The Accidental Power of Random Whimsy

Hi!
I’m coming up on Now I Know’s 15 year anniversary, and I’m still learning about what makes the newsletter work. A few weeks ago, I sat down with Dan Oshinsky, the founder of an email newsletter consultancy called Inbox Collective — he was kind enough to bounce ideas off him. We started talking about the things I wish I could improve upon if I had the resources to invest more into Now I Know, and many of them he agreed with — a better ad experience for all of you, cleaner archives, maybe bring on a writer or two, build an affinity program for the community, maybe some sort of podcast or deeper web experience, build a web-based mini-game… I have a lot of very aspirational ideals! But there was one thing he balked at, and it surprised me: I said, “I really wish I had an editoral calendar.”
His reaction was enough where I felt compelled to explain. Most newsletters — and really, everything else — share stories and content that are tied to the world around us. Christmas content starts in November (or maybe even late October). If something’s happening in the news, most writers try to use that as a hook to garner their readers’ attention. But I don’t do that, and it wasn’t for lack of wanting to — I just don’t have the time. I write three new Now I Know stories each week, share a rerun, and write this Friday letter to all of you. That’s a lot, especially as this is my hobby (I have a family and a job that both have to come first!), and it doesn’t leave me any time to for editorial planning. I often run stories about Halloween in March, historic events nowhere near theiir anniversary dates, and the like. And I told the other Dan, I wish I had that time to sync Now I Know up with reality.
He was surprised because he thought I was purposefully keeping Now I Know out of sync with the world. From his view, Now I Know provides something few others do: like Forrest Gump’s proverbial box of chocolates, you never know what you’re going to get. Now I Know, he observed, is quirky, random fun designed to tap into your curiosity to bring a little bit of joy into your days. The randomness is a feature — I shouldn’t “fix” it.
And you know what? He’s right. (And not just because he’s named Dan.)
I wish I had more time and resources to focus on Now I Know, but sometimes, less is more — and in this case, not having an editorial calendar is probably a good thing.
But that said: I do wish I had more resources to make Now I Know better — an ed cal just won’t be one of those ways! Another thing the other Dan suggest I do is be more transparent and explicit about how important reader support is to Now I Know. I told him I do that annually, typically in October (here’s last year’s) and he said I really need to do it four times a year. He is, again, probably right. (He also had some cool ideas for how I could expand this into a “Friends of Now I Know” program, which I’m still noodling over — more to come there.)
If you already support Now I Know, thanks a ton! I really appreciate it more than you know. If not, that’s OK, too! But I’d be remiss if I didn’t ask anyway. Reader support is easily the biggest funder of Now I Know — it’s not particularly close.
- To become a monthly supporter via the newsletter’s Support page, click here. If you do, you’ll get an ad-free version going forward!
- To become a one-time supporter via PayPal, click here.
- To become a one-time supporter via Venmo, click here — I’m @DanDotLewis
Your support helps me not only pay the bills associated with the newsletter, but also the ones associated with life. And those are important, especially now that my kids are in or soon to enter college. I won’t belabor the point — you all know how it is already. But I will do some math. I share about 200 stories a year, give or take. A one-time, $20 donation is 10 cents a story. A recurring $5 monthly donation is about 25 cents a story, including these Friday Weekenders.
I hope you’ll consider supporting the newsletter. If not, that’s all good too! Not everyone is in a position to do so or wants to, I get that. I’m glad you’re reading, regardless. 🙂
Thanks!
The Now I Know Week In Review
Monday: Ben Franklin’s One Simple Trick to Save Sailors from Drowning: Oil and water don’t mix, which can be a good thing if you’re on a boat.
Tuesday: The Fishing Trip with a Big Catch: A true crime story, but the crime isn’t one you think.
Wednesday: Gorilla Goggles: This was a re-run from my archives and the bonus item features the first video ever uploaded to YouTube. On the theme of “I don’t have an editorial calendar” from above, a lot of you — dozens — wrote in to ask if I intentionally chose this re-run because of the anniversary.
Nope, I didn’t.
In fact, I had no idea that Wednesday was also the 20th anniversary of its upload. Later in the day, I coincidentally found this article in the New York Times celebrating YouTube’s 20th and was amazed at my luck (and my miss).
Thursday: The Radio Stunt That Ended in a Death Sentence: This story is bonkers — how did he think he was going to get away with it? And how did he almost get away with it anyway?
Long Reads and Other Things
Here are a few things you may want to check out over the weekend:
1) “An Algorithm Deemed This Nearly Blind 70-Year-Old Prisoner a “Moderate Risk.” Now He’s No Longer Eligible for Parole.” (ProPublica, April 2025). I think the headline is as good of a hook as I could come up with.
2) “Hunting the Wild Mushrooms of New York City” (New York Times/gift link, 8 minutes, April 2025). You don’t normally think of wild mushrooms when considering all the things there are to do in America’s most populous city. But if you want to see a great diversity of fungi, it may be the place to go, apparently.
3) ”Scamming Pizza Hut Was My Family Tradition” (Food & Wine, 7 minutes, April 2025). This isn’t a very deep (that’s not a pun) story, but it’s fun. I was hoping that there’d be an investigation or caper attached, but no — the loophole is most of the story. Still worth the read!
Have a great weekend!
Dan