How, When, and Where to Engage With Your Newsletter Community

These stories are presented by Optimism, an email-first media company that publishes History Facts, Nice News, Word Smarts, and 15 other brands. They believe in the importance of bringing positive and informative content to the inbox. Through Curated By Optimism, they’re working with like-minded media companies to drive traffic to publications like yours. Interested in learning more? Get in touch here.

Prefer to listen to this story?

Engaging with readers can be one of the most rewarding, but also one of the most exhausting, parts of creating a newsletter. 

Other newsletter writers’ devotion to reader interaction has often intimidated me. The pithy additions below reader comments! The regular scroll of replies in a conversation! The inboxes stuffed with thoughtful emails that necessitate thoughtful replies! 

Often, this is part of the fun — witty, helpful, and complimentary feedback, the exchange of ideas, answering thoughtful questions. But this exchange can also include complicated factors, like when someone needs help a writer isn’t qualified to give, when debate gets out of hand, or when it simply becomes time-consuming.

But if engagement takes so much time and can cause complications, then why do it in the first place? There are a few reasons:

• Engagement helps you build loyalty with readers — The more you engage with readers, the more they feel connected to you and your newsletter. When a reader sees your newsletter in their inbox, that loyalty may lead to more opens, clicks — and maybe even revenue.
• It can help you foster a community around your newsletter — This community could be built in a comments section, via live events, or through a digital community hosted through a platform like Discord. In some cases, readers will pay for access to this community, which might allow you to build a new revenue stream for your newsletter.
• Replying might lead to new story ideas — Lyz Lenz, creator of the newsletter Men Yell at Me, said that engaging with her readers often helps her better understand what topics to write about in her newsletter. “It helps me understand my audience and what they like,” she told Inbox Collective, “so when I go to write my newsletters, I’m having the kinds of dialogues that make them excited and interested.” Some newsletters even use replies to crowdsource content that might get turned into a new newsletter edition.
• These replies can help with deliverability — Getting readers to reply to your newsletter sends a powerful signal to inboxes that your emails are valuable and should stay out of the spam folder.

So how do newsletter operators — especially indie writers who often are a one-person shop — approach reader engagement as they run their publication? I asked six newsletter publishers about their policies and practices around reader engagement. I found that there isn’t one way these writers handle engagement. Some reply to everything; others try to limit these conversations to certain spaces. Here’s what they told me about engaging with their readers.

The Small Bow: Not letting comments become “another job”

A.J. Daulerio doesn’t miss the days of responding to readers constantly.

A journalist for decades, including time as former Gawker editor-in-chief, he remembers that era  —- as do many reporters — as a pressurized time to respond to comments, many at the time who he considered “pests.” 

“I don’t want another job. [Comments] felt like another job,” he said. 

When he began The Small Bow in 2018, focused on long-term recovery and related subjects, Daulerio was thoughtful about what type of reader engagement he was seeking and facilitating. The Small Bow has always been a free newsletter, and it is a close-knit community where people often share deeply personal stories. The newsletter also hosts Zoom support meetings.

One issue for Daulerio is that people occasionally reach out for help he is not qualified to give. “I have no problem saying, ’I don’t know,’ and I think that is the truthful honest response,” he said. “A lot of it is with mothers emailing about their sons.” He has a social worker who sometimes edits things on the site that he can connect readers with.

To try adding more interaction, on Thanksgiving, he experimented with a live conversation for the first time, using Substack’s Chat tool, asking how everyone was doing and checking in from time to time.

“It was fine. I could just heart things and move things around. It felt like passively engaging,” he said. “Everybody was talking to each other.” 

This year, he is considering opening up the comment sections, which were previously closed. Now, he is considering allowing people to comment more, perhaps with some type of moderator that is not him. Part of the reason is that he is getting investor money that will involve an app, and more of a commenting section feels important to that.

“I’ve had some very high guardrails about how people can communicate,” he said. “I’m going to take one of them off and see what happens.” 

Culture Study: Revising policies and “getting out of the way”

Over the years, Anne Helen Petersen has changed how she interacts with readers. Blogging since the mid-2000s, “I used to respond to every email in my inbox, no matter the topic or tone, but that posture has long been revised,” she said, adding that it was too much emotional labor.

With the newsletter Culture Study, Petersen’s perspective is that she would rather have people have conversations with each other. So she is more likely to pose a question — and then sees her role as “largely getting out of the way.”

Culture Study is hosted on Substack, which allows setting up comment sections on certain topics. After posting a thread, she intentionally tries not to comment for at least an hour, if not more. By letting comments accumulate, people see they can talk to each other instead of assuming they are talking to her specifically. 

She said she enjoys engaging with readers, as long as they stay within basic guidelines she will remind readers about from time to time, which is generally to be kind. To help ensure the tone, she limits comments to paid subscribers and people who request complimentary subscriptions.

“I have thoughtful and empathetic and curious readers, and you see that most vividly in the comments sections,” she said. “It is always a pleasure to learn from these readers.” 

An Irritable Métis: Prioritize your time over replying to everyone 

Chris La Tray runs An Irritable Métis, a newsletter initially created as a companion piece to his book “Becoming Little Shell,” then built into its own thing.

He doesn’t interact with conversations as much as he used to for two reasons. First is the simple fact of the time it takes.

Second, and more importantly, he said, “If there is going to be engagement, I prefer it to be among the readers.” 

If he does respond, he’ll keep it brief. That’s not to say he doesn’t like to know what they feel connected to — hearing from folks all over the country is rewarding. On his book tour, connections made through the newsletter contributed to event success, he said.

Email is harder to wade through, though; he considers it an unmanageable deluge versus comments he can scan on a certain post.

“I often just select and delete the entire mass unread or the brain will simply overheat,” he said. “I really don’t like doing that, but I’ve learned that sometimes it’s absolutely necessary.”

For those considering starting a newsletter with community input, he counsels that commenter engagement can become a time sink — if you allow it to. Decide early, he said, the amount of effort you want reader engagement to become. If you are willing to expend regular time throughout the week monitoring and responding to comments, so be it. 

“I did not, and I am at a point where I am considering turning off comments entirely if only to spare myself the guilt I feel when I don’t have time for responses,” he said. “But then I worry that not allowing them at all will make me feel even more guilty.”

António Tadeia: Make comments a paid perk

António Tadeia covers Portuguese soccer with the self-titled newsletter he began in 2021. Sports fans are known for being intense; the comments sections on message boards for any sport are full of heated conversations and hot takes.

Tadeia’s readers have multiple ways to get in touch. They can comment on his posts via Substack, enter conversations via his private Discord server with chat rooms, and join his weekly YouTube live sessions for paying subscribers. 

“I try to answer every comment, as only paying subscribers have the possibility to comment, and they are not that many,” he said.

Sometimes, he also interacts on Twitter. “But I am trying to stop that, as that is where I tend to answer impulsively to the less rational comments,” he said. [Editor’s note: We know the platform is referred to as X, but it’ll always be Twitter to us here at Inbox Collective.]

He jokes he’s not organized enough to have a set time for it, rather, getting to it sporadically.

The enjoyable part? Meeting interesting people and interacting with the readers. 

“On the other hand, the most challenging thing is to read social media comments that hit right in the stomach that are so unfair, and knowing that you just have to let go and not answer, as an answer is all they want to spark a fire,” he said.

He’s at times been fed up with trolls on his livestream, eventually blocking them. “It was affecting me even in my day-to-day life. If you spend an intense hour of your day defending yourself from people who accuse you of the wrongdoings, you tend to get more reactive even with your loved ones,” he said. “So that was bad.”

He considered hiring moderators but felt his paid subscription wasn’t providing enough to support that; some of his subscribers offered to moderate for free but he felt that also wasn’t a fit. Eventually, he turned the stream into a perk for paying subscribers. When a troll kept returning with different aliases but the same credit card, he refunded and suspended the troll.

Overall, he finds reader interaction to be a vital piece of running a newsletter. People expect, he said, to interact with him.

“It’s important to keep people connected, to make them feel that they matter, because they do,” he said. “The newsletter business is a way of abolishing the middlemen in our connection with readers, so there better be one.”

Inbox Collective: Comments could be leads

It can take time to reply to readers — but for some newsletter operators, those replies are worth the time.

Take Dan Oshinsky, who runs this website. The core of his business is built around consulting, and by encouraging readers to reply to his newsletter, he’s found that he’s opening the door to conversations that might lead to new consulting gigs.

“When I first launched my business, I sent an email to my entire newsletter list inviting anyone to set up 30 minutes with me to chat about their challenges,” he said. “I ended up setting up more than 70 calls — and those calls directly led to new business. A few of the clients from those calls are still working with me six years later.”

Reader replies have sometimes led to unexpected opportunities. A few years ago, a reader based in Denmark wrote back to Dan’s welcome email to introduce himself — and after a back-and-forth, they agreed to partner on a workshop in Copenhagen for newsrooms looking to improve their email strategy. (They’ll be co-hosting another workshop this June in Copenhagen.)

“That’s more than $10,000 in revenue that I can directly attribute to a single email reply,” he said. “Yeah, it takes time to reply to all those emails, but year after year, I’ve seen that replying opens up all sorts of new doors for me.”

A Cup of Ambition: Rethink the mainstream comment models

Jessica Wilen’s audience is by nature a multitasking group — her newsletter is geared toward high-achieving working moms.

A Cup of Ambition launched after Wilen’s own career transition into executive coaching.

When she first began the newsletter, she attempted to encourage readers to engage in the comments section but had little success. “This was discouraging at first but makes total sense — most busy moms don’t have the time,” she said. “It’s been a shift for me to think about reader engagement as more than just comments and likes.”

One way she engages with readers is by offering paid readership access to an advice column. This boundary feels important to her, protecting her expertise as a coach and creating a private space for potentially personal questions. 

Last fall, she issued a call to her readers, asking to interview American moms living abroad. This turned into a four-part series; she said the connection she has between her readers built a foundation before the interview even began.

“Because people read my work every week, there was a sense of familiarity, and each interviewee was willing to open up and share personal things with me,” she said. “Going forward, I am definitely thinking of other ways I can source wisdom/experience from readers.”

Four takeaways for reader engagement

1.) Figure out what engagement looks like for your newsletter — Maybe you’re inviting readers to reply to your newsletter, inviting them to join you in a comment section or during a live chat, or starting a digital community where they can regularly engage with other readers. Feel free to start small and add more engagement opportunities when and where it makes sense for your newsletter.

2.) If you offer public engagement opportunities, set policies for your readers — It’s easy for a comment section or community, like Discord, to go from friendly to hostile. Write out a few rules for engagement, and make sure they’re posted in places where readers can see them. If someone breaks the rules, be willing to kick them out of the conversation. And whenever possible, encourage readers to talk with each other, not just you. Yes, you started the conversation, but in many communities, it’s the readers who keep the conversations going.

3.) Your relationship with readers may change over time — As Isaac Saul told Inbox Collective: “Early on, I’d have ten emails, so I’d spend an hour a day or two hours a day writing 1,000-word emails to readers who were writing about my political views. We’d have these rich, robust exchanges. Now I’m writing back one-sentence responses, or I’m not replying at all.” But that’s not necessarily a bad thing. Audience growth forced Isaac to create new ways to engage with readers at scale, like setting up polls. The engagement is still there — it just looks a little different than before.

4.) Feel free to take time away if you need to — Everyone has moments when they need to take time for themselves. You might need to prioritize a new project or time off around a holiday. That’s fine! Reader engagement is valuable, but if it becomes too much, give yourself the space to pull back and reevaluate how and when you engage with your readers.

Thanks to our sponsor

The stories you’re reading on inboxcollective.com are brought to you by Optimism, an email-first media company that publishes newsletters designed to educate, entertain, and inspire. They also work with external publishers to promote great content through their Curated By Optimism brands. Interested in learning more about how to reach Optimism’s audience of millions of subscribers? Get in touch here.