Have you created a strategy for your newsletter?
A newsletter is the best way to communicate directly to your readers without relying on Twitter to surface your posts or Google to rank your articles. When you have a newsletter, you don't have to worry about crazy algorithm changes or something happening to posts that you've optimized for search.
I've started several newsletters over the years. Of course, my biggest newsletter is the Become a Writer Today Email List. I'd love it if you could join it. I'll give you a free book of writing prompts if you do. Sign up here.
Once a week, I send weekly updates about the latest writing articles and also writing advice to members of this newsletter. Now that's my strategy; your strategy may differ.
This week I caught up with an expert in newsletter strategy. Her name is Anna Codrea-Rado. She ran one of the most successful Substack newsletters. It's called The Professional Freelancer, which Anna has recently rebranded.
When she's not writing newsletters, Anna advocates for freelance writers in an increasingly challenging industry. She also helps businesses figure out what their newsletter strategy should look like.
I was excited to catch up with Anna because I love hearing about how different creatives and writers use newsletters to communicate directly with their readers.
Anna says, "You need to have a really clear tagline for your newsletter, you need to be really clear on what the problem your newsletter is solving." "Random stuff is not going to cut it."
In this episode, we discuss:
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Anna: You need to have a really clear tagline for your newsletter, you need to be really clear on what the problem your newsletter is solving for your readers and I tend to say just writing random stuff is not going to cut it.
Welcome to the Become a Writer Today Podcast with Bryan Collins. Here, you’ll find practical advice and interviews for all kinds of writers.
Bryan: Have you created a strategy for your newsletter? Hi, there. My name is Bryan Collins, welcome to the Become a Writer Today podcast. Every writer should have a newsletter. It’s the single best way to communicate directly to your readers without relying on Twitter to surface your posts or without relying on Google to rank your articles. When you have a newsletter, you don’t have to worry about crazy algorithm changes or something happening to posts that you’ve optimized for search. Just look or ask any business who had a page on Facebook years ago. Now, it’s all but impossible to rank on Facebook unless you’re prepared to pay for advertising.
I’ve started several newsletters over the years, some of them for content websites, some of them for different business projects, and some for my own writing. Of course, my biggest newsletter is the Become a Writer Today Email List. I’d love if you could join it. I’ll give you a free book of writing prompts if you do. Once a week, I send weekly updates about the latest writing articles and also writing advice to members of this newsletter. Now that’s my strategy, your strategy may differ.
This week I caught up with an expert in newsletter strategy. Her name is Anna Codrea-Rado. She ran one of the most successful Substack newsletters, it’s called The Professional Freelancer which Anna has recently rebranded. When she’s not writing newsletters, Anna is also an advocate for freelance writers working within an increasingly challenging industry and she also helps B2B or business companies figure out what their newsletter strategy should look like. I was excited to catch up with Anna because I love hearing about how different creatives and writers use newsletters to communicate directly with their readers. One of my key takeaways from talking to Anna is the differences between having a newsletter for a personal or a creative project versus having one for your business. Anna also talks about how often you should send newsletters to readers, what you should include, and how her newsletter strategy has evolved over time, and she also articulates why she believes newsletters are a better tool for writers than social media.
Now, Anna built her newsletter on Substack. Substack is a fantastic platform for writers. There are alternatives. You can also use ConvertKit, which I use for the Become a Writer Today Email List. It’s relatively affordable, easy to use, and helps me create various automations and rules so people get the right articles and posts based on their interests. I realize that can be a little bit advanced so other tools that you may want to check out include MailChimp. I did start with MailChimp back in the day but I moved on when I outgrew it and also when they changed their pricing structure. Ghost is another alternative to Substack and I’ve used Ghost in the past and found it quite good to use too. But like anything, the tool is less important than actually having a good strategy that you’re going to follow. In other words, write and publish helpful content for your ideal audience. Pick a publishing cadence that works for you and build a relationship with your ideal readers through your best content and writing. That could be on Substack or it could be elsewhere.
Now, let’s go over to this week’s interview with Anna and, of course, if you do enjoy the interview, I would really appreciate it if you could take the time to leave a short review on iTunes because when you leave a short review, it helps the Become a Writer Today podcast grow and it helps more writers find the show. And, of course, if you do enjoy it, please share this show with another writer who’s interested in starting their newsletter.
Bryan: Welcome to the show, Anna.
Anna: Hi, thanks so much for having me.
Bryan: It’s really nice to talk to you. I worked as a freelance writer for a number of years. I found it quite difficult to work as a freelance writer, hard to earn a living, I imagine it’s harder today, so I wanted to ask you all about your take on the industry, but before we get into freelance writing and newsletter businesses, how did you start your writing journey?
Anna: I have actually been writing for as long as I can remember. I have a memory of writing short stories in my grandparents’ back room when I was there on some holiday as a kid, but as a professional, I actually started at university in my undergraduate so I was studying at Durham University, I was doing English literature, and I read this piece in the locals — well, not the local paper, in the student paper, and ended up writing a comment piece in response to it, had that published, and I still remember to this day, I’m still friends with this person, they said, “Wow, you’re really good at writing, this could be a career,” and that just stuck in my head and it was sort of my first experience of using writing in a, I mean, it wasn’t that professional, you don’t get paid as a student journalist, but it opened my eyes to this world of journalism and that there’s a way to make writing part of your career. So that’s kind of how I first started writing. And throughout university, I did actually start freelancing. I wrote for the student paper but then I also freelanced for some local publications as well doing music reviews and interviews with musicians, which is actually quite amazing as a student because you get to interview all sorts of celebrities when you have absolutely no idea what you’re doing. And then, yeah, at some point in university, I kind of decided, “Okay, I’m going to try and become a journalist, that will be what I wanna do with my career,” and that’s how I started and went on to get a job in editing an alumni magazine for a different university and then went and worked at various media organizations and then went freelance about five years ago.
Bryan: Similar to how I got started writing, writing for a school newspaper and then I took a journalism degree. My dream was always to work as a columnist for a national newspaper in Ireland, which didn’t happen. Probably a good thing. Did you always want to freelance or was it just the way work evolved for you after graduation and when you started your career?
Anna: Both. So I wanted to freelance I think as a result of my frustrations working in office environments. I just fundamentally don’t think that I’m built for working in an office, but I was too scared to do it because I had no idea the mechanics of it, it all seemed very amorphous, very scary, and I actually went freelance because I got made redundant so I wanted to do it but I was too scared to do it and then I was eventually pushed into it.
Bryan: A lot of freelancers don’t know what niche or genre, or niche, as you say in the United States, they should specialize in. Did you find that difficult?
Anna: I think this whole focus and discourse around, “You need to pick a niche, you need to pick a niche,” I think is actually really distracting and I have myself fallen into this trap. I think it can make people think that the only way to succeed is if you find this really specialist area and you really own it. Because I think I come to freelance writing from journalism, I was taught quite early on in my career by one of my journalism professors who’s now a mentor of mine that part of the whole appeal of being a journalist is getting to become an expert in lots of random and sometimes unrelated topics and that you can change your — journalists call it a beat, you can change your beat throughout your career and that was actually to me one of the appealing parts of this job. So I’ve had lots of different niches over the years. Currently, I really focus on work culture and work life, but I’ve written about electronic music, nightlife culture, language learning, health care, sustainable business. I’ve written about — so my niches and beats have really changed over the years and I imagine they will continue to change. I actually hope they continue to change. So I don’t get too hung up on that. And also, for me, it’s more important to focus on things like what format I like to write and what style of writing and what area of writing that I’m interested in. So, for example, I know that I can do it but I’m not a news reporter, I’m way more into feature writing and narrative nonfiction and that almost more like storytelling really. So that, to me, I think is what’s more important than specific subject areas.
Bryan: Yeah, that’s one of the appeal of being a journalist, you can ask interesting questions to people across different industries that you wouldn’t get to speak to normally. Now I find freelancing quite tough so probably wasn’t a very good freelancer in terms of looking for work each month. I’d often work on a single story, submit it, and then I’d have no more work lined up. Is it still a difficult profession today?
Anna: Yes, and I think it’s actually getting more difficult. I think — you’ve kind of articulated what the fundamental problem is is if you look at freelancers in other industries, so let’s just say tech, for example, and the tech industry where freelancers really are contractors. They’ll get one contract with a company over an X amount of period of time, it can be weeks, it can be months, and they know that they’ve got, let’s say, three months of paychecks coming in, they know that they’ve got this work in the pipeline. Journalists, freelance writers, it’s so much more piecemeal. It’s you’re pitching a story here, there, and everywhere for much smaller amounts of money and the stability is just really, really volatile. For me, I want to work on the stories I want to work on, that’s why I’m freelance, that’s why I don’t work in house, and so I look for other ways that I can bring in income and revenue streams in order to essentially finance my journalism and my story and my writing. I really don’t love that, that I have to do that. I think that that’s testament to how broken the media industry is. It’s just a really janky way of building a career. But at the same time, that is the situation we find ourselves in. I personally do a lot of campaigning work and I’m involved in all sorts of initiatives to try and change the industry but until we see that change, I have to work with what I have available to me. And so that’s how I set things up. And from a practical — like what that looks like practically is I do newsletter strategy for clients. That means I help them build and execute their own newsletters, whether they are internal or external facing. I do workshops for some companies. I go into companies and I talk about — I help them with their productivity stuff and kind of in terms of they might have like a wellbeing initiative that they’re working on and help with time management and productivity and stuff like that. I do speaking. So many things that I kind of do, not all at once, but, yeah, I’m kind of constantly sort of looking for efficient ways to build income streams so that I can focus on the writing that is important to me and the stories that I want to focus on.
Bryan: It’s interesting you mentioned traditional media. One of the platforms that you use, Substack, is aiming to change the way writers interact with their audiences. Was that what drew you to Substack in the first place?
Anna: So, my story with Substack, so I was actually very early. I knew the band before they were famous. I was actually a really adopter of Substack and it happened completely serendipitously. So I had already been writing a newsletter in MailChimp and had started it before Substack I think even existed, and then I got to 2,000 subscribers, which, at that time, MailChimp started charging their users, I think they still do this, but they were charging to use the platform and so I kind of thought, “Well, this makes no business sense for me to now be paying to send a newsletter,” and I was looking around for other options and I happened to meet somebody who had a newsletter on this thing called Substack and it was small enough at the time that he was in touch with the founder, one of the founders, Hamish McKenzie, and he connected me and Hamish personally convinced me to switch over to Substack and I did that and that was, I don’t know, two or three years ago now.
Bryan: Oh, he personally convinced you. He’s in the United States. Were you traveling in the United States?
Anna: No, we spoke over email. We just connected virtually. This was all before the pandemic. And then we did meet, so he was in London at some point, but I think I was already, I think I had already committed to him by that point, yeah. He’s a very good salesman. But, I mean, I think Substack is a really brilliant platform, I think, to me, especially right now with everything that’s going on with Twitter and Facebook and Meta and everything, it’s really important to be, — of course, I put my tech journalist hat on when I say this, but it’s really important to scrutinize the platforms. But one thing I will say is, to me, what marked Substack out from a lot of the other kind of platforms that we’re seeing is looking at their core mission and what drove them to set this product up and it was to fix a problem that actually is there, which is that writers are not getting paid. That’s a problem that writers are living and breathing and that’s the issue they’re trying to solve. We can discuss and debate whether or not it’s the right way to do it but the problem they are trying to address is very real and it’s one that really does need solving. I think that they’re going about it — I think they’ve got a product that definitely does a lot to solve this problem. I think it’s one piece of the ecosystem, which I’m pretty sure Substack would say themselves, they don’t think that newsletters is the only way, is the sort of the magic bullet to fix journalism but it’s definitely a step in the right direction. I sound like I’m a Substack shill, I’m not but I think it is a really good platform.
Bryan: It is a good platform. I’ve used it on and off over the years. I’ve also used some other platforms as well, including ConvertKit and Ghost, which are good too. So your newsletter is called The Professional Freelancer.
Anna: It was called that, it’s now called A-Mail. I’ve changed the name multiple times. Yeah, it’s now called A-Mail, as in, yeah.
Bryan: Are you still going to focus on the topic of freelance writing or freelancing?
Anna: So I put the newsletter on — well, I actually closed the newsletter and then recently I sent another one kind of out of the blue because it’s been about six months since I last posted and I really, really missed it. I’m truthfully not entirely sure in what format and how I will bring the newsletter back. I think the thing that I have realized in these last six months is I think it’s important to kind of go back to sort of how I started the newsletter and what I originally was doing with it, and I think it is really important, as I mentioned, it’s important to emphasize that I started a newsletter pre Substack and I started a newsletter because I was at a point in my career where I needed to regain a bit of control having faced a redundancy, I didn’t know exactly what I wanted to write about but I just wanted to write, and, to a large extent, I’m looking to kind of go back to that ethos of feeling like I’m emailing my friends. I started with about 50 friends on an email list and that has now grown to 15,000. Pre-pandemic, I had monetized the newsletter, it was a really successful business that was focused around giving freelance advice. I also hosted in-person events for freelancers who were paying subscribers of the newsletter. Then the pandemic just turned all of that on its head and I think also there are now so many other people and so many other initiatives that offer something really similar so I think I’m going to leave that sort of advice giving, maybe close that chapter, not to mention I’ve written a whole book about how to freelance so it’s not that I’ve run out of things to say but I think I’m looking to see what possible new direction I could go in. I’m not entirely sure what that is going to be but what was really interesting is when I did send this newsletter recently, what I really heard from readers, and they’ve been reading me now for five years, they kind of said, “It’s not even so much what you write about, we wanna be hearing from you,” so I’m trying to figure out what that’s going to look like. It’s that sort of double-edged sword of it’s amazing to have the freedom to write what you want to write but then, at the same time, I am conscious that when I go in and tell companies how to develop a really strong newsletter strategy, you need to have a really clear tagline for your newsletter, you need to be really clear on what the problem your newsletter is solving for your readers, and I tend to say just writing random stuff is not going to cut it, and I’m now not taking my own advice. But, yeah, so basically watch this space is the short answer.
Bryan: Yeah, I can imagine some of your old newsletters were quite labor intensive. One that came to mind is when you surveyed rates across the industry and compiled a report. Hadn’t seen anything like that elsewhere but I would imagine that took a long time to write and create.
Anna: Yeah, yeah, that took a lot of work. I mean, yeah, I see that stuff, as I mentioned, kind of — well, it’s part of, I guess, almost this campaigning work that I do and that data is still out there and is still available. NUJ, the National Union of Journalists, I’ve sort of got a bit of an open data policy so they asked me if they could use the data and I was more than happy for them to do a bit of analysis on it and they used it and that informed some of their campaigning work. But, yeah, all of that stuff, it is really labor intensive and it’s just always that balance of making sure that you’re doing the things you want to do, because I always come back to why am I freelance and what do I want to get out of this and, for me, a big part of that is the freedom and flexibility to work on my own terms and to get to work on projects that means something to me, but then the flipside is, of course, I also have to do work that pays the bills and if I find myself in a situation where I’m not going to do any of the work that I want to be doing and only working on projects that I’m either not enjoying or not being treated well by clients, I kind of think, “I could be just working in house at this point,” so it’s just always kind of keeping an eye on the balance in my freelance business. And, yeah, it’s a constant line that you have to toe.
Bryan: Makes sense. Makes sense. You mentioned you grew your newsletter to 15,000 subscribers. That can seem like a huge amount for somebody starting out. What tips would you offer new newsletter creators to achieve similar growth?
Anna: So I think it all starts with why you want to write a newsletter in the first place. Is it that you see it as effectively marketing strategy for your own business, whether that is wanting to build an audience because you are a freelance writer or maybe some other sort of business-led reason for it, or are you a budding writer who wants to practice writing and grow an audience and get feedback and almost use it as a playground for your creative ideas? All of these things are really important to keep in mind from the beginning. And then I do think there are some central tenets to good newsletter writing or newsletter strategy that you do need to adopt at the beginning. Once you have grown to 15,000 and you’ve been doing it for long enough, you then get into a position, which I am now fortunate enough to be in, which is that you can have a rethink about all of these things, but until you get there, for me, those central tenets are consistency, so that doesn’t have to mean every day, that doesn’t even have to mean every week, but you need to pick a day and time, it doesn’t really matter when, just one that is convenient for you, for your newsletter to go out so that people get in the rhythm and get used to hearing from you on a regular cadence. I also think that you need to be really clear on what problem is your newsletter solving for your readers. So them just hearing from you about your random thoughts is not going to get them to hand over something as precious as that email address to you, so being really clear on what they’re going to get out of it if they sign up for your newsletter, though to give an example, there’s a really good newsletter that’s written by a technologist, I think, they’re quite senior at a technology company. But, anyway, the newsletter is called Technically and its tagline is helping people understand software and technology to make you seem smarter in front of your boss so it’s really about helping people who find themselves in a very tech heavy world, particularly at work, and helping them understand things like an API and open source and all of these things and it’s just very clear what that problem that they are trying to solve is, what the readers’ problem that they’re trying to solve is, so being really clear on that, doing it consistently, talk about it as much as you possibly can. No one knows how much work you’re doing, you are the only person who knows how much work you are doing and you might feel like you’re talking about something constantly but if you think about how many emails you’re getting every day or how much information is coming to you every day, it’s so easy to forget, like, “Oh, Anna’s got a newsletter,” it might take them — I have friends in real life who, I’ve been writing this newsletter for five years and they still, it just passed them by. So you have to always be selling it and talking about it and getting comfortable with that. And buckle in for it to be a really long slog. There is no — I know that we live in the age of TikTok and YouTube courses and all of this stuff with people promising your first 1,000 signups in the next 30 days and all of these things. These are by and large vanity metrics and real engagement and real newsletter community takes a long time to build and it’s something that — it will become easier as you get better at writing newsletters, but you have to be prepared for this commitment and don’t get disheartened if you don’t hit even a 100 subscribers within your first couple of weeks. It will take a while.
Bryan: Some newsletter owners say a lot of subscribers comes from Twitter. Is that something that you found?
Anna: I think I bucked the trend on this somehow but I have always had more newsletter subscribers than I have had Twitter followers so I’m not someone who has a — I didn’t start out with a massive Twitter audience which I then converted to newsletter subscribers, not to mention that any Twitter audience that I had before I started my newsletter actually wasn’t the audience that eventually became my newsletter audience because I was writing about quite different things when I was sort of building that Twitter audience. I definitely do find that something like Substack, it’s a much more shareable platform so I’ve definitely noticed — I noticed pretty much immediately after I switched from MailChimp to Substack that I was getting a lot more subscribers coming through social media platforms in general. I think Twitter definitely has always historically been one of them, just because it tends to be a place that writers congregate and also people who like to read things also congregate but I definitely would say don’t be put off by thinking, “Oh, I don’t have a big Twitter following,” not to mention also who knows what’s even going to happen with Twitter. I know lots of writers, myself included, they’ve kind of either abandoned the platform or they’re just spending less time on it. There are other ways to build audiences. For me, the biggest surge in newsletter subscribers has always been when other newsletter writers recommend my newsletter or when I have given talks, particularly virtual talks, on a topic that’s really closely related to my newsletter and someone has put a link into the whatever the Slack group or the Zoom meeting. Those kinds of things are the things that have gained me the most followers quickly so I wouldn’t worry too much about Twitter.
Bryan: Substack has also made it easier for people to subscribe within the app. I’ve noticed an increase in subscriptions that way.
Anna: Yeah, exactly. And I’ve really noticed that it now has a recommend feature so other newsletter writers can recommend each other. I’ve noticed both ways. I’ve noticed from the number of people subscribing to my newsletter when other people recommend me but also I recommend a newsletter and I have spoken to that newsletter writer and that has given them a really big volume of subscribers as well so it’s that recommendation thing that’s such a big driver. Quite simply people forwarding the newsletter. A really simple thing that every newsletter writer should be doing is putting in their newsletter quite big, something that encourages people to forward their newsletter. What I like to do is try to personalize it so if I’ve written that week about, I don’t know, plants, I wouldn’t write about plants, but I would say, “If you know a plant lover who would like this newsletter, forward it to them,” so just slightly tweak that sentence every week rather than just say, “Forward this email.” That really helps because, yeah, I mean, one thing that I know that was happening with my newsletter when I was really writing a lot about freelancing was every time someone went freelance, their friend would forward them my newsletter and say, “Oh, hey, you’ve gone freelance. You should sign up for this,” and position your newsletter to be whatever equivalent that is.
Bryan: Did you find a book you wrote about freelancing difficult or more challenging or even different to writing newsletters regularly?
Anna: My ability to write my newsletter on a schedule definitely comes from my journalism background of having to work on deadlines and that really helped with the book as well because, yeah, sitting down to write 70,000 words is incredibly daunting task but I broke it down into chapters and then, within those chapters, I broke those down into sections. So wrote it in lockdown. I found the writing process actually quite enjoyable. It really gave me something to do, it gave me something to really dive into and focus on, and I didn’t — because also, one thing I will say is that it’s a nonfiction book, I didn’t have to, of course, there’s an overarching theme, which is how to build a successful freelance business or solo or business of one, but I wasn’t dealing, it’s not fiction, I wasn’t dealing with characters and an overarching story arc and all of these kinds of things. So I didn’t find it difficult to write, I think what I found challenging was more the publishing side of things, what happens when the book comes out and then trying to, you know, the selling of the book and all of these things, which, again, were very much affected by or marred by the pandemic. I didn’t get to have a book launch and all of these things, bookshops weren’t open when my book came out so I didn’t get to do that thing where you go and see the book in the bookshop, I sat on Zoom. And so, yeah, I actually found the writing — and it really taught me a lesson in the difference between writing and publishing and how those two things are actually very different. Writing is something that is creative and, by and large, is a private process, whereas publishing is really public and is also commercial. So it was a really good lesson to learn, I think.
Bryan: I interviewed a Substack author a few months ago, she serialized her book on Substack as well as self-publishing. Seems to be a popular trend these days.
Anna: Is that The Novelleist?
Bryan: That’s the one, yeah. Is that something you’ve considered?
Anna: I definitely have thought — when I was selling my book and thinking about writing my book, it did cross my mind that I could just continue doing it as a newsletter and that would have very much been an option. I mean, I think, to be frank, I mean, I don’t know this for sure, I reckon I would have made more money had I rather than done a book, done it as a newsletter. However, there is still, for all of the new media platforms and new directions that digital media is going in, there is still this element of prestige that comes with the traditional publishing houses and certain publications. And my book was published by one of Penguin Random House’s imprints and that really does carry a certain prestige and that is important for one’s profile. I definitely have noticed that that is something that people have cared about, more so within industry rather than necessarily consumers, but that’s just something to think about. Kind of comes down to what are you hoping to achieve, why you write this book, if this is just purely about money, or not purely, I don’t mean purely about money but if you want to put your commercial hat on and think about it as a business venture, then something like a newsletter probably will make more sense. If you’re thinking of it as this is almost an act of profile building and adding that badge of prestige so that I can, for example, go and pitch myself as a speaker or go into companies and all of these things, having a book and having it published by one of the big publishing houses is something that’s going to be more valuable. So it is difficult. It’s something that, I don’t know, I’m definitely open to experimenting with. I mean, there are lots of now famous authors on Substack serializing their work. Salman Rushdie was writing on Substack and serializing something and I think Margaret Atwood might be on there now as well. So it’s definitely something that I’m open to experimenting with, but I’m still at a stage in my career where it is also really important to make those strategic decisions as well.
Bryan: Makes sense. So, Anna, where can people go if they want to read your newsletter or your work?
Anna: The best place to find me is probably, yeah, to sign up for my newsletter. If I bring it back, I will bring it back at some point. It’s my name annacodrearado.substack.com. I’m the only Anna Codrea-Rado in the world so if you can get the spelling right, then you’ll find me.
Bryan: I’ll put the spelling in the show notes. Thanks for your time, Anna.
Anna: Thank you so much.
Bryan: I hope you enjoyed this week’s episode. If you did, please consider leaving a short review on the iTunes Store or sharing the show on Spotify, Stitcher, or wherever you’re listening. More reviews, more ratings, and more shares will help more people find the Become a Writer Today Podcast. And did you know, for just a couple of dollars a month, you could become a Patreon for the show? Visit patreon.com/becomeawritertoday or look for the Support button in the show notes. Your support will help me record, produce, and publish more episodes each month. And if you become a Patreon, I’ll give you my writing books and discounts on writing software and on my writing courses.