Summer Brennan on Her Dangerously Good Newsletters and How They Serve Her Writing Career
Bonus material from Launch & Grow a Newsletter to Boost Your Writing Career
Hey writers!
As a special treat for finishing our first week together, we’re getting the insider scoop from one of my favorite newsletter writers.
takes us inside her — not one, but TWO — wildly popular newsletters.
What’s the basic premise and tagline of your newsletter(s)?
SB: I actually have two active newsletters. My newest, called
, is set up as a year-long workshop for people looking to transform their writing practice. That’s the tagline — “transform your writing practice” — and so far, I’ve heard from participants that it’s already working to do just that, which is great. It has a very active community of dedicated writers, and honestly, it’s already changing my life and work, too. My first newsletter, , is a collection of essays about life and writing (I should probably update the tagline). There are frequent short personal essays I call “notebook entries” and longer pieces on culture, writing craft, or the creative life. A Writer’s Notebook is also the home to my twice-yearly free writing workshop, Essay Camp.
When and why did you start your newsletter?
SB: I started my first newsletter in late 2020, early 2021. I really started it for me, without any idea of monetizing it, because I felt a need to transform my own relationship to my work and to my creativity. I needed to start making work I was excited about, that came from a true place within myself, or I was in danger of losing something, of drowning. I was working as a freelance journalist and essayist. I’d won awards, but I had also experienced a string of frustrating experiences that left me feeling discouraged and depressed about the industry. So I invented a specific writing practice for myself that I call the “five things essay,” and started doing that in December of 2020. It seemed to unlock something. I started posting on my website, then moved to a newsletter a month or so later. Last year, I started to fantasize about starting this second newsletter in the form of a workshop, so after testing out the concept on myself for a year to work out the bugs, I finally launched that last month. I studied writing with Mary Oliver for four years, she was my mentor, and I’ve always wanted to try and teach in the way that she taught me. It might sound cheesy, but I took this questionnaire about “finding your purpose,” and one of my big things was helping people and making them feel less alone. Your “purpose” is supposed to be at the junction of what you’re good at and what you deeply care about. So, a Year of Writing Dangerously really came out of that.
Who’s your main audience?
SB: Anyone. I have readers of all ages, from all over the world. For my workshops and craft essays, my readers tend to be other writers, people who care about writing, who want to advance their writing career and take control of their creative trajectory, or who just want to be more present in their daily lives. In my workshops, I have both young college students and people who have just retired and are looking for their next adventure. That said, I think I also tend to attract a high number of dreamers and sensitive souls.
How is your newsletter differentiated from the other newsletters in your niche?
SB: I’m not sure, to be honest. I try not to compare myself or strategize in that way. I just kind of do my own thing. If I had to say what makes A Year of Writing Dangerously different from some other online writing workshops, I’d say it’s that it’s not canned. For example, with MasterClass, which I love, by the way, it’s all one-way. It’s ore-decided. That’s not the case with what I’m doing. It’s personalized and dynamic. I’m treating it like a live, ongoing, in-person course, as though I were teaching at a university. I have what you could call a lesson plan, but everything is happening in real-time. I answer student emails every day; I record videos based on the questions and discussions I’m seeing in the chat that week. There’s an energy to it that I really love.
What’s your editorial strategy?
SB: I’m usually pretty spontaneous with my posting, but I noticed my essays were better when I gave them a few weeks to percolate, so I’m trying to do more of that when appropriate. For A Writer’s Notebook, I don’t have a set schedule, but tend to post once or twice a week, sometimes more when appropriate, sometimes less. A Year of Writing Dangerously is more regimented. There are five six-week sessions throughout the year, with posts and/or chat threads for every day of those sessions. Even then, I’m writing the individual posts the day before I publish them, so there isn’t a sense of things getting stale. I always like to give my readers options — they can check or uncheck which stuff they want to get in their inbox.
How many subscribers do you have?
SB: In total, I have over 18,500 subscribers.
Do you offer paid memberships? If so, explain when and why you turned that on, what your subscription offering includes, the cost, how many subscribers are part of your paid community, and any takeaways from going paid.
SB: About 10-15% of my readers are paid subscribers. I turned that on from the beginning. I was in this position where my options were very limited, and I needed to pay my bills and had no idea how to do that. The percentage of paid subscribers fluctuates as new readers come in and then decide to subscribe to the paid option or not. With A Writer’s Notebook, there is a mix of free and paywalled essays, although the workshops delivered via that newsletter are always free. A Year of Writing Dangerously is 100% paid posts only, with periodical updates that go out to those on the free list.
Have you tried any other methods of monetization?
SB: For my newsletters? No. I started out on Patreon in the beginning but then moved to Substack. My workshops are all administered through Substack.
Tell us about your newsletter’s growth trajectory. What have been the most effective ways for you to promote your newsletter? Did you have any growth spurts, and what did you learn from those?
SB: I haven’t been an overnight success. For my first newsletter, my story is really more one of steady and incremental growth over the space of three years, with little spurts when I write something popular. With my second newsletter, I think because I had already developed those relationships with readers, the growth was immediate. In the beginning, I know that a lot of readers found me through Twitter, where I had a fairly large following built up over a decade of doing journalism, publishing books, and saying stupid and occasionally funny things online. Now I don’t really do that much outside of Substack to promote my work. I share occasionally on Instagram or other social platforms, but it’s not a hard sell. My growth now is mostly through recommendations and word of mouth.
What’s been your most popular content, and your guess as to why?
SB: I think a lot of people really like my workshops, and they like when I share essays that resonate with them, either about life in general or about creative work.
How has your newsletter served your career as an author?
SB: My newsletters are my full-time job, and doing this has changed my life. It has changed my writing, helped my creativity, and generated ideas for work outside the platform. I mean, I can afford to go to the dentist, whereas before, I could not. I suspect it does help sell books, but I only started including links to my books at the bottom of my posts relatively recently. I haven’t put a lot of energy into writing outside of Substack lately, to be honest, but I don’t want to neglect other short-form publishing options forever. In the fall, I decided to submit an essay that I wrote for my Substack newsletter to a literary magazine instead, and it was accepted. The funny thing, though, is that then I have to wait about four months before it can be read! It’s such a different beast. A few editors have approached me after reading my newsletter work and asked me to write for them. Financially, it makes more sense for me to publish on Substack since it pays me more than the freelance rates. But there’s a lot of value in working with editors that goes beyond whatever fee you get from the magazine. More than helping with bylines, I think Substack has helped improve the quality of my work.
What’s your #1 tip for writers who want to start a newsletter?
SB: Be patient; your path may not look like anybody else’s. Not everyone is an overnight success. Most writers are not overnight successes, as it tends to run against the natural process of creative development and reader discovery.
What’s your #1 tip for writers trying to grow their existing newsletter?
SB: If you want growth, post free content. It’s the easiest way for people to discover you and for your work to be shared. Write about what you’re truly passionate about, the things you really care about, rather than what you think might be popular or lucrative. You don’t need a niche. Your niche is you. Following too many formulas will just result in formulaic work.
Shout out another writer-newsletter that you admire and enjoy consuming.
SB: Oh gosh, just three? There are so many. I used to be a Twitter addict, and now I’m a Substack addict, which feels much healthier. I love the newsletters run by Sari Botton—
, , and . I always read them. One of my childhood friends and my auntie both have newsletters that I’d love to shout out too — one is the astrology newsletter , and the other is by , a writing coach based in Northern California.
Anything else you’d like to add?
SB: Thank you for inviting me. I’m so grateful for the community I’ve been able to find here.
Thank you so much to Summer for sharing her newsletter wisdom.
 | A guest post by
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Thanks for the shout out Summer!
Thank you, Summer and Courtney! <3