How to Launch and Grow a Successful Freelance Writing Career With Jessica Lawlor

Successful Freelance Writing Career

Do you have a desire to become a freelance writer? 

Are you already a freelance writer and want to take your career to the next level?

Then this podcast is for you.

Jessica Lawlor is the editor of The Write Life and on Monday, September 14th, they launch The Writer’s Bundle, a package of courses designed to accelerate your freelance career. 

It provides valuable information for freelancers, including how much to charge, how to find clients, and so much more.

I got together with Jessica to discuss the bundle, which I’ve contributed to, and to talk about how she manages a busy website like The Write Life.

In this episode I talk to Jessica about:

  • The Write Life bundle
  • Opportunities for freelance writers
  • How she manages the workflow for a busy website
  • How she drives traffic to her site
  • The type of content she enjoys writing 


The Writers Bundle 2020
The Write Life
Jessica Lawlor Newsletter

Jessica: I'm really looking for someone who understands our site and understands the type of content that we publish, and this is probably advice that writers have heard over and over again, but do your homework, research the site, and read the site, be a fan of the site. I think people who are fans of the sites or the outlets that they're pitching have much better success at getting published than someone who comes across the site and thinks that might be a great opportunity for them.

Introduction: 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: Would you like become a freelance writer? Or perhaps you already are a freelance writer, but you want to take your career and your income to the next level? Hi there, my name is Bryan Colins and welcome to Become a Writer Today podcast. I've worked as a freelance writer on and off for the last 10 or 15 years. I've written for publications in Ireland and national newspapers, some websites about technology and so on, and all of this was before I started to Become a Writer Today. I've also written more recently for publications like Forbes, and I've done a little bit of freelance writing for publications on Medium too. I like freelance writing because it's a great way of figuring out what genre you want to write in. It's also a great way of supplementing your income if you have a day job. And it's also good if you want to build up a name for yourself or for your writing business.

Bryan: Of course, there are struggles that freelance writers will sometimes face. How much do they charge? Where can they find clients? And how can they manage all of the different clients, because sometimes when you are a freelance writer it can feel like a feast or a famine. But if you're struggling with anything like that, I was recently invited to join The Write Life 2020 bundle. It's a bundle for freelance writers which is launching on Monday, September 14th, and I'll put a link to it in the show notes, but you can find it at Now I recently had the chance to catch up with the editor of The Write Life to ask Jessica Lawlor about the bundle and also I wanted to ask her about her career as an editor, because The Write Life is one of the biggest writing sites online for freelance writers, and they publish a lot of articles and work from other freelance writers and from third parties.

Bryan: And it was really interesting to hear how Jessica manages such a busy website. But of course, I started by asking Jessica how she got into editing and how she started editing The Write Life in the first place. But before we go to this week's interview, if you enjoy the Become a Writer Today podcast, please could you leave a short review on the iTunes store, because more reviews are more ratings will help more people find the podcast. And if you're interested in joining or buying the bundle from The Write Life, but you've got questions, just send me an email. Bryan, B-R-Y-A-N, and I'll answer your questions about what's in the bundle. Now with that said, let's go over to this week's interview with Jessica and her answer to how she became the editor for The Write Life.

Jessica: Absolutely. And thanks for having me Bryan. This is really exciting to be on your show today. So I started working with The Write Life about four years ago now, and I had been a fan of the site. It's been around for, I should probably know this information, but it was definitely around for at least three or so years prior to me joining as the editor, it's probably seven or eight years. I had been a fan of the site. I've been a fan of Alexis Grant, who's the founder of The Write Life, for many years. I've been following her work online. I became friends with her initially through Twitter and just seeing the different work that she did.

Jessica: She actually invited me to become a writer for The Write Life, so I started out as a writer and I worked with the person who was the editor at the time, and I pitched ideas, and I had my work published on there. And then in 2016, Lexi, her name's Alexis Grant, we call her Lexi, she was looking for a new managing editor, and at the time I had just quit my full time job in public relations to start my own business and this seemed like a perfect opportunity. So I applied for it and I was lucky enough to get the job.

Bryan: That's fantastic. So The Write Life has pretty stringent editorial guidelines, I would say, for people who want to write for it. So I suppose if a writer was looking at The Write Life and they thought that would be a way for them to build their portfolio as a freelance writer, what would you say to them? What does an editor like you expect from a freelance writer when they're pitching?

Jessica: I'm really looking for someone who understands our site and understands the type of content that we publish. This is probably advice that writers have heard over and over again, but do your homework, research the site, and read the site, be a fan of the site. I think people who are fans of the sites or the outlets that they're pitching have much better success at getting published than someone who comes across the site and thinks that might be a great opportunity for them. So I would say do your homework, read the site, read the submission guidelines. That's something that's available on most sites, including The Write Life. And if it's hard for you to find that, I often just suggest Googling the site that you want to pitch and submission guidelines or contributor guidelines, and really paying attention to how an editor wants to be pitched, what they want included in that pitch, maybe even suggesting a headline or two.

Jessica: And I always like, I always tell writers, not just to include their post idea, but a couple of bullet points about what their posts might include and a little bit about why they are a person who could be an expert on that topic and actually write about that topic. So providing all that information up front in a pitch and personalizing it to the editor. So finding out who is the editor of the site. I love when people pitch me and they say, "Hi, Jessica," and they know a little bit about me or they know a little bit about the site because we're all looking for that connection, and I love to work with writers who I can be friendly with and who we can connect and we can talk about writing and talk about editing. So I think putting that little bit of a personal touch can really go a long way too.

Bryan: Do you think things have gotten harder or easier for freelance writers these days?

Jessica: Oh, that's such a good question. I think there's a lot of opportunity for freelance writers right now. I think things are harder. I mean, there's a lot of competition. There's a lot of people out there who want to write, a lot of people who are pitching, so there's a lot of competition, but I also think that there's so much opportunity and I think that there's a lot of room for writers and there's enough work to go around. So I think now is actually a really exciting time for people who want to become freelance writers, who want to grow their freelance writing career. People are always looking for content, and I think you just have to keep your eyes out on the places that you want to work with.

Bryan: Just to switch things around. How do you, as an editor, deal with all of the pitches that you get? Because I can imagine there's quite a lot and I can imagine there's probably some that aren't even relevant to The Write Life. It's probably just people doing basic email outreach. So how do you manage it all?

Jessica: Definitely. So in addition to The Write Life, I also manage a couple of other different blogs and sites. So I am fielding pitches on multiple fronts in multiple inboxes. And honestly, the way that I manage it is I look for those personal pitches first. So it's pretty easy for me to scan through an inbox, especially The Write Life inbox, where we often get a lot of unsolicited pitches, and I can easily see what might be something from a bot. We get a lot of pitches from bots now, it's really weird. So I can easily scan to just delete those and clear them out. I can also look to see who has sent an idea that really isn't relevant, isn't even about writing, and then delete those right away. And then from there really look for the ones that have clearly outlined their idea, who have provided a sample headline, who have left me a couple of bullet points, and just go from there and check out the ones that seem most relevant.

Bryan: And in terms of the workflow, when I manage the workflow for Become a Writer Today, I use either a Trello Kanban board or a spreadsheet. Is there a system that you have for keeping track of writing projects that are in progress, that are ready for publication, or at the pitch stage?

Jessica: Yeah, definitely. I absolutely love Trello. I think Trello is such an amazing tool. It's so nice to be able to visually see an idea go from a card that's just an idea through the different stages of editing, whether it's in editing with me as the editor, then back to the writer, back to me, putting it into the final touches of headlines and adding images. So I really love Trello for that. At The Write Life we also use a plugin through WordPress, it's just a very simple editorial calendar plugin where you can drag and drop different articles into different days. So that's really nice to just get a quick monthly view of what we have coming up. So I would say Trello, WordPress, and then I also tend to use just Google spreadsheets to keep track of who's writing what and the different payments and all of that to stay really organized.

Bryan: So on my side I've alternated with approaches to the cadence of publication. I've gone from one large post about a topic once a month, to one post once a week, to more recently maybe two to three posts a week. What do you find is the right publication schedule for The Write Life?

Jessica: That's such an interesting question, because it's changed so much over time. I think back to like three years ago, we were publishing every single day, and just thinking back to that, wow, we were putting out so much content. And now we've pulled back a little bit and we've gotten really focused on what it is that our mission is and finding the right keywords and making sure that we're spending a lot of time on a post and doing SEO research and really working our headlines. Something interesting that a lot of people don't know about The Write Life is that we actually write 10 to 15 different headlines for every single post that we publish to find the best one. So we really spend a lot of time prepping a post.

Jessica: So now we publish one to two posts per week. And something else that we do is we refresh old posts. So since our site has been around for so many years, we have so much content from a couple of years ago that's still pretty relevant and usually just needs a cleanup or an update to make sure that the links are all correct or that we still stand by the information that we shared. So typically once a week, we'll try to put out an original post, a new post, and then once a week, we'll try to refresh an old post and give it new life and I'm bring it up for readers who may not have caught it the first time that it went live.

Bryan: It's a good idea, yeah. Probably something I should do more of. Would you spend a lot of time looking at the other parts of running a site, for example, Google Analytics or the opt-in sequence that you'd have for email subscribers or the lead magnets that you'd offer on The Write Life?

Jessica: Yes, we do. So last year we did a huge SEO overhaul on the site, and we worked with an SEO consultant and he really helped us hone in on some keywords that we were really ranking for and keywords that we had the opportunity to write for. So we did a lot of work around organizing our site, really getting our SEO up to par, and then we did spend some time reworking our email sequence. We recently switched over in the last year from MailChimp to ConvertKit, and ConvertKit has been awesome because it allows us to really easily add opt-in boxes to specific posts.

Jessica: So for example, we have a really cool PDF of 100 writing prompts, and we have a post that's specifically about writing prompts and why they're so valuable. So when you come to that post on our site, we have that nice little pop up that comes up that says, "Would you like these 100 writing prompts?" That's not something that we would want on every single page, but it's really great that if someone is on that post, they're obviously interested in writing prompts and we can serve them that opt-in that will be really useful to them and really valuable. So that's something that we've gotten really about over the last year. ConvertKit has been really cool on that front to help us level up our opt-ins.

Bryan: Yeah, this might be a slightly nerdy question, but I've used ConvertKit for the last few years and it is great for creating the opt-ins and their forms, but because I've used it for so long I have a lot of different forms and opt-ins. Did you create a system for keeping track of them all, or a you just relying on the ConvertKit dashboard?

Jessica: That's a good question. Right now we're just relying on the ConvertKit dashboard. I don't think we've gotten too into the weeds there yet, so we haven't really encountered that, but we're fairly new to ConvertKit, but really excited about the different results that it's already shown us. Our list has been growing and that's been really exciting for us.

Bryan: In terms of freelance writing today, do you feel that the niche itself has a lot of competitors for The Write Life, or do you feel like the internet is so big that there is room for many sites on a similar niche?

Jessica: Yeah, I think that there are a lot of sites out there and I think there's a lot of great competition and a lot of people that we're friendly with in the writing world. For example, every year in January, we publish a blog post of the 100 best websites for writers as nominated by our community. So while there's definitely competition out there and there's other sites out there, we love to spread the wealth there and we share who our writers love as well. So we like to partner with lots of different writing blogs and sites too.

Bryan: Yeah. That's a good approach. And I'm also curious, do you do all of the work on the posts from editing to proofreading or do you involve other team members in that process?

Jessica: So typically we'll have a post come in from a contributor. I'll typically be the first one who edits it, works directly with the writer. We have a couple other people who we work with who will help with headlines, but for the most part, it's a pretty small team. It's just me and Lexi really working on the site together.

Bryan: Yeah. That's one of the great things about running an online business. You actually don't need an awful lot of people or tools to do it. You can do it from your home office or from your kitchen. What about in terms of planning ahead? So sometimes I'm like, what is it, I could be truly months ahead with content for the site, and other times I could only be a week or two ahead, but does your team work months in advance, or how do you approach your publication schedule?

Jessica: So we typically try to work at least a month ahead for the past year or so. Like I said, we went from publishing five days a week to then one to two. We really played with the cadence over the past few years. So there was a time this past year where we had probably 15 to 20 posts that we needed to publish. So we weren't really commissioning new content because we were really working through that backlog since we decided to go to a lesser cadence of publishing. Right now, we're at the point where we've worked through that backlog and we have bunch of posts that we're working to refresh right now, but we also mix in new content too. So we try to plan out about a month or so, but again, like you said, that's the beauty of being a smaller team. We're able to be really nimble, we're able to change things on the fly and it's a little bit easier to be flexible with those deadlines and the cadence.

Bryan: And in terms of your traffic for the site, I mostly rely on SEO traffic and also email subscribers and listeners to the podcast. I did do Facebook ads for a time, but I stopped using them. Is that something that you've used for The Write Life?

Jessica: It's so funny that you mentioned that. We've been playing with Facebook ads for, I would say the past few months. We've been working to find the right consultant to help us with that because it's not something that I'm an expert in, certainly. We've been working on that because we see a lot of opportunity there, but like you, we really rely on search traffic, and I think that's where a lot of the SEO work we did last year is really starting to pay off, which is super exciting. Because SEO, as you probably know, it's a long game. It takes a while for things to change, and every once in a while, Google will drop a new update and then you'll see things either increase or decrease in rankings. It can be really interesting to follow that. So yeah, we see a lot from search traffic and then of course from email traffic and that social traffic is something that we're playing with now.

Bryan: Yeah, it can take months to get results from SEO work, but then it can last much longer, and obviously it's a lot cheaper than running paid advertising. So one thing I've found is, I've worked as a freelance writer and also when I'm publishing posts on Become a Writer Today, I would edit the post as well. So I found that I like writing in the morning and editing in the afternoon. So if I'm writing something that I'm going to publish myself, I'll work on it in the morning, whereas if I'm editing an article that somebody else has written for my site or for another project, I'll work on that in the afternoon. Do you write a lot, and if so, what type of articles or content do you like to write, and when do you do it?

Jessica: Oh, Brian, you're bringing up a great dilemma that I'm facing right now. I find the balance between writing and editing pretty difficult. I used to do a lot more original writing than I do now, and it's something that I really miss. Like I had said, my background was initially in PR and I switched over to running my own business four years ago and have transitioned really to what I call content management, so helping people and helping clients run their blogs and edit their work. So for the past year or so, I've been really heavy on the editing front, which I love, but I've definitely found that doing so much editing has taken me away from doing my own writing. It's something I really want to get back into.

Jessica: So I actually recently launched a content newsletter all about content to help me get myself back into writing and publishing and sending things out on my own, but it's definitely something that I've struggled with. I do prefer to do my editing in the morning. I find that I'm most fresh when I wake up and have that first cup of coffee and can really dive into editing work and especially headline writing. I know I mentioned that a little bit earlier, but headline writing is something that's so important to The Write Life, and I find I really need to be focused and creative to write good headlines. So I do a lot of that work in the morning and I usually spend my afternoons doing some more administrative tasks like writer payments or editorial planning, working on the editorial calendar. But I really try to spend the mornings doing the most creative work that I can.

Bryan: Yeah. Sounds like a good way to structure the day. Do you write fiction at all or do you focus on nonfiction?

Jessica: I don't write fiction. It's something that I've dabbled with in the past and maybe one day in the future, but it's not something that I'm currently doing.

Bryan: Yeah. I used to write fiction, but then I suppose as I got into online publishing and blogging, I just doubled down on nonfiction. It's probably what I enjoy reading most of as well. So that's the type of writing that I like to do. What platform did you launch that newsletter on, just out of curiosity?

Jessica: I actually just launched my newsletter on MailChimp. I had this idea to launch this newsletter in, I believe it was May of this year. And I typically spend a lot of time planning. I'm a planner and I don't typically launch things quickly, but I had this idea on a Friday and I decided I wanted to challenge myself to just launch something quickly. So I thought about it over the weekend, fleshed out the idea, and then I just launched it the following week. And MailChimp is something that I'm super familiar with. It's what I've used for many years with different clients. So I decided to just launch on the MailChimp platform and it's been going really well so far.

Bryan: That's fantastic. I launched a personal newsletter a while ago, but I use the platform Substack. I mean, I guess the tool doesn't really matter, but I just like the way Substack is set up for newsletters and it's quite easy to use. How do you get subscribers to your personal newsletter, or followers?

Jessica: I created a very simple landing page, again, just through MailChimp. I really find that MailChimp has really improved over the years. I mean, they have really beautiful landing page layouts, and I just created a landing page there. I promoted it on my social media channels. I'm pretty active on Twitter. I'm pretty active on Instagram. So I shared it there. I also have a larger email list from a blog that I used to run, so I sent it out there and let people know that I was starting a content focused newsletter. My other blog was a little bit more personal. So I wanted to let people know that if they were interested specifically in news about content and the writing world that they could subscribe to this newsletter.

Jessica: It's a smaller newsletter for sure. I think right now I'm up to 150 subscribers, so it's definitely small, but it's growing. And like I said, it's really keeping me excited to write and to stay up to date on what's going on in the industry, because when you're so in the weeds with doing the work, I find sometimes it can be hard to see what other people are doing and take a look and see what's trending in the industry, what's going to be coming next. So this has really challenged me to on a... I call it a weekly-ish newsletter to give myself an out if I don't have it every single week. So about every other week I send it out and it's been really fun and it's gotten really good feedback, which is great, and it's helping me to kind of... The goal with this also was to position myself as a thought leader in the content management world and to start throwing my hat in that ring a little bit more, because like I said before, I was doing PR, I was doing a little bit of content editing, I was a little all over the place and now I really focused in on what it is that I do.

Bryan: What's the URL, or where can people find that newsletter?

Jessica: People can find it by going to

Bryan: Okay, very good. I haven't used MailChimp... God, I'd say it's five or six years now. At the time we used it because they had free email software, but I gather they changed quite a lot. But it does seem to me that the way things are going are towards one, personal newsletters, like what you've created, at least for writers, and two, on Medium. So a lot of new writers these days can get their start on Medium, and I suppose I'd recommend it to new writers because you can actually earn a couple of hundred dollars with a little bit of work, which I often think is encouragement for somebody to stick weight writing. Have you explored or has The Write Life explored Medium much, because I know they allow syndication of content on the platform, which is something I've looked at as well.

Jessica: You know, that's something that we haven't explored and perhaps we should.

Bryan: I've written for a few publications on Medium. I guess the only caveat is you don't own... Medium own the platform whereas with WordPress you own the platform, I guess. But it just seems like a good opportunity for freelance writers these days.

Jessica: Yeah, and I love what you said about Medium being like a lower barrier to entry, and that's what I think about MailChimp too. I think MailChimp is super easy for a new writer or someone who's never run an email list to get their start. And I think the hardest part about doing anything is getting started, so if you can make that process a little bit simpler for yourself, that's always a good thing.

Bryan: Are there any other emerging trends that you've noticed started as you talked about recently in your newsletter related to content?

Jessica: I think really I've seen a lot of people talking about just the content mix. What is content these days? Is it blogging, is it video, is it Instagram stories? And I think just the changing definition of what content is, is something that I've seen a lot of people talk about. For me, I feel like I've been blogging on and off for more than a decade now, and I love blogging and I hope that it never goes away, and I feel like a lot of people think that blogging isn't as much of a thing anymore, but I still think it is. And I think that people are still starting blogs and there are a lot of other great content platforms out there. I mean, even thinking about a site like TikTok and Instagram lives and there's so many people getting started on YouTube, and this is all content.

Jessica: So I've been seeing a lot more people talk about the content mix and what that means, but I hope that the written word and blogging never goes away because, like you just mentioned with the personal newsletters, I love sending that out because I feel like it's me sending a personal note to the people who have opted in to hear from me. And I often love the back and forth that comes from that when people respond to a question that you've asked or they respond to tell you a story about something that you've written. And I hope that that never goes away.

Bryan: Yeah. I like your description of the content mix. I mean, the internet thrives or lives on content and it's not necessarily that you have a blog and that's it. You can incorporate podcasting or video or whenever you're doing on social media onto your platform or your content mix. So one great way that writers can monetize their work and earn more money is through creating an online course where they can teach what they know to other writers. I've created online courses over the years and and I know The Write Life has also offered courses. It was a great opportunity to be asked to be involved in the writer's bundle, which is launching in September. Would you be able to tell listeners a little bit about the bundle and what they can expect from it?

Jessica: Yes, we are so excited about the bundle, and we're happy to have you be a part of it. So the writers bundle is a really exciting deal. It's a three day flash sale. So what that means is we've bundled together 12 courses and tools from successful freelancers, from names that you would probably recognize. Stephanie Land, Kristin Wong, Elna Cain, Yuwanda Black, lots of people are in this bundle, and together, if you were to buy each of the trainings, it would cost about $2,000. But for three days only, and through this deal, you can get all of those courses for just $99. So we call it... It's a flash sale. So it will be launching this year on September 14th at 6:00 AM, Eastern Standard Time, and it'll just run for three days only, so we'll end on September 16 at 11:59 PM Pacific Standard Time.

Jessica: It's something that we've offered. We've done it a couple times in the past. We haven't done it for a few years. We're bringing it back for 2020. And what's really special about this year's bundle is that it's totally focused on freelance writing. So in the past, our bundles have been a little bit more general. We've had products about freelance writing. We've had products about traditional publishing, writing fiction, but this year, given all that's been going on, especially with COVID and people sadly being laid off from jobs, I've just noticed a lot more people having an interest in what it might be like to freelance write, and to start your own thing on the side. Some people are finding themselves with maybe a little bit more time to do those things or pursue dreams that maybe they haven't had time for before, or maybe they're just recognizing that now is a great time. So we thought that this year we would really focus this year's bundle on freelance writing specifically to help people who either want to start freelance writing or people who are already doing it and want to level up their careers.

Bryan: I'm looking at the page here, and you have a course from Dave Schools who I know from Medium, who's got expert tips for writing on Medium. You have productivity course for freelance writers. You have a social media starter course for freelancers. That'd be great opportunity for any freelance who's looking to maybe supplement their income with everything that's happened over the past year. As somebody who's worked as a freelance writer, it is something that you can do from home and that you can do online as well. So if somebody wants to buy the bundle, where should they go? And I can put a link to it in the show notes as well.

Jessica: Yeah, definitely put a link. So the website that they'll go to is

Bryan: Okay, that's fantastic. I would encourage people to buy bundle if they're interested in building their freelance career. And of course if you've got questions, you can send me an email and I'll ask questions about it as well. Where can people find more information about you if they want, Jessica?

Jessica: I'm at, and then you can find The Write Life at

Bryan: Was very nice to talk to you today.

Jessica: Yeah, thank you so much for having me. It was great to get to know you.

Bryan: Thank you. I hope you enjoyed this podcast episode. If you did, please leave a rating on the iTunes store. And if you want to accomplish more with your writing, please visit, and I'll send you a free email course. Thanks for listening.

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