem is almost never enough (the exception being if you are the first and only person to solve the problem or teach whatever you are teaching – in which case you can be as dull and boring as you want). However, if you aren’t the only person in the world who knows how to do something then you have to make your material better than the competition.

How the hell does someone do that?

By being entertaining.

One of my favorite examples is International Master Jeremy Silman, a chess author who sells an insane amount of books. I own quite a number of these books and have used them to improve my overall game. I will probably buy more of his books in the future to continue learning from his expertise.

And he isn’t even a Grandmaster. Before all the serious chess nerds come out of the woodwork to point out that based on his chess rating and skill he probably could have become a GM let me explain – I’m not saying that he isn’t capable of earning the title I’m just saying that he doesn’t have it and STILL sells a ton of books. People regularly turn down the opportunity to buy more prestigious texts from higher rated chess authors to instead read Silman’s books.


Because Jeremy Silman knows how to communicate with a reader, make them understand a concept, and do all of this without sounding dry and boring. His books are enjoyable to read (at least if you’re a chess geek like I am). People rarely seek out the most all encompassing guide to anything – because it’s frequently too dense to appreciate. Instead, people seek out resources that are entertaining AND informative.

How to Write Entertaining Copy that Makes People Like You

  • Have a voice. This is the single most important aspect of all good writing. Whether you write political commentaries or teen vampire seduction advice you have to explain the material in a voice that is authentic. If you lack any voice at all they won’t connect with you and will seek something more vibrant to learn from. (The obvious exceptions are journalism and academic/technical writing, but if you are writing in those categories you probably already know that and wouldn’t be reading about how to entertain readers. I spend enough of my time sifting through medical journals to know that they are never entertaining.)
  • Meditate on what surprised you and what you wished you had known. Too frequently do articles get put out that inform in a humdrum step by step manner as if the reader is a blank slate just soaking it all up. In reality most people that trip over your information are probably already somewhat aware and somewhat confused – so unconfuse them. Start your article with the most important thing you learned or the single most important thing. Imagine that you aren’t just writing an article about how to apply common stock evaluation metrics to a homebuilt castle of toothpicks but you are trying to teach your best friend how to evaluate his actual toothpick castle. He has a giant castle of toothpicks in his house and wants to sell out. What is the Initial Public Offering? If you read this article carefully you’ll see that the basic organization of it is similar to what I would have told my friend if he wanted to know how to write to entertain people. I’d start with the same snarky line, “any idiot can teach” and then explain what makes IM Silman’s books sell off the shelves. Then I would tell him to work on developing his writing voice and to be confident enough to write using it. Then I would tell him to imagine he was teaching me instead of some stranger. See how that works?
  • Don’t be afraid to have a sense of humor and accept that not everyone will get it. Some people will read my joke about stock evaluations of a toothpick castle and comment that it was “distracting” or “unnecessary”. That’s fine. Some people just won’t find your humor funny and maybe they won’t come back to your blog. That’s ok. Other people will laugh and come back to your blog specifically because they appreciated your personality. And those are the readers that you want.

Have a voice, consider the reader’s problems before you write, and have a sense of humor.┬áThat is all it takes to write stuff people actually want to read.