Kaleigh Moore is a freelance writer covering retail and e-commerce for software companies like Shopify and Stripe. She also covers sustainable fashion for publications like Forbes, Adweek, and Vogue Business.
Kaleigh started her freelance career nine years ago and has grown her brand into an amazing mix of B2B SaaS content marketing, authoritative retail journalism, freelance community building, and consulting.
Allie first met Kaleigh five years ago, when she was initially considering her move into freelance writing. She was Kaleigh’s first coaching client and gives her full credit for where she is today.
In this episode, Kaleigh and Allie discuss everything from a career in freelance writing to honing their own creative catalysts in a noisy world.
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9:00 – Find a niche to open doors
Once upon a time, Kaleigh ran a successful eCommerce business of her own. That experience helped her sink deep roots into the niche of eCommerce writing.
“I’ve navigated and fallen into that sub-niche within the eCommerce world. And I think that was part of the reason I’ve really put a flag in this particular area, because a couple of years ago my husband was like, this D2C space, this direct to consumer space is emerging. And you should look into that. And there’s this whole community online of people who will talk about this one specific area. Being enmeshed in that community and becoming part of that world, it opened doors to new opportunities as well. So not only does it help the client work that I still do today, but on the reporting side of things it’s opened more doors there. It’s helped me get more trend insight, news insight, things like that. So those two things go together really well.”
10:27 – Participate in communities
A thriving writing career is built on more than just writing skills. It’s also about creating a network. Kaleigh accomplished this by finding and engaging with online communities.
“I went to Twitter, started seeing what these people were talking about. And then those conversations sometimes moved into Slack groups or one-to-one phone calls. I just evolved from there. But I think also it’s looking to the niche publications who are writing about those types of things too. So just by finding them and then becoming part of those communities and really participating there and getting some name and face recognition. I know that sounds vague when I talk through it, but that’s really how it happened…staying engaged with the communities is like my office water cooler. I have been working alone from home for eight years. There’s no sound on all day long, because I can’t write to any noise or anything. So I use those as breaks throughout the day to talk to people, and to feel that connection, and to beat away the isolation that sometimes comes with this type of work.”
11:52 – Find the formula for maximum productivity
For Kaleigh, working in short uninterrupted bursts is the key to quality work. She sets aside a morning and afternoon chunk of time for deep work, with no calls or meetings allowed.
“I typically do two main sprints for my workday, one in the morning, one in the afternoon. I break it up with a really short lunch break and a couple of dog walks. So a lot of it, I sit down around 8:00 most of the time and I’ll do my first sprint. I’ll start with some email, just putting together my to-do list for the day. And then I’ll get into a sprint of deep work for about two, two and a half hours. Take a walk, come back, answer a few more emails, take a lunch break. Another work sprint in the afternoon, about two, two and a half hours. Because I find that much more than that, the quality really starts to drop off. So I’ve tried to just really tap into those two parts of the day where I know I can be really productive and try to maximize those as much as I can. So no calls then, no meetings. Just sit down, knock off the to-do list for the day.”
13:54 – Develop a sixth sense for capacity
Kaleigh recognized early on that stretching herself too thin benefits no one. These days, she has a good feel for when her plate is full. She’ll communicate with interested clients accordingly.
“I know what my capacity is at this point after doing it for so long. So I’m just always mentally tracking. I have a paper to do list and just like a spreadsheet of all the things that I’m doing right now. Deadlines, due dates, all of those things are written down. So they’re always right in front of me. So I’m always just really cognizant and mindful of what’s coming up and how full my plate is. And so once the plate starts getting full to the point where I’m a little bit nervous, that’s when I start saying, okay. My next available start date is like three to four weeks out. And so I’ll start getting myself some padding before the next project.”
15:29 – Behind the curtain of freelance writing
Kaleigh and her friend Emma started the podcast Freelance Writing Coach to give new freelancers a behind-the-scenes look at how they started their journeys and how they operate their successful businesses today.
“What we do on the show, which is called Freelance Writing Coach, we just talk about issues and questions related to freelance writing. Because there’s no real guidebook when it comes to how do I do this? How do I get great clients? How do I know not hate my life every day? So we talk about those things. And a lot of the time it’s just answering questions we get from listeners and talking through how do I put together a great portfolio, or how many clients should I have, and things like that. So just talking through our own experiences, but trying to shed some light on these types of topics for people who are in the same boat.”
17:56 – Freelancing is a career path
Even today, there is a certain stigma around freelancing. But Kaleigh knows that freelancing is a career path that can be just as profitable (if not more so) as any other.
“There were so many things I wish I knew and I hadn’t learned the hard way. It’s really just sharing those things that I learned through trial and error, in hopes that it’ll help somebody else skip over those things that I was like, I wish I would’ve known that, or I wish I wouldn’t have done that. Like you said, it’s coaching at scale. It’s sharing that expertise. It’s just trying to shed some light on this. Because again, people hear freelance writing or freelance anything and they’re like, oh, you don’t have a job. Like you’re doing this in between full-time roles. And that’s the conception. So I want to share that this is a really viable career path and it can be really profitable. And it’s something you can do for a decade or more, rather than just a stop-gap career solution.”
19:06 – Businesses will always need freelancers
When a new business is scaling, they need freelance writers becuase they can’t afford a full-time hire. Once they have a full in-house team, they often still need help for overflow work. It’s a win-win for freelancers.
“For a lot of especially small teams who are just getting started, freelance is just like the most natural fit for them. Because they don’t have the resources to hire full-time team members, but they need help scaling up what they’re already doing. Especially when they can hire subject matter experts, it’s just a really natural fit. So it depends. Sometimes they eventually want that to evolve into a team of in-house writers. But at least in my experience, there’s still always freelance writers that are part of the equation. Because even with the in-house team, there’s still so much to do day to day. So as far as production and scaling, they still need that external help.”
20:58 – Raise your hand for new opportunities
One satisfying partnership came when Kaleigh teamed up with Paul Jarvis to help him run Creative Class. The relationship started because Kaleigh took initiative and offered to help.
“Creative Class was a course on the business side of freelancing. I took it my first year into freelancing full-time, so that was like 2014 I took the course. Again was still before that just doing a lot of different random projects, no real niche or specialization. And I took that course and I was like, oh my gosh, this is the secret. This is how I become a go-to person. I need to specialize. I need to have really professional looking processes in place. Basically I just need to get my stuff together. I need to have a workflow and be a professional person when I come into these working relationships. About two years after that, Paul sent out an email and was basically just doing a survey on ‘Hey, I’m going to do version two of the course, what can I do to make it better?’ And right off the bat, I was like, you need X, Y, and Z, and I can help you do them. And he was like, ‘okay, why don’t you come on board as a partner?’ And so just by raising my hand and saying I have an idea and I can help you execute it, that opened that door to that partnership. And so he and I did that as co-teachers and collaborated on the next version of the course. And that ran for probably three years. I think we had six seasons of our podcast together. We had probably close to 3,500 students go through the course.”
24:52 – Set boundaries for a well-rounded life
When you’re a talented professional, it’s hard to know when to stop. There’s always one more big project around the corner. It took time, but Kaleigh realized she needed a healthier work-life balance.
“I’m one of those people who feels like I could always be doing a little bit more. And that’s a really slippery slope, especially when you’re very competitive, you’re very driven. It’s really easy to be always on, always taking things in. And so I’ve gotten to the point where I had to start going to therapy. I had to start pumping the brakes a little bit, because I was just so overwhelmed. When I would lay down to go to sleep at night, my head would just run and run and run. And I would think about all the things I still needed to do, all the things I still didn’t get done. And it was just like this never-ending cycle of bad feelings. And so I had to put some boundaries in place. I just recently took social media off my phone, so I’m experimenting with that. And if I want to look at it, I can look at it on the computer. So that’s one thing I’ve done. But I’ve also made sure to make time for things that are totally different from what I do day-to-day. So lots of time for reading, lots of time for exercise, being outside while it’s nice. Just building in some healthy habits.”
32:37 – The process for eComm content versus journalism
Kaleigh outlined her process for long-form eCommerce writing, which is much more research-heavy and time-consuming than a reported piece.
“The software and eCommerce writing work that I do is usually pretty long-form, pretty research-heavy. So that workflow and process is very regimented, very structured. It starts with the super detailed writing brief. And then I just do a brain dump when I’m researching. So start building out a messy outline and then tweaking the outline to make it cleaner, make more sense, more organized structurally, things like that. Then do some outreach to people, get some quotes to tie in, get some data, get some images, get some examples to tie in. So that’s the format for how I build those out. But for a Forbes or journalism-type reported piece, it’s a lot quicker. It’s usually a matter of here’s the focus of the article. Here’s some research to support it. Here’s some insight from an analyst or somebody within the space and that’s it. Because they’re pretty short form. They’re usually 850 words, so they’re really quick to knock out. And it’s a pretty formulaic approach…that’s another benefit too to really knowing the space, is that you can easily spot the trends and things that are new and position those as here’s something we need to be talking about.”
35:50 – Consume content selectively
When it comes to what she reads and who she follows, Kaleigh is an advocate of quality over quantity. On Twitter, she seeks out and follows others who are sharing valuable insights, and unfollows the rest.
“I look for people who focus on one really specific area when they’re tweeting. I want to know what their expertise is, what they’re talking. I don’t mind if they sprinkle in some personal things, that’s totally fine, but I want there to be a good amount of value from the things that they’re sharing there. That’s also what I try to do with sharing writing and freelancing insights through my Twitter account. But it’s just really strict. I have less than a thousand people that I follow. And I’m always going through and being like this person hasn’t said anything for a while, so I’m going to unfollow. Just keeping it pruned down and making sure that there’s as little noise as possible. So I want people who are really active, who are talking about things that are relevant, interesting to what I’m doing, and that are well-known within the space too. I want people who are not just brand new to the topic coming in to chime in, but have some sort of foundational expertise around the topics.”
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