What Is “Trying!” All About, Anyway?

Trying! is just that: an attempt. I’ve been a professional writer, in one form or another, since the late 1990s, but in the last few years, as the freelance world (and its paychecks) contracted, I mostly stopped writing. Trying! is a way to force myself back into the thing I love, and that I probably do best.

On a more basic level, Trying! is essays. (And essayer, in French, means “to try.”) In its current phrase, which began November 1, 2024, I’m writing one every single day (including weekends!), and generally publishing them at 10:03 a.m. ET. They are about, well, everything in life, or in my life: anger, travel, food, writing, friendship, Luke Skywalker, billionaires, the fundamental unfairness of life, dogs, cats, sausages, memes, Judaism, and Anthony Bourdain. I keep a running list of shorthand topics, but when I sit down to write, whether it’s after dinner or early in the morning, I rarely know what I’m about to create. It just happens.

With each of these, the goal is to make something that is:

1. Well-written: I care about words, sentences, paragraphs, structure, and I want you, my readers, to care about them as much as I do.

2. Thoughtful: Whatever topic I take on, I really want to consider it as deeply as I can, with generosity tempering my natural inclination toward snark.

3. Provocative: I don’t mean this in the sensational sense, though there is certainly some of that. It’s more that I want to make myself think in new ways about the world, and I want the essays to do that for you as well. If I’m just rehashing conventional wisdom, why should either of us bother with it?

After the essays, the newsletters often conclude with a section called “It’s Good and I Like It,” which I created to recommend things—books, foods, places, whatever—because some people thought I was being too negative about this shit world we live in. So there!

Trying! is also an attempt to fight back against the tyranny of “best practices.” In the world of Internet content, and especially the current rage for newsletters, there’s this sense that you need to be focused on a narrow range of topics, and provide something useful, something tangible and actionable, for your readers. You’re supposed to glom onto newsy angles and understand the trends people are googling. But I do that crap in my day job. Trying! is about worst practices. I want to make something beautiful and enjoyable and intriguing that lives outside of the LinkedIn-optimization industrial complex. I don’t know if that appeals to anyone else in the world, but I’m here to give it to them, whether they want it or not.