What makes a good email newsletter?

or 5 reasons why I'm doing yet another newsletter

Josh Spilker

Jan 10, 2023

Impersonal algorithms.

Misinformation.

Fake news.

But also:

Timeliness

Personal.

Direct.

The above list is why we’ve seen a rise in email newsletters over the past few years.

You’ve probably seen them, too. The trend started with a morning roundups of the news, when traditional publishers weren’t doing their jobs.

That includes TheSkimm and Morning Brew.

But then others couldn’t find smart analysis beyond without the traditional advertising model, so they jumped in with paid options.

That includes bigger players like Stratechery and many of the newsletters on this very platform, Substack.

Many journalists have defected to their own Substacks where they feel they can do their best, most individual work.

There are now more than a million people that subscribe to a Substack, fueled by the rise of journalists who view it as alternative media, a lifeboat or both.

What’s the advantage of an email newsletter?

It’s frequent
It’s timely
It’s personal (The email inbox)
It’s more direct than social media
You can go in-depth or keep it simple
People (like yourself) can opt in or opt out
It has simple distribution, not based on algorithms

So yeah, why another newsletter? And by me?

I’m no one special, but I do like to write. I’ll get into some details below:

1. Online writing is changing

A lot of you may know that I do SEO (search engine optimization) and content for a living.

I’ve become somewhat decent at getting things to rank on Google. I can’t do it for everyone or every product, but I’ve had some success.

That said, there are new technologies called “GPT-3” and “ChatGPT” and “AI”.

The quotes are a little ironic, because they are real things, but they’re also evolving things.

Apps and programs are being built on top of them. They also spew out words fast.

They are the literal firehose that writers always talk about.

This technology has implications specifically for what I do in marketing. I’m not worried about me finding work and honestly, the best SEO people aren’t worried either. There are still limitations to what it can do. That said, flexing other muscles is not a bad idea. In that regard, this is an experiment of sorts — especially for the actual site CreateMakeWrite.com where I’m trying a few SEO experiments. This newsletter will one day be more integrated into it.

Blogs used to be more like this, with interconnected blog rings and lively comment boards. Substack and newsletters have captured that energy. Conversations can be more insightful and longer.

If the medium is the message as Marshall McLuhan once said, this format is much better and slightly closed than social media.

2. Decades, not days

Love this from Andrew Chen, who’s a Silicon Valley venture capitalist who has chronicled his time there for a while via blogging:

Think of your writing on the same timescale as your career. Write on a multi-decade timeframe.

Over the past few weeks, I’ve met up with friends who live in town and have known me for a decade plus. What an incredible gift.

It made me think that I’ve never really considered my art or my writing in terms of decades. At least not recently.

Instead, my professional writing has been more about the daily traffic and comparing that to the daily traffic the week before. And then the month before. My personal writing has been about creating and then forgetting.

Creatively, I didn’t see any real engagement or returns from submitting to literary journals or even querying agents. I published 2 books for myself, with no expectation about what they would do. (Set the right expectations for your writing!)

For the most part, I’ve only thought of my wife, my family, my friends, and my Christian spirituality in terms of decades-long commitments.

I’ve never had one job for 10 years.

I can’t even believe I’ve lived continuously in the same city for 12 years.

But what if I considered my writing in that terms?

In the past, I’ve considered books as a potential avenue for that, and books can be known and remembered for years. But how can they be developed? And the process isn’t always linear.

A newsletter like this can have that space to develop ideas on a regular basis, but also on a potentially decades-long effort. I had a newsletter about fiction and writing and other weird stuff a few years ago. I looked it up recently and noticed I hadn’t sent anything in 7 years.

The cutoff date was right before the birth of my 2nd child. (Think there’s a connection???)

Will this newsletter continue for decades? This is officially issue 2, though I’ve been writing in other places semi-consistently for a while.

It’s way too early to tell if a decade is feasible. But what if it was?

There will be some ups and downs in creating this, I’ve already experienced them, but what a record for those that are able to achieve it.

3. A weekly ritual

In college, we did a beach trip a few times with a group of friends.

We stopped at the same pancake place two years in a row on the way.

The next year, my friend Amy referred to stopping there as a “tradition.”

I disagreed. Two times doesn’t make something a tradition does it?

Amy thought yes, I thought no, and a fun fight among familiar friends began.

(((I think Amy may have even subscribed to this? (Hi Amy!)))

But after that “It’s a Tradition!” became a funny callback line to anything we talked about doing more than once.

Now in middle age (it’s true) I’ve thought more about the rituals my life is based around.

Some hold more meaning than others — (church in some ways is more sacred than Friday pizza night with my kids; in some ways, it’s not) — but they both help us create a rhythm.

Rituals give us bearing and grounding. But starting a new one is hard. There are weak spots.

That’s why consistency matters to make a ritual.

And if it’s a ritual — it lasts. For quite a while.

When I think about my work, my writing, this is a regular ritual that I want to invest in.

I’ll make mistakes, I may even miss something. But if I have a decade-mindset rather than a today-mindset, this is something I want to invest in.

I’ve had stops and starts before. But this gives me a regular weekly missive that I think will bring clarity to my other work — whether that’s work I get paid for or writing more books.

4. Processing the conversation

A lot of information passes by me.

I read a ton for work, I subscribe to several news sites, even a few print magazines, and I always have a book that I’m reading.

I read a lot of trend pieces—not really breaking news. Like about technology or an interesting true crime story. I find myself wanting to talk about these things and thankfully I have a few friends who do the same.

This newsletter is a small attempt to expand that conversation slightly, to share something a little differently, and then “process” it if necessary. (No one thinks anymore, everyone processes).

5. To validate, or not to validate, that is the question

A popular concept in tech and in startups is to “validate your idea.”

The thinking is that you need to gauge interest and need in a product before you build it.

You build an MVP (minimum viable product) and get feedback and make iterations. There’s a lot more to it than that, but you get the idea.

But there can become a point of diminishing returns, especially with new ideas or technology. Users don’t always know what’s good for them or what they want.

Often, like lots of things in life, it’s better to see what they do instead of what they say.

Writers don’t always know what we want.

The same can happen with…writers. We may think in algorithms only — either the SEO one (like myself!) or the social one or another reward system that is sometimes hard to break out. Writing is thinking and a newsletter is part of that process.

Readers don’t always know what they want.

The same can happen with…readers.

Corey Doctorow, an internet writing veteran, has a good essay about how readers used to put up with the musings of a writer on y topic because they mostly enjoyed the writer talking about x.

They would either ignore what they didn’t and pick out the parts they did.

That has changed a lot because algorithms have given us more and more niche interests.

But what if we went back, Back To the Future style?

As Doctorow said:

Once upon a time, it seemed like our web would be one where we explicitly assembled our reading based on our interests, rather than letting the algorithms do it for us.

This newsletter is my meager attempt to push back against the algorithms. I’ve had some success with writing for algorithms. There is value in it. The algos aren’t always wrong.

I’ve also gone the other way. As mentioned, I used to write a lot more fiction. And it was weird, too. One was about taco trucks. Another was self-referential metafiction.

What was the audience? There wasn’t one. Did I create demand for it? Not, really.

There’s a fine line there for the audience between pleasant surprises and providing what they want or need.

This newsletter is my attempt at the middle, with an overlap in the Venn diagram.

For this space, the main topics will be online writing, creativity, and productivity with some wiggle room.

Thank you for being here.

Share Create Make Write by Josh Spilker

Last things:

I’m in Florida for the month of January, which is a huge gift. Seeing family, being in the sunshine is something I love. I needed to get out of the harsh winter of Nashville, TN lol.

Last week:

Planners: Should you use one in 2023?

On deck:

Not sure of the order, but these are topics I’m exploring.

Writing as thinking
Life (not) as a narrative?
Why read fiction
Twitter Threadbois: A Primer

Find me on Twitter or LinkedIn or Medium.

Keep going,

-Josh Spilker