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Kaleigh Moore: Reflections on her 10-year freelance career · Content, Briefly

• 0:00
  [gentle music] This episode of Content Briefly is brought to you by our friends at Editor Ninja.
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• 0:37
  [gentle music] That is kind of the definition of a pro freelancer versus the person who just says, "Hey, here's my portfolio." Yeah.
• 0:47
  How well do you know your audience, and how easy are you making it for them to hire you? It's this humanity aspect of it, of like- Yeah...
• 0:54
  can you take the 10 extra seconds to write the little blurb and make it very custom? Because that is often the difference between who gets hired and who doesn't. [gentle music] Hey, everyone.
• 1:07
  Thanks so much for tuning in to another episode of Content Briefly. Today, I'm talking to Kaylee Moore. She's a really well-known freelancer.
• 1:13
  Regular listeners know we don't do a ton of freelance talk on this podcast, but I saw on Twitter that Kaylee was just celebrating her 10-year anniversary of freelancing, and she's built a really impressive career of freelance writing.
• 1:26
  She sells products. She's built courses. She has two podcasts. She does speaking gigs.
• 1:31
  She does some reflecting on things she's learned over the last 10 years, things she's currently excited about, stuff she's hoping for the future, and I thought it was a really cool and interesting conversation.
• 1:41
  This is kinda the other side of content marketing, and also many of us have freelancing side gigs, and a ton of people in Superpath also are pursuing freelance careers. So there's a lot to be learned here.
• 1:51
  Really interesting conversation. I enjoyed it, and I hope you do, too. Also, just a quick reminder to check out the new and improved Superpath Slack group. It's now 20 bucks a month. You can also get an annual discount.
• 2:03
  Your employer should probably cover it for you since it definitely counts as professional development. And I think what you'll find there is gonna be really exciting.
• 2:09
  There's some really interesting high-level strategy discussions, in-depth conversations on things like people management and career development. Honestly, it's awesome. I'm enjoying being in there more than ever.
• 2:19
  I think you will too. If you wanna check it out, just go to superpath.co/community and sign up there. [gentle music] Hey, everybody. Jimmy from Superpath here today with a cool episode.
• 2:32
  We're talking to Kaylee Moore, freelancer extraordinaire.
• 2:35
  I bet a lot of folks are already familiar with her work, social stuff, but maybe, Kaylee, could you just give yourself an introduction for anyone who doesn't already know you? Yeah. Happy to.
• 2:46
  So I have been a full-time freelance writer for 10 years now. I just had my 10-year anniversary this month. It's November of 2023, if you're listening at a different time.
• 2:54
  I mostly work with software as a service companies, kind of in the e-commerce ecosystem. So think, like, Shopify, BigCommerce, the platforms for e-commerce, and then the tools that integrate with them.
• 3:05
  So, like, email marketing tools and all those extensions that go along and can tie in on the back end of an e-commerce store.
• 3:13
  So I have been working on the content side of those operations, usually super long-form educational blog posts with some variance in the mix. That's kind of been my primary focus, though.
• 3:24
  I've really niched down over the last...
• 3:26
  I would say six or seven years ago, I decided to really hone my focus in on that area, and it was the right place at the right time for sure, but it's been wild the past couple of years since the pandemic and the economy and everything.
• 3:39
  So I'm sure we'll talk more about that. But 10 years, been doing it. That's awesome. Well, congratulations. I mean, that's really an achievement. Thank you. My freelance career lasted about two and a half months.
• 3:49
  [laughs] What were you doing? What happened? Let's hear that story. It really didn't go very well.
• 3:54
  [laughs] I was working at this SAS company called Vero, and it was going really well, and I was like, "I'm gonna go out on my own and do this style of content for other companies," and I think that I didn't plan it very well.
• 4:09
  [laughs] And basically what happened was I actually did go out and book a bunch of work, but I so quickly became miserable by the whole thing because I was working so much trying to keep up with these retainers that I had sold.
• 4:23
  Uh, liter- I literally burned myself out in, like, a couple weeks. That'll do it. Like, I can't keep doing this. Mm-hmm. If I were to do it again, what I would wanna do is do it like you've done it.
• 4:31
  [laughs] And maybe that's a good place to start because you're well-known as a freelance writer, but you have other things going, too. I mean, you sell templates, courses. You have two podcasts. You do speaking gigs.
• 4:44
  Could you talk a little bit about the variety of things you do? And I'm curious, related to that, how has it affected your career as a whole?
• 4:51
  Like, has it made it feel more sustainable or interesting to have a couple things going? Short answer, yes. Long answer is I'm somebody who really values novelty. I'm not good at doing one thing for a long time.
• 5:03
  Even if I'm quite good at it, I really need that variance to keep my day-to-day interesting, otherwise I will burn out or I'll get bored or I'll start resenting the work, and then it's not fun anymore.
• 5:12
  So I just throw a lot of spaghetti at the wall, and I always have, and I've found that it works really well for me.
• 5:18
  Most of the experiments that I've tried as far as digital products, co-launching a course for freelancers with Paul Jarvis many years ago, trying things with these new podcasts, it's to give me some creative outlets because, like I said, I'm very good at the work I do.
• 5:33
  I get hired over and over again. I know exactly how to do it. It's kind of broken down into a science now.
• 5:37
  But I need those little things to keep things interesting and to get me out of the house, too, to be totally honest. I mean- Sure...
• 5:45
  the speaking engagements and stuff like that, going to conferences, the journalism w- work I do, writing for Forbes about retail and e-commerce, I'm still pulling from the foundation of knowledge that I have from my client work, but I get to talk to people, and I get to get out in the world more.
• 6:01
  Of course, it's authority building, and it's building ethos for me as an individual and all of those good things, but for me, the primary focus is it gets me out of the house because as much as I love this office-I gotta get out of here sometimes.
• 6:12
  10 years is a long time to spend by yourself. I hear you. It's been necessity, for sure. I hear you. It's interesting, actually. I just hit my 10-year anniversary of working remotely just a few days ago, actually. Oh.
• 6:25
  You get it, then. You know, remote working is different today than it was 10 years ago.
• 6:29
  I mean, obviously, but it's really different even than what it was in 2019, and the first thing I did, like the first day I worked remotely, I realized I gotta get a dog. [laughs] Mm-hmm. Or I'm gonna go insane.
• 6:41
  So we got a dog, and she's about to turn 10 years old here pretty soon. Aw. 10 years came and went just like that, you know? Yes. It goes so fast. Exact same for me.
• 6:50
  I got a dog one year in, so he's nine, and yes, he gets me outside. I have to take him for a walk. Yeah. Otherwise, I would just be in front of this computer all day, so. Totally. Totally. High five to that. Yeah.
• 7:00
  [laughs] Yeah. You know, one other thing I'm curious about, you have 64,000 Twitter followers. That's a lot. I mean, there's a lot of people who follow you and follow your work. How intentional is that?
• 7:09
  You know, like how much time and effort have you invested in, I don't love the word personal brand, but, you know, like building up that audience of people for the purposes of furthering your career or just having fun with it, too?
• 7:22
  Yeah. I would say three or four years ago, I was being very strategic about really finding my lane with, I'm gonna just talk about this one type of subject matter, which was, of course, writing related, 'cause that's...
• 7:33
  I was just trying to build my presence as like, hey, here's a writer. And then again, hopefully that will lead to work. Hopefully that will help me sell info products, all of those things.
• 7:41
  I would say since then, though, you know, that really did help me build the following up there, and Twitter's different now. It's definitely not the same environment anymore.
• 7:49
  So I think I've kind of shifted back to how I originally used Twitter, which was just kind of a water cooler throughout the day, a place to check in in between writing sprints and things like that where I can share things I'm thinking about, go back and forth with people.
• 8:03
  Again, I think the virtual water cooler is the best metaphor here because if you're spending that much time in front of the computer and you're home alone all day, you need some human interaction, and for me, that's been a really good place to have that sort of community building type of thing.
• 8:16
  For sure. I hope that Twitter can get back to those roots at some point because [laughs] it's gotten to be so contentious. Yes.
• 8:24
  You know, and I miss the days of Twitter, which were, like not that long ago, where it's just, like people, like you said, just, like checking in throughout the day. Mm-hmm. A little distraction from work.
• 8:32
  I agree, though. It's still there.
• 8:33
  Like, you're one of the people I really enjoy following, and there's, there are still, like a few others that treat Twitter in a way that where it's like, this is actually just genuinely interesting, not...
• 8:42
  You don't, like get the sense that they're, like on a mission to promote stuff- Yeah... or out there to argue with people or whatever. Yes, yes. I see a lot of both. Yeah.
• 8:49
  I'm guilty of the promotional stuff, too, because, you know, that's part of it. That's part of the whole thing. I just try to keep it a good mix these days of like- Sure...
• 8:56
  here's something I read that I thought was interesting, or I just watched this documentary. Here's what I took from it.
• 9:01
  Things like that, where I'm like, you know, screaming into the void a little bit, but also, sometimes it sparks some nice conversation, and then I get some positive pellets that keep me alive as a human being.
• 9:10
  Yeah, yeah, totally. Your social has a very calm aesthetic. Oh, thank you. It's a lot of, like autumn scenes. Yes. Cute dogs. [laughs] E- e- even, even, like pictures from your office, which is very nice.
• 9:23
  It's like- Yeah, very cozy. It's cool. I like it. The vibes are good. Yeah, totally, totally. But actually, [laughs] whenever I see you post pictures, stuff, I'm like, "I wish my life was that calm."
• 9:30
  [laughs] Don't be confused. It's all a facade. It's not calm over here at all. Yeah. That's so funny. [laughs] I am curious. I wanted to ask you more about the niching down. Yes.
• 9:40
  How important to your career has that been, and is that... Do you think it's fair to offer kind of generalized advice that all freelancers should niche down, or is it not that simple? Nothing is ever that simple.
• 9:51
  The answer is always it depends, and that's my new rule and outlook on life for all things moving forward. With that said, I will say it served me very well. I think there was a lot of good timing on my side, though. Mm.
• 10:03
  So I happened to get hired by a software company who was in this little niche that I, you know, just happened to fall into through Twitter, a Twitter conversation that then snowballed into a friendship that then turned into a working relationship.
• 10:16
  So I fell into this software as a service space 10 years ago when it was very different and kind of this emerging thing, nothing like it is now, where there's tons of venture capital, lots of money to be spent.
• 10:27
  So it was really, really good timing for me.
• 10:30
  I also found that I understood the technical subject matter, and it was work that I enjoyed doing, and I, I just kind of understood the landscape in a way that it clicked in for me in a big way, and I don't think that that happens for everybody.
• 10:43
  I think sometimes people get into it, and they're like, "Ugh, this is so boring. I hate writing about this."
• 10:47
  Or they get into it, and they find that it's hard to make connections because it is a fairly established space now.
• 10:54
  So I think that there is a benefit to having a niche as far as even just a bucket of type of work that you do, whether you focus on email marketing or website copy or writing paid search ads, whatever it is.
• 11:06
  That, I think, is good as far as it helps you build your expertise. You know, you're s- not starting from scratch every time you start a new job.
• 11:13
  You have a foundation of knowledge that then you can build upon, so there's that benefit, but then having an industry niche as well, it's kind of the foundational knowledge thing.
• 11:21
  You're not having to go out and read hundreds and hundreds of articles to get up to speed on something. You're comfortable in the space already. You know the vernacular.
• 11:30
  You can do it, and it's not so difficult every time you get a new assignment. So I think it's kind of an efficiency thing, if nothing else. But again, I started my career doing a lot of different jobs.
• 11:40
  I pretty much took anything that came my way, and so that range of experience of doing a lot of different things helped me figure out what I didn't like doing, and I think, if nothing else, that was the most useful outcome of that activity, of helping me figure out what I didn't like, what I wasn't good at, and what didn't pay well.
• 11:56
  Yeah. That's interesting.
• 11:58
  I wonder, too-If this has happened to you where the people that hire you are also in this space, and they may over the years bounce around from one company to another, but also in the same industry, and when they need content, they're like, "Oh, let's call Kaley."
• 12:12
  Yes. That happens even today. And so having that network is super, super helpful. It's a good referral engine for the business. It keeps things coming back.
• 12:19
  And even if it's not a good fit, then I can pass it on to somebody else who maybe is getting started.
• 12:24
  If they're more in startup mode, the company that's reached out, they need somebody who's a little bit less expensive, I can say, "Okay, well, this isn't a fit for me, but I know somebody who's a little bit more junior and would be great for this."
• 12:35
  So again, it's nice to be able to, to return the favor as well, kind of on my end of the equation. Yeah, yeah. You know, actually that makes me think of something that I wanted to ask you, which was subcontracting.
• 12:45
  Do you ever do that? And also, have you ever thought about creating an agency that specializes in content for kinda like D2C and retail? Yeah. So I've thought about it.
• 12:54
  I think the idea of building a full-on agency is pretty intimidating to me. And again, my roots are with Paul Jarvis- Yeah, yeah... who's got this whole mentality of like company of one, right?
• 13:02
  And that's always been very appealing to me. I'm very independent. I do well on my own. That said, I am good at delegating pieces of my process that I either am not good at or don't super enjoy.
• 13:14
  So I do use subcontractors. They do help me.
• 13:17
  And, and when my business gets really busy, I have overflow projects, so then I do use subcontractors to help me, again, just make sure that everything's getting done, or it's good cover if I get sick.
• 13:27
  I, I tend to get sick a lot, so if I suddenly fall ill, this is a good cover mechanism for me to not have to put the full brakes on with my business.
• 13:36
  So having that network of fellow freelancers has been really, really beneficial for a lot of reasons. But as far as building a full-on agency, I just don't think that's it for me. I don't have the energy or the interest.
• 13:47
  Could I do it? Probably. But I don't know, I just, I don't think that's it for me. And I think that that's a knowing yourself thing. Totally. You know? Some people are like, "Yeah, let's do it."
• 13:55
  And I think for me it's that if it's not a hell yeah, it's a no. And it's always been a hell no. Yeah. [laughs] Absolutely no. No, thank you. I think it's great you recognize that.
• 14:03
  Having worked at agencies before, [laughs] they're very difficult work environments. Yes. Yeah.
• 14:08
  One of the beautiful things about a freelance career is, especially as you become more established, you have a lot more control over your schedule and your calendar, and like you just throw all that right out the door if you go the agency route.
• 14:19
  For sure. It's chaotic. Yeah. One thing I've noticed about content marketers in general, and freelance writers specifically, is that the career tracks are not particularly well defined. Hmm.
• 14:31
  And I think for in-house content marketers, they hit this point five to seven years into their career where they say, "Where is this going? Am I trying to become a marketing leader?
• 14:44
  Like, do I wanna become a marketing director or VP of marketing? Okay, well, I better start learning some other channels, not just content." Mm-hmm. Or they say, "Product marketers make more money than content marketers.
• 14:53
  Like, maybe I should take the skills I have here and add some new ones and go that direction instead," or, you know, whatever. They kinda like are faced with this feeling of like, "Oh, I'm gonna work for a long time.
• 15:04
  Is this the thing for me?" Yeah.
• 15:06
  And I feel like there's a freelance version of that as well, where for some folks, maybe the vision is you build up enough inbound interest and then you say, "Okay, I'm gonna start subcontracting, then I'm gonna turn that into an agency."
• 15:18
  For some folks, and I really appreciate your perspective on this, you've said, "That's not what I want. There's other ways I can handle the demand though," right?
• 15:26
  And it seems like for you, partially that's been selling info products. Mm-hmm. Yeah, I think you run two podcasts now. Which don't really make money, but [laughs] But certainly- It's fun...
• 15:34
  it could potentially, I would imagine, right? Yeah Like, if you attract enough people to them.
• 15:38
  Now I'm curious, as you got to that point in your career, like at whatever point it was when you said like, "Maybe I'd not, I'm not just gonna write for the rest of my life," like how you started thinking about like what other things you might do to- Yeah...
• 15:51
  supplement income, but also, like you said, kinda tap into the novelty of some new stuff. Yeah. That's where I'm at now. You know, I'm 10 years in. I'm at this point where I'm like, "I don't know if this is it anymore.
• 16:02
  Just because I'm good at it, should I keep doing it?" I don't know that the answer is yes. So I'm at that point where I'm thinking, "Okay, I really enjoy teaching. I enjoy the education process.
• 16:12
  I get a lot from it emotionally, mentally." So I've been opening up one-to-one coaching sessions, and I'm considering doing like a cohort based thing.
• 16:21
  I'm a little hesitant, because that comes with the sales aspect of all that, and I really don't love selling. I don't, I don't like selling things.
• 16:28
  So the other thing too is kind of going in and doing private group sessions, doing consulting work, things like that.
• 16:34
  The other thing I've become really curious about lately is kind of like a head of content role, even in a freelance or independent contractor context.
• 16:42
  I know how to do it well, and I know that companies maybe don't need a full-time in-house person within their marketing department, but maybe they're looking for somebody to manage the team of freelancers and do the creative briefs and do the editing and things like that, that I feel like my skillset is really well-suited to.
• 16:59
  So that's where I'm at right now of considering, is this the next move for me? Do I wanna take a short-term job maybe with a company who wants me to come on site for several weeks in a row, something like that?
• 17:11
  I don't know.
• 17:11
  I'm, I'm keeping the door open right now, and I sent a newsletter out probably about a month ago at this point where I was kind of talking through this and just being candid about 10 years is a long time to do one thing.
• 17:22
  I think it's time for me to think about what's next. I don't know what that is, but here are some things that I'm thinking about.
• 17:27
  And I'm still waiting for it all to shake out, but it's been interesting to keep the door open and to not be quite so busy all the time and give myself some time and space to figure out what is next, because I still don't know.
• 17:38
  Yeah. That's cool. I mean, the freedom and flexibility is, that's it, right? Right. It sounds like you're good at setting boundaries for your work. Yes.
• 17:45
  Which was one of the reasons that my freelance career didn't last very long. Like, I didn't really know how to set boundaries. I didn't really, in retrospect, know what I even wanted out of this. Sure.
• 17:57
  Just like I just wanna book clients and see if it works, and it didn't. It wasn't deliberate enough. Has the setting boundaries-... part been difficult for you?
• 18:04
  Like taking a vacation, closing your computer at the end of the day. Like, have you figured that out? Is it still occasionally a challenge? I'm getting better at it.
• 18:11
  There was a, when I first started the business, I mean, I was butt in chair from 7:00 to 5:00 every day, and I was coming out of working a traditional 9:00 to 5:00 job too.
• 18:21
  So I thought that that's what I had to do, and I wouldn't allow myself to enjoy the freedom and flexibility that freelancing provides.
• 18:28
  And so as I've gotten a little bit better at letting go some and enforcing those boundaries more, more consistently, I have been able to step away and, and travel and adjust my work week from full five days a week to sometimes four or sometimes three during the summer if it's really nice out.
• 18:45
  And again, that often means making less money or saying no to things that could be potentially very cool, but it's been really good for me because, like I said, I get sick a lot.
• 18:54
  I feel like if I overdo it, my body starts to shut down, and they're like, "No, no, no, that's enough." So- Yeah...
• 19:00
  I've had to just kind of listen and follow the ebbs and flows of my own energy levels and what I wanna do with my life.
• 19:07
  I feel like I spent the first five years of my business totally pushing those things to the side and just putting everything I had into the business, and I got to that point you talked about where I was totally burnt out, not having a good time, did not enjoy the work, and I thought, "I've got to do something differently."
• 19:23
  So that's when the shift happened, and I had to start having some of those uncomfortable conversations about, okay, I'm not available on this day, and I'm not taking calls on Mondays and Fridays, and things like that.
• 19:33
  Yeah, yeah. So just baby steps in the right direction. Are you a reflective person? Like, do you like journal or something?
• 19:38
  Like, I find that in my brain, I'm like, "I know I should set better boundaries," but I find, like, the only way that I can kind of clarify the thoughts and then make a plan is I'll journal about it, and then whatever.
• 19:49
  Use it to, like, block time out on my calendar. Like, it has to be, like, so specific for me, or else I- Yes... just continue working and can't stop. [laughs] Yes. I wish I was a better journaler. I'm not.
• 20:00
  You know, you would think as a writer that would be a natural activity for me, but I don't know. I just can't get myself to do it.
• 20:05
  So I do go to a lot of therapy, and that's where these conversations come up of, "Hey, why are you so unhappy? Why are you chained to your desk?
• 20:12
  And why are you so desperately tied to the number that you're making every month?"
• 20:16
  Things like that, where I have to think more deeply and have a conversation with an external third party who's saying, "Hey, stop doing this. It's not working." That's been helpful, too. Yeah, yeah. Totally.
• 20:25
  Therapy's the best. It is. One thing that's happened in the Superpath community, which has been unexpected and very interesting, is that a lot of freelancers have joined.
• 20:36
  Interestingly, you were the first AMA we ever did in the Slack group, and this was, like, maybe fall 2020. Like, it was a long time ago now. Yes, it was.
• 20:45
  We've had a lot of freelancers join, mostly because we've been mentioned in a couple blog posts or other communities where people are talking about, like, places to find work. Mm-hmm.
• 20:55
  And people post gigs in our community all the time, so we have tons of freelancers. But then they stick around, and they have questions.
• 21:01
  And they talk about freelance stuff, and I feel very unqualified to help these people because I don't [laughs] really know. You know what I mean?
• 21:08
  And so, like, from time to time, we try to bring in a really experienced freelancer to do an AMA. You know, we've had a couple on the podcast now.
• 21:15
  So this is sort of broad, but, like, what do you tell folks who are freelancing right now who have had a tough 2023? 'Cause it's, it seems like there's a lot of them.
• 21:23
  The, I don't have data for this, but, like, 2023, I think we all agree has been, like, a pretty crazy and challenging year.
• 21:29
  Like, every now and then, you know, we hire freelancers for things, and I'll put up a, an ad on our job board, and I'll get 1,000 people. Wow. It's crazy.
• 21:36
  And then I'm like, I don't even know how to begin sorting through applications for that many people.
• 21:41
  Anyways, this is, like, a huge build-up to a simple question, which is like, what are you recommending to folks that you coach?
• 21:47
  Like, without giving away too much of the secret sauce, is it really just about, like, there's a couple best practices, and you have to, like, do good work and build a great reputation, or is there, is there other stuff there?
• 21:57
  I'll be totally honest. Even this year, being 10 years into this business, super well established, lots of connections, it's been a rough year for me too. And I have a, another friend, Emma Sammasko.
• 22:07
  She's my co-host for the Freelance Writing Coach podcast. She had her second child. She's trying to come back, and she's like, "Man, I picked the wrong year to try to come back into this industry." It's a wave, you know.
• 22:18
  It's always got its ups and downs, and it feels like we've been in a down for a while, and that's just part of the process. So- Yeah...
• 22:24
  I think my best practices that I tell people is leverage your existing network, reach out to people and tell them that you're available for work.
• 22:32
  Sometimes they just need a little nudge or reminder that you're still offering these services and that you have availability. So that is a simple solution to the problem.
• 22:40
  Most of the time, if you do that, you'll get at least one response or an introduction to somebody through a mutual connection. That has always served me very well. And then being very proactive, too.
• 22:49
  So reaching out to people that maybe you haven't worked with in a while, but you did in the past, and checking in and saying, "Hey, you know, I don't know if you need any help right now, but I'm available if so."
• 22:58
  Just doing little things like that can go a long way. Otherwise, it's a lot of kind of sitting tight and waiting till things get better. I would say year-end is always the toughest time, too.
• 23:07
  You know, we're in this right now when we're recording this, and things kind of wind down in certain industries at a certain point towards the end of the year because the holidays are coming, everybody's gearing up for the next quarter, and then they'll do a heavy focus moving forward in the new year.
• 23:21
  But it's a tough time right now.
• 23:23
  So just kind of getting comfortable with being a little uncomfortable is my best advice, and then being as proactive as you can with reaching out to people who you have some sort of existing relationship and using that as a springboard.
• 23:34
  It's kind of duh advice, but it, it seems to work. Yeah. Totally.
• 23:38
  Superpath has probably hired 40 freelancers this year, and I have a number of those folks who check in now and then and just say, "Hey, you know, just checking in. How's everything going?"
• 23:48
  Just like you said, like, "I have some availability coming up. If you have a project, let me know." And if I have something... Actually, this actually literally just happened last week.
• 23:55
  I was like, "Actually, I do have something. [laughs] Let's do this." Often, I'll just say, like, "I don't have anything right now, but please do keep checking in," and I mean that.
• 24:02
  Like, I want you to keep checking in- Yes... because it's actually quite helpful for me. I would prefer that you check in, rather than me being like, "Oh, I need a writer. I guess I'll start from scratch." Yeah.
• 24:11
  You want the person who's proactively raising their hand and saying, "Hey, I'm here if you need me," because you may have a moment where you need something, and then they're the person that's top of mind.
• 24:19
  And that's how we end up hiring people. You know, who's top of mind? It's often as simple as that. Totally.
• 24:25
  There is one other thing that I have noticed in reviewing a lot of job applications this year, which isSome people take their writing samples/portfolio very seriously, and it's very easy to tell when someone takes it seriously, and it's also very easy to tell when they don't.
• 24:42
  Okay. Just as an example, any time we're looking for writers, I'll say, "Please send me three writing samples", and I'll say, "They have to be live URLs on an actual website. Please give me one sentence on this article.
• 24:55
  Just tell me literally anything about it." [laughs] You know, like- Sure... was it your idea? Did you work with an editor? Did it perform well? Just literally any context is helpful.
• 25:04
  And it's interesting and kind of frustrating how many people will just leave in that field, "Here's my portfolio link". Yeah. Or, "Here's a Google Doc," or, "Here's a PDF." I'm like, "No".
• 25:15
  You have to understand, like, I'm gonna go through 1,000 of these. Make my life a little bit easier. Yeah. So I am curious, this is building up to a question about how do you showcase your work? Yeah.
• 25:23
  You know, I feel like this is actually like a fundamental challenge for freelancers, because the better you showcase it and the more of a reputation you build around it, I'd imagine, the easier it's gonna be to showcase that and get yourself hired based on previous good stuff you've done.
• 25:36
  I'm not a portfolio girl. Honestly, I do everything case by case because I do want it to be custom. Interesting. And I want it to be relevant to the person that I'm talking to.
• 25:45
  And even though I'm very niched down and have this specific focus, if I have a company with a specific type of software o- offering, and I've worked with a similar company before, maybe even a competitor, I wanna send them samples that show that I know their subject matter very deeply.
• 26:00
  And so I'm never gonna send them this portfolio full of things within this entire software as a service industry.
• 26:05
  I want it to be highly, highly specific and relevant to their s- individual context that they're coming to me from.
• 26:12
  I wanna show that I have subject matter expertise, and again, I'm gonna provide a little blurb on each one of like, "Hey, I pitched this idea because when I was writing for Forbes on this topic, I saw that there was a trend.
• 26:22
  I connect the dots, you know, bringing the readers from point A to point B and illustrating the trend here. I'd like to do something similar with you."
• 26:29
  And again, that is kind of the definition of a pro freelancer versus the person who just says, "Hey, here's my portfolio". Yeah. How well do you know your audience, and how easy are you making it for them to hire you?
• 26:41
  It's this humanity aspect of it, of like- Yeah... can you take the 10 extra seconds to write the little blurb and make it very custom? Because that is often the difference between who gets hired and who doesn't.
• 26:52
  Absolutely. Absolutely. I actually just recently had someone, a freelancer, email me and say something to the effect of like, "Hey, I wrote this piece for a customer" and, like, gave me a little overview of what it was.
• 27:03
  Like, "I could do the same type of thing for Superpath and for one of the customers you work with." And I was like, "Dang, that's good. I want that." Yes.
• 27:09
  It was proof to me that this person was, like, thinking just so much more deeply- Mm-hmm... about the work than just, you know, here, this article is ranking for this keyword.
• 27:17
  You know, it was kinda like, here's, like, a really different take on a topic, and like, I could bring a similar s- flavor of... And I was like, "Yeah, yeah, that's great. Give me that. I like that." Yes.
• 27:25
  That's always been the recipe for success with my business, I will say that. So even with Paul Jarvis, perfect example. He had a course for freelancers.
• 27:32
  I took the course, but I thought that there were some things that I had learned from my own freelancing journey that would've been really helpful, and it improved the course and take it to the next level.
• 27:40
  So I sat down and I wrote him an email and I said, "Hey, I took the course. I loved it. I have some ideas on how we can make it better. I wanna help you do that. Here's my plan of action. What do you think?"
• 27:49
  And he said, "Absolutely. Let's do it." Yeah. [laughs] That's awesome. And so he brought me on as a creative partner. We've revamped the course, made a V2 of it, and it was wonderful. You know?
• 27:58
  It just took the whole thing to the next level. He had a partner in creating this, so it wasn't this huge undertaking for him. He had somebody who was in the shoes of a freelancer day to day, so important perspective.
• 28:08
  Again, just packaged it up really nicely, put a bow on it and said, "Hey, I have this idea. I can help you do it. Here's how. Let's do it." And he's like, "Okay, yes." [laughs] That's awesome.
• 28:17
  It sounds like you're very good at sales. Maybe you should start an agency. [laughs] Maybe. I don't know. I don't know.
• 28:24
  I do wonder about that because I feel like cold outreach gets, like, a bad rap because there's so much junk out there, but honestly, if you do some good work, and you send it around to people in your network and say like, "Hey, I'm available," like- Yeah...
• 28:37
  that's such an easy yes. If for nothing else to be like, "Okay," like, "I'll pass it around to a few other people." Yes. When the time arises, I'll reach out, or like that stuff really does go- Mm-hmm...
• 28:45
  a very, very long way. Absolutely. I noticed on your website that you are very clear with people about your rates and how you work. Mm-hmm.
• 28:52
  Like, anyone can go to your website and see exactly what you charge and exactly how you engage with companies. First of all, that seems like a great idea. Like, you just say like, "I charge this much.
• 29:02
  Don't waste my time if you don't wanna pay this much. Also, there's like a monthly minimum." Mm-hmm. You get one round of edits. I guess my question is, do you ever get pushback on that?
• 29:10
  Or has that really helped people self-select? Yes.
• 29:13
  It's a great filtering mechanism if nothing else because I used to spend a lot of time on the phone with these prospecting calls of, "Okay, well, you know, here are my rates", and they'd come back and say, "Well, that's a little bit more than we want to spend.
• 29:24
  You know, can you do it for X?" And then it would end up kind of fizzling out because it wasn't a good fit for either of us. And so this is a great filtering mechanism.
• 29:31
  Again, I have the privilege of being a more established freelancer. This isn't something that you can do right out of the gate, obviously.
• 29:38
  But it's been a good tool at helping make sure that the projects I say yes to are good fits, and that we're, neither party is wasting a lot of time with kind of the nickel and diming over what it's gonna cost.
• 29:48
  It's, it's if you want this, here's what the rates are, here's my body of work, here's some of the results I've produced. And we do all that over email. The screening- Yeah...
• 29:56
  just kind of happens through the intake form on my website. And by providing that context of here's what it costs, here's what you can expect if you wanna work with me.
• 30:04
  But yeah, it's been helpful at, at just being more efficient because like I said, I was wasting a lot of time on these calls, and things just wouldn't end up working out, and then I'd be frustrated because I'd tied up three hours that I could have spent working on something that made money.
• 30:16
  Yeah, yeah, totally. Is that one of the things that you work with when you have coaching clients? 'Cause I gotta think that that's a huge challenge, especially for folks who are earlier on in their career. Yes.
• 30:25
  A lot of it is process oriented. If you come to the relationship with a process in place and kind of say, "This isn't my first rodeo. Here's how this process is gonna go. Here are my expectations.
• 30:35
  Here's what I need from you", that really sets the tone for the working relationship, and it feels totally different going into a working relationship with somebody who, again, is coming to the table with this established workflow rather than just kind of being led by the hand by the client who can then kinda, that's where you get into scope creep and, and trouble with boundaries and things like that.
• 30:56
  So it's kind of a baller move- Yeah... but it seems to work really, really well. Yeah, yeah. I would encourage es- like, anyone, particularly who's a freelancer listening, like go to Kayla's website.
• 31:04
  You can see it for yourself 'cause I read it and I was like, dang. Okay, this is legit. [laughs] I feel like it also does send a signal too that like-You're gonna get something really good in return. Yes.
• 31:13
  I'm not gonna half-ass this. Like, I'm gonna deliver you great work. Right. If you're paying me this, I'm gonna do a really good job. Yeah. And I think that that's another thing too.
• 31:20
  I always do what I say I'm going to do. I never fall back on that, and I pr- I feel like I over-deliver. So I underpromise, over-deliver every time so that I'm sure everybody is happy with the final product. Yeah.
• 31:33
  If you were starting all over again today, it's like day one, you're a freelancer, is there anything you would do differently? You know, I've thought about that a lot of times, and I, I just don't think so.
• 31:42
  I, I feel like I've learned everything at the right moment. Things have really played out the way they were supposed to. I've pushed myself.
• 31:49
  I've had a lot of good friendships and mentors and people that I've networked with along the way who've given me a nice boost, and I've been able to do that for some fellow freelancers on the back end.
• 31:58
  So I really don't think so.
• 32:00
  I think the only thing is I wish I would've got those processes we just talked about in place a little bit sooner and save some time, um, as far as efficiency goes, but otherwise, I'm pretty good.
• 32:09
  I'm happy with how things have gone. That's awesome. Are there any resources that you've encountered over the years that have been particularly helpful?
• 32:16
  Like, you mentioned The Creative Class, which you then ended up working on or like, I don't know, like mentors, conferences, courses you've taken, people.
• 32:23
  Like, I'm just sort of curious, like have there been kinda like points in your career that you could point to where you're like, "Oh, I really leveled up- Yeah...
• 32:28
  at this point, and I have a certain resource to thank for that"? Yeah, so Creative Class was a big one for me, the course I took with Paul Jarvis probably three years into freelancing full time.
• 32:38
  And again, that was the course that told me, "Get your processes in place. Make sure that you have documentation for everything.
• 32:44
  Have a contract with every client," just these building blocks that really helped me feel more like a professional than just winging it every time I went into a new working relationship. That was a big one.
• 32:54
  And then the other thing, too, is just having a few good fellow freelancers who do similar work with similar types of clients that I could use as a sounding board. So, "What do you charge for this?
• 33:03
  This project is a little bit different than what I'm used to. What do you say? I'm really frustrated today. Can you give me 10 minutes of your time so I can vent about this? What do you think about AI?" Things like that.
• 33:13
  Having a community of people who really get it, that has been really, really critical for me, too. And I'm not a big conference gal, you know?
• 33:20
  I'm not into tools or a lot of, you know, fancy, high-frill-type things like that.
• 33:25
  But having the connection of a good, strong community, so a place like Superpath is perfect for that, like-minded people who really get it, and then just a couple courses that just helped me get my, my shit together, really.
• 33:37
  It was just kind of as basic as that. Yeah. It's like, "Oh, how do I do this better? I know what I'm doing, but like, help me do it better." Right. You know, I read an article, I think it was by a guy named Geoff Goins.
• 33:47
  Yeah. It's like years ago, probably like 2014, 2015, and he had written this article about how to go pro. Mm-hmm.
• 33:52
  And the point of it was basically you don't become a professional when you make a certain amount of money or you sort of reach some status. Like, it's a mindset, and if you- Mm-hmm...
• 34:01
  treat your work like a pro does, you are a pro. Right. And it sounds like that's exactly what you've done.
• 34:06
  Like, you've taken the whole thing very seriously, which I feel like when I see 1,000 freelance applications to a job, I'm like, not to disparage anyone who wants that work, but like I, I wonder, like, "How many of these thousand people are taking this really seriously?"
• 34:18
  Mm-hmm. It's hard to answer.
• 34:19
  I feel like the writing sample's it's the thing I always find myself gravitating to, and you see the good ones or you see the people who present them well, and you're like, "Well, these people are- Mm-hmm... for sure."
• 34:26
  But there's a bunch of other things, like you've just described, the process stuff, kind of the behind-the-scenes business stuff that are part of that, too. Yeah.
• 34:32
  The example that comes top of mind for me is that when I was in college, there was a job that I really, really wanted right out of college.
• 34:39
  I knew that I didn't have the experience or the body of work for it, so I went through their website's About page, and I made my application look just like their About page. So they had all these fun facts.
• 34:49
  They did this very specific type of bio for each person, and I mirrored that back to them, and that's the same thing. That's like copywriting 101, mirror the audience's language back to them.
• 35:00
  But I really put a lot of thought into it, and I got a call right off the bat. They were like, "Oh, that's really different and unique. Like, you really did your homework here." That's awesome. I got an interview.
• 35:09
  I got a job offer. Turns out they don't, didn't really wanna pay me, like, anything to do the job. [laughs] So it wasn't a good fit, but that taught me how, that's how you get the job.
• 35:18
  You've gotta put in a little extra effort and go above and beyond to really stand out of that 1,000 applicant pile of applications. Yeah, totally. Totally.
• 35:27
  You know, one other thing you made me think of is, like in running my own business, I've discovered or kind of had this realization that the network of people that I rely on and who also rely on me are not just business contacts but actual friends.
• 35:41
  Yes. And all the business stuff ends up becoming, like, quite personal. Mm-hmm. The people that I work with I treat more like friends than I do customers or- Sure...
• 35:51
  subscribers or whatever other designation you might give them. I feel like that's actually been important for me because for a very long time I felt the need to keep it all separate. Yes.
• 35:59
  You know, that work was one thing and personal was another thing, and then I'm like, now I feel, I guess it's maturing or whatever. I'm like, it's all the same. Yeah. You know what I mean?
• 36:07
  Like- We're all human beings at the end of the day. Yeah. You know? And that was part of the reason I switched also. That brings up a, a great thing of I used Lumen.
• 36:15
  I used this faceless business entity to market myself the first couple of years of business, and it wasn't really working 'cause people didn't know who that was. There was no face to the brand.
• 36:24
  And so then I was like, "Ah, I'm just gonna use my name and face." And once I started doing that, that flipped a switch of people...
• 36:30
  I started building more authentic, deep connections with people as a human being, you know, instead of this faceless entity. It seemed to really be a game changer.
• 36:39
  So I always encourage freelance writers to take that approach. I get it if they don't want to. A variety of reasons you may not want to, but it's served me very well so far. Yeah. That's great.
• 36:49
  Could you give us an update on the things on your plate today? You have- Yeah... the writing stuff. You have product you sell. You have two podcasts. Yes, so many things. [laughs] There's a lot going on here.
• 36:58
  Could you just give us an overview of it? Yeah, so I have thewritinglab.podia.com. That's where I have all of my coaching offerings, templates, trainings from past recordings of live events.
• 37:09
  I'm also working on a writing course. It's actually finished. We're just getting the videos finished, so that's on the horizon. Haven't talked about that anywhere, but that's exciting.
• 37:16
  We have the Freelance Writing Coach podcast, which is in an off season. We usually do one a quarter, so we'll, we'll be recording another one soon.
• 37:23
  And then Off The Clock is absolutely anything but work talk, so it's really just pop culture, silly stuff with me and two other marketers who do kind of similar work.
• 37:32
  And then I'm working on a fiction novel, so that's what I've been doing- I saw you tweeting about that... with my, yeah, my time off.
• 37:38
  I'm hesitant to talk about it publicly because then people are like, "How's your novel going?" And I'm like, "Ugh." Yeah. [laughs] "It's slow. It's going slow." But it's a work in progress, so that's where I'm at.
• 37:48
  That's cool. Is that, the fiction novel, something you hope to publish?And sell or is... Okay. Yeah, that's the goal. That's the dream. That's the goal. That's the dream.
• 37:57
  You know, I've got the casting in my head for when the movie comes out. Yeah, yeah. [laughs] So just small dreams, you know, keeping it very mellow, not making it a big deal. [laughs] That's really cool.
• 38:07
  When I think of freelancers who have published books, Paul Jarvis- Mm-hmm... comes to mind as someone who did that.
• 38:13
  Paul Jarvis, also, total side note, did, like, one of the most baller things I've ever seen a marketer do, which is just, like, delete his entire online existence. Disappear. It's just gone. Yes.
• 38:21
  [laughs] And it was so good. So much respect. I mean, I was bummed in the sense that- Ugh... he had written so much good stuff. I got his newsletter- Yeah... for years and years, and now it's just, he just decided.
• 38:31
  I know. I mean, sort of going back to some of the things you were talking about earlier, it's like that's what he wanted, and that's what he did. He's my hero. I aspire to that.
• 38:37
  I would love to just disappear off the internet one day and not be so dependent on it, but right now I'm still in the thick of it. I'm still freelancing, so I need that connection. I'm...
• 38:45
  I have not evolved to that tier yet, but that's the goal. Yeah, totally. I often joke that if I one day sell Superpath and never have to work again, I will retire from the internet. You will never see me- Ugh...
• 38:57
  on the internet again. [laughs] That's the dream. We'll see. I feel like I'd be back. There's a lot of good stuff, too. Yeah. [laughs] There is. That's true. That's true. Well, cool. Kaylee, thank you so much.
• 39:05
  It's just so great to, like, have an opportunity to have this conversation and reflect on- Yeah... 10 years of freelancing. There's so much good stuff in here.
• 39:12
  We will obviously link people to your personal site, the Podia site, the podcast. Anything else I'm missing that we should make sure we link to? I don't think we should give any more links. Okay.
• 39:22
  I've already provided so many. Let's keep it simple. [laughs] Okay. I'm gonna keep it to those, but thank you for asking. Cool, and maybe we can have you back someday for a name. I feel like people would love that.
• 39:31
  I'd love that. Okay, cool. I'll follow up with about that sometime. Great. Kaylee, seriously, thank you. We'll talk to you again soon. Yeah, thank you. [outro music]