A newsletter about the newsletter (Ricky Weekly #17)

This is where I share 3 things every week with my friends and anyone else interested.

A picture from my life:

Went to the Coliseum to watch the A’s wild card game. I haven’t been following baseball for the last decade and during that time my Dodgers have become one of the best teams in baseball. That makes me sad because I used to tell people that baseball’s my favorite sport. Unfortunately, I never got to play baseball myself but I play a lot of basketball, so when life got busy and I had to make a choice of which sport to follow I ended up choosing basketball. Baseball is important to me for many reasons, one of which is that it’s the one thing my mom and I can bond over. She’s a huge baseball fan. I didn’t watch a lot of cartoons growing up, but I watched a lot of baseball so I can talk to her about it.

Go Dodgers!

Thing on my mind:

A few of you have asked me to write about this newsletter experiment, so here it is. It’s a little long so brace yourself.

This newsletter started because my friend Yoshio and I were talking about how much we both want to be better about connecting with our friends. He mentioned Tim Ferriss’ 5-Bullet Fridays and I thought “Five bullets every week, that sounds do-able!” So I decided to write a personal newsletter following a simple format that I can see myself sticking to indefinitely. 17 issues later and roughly 5 months later, I’m still sending these and I love it.

Open rates. In the beginning when the list was about 25 people, the open rate was >85% for the first few issues. Now the list is at 140 people and we’ve settled at around 65%. Not bad.

Click rates. Sometimes 30% of the openers would click at least one link. Sometimes <10%. Really depends on the content. I think people only like to click on articles, not podcasts or videos.

Openers. I can see how many times you open the email. I find that if you’re working on a response to me, you tend to open and re-open the email a lot.

Responses. I get at least 1 or 2 every week. Out of 16 issues I’ve had 2-3 that really resonated and those would get 5 or 6 responses. The responses are great and it’s one of the best things that’s happened with this experiment.

Who seems more engaged? My strongest ties definitely pay attention and once in a while reply or reference it when we hang out in-person, to my surprise. The people who seem to get the most out of my newsletters though are weaker ties that I don’t get to interact with as much for whatever reason (family, location, career, etc). I’m surprised that a few people I only recently met have subscribed to my newsletter because I put it in my email signature. They seem to enjoy it and when they respond to me it feels like our relationship is developing faster. I’ve inspired at least two people to write newsletters. That’s so cool!

How do I write it?

I track my time and it takes me anywhere between 30 minutes to 2 hours to write an issue. How long it takes depend on 1) if I already jotted down my thoughts during the week so I can just take the notes on Sunday and churn it out and 2) how complex is the thought I’m expressing. Pictures and link recommendations take no time. If I don’t feel inspired to write the newsletter on Sunday, I don’t stress about it. I’ve skipped a week a few times and I’ve sent the newsletter late on Monday or Tuesday a few times too. I’ve learned from your feedback that this exercise is first and foremost for me, and that you only want to read if I feel inspired enough to share, so forcing it serves no one.

Other thoughts

I find that most of our social media sharing today has to do with milestones or manicured thoughts. Otherwise it’s photos which mostly express where we are and what we’re doing. What’s missing for me is what is inside people’s heads. What are you thinking about? The newsletter is an attempt to get what’s in my head out there, and it’s been great because when people respond they are responding directly to a thought in my head, which cuts through the noise and I feel like we are connecting on a very meaningful level.

Having a weekly cadence is good practice to just force me to practice publishing my thoughts. It also has the added bonus of creating availability bias to my benefit because I show up in your inbox every week, you think about me more and engage with me more.

In the beginning I started with 25 people who I knew wouldn’t mind me just subscribing them to a newsletter, then I announced it on my Facebook and added it to my email signature. Before I announced it on Facebook I wondered if what I write would change with a bigger audience, but I still did it because I’m more comfortable than the average person to appear vulnerable so I might as well lean into that. I can also just stop if I don’t feel like writing anymore. Over the last 17 issues there were two instances where I had to censor myself or obscure the facts a bit because I knew I didn’t want certain subscribers to know some things, but those were pretty extreme examples. In general, I’m sharing way more than I would anywhere else online, and that’s a good feeling.

I think a lot of why I like it has also to do with email as the medium. “The medium is the message,” and email creates an expectation of something more thoughtful and personal. There’s no way to give me feedback other than replying, which leads to a 1-1 conversation. Technically my newsletter is public and anyone can subscribe, but it still feels semi-private because it’s not that easy to find and it gets delivered straight to your inbox. I think privacy by relative obscurity is important in getting me more comfortable at sharing.

Again I can’t recommend Yancey Strickland’s The Dark Forest Theory of the Internet enough, here’s a quote from him that really resonates:

In "real life" I'm a reasonably self-confident, 40-year-old human. If we sat next to each other on a plane we'd have a good-to-memorable conversation.

But on the Internet, I feel like a teenager struggling to find their identity. I'm all awkward exclamation points and weird over-explanations. I'm often too self-conscious to be interesting or real.

When I used the Internet as an actual adolescent in the 1990s and as a young adult in the 2000s, this wasn't the case. I blogged every day. Message boards were how I learned to test theories and debate ideas.

These communities were small enough that people knew each other but big enough that there was a diversity of opinion and conversation.

You could vehemently disagree with someone about politics in one thread while agreeing just as passionately with that same person in a debate about movie sequels in another.

I had no problem being myself online then. But now it feels different.

A lot of this difference is on me. I'm older. I have more at stake. But it's not just me that changed. The Internet did too. The Internet went from a venue for low stakes experimentation to the place with some of the highest stakes of all.

What resonates is the ability to be vulnerable. A Internet that is big enough yet safe enough. The idea of being able to test theories and having lower stakes. That leads me to the piece of content I am recommending to you this week…

Piece of content I recommend:

How to Design Social Systems (Without Causing Depression and War) by Joe Edelman

I like it because he calls out the need for “practice spaces” that support our need to work out our feelings, identities, thoughts, etc. Here’s a quote from the article.

So, imagine a teenager. She is sorting out how she wants to be, socially. She is exploring ideas about how people ought to act (intelligent, feminine, polite, etc) and questioning them. In different situations, she tries out different ways of being intelligent, feminine, or polite, and sees what happens. She may at first imagine she wants to be infinitely feminine or infinitely polite, but in the context of real choices, these values no longer seem right. She reflects on who she wants to be, and how she wants to live.

We all make small choices, everyday, using the same process the teenager used for these big choices. When we approach a conversation or meeting, for instance, we may need to decide how to balance honesty and tact. Even with these small choices, we need to experiment and reflect.

This newsletter is a “practice space” for me - and I’d like to create more spaces like it. I don’t think writing a personal newsletter is ever going to be a mainstream activity, but I believe we can all use something like it.

One answer from last week, one question for this week:

In my last newsletter and I said:

There seems to be no good rational reasons to startup. But there are millions of valid reasons why founders continue to choose to be founders.

I thought Gregory Rose’s response was interesting:

Something I've been thinking lately: This is only irrational at the individual level, but completely rational at the population level (as Taleb argues in Antifragile). Society's benefitted immensely from every single founder who made this irrational decision and was successful.

A message I keep personally thinking about, and that I'm increasingly seeing in a number of successful or happy people is this: "It's not about you. It was never about you."

I'm increasingly convinced that many things we think are irrational do make sense in some way we miss either on a broader timeline or broader group of people.  e.g. The prisoner's dilemma was the wrong experiment - it should've been the repeated prisoners dilemma. Or, irrational individual behavior might benefit the group, and therefore still be preferred by evolution. I'm sure there are still  exceptions, but I wonder how many there really are.

My question for you this week is: Where do you practice vulnerability? How do you experiment and work out messy feelings and unclear thoughts?

As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My latest essay is called The arc of social