it's all writing! 003: Josh Gondelman
A comedian and the nicest guy on the internet on mucking through your thoughts until you get to the good stuff.
Over the course of my writing career, there have been a number of people who are both constants and constantly impressive in their sheer output. For my first job, I was very lucky to get a crash course in writing-for-the-internet at the kind of content farm that let us be truly weird as long as we hit monthly traffic goals — and while that freedom was a gift in its own way, so was the opportunity to connect with some of the most creative and prolific and inventive people I’ve ever met.
Josh Gondelman is top-three of that list, by a cosmic mile.
Josh is also the nicest person you’ve ever met — the number of times I get a text “hello” from him just because he wants to check in? and he means it? is staggering. And Josh checks in on all his friends this way. I am not special here, though he would say I am. He would say we all are, and that’s because he is, too. (Does that make sense? I’m writing first and editing never, it’s already been a long week.) That kindness radiates out of his writing, making it all the funnier and all the more compelling.
Given Josh’s very long list of writing priors — including a book, his various stand-up specials, an IMDB page that impresses even my brother, funny and incisive cultural commentary across a number of publications, and a truly marvelous newsletter — it’s very clear that he was born to write, and that writing shows up for him in a million different ways.
As I navigate what it means for me to be a writer, even and perhaps especially during the weeks when the most I have to show for my writing is like, this newsletter or a Word doc that I am the only one poking around in, it’s nice to remember that there are infinite ways to be a writer, and infinite ways for words to reach the right people. It’s not always about cranking out book after book after book (though if you’re that prolific, congratulations to you) — it can also be about exploring your own creativity across formats and genres. That can make you a stronger writer overall, whether through nuance or brevity or simply the fact that you’re showing up to a page every day and writing.
Josh Gondelman: Brooklyn, NY; Writer, comedian
Where are you online? Substack and also @joshgondelman on Instagram, BlueSky, and TikTok! You can also watch Josh’s new stand-up special, Positive Reinforcement here.
1. How does writing show up in your work, and your everyday life?
Outside of writing for myself as a comedian and for various pages and screens, I'm a huge texter. I love a bit over text. I think any time you are putting words down where someone (yourself included) can see them later is an opportunity to be expressive and interesting and intentional. Not to be all Manic Pixie Dream Writer, but even leaving a note to say you went out to get a sandwich is a chance to add emotion and subtext. Obviously a lot of the time it's just like: "Train delays. I'm running five minutes behind." But it can always be something more fun or more vulnerable!
2. How did you find your voice? Is this a thing you're constantly working on?
It took me a while even just to calibrate my literal speaking voice onstage and sound like myself. I started really young and I don't think I was fully myself yet. Finding my voice as a writer took really growing up and figuring out who I am as a human being, what I believe and value. Doing a lot of reading and writing helped, obviously. And writing in the voice of other people for television was instrumental too. It showed me both how I can inject my sensibility into a format where I'm otherwise invisible, and what I'd do differently that makes me ME. I love newsletters as a format because you really get to see people's specific fascinations and style choices. Great writing usually requires the outside eye of an editor, but lots of really exciting stuff comes from someone being left (more or less) to their own devices, and certainly not having to adhere to the house style of a larger institution.
3. Do you use writing in a way that surprises you? Does your work require more or less writing than you anticipated?
I would say the amount of writing in my career is what I expected and hoped for (lots!), but the amount of stuff that's NOT writing is way more than I anticipated. Does that make sense? There's so much strategizing what to write next! And waiting! And complaining! Plus, there's much more performing than I had counted on, which is so goofy to say because I have been doing standup for 20+ years. It just took me a while to consider myself a performer onstage and even on podcasts and such. (As a high school kid I did a lot of theater, and after one show my grandmother told me I was "really more of a writer." So, it wasn't just me coming to that idea on my own.) I got into it all for the writing, but I eventually came around to admitting that I also do non-writing or writing-adjacent things too.
4. What does your editing process look like?
There's definitely a brief period of stomping around and refusing to open the document/listen back to the words I said that's part of it. Then I try to slam through the easy edits first, eliminating redundant words and fixing typos to build up the momentum to take on bigger structural issues. I try to be good about reading things out loud, but sometimes I get a little too attached to how things sound in my voice (lol). Often times I ask my wife (who is a brilliant writer and editor) to read over things before I turn them in. Lately I've been working on a writing project with a friend, and we've been looking over things together and checking each other's work, and that's been SO much fun. I love a good collaboration! I honestly love a first draft and MARVEL at people who take great pleasure in the fine tuning process of an edit. It's like meeting someone whose favorite part of dinner is doing the dishes. But there is a real satisfaction to fixing a phrase or a passage so it comes out just right!
5. How has your relationship to writing changed over time? What did it once look like? What does it mean to you now?
I used to be so hungry to produce and publish and be SEEN and ACKNOWLEDGED. Now I'm a little more tentative to put things out into the world. Working behind the scenes on bigger projects that other people are the face of is always such a thrill, but it also means I can get out of practice doing things as just me. Plus, I think the culture of online commenting and engagement has fully become, like: "People are allowed to say whatever right to your (digital) face and that's part of the gig now." Which I don't love! I enjoy smushing words together so much, and I'm constantly tinkering with how important it is for me to be creating and releasing work that points right back to my big ol' mug.
6. Do you ever read past things you've written? How do you feel about them? How do you know you're growing as a writer?
I do, occasionally! Sometimes I roll my eyes at myself, but other times I'm really impressed and delighted with something I'd forgotten I wrote. (Humiliating to admit?) It feels similar to looking back at any version of your past self, where there's so much you'd do differently (Why did we all wear those pants that dragged on the ground???) but there's a lot to have affection and sympathy and appreciation for. Growth is visible when I look at something and think "Oh, I could do this better now!" or even "I wouldn't take this on now." It's (usually) only mildly embarrassing!
7. What's your ideal writing practice? How far from or close to that is your most realistic process?
My dream writing day is having a project I want to work on from 10am-2pm or so and then goofing around the rest of the day. Goofing around could entail coffee with a friend or watching a movie or even another creative project that isn't my big of-the-moment endeavor. Sometimes I land right in that zone. And other times I have to do MORE work than that (yuck) or I take on other obligations that prevent me from being as productive as Ideal Me is (which can be fine too). I try to be proactive and diligent without kicking myself in the ass any day I sleep late or have to run an errand or take a flight that pulls me away from work.
8. What do you think people get wrong or misunderstand about writing? What do you wish they understood about it?
Too many people (some writers included) treat writing as (predominantly) channeling a flicker of divine inspiration into work rather than the practice of thinking and feeling and putting those human experiences and impulses into words. I wonder (and I'm freestyling here a little) if that's part of why there's so much hype around generative AI. Going from nothing to ANYTHING seems so impressive when you discount that the goal is to create something GOOD and EXPRESSIVE and SPECIFIC. Even putting aside the plagiarism aspects and the environmental impact of the technology, it's just a complete misunderstanding of what writing is to value having some bullshit done NOW as opposed to something thoughtful done WELL. If you think of AI as computerized inspiration instead of circumventing craft and critical thinking, it's a lot easier to look at it as software that does something ineffable rather than an end run around the actual thing you're (purportedly) trying to accomplish.
9. What has writing taught you about yourself? About other people? About the world?
I learn more from other people's writing than I do my own, but writing standup specifically really makes me think about how an idea that seems so clear in my head can take sooooo much massaging to get across to an audience. That part can be frustrating but also really exhilarating too. There's something magical about having a weird and unrelatable thought and then through sheer force of words getting a room full of people on board. Sometimes you can sneak an idea into strangers' brains without their realizing, or even better, trick them into thinking that you are very smart and insightful.
10. What is the piece of writing you're proudest of? How did you think of the idea, and what did it look like to bring into the world?
This is such a dopey, easy answer, but I'm really proud of my essay collection. I came up writing for the stage and for the internet, where speed and voice were at more of a premium, and I'm so glad I made myself sit down write an entire book! I don't do well writing in a hole with no feedback, so it was uncomfortable, but it was extremely rewarding. I do feel a little like a dumbass saying I'm most proud of the thing with the most words in it, but it took a lot of time and effort and patience. Shout out to my editor Stephanie who was wonderful to work with and would always tell me when I was making too many jokes to avoid having feelings.
Rapid Fire:
Favorite Book:
I've still got to say Infinite Jest like some kind of asshole!
Favorite Song Lyrics:
Throw a dart at a printout of the words to the Hold Steady's album "Stay Positive" and you'll probably hit one.
Favorite Quote:
“If I am not for myself, who will be for me? If I am only for myself, what am I? And if not now, when?” - Hillel the Elder
Favorite Writer:
Maris Kreizman <3 [Ed. note: Awwww! Also, correct answer.]