The Art and Skill of Making Yourself Miserable

Some satire to make it a good day.

A Journey with Dan Greenburg, author of "How to Make Yourself Miserable."

"Imagine a world where happiness is greatly overrated, and the true path to enlightenment is paved with self-induced misery. In his uproarious satire, How to Make Yourself Miserable, Dan Greenburg invites readers to take this road less traveled and master the art of making themselves absolutely miserable. And let's face it, who among us has not on occasion indulged in a little self-sabotage?

It's a tongue-in-cheek manual that stands the self-help genre on its head. Greenburg's book offers no wisdom about improving our lives. It gives the reader a generous toolkit for amplifying our worst tendencies. It's like a playground of reverse psychology where the swings only go in one direction—down—and the slides never end. And, surprisingly, it's an absolute blast. Oops, I shouldn't write that. It might make you feel good.

Greenburg's uncanny ability to highlight the ridiculousness of our typical worries enhances his satire. From fixations over imperfection to over-analyzing, keeping one up into the wee hours of the morning, Greenburg knows our darkest, most irrational thoughts—and he's not afraid to laugh at them.

For instance, in his chapter "How to Become Neurotic," he gives foolproof techniques such as comparing oneself with those people he meets who are not the same or stressing about things that probably will never happen.

And I have a complaint for Dan. He should have consulted me about that chapter. I'm the foremost expert on being neurotic.

It is as if Greenburg is trying to get the reader to identify such absurd conduct in themselves, and we can't help but laugh at our own absurdity.

The humor is sharp, witty, and often self-deprecating, and it will never make Greenburg shy away from pointing out the hilarity in our shared human experience. He blows up common anxieties and insecurities with great acuity to take them to the point beyond reason, whereby we all can laugh at them. It's almost as if he puts a funhouse mirror on our fears, distorting them just enough that we find them comical instead of crippling. (darned)

One of the most entertaining elements of How to Make Yourself Miserable is its interaction. Yes, Greenburg goes the extra mile to provide activities that will help you immerse yourself in misery.

The "Mirror Gazer's Guide" challenges you to scrutinize each wrinkle, blemish, and flaw—you will leave the house no longer feeling good about yourself. Another fine-honed skill of mine.

Or the "Worst Case Scenario" game, where you can spend hours imagining the most catastrophic outcomes for even the most mundane situations. My grandparents were excellent at this.

These exercises amount to a brilliant parody of the self-help genre's obsession with the quiz and self-assessment, only this time, the turn is delightfully dark.

So, underneath that lightness of humor, Greenburg's book offers a commentary on the absurdity of our self-imposed anxieties. He suggests how ridiculous they are and encourages us to indulge in our worst habits. It's like eating too much candy, which is fun at first, but after a while, you realize it isn't the best idea. In this sense, through laughter, Greenburg lets the reader see the pointlessness of our anxieties and helps us get over them.

In short, How to Make Yourself Miserable is masterful satire. In this book, Dan Greenburg turns the whole self-help category on its head. The result is a work as funny as it is bright. Most of all, it is an invitation to find laughter in one's fears and insecurities. Thus, this is the book for anyone wishing to learn how to wallow in self-pity in style.

After all, Greenburg would probably encourage you to make it worse next time—just for the fun."

Sadly, Dan Greenburg died at the age of 88 in 2023.