Going Paid: How Courtney Martin launched and grew The Examined Family

We invited Courtney Martin, author of the examined family, to share her insights on launching a paid newsletter. Courtney's writing is about living humbly, lovingly, and bravely in a broken world. Her newsletter is a twist on Plato’s concept of “the examined life,” of a life worth living.

This transcript has been lightly edited for readability. You can watch the full interview in the video below.

Takeaways

  • Embrace the freedom to write whatever you want. If you write your own newsletter, you no longer have to pitch to other publications to accept your work. This gives you an exceptional amount of freedom to explore a variety of topics.

  • Get comfortable with getting paid. Your readers will support you if they love your work. If you put yourself in the mindset of a consumer, supporting artists that you love, remember that’s who you are for your readers.

  • Get creative with how you bring your community together. Courtney hosts bi-monthly Q&As where she features activists, organizers, or nonprofit directors, and then donates to their organization of choice using her subscription revenue. 

  • Ask readers for their input. If you’re feeling unsure about a piece you’re writing, try asking friends for feedback. If you’re making a decision about your newsletter, ask your readers for their thoughts with a discussion thread.

  • Show up for your community. If you want your newsletter to feel like a community, be active and involved. Respond to comments and take notice of readers who keep coming back. 


Why I started a newsletter

I had a weekly column at the On Being Project, which is mostly known as a podcast but actually has a pretty robust website as well. I'd done that for years and had built up this really wonderful audience there. Then, On Being decided not to have any columnists anymore, and I was trying to think of how to transfer this wonderful group of readers somewhere else. 

I'd always been a little reluctant about a newsletter, just because it sounded like a lot of work. I was kind of like, “Can I keep up with it? I have two small children and all of these things going on.” But I thought, “Okay, I'll just take the leap and do it.” At first I did it on Mailchimp, and it was fine. I found the backend deeply confusing, but I just stayed in my one little piece of it and tried to ignore the rest.

I had a pretty good experience, but then when Substack was created, I started to find some of the people I'm most interested in writing there. I was like, “This feels intuitively so much more how I think about the world, and also technically designed for someone like me.” I actually have worked on the backend of websites, my early blogging days, but it wasn't something I had the bandwidth to do at this point. I needed something really straightforward, with human-centered design, that would just let me do my thing.

The first transition to just having an unpaid subscriber crew was very fluid. It felt so easy to switch over, which I was shocked about. I was gearing up for all the technical disasters that always seem to happen and it was just, my list went straight from Mailchimp into Substack, and that was that, and I always found the backend profoundly easy to use.

From just a bandwidth issue, the biggest pain of freelancing has always been the pitching. I've never worked on a staff, I've always been a freelancer, and I've spent probably years of my life pitching into email black holes where no one gets back to me and I think I have this great idea. And so taking the pitching out of writing for me is just such a gift.

The other thing is some of those pitches are probably good, but there are also a lot of things I just could never pitch that I write about at Substack. Like this week, I had this thought where I was like, “Everyone's really sad, but we've been called to be so creative for these eight months of sheltering in. We keep trying to reinvent everything, like ‘reinvent the baby shower.’ And it's just like, I'm tired of reinventing things. I'm just sad, and everyone else is sad, and I'm just going to tell people that.” That's something that you would never pitch to an editor. You'd never be like, "I have this novel idea about the fact that everyone's sad and tired of being creative." They'd be like, "…what?”

With Substack, I can just write that weird little idea in 45 minutes, add some pictures from my iPhone and 10,000 people read it.

But with Substack, I can just write that weird little idea in 45 minutes, add some pictures from my iPhone and 10,000 people read it. And a lot of those people are paying me to have that weird, strange thought, and getting it on the page. So for me, it's just this incredible way to live my medium. I just pay attention to my life and write things. Sometimes I do things that are more elaborate. I do these Q&As with people that require a little bit more labor, but a lot of it for me is just a very organic, rewarding experience of observing the world around me, writing it down and seeing what resonates with people.

Why I decided to add paid subscriptions

I wrote free posts for a really long time before launching paid subscriptions. I didn't really know if I was ready. I feel like I just hit a moment.

It was more of an intuitive thing. It was like, “I've been doing this for a while, people seem to really be appreciating it.” I know I really like to support writers and artists and musicians that's doing something that feeds me, and I was just getting such profoundly gracious feedback from people. I'm not someone who's particularly comfortable asking for people for money, so I did have a psychic block of like, "Am I really going to ask people to pay for this thing that I've been doing for free?"

But I felt like: I believe in people getting paid for their labor, and as joyful as the labor is for me, it is labor, and I have a crazy life. Like I said, two small kids. Literally, during sheltering, I had been writing in a 1975 VW bus parked in my driveway because it's the only place where they'll leave me alone. But I just felt like I should be paid. This is, on some level, a feminist issue of just, I need to be paid for my work. I believe in asking for help and support when you need it, and giving help and support when you can. And so it just felt congruent, it just sort of felt right.

I was totally amazed at the response. I did the monthly option or the yearly option, and the option to be a “super subscriber,” paying, in my case, a hundred bucks. And I was just so amazed at how many people were automatically like, "I'll pay a hundred bucks," I'm so flattered.

You know, money is just one currency. Obviously I'm much more invested in love and discussion and changing hearts and minds and all these other things that I think of as metrics of my work, but it would be naive to say that it didn't feel amazing to be like, "Oh, people actually consider this worth paying for, and this supports me to do the kind of thinking that helps me write this kind of stuff."

It actually grew my audience to ask for money, because it made people realize, "Oh yeah, this is labor that she puts into this."

The other thing that I got a lot of was people buying subscriptions for friends, which is so moving to me. It actually grew my audience to ask for money, because it made people realize, "Oh yeah, this is labor that she puts into this.” I mean, the real hallmark of amazing writing, and something I aspire to, is writing that feels effortless because it's so organic and beautiful, and it lands in your inbox and you're just like, "Oh my gosh, that's what I was thinking. How did you put this into words?"

I'm so honored that that is the kind of feedback I get when I get it right. It's a double-edged sword because then it makes people feel like it's hardly labor, because the whole point of it is to make it not look super laborious.

So there's something about asking for the money that I think reminds people, “Oh, this isn't that easy. Every week, this woman figures out how to say something to me. It may not resonate every week, but let's say the majority of times, it feeds me in some way.” And then giving subscriptions to friends, I did the thing that a lot of folks do, which is to say, “If you can't afford a subscription, please let me know.” A few people did that and I was just overjoyed to be like, "Of course I'll give you a free subscription."

I think one other thing I was worried about when asking for paid subscriptions is that now this is a real duty and responsibility. If people are paying me, I feel like I really need to show up and produce quality content, and so that made me a little worried. I can imagine other people being worried. It's a contract of a certain type, right? Whereas when it's unpaid, you feel like you have a little more flexibility to be flaky.

But ultimately that was okay with me. I have a pretty regulated life and I'm a pretty prolific writer, so I was like, "I'm going to show up for people. I don't think this is a big problem."

The other thing I did that has really energized me are these Q&As that I run twice a month. It's on a Friday, and I just ask someone really cool five questions – usually activists or organizers or nonprofit directors. And then I make donations to their organization of choice using the subscription revenue that I have.

I say to my subscribers, we together are donating to this person, and please, feel free to donate even more to this person, but just so you know, your subscription, a percentage of that goes to these organizations. So that's been cool.

How I decided what to make free vs. paid

I do three things. I do a essay on Wednesday mornings that can be as random as like, “People are sad and they're allowed to be,” to more developed things like right after the election. Sometimes I go political. Most of the time, it's a mix of personal and political. Those essays come out Wednesday mornings, and that's unpaid, that's to everybody.

And then Fridays, twice a month, I do these Q&As that I just mentioned. That's paid, although there've been times when I've been like, "I really want everyone that subscribes to me to know about this person so I'm going to send it to everyone."

One of the nice things about Substack is that it's at your discretion, so it's not like you have to ask for permission to do that. If there's something that's in the paid content bucket, but you decide it’s too important, you're the boss.

On Sundays, I do this weird thing where I do Insta Stories of the New York Times, and then I take five of those Insta Story snapshots and load them up into Substack and send the thing on Sundays. So basically, like a New York Times Sunday digest, but the quirkiest kind you can imagine. I don't aim to be like, these are these stories. You have to know – it's more like, “This is the artist I want to have a whiskey with this week from the art section.” So that goes to paid subscribers as well, although my Instagram people could, if they wanted, access some of that content.

Getting comfortable with asking for money

I really love the idea of building community. Community is like my religion, and so I watched how other people were doing that on Substack, and that just really resonated with me.

I do have a fairly active audience, commenting audience, but nothing compared to some people. But I do feel like this is kind of a crew. They're a bunch of people who will comment every single week, and I've never met them. They're perfect strangers, but I feel like, "Oh, here's Vicky. Vicky's a grandma somewhere," because she's always talking about being a grandma, and so I do feel the sense of, we're a crew of people who, somehow, the place where we all meet is my voice and my sensibility and what I'm putting out in the world in these newsletters.

And so I do really like the idea of thinking about it as a community with some kind of shared sensibility, whatever we call that. My newsletter is obviously called the examined family, so I'm thinking about how do we really live an examined life? But in my case, I read a lot about my kids and parenting and power and race and that kind of stuff.

As an appreciator of art and writing and music, I thought: how do I feel about the stuff I subscribe to or pay for? And it's a joy for me to pay for things that feed my life and feed me, and of course I want to pay those people.

I did think a lot about my paid launch, just as myself as an appreciator of art and writing and music and thought: how do I feel about the stuff I subscribe to or pay for? And it's a joy for me to pay for things that feed my life and feed me, and I care about music I like to dance to, and art I appreciate, and of course I want to pay those people. It's such a wonderful gift that they gave me. So I would try to get myself in that mindset rather than thinking of it as super capitalistic, like I'm ‘monetizing’ my readers, which on some level, you could say, but I meant it. It was authentic that I felt like it was a way of saying, I get something out of paying for the art I love and I hope you do too.

If so, awesome. If you can't afford it, then let me know – I don't want money to be a barrier to entry to anyone to be reading me or a part of the conversation. And so it just felt right in that regard.

But I really worked hard on that. As much as I don't even remember what my actual announcement says, I did work really hard on it and I showed it to a bunch of people, because it is a hard thing to do, especially for individual writers who are used to someone else, a literary agent or a editor, a publisher or someone else who's in the business of it, it can, I think, feel a little bit weird to be the one to do it.

I asked people who are quite different from one another, like somebody who's a fundraiser in my life, [versus] someone who's kind of a socialist artist, who's like, "Screw money," you know? Because I wanted to be like, "What do a range of people in my life hear or see when they experience this message?"

I think that’s [helpful], because then you just feel like, okay, you've gotten a sense, before you hit send and worry about going public with it, you've had a little bit of practice tweaking it and responding to people's thoughts.

Reflections on my launch experience

A question I'm still holding is if giving people paid and unpaid [posts] makes sense. I'm really not sure. Part of me is like, “Maybe I should just make it all go to everybody,” and it's just more of a gift economy thing. Where if you want to support me, then you pay for this whole set of things that other people get for free, and you're fine with that because you like the idea of paying for the labor that goes behind the work I do. I've had moments where I'm like, "Why do I just send the Sunday thing to paid subscribers? I could just as well send it to everybody." But I haven't done so.

I think one of the things I've been surprised by, or I guess confused by, is how much content people actually want. [My friend] Fiona and I had lots of conversations where I'd be like, "People really cannot possibly want to hear from me multiple times a week." And she's like, "I think they do." I was like, "Really?" I would be so annoyed by certain voices in my inbox multiple times a month, but then it's like, well then you don't subscribe to them. So I think that's a thing I'm still feeling out too: how much of my voice and sensibility do my subscribers actually want?

I saw that Cheryl Strayed had started a Substack thing and she was doing, I think four times a year. It’s very infrequent, and I was like, "Oh, that's fascinating." You know, she's Cheryl Strayed obviously, but I like writing pretty frequently. That is a question I'm holding, of, isn't that interesting that people seem to want more frequent contact than I would've guessed. And then, as the writer of that, how do you gauge how that’s feeling for [your readers]? So I may, at some point soon, do a survey of some kind, where I just say, "Hey, this is a community thread. What's working, what's not? How much content do you want?"

The other thing I've been thinking about doing, and I haven't decided exactly how yet, but this is the first year that I’ve had paid subscribers, and I was like, "I really want to thank everybody." And I don't have enough subscribers to make that truly crazy.

It will be a big labor, but I've been thinking, maybe I'll send everybody just one individual, really short email, but a customized email where I say just something. Like for the Vickys of the world – the people who are true strangers – I'd be like, "Hope grandma life is going well," so she knows that I actually do pay attention to these comments.

That's another thing, I feel a real duty to be in the comments section and like people's comments and respond to them, because I just feel like that means so much to me, when I feel like people actually pay attention to comments. I think if we're going to ask for people to pay money and say it's a community, we have to show up like that.

Advice for writers thinking about launching paid subscriptions

I think I would just say, put yourself in the mindset and the heart space of yourself as a consumer and an audience of art that you love, of books that you love, of content that you love, and try to remember that that's who you are for the people who will choose to subscribe.

I mean, it's sort of a depressing way to be, but my way of approaching my work is always, have real low expectations. Whenever I write a book, I'm always like, if one person finds this useful, I'm going to find it useful. I write books, I need to read, so there's no question, I'm going to find this useful, but if one other person emails me and is like, "This really helped me," that's worth it for me.

The nice thing about having expectations that low, is it doesn't become a big ego thing. For me, it was like, if anybody feels like subscribing paid, that will be such a wonderful surprise and honor to me. And then when hundreds do and thousands do, then you're just like, "What an incredible gift."

So for me, to emotionally survive it, I just don't get really involved in having a huge, ambitious number. Maybe that is not smart and strategic. I would be happy to entertain it, that's part of why I don't have a million followers or something, but I just want to connect with the people who authentically connect with my work, and be very grateful that they're up for paying for it, and that I get to do this work at all, which just feels like a miracle to me.

I just want to connect with the people who authentically connect with my work, and be very grateful that they're up for paying for it, and that I get to do this work at all.

I didn't come from a family of artists or writers, so I can't believe I pay my mortgage with this kind of work. So yeah, I think just to be authentically grateful, and aiming to be useful, but not getting your ego involved in it or depending on it.

As your audience grows over time, obviously you can integrate it into your life and how you think about what you need to live on and pay for and that kind of thing, but starting out with low stakes [is helpful]. Start it before you are desperately in need of the money, so that you can be grateful – if you have that option, I know some people don't – but so they can just build it and not feel crushed if it doesn't meet particular metrics or something. I think just trying to be as organic and in a space of graciousness as possible is the way to go.