Why I Email Five Jokes A Day

Some people do Sudoku or Wordle each morning — I do this.

Free image by Suzy Hazelwood

I’m getting married this month and taking a break from what’s recently become my morning ritual of emailing five jokes to subscribers. But I thought it’d be nice to explain why I primarily write jokes here now instead Twitter and Facebook, and what I’ve learned from doing so in the process.

Blame it on Elon! He’s basically the reason I launched a

Substack

newsletter in the first place. Elon Musk promised to purchase Twitter, then didn’t, and later in 2022 — actually did. That whirlwind of frightening change prompted me to take a look around and figure out how to best get away from the endless scroll and start writing in a more meaningful way online.

Twitter (now ‘X’) is rapidly devolving in ways that I don’t think many people realize.

In one of the jokes I emailed just last week, I poked fun at one of X’s latest policy updates:

• An upcoming privacy policy update shows that Elon Musk's ‘X’ wants to collect users' biometric data and education history. Which is concerning because ‘biometric data’ and ‘education history’ are the two things Musk asks for on date. Experts worry that the next update will “…somehow technically make all users his spouse.”

And, in a recent text interview with writer,

Mychal Denzel Smith

, I expressed my concern with how difficult it is to track changes of social media:

Mychal Denzel Smith Interview: DAY 1 (Tuesday 08-01-2023)

Tim:
(2:15PM) The constant evolution of social media services is something I think about a lot. I can’t even imagine what Facebook looked like when it started and even when I try to visualize present-day Facebook in my head it still feels so vague and blank. Remember when our avatars were squares instead of circles?

Mychal:
(2:16PM) Literally, no haha (2:16PM) Wait, when we’re they squares???

Tim:
(2:17PM) On Facebook, Twitter, everywhere… (2:17PM) Profile pictures were square (2:18PM) I don’t remember when they changed

Mychal:
(2:18PM) I truly can’t remember them being anything but round, it’s all a blur [Tim gives this an iPhone "HaHa"] 

Tim:
(2:18PM) But there’s something troubling about how intangible these platforms are. You can’t clock the changes the same way you can with the evolution of TV sets

Mychal:
(2:19PM) Facts, I remember the non-flat screen TVs vividly, but have no recollection of this square avatar business 

It’s also bothersome how much of our creative lives are dedicated to adapting to ever-changing algorithms. And that is something that plagues both individuals and corporations. I was once in a conference call between representatives of a media outlet and Facebook employees, where the outlet was desperately trying to ascertain how to best maneuver its ‘content’ around a new shift in the social media site’s priorities.

And beyond such nightmares looms a larger one… What happens when a space like Facebook or Twitter disappears, or becomes so radically different that it’s no longer worth engaging with? What happens to your fan base, and all of your work that was so tethered to an outdated system? That question is what led me here, writing jokes to a dedicated group of subscribers, with a self-imposed deadline of posting them at 11AM Eastern each weekday.

Here’s what I’ve learned:

The Pressure Feels Great!

The pressure of a daily deadline gives me an adrenaline rush each morning. There are pitfalls to my ‘post it by 11’ rule, yet I find the disappointment of emailing a joke with a glaring typo or wrong link, serves more as fuel for me to become a better writer.

I haven’t performed on stage with any consistency since the Covid pandemic began, but I find this to be the closest match the zen-like anxiety that takes over, moments before the host of a standup showcase says my name — something Patton Oswalt recently crystalized in this tweet:

https://twitter.com/pattonoswalt/status/1696754598252572884

Often, mere moments after pressing ‘send,’ I think of a better phrasing to a joke. But unlike Twitter, I can’t delete it. The email is out there in hundreds of inboxes. Scary, yes. But that’s what happens on stage anyway. You can’t take the words back. But there’s always another day to learn from your mistakes and do better.

I No Longer Rely On ‘Likes’

The dopamine hit of getting a bunch of ‘likes’ on a joke is a lot like eating a whole cloud of cotton candy. It feels great while you’re eating it, but you’re never truly satisfied by the time it’s gone, and you’re always left wanting more. Or maybe that’s just me, and this analogy is falling apart.

Forget the analogy! The fact is that sending five jokes in a row as one unit has a completely different value than posting one joke at a time. There’s a rhythm that can emerge and a sense of each joke building to the next — much like a late night monologue.

This long-form model of joke writing makes me care more about what my subscribers enjoy generally, rather than trying to wow them with my genius every hour or so the way I once did on Twitter.

Finally…

I Know So Much More About The News!

And that’s because, rather than simply reading headlines tailored for the algorithm on Twitter, I’m actually seeking out the news each day, going to various websites and READING what’s contained in the body of each article (for the most part)! It makes me feel less like Pinky, and more like THE BRAIN! Know what I mean? Like, finally, at long last — I am smarter than a 5th grader!!!

On social media, you aren’t just talking to your followers — you’re also projecting to the world. And that’s something that has done wonders for my career. However, the public eye can also feel like the firey peeper of Sauron, hindering your growth while also promising you power.

Some people do Sudoku or Wordle each morning — I do this.

And that’s the end of my long ramble for the day. Five Jokes will be back in October, and you can look forward to interviews and more posts like these in the days and weeks ahead.

-Tim