How To Get Freelancing Jobs- Part 2

In part two of the series, Brad and Daniel dive into the actionable strategies freelance writers can implement to get writing jobs and stand out in their space.

Brad shares the key words and phrases you should look for on job boards that indicate good clients. He also discusses how to leverage writing for free into a profitable endeavor.

Learn dos and don’ts from a seasoned professional in this impactful episode.




Daniel: (00:00)

Well hello, this is Daniel Midson-Short back again, and I’m joined once again by Mr. Brad Smith, founder of Codeless. Hello Brad.

Brad: (00:08)

Hello Daniel. Good to see you again.

Daniel: (00:13)

Last time we talked a little bit about freelance writing and starting a career in freelancing, and particularly some of the mindsets you know that you have to adopt and the upsides and the downsides of being a freelancer. So if you haven’t heard that episode, I recommend checking it out. Brad gave us some great tips. But today we’re getting to the stuff everyone wants to know, which is how to get writing jobs. And then also talking about things like how much should you charge and how do you increase your fees over time? Because that’s, really the nuts and bolts. It’s the pragmatic part people want to know. So let’s get into it. So in terms of your experience, Brad, I know you and hired writers yourself, and so that’s something you do now. But when you began as a freelance writer, what was your tactic to start getting writing jobs? How did you begin?

Brad: (00:59)

Yeah, definitely. So I think one of the kind of like lowest of low hanging fruits that we talked about, a few episodes ago is job boards kind of in the freelancing space. Whether that’s design, development or writing, typically usually the easiest place because you have people ready and willing to hire someone. And that’s from a sales perspective, that’s usually your biggest hurdle is does this person have a budget, does this person have a need? That’s what you’re constantly trying to suss out. So job boards are definitely the easiest. That being said, different job boards are better at different things. And then there are certain things you should be looking for on job boards when you’re doing it to not waste your time. Because otherwise you could waste a lot of time just replying to a bunch of stuff.

Daniel: (01:44)

Okay. So if we just jump into that specifically for a second, anything that you can think of that you should look for or you should look out for? Things not to apply for?

Brad: (01:53)

Yeah, for sure. So, previously we talked a little bit about specialization. That to me is, not only the space you write in, so it will be maybe the topics you write about, but also the style of content that you’re writing on. Ideally, you want to look for a nice cross-section of the postings that someone’s writing about with your cross-section of specialization, whatever that looks like. So an example of that would be, let’s say I’m browsing job boards and somebody says the words experienced, longterm, our website gets 50,000 visitors a month. What you’re doing is you’re looking for clues that say experienced equals they know it’s going to be a little more expensive. They’re not looking for a cheap writer. Longterm meaning this isn’t just like an overnight one test article and then whenever they call you, again type of engagement. The size of the site,

Brad: (02:53)

okay. They’re probably fairly experienced at this and they’re going to be easier to work with. That’s something that people don’t understand is that the more sophisticated the client is about, whatever they’re hiring, the easier they typically are to work with. And that’s counterintuitive because it usually means like bigger budgets and their stuff. Whereas a lot of people think that you just start at the bottom. Some people do need to start at the bottom depending on where they’re starting. But the bottom is usually the worst clients, the worst paying rates, the most tricky or difficult. So an example of that, even like my company now, like if we produce content for a small website with someone on a limited budget, there was old for them would not be that great. But if we did the same exact work on a big website, the results will be huge.

Brad: (03:40)

And so our value, our ROI to that company is worth way more than the other. So when you’re looking at job board ads, you need to constantly filter this through and it usually behooves you to spend more time on a handful of pitches, maybe one to three a day versus like 10 a day. Because what’s going to happen is you’re going to half-ass, frankly all those, and you’re not going to read the directions and you’re not going to provide very specific published samples that exactly line up with what they’re asking for. And those are the kinds of things that get you essentially cut pretty quickly in the process because this person is looking at 300 new entries. If they put a job board ad up, they’re looking at whatever, a couple hundred, a couple dozen submissions and you want to be in the top five. If you can’t be in the top five, then don’t bother replying to it.

Daniel: (04:34)

Mmm. Gotcha. Yeah, that’s a great insight. And I love the idea that there’s kind of almost like code words for how difficult a client’s going to be to work for or when they’ll pay better. You know, things like that that you know. It’s really interesting. So job boards is definitely the way that’s the lowest hanging fruit, as you said. One question I have is, would you recommend writing for free for people in the beginning if you’re just starting out?

Brad: (04:57)

Yes. Not on job boards. So you go to job boards for work to pay the bills in the early days. You don’t go there to like work on a discount and to try and get your name on a big site. I think what I had a better experience with was just going to the biggest sites I could find in my space and trying to write for them for free from the beginning. And then leverage that work, those work samples over for the published stuff for the job boards to justify higher rates and value. Does that make sense?

Daniel: (05:36)

A lot of sense. Yes. Yeah, definitely. Cause I think it can be a bit of a trap as a writer where you do want to show your value and it’s good to have those, you know pieces for your portfolio. But you can then get trapped in doing a lot of work for free for people who are not willing to pay you whatever value.

Brad: (05:52)

Yeah, exactly. And it’s kind of like an MBA. So I have an MBA from a really small school, therefore it doesn’t matter. An MBA is only worth it if it’s like a top 10 school. So there’s probably an ungodly amount of MBAs in the US alone, like I dunno, 100,000, 50,000, 25,000 and it literally doesn’t matter if you have 24,900 of those, it only matters if you’re in the top 10 like as far as employers go and other stuff. And so it’s similar in this case where writing for like the 25th biggest website for free isn’t going to help you in your space. You need to write for the top 5, the top 10. That’s where all the leverage is going to come from. And if you’re doing it for free, that’s the only way it kind of makes sense

Brad: (06:44)

both figuratively and literally. Like that’s the only way the math pencils out is if you’re going to spend all this time doing something, it has to be top five, top 10. And then if you can’t get in, become a better writer until you can get in. So it forces you to become better at your craft, to aim higher and to have a higher expectation and go after that. And then once you do that, it opens up all kinds of doors on the paid side, on the paid writing side.

Daniel: (07:10)

Yeah. So it’s really, it’s again, persistence in a lot of respects and knowing what you’re trying to target when you’re starting out, if you’re writing for free.

Brad: (07:20)

Yup. Yeah, for sure. It is, but it might take you six months to get on a big website, but once you do, you only need one published sample on it. So you don’t need to keep doing it. You don’t need to keep writing for free forever. You just need to do it a little bit at the beginning and you need to do it the right way to leverage your time and everything. And then once you do it a couple times, then you have those samples. Like they’re never going away. And so if you write for the top five websites in your space, that will almost always get you on the shortlist of people looking for work in your space.

Daniel: (07:56)

Yeah, absolutely. Yeah, it makes total sense. Okay. That’s a great insight. So work for free if it makes sense and you’re leveraging the top websites to do it. Yeah, totally makes sense. In terms of some people like to work their way up through working in an agency. That’s something I did in the beginning. I worked as a content writer inside of an agency before I became a freelance writer. Do you recommend doing it that way or maybe even working as a dedicated writer for a company? Is that a good way to get experience too?

Brad: (08:22)

Yeah, I do. I do and I don’t for different reasons. I would say if the ultimate aim is the freelance route, I would say an agency is probably going to be more beneficial to you because it’s going to force you to learn how to juggle multiple clients, multiple client’s expectations. What one client thinks is good writing is going to be different than another one. And maybe they’re both right. I don’t know. I’m not saying they’re wrong, it’s just that you have to learn how to process that. Whereas it’s really easy to write for one client or to make one company happy and make one boss happy. If you think about that, if you’re writing in house at a company, you probably have one direct boss. Like director of marketing usually. Or at a really large company

Brad: (09:06)

it’s a CML. But like you’re not talking to the CMO. The CMO is not talking to the content writer. Like you’re, talking to the director of marketing or marketing manager or whatever. So if you make one person happy one time, that’s easy. It’s really difficult to make a hundred people happy a hundred different times. So agencies force you through the way they’re set up. They move a lot faster which you need to learn as a freelancer. Agencies typically move a lot faster than in house. Depending on where you’re at in the agency, you probably will get to a point where either you need to move up or move out. So you either need to move up into a position where you’re working directly with the clients or uh, attributing to strategy or something like that. Or you need to jump ship and do your own thing.

Brad: (09:59)

I shouldn’t say that for everyone. That’s not a blanket statement. It’s just if your agency doesn’t specialize in that, that’s the other thing. If you’re just one cog in a wheel, so to speak, and like we all need jobs. We all need money. So being a cog in a wheel is okay for a certain amount of time if you have a plan to do something about it. So if your agency does a bunch of different services and you’re just like one team member and the clients you’re working with are good but they’re not amazing and the stuff you’re working on is good, but it’s not amazing. If you’re not going to move into like strategy or something else, then you probably need to think about making the jump out to freelancing. Otherwise, you’re never going to do the personal brand-building stuff you need to do to actually get the clients.

Daniel: (10:46)

Yeah, absolutely. So, so true. And the good thing I think is, you know, you can potentially do freelance work, on weekends or you could cut down a day a week if you’re working a full-time job or something, build up that portfolio. So it’s not like you have to have this huge jump immediately. You can take your time, which is nice. That’s what’s great about writing is you can do it anytime, anywhere, right?

Brad: (11:06)

Yeah, definitely. I would, I would highly recommend that. Like some companies are okay with it, some companies are not okay with it. Try not to let your work slip for your day job, but you should be thinking two, three steps ahead in an ideal world. And if anything, it takes pressure off because you don’t have to necessarily replace your full-time income tomorrow. It gives you time to be a little more selective. And so maybe you take a paying job with a client that’s more notable and it’s going to have a bigger impact, but it’s not going to be able to pay your full salary. It still might be better to work with that one client for a little bit of time to build up that portfolio and those work samples instead of just writing for like Textbroker where you can’t ever get ahead and you can’t ever get enough work with your name on it and you’re just kind of on the hamster wheel. So in that model you’re making the jump so you can pay the bills, but there’s no like end goal. Like you’re just kind of stuck versus, keep your options open I guess.

Daniel: (12:11)

Yeah, that’s a very good point actually, because as I learned that very quickly as a content writer, I would write some great stuff, but it would always be ghostwritten. It was always on the claim of the client. Right. You know, so they look like they’re a great writer and I couldn’t show my clients because it looked like someone else wrote it. You know? I’d have to say, I actually wrote this, but you know, it was written for this client or whatever. So it can be confusing for other businesses looking at your work. So if you can get pieces published under your name, that really helps. And I know just for myself, one thing that really helped too was publishing a lot of my work. If I couldn’t get it published on bigger sites, I was going to places like LinkedIn and medium for myself, just so it has some sort of platform, you know, to show people a sample at least. That was, that was helpful as well in the very, very beginning.

Brad: (12:55)

Yeah, definitely. It’s not like if you try to pitch something to a big site and they reject it, it’s not the end of the world. You could still reuse that stuff and it’s just like a stepping stone. It’s just like, okay, like you have to get comfortable with, being ignored, being ghosted, being rejected to a certain degree. It’s just kind of part of the territory.

Daniel: (13:14)

Yeah, absolutely. And you know, I always say that, you know, it’s very rarely someone, you know, screaming at you saying get outta here, you bum or something. Nobody’s mean like that. It’s literally “ thanks, but no thanks” or “not right now”. And mostly it’s written in polite emails. It’s not like someone, yelling at you and you’re horribly embarrassed. So don’t fear rejections, they’re fine. Really great point to remember. Um, okay. So now another question I have, and we did talk about this in another episode, but the idea of standing out as a writer and you had mentioned specializing. Would you mind just covering that just briefly again? Like the idea of starting to specialize to help you rise above the normal everyday writer.

Brad: (13:53)

Yeah, definitely. So there’s three main ways off top of my head, but I can only think of two right now. So hopefully when I start talking about it, the third one comes to me. But essentially like the topics you’re writing about the space you’re writing in, the style or type of writing you’re doing. And then there’s one more critical one that is escaping me at the moment. So it may not be that critical after all. But that’s kind of the idea is you have these three variables or levers and you need to figure out which ones make the most sense for you, your background, and then which ones make the most sense in the marketplace. And so I get anxious when people start talking about their passions and they want to like write about their passions and like the, I don’t know if the gardening space, and it’s like well what are the budgets in the garden space?

Brad: (14:46)

Because if the market doesn’t exist, then maybe it’s not a good space to specialize in. And so you need to have more than one passion, if that makes sense. You need to have a few different avenues when you’re kind of looking at all that stuff. The style of content too is for me, I started going longer and more in-depth. Part of that was because I enjoyed it. And part of that was because there’s more money in it again. It becomes less of a commodity. Whereas if you’re just writing like 200-word product descriptions for an e-commerce company, that’s the kind of thing that’s very easy, that commoditized writing very easy to farm out to the lowest common denominator. So just broadly what the internet does is the internet drives down the costs for all commodities and it’s destroying all middle markets.

Brad: (15:33)

So think of like real estate agent. You have Zillow, you have Trulia, you have all these. It’s the same thing with flights. You have Google flights, now you have Expedia, you have, so like what’s happening is the internet is ruthless. I mean Netflix and blockbuster, like you can go on and on. The internet is ruthless at driving down the cost of things. And so you need to be cognizant of that when you’re talking about what kind of service you offer because if the market you’re trying to reach sees you as a commodity, you’ll never actually be able to charge or make what you think you should be able to charge or make.

Daniel: (16:09)


Brad: (16:09)

Specialization is just your unique positioning. It’s your unique way of connecting the dots, connecting all these different dots and then a little trial and error. And that usually helps you understand what people are or aren’t willing to pay for and therefore what is a good market or isn’t a good market? What is a good client? What is not a good client? What you should be charging versus what you’re charging now. All that stuff starts to become really obvious once you make that commitment.

Daniel: (16:38)

Yeah, absolutely. That’s a great point too. And to realize that you are in a market that can be commoditized and you have to find ways to specialize and stand out is really key. And the flip side of that, I suppose probably the last question is how do you know when it’s time to start raising your prices? You know, if you’ve been doing it for a while, is there a sort of a certain time limit or when a client is starting to ask for more work or what are the indicators for you where you say, okay, time for a price increase?

Brad: (17:06)

Yeah, that’s a good question. Uh, there’s usually two good signs or three good signs. The first one is, are clients sticking with you for a few months? Is your offering sticky in a sense of like, not just because you force them with a big contract, but do they actually like and see value in what you’re doing? Are you getting referrals from clients? If you’re not getting referrals, then that’s usually a bad sign. If you are getting referrals, unprompted referrals, even, then it’s usually a good sign. And then the third one is if you’re starting to max out, so most people should be able to write a couple thousand words a day, maybe two, maybe that’s two for some people at the beginning, maybe that’s four. Once you start maxing that out, you can’t really go much beyond that.

Brad: (17:59)

Like even the best writers I would imagine probably don’t write more than 5,000 words a day. And so what that means is your capacity’s becoming smaller and smaller and your ability to take on new work is pretty much going away, which isn’t a bad thing. But what it means is now you need to turn around and get more comfortable with quoting higher prices so that some of your current clients will either drop off and new ones will come in to replace it at a higher rate or it’ll help you cut down on the people who could potentially come hire you. And that’s, that’s actually a good thing. That’s not a bad thing. As a freelancer, you make money by writing, by producing. You don’t make money by sitting on the phone or doing like 10 sales phone calls or 10 emails back and forth.

Brad: (18:51)

And so you do need to structure in a way where it’s kind of like, okay, I’m ready, here are my rates, and you have until this day to decide if you’re hiring me or not. Otherwise I’m going to go down to the next person on the list. And so having that setup, having that pipeline, having all those things together usually allows you to do that. And you can charge higher rates and people will say no and it’s okay because you just go on to the next one versus not having that and getting scared because that person might leave or that person might say no, but you actually really need that money still to pay the bills. So again, it’s one of those things where it’s a combination of factors, but usually if you’re busy, if you’re really tapping out at capacity, if you’re getting personal referrals and if clients are sticking with you for longer than three months, then those are all usually pretty good signs that what you’re doing is working. So you should probably think about how to make it better and then how to raise rates.

Daniel: (19:47)

Yeah, great advice. Very practical. I love that. So keep improving and keep looking out for those signs. Okay, great. Well thank you. That gives me some good insights and hopefully people listening of ways to start to actually find jobs and get paid as a freelance writer if that’s the route that you’re taking. Know that it does take a while and it’s a journey that keeps continuing. I love what you said in, I think it was the last episode you said you’ve lived month to month for a decade now. And that’s it’s a great mindset in terms of being a freelancer because that’s kind of what it feels like.

Brad: (20:17)

It is Okay. Yeah. I mean, other people have said this, but even the concept of like staying broke. So it’s like even when you do start making money, the healthy thing is to just like to not be able to look at that money cause it keeps you hungry and it keeps you in this mindset of like, Oh yeah, I just live month to month. Like every single month I need to make as much or more than I did last month. And if you just keep doing that, even if it’s a little bit at a time, that’s where you see huge gains over a short amount of time. It’s just a process. You have to enjoy that, that process of getting better, raising rates, trying to sell more clients, getting better, raising rates, trying to sell more. And it just, it never ends.

Daniel: (21:00)

Yeah. I love it. Very cool. Well. Great. Well, I know that you have an email guide or was it an email newsletter series that you have, which has some tips. Is that right? On Grammar Gang that people can look at?

Brad: (21:13)

Yeah, for sure. That is a free newsletter. You just have to sign in or drop in your email. There are seven parts, one quick daily lesson and there’s nothing for sale afterward. It’s just a simple email newsletter. I hope it’s helpful. It was kind of taken from another thing that I worked on previously and then I realized, Oh, people should probably hear this. I feel like a lot of times, the way writers typically think about this stuff isn’t always good. The noise isn’t always the best way, the optimal way for your time and your life and everything else. And so I wanted to make sure that people understood there’s a different way to do it and that you don’t have to be a broke writer forever. If you just knew how to approach it differently then there is a very clear path to make it work for you.

Daniel: (22:05)

Very cool. Yeah. Well go to Grammar Gang and check that out and you can sign up for free and there’s nothing, no sneaky sales pitch at the end, which we all appreciate because usually, that’s the case.

Brad: (22:14)

Unfortunately. Now I feel like it’s a missed opportunity now I felt like I should have had something there, but yeah, no, it just, after day seven, it just ends. I don’t have any other email set up. I probably should, but I don’t.

Daniel: (22:23)

Thank you, Brad. We appreciate your time as always and if anyone wants to check you out, it’s or Those are your sites. So thank you for being with us today.

Brad: (22:35)

Thanks, Daniel. Appreciate it. 


How to leverage writing samples to become in demand in your space (07:35)

You don’t need to keep writing for free forever. You just need to do it a little bit at the beginning and you need to do it the right way to leverage your time and everything. And then once you do it a couple times, then you have those samples. Like they’re never going away. And so if you write for the top five websites in your space, that will almost always get you on the shortlist of people looking for work in your space. 

Brad points out the reality of commoditization and shares how he avoids being an easily replaceable writer. (15:00)

I started going longer and more in-depth. Part of that was because I enjoyed it. And part of that was because there’s more money in it again. It becomes less of a commodity. Whereas if you’re just writing like 200-word product descriptions for an e-commerce company, that’s the kind of thing that’s very easy, that commoditized writing very easy to farm out to the lowest common denominator.

How do you know when you should start raising your rates? Look out for these signs (19:26) 

It’s one of those things where it’s a combination of factors, but usually, if you’re busy, if you’re really tapping out at capacity, if you’re getting personal referrals and if clients are sticking with you for longer than three months, then those are all usually pretty good signs that what you’re doing is working. So you should probably think about how to make it better and then how to raise rates. 

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