By Josh Gondelman — 06 Oct 2025

#152. Time Sensitive Reader Pep Talks

Now that's what I call Judaism Volume 5786.

Hi everyone,

Did you know that it's nice to be around people with shared values to celebrate or mourn collectively? Did you know that???

On Friday night I had the good fortune to get to pinch hit for my friend Faith Salie (off on assignment for CBS Sunday Morning) and host the yearly benefit for Foster Pride, an organization that provides mentorship and scholarships to young kids and teenagers in foster care. The event raised over $100,000 (hell yeah!), and I even managed to successfully ingest a dinner-sized number of calories from passed appetizers alone. Although I did have the experience (and not for the first time) of...still hungry...still hungry...still hungry...whoops I've eaten 17,000 arancini balls. The event was held in the Phillips gallery on Park Ave., and as part of the event, I got to take a little tour and learn about the photography of Irving Penn. I now know TWO things about Irving Penn that I cannot wait to deploy at parties when someone brings up Vogue magazine, fashion photography, cropping pictures, or negative space. Look out, art world! Here I come!

I also met the artist Christine Sun Kim who was being honored at the benefit and generously donated a piece of her work to the auction. It was really cool to see Christine–who is deaf–talk about the inspiration for her work and also the importance of accessibility in arts education. As we were meeting, before I realized that she communicated through ASL and an interpreter, I did grab and vigorously shake her hand as she went to sign hello. She was incredibly gracious about it, but my misstep will haunt me until I die, obviously.

I've been doing arguably too much drinking with my friend/collaborator/consistent newsletter fixture Alison Leiby as we wait for professional news on a project we created together. But amidst that, we hosted a Sup, Bro? show at Union Hall, where everyone crushed, and I saw many friends I hadn't seen in a long time. I stayed out way too late with Leiby and Bryan Cook, a writer for Jimmy Kimmel Live. Bryan went up first on our show and went so fucking hard during his set talking about how evil ICE is and all sorts of other righteous stuff (in an extraordinarily funny way), and the crowd loved it. Everyone brought such specific and vivid comedic perspectives to the stage, and I just felt so energized and also SO drunk by the end of the night I don't know if I said that already, but once again...whoops.

Frankenstein's Baby lineup for Monday 10/6 featuring Sydnee Washington, Hari Kondabolu, Samantha Ruddy, Aaron Chen, and Lauren Davis! — It's a great lineup and also Aaron Chen is so funny on Fisk!

Alison and I are hosting tonight's Frankenstein's Baby also at Union Hall where I will be much more temperate, I swear (especially because we did karaoke last night too). This show will also be great.

At the beginning of last week, I had kind of forgotten to make Yom Kippur plans, but Maris found a big outdoor Yizkor service not far from our apartment put on by Rabbis for Ceasefire in conjunction with Jews for Racial and Economic Justice as well as a few other progressive organizations. Speakers included a small group of lefty rabbis as well as NYC comptroller (pronounced "controller"...what the fuck?) Brad Lander and public advocate Jumaane Williams as well as author/activist/poet/therapist Hala Alyan. I'd been considering watching the livestream from home, but I'm glad Maris wanted to go in person because it was good to be amongst hundreds of Jews communally feeling the gravity of the holiday tradition, as well as standing together to speak out against the way the state of Israel has been massacring Palestinians and ignoring the pleas to end the slaughter and bring back the living hostages peacefully.

Hala Alyan speaking at a Yizkor service in Brooklyn surrounded by rabbis with some onlookers. — Look at all this damn community!!!!

I sometimes feel so destabilized by what reality looks and feels like these days. Constant intrusion of useless AI into our lives. American support for relentless violence across the world. Brutal repression of immigrants within our borders. The entire economy benefitting 500 rich sociopaths while everyone else flounders. You know, the usual complaints and dismays.

Sharing physical space with people whoa feel similarly is so comforting (oh good, I haven't gone insane) and inspiring (together maybe we can make things better). It's a lesson I re-learn all the time, and I'm really grateful to have had the opportunity to be reminded this week by such passionate, thoughtful people.

I know I've been tipping a little bit towards the sincere in these newsletter intros, but the news has felt so heavy recently that I haven't felt good about ignoring it or trying to add much levity to some of the horror.

But on the other hand, while we're here, I will say: It's funny that Taylor Swift's new album contains a song where she sings about boners the way Steve Carell talked about boobs in The 40-Year-Old Virgin. I find it kind of charming! Thanks for reading!

MORE STUFF

It was a big week for podcasts and the like over here. How about a little rundown?

I made jokes about the news with Andy Zaltzman and James Nokise on the most recent episode of The Bugle.

I explored the paranormal with Roz Hernandez for Ghosted.

My pal Luke O'Neil and I ranted about being the coolest and best fans of the New England Patriots (and why that's such a weird thing to be) on Dan Hopper's podcast Thrill of Defeat!

I really went deep with Alex and Drew on the Into the Mud podcast about feeling stuck between working in traditional entertainment and the need to do independent outside projects as the industry crumbles.

Oh and! The pilot reading I did with a bunch of great hilarious friends is now online for your viewing pleasure! It's a great script by Jeremy and Phil, and I really laughed a lot at the great performances from the whole cast. It's got kind of a fantastical plot, and it's full of jokes! Please enjoy The Chronicles of Trevor!

One little heads up: I've got FOUR SHOWS IN NEW ORLEANS 10/24-10/25!!! I'd love to see you there if you're around! I'll be on the west coast for a few dates late this year/early next year so stand by for that info too!

TIME SENSITIVE READER PEP TALKS

I got a few pep talk requests that would have expired if I let them sit, so I'm going to do a little speed run through a few!

I’ve been training for a marathon for months and am now suffering an injury and might possibly not be able to run it. It’s two weeks away and is a 50/50 chance at this point. Entry, flights, hotel all already paid for and my partner is doing it. We trained together and wanted to do this together.
- Taking It In Stride?

First of all, best wishes for a speedy recovery as well as a recovery of your speed!

One of the few things I hate more than running is when best laid plans are destroyed by cruel twists of fate, so I am able to sympathize with your plight, but it was a photo finish. (Jk I am very much on your side here!!!)

Obviously, your long-term health is the priority here. And, as much as it stings to have blown this money if you can't participate, it was an investment in the experience itself and not something you expected to pay off in any other way. (Meaning, it's not like you spent all this money on a trip to the set of Shark Tank and now you can't go and pitch them your idea for a sponge on a stick that is the exact right size and shape for cleaning out a car's cupholders.)

Still, this is a major league bummer! Worst case scenario is that you sit this marathon out, which is such a disappointment, but also...most people don't run a marathon most days, and as long as you're on the path to recovery, this is a mid-sized, Toyota Camry kind of setback. Maybe you can run at a slower pace than you expected which is ALSO okay. Marathon running is the ultimate you-versus-you sport, and you're not racing against the you of a month ago, you're racing against the you that's been sidelined for a little bit. Very different adversary. It's possible you'll be back to full strength and top speed in two weeks, and that would be good in a way I don't need to explain. Readers, let's all cross our fingers for that outcome.

Even if your worst fear comes true, you will still live to run another day! The money you spent is an investment in your future. The time on the couch is the same. You can get yourself back to where you want to be. Despite the assertions of Bruce Springsteen, we were not necessarily born to run, but you have made yourself a runner, and no one can take that away from you!

Hello Josh. Getting my first colonoscopy on Wednesday, and it’s the first time I will go under any sedation since I was 8 years old…and the whole thing is seriously stressing me out in advance! And I haven’t even got to the drinking the awful stuff and pooping a lot part!
Signed,
Scared Shitless

Okay let's start at the bottom (pun very much intended) of your list of concerns. As (I think?) my friend Sam once sang in high school (or maybe it was Gorman in college?), paraphrasing R.E.M.: Everybody poops...soooooometimes. It will be unpleasant to aggressively empty out your insides like you're a travel toothpaste tube on the last night of a ten-day trip, but there are worse fates.

In terms of the sedation, I totally get that fear. Whether it's done medically or through more UFC-type means, it's weird for someone else to make you go to sleep. Sleep is something you do to yourself through overscheduling your days past the point of reason or physical exertion or finally trying to watch that movie you've been meaning to watch at the end of a long week, but your couch is just so comfy.

However, until we further ensmallen medical technology, this is the best we've got. The ass, as they say, is the window to the hole. Capable teams of doctors do this all the time with reliable and positive results. You are not, as far as I know, getting some kind of back alley colonoscopy where a med school dropout smothers you with a chloroform-soaked rag and then shoves a Kodak digital camera up your butt. You're in good hands! This is a weird thing for you to experience because it's new, but it's completely normal for the people performing the procedure! You've got this because they've got this!

I would please like a pep talk about currently living with my parents, husband, two dogs, and two cats. In two weeks we will be in our own home, but for now, it is a little nuts!!!
- Holding Down the Fortnight

There are many things that are impossible or unbearable to do for two weeks. You can't hang from a greasy pole suspended across a rushing fiver for fourteen days. You can't leave leftover sushi exposed on a countertop for half a month. You cannot survive in a hippopotamus enclosure for the time it takes two new episodes of The Morning Show to air. These acts would require superhuman strength, endurance, or ability to cultivate meaningful friendships across species.

Your task, surviving a couple of weeks in a 70s-sitcom-ass setup with your family will not be easy. But it is certainly possible. And while you are at risk for several days of stress, and a strain on your relationships with people you love. That's not ideal. But it is not the same challenge as spending two weeks trying to build a bomb shelter out of toothpicks or drain the Pacific Ocean with a mop bucket.

Much like a bad haircut, this is going to be a tough little while, but then it will improve drastically. The bad times will be but a memory, and in this case, you won't even be able to tell how gnarly things got by looking at pictures. You're almost there! Keep going! And do NOT mess with your bangs in the interim.

PICK-ME-UP SONG OF THE WEEK: Amanda Shires - "Lately"

Amanda Shires put out a new record called Nobody's Girl, which is very good and also very much about divorce and loneliness and looking back on a situation that doesn't sound great. And while "Lately" fits cleanly into that paradigm, it's also about doing the work of trying to feel better. "How am I doing? I don't know..." the song's opening line, could apply to any one of a hundred people I know. Like, what the hell is even happening lately? But climbing back on top of your own life requires effort and intent, and even though "Lately" isn't about reclaiming one's own peak, it's a beautiful testament to the importance of giving it an honest shot, whether that means going out with friends or sitting at home listening to Billy Joel, fighting the blues with more blues (her words not mine).

This record is on my radar thanks (once again) to friend of the newsletter Natalie Weiner's great profile of Shires for Texas Monthly. Check that out too!