I’ve been on Substack for eight years. Eight!
Every so often I have a fresh go at playing the Substack game, trying different formats and types of content. I’ll post humor or lists and once attempted an advice column. I’ve done AMAs (which I forgot about until just now). I often beat myself up over this process, believing it’s embarrassing to show your whole creative-and-strategic ass in public. But you have to actually try things not only to see if they’ll work, but also to figure out how you feel about doing them. In putting the focus primarily back on personal essays with a smidge of cultural what-have-you, I feel like I’m back in the right place for now.
Over the past two weeks I’ve been in a process of rebalancing and reprioritizing the demands in my life and on my brain and resources. Some of those reassessments were forced upon me and others came through opportunities. Either way, getting clear has been a massive relief during a year where I’ve had precious little in the way of relief or clarity.
I was walking my dogs yesterday when I was thinking about being on Substack for eight years and suddenly had the thought “I want to retire from Substack at ten.” It sort of made me laugh because Substack will likely be the only thing I’ll ever be able to retire from. This is also assuming Substack will still be around and/or hasn’t blown itself up by then.
I’m setting it as a goal, I think, because instead of diversifying I want to move more intentionally toward focus. I’d like to believe that by the time I hit that ten-year mark, I will be fully in my life here. I’ve also been feeling a desire to be less known, not more. To work things out less publicly and to just be less thinly spread in general. Everything I write or do requires promotion currently. I’d like to move away from that, if it’s ever possible. I’ll be 60 then. Seems like a good round number to wrap it up. We shall see, of course.
Although it’s felt good to be focused more on personal essays for now, I also know that my most recent ones have been long as Hell. As if I hadn’t known that from actually writing them, people love to tell me anyway. Damn that was long! I read the whole thing! Brother, this is not Everest. You do not need to climb it. I’m just over here in my ever-shrinking corner of marginally paid writing on the internet, trying to manage my feelings.
But! Even I need a break from all that.
These sort of lists and recommendation posts—when I do them infrequently and not as some sort of “content strategy”—always scratch the itch I have for sharing. Sharing and over-sharing are what brought me to writing in the first place a little over a decade ago. I just logged into my Medium account for the first time in years, where I first started writing in public and had my first run of viral hits like “When Will It Be Time’s Up for Motherhood and Marriage?” and “How to Talk to Your Kids About Bernie Sanders”. I was reminded that beyond personal essays, this is where the little seeds of opinion and humor sprouted up and were rewarded.
So, for now, some humor, some opinion, and a bunch of sharing.
I wrote about being back on the road again in June and the hallucinatory insanity of not being able to find water or switch drivers or afford anything. I wrote about being quite good at my job, actually, but not being able to find work (update: I am now working! There is work coming in! Most of that is due to people I know reading this newsletter! Humiliating! But also yay!). I wrote about how demolishing it’s been to realize that I accidentally divorced myself from the life I knew by moving, by doing something I absolutely needed to do personally and professionally but also how bruising it’s been emotionally. And most recently I wrote about love, romance, nostalgia, hope, a dash of JFK Jr., and a first date 30 years later.
🌞 Currently in my summer arc.
🌞 I’m done writing about Cookie magazine so I’m looking to rehome my entire collection ASAP. Several people reached out previously to take them before my move but I’ve since lost track of anyone who wanted them :( Priority given to anyone studying and/or writing about media, motherhood, influencing, and related topics. You just need to pay shipping! Reach out if you’re interested.
🌞 GO CASEY RAND LOL “When I’ll Know AI Can Replace Me” in McSweeney’s.
🌞 A good pal of mine was visiting a couple weekends ago and how we got hooked back on “Word Up” is beyond me. Say what you will about Gen X but these were the videos that raised us and you can’t tell us shit.
🌞 “LA’s ‘Most Tasteful’ Burglar: The Case of a Mid-Century Modern Furniture Thief” is a mini-doc absolutely vibing at the intersection of mid century design, bonkers brazen crime, and pricing insanity.
🌞 Your Friends & Neighbors is an outrageously chaotic, frequently intense, surprisingly melancholy, and genuinely quite funny show that might just be the perfect midlife show in 2026. How far would you go to survive? To keep your life? To keep up appearances? are the questions it keeps asking. I blew through two seasons in two weeks and I cannot wait for season 3.
🌞 As if I couldn’t love my pals more who decided to open a pizza place in Warren, Maine (and it is so, so, so good y’all), then Megs started writing what is one of the freshest/funniest/most endearing newsletters (Pizza & Other Things right here on Substack), and then they turned a hidden room above their pizza place into a lil bookstore? I mean, stahhhhp. This made me el-oh-el several times: “The Day We Opened Upstairs Books”
When you live in a place with long winters, summers feel like they go by in a blink. Raising kids, especially teenagers, is a fraught enterprise during these fleeting free-for-all months. Practically anything a kid wants to do outside either on their own or with friends you say yes to, even when you spend perhaps a lot of that time worrying. I know I did. I loved every time my kids took off on adventures and was equally relieved when they arrived back home.
The things that make Vermont summers so special are also the things that are capable of randomly, cruelly taking young lives. Swimming holes, riding bikes, being in the world. At least one middle school, high school, or college aged kid dies every summer, doing the things that they’re supposed to be doing, the things that we actually want them to do. These are terrible accidents, random and tragic. It could be your kid or mine—easily—but it wasn’t.
Shiloh Skalka was only 16 when she was hit and killed while riding an e-bike in Burlington a month ago. I didn’t know her or her family, but Burlington is a small place. I’m only one degree of separation from them. I’ve thought of her, and all the things that would’ve been ahead of her this coming school year as a junior, and all the things that her parents had to look forward to, too. I’ve thought of the friends she’s left behind, her twin brother who has his whole life ahead of him without her. I’ve thought about her parents almost every day. It’s still unfathomable to me how a young, bright, beautiful person can be here one minute then gone the next. It’s unfathomable to me how anyone survives grief like this. It has made me feel sick, actually. It’s fucking unfair. It’s just so fucking unfair.
We’re all awash in GoFundMe’s because we’re living in broken times, but I’m sharing this one in memory of Shiloh in case you are so inclined. All donations are being coordinated through a managed fund to directly support giving to local organizations and community programs aligned with Shiloh’s values, including creativity, community, and compassion.
In these waning days of summer, these days that have always felt heavy to me with a type of seasonal grief, I hope you’ll find moments to think about everyone you love most and to make plans to see them. These are my new marching orders for the rest of this year and early next. Maybe they’ll be—should be—my marching orders forever.
You can find my books here.
You can find more writing here.
You can find my work for brands here.
You can find my podcast here.
You can find me wasting time on Instagram.

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