EP. 005

Growth and freelancing: Do you need employees?

In a society that generally associates growth and positivity, freelancers can feel confused about where their future-facing goals need to be focused. Kaleigh and Paul talk about growth, hiring employees, and figuring out what you truly want out of your freelance career.

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Paul: So, Kaleigh, this is a topic near and dear to my heart, but it’s something … This is probably … I’m big on the lead up to something that isn’t even that fantastical, but I think probably the smartest business decision that I had when I started freelancing in the 1990s was that I could start freelancing and just be a freelancer.

I didn’t have to grow into a big company, I didn’t have to grow into an agency, I didn’t have to hire employees or deal with PR, realistically I could hire somebody to deal with PR or all of those things. So I think that, and this is a bit counter as well, I think that what a lot of people start freelancing they’re like “Oh, well in order to really make it, I have to grow into something bigger than a freelancer.” And I don’t necessarily think that that’s the case. How about you? I don’t even know what your answer is for this. So, I’m curious to hear what you have to say about this.

Kaleigh: You know, the older I get and the more I freelance the more I kind of feel the same way. I feel like I’m … I feel like I’m an ambivert, so I’m a little bit introverted, I’m a little bit extroverted, and I want to do things like grow my authority and have people know me for a specific type of work whether it’s freelancing or writing.

But I don’t necessarily feel great about things like public speaking or going up on a stage at a conference and being like, “Growth Marketer™” (this big person who is known for like going out and doing things all the time ’cause I just don’t … It makes me nervous.) I don’t like it a lot. I like to stay at home and I like talking to other freelancers, I like meeting with other people and learning other people’s stories, but I don’t necessarily want to be that person who is a public-facing persona, exactly…

Paul: Yeah.

Kaleigh: … So I’m kind of on the same page.

Paul: Yeah, I totally feel ya on that. What about employees? Could you ever see your freelance business having employees?

Kaleigh: I don’t think so. I think I might hire other freelancers to help with projects if it ever got to a certain point, but I really … Where I’m at right now, I always say this when other people ask me this question, I’m really happy where things are in my freelance business right now. I’m very content and I know that it’s not always a good idea to be content and to get comfortable because then things change, but I’m working towards kind of keeping what I have right now sustainable. And I think that’s different than just getting comfortable and being like, “Meh, it’s going to work forever.”

Paul: Yeah.

Kaleigh: … So yeah, I don’t think I’m ever going to become like an agency or anything like that. That’s just not … Not in the stars for me.

Paul: So-


Paul: … Oh I’m not done with you yet.

Kaleigh: Oh, OK.

Paul: So I have one more question … Then it’s done. So what about things like … What about other areas of growth, I guess? Do you have anything … So if that’s the case, if you don’t want to grow like Kaleigh Moore the … I don’t remember what you called it. The Growth Marketer™ standing on stage in front of hundreds of thousands of people Tony Robbins style jumping up and down. And if you don’t want employees, what do you think then about growing things like revenue?

Kaleigh: I eventually would like to productize some of what I know. I’m not to that point yet, I’ve only been freelancing for four years now. And I think that I … I’d just like to continue what I’m doing. I like to write. I like freelance writing. I like working with the people that I work with right now, but I also don’t know if I’ll be able to write blog posts for clients that I work with forever. It might evolve into something different. It might become a different working relationship. But I want to find a way to keep what I’m doing right now at least in the same vein.  

So I don’t know what the future holds for that but that’s my goal. I think it’s great to have some passive income and that’s something I haven’t figured out for my own business exactly just yet, but I think down the road that’s smart and I think that’s something I’ll be thinking more about as the future passes.  

Paul: Nice. And I think that … Yeah I like that answer a lot because I think the one thing to think about as well is that there is a way to … And I especially notice this about my own freelance career, there’s a way to make more and more money as a freelancer without having employees, without doing crazy speaking tours.  

You can … As you do more work, as you build up a body of work, as you build up great success stories and testimonials and case studies, you can charge more and do the same amount of work but make more money and I definitely see … When I started I think I was probably charging 15, 20 dollars an hour, something like that. And then now I’m obviously charging a lot more than that. And I’m doing different work but the amount of money … And I don’t charge by the hour, but in my head I kinda calculate it out, “OK. If I’m making this much money I’m doing this much work” then internally I know how much I’m making an hour. I don’t quote that to clients because I don’t think I’m charging by the hour makes a whole lot of sense but I think there’s ways to grow a freelance business that don’t involve having lots more employees or getting into work that you may not even like doing.  

Kaleigh: Right, and I think the whole raising your rates as time passes and as you get better at whatever you’re doing, I think that’s important, but it’s really scary for a lot of freelancers who are new or who are kind of new. And so I love that the Creative Class kinda goes into depth on how to go about doing that the right way I guess. Or the smart way, a strategic way.

And I think … I think it’s possible. I’ve done it too. I’ve also raised my rates but it was a really big … It was a point of struggle for me. It felt very intimidating for me to have to go to people I’ve worked with in the past and go, “Hey, I know I’ve been doing this for X amount of dollars for six months, but now I want you to pay me more”. That for me was like oh my gosh no way, I can’t do that. But when I did it and the client said, “Oh, sure no problem” I was like, “Wow.” There’s so much opportunity with freelancing that I didn’t realize it was going to be that simple.  

And it really is, sometimes it’s just a matter of going, “Hey, my rates are going up. Just wanted to let you know.” I mean, there’s a better way to do it than that…

Paul: Yeah.

Kaleigh: … Of course, but that’s the gist of it. And it’s a hard thing to do when you’re new to the whole freelancing world.

Paul: Yeah, and I’m glad you brought up that the client is like, “Yeah, that’s cool”, ’cause I think a lot of times the things we’re scared of or the most nervous about with freelancing are the things we just haven’t done. And once you do it, it’s OK, like it ends up being like, “Oh it’s not even a big deal, I’ll pay you this much more.” And I think a lot of that comes down to getting a client to a place where they’re like, “Yeah OK, that’s fine”, is considering the value your freelancing brings to … And always being aware of the value that your freelancing brings to your client’s business.

So if you know that the work you’re doing … And I mean for some professions it’s easier than others, but for you if you know the conversion writing that you’re doing for a client is 10X-ing their revenue or something like that, asking for more money is a no-brainer because they’ve already made such a great return on investment for hiring you that when you consider the impact the work you have, the work that you do for clients impacts their business and when you can start to see this is kind of doing well for them, then raising rates becomes kind of a no-brainer.

Kaleigh: Yeah, I mean you have to put yourself in their shoes too. They don’t want to lose you. They don’t want to have you not work with them anymore because you’re probably familiar with their brand and the things that they need and you guys have a good workflow set up, they trust you, they have all these important things in place so to say, “Unless you pay me X percent more, we’re not going to be able to work together anymore” usually they’re going to be like, “It’s worth that to not have to go through training another person and getting them up to speed”. We know you’re good, so let’s keep this going.

Paul: Exactly, and when you put yourself into becoming a valuable person to them, then it’s quite a bit easier. So the other thing I want to talk about on this topic is kind of working backwards from what you like to do … And you brought this up and I wanna touch on this and dive into it a little bit more. You said you liked writing. So continuing to write makes a lot of sense for you whereas if you made an agency you’d probably have to spend a lot of time managing writers than you would actually writing.

And I think that that’s a key observation because I don’t think many people … They get kind of enamored with this idea of having a bigger business seems better than having a smaller business but they don’t consider “What does my day look like?” if I’m running a bigger business. And it’s the whole … if you’re at a party and somebody is like, “Oh, what do you do for a living?” And you’re like, “I work for myself” then it can be like, “Oh so you sell stuff on Etsy or something?”

Kaleigh: Yeah, that’s kind of open-ended.

Paul: Yeah. So it might sound better to say, “Oh I run a company of five or 20 employees.” That just might sound better to other people. But if you think about it, I don’t want to manage other people. That, to me, is like the worst case scenario for my life. I feel like I’ve done something wrong in my life if managing others is the bulk of my day. I know for some people that’s not true. Managing others is what they love. And that’s perfect. I’m so glad there’s other people in the world that like that because I do not.

But I think we have to kinda work backwards when we’re freelancing into like, “What do we want our days to look like?” I love being writer and designer because I love writing and designing all day every night. If I just do this all day every day I’m super happy. And I don’t think enough people kinda think about that.

Kaleigh: Right. Is it worth being able to introduce yourself to a party with a different job title to trade spending your days doing HR type work?

Paul: Yeah.

Kaleigh: It’s a much bigger … It’s going to have a lot more ripple effect than just, “Oh, I’m making more money” and there’s a lot more complexity that comes when you grow the business in that way. And like you said there’s nothing wrong with that and I think it’s great that there are people who are good at that because if there wasn’t the world would be a totally different place.

Paul: Yeah.

Kaleigh: But if that’s not your strength, that’s fine. And I think that just having people be aware that that is fine, I think that’s important because a lot of … I don’t hear a lot of people talking about that.

Paul: Yeah, and I mean or just don’t go to parties. That’s my thing. Just don’t go to parties. So I don’t have to answer the question ever.

Kaleigh: Right.

Paul: Even when people … I’m the worst … So when somebody asks you what you do, do you have an answer to that? That’s like succinct?

Kaleigh: I wish-

Paul: You started the answer with a sigh.  

Kaleigh: … I wish I was good at this. I actually wrote a Medium post about it how difficult it is to explain what I do. Even my own Mom can’t explain it very well but I have a short answer. I tell people that I’m a freelance writer and then they just kind of shift their heads to the side and wanna pat me on the head and be like, “Oh, that’s nice.” But I mean, it’s hard. I don’t have a good answer. I’m working on being better at it but again, it’s not worth me changing my business just to get past that moment of being able to explain what I do a little bit more subtly.

Paul: I just say that I … Because I don’t have answer to that either. And I just told my parents, “I just make the Internet.” And if I tell people … but it’s bad … because if I like tell people that I first meet, “Oh I have an Internet business. No, it’s not porn.” It just always have to follow with that ’cause they get shifty looks like “what d-” especially in the beginning. In the ’90s and the early 2000s I had to explain I do not do anything illegal on this new thing called the Internet. I make websites for legitimate businesses that … Yeah.

Kaleigh: Sure you do.

Paul: Yes, exactly. Sure Paul, sure. So what’s your goal as a freelancer or do you have a goal, like an ultimate goal or purpose for freelancing?

Kaleigh: I kinda mentioned this earlier. I’m very happy with what I’m doing right now. I spend a lot of my days writing blog content for the e-commerce and the software-as-a-service industries. It’s fairly technical sometimes but I really love it. I know a lot about it. And so I would love to find a way to continue doing that for as long as I possibly can. I know that the work might not always look the same. I’d like to do more teaching in the future as well. But I don’t know for sure. It’s just kind of a broad goal. Keep doing more of this thing that I like very much.

Paul: … Yeah, so that doesn’t require growth, right?

Kaleigh: Right. I mean, it’s just me.

Paul: Yeah. And I’m kind of the same, I don’t really know the type of work that … Because I’ve shifted from doing mostly web design stuff to mostly writing to mostly products. It just kind of always shifts.

I shifted niches or niches with the people that I’d do web work for (’cause I started out doing websites for pro sports athletes.) Which sounds really cool but I don’t really like sports. So it wasn’t really the best fit. It was really difficult because agents of pro athletes have to be the biggest assholes in the world for their athletes. They just have to get the best deal for their athletes. They have to get the best deal for their athletes, they have to keep their athletes in mind. So if you’re hiring somebody like an agent or even a dispute litigation lawyer, you want the meanest most demanding person ever because they’re going to go to bat for you for that.

Kaleigh: Right.

Paul: But that wasn’t fun for me. So I was like OK, I have to go find a different niche. So I started working with startups, and that wasn’t fun. So I ended up working with women entrepreneurs (mostly authors and online product businesses) and that felt like a great fit … And each time I jumped I was like “OK. What would this jump look like in terms of the daily work that I’m doing?” because I don’t want that to change. And even when I jump from mostly freelancing to products I was like I don’t want … I like my life but I like my day-to-day stuff. I don’t want that to change so I’d rather turn down air quote “opportunities”, because I don’t always think opportunities are actually opportunities, because I don’t want that to negatively impact … And I think that’s why I resist a lot of growth.

And obviously I’m writing an entire book on this so it’s embedded deep in my brain right now. I’m talking about growth and questioning growth. But I always consider the cost of any opportunity whether it’s a new client project or somebody wanting to hire me or building a product, I always consider the cost of the opportunity and if the cost of the opportunity means growth or managing people, I’m kinda like, “All right folks, this isn’t a good fit for me.”  

Kaleigh: Right. I think that’s wise. I think you have to ask yourself what things you like and what do you want to do in the future and how do those align? And I think that’s is as simple as it has to be.

Paul:Y eah. Well, that is as simple as it has to be because I think we’ve probably reached the end of this episode.  

Kaleigh: Well, good for us. It was a good topic.

Paul: So thank you very much everybody for listening to us win at this podcast episode. Hopefully, obviously, you got something out of this as well.

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