I launched my newsletter, Evil Witches, in 2018 as an experiment to see if moms wanted to read the type of parenting writing I had been practicing online and on social media: irreverent, progressive, cynical, multifaceted and curious. Something that was centered around the mother — not the child — with an aversion to obligatory sap, apologies, or happy endings.
Five years later, I’ve grown my audience to over 11,000 subscribers and have so far earned over $73,000 total from the project. And yet many days, I wake up thinking I have no idea what I’ll send out that week, worrying if I have lost touch with what people want, wondering when it will be uncovered that I’m making this all up as I go. Will everyone ask for their money back?
But the years and the numbers seem to indicate that some of this has been working, despite my anxiety. I still don’t have all the answers — I can’t tell you how to make a newsletter work with no drama, no mystery, and only well-paid, well-used time, but I have learned a few things over the years that I think are worth sharing.
1.) Knowing what you don’t want to do is as important as knowing what you do want.
At one point early on, a friend of mine with a marketing agency ran Evil Witches as a potential test client. Her team advised me to research other newsletters in the same vein as mine. They told me to outline what I saw in these newsletters and make note of what I didn’t respond to as well as what I did.
I found myself resistant to newsletters that included lists of out-links, like things to read, buy, or share. I know how cross-traffic works and that readers do appreciate curated choices by creators they trust and enjoy. But I couldn’t help feeling like I had a list of homework — tabs to check out — after I read many of these issues. So that led to an editorial choice: I would try to link out sparingly from my issues. I wanted each newsletter to be something someone could read in bed or in the bathroom before she had to work or take care of family matters.
That choice has probably cost me — I’ve missed out on opportunities for cross-promotion with other newsletters and websites and left money on the table from affiliate links. But it’s also benefited me in time saved checking links and decisions about what I’ll promote or not promote, among other logistics. Moreover, readers have told me that they enjoy the capsule-like feel of each issue. That’s all thanks to my benchmarking exercise, which helped me see what was already out there and saved me from replicating an existing newsletter.
2.) Being your own boss doesn’t get any easier.
Something I like about freelance writing assignments is that another person is telling me when my piece is due, how long it needs to be, and what it needs to look like. I have a hard time treating my newsletter as another freelance assignment, maybe because so much of it is personal or maybe because it still feels fun. That means it often gets pushed to the bottom of my to-do list. I have to feel “in the mood,” which isn’t a luxury I can afford when someone else is my boss.
There’s also the matter of figuring out how to convert readers to paying subscribers. One idea that we’ve covered on this site is offering readers a peek behind the curtain to bump conversions. I have considered this, but I feel like so much of my “peek” would just involve procrastination and/or feeling bad about my progress.
It doesn’t help that when you run a personal newsletter like I do, it’s hard not to take things personally. If you work hard on an issue and people love it, it usually drives paying subscriptions — which must mean I did good. If something doesn’t really get a response, it must mean I’m completely out of touch with what people want. That anxiety is always there.
I could save myself some time trying to set up systems and routines to automate the work. I could also be gentler on myself and feel good about what I have done instead of berating myself for not being more on the ball.
3.) Set up a separate email account for your newsletter.
This took an absurd amount of time for me to figure out. At one point, I put out a call for input from readers on my newsletter and asked them to reply to my personal email address. My request got an unexpectedly robust response. The number of readers emailing me enthusiastically saying, “I’m interested!” or “I’m in!” overloaded me as they came interspersed with emails related to my freelance work as well as my family life.
So I set up a separate Gmail account for all my newsletter-related emails. I now feel less of a sense of immediacy when it comes to my community, which can cut both ways — I am less responsive, which may be bad for business. Still, with a mailbox I have to check in on separately, I feel more in control of my time and struggle less with the aspect of mentally swinging from project to project.
4.) It’s not easy to get ahead with publishing.
In 2019, I tried to stockpile some future issues so I’d have them ready to roll at a moment’s notice and never worry whether I was out of material. Then the pandemic hit, and all these topics — many of which leaned on socializing, school, and seeing family — seemed completely out of step with reality. Four years later, some of these issues have become relevant again — but I am different now, and so are my readers, and so are our families.
There may be some newsletters out there based on purely evergreen or non-timely topics that can be pre-written and ready to go for the future, but I have learned this is hard to do in a newsletter format based on personal experiences and/or current events.
It’s good to think and plan ahead, of course, but you also simply have to trust the process. You will discover new material, or someone will suggest an idea for an issue, which will carry you through. For me, that’s more practical than going into some newsletter pantry, dusting off a piece I wrote long ago, and hoping it will still feel fresh and relevant.
5.) Numbers are not always your friend.
Subscriber numbers. Paid subscriber numbers. Social media followers. Conversion numbers.
Comparison is the thief of joy. The less frequently I check my stats, the less I obsess over why I haven’t performed better.
And as I wrote about earlier this year, I’m OK with slow growth:
“The newsletter brings in money — not enough to be my only mode of income, but that’s not my goal. I like having the flexibility to build out multiple revenue streams, including my newsletter, freelance writing, and editing work.”
If I obsess with the numbers, I lose sight of my big-picture goals and let it affect my mood. To that end, I turned off notifications alerting me when someone has unsubscribed from Evil Witches. People are entitled to streamline their email inboxes, and I am entitled not to worry about it.
6.) Proofread on your phone.
Reading a newsletter issue on my phone in draft mode always reveals both content and formatting issues I don’t see on my desktop. Plus, it more accurately mimics a variety of reader experiences. By proofreading on my phone, I can make sure both images and text will look good no matter how my readers open the newsletter.
7.) Passion projects are nerve-wracking.
If you are a creative type and want to put your work out there, there is a risk that people won’t buy what you’re trying to sell. For some reason, I am the type of person who pursues these situations despite hating the inevitable humbling process that comes with the territory. Every time I send an issue, I fret a little bit over whether nobody will read it, or whether it will have a huge mistake in it, or whether I will get a negative response — or no response at all.
I can’t tell whether this type of routine is good or bad for me, but it’s what I do, and I haven’t figured out how to not sweat it. But that’s the gamble! Besides, I don’t think I would want to read something by someone who wasn’t concerned about how their work was being received.
8.) Trust your experience
Earlier this year, a client hired me to ghostwrite a newsletter series for him, but we quickly came to an impasse. I thought it was essential that I communicate with him directly about the project; he was not available and expected me to run the project entirely based on old materials.
I already periodically dip into impostor syndrome, and this client also happened to be a wealthy, connected entrepreneur. Was there something he knew that I didn’t about how to do this? For a while, I wrung my hands over my inability to make this project work. Then I came to a realization: I might have a modest platform with modest goals, but I’ve been writing online and selling my work to people for over 20 years. I do this professionally, and I do know what I’m doing. He might be a professional entrepreneur, but I’m a professional writer/editor. The client and I parted ways amicably, and I felt relieved and empowered.
What I’ve learned from this is to trust my own expertise and experience. My newsletter is emblematic of my writing career. I am not the richest, most influential, or most famous writer in the world, but I am legit, and so is my process.
9.) Evolution is essential.
I often crave a “set it and forget it” system that will allow me to sink mindlessly and comfortably into a routine, but things never seem to work that way.
When I started Evil Witches, I published on Wix. Each issue was much longer, and everything I wrote was free to read. I later migrated to Substack, where I toyed some more with the project, seeing if people responded before I turned on paid subscriptions. (They did).
The newsletter has further evolved in terms of tone and format as I’ve worked on this longer, my kids have gotten older, the pandemic has happened, my audience has grown, and I’ve retreated from social media.
I have started a lot of long-term open-ended projects in my life, like my old blog, my reading series, and several book manuscripts published and unpublished. It has been a good life lesson to take on new projects, take them seriously, and know they don’t have to last or look a certain way forever. My motto for Evil Witches is “I don’t know what I’m doing and I’m making this up as I go.” Other editors should feel emboldened to play, experiment, pick up, and discard new ideas without worrying too much about whether you are a paragon of consistency.
10.) Talk to other newsletter operators.
Working at home (or at the library, or at a coffee shop, or in the car) can be comfy and convenient, but it gets lonely operating in a vacuum. Readers or subscriber data may tell me individually how I’m doing, but when I toil on my own for too long, I feel disconnected from my overall mission of putting out the kind of parenting pieces I want to see in the world.
Checking in with colleagues like The Ankler’s Richard Rushfield, an early mentor of mine, or other writers like The Small Bow’s A.J. Daulerio helps me realize that everyone in this field struggles. They have the same wonderings about whether they should put more time into their marketing strategy, what to do when the content dries up, or about subscriber counts or income or whether they’re on the right platform.
Sometimes I get good ideas for stories from these conversations, but often, I just feel less alone, which might even be more valuable. The lesson is, if you have the chance to speak with another newsletter operator, whether over phone, Zoom, or in person, take it.
11.) Your readers will help you run the newsletter.
While I will always feel a certain level of stage fright when I send out an issue, the number of readers who want to help me out or be a part of the project makes me feel like I’m on the right track and makes my job easier. The money and professional satisfaction I get from my newsletter is great, but what is really humbling (in a good way!) is when a reader reaches out with an idea for an issue or volunteers to be an expert for something I’m covering or expresses interest in sharing some news of theirs with other readers. It’s a feeling not unlike throwing a party and realizing that you have reached the point where the guests have all made themselves comfortable, found people to talk to, and are enjoying the evening. In other words, a success.
If you put enough out there, at a certain point, people give something back to you. Then you can put those ideas back into the newsletter, and the cycle continues. And maybe, just maybe, you can relax and have fun.
