Five Writers on the Joys and Challenges of Substack and Midlife
Go "behind the scenes" with 5 midlife Substackers
This fall I put out a call for members of our Midstack community to take our Midstack Survey, a set of questions about writing on Substack. Not surprisingly, we received quite a lot of thoughtful responses.
I’d like this to be a semi-regular Midstack feature. I think you’ll find it inspiring and informative to go “behind the scenes” with midlife Substackers and learn about their challenges and successes.
Today we are featuring five midlife Substackers. Each has a unique voice and a unique audience.
Amanda Schuster who writes
Karen Wesley who writes
Jodi Sh. Doff who writes
Erica Lucast Stonestreet who writes
Lisa Renee who writes
(These interviews have been lightly edited for length and clarity.)
Would you like to take our Midstack Questionnaire?
What do you write about on Substack? Who do you write for?
Amanda: Since most of my editorial work and book writing has been focused on wine, cocktails, and spirits, that's still my main focus. However, since I am not writing for a formal publication, I can veer out of my lane and write about music and personal observations.
Karen: I am writing as I heal from intense mothering two autistic sons, self-care, mental health, parenting adults, long-term marriage, caregiving and Black Life in America. I write for moms with special needs children, mothers who need self-care, self-compassion and therapy. I write for married people. Women who decide not to have children, or get married. I write for autistic adults, and those with ADHD. I write for writers!
Jodi: I write about caregiving and living with an elderly parent, about doing it alone with no partner, children or siblings for support, about aging myself and trying to stay sober and sane through it all. I write to record who we are, who we were, who she is, who I am for those who are where I am now & for you who expect to be here. Because we cannot, should not, and do not have to do this alone.
Erica: I write about the philosophy that pops up in everyday life. And the value of the liberal arts. Mostly I tackle questions that connect to who we are and how to live. Meaning in life has been a theme lately. I write about love and care as moral forces. I write for intelligent, curious readers who are open to critiques of modern culture and who are interested in the real-world impact of ideas. For people who are interested in the layers of meaning embedded in everyday ideas.
Lisa: I write personal essays about my (getting late) midlife. Anything that falls out of my head onto the page is fair game. I write for myself, but also to connect with others who can relate. I love writing, but also finding my people.
Why did you start your Substack?
Amanda: I found traditional editorial work to be so vexing lately — pay is worse and more infrequent than ever before, it takes months for a topic to be published, pitches go unanswered. Here I can write about what I want to, how I want to, when I want to.
Karen: I want the freedom to write whatever I am feeling, and say the things you're thinking but may not say out loud. I want to be in community with other writers to share the experience of writing. After years of writing earning very little, I want to write to find an audience who values my words enough to pay for them.
Jodi: I’m a sixty-something, single, childless, sober writer who’s spent years writing about sex, drugs, and drunkenness. Shortly after turning thirty-three I got sober. I taught writing while working full-time in a nonprofit & caring for my elderly mother as she skidded down the road to from mild cognitive impairment to full-blown dementia. I've been writing about her and us for ages, I chose to focus on the caregiving, the change in our relationship and aging because I write what I know and honestly, that's the entire focus of my world these days. And I've had many folks, friends and strangers, come to me for direction or support, so much so that I codified some of my advice and resources and it grew...into this.
Erica: Two reasons. Most immediately, I'm trying to get a book published and I'm told it can help to have a platform. More broadly, I think philosophy needs a boost in the collective imagination and want to contribute to letting the world know its value. Before I had kids, I was writing periodic emails to a list of friends, and now that my kids are teens, I find I have a little more mental space and I've missed writing.
Lisa: I started this project to hold myself accountable to a writing schedule, but also to connect with others.
How has your publication changed since you first launched it?
Amanda: I'm writing less frequently, but it feels much less like "work" than it used to.
Karen: It has grown tremendously! I have found my people!
Jodi: It still hasn't completely jelled as it were. I thought I'd have more time to focus on work and essays specifically for paid subscribers. I thought feedback wasn't important to me. I'd much prefer to have it be completely free and have more interaction, but I'm not sure how to back track since I do have about 40 paid subscribers, many who paid annually.
Erica: It's only been since May, so it's probably too soon to tell. I'm not sure it's had time to evolve yet.
Lisa: This past year, I've been much less present. Not by desire or design — it's been quite a year! I used to publish weekly and now I'm lucky if I get something going monthly. Hoping to change that!
Get involved in various writing communities, collectives, cohorts, and classes. Writing in community helps you stay engaged and focused. Read other writers, engage in their comments, share their work, and you will find reciprocation. Engage on Notes, be positive while also being honest about your writing struggles.
What have been your biggest challenges and successes on Substack?
Amanda: The biggest challenge is finding an audience and engagement. I find that I have very specific fans, but mostly the same few people engage. I wish there was more of that. I wish I had more feedback about my delivery. Success? That anyone is reading and subscribing at all!
Karen: The biggest success is the community of writers that I have built. I have been sought out to write for other publications, and have been featured by several writers. I'm building a new loyal audience.
Jodi: Finding the time, being consistent, keeping up with reading other 'stacks, trying not to get caught up in the whole push to monetize, schemes to grow readership in anything other than an organic manner.
Erica: Challenge? Getting the word out and getting subscribers. Successes are writing regularly and finding things to write about.
Lisa: My biggest challenge has been sticking to a writing schedule (especially in 2024, where it all went out the window) and feeling like I have something worthy to say (a common plague among writers). My successes? VIPs pushing around my essay, "Leave me alone, but don't leave me"; a collab with another Substack writer, Elizabeth Marro; doing a brief interview with Jami Attenberg; and Oldster Magazine published my piece, "Now We Are 60." I consider all the many friends and connections made on SS to be quite a success, too.
What advice would you give another writer starting out on Substack?
Amanda: My advice is go with your gut, and don't treat it like writing for a magazine. It can be more personal. Use your voice. What doesn't work for me has been when I've tried too hard to please people who aren't me. Write for YOU. Also, you deserved to be paid for writing. Don't give too much away for free. That's how many of us are in this boat in the first place.
Karen: Get involved in various writing communities, collectives, cohorts, and classes. Writing in community helps you stay engaged and focused. Read other writers, engage in their comments, share their work, and you will find reciprocation. Engage on Notes, be positive while also being honest about your writing struggles.
Jodi: Write for yourself. Here and anywhere. I've published and written for money and I'm in a luxury place where I don't want to or have to listen to anyone and I can write and talk about what I want to write and talk about. That's what's made me happy.
Lisa: Honestly, my best advice is just WRITE. Write for yourself, be open to connections, play with the design of your newsletter - but first and foremost, you have to just write. (Note to self.)
What do you love about midlife? What’s hard?
Amanda: The best part about this part of life is saying no. If I know something is going to make me uncomfortable — like a party in a small space where I don't know anyone else — I know enough about myself that I should just decline the invitation. The biggest challenge is not offending anyone with my decision to take time for myself.
Karen: I love that my children are adults and I have more freedom to live my dreams and rediscover my new authentic self. The biggest challenge is that my son's still need support as Autistic Adults. Maintaining a 30 plus year marriage while also being a caregiver for our parents is also a huge challenge.
Jodi: Oh god, I love not thinking with my c*** anymore, now that I'm beyond menopause. I love not giving a shit. I love knowing what the small stuff is, learning to swim and get myself in the best shape of my life. Not letting anyone shame me for anything. Knowing what I want. Challenges? Teenagers. physically aging (my knees, please!), losing friends from natural causes.
Erica: I love feeling like I've come into my own. I actually feel comfortable in my body now. I feel confident and like I don't need to prove things anymore, don't need to jump through hoops I don't actually care about for the sake of some other goal. I can be at the place I want to be. The challenges are only just starting to unfold: aging parents, menopause on the horizon, etc. We'll get there.
Lisa: Midlife has been a really tough time for me in a lot of ways. Peri/meno was a big fucking nightmare (I've written a lot about it); the aging elders and struggling young adult kids have been A LOT. But there is a shift in confidence and creativity, and it's good to watch the youngsters start to blossom. I started really writing in midlife and it's saved me. I'm figuring out my body, finally, in ways that would have helped decades ago - but, better late than never. It's definitely a mixed bag.
List another Substack publication you love.
Amanda: Jenna Park's Everything is Liminal for astute observations about finding new chapters in life and coping with the challenges of living in my home town (NYC).
Karen: Raising Myles by Marc Typo
Jodi: Can I Do It Alone? speaks to me about aging, alone and all that that encompasses, about being a citizen of the world
Erica: Culture Study by Anne Helen Peterson about a variety of cultural issues by someone who sounds a lot like me.
Lisa: This is impossible. there are too many good ones! I love Elissa Altman's Poor Man's Feast for the fab writing.
Want to read more from these writers? Check out these posts:
Be sure to check out the full Midstack directory of Substack publications written by midlife women and submit your own Substack.
My favorite takeaway is that these writers feel good about themselves and what they do and create.
Thank you Jessica. I love how different everyone's process is.