Introduction & Podcast Theme
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Emotional support is provided by Hippocampus Magazine. Visit hippocampusmagazine.com to read all the wonderful essays and to submit your own work. Hippocampus Magazine, create, share, live. Attention, parental advisory, explicit riff.
00:00:22
Speaker
Well, well, well. Look what your subscription dragged in. Another episode of the Creative Nonfiction Podcast, the show where I speak to the best in narrative journalism, doc film, radio, essay, and memoir about the art and craft of telling true stories so you can get better at your own work. You're subscribed, right? If you're not, head over to iTunes Apple Podcast and lay it down.
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We're also on Spotify. Oh yeah, that's right. The whole catalog is over there streaming. If that's your thing, please leave a rating or review on Apple podcast, because that's how we prove to the newcomers that we're doing something special over here at CNF pod HQ.
Introducing Jennifer Gregory & Her Book
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Today's guest is content marketing writer, Jennifer Gregory at by Jen Gregory on Twitter.
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What's especially great about this episode is how Jennifer shows you how you can make six vague years writing content for companies. Her book, The Freelance Content Marketing Writer, is a great blueprint for starting to make some scratch with your own words. Maybe you want to add some extra income to the journalism you do, or maybe you can make an entire go of it, make a nice living.
00:01:44
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Most of us artists tell ourselves the same starving artist narrative and where does that get us?
Overcoming the Starving Artist Narrative
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It makes us bitter, resentful, hateful people. You know how I know that? Because I'm a bitter, resentful, and hateful person and I dislike that to my core.
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Hey, I'm working on it. I'm working on it. That's what this show's about. It's me working through some things and I'm glad you're here for the ride. I know it's made me a less jealous person, a less resentful person too. Not entirely, but certainly better.
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Jennifer's book is like seven bucks on Amazon and it might be the best seven bucks you ever spend. I mean, the $7 could turn into 20,000, 50,000, $100,000. I'm not good at math, but I can tell that's a good ROI. What else? Is that it? I think that's it. Like I said, leaving a rating or review and sharing this episode with a fellow CNF or across your social platforms is super helpful.
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I'm probably gonna be setting up Patreon, something or other, too, in the not too distant future, so I don't have to board up the windows here at HQ.
Community Building & Support
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I'll probably offer some cool-ass stuff for your monetary support. You know, there's a great Simpsons quote when Mayor Quimby was running for mayor against Sideshow Bob. His slogan was, if you were running for mayor, he'd vote for you.
00:03:14
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So my Patreon slogan will probably be something like, if you had a podcast, I'd give you money. Anyway, here's Jennifer Gregory.
00:03:32
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Um, so, because I don't, I don't do coaching. I don't do paid coaching. I don't do training all because I don't want to take money from writers. I actually do free phone calls with any writer that wants help. Um, I've been doing that for a few years, so I just like to help people. So I had to take a break in summer because I've been doing two to three coaching calls a week for about two years.
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So yes, a lot of people take me up on it and a lot of people get benefit. One of my superpowers is helping people brainstorm ideas for potential clients. And so I can really help change someone's path by helping them figure that out. So there's a big benefit for me helping someone in 10 minutes. Sometimes I can change their whole career.
00:04:30
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thought process and get them on the road to making more money so that they can have freedom to do what they want. That's neat. You read the book. I was trying to explain to someone that it's a really personal book, even though it's about content marketing. They're like, how can that be? I'm like, no, it really is.
00:04:48
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Yeah, yeah, for sure. It's great the tracking your personal journey through this and your discovery of how you can really thrive. And so many people, so many artists, and we can certainly dig into this.
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to get to this more later, they tell themselves that starving artist story and it really, it boxes you in. I mean, I do it, I'm guilty of it too and it really is handicapping and hampering to have that heavy blanket on you that in order to be
00:05:25
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writer you have to be struggling and you can't make ends meet in any way and it's just like you know your your story in your book kind of it opens up another wing of you know if you if you are a journalist but you want to have this other thing this can help they can piggyback on each other or you can do content marketing exclusively sometimes it's it's a but yeah your book kind of opens up that door for people I think in your website of course
00:05:52
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Well, interesting. The other thing I like to do is helping writers. So by making more money in this way, I'm able to do my blog. I wrote the book. I'm Secretary of American Society of Journalists and Authors and volunteer a tremendous amount there. So it frees up what else I want to do, which is help writers. So it's kind of the same.
00:06:12
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Yeah, of course. And I think embedded in what you're doing and it's, I'm a big fan of Chase Jarvis, who's a photographer and founder of creativelive.com and he's got great podcasts and good social feeds and whatever. A big part of his
00:06:29
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His mission so to speak is and his advice to anybody is to build community and and you have to master your craft but you also have to foster a community and i think what you're doing. By helping other writers is really being a leader in fostering a sense of fraternity among among writers and helping them out because of a rising tide truly floats all boats.
00:06:53
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Have you been to the Facebook group that I started? Holy crap. It's really awesome. I have not been to that yet. Oh my goodness. There's like 530 people there and they're like all nice. And if someone posts something, everybody helps them. It's like amazing. It's exactly what I would have dreamed would be. And it's just really, really awesome. So you should go there.
00:07:20
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Oh, for sure. Yeah, I'll definitely, definitely piggyback on that group for sure. That'll be that'd be great. But it would also be nice to kind of unpack a bit of your origin story.
Jennifer's Writing Journey
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So where did you grow up? You know, what did your parents do? What kind of kid were you? Well, I was always a writer from the very beginning. I wrote poems every time I could find a piece of paper to write on.
00:07:46
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And I don't even remember not knowing when I wanted to be a writer, but it was just always what I was going to do. And then became the classic struggle when I had time to make them go to college. How was I going to make money with that? And that was a struggle for the whole couple of years in college. Considered journalism, but I wasn't sure I could handle some of the tragedy and tougher parts of that job. Considered teaching English.
00:08:16
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But I wanted to have more flexibility with money than that was going to provide. And so finally I found technical writing. And basically the reason I picked it was because I could take all the cool English classes and my dad would still pay for my college. And so I ended up getting a technical writing degree. So and then I spent a couple of years working as a technical writer at various software companies, including IBM. And I was a terrible technical writer.
00:08:45
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It was okay, but what I ended up doing was spending most of my time trying to make value in other ways. So I started a usability project, a customer program, a training program so that nobody would realize I sucked at being a technical writer. And then when my kids were born, I took six, seven years off. And when my youngest went to school, I started freelancing and I had no clips and no contacts, but
00:09:11
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I wanted to figure out how to make it work and that was in 2008. That must have been a tough time to kind of hang out your shingle too as the economy tanked. You know, I was too naive and overconfident to realize that. So I think that was kind of to my advantage. I never thought that I wouldn't be able to make it work. So it didn't affect me as much as I think it would have if I had already been established.
00:09:41
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But it did take a few years and at the time I didn't really, probably the economy did have something to do with it. But I did some local, I worked for the local newspaper, I did regional parenting magazines. And then in about 2011, landed my first content marketing job, even though I didn't realize it was content marketing at the time. And where did you grow up? Oh, I'm sorry, Gainesville, Florida. Go Gators! Nice, very nice. Tom Petty, Tom Petty's hometown.
00:10:11
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Yes, now I'm in North Carolina. What did your folks do for work? My mom was a math teacher and my dad was a banker. A writer came out of that. Well, my mom actually, yeah, they never quite knew what to do with me. In what way?
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My mom probably a little more, but just because they both have more of an analytical mindset, so it was a little challenging having a kid that was more of the creative bent.
00:10:41
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So when you're starting to want to become a writer, what was some of those, maybe in college, what were some of those discussions you might have been having with mentors or even your parents when you were trying to tell them, hey, this is something I want to pursue? Did you get any pushback? And if you did, how did you roll with that and react to it?
00:11:05
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The pushback was just that I had to get a degree that I could actually make money at. My dad wasn't going to finance a degree that did not have a career path. That was a huge struggle trying to figure that out. I'm glad that he had that mindset because I didn't at 19. I'm glad that he made me be practical about it. I think that having that at the back of my mind has always helped.
00:11:34
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As much as I didn't really enjoy technical writing, I'm really glad that I had that experience because it's what has actually helped me get where I am today with the knowledge of technology and working with technology experts. But also more the corporate side that's helped a lot too with going into content marketing.
00:11:58
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Yeah, it sounds like as maybe as at odds or just fundamentally like different your brains were at that at that time and maybe if there was any.
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Any friction, it looks like it's been very valuable for you because you're able to divorce, say, the artistic side of your brain and then the very analytical business side of things. So it looks like having the analytical chromosomes in your DNA have definitely helped you as you've progressed as your own independent writer. Absolutely. And when you take those little left brain, right brain tests,
00:12:41
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I'm actually typically right in the middle, which is probably why I've been able to be successful. I'm creative, I can see both sides, and I can be both sides depending on my mood. And so you hang up your shingle, so to speak, in 2008. So what were you doing to try to drum up momentum and start to spin that flywheel?
00:13:07
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Um, well, you know, I wanted to be in the big glossy magazines in target, of course. Right. And so, but I started out in content mills making $25 for an article, because I needed to, to bring in a little income and was sending out pitches and it wasn't, it wasn't working and probably because of the economy as well, but got some traction with working with the regional parenting magazines and with, um, the Raleigh, um, Raleigh News and Observer newspaper.
00:13:35
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Got an editor there that was fabulous that taught me a lot about writing and was exceptionally valuable. Wrote a couple hundred stories for them and had a couple columns in the News and Observer and that was a big turning point as far as learning the craft. And so that brings me to, you know, 2011 and I had some clips and I was a much better writer than I was three years before. And at that point the kids were getting a little older and I realized I needed to get serious, you know, making 25
00:14:04
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$20,000 a year just wasn't going to cut it. I started getting serious on the marketing and weirdly enough, I signed up for a contently ad and got put on some projects with contently and wrote about webinars, a bunch of articles about webinars. Then someone liked my work and put me on American Express Open Forum and that was a huge turning point in my career.
00:14:31
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Yeah. So it's kind of like, you know, work begets work. And sometimes you don't know where it's coming from, but it's like you have to be constantly putting it out there. You don't know. I mean, what is it? Luck happens when you're in the right place at the right time, but you don't know where that's going to be. So you write, you just have to keep putting it out there. I wouldn't, I wouldn't have thought that my lucky break, so to speak, would have come on a webinar project, writing five ways to make webinars boring over and over and over.
00:15:01
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So what were some of the daily practices that you put in place so you could start to measure some of these things and see what was working and what wasn't? One of the things that I've always done is set goals that I can control. So instead of saying I'm going to get a new client this month, I would set goals of the activities that are likely to make that happen. So it would be I'm going to send up
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50 LOIs every week and make five contacts and go to one in-person event. Because I can't control if I get a new client or not, but then if it doesn't happen, you feel defeatist. But if you just do the activities that are likely to, then it's more uplifting and you're likely to actually do them.
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Right, and LOIs are letters of introduction for people who aren't too familiar with that term yet.
Understanding Content Marketing
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Yes, and so that's the way that you introduce yourself to both trade publications and people at agencies and businesses that may need a content marketing writer. Where did you start to hone that letter, LOI, and then start to get business based on some of those cold interactions?
00:16:18
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I followed Carol Tice's blog a lot and so learned a lot from there in Kelly Jane's anger, who's now a very good friend of mine. Her six figure freelancing book was instrumental as well at the time. So got started sending it out after I was getting success with Contently and I had some clips and I figured out what it was. When I started, I had no idea what content marketing was and it took about a year till I figured out that I actually knew what I was doing.
00:16:45
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and was kind of on the leading edge of something. It was actually the 2013 ASJA conference where people started asking me about it and it was at that conference I decided to start my blog because I realized that I knew something that could help other people.
00:17:04
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You've done a very great job and a great service to that community by you being yourself and letting your personality come through. How long did it take you to let your be comfortable and vulnerable enough to let your personality maybe come through in a letter of introduction and certainly in the work that you do for a particular client?
00:17:30
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I think that's an evolving process. I know at the beginning of my career when I get on the phone with potential clients and I would try to be what I thought everybody thought I should be and I wasn't really landing clients. I wasn't getting traction and in my book, I talk about this one night, someone from San Jose called me and I'd had a half a glass of wine. So I was very much myself.
00:18:01
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And when I woke up the next morning, I was like, oh crap, I blew it. And when I got in my email box, I already had an assignment and they told me I thought I would be a great part of the team.
00:18:14
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I started realizing that maybe I should just be me and handily likes to say when you do that, you attract the like and repel the different. So when you are just yourself, then the clients that you're likely to be a good fit with organically, authentically are going to be attracted to you.
00:18:35
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you're going to be even more successful. I really think that being who you are is so important instead of trying to be what you think you're supposed to be. Yeah. And for people who might not exactly know what content marketing is or they hear those terms and it sounds kind of slimy,
00:18:57
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Okay, so I hate the term content marketing and I wish it had a different term, but we're stuck with it. Right, right. Yeah, so how would you define it for people who are immediately put off by it and think that it's maybe not for them?
00:19:12
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Well, most journalists have actually already written content marketing. They just don't know it. I have gotten an argument about this, but airline magazines and AARP and Costco connections, those are actually content marketing because it's something produced by a brand. So content marketing is anything produced by a brand. And the goal is to provide information that helps solve the reader's problems with the goal of building trust in the brand.
00:19:41
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So if it looks like marketing, it's not really content marketing or it's really bad marketing. Great content marketing looks like journalism. It is not journalism, but it's supposed to have that feel and it's supposed to be reported. It's supposed to provide information. It's not supposed to be slimy and go by my product. That's marketing. So I always say if it looks and smells like marketing, it's not content marketing, it's marketing.
00:20:08
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Yeah, and there's probably a subset of people, too, who feel like that's maybe a form of trickery, too. And are there some companies that you've come across where they feel like maybe their goal is to try to kind of pull the fleece over people's eyes to make it look more like pure reporter journalism when, in fact, it's a paid piece of content?
00:20:36
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Can I not answer that question? I don't really know.
00:20:39
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My examples, I don't want to say, so let's cut that one out. Sure, sure. But have you, like if I, for, for maybe, maybe for, for people who, is there any, is there anything for, for maybe, maybe even readers to be mindful of? Um, so maybe they can be as well informed as a reader as possible that what they might be, what, what is, what's could be considered pure journalism versus something that looks like journalism.
00:21:08
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Absolutely. Just keep in mind that if it's produced by a brand, it has the brand's best interest at heart. Even if it looks like it's neutral, it's not going to tell you the downsides of their product. It's not going to point out anything that makes them look bad, and it's going to only highlight the things that they're good at. Just keep in mind the perspective. It's the same with journalism these days, too. You have to know the perspective that the outlet's coming from.
00:21:39
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Yeah, even find that on Netflix documentaries and even ones that look really produced and almost look true and authentic. An example is I think 180 degrees south, which is about these kind of explorers trying to
00:21:57
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climb this mountain and it's got a big Patagonia feel to it and sure enough like Patagonia is like the main bankroll of That movie and it though. It's not an explicit advertisement for Patagonia It's definitely I would I would say it's it's a content marketing documentary that has these other sort of wings to it to make it feel like a documentary so and
00:22:24
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And the way Netflix too, the way they almost like – you don't even get a chance to really look at the credits too. So if you actually want to see who's making this and who's – it skips over it. So you can be really – you got to be really mindful and rigorous on your own as a reader and a consumer of material.
00:22:41
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So that absolutely is content marketing. Content marketing doesn't have to be written. Um, it can be, um, Topolte did a music festival that's actually content marketing. Um, apps can be content marketing, videos, podcasts. Um, a lot of podcasts are actually content marketing because it's providing information that the brand's producing to help build trust in the brand. So it's not just written. So that is absolutely content marketing.
00:23:06
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Yeah, and I know, you know, Gimlet Media, who does a lot of journalism podcasts, they have a wing, I think, called Gimlet Creative. And I believe they, they partner with the they've done in the past, I don't know if they still do it, but they've partnered with like eBay to, to kind of tell tell these stories that do that exactly what you're saying that do shine the most favorable lights possible, but it does have that more narrative feel to it. So I guess you just have to kind of do your homework to
00:23:37
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Absolutely. As a writer, what are certain things that you struggle with and have to make up for with either hard work or maybe even outsourcing?
Outsourcing & Strengths
00:23:53
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I am a terrible type of queen. I will drop words. That was one of the biggest reasons I was having a hard time getting clients in the beginning because I was trying to overcome that.
00:24:06
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And it just wasn't working. I got fired from a few jobs because my copy wasn't clean. My brain moves fast and my strengths are my ideas and my perspective and my writing, but I'm not from the detail perspective. So first, when I couldn't afford it, I found another writer and we started reviewing each other's stories as a second set of eyes. And then as I got further in my career, I started hiring my own proofreader and I don't send anything to an editor
00:24:36
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without having my wonderful proofreader look at it.
00:24:55
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the typo part, but you would probably be doing that at the expense of whatever it is you deem your strengths. So it's great that you've recognized that. How long did that take you to just recognize that and just to do that and be comfortable with that and then to move on into something you're better at? Probably longer than I'd like to admit, probably three years because on the surface, you think that being able to write clean copy is part of being a successful writer.
00:25:25
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So I kept trying and I kept trying and this was the thing, I was spending so much time trying to make my copy perfect and I still wasn't able to do it. And it was actually at a conference where one of the speakers was talking about, don't try to be better at your weaknesses, try to figure out ways to mitigate them. And that was life-changing for me.
00:25:47
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If you're starting from a zero point, what are some strategies for someone who might be looking to pick this up as a wing of their work or possibly even the entirety of their writing business? How would you recommend and coach someone to maybe take that first step and go from zero to one?
00:26:12
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Well, the first thing you kind of need to figure out is your niche. And while you can be a generalist in content marketing, you really need to present yourself to clients as having expertise because they want you to have industry expertise in their area. So that would be the first thing that I would tell them to do. And if they were starting from the beginning, usually you start with a niche you can already prove. So either a niche that you have a full-time job in or that you have journalism clips.
00:26:42
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And then the next step is trying to get clips to back up your experience if you don't have any. And I do sometimes, I'm not a fan of taking low-paying stuff, but sometimes in the beginning you have to to get the clips. I think you should always be paid for your work, but sometimes it's not always paid in money, but it's not just in generic exposure.
Networking & Ethics in Content Marketing
00:27:03
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You know exactly what you can do with the clips and what you're getting.
00:27:07
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Um, so I think if you're taking a low paying gig, you have to know exactly how that is going to pay you. Um, so it's figuring out your niche, getting the clips. And then the next thing is the best place to start is always with your personal contacts because people that know you are going to be more likely to hire you or refer you. So go back, find people you worked with 10 years ago, see where they are. If they're at a company in your niche.
00:27:34
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Even if they're not in position to hire a writer, ask them for an introduction. Most people are happy to do it. If you were in a journalism newsroom, find all of your friends from the last 10 years because a lot of them are probably at companies. Find out where your neighbor works. So start with your personal connections first is always where I tell people to go, especially if they worked full time in the field that they are now using as their niche.
00:28:01
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And would you recommend someone who's a freelance, say they're a journalist and it's just, it's hard as hell, not only to get paid, but to land stories and ever shrinking markets and contracting newsrooms. Is it possible for a reporter or a journalist to do content marketing as well?
00:28:24
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So there's a couple of ethical things you have to keep in mind. The cleanest way to do it if you're doing content marketing and journalism is to have different niches. So for example, if you do travel journalism, then maybe you'll do hospitality technology as your content niche, or maybe you'll do a health niche. Keeping them separate is the easiest way because the main rule in the sand
00:28:51
Speaker
For me and for most other journalists and writers that I know is that if you take money from somebody as a client, you can't use them as a source in a story because the perception
00:29:05
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The perception's off. It feels unethical. It looks unethical. So the biggest thing to keep in mind is that ethically, if you work for a client in content marketing ready and take money from them, then you can not, should not use them as a source in the future.
00:29:21
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The other two things to keep in mind about doing content marketing and journalism together is to let people know upfront any potential conflict. So if you're working for a journalism publication and you have a content marketing client in that niche, just tell your editor upfront and see if it's okay. Most of them are, but by doing that, you really eliminate any potential problems. And the third, third rule for me is go with your gut, even if it meets the first two rules, but it feels icky.
00:29:50
Speaker
don't do it. It's just not worth it. Yeah. Yeah. Following your gut and like following your taste too, you know, you can kind of raise your, your spidey sense if things don't feel right. And, uh, yeah, that's just trusting your instincts is probably a step one. Absolutely. Um, there was a case where I was working for a hospitality trade publication and also working for Samsung writing for their hospitality sector and everyone was okay with it. But,
00:30:18
Speaker
But it just didn't feel quite right to me, so I ended up dropping the trade publication and continuing on with Samsung. And that felt better to me, and I felt good with that decision. I could sleep with that, so. Yeah.
00:30:32
Speaker
And in your career from 2008 to 2011 and then even in the years when things kind of started to galvanize for you, what were some growing pains that you went through that you had to weather and endure to get to the other side where you actually felt like you had made it?
Freelancing Challenges & Success
00:30:53
Speaker
That's a really good question.
00:30:55
Speaker
Really, the challenge with a lot of freelancers is the feast or famine cycle. In 2015, I broke six figures for the first time. I was so excited, even if it was only by $300. And three weeks later, I promptly lost almost all my clients. This is totally a true story. I lost three anchor clients at the beginning of 2016 and had almost no work and started from scratch.
00:31:24
Speaker
and built it all up again. So I think just knowing that at any moment you could lose an anchor client and you're back to the square one, I think that's a challenge you're always with. There was a two-week period at the beginning of this year where, it was funny, I had a week where I, over a 10-day period in January, I earned $7,000. I started $7,000. The next two weeks had no work.
00:31:54
Speaker
So I think that's just always knowing you're only the next week away from having to look for work again. So it does get easier the further along in your career to pick it back up. That's what I learned in 2016 when I pretty much had to rebuild my client base.
00:32:12
Speaker
It was a heck of a lot easier than it was back in 2011 because I had, I was able to, I had the brand names. I had worked for IBM, Adobe, Samsung, Hewlett-Packard. I had the clips and it came back really quick and this year.
00:32:25
Speaker
In those two weeks, I immediately started marketing, reached out to my former clients, reached out to my writer friends, and it only took about 10 emails, and I was busy again. So the farther you get into your career, the easier it is to do that. But it's going to happen again to me, and it could be next week. Who knows?
00:32:45
Speaker
It takes a pretty special mindset to be able to not only weather it when it happens, but to know it's going to happen as well. How do you process that knowing that it's probably inevitable, but there's no seismic graph telling you that there's some weird energy pulsing below the earth that's going to rock your foundation?
00:33:15
Speaker
I think it's because I'm super stubborn and I'm not, and I'm going to prove that I can do it. And then with freelance and you have to prove you can do it every week again. And so I have that stubborn competitive and myself gene. So that's kind of how I, whether I never, I always thought I could do this. I always knew I could do it. Other people could do it. And when things weren't working, it was just a matter of me figuring out the right strategy or working harder.
00:33:42
Speaker
So I think that the core belief in yourself is so important in this because I don't think that the people that are most, because I don't think I'm the world's most fabulous writer. I'm okay. I'm good. But the reason that I made $154,000 last year was because I'm persistent as hell and I'm not willing to give up and I will send 50 emails in a week. I will figure out how to make it happen. It's the persistence is really the difference.
00:34:12
Speaker
Yeah, that's amazing. And that's not someone misspeaking and that's not hyperbole. You made $154,000 in gross income in 2017. So I think people really need to let that kind of rattle around in their brains for a bit that this is like something that's possible and something that you've
00:34:33
Speaker
you've put into work and orchestrated over the last seven, well, 10 years if you go back to 2008, but it really started to galvanize for you in 2011. So I think people really need to let that rattle around in their brains for a second. And I'll add that I took about six weeks off last year as well. I went to Australia and Hawaii and took another two weeks to hang out with my teenagers. So that was with taking most of December and most of July off.
00:35:02
Speaker
And what would you recommend maybe for people who harbor limiting beliefs that is keeping them – like some people might hear that, and I know I'm guilty of this too, that it's the other who gets to do that. You know, it's, yeah, Jennifer Gregory, she can do it, but for me, that's – I'm – it's –
00:35:21
Speaker
20,000 is a good year and I can't do that. How do you rewire your thinking to say, oh no, I'm holding myself back. That is fully within my reach and my goals if I want to get after it.
00:35:37
Speaker
For me, a friend took me aside and I was all happy that I was making $25 an hour as a writer and she took me aside and told me that was crap and I should be making $75 to $100. I was like, oh my goodness, I'm really selling myself short. I think a lot of that is freelancers being honest and talking about money with each other because
00:36:01
Speaker
If someone else can do it, then you can too. And so I think the more freelancers are open about money and honest about it, the less the starving artist's mentality stays.
00:36:18
Speaker
But the self-limiting, I think a lot of it is just, why can't you? If I can, why can't you? I'm not any better. I'm not a better writer. If I can do it, you can do it too. It's just a matter of figuring out the magic with your strengths, skills, personalities, and goals, figuring out what your perfect clients are.
00:36:42
Speaker
and building a business that's right for you. So there's no one right way to freelance. It's all about what is right for your specific strengths, weaknesses, goals.
00:36:55
Speaker
Yeah, exactly. When I was talking to Susan Orlean a bunch of episodes ago, she's just an incredible writer. She's a freelancer too, but she's been able to carve out her niche doing the narrative profiles and features you see in The New Yorker and book-length narratives and so forth.
00:37:15
Speaker
But she said that you always have to have – not only are you running the business, you are the raw material the business is producing. So there is that – there's a semi-permeable membrane between each side of it, but you need both sides. So how did you learn to cultivate that business part as an integral and maybe the most integral part of your actual writing business?
Mindset Shift & Embracing Failure
00:37:45
Speaker
I think it's because my husband's a small business owner as well. He forced me to take a little bit more of a business owner mindset because that's what I was hearing from him. Every time I talked about work was that perspective and so that helped. One of the biggest shifts for me was when people say, what do you do? Instead of saying I'm a freelancer, I started saying I own my own freelance writing business.
00:38:11
Speaker
That one shift changed everything for me because I started believing it. I started believing it and I started making business owner mindset decisions. So figuring out whatever is going to make that shift for you. But that's a huge thing. I don't think you can be a high income writer until you make that shift and view yourself as a business owner.
00:38:38
Speaker
I also think you have to be, you kind of talked about the self-limiting behaviors and that kind of thing. I think you have to be okay with failing as well. And I mean, okay, so it's the end of July and I've already crossed six figures for the year and that included taking three weeks off. But I got fired from three clients this year because I wasn't the right fit. And that's okay. That's okay.
00:39:05
Speaker
I learned something from each experience that I, when I say fired, I'm being slightly dramatic because, you know, I'm a writer, but it wasn't a fit. I wasn't asked back. I wasn't continued on the project. But I learned something from each one and it was about my strengths, weaknesses, and what my perfect clients are.
00:39:27
Speaker
So I consider that a success but you have to be okay with that. You have to be okay with something not working out. You have to be okay with failing and you have to figure out how to learn from it instead of it beating you down. Do you have a favorite failure that sticks in your mind that always reminds you that this is gonna happen, it'll happen again and I'm able to get stronger because of it?
00:39:55
Speaker
Yeah, I call it the fire pit story. For some reason, I can't write lifestyle content, but I can write blockchain, artificial intelligence, and ghost write for very techie execs at Hewlett Packard Enterprise. But I always seem to think that I can write lifestyle. I was working for a big insurance company, writing insurance content totally fine.
00:40:18
Speaker
And then they said, can you help us out on our home blog? Sure. I can, I can write home stuff, right? I own a home. And so I had, they had me do a couple stories about pillows and paint and it was fine. And then I had to write a story about building a fire pit. Oh my goodness. It took me 20 hours and the company's legal department got involved.
00:40:44
Speaker
And it was horrible to the point that my best writing friend was just like, please let me fix this for you so I don't have to hear about your stupid fire pit story anymore. But it wasn't a fit. And it's taken me so hard long to learn that I can't write lifestyle, even though it feels like I should be able to. So that's one of my favorites. Another one is one that happened this year.
00:41:12
Speaker
It was kind of hard to swallow because it was with a very, very, very large tech company and I wasn't the right writer. And I figured it out pretty quickly. They wanted somebody that was very short and snappy and very detail oriented. And it was a dream bucket list project. And I had to call the person in charge and tell them that I called them and said, I'm not a fit. I tried to take myself off the project.
00:41:40
Speaker
And they talked me into staying. And then two weeks later, they let me go. They said, you know what, you really were right the first time. And that that was that was tough. That was a really tough one for me. But it's OK, because at the same that same week, another really, really big company sent me a note saying, oh, my gosh, the ghostwriting article you just did,
00:42:09
Speaker
It was amazing. You're one of our favorite writers. So it's really just finding the perfect clients for you.
00:42:17
Speaker
And you write also that a big mistake people make is doing outreach or marketing only when you're in need of work.
Balancing Work & Productivity Strategies
00:42:25
Speaker
So how do you balance the clients you already have versus when it feels like you don't need any more with actually going out there and doing some of that outreach. So in case you lose three anchor clients, you've got something coming.
00:42:44
Speaker
I think that's hard and I think that's something I'll struggle with forever as long as I'm freelancing. I try to make myself do the marketing that's more organic. I go to events, I speak on podcasts. I don't do as many cold letters of introduction as I should. My goal is to be putting 10 to 15 feelers out every month.
00:43:10
Speaker
no matter how busy I am, some months I do that, some months I don't. I should do it every month. At this point in my career, it's
00:43:21
Speaker
A lot of times what I'm dealing with is too much work and I refer out to a lot of other writers. So I have writers that I pass leads on to all the time. And the benefit of doing that, I think every writer should refer to other writers. So if I lose three anchor clients in three weeks, I have 15 friends that I can email and say, Hey, if you hear of anything, let me know. And you know what they will because I've helped them out when they lost their anchor clients. So.
00:43:50
Speaker
I think the more you help other writers, the easier it is to pick back up because other writers can help you out. I would say with a lot of what you're doing with ongoing projects and then outreach and doing podcasts and this, that, and the other, there's a lot of
00:44:13
Speaker
tasks and a lot of balls in the air. So how do you organize your day to try and keep things straight and well oiled? You know, it's funny. People ask me all the time to write a blog post about productivity because I also I'm Secretary of American Society of Journalists. I brought in the blog and do my business and I'm have two teenagers.
00:44:39
Speaker
It's funny, I don't feel very productive. Um, and I don't have any huge systems. I actually don't even really keep much of a calendar except for work interviews. Um, I think that the, but I'm actually pretty productive and the trick is that I, I do what works for me instead of what I feel is supposed to be the right way to do it. My to-do list is a word document that I've had going for about 10 years where I write what I'm doing that day and then delete it.
00:45:08
Speaker
But I also try to go with where my energy is. So if I'm feeling, thinking about a certain story, I'll go ahead and write it, even if it's not quite the top priority, because that's where my heart and my mind is at that moment. When I'm not feeling productive and I have a deadline, which was yesterday, I force myself in 20-minute increments where I'm going to
00:45:34
Speaker
right for 20 minutes and then I'll check Facebook or email for a few minutes and then go back. That works for me. So I think it's really following your body's rhythm and your natural habits and figuring out how to work within those instead of make yourself into something that you're not.
00:45:50
Speaker
If someone is having or struggling getting traction with LOIs, what would you suggest they do to reevaluate maybe why they're not getting the traction they want if they're sending out dozens of them a week? So first, a couple things is I recommend a short LOI. I call it the five-ish sentence.
00:46:18
Speaker
And almost every agency, every content marketing and hiring manager says they want something short. And as writers, we want to write a novel. So make sure it's short. The LOI is a pickup line. Don't try to have the whole date in the email. You're just trying to get someone interested in talking to you. So that's the first thing I'd look at. The other thing is look at who you're targeting.
00:46:49
Speaker
a three-step process where you start with the audience you understand and then brainstorm the products and services that they buy and then make a list of all the brands that make that. When you do that, you end up coming up with people that need your experience because they're selling to the audience that you know. Make sure that you're targeting people that need your specific experience and that you have the clips to back it up.
00:47:17
Speaker
And also make sure you're not sending into blind to email address boxes. That's a, um, you'll not get traction that way. The other thing is make sure that you're following up. I think that's one of the biggest mistakes that writers make. If you don't follow up, you're leaving money on the table. I recently talked to, um, another freelancer who had sent, um, an LOI to a company, heard nothing, followed up a couple months later, heard nothing.
00:47:45
Speaker
Followed up a third time, they responded with an assignment and they're now an anchor client of hers. And if she hadn't sent the third email, she would have missed out on like $10,000 this year. So just because someone doesn't get back with you, doesn't mean they hate you. It just means that they're busy and they might not need you right now, but you could be in a special little email folder that they're going to call you.
00:48:10
Speaker
in next year. I've actually gotten work from letters that I've sent in a year or two from them. So definitely don't give up. Kind of what I tell people is if you've sent out 50 letters of introduction and you have followed up and you have gotten no responses that were like, hey, it looks great. Hey, we'll save you nothing right now. Those kinds of responses, then you need to stop. But if you are getting those responses at 50, that's great.
00:48:39
Speaker
At that point, stop, evaluate who you're sending it to and your LOI. If you get to 100 and you haven't gotten work, and you're getting some responses, the problem at that point is probably your clips or your website because you're getting the interest but you're not converting it. So stop and look at your clips and your website and figure out if you need to put different clips up there, if you need to go get different clips, kind of figure out how to convert the interest into
00:49:09
Speaker
into sales and also you could be not targeting the right person at that point too. So those are the two milestones that I tell people to stop and take a breath if you're not getting traction there. Do you have any system or ideas for people to keep track of this so they can adequately follow up on a predictable time scale?
Managing Overwhelm & Collaboration
00:49:34
Speaker
A lot of people will put a reminder on their calendar
00:49:38
Speaker
That's what I would do. A lot of writers will also do the whole spreadsheet with who they sent it to and follow-ups and all that. That doesn't work for me. So for me, it's a reminder on my calendar and then it's kind of silly, but I use the same, I always use the word experienced and is a subject line for my LOIs. And so when the calendar comes up, I will just do a search in my email for experienced in my sent file.
00:50:05
Speaker
and go from there. So the message is really figuring out a system that works for you as silly as that sounds. It's worked for me for five years. So figure out what works for you. If spreadsheets works, if searching your email works, if a handwritten note works, if notes on your computer, on your voice phone works, that's great.
00:50:26
Speaker
And when you feel overwhelmed, how do you deal with that and process that so you have a better headspace and can approach your work with better energy?
00:50:40
Speaker
She's actually turned into so much more than an accountability buddy, but I started with an accountability buddy back in 2013. She turned into a very close friend. I call Stephanie or I email a couple of my writer friends. It's my writer friends that talk me off the ledge.
00:50:59
Speaker
that help me kind of ask me the questions that I need to re-prioritize, you know, what do you have to do now? What can you drop? That kind of thing. So I think having friends that really understand your life and can talk you through the good times and the bad times, it reminds you when you lose three anchor clients that, you know, you've done it before, you can do it again.
00:51:21
Speaker
Do you ever have this feeling of when you lose anchor clients, like three is probably in a year, I can imagine that probably just ball parking is probably 25 to 40% of your total income from three clients. I'm just throwing out an arbitrary number, but I bet it's kind of close to that. How do you think, like kind of rebound from that
00:51:49
Speaker
And how do you not feel that maybe they're like, shoot, if I lost three, there's a finite amount of people out there. Like if I lose these three, I can't find three more. How do you deal with that panic? Well, every business needs content. So they're out there. You just have to figure out the right ones. And I think it's knowing that your options are really limitless. It's a matter of just finding the right fit for you and knowing that in your heart. I actually lost two anchor clients.
00:52:19
Speaker
in June, so this June. One was one that I thought they had hired me for four blog posts a month for a year and then a new marketing manager came in and put a halt on it. They were supposed to be an anchor client. I had done one month of work and another was a project I had had for two years that the agency's contract went out.
00:52:45
Speaker
both neither faults of my own. I try to keep my no client more than 20% of my income so that I can either make it up or do without. I try to actively balance that. And if I can keep it closer to 10, that's even better. Both of these were lower. So that was a positive. But I think it's also just knowing that it's, I expect it to happen with every client.
00:53:13
Speaker
I think of every client is finite. And so just having that mindset when it happens, I'm not devastated because it's going to happen. And I also know now learning the hard way is that if you're going to lose a client for business reasons, not because you suck, you know, it's usually going to be in January or in June. So I kind of expect that in June is the end of the fiscal year.
00:53:40
Speaker
So it seems that a lot of changes happen there. And in January is the end of budgets as well. And a lot of changes happen there. And a lot of contracts, if you're working through an agency, a lot of contracts are on those cycles. So that can happen. Is there a better time in the calendar year to be maybe flooding companies with LOIs?
00:54:02
Speaker
People are going to be hiring at any time. I think that the summer in January is a little harder, but that doesn't mean you shouldn't do it because people are still going to be hiring. I always seem to be the busiest, you know, February to May and then September to December tends to be my busier times.
00:54:23
Speaker
In the last few years, maybe five years or so, is there a belief, behavior or habit that has most improved your work and your life? I think it's a lot of what we've talked about, about really not trying to fix my weaknesses, but figure out how to get around them and just really being comfortable with myself, the good, the bad and all of that and figuring out how to make it work.
00:54:51
Speaker
So I think that is the, I mean, and you talked about the belief not being good enough. I mean, and I talk about this in my book, even a few months ago, in the middle of the night, I decided I was a fraud and I was never going to have success. I think that's just part of being a writer and part of, I mean, even when you're writing content, it's not just content.
00:55:17
Speaker
It's a part of you. It's a story you created. It's something that came from your head and your heart and a lot of stuff I really care about. So when you lose it, it's not just a business transaction. Writing is much more personal, even if it is content. So I think that I always fight that I'm a fraud and all my success is a fluke. That's just kind of innate as being a writer.
00:55:45
Speaker
How have you cultivated a sense of patience with your work? So they, when you were starting on, you know, in the blocks at zero doing this, and you're like, okay, you know, I want to get to this point, you know, but it's going to take me a little bit of time. Like how did that, how did you tell yourself and coach yourself to just be patient, keep your head down and do the work? It was the stubbornness in me.
00:56:14
Speaker
And I never in a million years thought I would make enough to, I never thought I'd break six
Career Growth & Community Support
00:56:20
Speaker
figures. My goal was always, I always thought I wanted to earn what I earned at IBM as a technical writer. So my pie in the sky was 70,000. I thought that would be fabulous. So I never expected to reach this level of success. It kind of just kept happening.
00:56:40
Speaker
When did six figures become a reality for you? Um, it was the end of 2015 and I, one of my things I'm bad at is bookkeeping. Um, that's definitely not a strike. So I had the, you know, deposit it all and add it up system. I've gotten a little better since then. Um, but in early December, I added up my earnings and realized I was a couple hundred short of six figures and I abs, I kind of had no idea.
00:57:10
Speaker
And so I was trying to wrap it up for the year, but I decided to go ahead and take another assignment to put me over. I couldn't end it at 99600. So, um, I went ahead and took another project to kick me over.
00:57:27
Speaker
Yeah, talk about a moment, an empowering moment that it just feels like at that point, you're like, wow, it truly is. If it's possible for me, then if I can do this, then it probably ignited that part of you that wants to help other writers.
00:57:46
Speaker
this is out there for other people and it's like if I can show this and illustrate it and put that six figure thing in my subtitles to books and on my website is be like this is my way to let other writers know that this is out there for you. It might not be the exact writing you love but it might be able to allow you to A, write for a living but also subsidize maybe the more creative stuff that you really wanna do that really sort of nourishes your taste.
00:58:17
Speaker
Absolutely. Because I don't think there's anything overtly special about my writing or about me. I think I've just worked really hard and figured it out. So I really think that it's possible for almost any other writer that's going to put in the work and the effort and be honest with themselves about their strengths and weaknesses and figure out how to make it all work. So yeah, you're right. If I can do it, anybody can. That's kind of how I've always approached it.
00:58:46
Speaker
And I totally, I totally feel the same way about financing the stuff that I love doing. I like writing essays. And so I try to, I've published a few and I want to do more of that. And there's also ways within content to do things that you care about. I worked for a publication for a while that was actually produced by a bank, but it was all about curiosity. And I wrote some fabulous, the interesting and heartwarming stories about
00:59:16
Speaker
service dogs and peanut allergies and some really good stuff. It's content. I've grown some work for Fidelity Charitable about giving to nonprofits and how to make that happen, highlighting some of their nonprofits. I also just got probably going to get a gig working for a nonprofit redoing their website and it's well-paying too.
00:59:41
Speaker
Even if it's called content and working for companies, there's still meaningful work out there in corporations, corporations that are doing good work or stories about that. There's a lot of ways to do stuff that's meaningful in content, either by subsidizing it or finding the opportunities directly in content that can do that.
01:00:04
Speaker
And there's something that struck me too about the book that I really, really liked. And you've alluded to this several times throughout the conversation too, is that, but you wrote this down as a more concrete monthly thing. And it was just a goal of doing one thing to help another writer out per month. And when did that come to you? And how important is that to you as just as a person, but also as a member of a community trying to make their living, you know, generating words?
01:00:35
Speaker
I wouldn't be here today if it wasn't for other writers. I owe my success completely to other people that have helped me out, given me leads, given me advice, listened to me. And so, you know, we're not each other's competition, we're each other's colleagues. And I think that the more you think of it that way, the more successful you can be because you really create a community.
01:01:04
Speaker
I'm not in competition with you even if we're in the same niche because your perfect client is very different than my perfect client. For example, I just got a gig doing some copywriting and halfway through it, I realized that I'm not the right writer for it. It's a different tone that I'm used to. It's just coming out very forced. I'm doing an okay job, but my friend Stephanie would be absolutely perfect at it. As soon as I finish this,
01:01:33
Speaker
project, I'm going to refer it to her. And she has done the same to me when she gets in a project where it's much more tech-oriented than she is, so refer it to me. I just think the more you view it as a community and more you view writers as colleagues,
01:01:49
Speaker
the better the whole community is and the better you are. I kind of view life as a big pot. Your goal is to put in, sometimes you put things in the pot when you're helping people and sometimes you take it out and we should all aim to, at the end of our time on this earth, have put more in than we take out. So that's kind of how I view it with helping other writers.
01:02:11
Speaker
And I think we've covered kind of how to go zero to one, but what if you're starting to get traction? What are some of those next steps that someone can go from one to 10 and then from 10 to 100 from there and really start ratcheting? So once you've got some traction, you kind of need to look at it like a stair step. So you need to get to the next level, but you need to figure out what you need to get to get to the next level. So is it different clips?
01:02:41
Speaker
Um, is it better clips? Is it more experienced? Um, so sometimes you need to get other clips and I like to use the double niche trick, which is where you use an outlet that you're currently writing for. Let's say you're writing for a retail publication and you want to get into, um, some retail tech or in tech in general. So you start pitching some, um, retail tech stories and then use those stories to get, um, different clients.
01:03:10
Speaker
So that's a big trick that I, um, tricks, not the right word, but strategy kind of, if you're at the, the 10 trying to move up, you also have to be willing to drop clients. It's kind of get a higher paying client, drop a lower and it's a stair stop. It's moving up and you have to do it all. It all is fluid. Um, so I recommend when people are at the 10 trying to move up, take a firm look at where you are. Um, I tell people to make a list of their clients.
01:03:38
Speaker
figure out what percentage of the income they are, the hourly rate you're earning with that client, and then give them a pain in the wet rating, because that factors in as well. And then once you have that written out, you can see kind of who's the lower pain and the higher pain, and that will be your first to go. So I recommend kind of a systematic way of looking at it.
01:04:07
Speaker
And as you're pitching these businesses, I think it probably is good to be clear about this too because for journalists, it's usually you're pitching a magazine, an idea you have that you think is a good fit. And I think oftentimes what you're doing with LOIs is you're saying, I have something of value to offer you guys if you have
01:04:29
Speaker
if you need content written for the products you have or services you offer. So it's almost kind of, it's a different way. You're not pitching maybe some of the relationships you have. You do say, hey, this might be a good idea for you, but are they coming to you with ideas that they want written about or do you go to them with ideas too? When you're approaching a potential client cold, the LOI is selling yourself, not an idea.
01:04:58
Speaker
So that's a big difference with journalism is you're pitching, you're selling yourself in content marketing. In journalism, you're selling an idea. And now that a client wouldn't have a relationship with a client, sometimes they'll say, hey, we want to do something around cybersecurity because October is cybersecurity month, you got some ideas and I'll throw a few things in email. But you're not going to approach a content marketing agency and send them some ideas because you have no idea what clients they,
01:05:27
Speaker
they need writers for or what topics they're looking for. So you're selling yourself. Right. Right. And what's still like, where does, you know, when do you feel most engaged in, in the process and feel most alive when you're, so yeah, when, when do you feel most alive and engaged in your work?
01:05:50
Speaker
I think it's doing some of the content strategy. I've had some projects where I've been able to be involved with coming up with the content campaigns and the strategy and the editorial calendars.
01:06:02
Speaker
trying to figure out what's gonna help solve people's problems and some unique and interesting ways to do it. So it's, for me, it's the strategy. The other thing I feel the most alive is helping other writers. I do free coaching calls for anyone that needs help. I don't sell anything to writers other than the book. So I feel very alive when somebody emails me and tells me that because of our caller and email I send them or something on my Facebook group, they just landed an anchor client
01:06:32
Speaker
for $2,000 every month. I mean, that's the biggest high for me, to be honest. That's great. So where is, or what's the name of the Facebook group? The freelance content marketing writer. Very creative. That just so happens to be the title of the book, too. And you know, it's kind of funny. Every now and then you make a decision that's right. That's what I called my blog as well. And because I picked that back in 2013,
01:07:02
Speaker
And I kind of had SEO in mind, but I'm one of the top websites for the search term content marketing writer because of the blog title. So that one move changed my career because I get a lot of people that find me through Google, which is kind of rare for writers. I get probably four to eight cold inquiries from clients a month either through LinkedIn or through my blog.
01:07:29
Speaker
Very nice. Very nice. And where can people find you online as well as if they want to get more familiar with you and your work and your social platforms, et cetera? It's jennifercraggeryfrider.com backslash blog. Fantastic.
01:07:50
Speaker
Well, I think, is there anything else that, is there something we didn't talk about that you feel like we should really hammer on or do you feel like we touched all the bases? I had one more thing. My very nice people rule. I think that has been a big key for me and it's resonated with a lot of writers. So I don't consider my career in terms of, you know, successes being how much I've made or my clients
01:08:20
Speaker
Except maybe the six figures, that was kind of cool. But it's really the three stages. The first was when I got a little bit of success, I instituted what I called the no asshole rule, where I wasn't going to work with anyone that was a, you know what? And actively would say no to clients and started screening clients. I think that's a big turning point when you start actively deciding, do I want to work with this person? And then when I got a little bit more success, I instituted the nice person rule.
01:08:50
Speaker
Um, which was the second stage, I would only work with nice people because there's a pretty big difference between someone just not being an asshole and someone being nice. So the second stage was working with nice people. And about two years ago, I hit the ultimate. I only work with very nice people and the way that I screen them, it's kind of funny. You have to figure out what works for you. But.
01:09:12
Speaker
I always talk to potential clients on the phone and I tell them on the phone that I only work with very nice people and someone that doesn't fit that category doesn't really know what to do with that and they're kind of uncomfortable, but the type of client that I'm going to do well with starts cracking up and says, oh my gosh, I have the same rule or I need to start the same rule or that's why I'm talking to you to make sure you're not a jerk. So for me, that's been the key and maybe you're
01:09:41
Speaker
your test, quote unquote, isn't the nice people, very nice people. Maybe it's something else, but it's really figuring out how to screen the clients for yourself.
01:09:50
Speaker
That's great. Well, Jennifer, this has, I think, been a really enlightening conversation, certainly for me and hopefully by extension, the people who tune into this show who are often writers of a certain level trying to get some degree of traction, whether that's through essays or memoir or
01:10:13
Speaker
reported journalism, like maybe this will give them another inspiration to subsidize other things that they like to do or maybe it'll be a way that they can finally create a life and really manufacture a life that's worth living, give them more freedom to do the things that they love. So I think everything you've done is a great service to that and a great service to the community of writers on the whole. So I just thank you for all the work you do and thank you for coming on the show.
01:10:43
Speaker
Thank you so much. It's been a pleasure. I really appreciate the opportunity. Fantastic. Well, thanks so much, Jennifer. And we'll be in touch for sure.
01:10:52
Speaker
That was fun, wasn't it? Right? I think it was. Thanks for listening, friends. Don't forget to consider leaving an honest and helpful review over on Apple Podcasts. They make all the difference. If you feel like reaching out, I'm on Twitter, at Brendan O'Mara and at CNF Pod. Also on Instagram, Brendan O'Mara.
01:11:15
Speaker
If you visit BrendanOmero.com you can find out how to email me, if you so care to, and sign up for my monthly email newsletter where I send out book recommendations for the month, a pretty photograph I took, or a blackout poem.
01:11:34
Speaker
And what you might have missed from the world of the podcast, yeah. Once a month, no spam. Can't beat that. And ask yourself this question before you peace out. What if you gave it everything you've got? I mean, everything. Okay, I'm out. I'm gonna go give it everything, man. Everything. See ya.