Understandably celebrated a birthday this week. We’re 3 years old!

We’ve done some good work that I’m very proud of, and I’m grateful to so many people. We’ve also had a chance to shine a light on some fantastic writers and stories.

Here’s what it looks like by the numbers:

• We’ve grown to more than 162,000 total subscribers, along with about a 32% daily average open rate.

• That works out to roughly 50,000 actual real, live human readers on any given day.

• Daily readership is up more than 50% since the start of 2022. Pretty cool!

As long as I’m bragging, I realized recently that Understandably is now the number-1 ranked newsletter on Substack in the "news" category, ranked by total subscribers and engagement.

(Is “news” the most appropriate category? Good question. Perhaps given the “7 other things” section—and the fact that we publish daily—maybe it’s the closest.)

Anyway, three years is a long time. As the milestone approached, and especially after my "low power mode" experiment earlier this year, I’ve wanted to write something about future plans and challenges.

Each time I’ve dug into it, however, it’s turned into a 10,000-word novella. So, maybe I should start more simply, just sharing some of the questions I find myself thinking through as we reach this anniversary.

Maybe people want to comment? Maybe people have ideas? Maybe you’re not supposed to share things like this? (Too late; I already wrote it.)

Maybe just articulating it all and putting it out into the wild will be of benefit.

I’ve raised some of these questions before; others not publicly. But in no particular order, here are 17 questions I’m grappling with.

17 questions

1. Understandably is a daily email. I don’t plan to stop publishing daily. But, what if we organized it more like 5 weekly, staggered sections—making each day more focused and predictable? For example: “money topics on Monday,” “tech topics on Tuesday,” “wellness on Wednesday,” etc? If so, what happens to the “7 other things” section? Include it each day? Send it separately? Build it into something bigger?

2. Related: Would it make sense to have both “daily” and “weekly” options? It’s a bummer to hear from some readers, as I occasionally do, who say they love the newsletter—but they’re unsubscribing because there is just too much of it.

3. We rely overwhelmingly on member subscriptions, and I’m very grateful for those who have become premium subscribers. But, should I offer other ways to support? Tips? One-off contributions? Merchandise? I doubt this newsletter would ever make “retire on a beach” money, but more revenue would mean more chances to reinvest, pay more guest writers, and spend more time working on it strategically.

4. What additional benefits should I offer paid subscribers? Ebooks? Special events? Sit in on my interviews with interesting people? Should I just put some content behind a paywall? Make the premium version ad-free? (I would like to do this last point, but it’s harder than it should be on Substack, for technical reasons.)

5. Speaking of Substack: I’m thankful for this platform, but is it the best one to continue to be on as we grow?

6. Should I do more videos? YouTube interviews? Roundtable discussions? Record a version of each newsletter as a podcast?

7. How can I better leverage the community of readers? It seems as if I can ask almost any question of this audience and find someone with experience and expertise.

8. Great, we're #1 in news. But are we news? Are we something else? It’s kind of a funny problem that three years into this, I still can’t describe the newsletter well in one sentence.

9. Ads. We need them. How can we do them better? It’s the entire business model of some other successful and respected newsletters.

10. Guest posts. I wish I were better organized here. How can I improve my rather haphazard way of finding fantastic writers who have things to share that readers will love? Also, writers shouldn’t write for free; how can I better handle editing, tracking, and paying them?

11. One idea people have raised is to bring in contributors for a few weeks at a time—almost like a residency—and work with some of them to build and launch their own publications: newsletters, podcasts, websites, etc. I suppose there should be a question attached to this, so: Would that work?

12. We include a big essay AND “7 other things” every day. Would the world come to a screeching halt if on some days we just did the 7 other things? Or maybe more than 7? I’ve done this a handful of times, but what if it were a more regular thing?

13. Are posts like this one too navel-gazey (aka “self-indulgently introspective”)?

14. At this point, I think I’ve made every mistake in starting and building a newsletter—but I’ve learned from them all and built something successful and growing. Should I teach a course on how to do it?

15. I take pride in the idea that we have an audience that’s all over the map politically, but that generally gets along. Is that as valuable a thing as I think it is sometimes? How can we leverage that better?

16. This question should be higher up, but: Is an email newsletter the best vehicle for this to begin with? It’s somewhat reliable and habit-forming, but are there other formats that would be better? I used to have a note over my desk that read, “Understandably is not a newsletter,” but it sort of is, just because that’s how I’ve kept it.

17. Kind of related: Do people read Understandably via email, or on the Web, or via the Substack app? Actually, let’s ask this last one via a poll.

This ran a bit longer than I’d planned for a Friday, but it felt good to ask all these questions. Thanks for your indulgence and your comments. And of course I have to add: If you’re not yet a premium subscriber, what better time than our 3rd birthday to become one?

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7 other things worth knowing today

• News broke last night about widespread layoffs at Twitter; the way employees are learning their fates seems rather heartless. Earlier in the day, as it happens, Stripe laid off 14 percent of its workforce; I wrote for Inc.com about how the email that CEO Patrick Collison sent to employees was worth reading—and now stands in stark contrast to the Twitter layoffs. (Engadget, Inc.com)

• The Bank of England has warned the U.K. is facing its longest recession since records began, as it raised interest rates by the most in 33 years. It warned the UK would face a "very challenging" two-year slump with unemployment nearly doubling by 2025. (BBC)

• A bunch of Fox News anchors say they won't pay Elon Musk $8 a month for a blue check on Twitter, calling the idea "embarrassing." (Mediaite)

• One of the nation’s biggest publishers has decided to stop printing Alabama’s three largest newspapers and make them digital-only, the latest in a long string of local paper closures across America. The print readership of all three papers was 260,000 a decade ago; now it's just 30,000. (WSJ)

• El Salvador’s government took its efforts against the country’s powerful street gangs to another level by sending inmates into cemeteries to destroy the tombs of gang members at a time of year when families typically visit their loved ones’ graves. (AP)

• Frontier Airlines has announced that beginning in Spring 2023, passengers will be able to purchase an unlimited flight pass. The pass will be known as Frontiers "GoWild" pass. No price has been listed for the pass, nor has any specific launch date. The airline hopes this unique offering will help fill many of its unfilled seats. (SimpleFlying)

• As clocks fall back this weekend, America's hyper-popular plan to make daylight saving time permanent has made no progress. (Quartz)

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Thanks for reading! Photo by Annie Spratt on Unsplash. See you in the comments.