What I Learned From Writing A Newsletter for 2 Years

24 lessons on audience, writing, planning, marketing, and writing as a rabbi.

Read time: 10 minutes

I launched the With Torah and Love Newsletter (WTAL) with its first post on October 1st, 2020, yearning to express myself in a new way. I did not have the opportunity to give sermons with any regularity and I was struggling with wanting to share the Torah in my heart.

As we approach the two-year mark, I want to share some of the lessons I’ve learned.

They are not universal truths, perfect advice, or anything so grand. Rather, I wanted to take an opportunity to share the previously (until now) unarticulated ideas that have been floating in my mind with the hope that they might be helpful to anyone who wishes to explore this option.

Note on context: I think of the audience of WTAL to be similar to “congregants” but on the internet.

As much as I would love my colleagues to read my work, WTAL was not focused on them and my publishing strategy mirrored that. This newsletter, Jewish Work, does exist to serve you, the reader, my colleagues in this meaningful and powerful work.

The lessons learned are organized by category, but not importance:

• Audience

• Writing

• Planning

• Marketing

• Writing as a Rabbi

Audience

1. Write with someone specific in mind.

As in my congregational work, I eschewed the idea there was a thing as everyone. In my newsletter writing, I applied the same thinking. I’m writing to an audience that has specific needs, wants, and challenges.

I write with those in mind and try not to expand to subjects that don’t relate to them. (It is why I launched this newsletter.)

2. Writing regularly helps build a relationships with the audience.

When we become a part of people’s routines and experiences, we begin to connect with them in a new way. As clergy, this is something we regularly experience. As a newsletter writer, I can think to myself “this reader is gonna love this one” or “I bet I’m going to get an email from this person.”

The connection takes a long time to build, grounded in trust, but as we grow that relationship, we can write better and better pieces.

3. My audience wants short and dense.

I originally thought my audience would prefer deep dives into a concept or idea. However, via experimentation, I discovered my shorter, denser pieces have higher read rates and more likes (on the Substack platform).

As a result, I shifted my writing to better align with the audience’s needs. I found my writing improved and my rates increased across the board. I am always testing my assumptions and try not to get too bound in one way of writing.

Understanding our audiences and what they want or need can be powerful.

Writing

4. Create “templates” to help the writing.

Creating a template does not mean we are copying our work from week to week, rather it is developing different scaffolding to hold our ideas. When I create a template that works well, I find I can spend my energy on creative thinking instead of organizing. These are known as creative constraints.

For WTAL, it looks loosely like this:

• Hook/Story

• Verse/Text

• Explanation

• Lessons

I can expand it or adjust it as the subject allows, but this is the starting place in mind. You can find examples here, here, and here.

5. Kill Your Darlings

One of the best and longest-standing pieces of advice to writers I’ve seen quoted a zillion times is: Kill your darlings. Attributed to lots of writers, it has a specific meaning:

If removing an element does not negatively impact the piece or does not substantially add, you should remove it.

It means sometimes you remove elements you love. A great quote, subsection, metaphor, or idea. If it doesn’t help the reader, it doesn’t need to be there.

6. The hook helps.

Reading habits have changed and readers don’t have the same level of patience. Writing a good hook can help people connect with the piece and stick with the writing. That first few sentences can make or break someone’s willingness to read.

7. Writing is a thinking process.

What I’ve discovered is in the process of writing, outlining, and brainstorming, my thinking has improved. I used to believe: I should know exactly what I want to write before I begin. Sometimes, I come to the writing with a few core ideas and it can help get me started.

But more and more, I’m realizing the writing and thinking process is overlapping. My writing often begins in one place and ends in another. Recognizing you don’t necessarily need to know the outcome when you start has given me more patience to let the ideas flow.

8. Eliminate the unnecessary “that.”

I use the word “that” so many times within sentences. After I finish writing, I search for “that” and remove as many of them as possible. My writing sounds better and is easier to read. Hard to go wrong.

9. Readability matters.

Using headings, icons, italicization, and other such formatting tools make the content easier to read. Readers have little patience these days and are primarily skimming our content for the elements that interest them.

Formatting allows us to make it easy for our audience to find what they want and need.

10. Improving my writing every week is more important than perfection.

I work diligently to write my best every single week. Some week’s are better than others. Recently, I wrote a piece and did some math and was off by an entire magnitude. Not my greatest moment.

I was so embarrassed and quickly fixed it on the web version, but had no way to fix it for the folks who receive my newsletter by email. Having everything be perfect is an unattainable goal and I reminded myself I would just do better the next week.

Growing and improving one’s writing and the process is a long-term goal and we should not expect to experience perfection. Holding back from starting will mean the improvement process is delayed, not that our writing will be better.

11. Trust the process, just keep writing.

The more I write, the easier coming up with ideas becomes, my writing improves, and I feel more confident. Sometimes, all you can do is trust the process, and keep at it.

Planning

12. Once a week is enough.

Every once in a while, I imagine writing and publishing daily on the newsletter. Don’t worry, I won’t be doing that.

But in truth, more than once a week is too much for most audiences. There’s a good reason why weekly is such a solid structure for television, Youtube, podcasts, and newsletters. It is enough to give people time to absorb the material.

There are certainly exceptions to this, depending on your audience, subject matter, newsletter style, or if something is particularly timely, but for me, I realized once a week is enough.

13. Don’t make promises I can’t keep.

Occasionally, I’ll get excited and want to publish a whole series or niche down on something really specific for a while, but most of the time when I try and commit to that, it is too challenging to maintain.

Instead, just continuing to write the best I can, exploring and expanding my writing, and focusing on good, solid, helpful content every week is better than some grand promise.

14. Write farther in advance.

For WTAL, I still have a tendency to write on Friday mornings, but my writing is almost always better if I write farther in advance. I’m not good at this particular lesson, but every week I tell myself this and work to improve.

Writing farther in advance allows for craziness in one’s schedule or to utilize one’s editing prowess in a more effective way (by not writing and editing simultaneously).

15. I’m going to miss publishing occasionally.

This is a tough lesson for me because I feel a bit of shame when I miss a week. At the same time, I try and remind myself I’m just a human being and that I’ll do better next time.

Staying in the rhythm is easier than trying to get back on it.

16. Creative constraints are good until they aren’t.

When I first started, I had a sense I would write only about the weekly Torah portion, which I still mostly do. But sometimes, I’m not inspired by it or I want to talk about something else instead. I used to feel really frustrated about that until I decided it is more important to share something meaningful and real than force myself into this structure.

Constraints can be really helpful in keeping you on track, but can also limit you in negative ways. Giving myself permission to talk about something other than the Torah portion, but still Torah, in the broad sense, was a gift.

17. Collect Ideas

Collecting ideas throughout the weeks and months you can draw on when you’re feeling uninspired means you’ll never start with a blank slate. Building a system to collect ideas and sort them as needed made a difference in my process.

18. Write and edit separately.

The farther apart my writing and editing are, the better the result. If I can afford 15 minutes, if it is late on a Friday, I’ll do it. If I can afford a few days, even better.

Marketing

19. The writing is more important than the marketing.

Don’t get me wrong, it feels good to see the numbers go up on social media. However, quality writing with something significant to say is so much more important. I don’t always get the balance right, but this is what I’m striving for.

20. People get this in their email, not just via social media.

Not every way we encounter information is the same and there is value in respecting the differences between them. Newsletters are email based, even if they can be shared elsewhere. This means someone has shared access to their inbox with us, there is a level of intimacy there.

It is important to understand that intimacy and treat it with the respect it deserves.

21. People will unsubscribe.

It is always tough to receive notice someone has unsubscribed from your newsletter, but it happens to us all. We can be grateful they took the time to read whatever they did read, supported our writing at all, or took what they needed and are ready to move on.

Rabbinic Writing

I have a lot more to say about rabbinic writing in general, but a few takeaways here regarding newsletters.

22. A newsletter is not the same thing as a sermon.

In addition to the audience, context, and style, recognizing that a sermon and a newsletter post are different is important. The core ideas of a sermon, the examples you use, and parts of the text of a sermon can (and should) inform or overlap with our newsletters, but we should recognize the difference between experiencing a sermon and a newsletter.

The ability to quote a text, use formatting, links to videos and other content, and the context of reading it on one’s computer or phone should invite us to think differently about how we present this writing.

Yes, it means it can be extra work than just copying and pasting.

23. Learning to write on the internet is valuable.

Spending more time writing on the internet over the past decade, and a newsletter over the last two years, has taught me how important this skill is. We can and should see internet writing and copywriting as part of our professional skill set.

I wish this was something I learned as part of my training, but grateful to have spent the time on it since.

24. Connect with other writers.

Writing can be a lonely endeavor. Developing relationships with other writers who are friends and colleagues can be incredibly rewarding. I have learned a lot from other newsletter writers about their approaches, inspirations, and systems.