Interview: Tips For Freelancing Success with Laura Pennington-Briggs – Part 1

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A few weeks back, I did a Facebook Live interview with Laura Pennington-Briggs, a freelance writer and copy editor. She had some great tips for freelancing success, and I’d love to share that interview. This blog post is a bit of a long one, but the nuggets Laura gives are so good that it’s worth the read!

So, I’ll release this interview over the course of three blog posts. Here’s the first bit; stay tuned for the others in the coming weeks!


Melissa Froehlich: All right, hey, listeners. Hey, Happy Monday, I am here with Laura Pennington-Briggs. And she has so kindly taken time out of her very busy schedule to share some amazing insight, tips, and tricks with us. We’re going to talk about her journey into the freelance space, and how she got to where she is. And, we’ll discuss the very successful business that she has established, along with the release of her newest book, which is incredibly exciting. And we’re going to focus on Upwork and LinkedIn today. So, those of you that are already freelancers who are looking for some tips and tricks to uplevel your strategy in your current business, this is for you, as well as those of you who aren’t even sure how to get started.

With freelancing, it’s your lucky day. Feel free to drop your questions in the comments. So again, this is a fantastic opportunity to talk to somebody who is very established in the role of freelancing and has created a really successful business model and coaches lots of people. So we’re so fortunate to have you, Laura! I’m going to turn it over to you: tell us about yourself, your journey, and how you got started.


Laura Pennington-Briggs: Sure. So I used to be a teacher. I taught seventh grade; I was supposed to teach in Baltimore City, but it was a school district that didn’t have a lot of resources and support for teachers. So I ended up teaching everything: US history, reading, geography, a little bit of math, and personal finance. I knew that wasn’t really going to work for me as a career. 

This wasn’t going to work because of the level of stress and exhaustion that I was experiencing, but also because my then-boyfriend, now husband, was graduating medical school and kind of moving into another position within the military. He was in the Navy for 14 years. 

He enlisted at 17, got out to complete college, and then went back in for medical school. After that, he worked six years as a physician in the Navy, so I knew that the moves were going to start; we’d already moved a couple of times while he finished med school. And in total in the last 10 years, we’ve moved eight times for his career. So we’ve done a lot of moving around, and I could never have made it as a teacher or something that wasn’t flexible. 

So I started researching in 2012: how to do freelance work. I tried a lot of different stuff: worked as a VA, worked as a freelance writer, and I’ve been full-time writing since 2013, working as a freelance writer for companies all over the world.

I do a lot with law firms and the digital marketing agencies that help law firms. But I’ve also worked as a Project and Content Manager for Microsoft and Truecar. And now, I’m taking on lots of opportunities that have sort of opened up the longer that I have been freelancing. And now I try to help other people start or scale their freelance careers because I did not have a lot of resources when I got started. So I learned a lot of things the hard way. And I’d like to try to make it easier for other people to figure out what freelancing is all about. I want to help you figure out how to make it work for you, especially if you’re a military spouse; you’re already juggling a lot of things and it can feel like the deck is stacked against you when it comes to careers.  

We know this because we’re constantly moving for our spouse’s job, starting over in a new place. And it’s just hard, especially if the area around the base where you’re living is saturated and you know, you have all these different gaps on your resume. It can be really hard to have a traditional career. 


MF: These are all excellent points. So, how long would you say it took you to really start making some significant income? In your business when you went to freelancing full-time, and on top of that without going too deep, how did you figure out your ideal clients and who to work with? Because you mentioned some pretty niche markets there. 

LPB: Yeah. So I left my teaching job and I took a job in an insurance brokerage, where I worked for 13 months. During that whole 13-month period, I was doing freelance writing as a side hustle. My first goal was to break $1,000 a month, which I did in my first month. And then my second goal was to hit $3,000 a month that was where for whatever reason, I was like, that’s the number where I’m going to start to feel like this is doable full-time. So I stayed for a solid year so that I could track my income. I wanted to know if there were slow seasons, I wanted to know if this was sustainable. I wanted to have a year’s worth of data so that I could feel prepared to jump full-time. So it was a very busy part-time side hustle for me, and I got to the point where I really could not do my day job anymore because it was too hard to balance all of these deadlines. 

So when I left to go full time, I tripled my revenue and broke through the six-figure mark. So for me, it was a real blessing that I’d had all that experience and had scaled it slowly. And it definitely meant that now that I had a full day every day that I could focus on my freelance career, I was able to earn more income.


MF: Awesome. So, based on that, would you have done anything differently as far as like, the beginning stages: like how important was the goal setting? Would you have gotten more clear? Like what are some tips for people who are just getting started?


LPB: As far as that part goes, I really recommend having some sort of a financial goal in mind and it doesn’t matter if it’s small: if it’s like $300 a month, $500 a month. It helps keep you accountable to do the marketing because when you start your business, you will spend 80-90% of your time marketing and trying to get clients and a very small percentage doing the actual work.

Over time, that should flip to be the reverse: where I spend 90% of my time doing client projects and only 10% marketing. And I just realized I forgot to answer your other question in the last question, which was figuring out what it is that you like to do or whether or not you want to niche. Some of that is practice. I took on some jobs where I did just about everything. When I started as a freelance writer, if someone offered me a paying gig, unless they seemed awful, there was a good chance I was going to take it. I learned what I liked and didn’t like and also where I didn’t have a lot of competition. So for example, I did a job writing about software and IT technology, and I hated it. So I was like, I am never taking another client like that. But I really enjoyed working for attorneys and working in the law. 

There’s a lot of niches that are really profitable in the sort of freelance writing world. CBD is a big one right now, lots of companies popping up in the CBD oil space, that need content (medical, legal, financial), those are probably the big heavy hitters as far as being very profitable, but you can get paid to write about just about anything: gardening, pet care, being a parent. There are clients out there sort of across the board. So part of it for me was just practice and seeing where the demand was. 

You can check out different job board sites to see what kind of content are people asking for, they’ll usually say, like, I’m looking for someone with experience in fashion, I’m looking for somebody who’s a grant writer who you know, knows what it takes to get government money. So you’ll start to see trends of like, this is something that might interest me, maybe I should educate myself a little bit more about it.


MF: I think we’ll transition into talking about the where, and, and then we’ll talk about your book, only because you’re making me think of lots of great questions here. So that said, you mentioned job boards, but we’re also going to talk today about LinkedIn and Upwork. So can you give us the pros and cons? Is there one that is better than others? What do you tell people when they’re having trouble? 


I know just one woman in the UpLevel Lounge shared with us that she’s started freelancing, but she’s hit a huge roadblock in finding clients. How do we all get past that roadblock? So talk to us about that. And what is your experience there? 

LPB: So a couple of things. The first is the easiest place to land paid work as a freelancer, when you are just getting started, like literally, maybe you’ve had one client or no clients, is to ask people in your circle. Now you might not be offering your ideal thing. But I often tell new freelance writers, go post on your personal Facebook. Hey, I don’t know if you know this, but I just launched a career as a freelance writer. I’m helping three people revise their cover letters and resumes this week for a discounted rate. 


You’re much more likely to get someone who’s interested in hiring you when they know you already and if you pitch something that almost everyone needs, right, like a cover letter, or if you’re pitching entrepreneurs an ‘About’ page on their website or something like that. So, that’s the easiest place to get started. 


Upwork is a great place to find job leads: it’s very competitive, it’s gotten more competitive, and it’s gotten tougher to get into Upwork. And you have to sift through a lot of jobs that are what I would consider low quality. So lots of people who want to pay dirt cheap; there are great, amazing clients on Upwork. I’ve landed a $50,000 contract off Upwork, numerous $25,000 a year retainer clients from Upwork, etc. On my jobs working for Microsoft and Truecar…they were both through Upwork. 


But you have to be willing to sift through all those jobs. And when I got started, I knew I had to pay for extra what they call “connects.” It’s like bids that you spend to submit a proposal. You can’t always guarantee if a client is ready to hire or wants to hire you. So it’s a bit of a gamble to kind of learn; like there are even jobs now where I’ll submit a proposal and I’m like, I’m so qualified for this. And I’ll never hear anything from that client or they’ll hire somebody else. So it’s always going to be a gamble. 


That’s the downside with Upwork is that it’s competitive, and you kind of have to figure out how to work the system. I’ve definitely figured that out over the years, but I remember at the beginning, it was kind of like, I’m just gonna throw spaghetti at the wall until I figure out exactly what sticks. The benefit of Upwork is the clients are pre-sold, they already know they want to hire a freelancer, you just have to convince them that it’s you. So when I find somebody on LinkedIn, or like, bumped into somebody in an elevator at a conference, I might have to tell them, here’s why you need blogs or website copy. 


Here’s why, you know, ranking in search engines matters. There’s a whole educational piece I have to do. Whereas on Upwork, the clients pretty much know what they want a lot of the time, and I just have to show them that I’m the right one to do it. 


LinkedIn requires a much more proactive approach on your part, you need to be regularly interacting on LinkedIn, you need to be posting your own content. I post once a week kind of my insights on copywriting or in the legal marketing industry. I always do longer blogs for this platform. 


Also for LinkedIn, I’ll also do shorter posts. several times a week: 200 to 300-word posts, but it’s all geared towards my keywords. So I use words that my clients would use: “copywriter,” “legal writer,” “legal content writer,” and “legal SEO writer.” And I’m putting that into my profile, my blogs that I write my short content. So it’s much more of a longer game with LinkedIn. However, I’ve found that it really benefits you on the other end of it because people reach out to me, I usually have two to three people a week reach out to me and say, Hey, I’m hiring a writer. Is this something you could help with? 


So I never regret doing all of that work. I think that LinkedIn is the most underutilized platform for freelancers. A lot of people don’t want to put in the time and energy to learn it. But that’s where a lot of the best clients are hanging out. LinkedIn is full of business professionals, (i.e. CMOS & CEOs). I can email the CEO of McDonald’s, he’s probably not going to open my email. But if I write a really crafty unique pitch, just to connect on LinkedIn, there’s more of a chance that he might at least open it. 


Sometimes, especially if your prospective clients are hanging out on LinkedIn, they’re just more open to you commenting on their content and connecting in that way rather than kind of hitting them up in their inbox or trying some other method. So it is a lot of work, you have to hear no, be ready to hear no hundreds of times or thousands of times, or get no response very common. If you’re hearing that repeatedly, try to hire somebody to help you with your pitch or your samples. 99% of the time, when you’ve pitched yourself 100 places and landed nothing or got no response, there’s something wrong with the pitch and or the sample. So you want to make sure that, if you invest money in anything, put it there; you don’t need a website, you don’t need a lot of other stuff. 


If you are getting stuck and you’re not getting hired, that’s where I would kind of direct the money. Okay, that’s huge in itself because I think we all get caught up with the shiny objects of Oh, well, it must be my website or and I’m always saying no, no, no, no, no, there’s like always a fundamental piece. 


MF: But that being said, Do you coach people who need help with that? Or do you have recommendations? Tell us about that. 


LPB: Yeah, I’ve helped a lot of people with their pitches. And first of all, there’s no shame around it. I’ve worked with six-figure freelancers who are like, my pitch isn’t converting like it used to. And usually, it’s just a couple of tweaks we can make. And, you need to align it to the platform too. So like, in general, I plot, like the way that I pitch on Upwork is it’s going to include a lot of the same information as what I might write on LinkedIn. But on Upwork, I’m totally trying to convince them to hire me like immediately, I’m trying to beat out my competition. So there’s a little bit like a tweak that you can throw in there. So yes, I do help people with that. And what is so important why I say like, whoever you hire, hire somebody if you’re getting stuck at that point, because if you have a great pitch and great samples, it will open tons and tons of doors and most of the time. 


Sometimes, it’s something small like your pitch is 15 paragraphs long, and no one’s reading it. So if you can tighten it up and make an impact real quickly, there’s much more of a chance that it will get opened. But yeah, don’t waste the money on the website. You don’t need to pay for LinkedIn Premium. There’s a lot of stuff that you can just say, “Hey, I’m bootstrapping it.” But if you can get somebody to get their eyes on your pitch, if that’s not working, investing in those resources can be huge, because you can take that run with that and it can pay back your investment like many times over.


MF: So a couple of things I want to back up and discuss. One commenter asked, when we are talking about Upwork, She said she’s heard the same about Fiverr. So can you shed any light? Because a lot of people hear it’s the same. They’ve tried Fiverr, and they’re getting stuck. Do you have experience with Fiverr? Or is there a reason you don’t love it? 


LPB: Okay, I don’t love it. And I promise I’m not just upset about it because I got rejected from Fiverr Pro. Truth is, I applied To like every freelance platform I can, the purpose of doing that is because I want to see how hard it is for a beginner to break in. So if I submit my best writing samples, and it’s like really, really tough, or I get on the platform, and there are no jobs, I try to tell my community of freelancers about that, because I don’t want them wasting time. So when you pitch to a market that is largely built off of selling things for $5, it’s very hard to show value to your potential clients. Now there are great freelancers on Fiverr. I just hired a voiceover artist who charged me nowhere close to $5. He charged me $100 to record something that was two minutes, right; I had a video editor that put it all together for almost $200. So there are clients who are willing to pay more, but usually, that’s because the freelancer on Fiverr has built out their experience and has tons of positive reviews. So Fiverr can be good, but when you think if I’m going to offer something for five bucks and then Fiverr is going to take their cut, what kind of a client is willing to pay $5 for whatever it is that I’m doing. So, Fiverr can be a difficult one.

Upwork still is going to have cheap clients but in my experience, you’ll have cheap clients and then you’ll have clients who are really willing to pay for quality.  It’s “Do you have the patience to sift through the crap jobs and ignore them and not get your feelings hurt that someone is trying to pay that little or that freelancers are bidding for that little and find it the other way around?” 

So there are other freelance job board sites out there too. But I think that Upwork is, even though it’s competitive to get in it to me, it’s like, above Fiverr a little bit just because they have so many different people that are putting jobs on that platform and such great variety and every day you’re going to see like hundreds or even dozens of jobs that are posted there. 


MF: Awesome. We have another question. Donna was asking what types of samples? So Donna is newer to the freelance space, she’s hustling. She’s doing an awesome job. But same thing like,  What should she create if she was going to focus on one thing? 


LPB: Sure. So your samples should be aligned to what you would ideally want to sell a client. When I got started, I had never been published anywhere as a writer. I did not study English communications, journalism, none of that. But I said, if I’m selling blogs, I need to have a handful of great blogs to sell my clients. Now the only people who will struggle with samples are virtual assistants because you can’t really have samples of your work. If you’re a virtual assistant, try to hire or try to get a handful of clients, maybe people who know you personally, who you can give them a discounted rate like say for 100 bucks. I’ll do however many hours of work and that can really get you some testimonials.

If you can’t necessarily have samples, that’s one way to get around that. So if you’re any other type of freelancer, if you’re a graphic designer have a couple of logos on hand, if you’re a website designer have an example of your own website or someone else’s site that you built-in WordPress, or Squarespace, if you’re a writer, have articles or blogs, even an editor asked if anyone in your network is a college student, and you can edit their paper for free if you can use it as a sample and then turn on track changes and use that as your writing or your editing sample. So that’s what I mean when a client wants to hire you as a freelancer, they want to know that you know what you’re talking about. So even if you’re never paid to create the sample, try to make a really good example of what your work looks like. Because we want to showcase that to the client so they can open it and go, Oh, this is what I’m looking for. Or I really like this person’s logo design skills or voiceover artists might have a 32nd clip of them talking, for example, so you don’t have to make some massive big projects.

If you want to write ebooks, you don’t have to create a 50,000-word ebook; create one chapter. And that’s your sample. So that’s what I mean by sample. And it’s a really great way to help clients decide if you’re the right one to work with. Because if you don’t have samples, it’s hard for them to tell the quality of your work. That’s super helpful because I think that is it. We don’t know what other people are producing. So you have the overwhelm of like, Oh my gosh, am Is my sample fancy enough? You worry that you have to have enough samples, but it’s proof of concept that you actually can produce something versus just you have this fancy idea of being a freelancer, but you’ve actually never done anything. So it helps the person hiring weed through as well. And you don’t need a lot a handful and if you’re if you have an interest in a particular industry or niche, let’s say that you know, you worked as a dental hygienist for 10 years, maybe you’re and you want to try freelance writing, maybe your first sample is about like 10 misconceptions about going to the dentist or five ways to know your kid is ready for braces, right? Something that you know

Where you can showcase your own passion, interest, and expertise. But you don’t have to feel like Well, I haven’t been published anywhere. I’ve never sold a logo before. Make a sample that just kind of showcases in general what your work would be like. And if you’re, you know, if you’re like, well, I don’t know who I would pitch for. Imagine a company you respect. If you want to be in sports writing, you might say, like, here’s a sample blog that, you know, maybe would be published on Nike. It’s not actually published on Nike, but I wrote it as if Nike was my client, right? So that’s a great way to get around this challenge of “but I’ve never created work.” So how do I have samples type of thing? That’s awesome. And that also goes back to something I talked about a lot is just showing up with confidence. So hey, this hasn’t gotten published on Nike yet, but I wrote this because I think it would be fantastic. So let me show an example of that. 


MF: So what about the writer’s work platform? Donna is asking; I don’t even know what that is. 


LPB: So yeah, that’s another platform. There’s a lot of platforms out there specifically for writers. A lot of them have a dangerous reputation for being content mills. Now what makes a content mill different from a freelance job board is that the content mill is setting your price. They are determining how much you are worth per word or per article, rather than you saying, these are my rates. And a lot of times what happens is they can be really picky clients. And so they tend to pay lower, they might pay like two or three cents per word, for example, and then they’ll have a lot of revisions. And so it’s a lot of work to do sometimes for very little payoff. But if you’re a beginner, it can be a good place to get some practice. If you’re not relying on this for your full-time income. If you’re like, you know what I have like five hours a week, I want to try it. I want to see the process of writing an article getting feedback, incorporating revisions, see if this is even for me, it’s a low-risk way to try things out.

And get started, a lot of people struggle to break away from those content mills that they become kind of reliant on. That’s how you do things. So it’s important to set a goal of like, I’m going to do this for one month. And if it’s not paying me well enough, I’m going to leave after one month, because then I’ll have more samples and more experience and more confidence to pitch myself in other places. 


MF: That’s super good advice. Well, I hope that answered your question, Donna, thanks for asking, because that is really good to know the difference. 

Stay tuned for Part 2 of our interview!


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