What Should I Do Next With My Newsletter? A Conversation With Claire Zulkey

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March 11, 2024

Claire Zulkey is the managing editor at Inbox Collective — she writes stories, but more importantly, she helps edit the stuff you read. But this is just a part-time gig for Claire: She’s got her own freelance writing career, and also her own newsletter, called Evil Witches, where she writes about parenting and motherhood. It started in 2018, born out of a Facebook group whose official tagline was, “Claire’s place to complain about kids and husbands.”

What started as a forum for Claire for parenting gripes turned into a successful — and profitable — side project. These days, Evil Witches readers can pay $5 a month or $45 a year for a paid subscription, and Claire has nearly 1,000 paying subscribers. (997, to be exact.) Another 13,500 readers get the free edition.

But whenever I’ve checked in with Claire lately, Evil Witches has been weighing on her. What started as a newsletter reaching family and friends has grown into something that reaches a sizable audience. And as that audience has grown, Claire’s noticed that readers are reaching out to her with weighty questions — stuff that should probably be directed towards a licensed therapist or parenting expert. Claire’s background is in reporting and writing, and she’s not sure how to handle those big topics.

The other issue is that Claire’s stuck in that place that a lot of newsletter writers hit: She’s making money off the newsletter, but not enough for it to be a full-time gig, and not enough to hire help to handle some of the tasks (from administrative work to research and editing) that she needs help with.

So what should she do next? Claire and I sat down at the end of February to talk about her newsletter and try to figure out what to do next. (At the end, Claire will explain what she did based on the conversation and how readers reacted to the changes.) We’re publishing the conversation with hopes it might help you think through the questions you should ask when you hit a roadblock with your newsletter.

—Dan Oshinsky

February 27, 2024

Dan Oshinsky  

This might be a good place to start: How do you feel about Evil Witches? You put a lot of time into it — how’s it going?

Claire Zulkey  

I mean, I’m proud of the work, and I get some really wonderful feedback. 

But as a freelancer, you’d never know exactly where your work is going to come from, which makes it hard to turn down work. So I have a lot of freelance work coming in, separate from Evil Witches, which is great, but it means I have less time to think about the newsletter, which involves a lot of creative brainstorming time and listening to people in my life. So I feel a sense of being overwhelmed by it.

I think some of the problems that people bring to me are more significant, and our children are getting older, and the world is getting more complicated. I’m getting questions about neurodiversity, and children who are genderqueer, and things like that. That gives me sort of a feeling of responsibility and fear. I hate to say this, but sometimes, I feel a sense of dread when I send out my newsletter. It’s a bummer of a feeling to send something out and have to brace yourself for how readers might respond.

Dan 

When did you notice a change in your attitude towards the newsletter?

Claire  

I think for me, the change happened last year. My kids started at a new school, and that has really changed our work schedule. We have to get the kids at 3 o’clock now — we used to have more of a 9-to-5. There’s nothing technically preventing us from working after the kids get home. But as you can imagine, you can’t concentrate the same way when your kid is around because of logistics, or you feel bad about it, or you’re just tired. And then for better or for worse, I got way more work at the same time that my kids made that school change. Part of it is simply having fewer hours per day to work. 

As the kids have gotten older, the content in Evil Witches changed with it. I hate this phrase, but: Bigger kids, bigger problems. Talking about middle schoolers on social media or how to deal with kids using hateful language online is a lot more serious than writing about a diaper blowout. I think that’s a big part of it.

I think that maybe as the audience has gotten bigger, more people have come to me as an expert and brought bigger questions to me. I’m always going to do my best to answer them. So much of my early writing was silly or goofy, but you can’t be goofy when you’re talking about homelessness or talking about addiction. 

And I’ve tried to be as inclusive as possible, but also, to a certain extent, that can water down your perspective. If I’m trying to talk to everybody, I’m not really talking to anybody.

Dan 

You’re not positioning yourself as a parenting expert. You’re a writer and a mom who also happens to produce a newsletter for moms. But as you think about what’s happening right now with Evil Witches, does it feel like your readers expect you to have some sort of expertise that you may not actually have?

Claire

This kind of makes me realize that some of this is my problem. I think that part of the issue is that when readers email me with a tough question, I tend to say, “Yes, let me look into that, let me try to help you.” Maybe because I feel like it’s an honor that someone would ask me in the first place, you know, where I don’t want to turn down an idea.

Dan 

I wanted to ask a big question: Do you feel like you could walk away from Evil Witches today if you needed to?

Claire 

I honestly fantasize about it a lot.

It feels weird and wrong to think about turning down the money I make from Evil Witches. But at the same time, things don’t always work out the way you expect them to work out, right?

Dan  

Of course. The reason I asked the question is that if the answer is “yes,” then you’d probably also be willing to make a number of other changes. Those changes could be pretty radical, like shutting down the newsletter. They could also be more incremental, like adjusting your publishing schedule. 

Let me ask this: No matter what potentially changes, is there something that you want to keep at the core of Evil Witches?

Claire  

I think what makes it great is also what makes it stressful. All of my newsletters are inspired by real people’s problems. And so I feel a real sense of responsibility in terms of treating that very carefully, and with gratitude, and not flippantly. 

With Evil Witches, I wanted other moms to know it’s okay to complain about your family or your spouse. You don’t even have to question whether you can do these things and be a good mom. We can just assume that we’re all really trying our best as parents and citizens of the world. And we can also talk about the, you know, inherent difficulties and inequities, and laugh about things and make fun of our kids and things like that. 

Being able to also like flip subjects is special. Not only focusing on kids, you know, but being able to talk about pop culture and work and relationships and fashion and cooking. What I think is special about it is that it’s not only about children or marriage. We’re people who happen to be mothers. These are all the things that we care about.

Dan 

Something I really like about what you just said is the idea that as the audience has expanded, it makes sense that the topics you write about could expand as well. There’s no reason you couldn’t expand the definition for what Evil Witches can be. And that might also allow you to touch on subjects that could be less controversial or less intense. With tough subjects, those might be things you talk about, but not twice a week — you get into them every once in a while.

Let me ask this: Some of this stress that you’re feeling around the newsletter — is that being put on you by the audience? Or is that something that you are putting on yourself?

Claire  

Oh, I put it on myself, 100%. 

You know, Evil Witches spun out of this Facebook group that I founded. But so much has changed over the past few years. I’m on Facebook less. Then of course, there’s the 2016 and 2020 election, and then the pandemic, and it’s just, like, the internet got a lot less fun, right? Things got a lot more serious and high stress.

Dan  

I completely agree. When you first started blogging and creating stuff on the internet, 20+ years ago, the internet was really fun and weird and silly and…

Claire  

…anonymous, and you could fuck around, make mistakes, or be silly or be really passionate. It was a good place to play.

Dan  

And now, even for someone like you writing a newsletter for moms, there’s a professionalism that comes into it, which maybe wouldn’t have existed a couple years ago. Part of that’s because some of the audience is paying for your newsletter. But still, it’s a different version of the web. 

Let me ask about the changes you could make for your newsletter. I see a few options. One is to change the frequency of Evil Witches. Right now, you’re publishing twice a week. You could go down to once a week. What do you think about that idea?

Claire  

I mean, I love the idea. But my immediate question is: Do you change the subscription fee? Are people going to be mad and say, “Hold on, I paid for this thing that you said would come twice a week, and now it’s not?” Are people going to feel shortchanged? Do I need to address that?

Dan 

You’re charging right now $45 a year for a subscription. Which, in terms of subscription fees, I think is relatively reasonable. If you were charging $450 a year and you changed the cadence, readers might say, “I paid you a lot of money for this. I expected a certain thing.” But in this case, you’ve never made promises that you will fulfill a certain content or story quota, or a certain number of live chats with readers. I don’t think you’re breaking a promise here.

Another option is that you could keep the twice-a-week cadence, but occasionally schedule breaks where you might not publish for a few weeks. You could even build it around your kids’ school schedule: During spring, summer, and winter break, you’d tell readers, “I’m going to take a little time off to reset so I can keep making good stuff for you guys.” 

One thing in your favor is that your audience knows the newsletter is produced entirely by you, and your readers, for the most part, are parents like you. So it’s possible they could get mad at you and go, “Claire, I need you 100 times a year in my inbox!” But I think it’s more likely they would say, “I get it. I’m a parent too, and I know what it’s like to struggle balancing work and parenting. No worries — take your time, and I’ll see you in a couple of weeks when you’re back.”

I think you could also tell your paying audience that if they feel like they’re not getting value due to the new schedule, they can reach out to you for either a full refund or to have a few months of access added to their subscription term at no charge. It’d be a way to acknowledge that you appreciate their support and want them to know that you’re willing to find ways to make things work.

What do you think about that?

Claire 

Yeah, I like that idea. Sometimes I try to remind myself, “Your audience is you. And you would never expect your friend to be working at 11 p.m. on a school night. You would tell her to go to bed and relax.” So, I try to tell myself that — but I don’t always listen. 

I remember when I tested positive for COVID-19. And my family, we all got it within like a week of each other. And then a tree fell on our house. So I told readers, “Hey, I gotta take a break.” But I felt so bad about it that I completely paused subscriptions — I wasn’t charging people during that break. And I remember a reader writing in to say, “You didn’t have to do that.” But I didn’t know what the options were at the time.

Dan 

Let’s try to put this in perspective. You’re a writer putting this newsletter out into the world on a regular basis. Whether it’s the audience putting the pressure on you, or you putting the pressure on yourself, or some combination of the two, there are outside forces that are weighing on you. And it makes sense to me as a recipient of it, that you would have to make adjustments to deal with those pressures.

The adjustment could be you saying: I want to keep doing this work, but if I’m going to keep doing it, I’m going to charge a lot more for it. This subscription doesn’t cost $45 a year anymore — it costs $150 a year. You’d tell readers: “I’m trying to put this work out, and I want to make it good. But in order to make it good, I need to charge more, so that way, I can take on less freelance stuff, and really focus on Evil Witches in a bigger way. That’s how I’m going to make it work.”

Or you could go the other way and say: “I’m keeping the subscription price as it is, but I’ll do a little bit less. I’ll be open with you about how I’m going to do less.” 

But Claire, based on the conversation today and ones we’ve had over the past year, the path that you’re on right now seems a little unsustainable in the long run. You’re not at the point where you’re saying that you’re at the limit of your capabilities and have to stop this thing. You’re not there. But if you did nothing, I can imagine a world in which we’re having this conversation in six or nine months and you’re saying, “I can’t do this anymore.”

Claire  

Yeah, or that I’m not having fun. And that’s one of the big tenets. Readers can tell if you’re not having fun and you’re not interested in it, you know? So that’s at the root of it, too. What am I delivering if I’m not having a good time?

Dan  

I’ve met plenty of newsletter operators who are extremely professional from Day 1. And I don’t mean professional in a bad way. They come into it with the goal of making their newsletter their full-time job. Every decision they make is a business decision.

Yours is a case where this thing came out of really a lot of personal decisions. You built an audience, you’ve built out a subscription business — this is credit to you and the amazing work you’ve done. But it didn’t start from a place where you said, ”I want to build a six-figure newsletter business.” You wanted to make something that you and your friends would want to read, and it’s grown from there. So if you’re not enjoying it, if it’s not fun, how do we start to strip away some of the elements that are not fun and get you back to a place where it can be a little bit more fun, or give you a room to experiment, or just make it something that you actually look forward to producing it. Evil Witches is just a part of your income — there’s no world in which you should be doing a thing that makes you unhappy.

Claire  

I think I know the answer to this, but if I stopped doing my newsletter, would I still be qualified to work for Inbox Collective?

Dan 

Oh, Claire, I would fire you immediately. [laughs]

Claire 

This is my exit interview. [laughs]

Dan  

For me, it was a bonus that you worked in newsletters. But I didn’t hire you because you were a newsletter expert — I hired you because I thought you were a smart person, a good editor, a good writer, and could help me think through some of these things. I also appreciated the fact that you came from a different background, you didn’t have the same sort of, you know, news background that I did in terms of working at the places that I worked, which meant that you were going to come up with different ideas and perspectives. I think it’s the same reason that your audience likes hearing from you. 

I will say: I hope you keep building Evil Witches. I know your audience is primarily moms, but there are certainly dads like me who read it and get value from it. But you’ve got to figure out the path forward that makes this right for Claire. And if it works for you, your audience will understand that, and it’ll work for them, too.

Claire 

We’re going to take the kids on a trip soon, and then I’m going to rent out a cabin in the woods for myself for my birthday to just, like, read and watch TV and whatever. So I’m thinking about telling my readers, “Hey, guys, I’m taking a month break, you know, for all of those reasons.”

I do also love the idea of maybe going once a week, or every other week with a free piece versus a subscription piece. That would take a lot of pressure off.

Dan  

If that’s the path you go — and to me, it makes a lot of sense — you can announce it to the audience and see what happens. If readers unsubscribe, if readers decide to cancel their subscription, okay. But I think there’s a very good chance your audience says, “If we hear from you 50 times a year instead of 100, that’s okay. We like you, and as long as we keep getting you in our inbox on a regular basis, we’re going to be happy.”

There’s no right answer here, but you have a life, you have a family, you have other stuff that you’re doing besides writing a newsletter. So, at some point, you have to decide what makes sense for you. Yes, Evil Witches makes you some money, but that’s not why you should keep it going forever.

Claire  

I used to see the money as a fun bonus. Well, I mean, it certainly was — the money is long overdue for all the free writing that came up to this point. And I certainly deserve it and earn it as a reporter. But I do think I used to look at it more as gravy and not a chunk of my income.

June 17, 2024

On the other side of my talk with Dan, I put the following into place on his suggestion:

• I announced a full publishing hiatus of a month or so, coinciding with my kids’ sports schedule. 
• When I returned, as I told my readers, I would do so with a reduced publishing schedule. One email per week; every other week for the free readers. 

As I had perhaps secretly suspected but didn’t want to count on, many of my readers had a response along the lines of “Good for you!” Not only is my readership strongly in favor of a woman/working mom drawing boundaries and stating what she needs, many readers said that they really don’t want more email anyway. Fewer newsletters wasn’t a bad thing.

And I get that!

On the other side of this discussion and my little break(down) I think there were two things going on with me that caused burnout and stress. 

The first is the nature of newsletters, which, if you want to make money, requires you to care about your paid signups, your conversion rates, your unsubscribes, and the people who read your work and talk to you. When a newsletter grows, as mine has, from earning $0 per year to tens of thousands of dollars, the stakes can naturally feel higher because, financially, at this point they are! I like a lot of things about publishing on Substack, but I wish I could go back in time and take its suggested publishing cadence less seriously. And I also wish publishers had to navigate to see metrics instead of having them shown to you on the landing page, because sometimes I just want to start a post without thinking about numbers. I’m a writer at heart and I prefer to log into a blank page and not a chart and stats. 

To be very candid, my second issue at the time was just plain old mental health. I sometimes deal with anxiety and depression and am a mom and “of a certain age,” so at a certain point, my newsletter, like other obligations in my life, became tinged with overwhelm and stress, like I was letting people down. 

Of course I care about the quality of my work and don’t prefer to piss off anybody, but newsletters are a long game, and if you start feeling overwhelmed and nervous, each time you send an email (and don’t have anyone else to delegate to), this is not sustainable, as Dan pointed out.

During my hiatus, I adjusted some things in my mental health toolkit and came back with a mindset I consider more appropriate and tolerable. No need to stay up late and get up early to push out a newsletter on Wednesday when I can make it better and send it Thursday. I can skip a day if my kid is home sick. My readers are people like me. I wouldn’t want someone I care about to do these things. The only emails I can imagine pining to receive involve getting work, money, or news about my health or my family. 

To my humbled and pleasant surprise:

• 6 readers became paid subscribers after I announced my hiatus and scaled-back publishing schedule.
• I did lose 22 paying subscribers over the course of the month, but none told me the reason they canceled was because of the hiatus.
• The free audience grew — even though I didn’t send any newsletters for a month. From my last pre-hiatus newsletter on April 15 to my first post-hiatus one on May 22, I added 752 free subscribers.

But more importantly, I feel much less pressure and anxiety about my newsletter now, which is for the good of the product. I know that whatever I work on, the result is better if I am engaged and relaxed.

If you’re like me and are in a similar stressed-out place to where I was with my newsletter (or whatever you’re working on!), my conversation with Dan and resulting action items revealed two pieces of advice I’d share. One is that it’s essential to touch base (using real human voices or faces) more than occasionally with colleagues. Even if they don’t write a newsletter similar to yours, expressing your concerns and frustrations to someone who gets it is essential to let off steam and to get new ideas. Writing is solitary, and even for those of us who sometimes crave solitude, too much isn’t good for you. Saying things out loud helps put things in perspective.

And related: take care of yourself. I’m hard-pressed to think of an email that you need to send, even if you make a lot of money off your newsletter and a lot of people count on it. Is that newsletter more important than your physical health, mental health, or family? 

Sleep, eat, go outside, smile, see people, and send emails: in that order.

—Claire Zulkey

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