How To Get Freelancing Jobs – Part 1

How To Get Freelancing Jobs – Part 1

With years of experience as a paid freelance writer under his belt, Brad Smith has worked the freelance writing career path down to a science.

In this brief yet information-packed episode, Brad reveals what it takes to be a freelance writer including the mindset you must adopt to succeed and his own path to success in the field.

As founder and CEO of Codeless, Brad holds unique insights into what clients look for when hiring writers. He shares this and more in part 1 of  How To Get Freelancing Jobs.

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Daniel : (00:00)

Well. Hello everyone. Welcome back to the podcast. My name is Daniel and I am joined once again by the esteemed writer and founder of Codeless, Brad Smith. So welcome back Brad.

Brad: (00:12)

Thank you, Daniel. How’s your day going?

Daniel : (00:14)

Going pretty well, sir. Yeah, rolling along.

Daniel : (00:16)

Been doing a little bit of writing this morning and I’m excited to talk to you about this topic, which I know is very dear to both our hearts and we both lived it. And so our topic today is how to get freelance writing jobs. And this is going to be part one. So we’re going to talk about some of the basics of freelance writing. You know, what are these, the mindsets that are part of being a freelance writer, some of the actions that you have to take. And then also get into some of the pros and cons throughout, that you’ve experienced. So I’d love to start for those of you who haven’t heard you on the interview before, I know we did talk in a previous episode, but I’d love to get a little bit of your story if you don’t mind particularly around how you became a freelance writer and then you know, maybe your first big breakthrough, what you experienced and going into your current career.

Brad: (01:02)

For sure. Yeah, I’ll cover, I’ll try and give you the quick synopsis, the cliff notes. So I had been doing marketing services consulting on my own for a little while. Started an agency, a company with my buddy. I was always trying to write for free for big sites anyway to try and attract attention to myself and my company and our services that we were trying to sell, like website redesigns and all that kind of stuff. At some point, I started realizing obviously it takes a lot of time and so it’s a heavy investment when you think of all the things you could be doing to sell services. It’s a long, slow road to start creating content for a bunch of sites for free. And it’s super time-consuming. But what I found at a certain point is a lot of the bigger sites that I was trying to write on anyway, were starting to pay writers and look for paid writers.

Brad: (01:51)

And that was kind of a light bulb moment for me cause I was like, Oh, I can make a little extra money like a little side gig. Plus hopefully, get some clients out of it. It’s kind of like free marketing or free brand building. And so in my mind, it was like, okay, that kind of makes sense. I should probably, you know, do that. And then the first breakthrough was probably one of the bigger sites that was willing to pay more than the average market rate I was looking at it was called ad espresso and we actually still work with them to this day. So maybe like four years now, four or five years. I talked to the founder and it was a really good fit for my background and my style and what they were looking for and wanted. And as I’ve mentioned, their budgets and stuff they were talking about, were a lot more than what I had initially thought, just based on kind of looking around at what other people were charging and paying. And so that was, again, one of those moments that ended up snowballing into other things that made me think, okay, you can, if you know what you’re doing, which I didn’t at that point, but if you know what you’re doing, you could really make a go of this.

Daniel : (02:51)

Yeah, and I think a lot of people fall into the, the world of freelance writing that way too, right? You, maybe you are a half-decent writer in your current job or maybe you’ve always had a passion for it, or there’s some reason that you want to write and then you think, maybe someone will actually pay me for this. So it sounds like that’s kind of the way it starts for a lot of people. But particularly on the idea of being a freelance, one of the things I was interested to ask you about is I guess the mindsets, you know, that are different let’s say from, you know, a normal career, right? You know, if you’re working a job, if you’re in house as some sort of, whether it’s a journalist or a content writer or whatever, you have kind of like a hierarchy. But as a freelancer, you know, it’s kind of open slate. You can do whatever you want, work whenever you want as little or as much and there must be certain different ways of working, different mindsets that you have to have as a freelancer. Did you experience that when you moved over into that world?

Brad: (03:45)

Yes, completely. I always enjoyed working on stuff. Even today, our company is doing well and we have a lot of people and even to this day, I don’t like managing people or coordinating people. I have other people to help with that because I get more enjoyment out of doing stuff and making stuff and creating stuff. And so that was one of the things that I really enjoyed about the freelancing aspect of it was I could also learn like on the job, so I could take a topic that I’m not super comfortable with or super familiar with. Go do a bunch of research, learn something, and then try to explain it in a clever way or interesting way and create something and then that thing would go live and be published and be promoted and people would hopefully like it and share it.

Brad: (04:27)

And so that, that whole little like dopamine hit would also help. I really enjoyed all that, those aspects of it. I also liked, as you mentioned, I’ve always enjoyed doing my own thing, working my own hours, having control over kind of when and where and what I do. That lines up well for the freelancing world. Uh, but the bad news is also the same thing – there’s no structure. And so it’s very easy to be disorganized or lazy. Not lazy in a sense of lazy, like neglecting the part you enjoy. It’s neglecting the stuff you don’t enjoy. And that’s a key thing for freelancers is it’s very easy because you have no one telling you what to do. And there’s very little accountability in most cases. It’s very easy for you to just focus on the thing you like doing, like the writing maybe and not focus on the stuff you don’t like doing, like collecting money or going and finding new clients. So it’s for sure good and bad aspects. It just depends on maybe like your own personality, and then being aware of the risks or being aware of the negative so you can do something about it.

Daniel : (05:36)

Yeah, that’s a great point. I guess, you know, there is a risk element to working for yourself that isn’t present if you’ve always worked in a career, you know where someone’s giving you a paycheck. The reality is that you can lose a client and you don’t have another one and you’ve got to go and find one, you know? And that’s scary for a lot of people, especially if you’ve never done it. So did that change for you overtime where your, your mindset, you know, you’ve got more comfortable with that part of it thinking, okay, well I guess I’ll find some new clients or this one’s finishing up, I need to look for new business. Did that become more normal as a writer over time?

Brad: (06:07)

Yes, for sure. I had been self-employed for a little while before too, so I was already semi-comfortable with it. I think part of it is defining risks. People at big companies would define risk a lot differently than I would. But to me, it seems risky to have one person paying your income- like a job. That seems really risky to me. Because like, in theory, they could fire you whenever they want for any reason, at least in certain parts of the world and certain states. But, it’s also really risky to me to put my money that I’m working hard for into some money markets, some mutual funds, some 401K and not having any say or control over what actually happens to it. That to me is risky and then hoping, praying that it’s there 30 years from now. Uh, so part of it is that defining the risk aspect of it and then definitely part of it is becoming more comfortable with your own skillset. And part of it might be confidence in that at this point, I’ve been doing client services for almost 10 years and I could get fired by any client any at any moment. But instead of, instead of like scaring you, you use it for motivation and you have a healthy understanding of even if money did go away, the client did go away, I could just get another one tomorrow because I’ve done it long enough now that I have the skillsets in certain areas that I’m not too concerned, I guess.

Daniel : (07:35)

Yeah, that makes sense. And I guess that comes with time, especially if you’re considering becoming a freelancer and you’re listening to this, that might not be the case. You know, you might think, especially if you lose a client, you know, for a couple of months or something, it may not even have anything to do with you. Maybe the budget gets cut, they want to move in a different direction, but you can easily say oh no my writing was bad, I’m not cut out for this, you know, I’ve got to go back to my normal day job or whatever. So yeah,

Brad: (07:58)

There are a lot of times it has nothing to do with you and that’s pretty common and you have to make peace with that. You have to have some acceptance over understanding what you did and your own level of quality or whatever and, and take comfort in that as opposed to seeking external validation always from clients. Because you’ll also work a lot of clients who don’t like what you do or may not express it. And it’s not always an indication of whether they like it or don’t like it. And then the other thing too is like part of that process as well, is forced upon you. So I was never that comfortable with a lot of these things before. Like I was never that comfortable with sales. I was never that comfortable, but I was put in a position where I didn’t have the option to fail.

Brad: (08:44)

I had to make money and I had to pay for things. And so it’s like the fear that drives you to embrace it and to embrace that uncomfortableness and get better it because you literally don’t have any other options. And so, it’s not, I think sometimes it comes across when people talk about this kind of stuff, it comes across as like bravery or confidence or arrogance and it is and it isn’t. Like it is that only because of the other aspect of that, which is like at one point you were scared to death and you just had to make it work. Otherwise like your whole life is going to come crashing down around you.

Daniel : (09:18)

Yeah, absolutely. I liken when you start your own business, it’s very similar to when you travel in a foreign country by yourself. If you’ve ever done that, I don’t know where. You don’t speak the language and maybe you have a map or you know, you have something on your phone to get you around, but you’re really on your own and you think, um, I’ve gotta figure this out. And you do. You know, you ask people, you kind of, you look for landmarks, whatever, and you figure stuff out and you get to where you need to go. It’s very similar in business where it’s kind of terrifying, but it’s also exhilarating at the same time.

Brad: (09:52)

Yeah, definitely. My metaphor for it is having kids. I have three young kids and most of the time you’re tired and exhausted and scared and anxious and stressed, but then there’s like 10% of the time when something happens you’re like, Oh, this is totally worth it. This high is so much better than the alternative.

Daniel : (10:12)

Exactly. I’ve avoided having kids for 40 years of my life so I’ll take your word for that,.

Brad: (10:18)

Take your time. Take your time.

Daniel : (10:21)

So yeah, but you’re exactly right. There’s that terror, that frustration and the worry that always, always sort of, ever-present. But at the same time, the high is very high. And that leads me, I guess to the next question is, and you did touch on a little bit, but what do you think are the main, the biggest benefits of being a freelancer versus working for someone else?

Brad: (10:40)

Yeah, for me it’s control. Control over my time is the biggest thing, which sounds odd because as a freelancer you tend to, at least I did, I’m not great with boundaries. So I worked as a freelancer. I’ve worked more hours than I would have if I worked in a job somewhere and I was often more stressed. But the flip side of that is I also was able to make more money and I was also able to have a lot more control due to that money, but also due to other factors, have more control over my life to a degree. So I could move cities. I could go on vacation. I would still maybe work on vacation, but that’s not always a bad thing. I like doing certain things. I can control who I work with and who I don’t work with.

Brad: (11:27)

I could control the style of work. I don’t like working in an office personally. So my company is remote for that one reason I just don’t like working in an office. And it’s not that I don’t like other people, it’s just that I don’t, my work style. I have ADD. I don’t work well with other people around me. I need to focus. And so I’m able to make those decisions because I control all of it which sounds really selfish and it kind of is, but it isn’t. Because I get to spend more time with my family and travel more and do all that other kind of stuff that most people don’t get to because they have to constantly be told what they can and can’t do basically.

Daniel : (12:06)

Yeah, absolutely. I think what you call control I call freedom. Yeah, 100% but you know, it comes with responsibility too. Right. That’s the other side of it too. You’re exactly right. And that kind of leads me to the other side of the coin I guess is what would you say the biggest downsides, if someone’s considering being a freelance writer, what are the biggest downsides?

Brad: (12:24)

For sure you’re trading money for time is a big one. So you’re still not out of the woods just yet. You’re like one step removed from an office gig, but still the same dynamics at play. So you usually will be able to make more money if you’re really good at what you do, but you’re still trading time for money. You could go on vacation. But like I caveated, there’s so many times where we went on vacation or we did a road trip. I’d wake up at like 3:00 AM 4:00 AM in a random hotel lobby, get up, drink like a ton of coffee and write for like three or four hours first thing in the morning, that way I could try and take the rest of the day off. So you still have to make those little sacrifices and you have to be willing to do it.

Brad: (13:06)

It’s not always fun when you’re out the night before and having a good time and maybe drinking a little too much and then you’ve got to get up the next morning at 3:00 AM cause you’re like, Oh I have a due date. Like I need to hit this due date. That’s one part of it. I think before you’re comfortable with this, I think the scarcity mindset is a big problem because you are scared. You have three clients and you’re scared to death of losing one of those because it’s gonna throw everything off. But you also, at that point, depending on where you’re at in your freelancing journey, you’re probably not making enough money where you can reinvest heavily. You can offload it, get some contractors you have, don’t have as much freedom to be flexible. And so you’re just like, I just got to keep my head down and keep these three clients happy. So I think there are a lot of personal risks and things that happen as a result. And I think that would maybe be like the biggest drawback in my mind.

Daniel : (14:09)

Yeah, definitely. And it sounds like it’s just something that you get used to overtime. You just kind of adapt to it. Like anything, right? You ever find one side, your life becomes much easier. I always think about, you know, driving a car. The first time you learn to drive, it’s terrifying. I just cannot do this. And then, you know, two years later you’re cruising down the freeway, not even thinking about it, you know, it’s, it’s totally easy.

Brad: (14:32)

Yeah, like you said earlier, too your analogy with going to a foreign country. It’s really scary. Like the first couple times you do it, but then you get comfortable with it and you embrace it. And so at this point, on paper, I’ve lived month to month, you know, in air quotes for like a decade. At first, it’s really scary to do that. And now it’s like, Oh, whatever. Like that’s just second hand, you know, it’s second nature. But it forces you to grow as a person. It forces you to become more, I dunno, just aware and dynamic and hopefully confident. Otherwise, it will break you. So it’s one of those things where it’s like, what’s the old stupid analogy where granite is hardened over time or something, whatever. But it kind of forces you to like grow as a person and evolve as a person. And until you do that, you’re not going to be at peace or comfortable with freelancing or whatever else that you are doing.

Daniel : (15:27)

Yeah, absolutely. And it sounds like too, the more, you know, not that you necessarily need a ton of clients, you might choose to work with just a couple, but the more options you have, the less one clients, you know, choice to work with you can affect you. You know, if they leave you go, okay, I understand, but you’ve still got seven others or something or 10 others or whatever. It’s much easier to let that person go than if you’ve got two or one.

Brad: (15:51)

Yeah, yeah, completely. I mean that’s, that’s those little tricks you start learning over time is what helps you become more comfortable with it. So it’s not that you become this like this crazy confident super brash person all of a sudden and you’re blind to reality. It’s that you, you have a longer pipeline, you have more leads in the pipeline, you have all these other things kind of figured out. So it’s like you’re hedging your risks and you’re hedging the downside as much as you can. And that’s what gives you confidence. Because it’s like, I would hate for this one client to leave, but if it did leave, I still have this waiting list over here of clients that want to work with me and they’re all going to pay me 30% more than this client is currently. So even if I got rid of them, it would probably be better at the end of the day cause they’re going to pay me more money. So it’s just like doing all those little tricks, helps you understand how and when to be confident if that makes sense.

Daniel : (16:42)

Absolutely. Yeah. And I’m trying, and this is kind of like a leading to part two, which we’ll get to in our next episode, but you have a unique position too because you actually employ writers and you work with companies who, you know, look for like essentially long-term contracts. So I think you have a perspective on terms of when a business is looking to hire a freelance writer, what are they looking for most of all? What are those qualifications? Is the experience? Is it consistency? You know, what are they looking for when they want to hire a freelance writer?

Brad: (17:13)

Yeah, that’s a good question. Typically, well there is like the surface level answer and then there’s like the real answer. Yeah. The surface-level answer is they want someone with subject matter expertise. So that’s like one of the first things is if someone’s talking about gardening, they want to know that the writer they’re hiring understands gardening and understands the gardening space and why they would choose, uh, hoe over an ax. I don’t know. I don’t know what any of these words are, as you can tell, so that’s like on the surface. And can they write pretty well? So that’s the other funny thing is if you’re a better subject matter expert and you can write okay or well not amazing, you’d probably have a better shot at getting that gig with that company than if you’re an amazing creative writer, but you have zero experience, zero examples in that space.

Brad: (18:07)

So that’s kind of like the surface level typically of what most small-ish companies are looking for. Then why do they stick with you? Responsiveness, attitude. Can you hit deadlines? Can you follow directions? Stuff that has nothing to do really with writing. But then the other answer is the service you’re providing isn’t just the service. So you’re, if you’re dealing with a business owner, you’re helping them buy back a full extra day each month to go spend with their kids or take the weekend off. If it’s a local brokerage company, your job is to help deliver five extra leads every single month so that they get one or two more sales, which helps pay for your costs. So I think that’s where freelance writers need to think a little more about why someone’s actually hiring them, not what they’re hiring. Because at the end of the day, there usually is some end results that people want when they hire you. And again, it has nothing to do with semi-colons or paragraph styles or anything like that.

Daniel : (19:19)

Yeah, definitely. It’s very easy to get caught up in that stuff when you’re, especially when you’re a new writer. You’re obsessed about your style and becoming the greatest writer in the history of the world. But it’s, yeah, it’s true. Very true. Well, that’s great. Well, thank you. Those are some really good insights and I think for anyone considering becoming a freelancer, that’s a really honest take on, the upsides and downsides and the mindsets that it really takes and especially how they evolve over time. So thank you for explaining all that. It’s really valuable.

Brad: (19:48)

Yeah, of course. Happy to help. I can’t wait to get into, I think, more tactics in the next episode, right?

Daniel : (19:53)

Yeah, absolutely. So, yeah, so there you go. A preview of coming attractions. In the next episode, we will be talking more about how to find writing jobs and also what to charge and things like that. Brad has a lot of expertise in that, so thank you, Brad. I will say farewell for now and we’ll be back very soon.

Brad: (20:11)

Of course. Sounds good.

Highlights 

What Brad sacrifices as a freelancer and the reward that makes it worth it. (10:53) 

So as a freelancer I’ve worked more hours than I would have if I worked in a job somewhere and I was often more stressed. But the flip side of that is I also was able to make more money and I was also able to have a lot more control due to that money, but also due to other factors, have more control over my life to a degree. So I could move cities. I could go on vacation. I would still maybe work on vacation, but that’s not always a bad thing. I like doing certain things. I can control who I work with and who I don’t work with.

Understanding why you are being hired helps place you in the correct mindset to succeed.  (18:28)

The service you’re providing isn’t just the service. So if you’re dealing with a business owner, you’re helping them buy back a full extra day each month to go spend with their kids or take the weekend off. If it’s a local brokerage company, your job is to help deliver five extra leads every single month so that they get one or two more sales, which helps pay for your costs. 

So I think that’s where freelance writers need to think a little more about why someone’s actually hiring them, not what they’re hiring. Because at the end of the day, there usually is some end results that people want when they hire you. And again, it has nothing to do with semi-colons or paragraph styles or anything like that. 

How Brad gained confidence over time as a freelance writer (15:52)

I mean that’s, that’s those little tricks you start learning over time is what helps you become more comfortable with it. So it’s not that you become this like this crazy confident super brash person all of a sudden and you’re blind to reality. It’s that you, you have a longer pipeline, you have more leads in the pipeline, you have all these other things kind of figured out. So it’s like you’re hedging your risks and you’re hedging the downside as much as you can. And that’s what gives you the confidence.