How Much Chutzpah Does it Take to Launch a Second Substack?

It's Too Late For Questions

I’m here to announce the launch of a second Substack. Am I out of my mind, planning to produce content in two Substack spaces?

Well, it’s Too Late for Questions. I’ve already invested in the logo:

BUT WHY?

1. While I LOVE writing The Holy Chutzpah, there are mornings I want to write about something unrelated to Judaism. Unrelated to Israel. The problem: I’m a purist when it comes to theming. I once spotted an Easter egg dangling off a Christmas tree. I shuddered with revulsion. In fact, even mentioning a Christmas tree and an Easter egg on this Jewish-themed newsletter feels like a thematic stretch, but at least there’s the Venn diagram overlap of religion.

2. I don’t want subscribers to receive content they didn’t sign up for. If I started posting content totally unrelated to anything Jewish, I’d be sending The Holy Chutzpah subscribers stuff they didn’t agree to. That seems like a fast one, and while I have chutzpah, I’m trying to exercise the good kind. Not the unholy sort.

3. I love the community here. I love the exchange of ideas. I even had to cancel my Goodreads book goal for 2024 because I spent so much time reading on this site. Obviously, I’m still reading books too, but between all the essays I consume and all the newsletters here, my book count was way down.

4. Substack is booming!

5. In the writing community, it seems to be an ever present conversation: Where should writers aim to build their platform? Here on Substack? In lit mags? Or through the mainstream media outlets? I don’t think it’s an either/or question.

   I’ve got a couple of flash memoir pieces slotted for publication in lit mags this spring, and I plan to continue submitting in the future.

   As for media outlets, these are tougher for me as much of their content depends on the news cycle. While some outlets still publish evergreen essays (I published such an essay with HuffPost, for instance), most of the freelance landscape requires a timely lede. I’m not that timely.

   In fact, I am the very opposite of timely. That’s why my new Substack is entitled “Too Late for Questions?” I don’t think it’s ever too late; unfortunately, the mainstream media does.

I created the above image while playing around with an AI generator. I think it captures how I feel about my writing. About the ever-increasing velocity of time.

Can you see how this is an image meant for a writer of memoir and personal essay? I mean, I am interested in perspective that depends upon memory. I want to time travel.

I’m not saying I’ll never pitch a news outlet ever again. Time has already proven that I’m not a good predictor of my own behavior. Less than a year ago, I swore I’d never start a Substack, and now, I’m going to be writing two of them.

As for the above image, my dear friend, Olga, found it kind of terrifying. So, I also generated one that’s less likely to get classified under the horror genre. Check this out:

I am no longer this svelte, so it feels a little deceitful, but at least it still fits my new theme: Too Late for Questions? Middle-Aged Woes & Wonders. And did you notice the graying hair?

If you’d like to subscribe to my new stack, I’d love to have you over there. It’s free. I’ll be writing about all sorts of things from my very middle-aged point of view. I am fifty now. I think middle-age officially expires around 65? So, I’ve got 1.5 decades before I need to launch The Elder Years. G-d willing!

Meanwhile, I’ll continue posting my Jewish themed writing here. I like that The Holy Chutzpah will always be older. This feels appropriate. Judaism is ancient! Plus, while my newer stack grapples with my middle-aged perspective, it will remain forever younger than this one. Ha!

Please join me, again!

Sign up HERE!