Sometimes Writing Is Hard

When I sit down to write these essays, sometimes in the morning, sometimes after dinner, I never know what I’m going to produce. I keep a long list of potential topics in an Apple Notes file, and almost all of them are in shorthand, rarely more than just a couple of words. Addicted to the end. Karma chameleon. Persian cucumbers. Mohels. That’s all I need, usually, to get going for two hours and 1,500 words. If you’ve been reading Trying! for a while, you know where that leads. If you’re new, well, today is a bit different from that.

And that’s because tonight—last night, technically—I sat down at the computer, after a lovely dinner of Italian-style braised pork butt (rosemary, red wine) and macaroni and cheese (Gruyère and raclette), and just felt… nothing. The topics on my list looked old, uninspired. Well, that’s not fair: Many of them I’m still quite excited about, but they require more work—more research, reporting, and preparation—before I can even begin to tackle them. The easy, riffable topics, though? There just didn’t seem to be any worth addressing, none that captured my attention or made me feel as if I might have something original to say. Usually, once I start writing, I forget about the late hour and the efforts of the day and whatever has been plaguing my mind. Right now, though, all I feel is tired. Maybe I’m the one who’s old and uninspired.

I suppose this was to be expected at some point. Today marks Day 66 of Trying! That’s 66 essays, or about 100,000 words conjured out of my head and sent out to all of you at 10:03 a.m. ET almost every morning. (I’ve been late a few times, I know. Sorry!) I haven’t taken a day off, and I don’t intend to at least until I reach 100 days. That’s a lot of work, and if it were anyone other than me, I would not be surprised by a brief break in the program, or a dip in the level of energy. This is me, however, so I’m not sure what to make of it.

I won’t, however, call this “writer’s block.” To me, writer’s block signals an inability to get the words, sentences, and paragraphs out—to know what should come next and then to make it come next. It’s sitting at the computer, knowing what you’re supposed to do but unable to do it. This is not that. I don’t have any issue writing this word and this word and this word, and then launching into a new paragraph that will build on this idea.

Because the words and the sentences and the paragraphs still come easily. They have now for years, maybe since—let’s carbon-date this!—2007, when I really found my groove as the New York Times’ Frugal Traveler. That year I wrote dozens of articles for the Travel section, going from Darjeeling to Verbier to Bulgaria to the Caribbean, with a 14-week summer road trip across the United States. I was on the move all the time, with rarely more than a day to turn my experiences into prose, and so I just did it, as speedily and craftily as I could. Along the way, I figured out how to lead with a compressed anecdote, how to nail the nut graf, and how to build in enough dramatic tension to keep you reading till the kicker. And I did it again and again and again, with relatively little back-and-forth with my editors—one of whom was notorious for futzing with writers’ work—before the pieces were published. 2007 was the year I came to understand the magic formula and really became a professional writer, unblocked forever after.

I assume this is what all professional writers have to go through, in one way or another. If you’re going to be doing this as a job, you’ve got to learn how to make the words spill out, whether they’re brilliant or workaday. You’ve got deadlines to meet, and other people relying on you to meet them so they can meet their own deadlines. It’s deadlines all the way down. If you’re struggling just to squeeze out the next sentence, this is going to be a tough business for you—and it’s already pretty damn tough.

Or maybe I’m just projecting! Maybe writing is really fucking hard all of the time, for everybody, and I just didn’t understand that I was riding a lucky streak that has now, sadly and predictably, come to an end. Maybe the block is normal, the topics are always dull, and I’ll struggle—we’ll all struggle—to make it to Day 100.

I mean, I obviously don’t think any of that is true. But it might be!

Which is why I want to hedge against that possibility with a few proposals:

1. Send me your prompts! I love getting hit with ideas from the outside, and making them work. Many pieces were inspired by reader prompts, including this one and this one and this one. So email something over!

2. I want guests! Would anyone be interested in writing a guest essay? It could be anything from a riff of a few paragraphs to an It’s Good and I Like It segment to a full-fledged essay.

3. Have I written something you absolutely hated? If I’ve written something idiotic, evil, or merely misguided, I would love to hear about it in detail! Then maybe we can find a way to turn that hatred into something new and interesting—a Q&A or dueling essays or maybe a live Netflix boxing match.

Don’t worry: I will still keep producing the daily essays that you and so many cherished paid subscribers eagerly read every morning. And the coming week should have a few pieces I’m very excited about. (Not mohels, alas—I haven’t figured that one out yet.) But as much as I love writing them, I want to be careful not to write myself into a trap, where I allow myself only to do one thing, the same thing, day after day. This newsletter format allows us so much freedom, it would be dumb to restrict it to a single approach. This newsletter, remember, is called Trying! If I don’t keep experimenting, I’ve failed already. 🪨🪨🪨

It’s Good and I Like It: Tourists Welcome

I’ve been all around the world, and there are very few hotels I can say I truly love. But Tourists Welcome, in North Adams, Massachusetts, is one of my absolute favorites. Up in the northern Berkshires, down the road from the MASS MoCA museum, it’s the ideal combination of coziness and style, with big, bright rooms (and cool bunks for kids), a lodge I actually want to hang out in, and lots of hiking trails right behind the property. Honestly, I would go there just to go there. I love it.

Read Yesterday’s Attempt