When I grow up, I want to be like Kaleigh.

How couldn’t I want to get to a stage where I take on just enough work and have plenty time for walking my (future) dog?


(Just to clarify, this is Kaleigh’s dog but he’s everything a good, good boy can be and more!)

There’s a long list of reasons that make Kaleigh a role model for so many freelancers and communication specialists. Here’s just one example.

Understand how you work so you can improve your flow

Before talking to Kaleigh, I’d already learned a bunch of practical things from her about how to be a better, more professional freelancer. Listening to the Creative Class podcast, which she does with my previous podcast guest, Paul Jarvis, was incredibly helpful in setting appropriate expectations about this new way of working.

And it’s not just the podcast. My friends who took the Creative Class course swear by this experience and highlight how truly helpful it was for levelling up their freelancing game.

That’s because on top of being a highly sought-after writer for SaaS and e-commerce, Kaleigh is also a great teacher. Her deep focus on structure, prioritization, and building self-awareness are the key ingredients that she uses to make her life more rewarding and enjoyable.

We talked in depth about her process and how she developed with intent, fine tuning it over the years. Kaleigh also shared her daily routine, what she does to manager her work effectively and how she made improving it a daily habit.

We discussed how she makes decisions now and how she moved from making impulsive choices to a more analytical and systematic approach (spoiler alert: it doesn’t come naturally). This echoed my own experience from the past years which got me excited to compare experiences and explore similarities and differences.

Kaleigh mentioned how important it is to have people around you who can nudge you to look at the big picture. Being a freelancer can get lonely, so having a few close friends who do the same work plays a huge beneficial role.

The entire conversation is packed with Kaleigh’s wisdom and her practical tips that come from personal experience.

I had a blast interviewing her about how she manages to achieve so much while keeping her business flexible and adapted to her needs. On top of that, the way she helps others shine and build a career and life they love is inspiring!

You can hear it in my voice and I suspect Kaleigh enjoyed doing it too. 🙂


After you listen to the episode, I highly recommend you subscribe to Kaleigh’s newsletter and check out the Domina retreat she’s doing with her good friend, Emma Siemasko.

I hope you’ll enjoy the episode and get a valuable perspective on how you can improve your work and build a more rewarding life no matter if you’re a freelancer or not. Kaleigh’s wisdom and personal examples work for anyone who wants to live more meaningfully.

Resources mentioned in the podcast:

, 2019, 2020

My own article on imposter syndrome.


Alternatively, play the episode in your favorite apps:

Apple Podcasts | Spotify | Overcast | Simplecast | Stitcher | Pocket Casts | Player.fm

Full episode transcript:

Andra Zaharia: Kaleigh Moore never sits still. She’s one of the best freelance writers for software as a service and e-commerce companies out there. She also teaches other freelancers how to build their business in the creative class course, along with my previous guests, Paul Jarvis. What’s more, Kaleigh coaches other freelance writers. She sends out an awesome newsletter and somehow finds the time to walk her wonderful dog, Brooks. I think we had a great conversation because of our shared love for the Gilmore Girls, but that’s just one aspect of it. If you came to understand what decisions go into building a freelance business, you will love this episode and packs in digs down into just that. So, Kaleigh, hi! Welcome to How Do You Know? It’s so good to have you. 

Kaleigh Moore: Thanks for having me. I’m looking forward to chatting with you today. I think we have a lot of interesting things to talk about. 

Andra Zaharia: Oh, I cannot wait to dig deep into your process and ask you like a bunch of questions that are going around my head and to hopefully discover more as, as we go throughout this conversation. You know, I’ve been learning from you and learning from, from Paul Jarvis as well through the creative class podcast and from your work so much, especially in the past month working as I work my way up to becoming a freelancer and then, when the switch actually happened. And I know that people are super curious about how you managed to do so much and be so effective and have these absolutely fantastic results. So, I’m really looking forward to taking that into that, and hopefully everything that’s behind all this great output and all this great work that you’re doing. 

Kaleigh Moore: Yeah. I’m looking forward to chatting about that! I don’t get to talk about the nitty gritty that often. So, it’ll be interesting to, like you said, get into that and talk about the details on the back end of things.

Andra Zaharia: That is so awesome! And you know, your honesty and the authenticity really shine through your work and everything that you do. And that is one more reason why I wanted to get a chance to talk to you about these things. So, getting right into it, I wanted to ask, since you always seem to be picking apart the processes or challenges, and you have this very methodic approach of breaking down complexity into things that are manageable and that feel very approachable, how did you get to this point where it feels very natural to do this? 

Kaleigh Moore: That is a good question. I think it took a lot of years of feeling like there was a lot of chaos around the work that I did and being frustrated about how to sort through, like you said, those complex ideas and sometimes fairly technical subject matter around the things that I was writing for. And so, I really, I tried a lot of different things when it came to the actual execution of the writing that I was doing. And what I eventually found was that having a good strategy and a good plan, and basically, a good outline that serves as a map and that provides some direction for the works that I’m doing. That helps add a lot of clarity. Number one, I think that’s the big thing: it adds a lot of clarity to the whole process and it makes the whole experience of writing and creating something a lot less stressful. So, having just kind of a clear map of “Okay, here are the things that I’m going to talk about. Here are the concepts that I’m going to dive into. Here are some of the natural questions that are prompted around the things that I’m writing about and the questions that were coming up in my mind as I was learning about these things.” And then really just putting that into an outline format and tackling it. Strategically from that and working from a good framework, makes the whole process a lot less daunting because when you don’t have that in place, and you’re just kind of throwing words at a page or endlessly researching and not really ever finding a good structure with things that can make you crazy and it can make your work take so much longer. And for the editor, it makes often times a lot more edits and it makes the editing process take longer. So, the structure is really important for just adding a lot of simplicity and it does take longer. Sometimes it takes a lot more planning. You have to be a lot more mindful of how you want to teach something or, you know, the logical flow of things, but it’s hugely valuable. And it’s really changed my process and made my life a lot easier and a lot simpler. 

Andra Zaharia: You just sound like you’ve been organized all your life. So, I cannot, you know, as someone who obviously proceeds your work and your experience from the outside, you seem like this is very deeply ingrained into your personality. So, I was wondering if you’ve ever been like super organized or if it was a tendency where maybe something that you saw in your family or in your group of friends that became such an important part of you as you move throughout your life and your career. 

Kaleigh Moore: I think that for me, it was kind of a learned behavior. So as a teenager, I was somebody who had two closets in my room and they were always full of a lot of like piled on top of each other junk. Like it was this crazy mess clothes all over the floor. Like very messy. I once left a sandwich in my backpack for like two months and it turned green. I forgot about it. So, I definitely I didn’t always have a personality or habits that were reflective of how I am now. So, I think as I got older and like I said, as I started to get stressed out by those kinds of habits and thinking of approaching things that way, I realized it didn’t have to be like that and adding a little bit more organization. And like I said, mindfulness and structure to things. Yeah, it takes more time, but it makes things simpler and in the long run. So, I think it probably took me a good 10 years to get good at that. And I’m definitely not perfect now. I definitely still have some trouble staying organized, but I mean, I’m not even somebody who makes their bed in the morning every day. I’ll make it at some point during the day, but it’s not something I do first thing in the morning. So, I think that that kind of speaks to that question a little bit. 

Andra Zaharia: Oh, that is a very interesting change in perspective. I think because most people see, you know, discipline, like something that’s very difficult to acquire and then you would need to put in a lot of effort together and everyone says that it’s good for you, but not everyone, you know, can really see what’s at the end of this effort and what comes after it. For those people who struggled with discipline I think you’re, you’re a very good example of understanding how we can simplify our life and it can clear up your thinking because obviously I think of myself as a very organized person, and I love making lists. They kind of organize my entire life around them. But still that big pile of books that I read, like I began reading five or six at a time. And that big pile of books on my desk says that I do not have, well, I have not yet attained that level of organization that I really wanted to. I think it’s very important to understand that this is a process that each can take at their own stride, but engaging in it, I think it cultivates and it spreads throughout your life and helps you cultivate so much more like self-awareness, which is something that you definitely make a lot of use of, you know, both in your career. And I think that it probably happens in your personal life as well, given that one influences another. So, I wanted to ask if you remember a starting point towards building this very intense self-awareness and how it’s helped to you both in your career and maybe in in the important traces in your life as well.

Kaleigh Moore: That’s a good question. You know, I’m pretty fortunate to have a spouse who’s very grounded and is very good at, maybe if I don’t see a point of view or perspective on something, bringing that to the table and asking me to think about it that way. So, I think that has helped me learn a lot about myself. It’s also not always fun to really take a hard look at some of habits or the things that you do on a day-to-day basis. And question them a little bit, it’s hard to change. I mean, like I said, I feel like I was a pretty different person 10 to 15 years ago. And so, it does take an open mind and a willingness to be open to change and to be willing to have that self-awareness and to think about how can I maybe do things better or where are the gaps in what I’m doing now And, basically, it’s like a lot of the people in the world that I work in, which is software, they talk about optimization. And so, in a way it’s kind of self-optimization, how can I juice the most out of this day or this process, or, you know, just get the most out of my work-day, something like that. And so, it’s hard, like I said, it’s not easy. It’s not always fun, but as long as you are willing to think kind of strategically and think open-mindedly about how you could do things differently or maybe where you could have done things differently and try to do better in the future. I think that’s really helpful. And like I said, I’m not perfect. Like there’s still a lot of things that I do wrong. I still have a lot of room for improvement, but I think learning also helps a lot with this too. So, like you, I’m an avid reader. I love to read; I do things like masterclass. I love to watch PBS and BBC documentary. So, I think having a mind that’s programmed to learn and to be open and accepting to new ideas, I think that helps a lot too. And so doing those types of activities where you’re always obtaining new information and I would say like adding to your file folders inside your mind, that’s really helpful too.

Andra Zaharia: Oh, that is definitely one of the biggest things. I think that is going to be like a core skill for the future no matter what the future brings, because our jobs as content marketers didn’t really exist 10 years ago. So, we have no idea how that’ll change in the next 10. And I think that having this growth mindset and having this, the students’ attitude towards life and everything that we’re still discovering about ourselves and about the things around us. Can get you also through maybe the more difficult times, especially I think from, from what I’ve heard and from my very short-lived experience. So far, as a freelancer, I know that you really need these processes and these anchors to hold you through the rough moments when you start doubting yourself and when imposter syndrome pops up all over the place and kind of takes your energy away. So, I think it’s very important that he mentioned this and that you explained some of your source of learning. I’m sure that there’s a lot more we’re going to discover a longer conversation too. And you also mentioned something about a few questions that you use to kind of figure out where you are and what else you’re missing and what you might add to your work or improve. You mentioned a question related to “How do I figure out what the gaps in my knowledge are out there? Any other similar questions that you use regularly, maybe both in your work, that kind of   help you generally with the decisions you make. 

Kaleigh Moore: Yeah, I think just kind of taking a basic journalistic approach to at least to the work that I do. So, asking those really simple questions of like: Who? What? Where? When? How? and then really tackling. If you can tackle those things first and get a good grasp on what it is that you’re trying to do, who you’re trying to talk to, what you’re talking about, those types of things.  That’s usually a good guidebook as far as like getting your footing with a really complex piece of content or connecting the dots between really advanced ideas and concepts. So, if I’m working on a really long form piece and I’m feeling intimidated by the subject matter or the amount of work that I have to do, or the amount of research, just kind of starting with those basic questions and getting answers to those is usually like the very early stages of my outline. And so it’s almost like in a way, it’s the writing brief. It points me in the right direction and helps me figure out what I’m trying to do and who I’m writing for and why. And if I can have that information in place, I can usually get a pretty solid start and just get things moving because oftentimes, like that’s the biggest hurdle ride Is like staring at the blank page and, you know, you have this assignment, you have a deadline, but you have to have a starting point. And so, yeah, just taking a journalist mind to those types of assignments or types of work. That’s a really simple way to get started. And it keeps me from struggling with writer’s block o just feeling like too intimidated to even sit down and write that I feel like is a good starting point.

Andra Zaharia: Oh, I think that those are very useful tools to, you know, mental tool, to kind of break out of the box. Even if maybe some people may be looking for, let’s say recipes or guidelines that are more complex, but I always saw that the simplest questions knows that people haven’t been asking for forever basically have the biggest impact and can reveal kind of the most important… the fundamental details of life and work and whatever dilemmas we’re struggling with at any point in our lives. Speaking about, your freelancing career, you’ve been doing this for almost six years now, if I’m not mistaken. I wanted to ask, I remember making the decision of going from a full-time job to a freelancing job. How you see decision in hindsight? Because it’s been more than half a decade now. 

Kaleigh Moore: Yeah, wow. That’s weird. I don’t even really stop to think about that, but that’s so weird to hear somebody else say. So, looking back, I had a good job. I was working in PR for a nonprofit, but the thing was, as most nonprofits are, they were fairly resource strapped. And so, I had some time during the day, usually throughout the week where I was like “Man, you know, if I were at home and, you know, freelancing, I would have a lot more efficiency built into my day to where I wouldn’t be strapped to this desk, eight hours a day. I could just get done what I needed to get done and then go off and do something else that I wanted to do.” And so, I started doing it on the side and within about six months, I was making almost as much through a couple of retainers that I had in some initial client work that I had gotten almost as much as I was at the full-time job. I was younger at the time. I think I was 24. Yeah, 24. And it was a good time for me. I mean, I was still pretty young and didn’t have kids, still don’t have kids in case you’re wondering. But I was just like, you know, I’m going to give myself 18 months and see if this works. And my husband was on board with it. We were just newly married at the time. And so, I gave it a whirl and, you know, a year in I had made more than I was making at the PR job and was steadily growing. My client roster was steadily getting new referrals for new work. And so that just kind of added the sustainability that I was so concerned about. The big thing for me was like, “Can I make this work long-term?” But those referrals really helped to make that possible for me to where I had this recurring, basically green-lighted customers coming my way, who were from other people, who were happy with the work that I had done for them. So, I think it was a good timing. I think I was really fortunate to kind of just randomly fall into the world of software as a service at the time when… I mean, six years ago, things have changed so much since then and it’s grown so much, so tons of opportunity, great place to be. Same with e-commerce, that’s the other world I work within quite a bit. And so, I was fortunate. That was fairly luck. But yeah, I think again, I think just kind of having an open mind and a dedication to keep learning and getting better has really helped guarantee that I like have recurring work and I’m not just like “I’m good. I don’t think I need to learn anything else. I’m pretty comfortable with how things are going.” There’s a lot of fear I think, to freelancing. And so, having a fear that drives you to keep learning and to keep reaching back out to old customers and asking for testimonials and doing all of those things that make it sustainable, it’s worked out really well. Like I said, I’ve been really, really fortunate. 

Andra Zaharia: Oh, and I think that, good fortune was definitely favored by a lot of work and a lot of commitment to making this work and to putting on your best results. And it’s no wonder that you’re one of the most appreciated and sought for specialists in the business, because it’s obvious, you can tell that your quality of work reflects all that effort. That’s put into it and there’s no match to that in my opinion, because the most successful people I follow and, I say success has many definitions, in my view, but the people who feel balanced and that put out fantastic work that really drives change and helps businesses grow and also empower generations of other specialists in whatever industry they may be all very consistent and very persistent in their work.  And I, to anyone who is listening to the podcast and who’s listened to other episodes as well, I think that this is clear that the path to making better decisions, as well as also through doing the work again and again, until you figure out progressively ways to do it better and better. It’s not really that complicated, but you do have to get shipping and do it over and over again until you kind of get the hang of it. 

Kaleigh Moore: Yeah, so true!

Andra Zaharia: Given that, your work is basically, you’re guiding your readers to decisions, to choosing what they buy, to making choices about their business. Mostly because you’re in B2B software as a service marketing. How does that influence the way you work? Because I think that there’s a level of responsibility that’s involved with content marketing, with content writing just as it is with journalism, for example.

Kaleigh Moore: That’s a good question. I think in the world that I work in, like you said, software as a service, it’s very much education oriented. And so, what I try to do is just put myself in the shoes of the reader and really think about what questions are organically prompted by what I’m writing and how can I answer those and how can I anticipate the things that are going to make somebody sweaty or nervous about, like trying to do whatever it is I’m teaching them to do. And I think that taking that mindset and taking that approach within writing one makes it really personable and conversational because you’re using a lot of rhetorical questions and showing that you’re on the same page with the reader, but you’re also being very explicit in how you teach things and how you show things. And there’s a lot of detail. So, it’s very much a deep dive a lot of the time where I’m not just giving like some fluffy surface level tips. It’s very much like “Here are the steps for how to do this. And here are screenshots that show you exactly what you should be doing at this step in the journey. And, here’s some questions maybe that are popping up in your mind as you think about how you’re going to work through this on your own. And here’s what you need to do when those questions pop up.” And it’s very much a teacher mindset and I think that having that approach to writing, it means that once you spent a lot more time writing because you have a lot more things to answer and a lot more things to address within a piece, but it also produces these really valuable evergreen pieces of writing that. I mean, two and three years down the road, people are still turning to for “How do I do this one thing? Or if I’m trying to do X better, what three steps do I need to follow?” Something like that. And so, I really enjoy writing those. They’re often really challenging, but those are the ones. Those are the pieces that I’m most proud of when they’re finished, because they’re just, so you can tell that it’s something that somebody has sat down and really put a lot of thought into. And it’s something that teaches oftentimes something that’s brand new. So, it connects the dots from, and gets the person from point A to B and helps them do something that’s either really remarkable or that produces really impressive results for the business that they’re working for or solves a major problem that they’ve been struggling with for a while. And so, like I said, taking the teacher mentality and really just trying to write that way, I think has been it’s the biggest thing I had to learn how to do, but it it’s something that comes very naturally now. And I think that it’s something that’s really valuable as far as what I can offer to the client. And then in turn, what they can offer to their readers. 

Andra Zaharia: Oh, wow. That is so, so interesting to get, you know, an insider’s perspective on, because of all that it’s very obvious that you do this very naturally in your work. I think that it’s very important to note that the state teacher’s mentality is something that you also teach other marketers, not just your audience and not just help your customers educate their potential customers. You also do this, you know, your style of coaching because you’re basically teaching people and coaching them towards making better, more informed decisions. You’re helping them become more aware of their context. And I think that that shows that you’re very in touch with the emotional triggers that drive us generally when we make choices. Although, we like to think of ourselves as very rational people, but if you read enough on the topic, you keep bumping into this, the same argument that we’re actually not. I was wondering how given that, you’ve acquired all this knowledge and all these skills and built your intuition along the way? I was wondering how you teach this to the students that you coach, because I know that you have a coaching program and they’re very curious, because these are very kind of abstract things to pass on. So, I was curious how you try to teach them?

Kaleigh: I think it’s twofold. I think the first thing is number one, being really curious and asking a lot of questions. So a big part of the coaching program that I offer, which is just, one-on-one usually it’s a beginner level freelance writer who’s just kind of trying to figure out their footing and figure out their niche and you know, what services they want to offer. A big part of that is doing outreach and talking to other people who could potentially hire them for the work that they want to do or who are already doing the type of work that they want to do. And really just trying to get inside their mind and see, okay, what’s your process around X thing? or what do you look for in a freelance writer? If you’re going to somebody that you want to hire, what are the things that your favorite freelancers do for you that go above and beyond? And like, why do you love working for them? And so really, sometimes it depends on those people being open and willing to share, which is hard sometimes because time is not always of the essence for all those people. They’re busy, they have a lot going on, so they have to be willing to share too. That’s a big part of it but having that curiosity and asking those questions and really just trying to get behind the scenes on well, what’s really going on here? I think that that’s a huge part of one being a good freelancer. And then to also making you a better writer because it learns, it teaches you how to ask the right questions and how to really get to the core of what you’re trying to address either in a post or with your career, whatever it is, it helps you get through the walls of like, you know, there’s a million podcasts, there’s a million books, but what are the true nuts and bolts of how things are working behind the scenes? And what’s getting people hired? Things like that. I think the other side of it is, just having a lot of good processes in place. So, good structure being organized. Like we talked about a little bit ago, and a lot of that is just teaching them. “Okay, here’s how you do an onboarding template” or “here’s how you lay out your process within an initial email, when a client reaches out to you.  “Here’s how you establish contract and things like that.” And so having those process elements in place, one makes you look more professional and two, it helps you save time because when you’re a freelancer, your time is money. So, adding that efficiency in it, it’s really helpful as far as like staying organized and, just coming across to the client as really basically having your shit together. Sorry to swear, but that’s essentially what it is. 

Andra Zaharia: No, please go ahead and swear. I actually, I listened earlier today to your episode with Paul about swearing and I completely agree with it. And I remember that I met up with a client like last week and, like I swear once or twice. And I kept thinking to myself, was it okay? Yeah, absolutely. This is the podcast Mark explicit. Yeah, even though it’s happens much, rarely then the label promises, but yeah, right? You never know how that might change. That is, I think relying on questions is a very important thing to maybe cultivate as you’re reading books in general. This is something that I actually try to jot down each time I I’m reading a good book and, I’ve had to kind of, let’s say a luck and also a curiosity of finding some of the best books in the past years. And they’ve really like changed my perspective. I was super curious if you have any of these books that really, you know, shine a light on you or, just simply brought to your attention or helped you connect the dots in ways that you hadn’t done before.

Kaleigh: That’s a good question. So, for me as a reader, I spend so much time of my day looking at research and news and studies. And so, at the end of the day, when I sit down to read, I don’t often want to pick up a business book. I sometimes just find that really stressful. And so, most of the reading that I do is fiction or historical fiction or biography, autobiography, that type of thing. And so, if a listener right now is like “Yes, I’m going to get some good, like tactical business book recommendations.” That’s not going to happen for me. So, I think, I feel that would fit this category. Paul’s book just came out (Paul Jarvis’s book). It’s called Company of One. It’s actually a lot of the stuff that we talk about on our podcast, the creative class podcast, just about how it’s okay to be small and the benefits of having basically a freelance or, you know, a consultant type operation and I really enjoyed that book. Obviously, I knew a lot of it, a lot of the insights from it already cause he and I teach it and talk about it on the show. But I really enjoyed that one and I would recommend that to anyone who is kind of going, pushing against the mentality of like growth hacking and I have to have this huge business and make a ton of money all the time, I think. Yeah, I think it’s really refreshing and it’s a nice view on like, it doesn’t have to be that way. Another one on my to-rate list is a business book. I haven’t got to it yet, but Jason Fried has one called It Doesn’t Have to Be Crazy at Work. And it’s kind of along the same lines. It’s about like how to go against that mentality of like working a million hours a day and having no work-life balance and things like that. And just really how to find a better balance and a better healthier approach to work. So that’s something I’m very into. And then, one that’s coming to mind right now it’s called How to change your mind by Michael Pollan. It’s not business-related at all. It’s actually about psychedelic mushrooms, but I heard about it on the Tim Ferriss Podcast and I listened to the audio book and I really enjoyed it just from the perspective of how the human brain works and mental models and just kind of questioning the norm around how we think about creativity and just kind of what our minds do in the background. He talks a lot about the default mode network in the brain. I think that’s what it’s called. Please don’t quote me on that, but I really enjoyed that and I thought it was really refreshing, just kind of look at the human mind. And like I said, I spent a lot of time writing about psychology and those types of things. So, it was really relevant to the work that I do. Not necessarily the mushroom side of things, but the science side was super intriguing. So, I liked that a lot. 

Andra Zaharia: That’s I was like, I’m so triggered and I’m so super curious to actually read that as well. Plus, Michael Pollan, he’s fantastic. And his voice is so soothing. I bet that it’s really good to listen to him as well. That I’m definitely going to link to all of those books in the show notes. And I love how you mentioned, you know, Paul Jarvis has Company of One and also the book from kid base camp, It Doesn’t Have to Be Crazy at Work. I love this new, it’s not entirely new, but I think that this stronger and stronger current of doing business in a different way and challenging the status-quo and being very happy with a different definition of enough and success, I think that is very important and guiding, you know, following our values to make these decisions I think it can become really crucial to our health in the long run, whether physical or mental, because so many people burn out from their jobs, from their, I don’t know, general life dynamic, but very few actually stopped to question why this is happening over and over? And I’ve been in the same situation. So, I’m sure that you’ve had like many opportunities to grow into your business, into an agency, or even bigger than that. So, I wanted to ask why you decided to stay in your “company of one”, basically, and to stick to this formula and why it’s working for you and how this has benefited you? Because I think that there’s a rich source of inspiration there. 

Kaleigh Moore: I think, you know, this is something that Paul and I talk about a lot. It’s something my husband and I were just talking about last night. I think that there’s a lot of opportunity as far as like you could scale up an agency and hire a team. And really just there’s so much opportunity right now, especially like I said, within the niches that I work in for growth and there’s so much need for the type of services that I offer and that I know about. But for me, the idea of having a team and like being responsible for salaries and being the point of contact for a lot of different spinning plates at once is very, very stressful. Like I feel like I would be very unhappy if I was in that type of role, where there was so much on my shoulders and so much responsibility that, you know, I had people looking to me as far as sort of livelihood went. I had multiple clients with like big deliverables and big projects. The idea of that to me just makes my armpits sweaty, honestly, right now think about it. And so, I just, I really enjoyed the flexibility that freelancing offers. I liked that I get to sit at home and I don’t have an office to go to, like I I’m in my pajamas right now. I think that that’s great. I love that I can take a walk with my dog in the middle of the day. And I know that it’s a reality that there are business owners and there are agency heads who still have that flexibility. But I just feel like it lends itself very much to a lot of stress, a lot of responsibility, a lot of being strapped to the 09:00 AM to 05:00 PM, within an office setting, because you know, you have people who need to meet with you and you have employees who have questions and they need you to be available.  I just really liked the fluidity that, that working as a team of one offer. And I will say that I do have a small network of other fellow freelance writers that I work with occasionally. If I get too busy, if I have overflow projects or if there’s maybe a project that I’m not a good fit for, I’m happy to hand off referrals to other people who may be specialized in something a little bit different that the client needs. And so, yeah, it took me a long time to figure out that work-life balance was so important to me. But even when I was in the office setting, working in the PR job, doing 9:00 AM to 5:00 PM thing, I just knew that for me, the flexibility was a huge, huge advantage. And I see that more and more people are hopping on board with that now. I mean, even my mom, she works from home now and she’s a remote contractor. She is a CPA. And so just seeing her after having worked in an office setting for so many years, just truly enjoy the flexibility of working from home and having a more flexible schedule shows to me that one, it can be done, no matter how long you’ve been working in an office or what type of experience or background you have. But to that more companies are being open to it for different types of work. It’s not just freelance writers, it’s not just graphic designers or illustrators, it’s accountants, it’s virtual assistants. It’s customer support. There are so many roles that are opening up right now in the remote space or in the contractor space. And I think that that shift is very cool. I’m excited to see more of that. 

Andra Zaharia: Oh, absolutely. And it’s so invigorating and I think it’s so empowering to many people, you know, gaining to take hold of your schedule and getting to have more ownership of your work. And I think that also, maybe for some people, it may build even more responsibility than they would be in an office setting where they have to do reports and sit in meetings and all that, because there are definitely much better ways to work and to do our best work, to enjoy it more and to find this, this natural balance and just basically intertwined kind of our work activities where it’s our personal ones without making it feel forced than without forcing ourselves into the schedule. That is unnatural because the industrial revolution wasn’t exactly, which is the one who established all those words, wasn’t exactly the most natural thing that happened. So, so lots have heard about your mom and I think that it’s so good to see so many examples of people who are taking a chance to experiment life and work in a different way. I hope that, you know, this episode and generally what I try to talk about with the guests on this show also kind of help does the same and helps them ask themselves those exact questions that lead us to kind of better choices for ourselves in the long run. Because you know, when we’re young, many of us tend to overwork ourselves so, so, so much. It’s only when we were now that we realized that something is seriously wrong and flawed but that’s maybe another thread that we can pull out later on. We talked about you coaching your students and you talked about, you know, learning with your husband and from your husband. I was wondering if there are other people who you consult with when you have to make like big choices or when you have run into dilemmas and challenges, are there other freelancers that you talk to or have you ever experimented with coaching yourself? 

Kaleigh Moore: That’s a good question about coaching myself. I have never thought about coaching myself. I think in a way my husband coaches me because he’s very business-minded. He helps me think about the future, where if I was left to my own devices, I would probably just think about like the next week ahead. And so, he’s like, “Hey, let’s, you know, where are you going in the next year?” Like, “what are your goals for the year ahead? asking those types of questions, which is important to think about.    But as far as like, other, you know, a sounding board for things that I’m working through. There is one other freelancer that I always talk to. Her name is MSM ASCO. She was actually one of the first clients that hired me. She worked as the editor at a software company at the time, and she hired me as a freelance writer for that. And she and I have just kept in touch over the past five years and she now freelances on her own too. She and I just, we ended up working with a lot of the same clients. So, she very much gets what I do. She and I are very close in age, so I think that we just kind of demographically make sense for each other. And I think that she has a lot of good insight. She’s very outgoing. She’s kind of the yin to my yang. Like she’s all of the things that I am not. And so it’s good to have somebody who can think about things differently when you’re maybe troubleshooting or working through a question or not sure how to approach something with a client, whatever that might be. And so, even though she’s pretty much my go-to person, there are others, a few other small communities. I use Twitter a lot, not for major decisions, obviously, but for asking questions or for connecting with people. I also have a couple of like Facebook groups and channels that I’m part of. And so those are good for just kind of general question asking what do you guys think about this? those types of things. But I think it’s really important to have at least that one person who is doing similar work or really understands the type of work that you’re doing, maybe from a client perspective or a former client perspective. Because without that, oftentimes, especially if you live in a rural area like I do, you don’t have a lot of opportunities for community and for getting FaceTime with, you know, networking groups or local meetups, things like that, where you could have those more organic one-to-one, face-to-face conversations. And so Emma and I, for example, go and we meet. And work together for a couple of days, usually once a year. And like this year, we’re having a retreat for female freelancers down in Austin, which will be a small group of less than 20 people, which is just kind of like a slightly smaller scale of what she and I have been doing for years. And so I think it’s important to, like I said, have those people that you can turn to, to ask questions who really understand what you do, but it’s also important to have those elements of community too, because otherwise if you’re working alone from home, it can be fairly isolating and it can get really lonely or can. And I mean, social skills are a skill. If you don’t practice them, they get rusty. So, from a lot of different angles, I think that that’s really important. 

Andra Zaharia: Oh, this, I I’m so jealous. I cannot come to that retreat, but I’m sure that it’s going to be wonderful. And I’ve seen what happens when women come together and really support each other generously. And honestly, just, you know, fully embrace these conversations that we’ve probably be longing for so much, for such a long time, but, you know, we never really connected to the right people to have them with. So, I’m really curious what comes out of that. And I’m sure that, you know, that is the starting point of building some very strong relationships, which I think are incredibly valuable, especially in day industry. And one of the best parts I think about working in marketing, generally is that there are tons of generous people who really share a lot of what they do, how they do it, just exactly like you do. And like you’re doing now, and that really helps build other people out and get them to me be more, you know, trust more in themselves and put themselves out there a bit more. So, thanks for doing that. 

Kaleigh Moore: Thank you!

Andra Zaharia: I wanted to talk a bit about how environment kind of  influences our decisions because obviously, just like everywhere else in marketing as well, and in content writing and whatever foreign, mid take, there are all these trends, there are all these things that we’re watching and trying to strike a balance between the things that are, let’s say constant about human nature, such as our triggers are, you know,   default mode that you talked about earlier when we were discussing Michael Pollan’s book. How do you strike a balance between these two and how do you kind of teach yourself to resist making decisions, you know, influenced by these trends? Because obviously some of them really never pan out, as time goes by. 

Kaleigh Moore: That’s a good question. I think it’s hard. I think a lot of times you just, you swing and you miss because a lot of it is trial and error. You can’t predict the future. You don’t know what’s going to come. And so, I think a safe bet, at least from my experience is leaning into what you’re really good at. And for me, that’s been like the writing and the researching and the teaching perspective. I think a lot of it also comes though from, if you find something that’s kind of new or that’s trendy or that you find really interesting, just kind of raising your hand and being like: “Hey, I know a little bit about this and I have something to say and I want to learn more about it.” I think that that’s a good way to kind of dip your toes in the water. So, a good example of this for me is I’ve done a lot of work over the past few years with e-commerce and lately there’s all of these direct-to-consumer brands that are coming out and it’s kind of this whole new sub industry. That’s new. I mean, this is a kind of a new world. And so for me on Twitter, I have been sharing a little bit more about that and subscribing to industry newsletters around that topic and following influencers who are sharing what they know, who are writing about what they know and who I think are just generally smart people and know a lot about the topic and just really being deliberate about like going back and forth with them and asking them what they think about different things. And then also sharing my own 2 cents when I make my own connections or think of something that’s relevant to the industry. And so, I think that that’s a good way to shift your focus a little bit. If that’s something that you’re thinking about doing, or you’re curious about to just kind of see how that goes, I think it’s good for connection building and for networking with people. It’s a good way to learn to, you know, we’ve talked about that already. The importance of learning and staying on top of the news and the trends in the world that you work within. And if you see something that really kind of piques your interest, rather than having a lot of different interests and trying to be learning about all these different things, maybe pick one or two things that you find fascinating and go deep rather than wide. And so, for me like this in particular, the direct-to-consumer brand in the world of like DNVB, which if you are not in that world, that probably means nothing to you, but it’s digitally native vertical brands.   Just finding little areas like that and going deep in them, I think is a good way to, like I said, test the waters, but also maybe find a new place where your knowledge and your expertise makes a lot of sense.

Andra Zaharia: So, I guess achieving focus, that is one of the biggest challenges nowadays, especially in marketing, where you kind of feel that you have to know all these things at the same time, and they’re never not even amount to like 5% of what you should know or what do you expect yourself to know. How do you kind of reinforce, you know, or just help yourself bring yourself to a state of ease that, okay, this is definitely something that I want to focus on and I can, you know, push aside FOMO around the other stuff that you feel kind of the need to let go. So, to keep your mind focused and not be boggled down with unnecessary detail. I guess the question here, because that’s what I was trying to get to, is that, just around building focus and building that power to say “no”, because I bet that you say “no” a lot, to, you know, your customers or I don’t know, project ideas and so on and so forth. 

Kaleigh Moore: Yeah. Saying no, is that hard for me because I feel like I just want to be so nice to, I want to get them what they want, but I have learned to be a lot better at it over the past couple of years, especially. And I think a lot of it is for me, is like just being really clear on the direction of my business and what’s important to me and what my goals are as far as like maintaining that balance of work-life flexibility. Having like, okay, I know I need to make X amount of money, but beyond that, it’s really just kind of up in the air, take it or leave it,   and being okay with that. That’s a huge, huge thing because there’s so much opportunity to compete with yourself and there’s so much opportunity to earn. It can be so tempting to just say yes and to like keep earning money and keep making connections and getting your name on different by-lines. So, I think that’s a huge obstacle to overcome. That’s not just something you can simply be like, “okay, well I’m over it now” and the other thing for me is like, this is really silly, but just like being good at priority prioritization. So, I use a whiteboard and I have lists of all the things I need to get done that day. I have a list of things that I need to get done that month or things that I’m working on. I have like a daily paper list that I work on. So, it’s a lot of list-making I feel like when you can see the things that you need to do in front of you, and they’re kind of top of mind. It adds a lot of clarity around your mental bandwidth, your workload bandwidth, Same, like with a paper calendar too. Like if you see that you have travel coming up, like don’t over-schedule yourself, or if you know that you want to enjoy the summertime, like schedule your Fridays to be blocked off.   I think a lot of it is just like building structure and building boundaries into your business and into your life so that you don’t wind up with over commitment. And then resentment also from saying yes to too many things. 

Andra Zaharia: Oh, that is such, such a good tip. But I think that it’s so important to really follow this because obviously you’re, you’re, you know, planning ahead and kind of think you’re figuring out how long your work actually takes. I think that that is one of the biggest things,   that we struggle with in general, no matter if we’re freelancing, we’re having a nine to five job or whatever it is that we’re doing. I think that that is one of the biggest things and learning to kind of calibrate our efforts, according to the challenge and not overdo it,   as, as sometimes I have tended to do in the past.   I think that is, is definitely one of the big ones. And given you’re such a good planner, I wanted to ask how you, you know, how do you make time for reflection and for kind of evaluating how things went and, you know, just looking back and obviously taking time to, to enjoy your many achievements too.

Kaleigh Moore: I think one is the process thing. So having an exit process where it’s literally part of the steps that I have to complete with every client. So, asking questions, like how did this go? and what could I do better? And would you be willing to offer a testimonial and do you know anybody, maybe you could refer me to for, you know, who needs similar work? So just having a process and basically a template, an email that does all of those things that I can just quickly tweak and send out to a customer when a project is done. That process helps with that a lot. I think the other part is like mentally unwinding and again, scheduling it, really building it into the schedule. I did a little bit with the Headspace app and tried meditation. I’m still pretty fidgety, so I’m still working on that. But I also do yoga and so there’s meditation and relaxation built into that a little bit. And that’s part of my every week schedule once or twice a week. And then, like I said, I’m really fortunate to have a partner who like check-in on those things and asks me those questions and says like how are you doing? And like do have too much on your plate right now. And it’s good to have a person in your life who can do that for you, because sometimes you need that external perspective because when you’re wrapped up in the details and the day-to-day of stuff, it’s so easy to just push off, you know, the meditation, the 10 minutes of meditation and, and keep working instead, or to watch Netflix instead, or like do all these things that aren’t nearly as beneficial as taking some time to just be quiet and think back on what you’ve accomplished or what you’ve done throughout the day. And just let your mind be also quiet for a little bit. That’s something I super struggled with. So structure’s a big part of that. And so is processed too, which is also kind of a form of structure. 

Andra Zaharia: Oh, very good tips all of them. And I think that’s it. You’re making a very good point about being able to have these conversations within a couple. I think that is very important. Part of our allies and that many people could, you know, benefit from learning to ask those questions, even if they don’t come naturally first. And it feels like kind of an awkward conversation to have, maybe because it’s not the same for not all. People are oriented like this, you know, not many people have, maybe have access to these types of mental models and people just pick up life skills as they go. And I think that, you know, challenging, one another in a couple and doing it from a place that, you know, a place of curiosity of non-judgment and freely trying to help one another, because it comes from love and from mutual support. I think that’s where it makes a difference. And does it feel like someone’s evaluating you, like obviously these questions feel at work or even in a business relationship? So maybe I think we could take these lessons that we learn, you know, as professionals and try to use them in our lives as well, obviously changing the context and the setting for it. But I think they do make a very, very big difference and having friends or a spouse that does this and that plays this role in your life that can be absolutely illuminating and can really help you level up and enjoy your life more in general.

Kaleigh Moore: So true. I agree so much. And like you said, it’s hard to find that person sometimes, but if you look around and you kind of test the waters with a few different people, whether it’s a friend or a sibling or a family member or a partner, you can find that person. And if they’re willing to learn how to do those things for you, that makes all the difference.

Andra Zaharia: Definitely I’ve actually had like one of these experiences quite, let’s say relatively recently, about a month ago, I talked to, Mariana Kay, which I know that, from Twitter, she’s for those who are listening. She’s this amazing content writer herself. And she put together a small group of women, which is her, myself, and two other people who are in the same workspace, not physical, obviously in the same industry. And we kind of changed the same, shared the same values. And we just got talking about various aspects of our lives, of our work. And it’s made such a big difference to be able to talk to someone like you mentioned earlier, who understands you, who might be going through similar struggles or who’s even a bit ahead of you and can actually, you know, give you some hard-earned wisdom right when you need it. So, I think that seek out those people and cultivate those relationships, that is one of the biggest types of leverage you can build for yourself in life to help you move forward.  I wanted to ask, before we kind of relatively wrap up, I wanted to ask, you know, around your big life decisions, have you seen, let’s say a similar kind of a pattern that you take, that really helps you? Do you take time to think about a decision more, do you isolate yourself? Do you like to lay out the process, break it down into smaller pieces? How do you have any, let’s say ritual of preparing yourself mentally for these big choices in your life. 

Kaleigh Moore: I feel like instinctively I’m a little bit impulsive. And so I’ve had to really teach myself to pump the brakes a little bit and to slow down before making a knee-jerk decision about something. Usually I will… before giving an answer, I’ll talk about it with my husband. I’ll talk about it with Emma. I might go to a group of fellow freelancers and ask them for their feedback on it. And so, for me, it’s in breaking the pattern of “yes” or “no” right off the bat. And I think in the past, I just always thought every decision was super simple. And as I’ve gotten older and as I’ve witnessed firsthand, there are a lot of ripple effects from the choices that you make that you don’t think about when you act impulsively. And so, teaching myself to slow down and to think about the different factors. And like I said, the ripple effects, that’s been really helpful and I’m still not always perfect at it.

I think I still have a little bit of a tendency to just go and to just act. But I have learned to well, despite still moving pretty quickly on things, at least get some alternative perspectives before giving a final answer. And so, it’s been challenging and like I said, I still fight it all the time, but it’s been really helpful and it’s made me be a lot more mindful and careful about the choices I make.

Andra Zaharia: Well, that something very interesting and very, very useful to keep in mind. I think this example of yours, especially when we’re prompted, we live in this culture where you’re very focused. You have all these people doing so many things at once around you and you obviously want to feel like you’re keeping up and you’re not missing any opportunities, but giving yourself time to think and really reflect on what it takes, where it might take you. And if that aligns with what you want to do, those are absolutely essential. And that is as skill cultivating and worth putting time and effort into it, because it’s difficult to go against your reflexes and that really takes some willpower. So, thank you for sharing that.  Do you have any last thoughts that you’d like to add on top of everything that we talked about before we wrap up and, you know, leave everyone to take all this in?

Kaleigh Moore: I think I would say my only final thought is that the thing that I tell to college students and the high school students, when I go and talk to their classes it’s that, it goes back to the idea of like keeping yourself a student and always being open to learning. And so, if you have a spare 15 minutes every day, and you can devote that to like reading an article. From the news or watching a video on YouTube, that’s something beyond like an entertaining blog or something like that. If you can learn a little bit of something every single day, I think you’re going to be so far ahead of everyone else. You have such a competitive advantage, that helps you with your career, that helps you with your relationships, that helps you with your interpersonal communications. As you have like interesting things to talk about and you understand more contextual references and pop culture references, things like that. If you can devote 15 minutes every single day, which, you know, you have 15 minutes to learning something new, it’s a huge, huge advantage. And so, if there’s somebody out there who’s like, okay, this podcast was cool. I liked the stuff they talked about. Well, what am I actually supposed to do? Start with 15 minutes. And like, spend the time reading a book or pick one article or find something that you can learn where you walk away with something you didn’t have before and make that part of your everyday living experience. I think that’s huge. And for me, it’s made a major, major difference.  Thank you for teaching me so much in the past hour as well, Kaleigh! I felt that if you ever want to make a change, of course, which would not be entirely too far off from what you’re doing now, you could completely be a wonderful teacher in which I’m sure you are already in your coaching sessions.

Kaleigh Moore: Oh, thank you! 

Andra Zaharia: Thanks for sharing all of that and for giving me and everyone who’s going to listen to this episode so much to think about and so much to act on, because I think that that’s where the biggest value is. I feel really fortunate for having been able to talk to you and to get to know you better. And I’m really looking forward to everything that you’re going to do next. I really hope, you know, people seek out not only what you do, but how you do it and use it as an example to kind of their own processes. So, thank you!

Kaleigh Moore: Yeah. Thank you! These are great questions, by the way. This is like one of the better interviews that I’ve ever done. So, thank you for all the interesting questions!