
TCC Podcast #253: Successful Freelancing with Laura Briggs
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Show Notes
On the 253rd episode of The Copywriter Club podcast, Laura Briggs breaks down the foundational steps to catapulting your freelance business. Laura is a freelance writer and coach who helps aspiring and current entrepreneurs who are ready to live life on their own terms. Already have a successful business? You’ll hear concepts and ideas through a whole new lens. – Don’t miss this one.
Here’s what we talk about:
- Humans biggest question: “What do I do with my life?”
- Balancing a full-time job and growing a side hustle business.
- The best way to use Upwork and break into the freelance writing world.
- Whether or not you need a website in the beginning.
- Pitching to clients on weekends through LinkedIn.
- Your first portfolio and what it needs to include.
- Landing a 50k ghostwriting book project through Upwork.
- The pros and cons of Upwork and using it to its fullest potential.
- Why you need to personalize your pitches.
- How to overcome the “new writer” syndrome.
- How retainer projects help you with income projections and how to position yourself to secure the deal.
- Building your dream work schedule.
- When you should raise your prices. (and when you shouldn’t.)
- Creating a writing process that works best for you and your creative genius.
- Setting boundaries and tuning into the red flags.
- How to make decisions as a CEO and become an empowered business owner.
- Sales calls and being okay with the silence.
- What most freelancers are doing wrong and how to fix it.
- When you know you’re ready to level up.
- Delegating to others and creating time and space in your business.
- Creating a nonprofit around your core values.
- Offering services that are in demand and match your personality.
Check out the transcript below or hit that play button to listen in.

The people and stuff we mentioned on the show:
Kira’s website
Rob’s website
The Copywriter Club Facebook Group
The Copywriter Underground
Betterbizacademy.com
Full Transcript:
Rob: Being a successful freelance copywriter is about a lot more than just writing the right words for our clients. There are so many things to think about to do beyond the writing, things like finding clients, or pricing yourself effectively, setting up the right packages, things that our clients actually want to buy, and raising our prices as needed, figuring out retainers, project scope, all of that kind of stuff. Our guest for this episode of the Copywriter Club Podcast is Laura Briggs. Laura is known as The Freelance Coach. And in her business, like we do, she helps freelancers deal with these kinds of challenges. In a moment, we’re going to hear how she built her own successful business and then helping others to do the same thing. But first, let me introduce my co-host for today, since Kira is still on maternity leave, Jacob Suckow. Jacob is, I would call him an offer doctor. Jacob, I don’t know if you’ve got a better title for that or not, but he helps his clients really figure out their offers.
Jacob: Awesome. Well, hey Rob, thanks for the introduction, I appreciate it. I don’t know if I’ve ever called myself an offer doctor, but I might have to steal that after today. Excited to be here with you today, excited to hear what Laura has got to say.
Rob: Yeah. I’m looking forward to this conversation also. If you want to find out more about Jacob Suckow, you can find him at top-notchcopy.com, but don’t forget the dash. And one of the things, Jacob, I’m going to mention this, even though it’s not really live here, you’re playing around with this idea of a paid newsletter that you’re thinking about doing, talking about all the things about starting a successful solopreneur business. Maybe just give us like a one-liner for what that might turn into when it gets launched.
Jacob: Yeah, sure. So there’s a big gap in content out there for people like us who are just building something on their own. And typically, we get a lot of really great feedback on everything except financials, sales, pipeline, and behind the curtain marketing and growth strategies. And so that’s what we’ll be doing, 100% behind the scenes, full transparency look into QuickBooks, my pipeline, client work, and everything that I’m doing that’s either working or not.
Rob: That sounds really cool. I can’t wait to check it out when it goes live, we’ll keep everybody informed when it launches. So before we get to our interview with Laura, like last week, I’m going to switch things up just a little bit and talk about the Copywriter Accelerator. That’s because the Copywriter Accelerator, if we’ve timed this right, is actually opening up today. The accelerator itself is made up of eight modules, it takes about 16 weeks. We go through it not as a course, but as a program so that you’re going through with several other copywriters, figuring out things like business mindset, the kind of business that you want to build packages, processes, pricing, branding, getting yourself in front of the right clients, figuring out your X factor, and a lot more. If that sounds like something you’re ready to do in your business, check out the copywriteraccelerator.com. Like I said, it’s now open and the cart will be open until, I believe September 1st. We would love to work with you in the accelerator if that’s a fit for you and your business. So let’s jump into our interview with Laura and her story and find out how she became known as The Freelance Coach.
Laura: I started freelancing in 2012 and was able to leave my full-time job, I used to be a seventh grade teacher. And other people started following that story, and I got profiled in Business Insider, and then that led to strangers asking me about how I did it. And so eventually, I was doing all these one-on-one coffee chats, helping people, especially teachers, telling them how to get started, how to create samples. And then I realized that this would be so much easier if I just consolidated it in one place and had a website and a podcast and free resources that people could use. And so, I’ve been doing that since 2015. And I’ve worked with a lot of different freelancers. They’ve come through my courses or read my books or have been one-on-one coaching clients. And it’s been really interesting to see things that I’ve experienced also be validated by other people and get to see some of the trends that are coming before they really hit the marketplace in a big way. So it’s led to a lot of other speaking engagements about future of work as well.
Rob: So when you were a teacher, what was the impetus to make you think, “I’m not doing this anymore, I need to find something else”? And how was it that you settled on freelancing, writing and the stuff that you’ve ended up doing?
Laura: Well, teaching is an exhausting job. I have a lot of respect for every single person who is a teacher in this country, especially if they have made it to the retirement mark, because I don’t know how you did that job for 20 or 30 years and didn’t lose your mind. I was working 14 hours a day. Then I would go home and I would grade papers and I would do lesson plans for the next day. I worked in a very high needs district, I taught in downtown Baltimore. We didn’t have enough desks or seats for the students, we did not have enough books. I had to use my own personal laptop. It was really, really rough to try to keep up with that pace. I hadn’t studied education either, so I went in through a program that was very similar to Teach for America and had a total of six weeks of training to teach seventh grade. It was not enough, as you can imagine. And so I was really getting burned out. Honestly, it was another teacher of mine who inspired me. I had a professor in college, I took his contemporary literature class, and he pulled me aside after class one day with a paper I had written, and he said, “Have you ever thought about changing majors from economics to English?” And I was like, “No, I’m almost done with college, I’m not starting a whole new thing.” But that comment stayed in my mind. And so I thought, “Well, maybe I do have some writing ability that if I learned it and I finessed it and got at taking feedback, that this could go somewhere.” So I literally Googled how to become a freelance writer and read and absorbed everything I could.
Rob: And what were those first steps that you took as you broke out? Did you just leave teaching cold turkey, “I’m out, I’m doing something new”? Or did you transition out slowly?
Laura: I transitioned to a different job first. I was about to finish up the school year, and an old boss of mine reached out to me and they knew I was teaching because it was the job I’d had before I went into teaching. And she said, “We have another job opening up, we’ll wait for you to finish the school year.” And it was in marketing, so it was related, I’d be doing some writing. And I thought, “Well, this will be a good transition. I’ll do this for a year while I figure out what to do with my life.” Because I was in a PhD program at that time, I wanted to be a professor, I really thought I was going to go into traditional education, and teaching middle school just completely killed that for me, I didn’t want anything to do with education for awhile. So I took a job, that job doing marketing. I stayed there for 13 months. I started my side hustle at the same time that I started that job, but I wanted to give myself a real year to figure out one, was this even sustainable? I didn’t know if there were seasons to freelance writing, I didn’t know if this was something I could keep up with every month or if it would just be a side hustle. So my goal was to make it 12 months and really see what the revenue looked like and if I could make that decision to take the leap from there. And that’s when I left and went full-time in the summer of 2013.
Rob: Okay. So let’s talk about the balance then. You took on the marketing role. What did you start doing to create the side hustle in order to prove the concept?
Laura: I think the first thing was to figure out what types of writing are in demand, because as you know, there’s so many different routes that you can go as a writer, you can do sales copy, you can do SEO content, you can write email newsletters, sometimes it’s a blend of all these different styles of writing. So I wanted to find something that really suited my personality and the fact that I wasn’t a trained writer, I didn’t study journalism or communications. So I knew I was coming in with less experience than most people. I landed on SEO writing as the right fit for me. So my first step was to learn everything I could about that and to create three writing samples that were never published anywhere that I could use to pitch for jobs. I was really active on job boards when I first got started, I did land my first couple of clients on Upwork, which is a dirty word in the freelancer community if it’s a good place or not to land gigs. But for me, it really allowed me to break in and to get some of that important experience and feedback. So on the evenings and weekends, I was very actively pitching my business. I didn’t have a website, I was using my LinkedIn profile. I was using a Dropbox folder of my writing samples. And I spent a lot of time just marketing my business, just trying to land those clients. Most of them were one-off clients writing blogs or a website copy.
Rob: Yeah, let’s talk a little bit more about job boards. So we’ve definitely had other guests talk about Upwork, they’ve started on Upwork. Some of them have even succeeded in Upwork. And like you mentioned, it sometimes has a bad name in the freelancing community, partly because a significant number of clients are price sensitive there, that kind of thing. But having said that, there is a way to make it work. There are clearly copywriters, designers, others on Upwork who are connecting with higher paying clients, they’re retainer clients, those kinds of things. Can we talk a little bit about how you make that work? A lot of people will never be on Upwork or never go to the job boards because of the kind of work that’s there, but for some it’s really a way to get started. Let’s talk about how you did that and how other freelancers can be doing that today.
Laura: Well, I think first it’s worth saying that I still can continue to see success on Upwork as a writer. I’m not as active on there as I used to be, of course, because most of my clients are private clients and on retainer, but I also run a nonprofit where I train military spouses how to break into freelance work, and we consistently see that is an excellent way, especially for the writers and the virtual assistants to get their first experiences and to start building up that stable portfolio. The other thing to note about Upwork is that there are gems in there. One of the very first jobs that I landed on Upwork was a $50,000 ghost writing project. And so there are those clients on there, many writers lament that they’re hard to find. And that is true because if it were easy, every freelancer would be on there snapping up those jobs every day. You have to put in the extra effort to really use the search terminology to find the high end clients. But for new writers, Upwork is great because your clients are pre-sold. You don’t also need to sell them on the fact that this is a service they should invest in. They’re already on the site posting a job saying, I need a website writer, I need a sales copywriter. I know I can’t do this myself. I need someone to help me with the copy for my Facebook ads.” That’s one less barrier you have to overcome. Your only job at that point is to convince them that you are the right person for that job. It’s also great for new writers because the stakes are low. If you’re taking on a project that’s probably a one-time project or a limited engagement, you don’t know yet if you love writing as a freelancer. A lot of people are lured in by the possibilities, but they don’t realize until they’re in it, it’s a lot of work. You spend a lot of your time marketing your business, and then you have to deal with revisions, sometimes you have clients who are crazy. It’s work. So I think it’s a good way to test it out and take on a couple projects and say, “All right, I’m not viewing this as necessarily my profit-generating machine, I’m seeing this as, how can I get some experience here, see if I like it, learn what it’s like to work with a client, and leverage this into bigger and better things if I chose to do it?” So I think what’s most important on Upwork, I’ve hired a lot on Upwork as well, write a really compelling, personalized pitch. 85% of the freelancers on Upwork will not do it, they will copy and paste a 16-paragraph pitch that means absolutely nothing to the client. So really put time into that pitch and then also your writing samples. Clients will overlook lack of experience in general and lack of experience on Upwork if you have excellent writing talent. So it’s definitely hard. It took me, I know that the number was over 30 as far as how many jobs I had to pitch before I even landed my first one, but it can be a great pipeline. And even as an established freelancer, my having a profile on Upwork that other clients find when they Google my name, it does not hurt to have years and years of great feedback from clients there, even if they’re hiring me in other ways and never posted their job on Upwork. So I don’t take the view that it is the destruction of the freelance world, as a lot of people do. There’s some great opportunities there. And it’s all about knowing how to use that system, and also respecting your own boundaries. I saw a job this morning that was offering to pay $4 per 400-word piece of content and I just laughed as soon as I saw it, I was like, “This is such a joke.” Don’t get invested in it, don’t try to correct it or point out that this is a terrible rate no writer would ever accept, but you got to look through those and try to find the better jobs.
Rob: So you mentioned you had some samples that you created, three samples. What did you create and how did you use them as you started pitching yourself to get these clients?
Laura: I know I created a blog about life insurance because I was working at a life insurance brokerage at the time and I knew that would be an accessible thing for me. I also had spent a lot of time working in the legal industry, so I created two blogs just for a general attorney page. They were about as generic as can be like, five things you should do after a car accident. My thinking on the writing samples is if you have an inkling of a niche or an area of expertise that you have that you think you want to target with clients, create the content in your writing samples to match that. So what I would do is I would bid on every job that was relevant to my experience, it would have legal background, it would have financial or life insurance background. And then I would use those samples and say, “Here, this is an example of the style of my writing.” They don’t necessarily need to be published anywhere, like I said, I shared a Dropbox folder. I encourage our operation freelance participants to use Google Documents, to use Microsoft Word documents they add in Dropbox. With writing, you can really showcase a great piece, and it doesn’t need to be on a fancy website or on a portfolio page. So I use those same three writing samples. And of course they’re terrible. Thank goodness we all get better as writers because I don’t know why anybody hired me, they were awful. In hindsight. I’m like, “I thought this was good, these are great.” But don’t stress about that, you can always update your writing samples. So create something for a fictional company or as if you were going to work with a company that you really admire. It helps put that context into a client’s mind of your type of writing style and flow. So just try to keep it simple and create a writing sample for every type of thing that you think you may want to pitch. So you don’t need to write a whole book if you want to sell ghost written books, but create a sample chapter and create a sample white paper if that’s something you want to pitch, because you can get a lot of mileage out of those pieces.
Rob: You also mentioned that, and I don’t mean this to be a tutorial on how to use Upwork, but you’re sharing a lot of really, really good things here. You mentioned that a lot of writers don’t know how you search terms in Upwork in order to find the gems. Okay, so educate me, how do we find the really good clients using the right search terms?
Laura: Well, first of all, disclaimer, that not every client knows how to use Upwork either, so sometimes they don’t get their search parameters or the way they tag their job perfect. So to some extent, all pitching on Upwork is a little bit of a gamble because you’ll have clients who will tag their job as they want an expert, but then they’ll say, “My budget is $20 an hour.” Those two things don’t meet, obviously. But search terms are ways that you break down the massive volume of jobs that are on Upwork. So there’s thousands of them at any given time. It’s updating all day long with new postings. There’s categories, which of course are things like writing and translation, administrative work. You’re going to want to pick one of those kinds of categories to search within. Obviously, as a writer, that’s going to be the writing and translation category. And then I use search terms for things like blog, SEO, copywriter, even the word copywriters spelled wrong, R-I-G-H-T. You do have some clients who, they don’t know, so that’s what they write in there. I also use search terms for my industry. So I type in, legal, law, law firm, attorney, things like that. And then I will break it down by the category of writing and translation. And then you can even go so far as to say I want it to have this budget, or I want it to have been posted however recently, or not have this many applicants or whatever. There’s a tag on there about experience level. I always uncheck entry level, because there’s no point in even looking at a job post that specifically says entry level. So I leave intermediate and expert. You’re condensing the level of terrible jobs when you can weed out some of those entry level things, and they’ll still pop up. But then you use those different search terms. I use it to do a quick look. I’m not spending hours on there. I hop in two or three times a week. Is anything new posted that I need to take a look at? Is there anything even worth my time? And if there isn’t, then I hop off. I think that’s another mistake a lot of people make is they’re like, “Well, I’m spending four hours a day on Upwork.” And it’s like, no, that’s not what you should be doing as a new or an experienced writer. It’s a quick check to see what’s new and bid on the ones that are applicable. But yeah, use those search terms, it’s going to be different for every writer, but if you work in a particular industry, that’s a great way to narrow it down.
Rob: Yeah. That’s really great advice. Just one point of clarification, even as a beginner, you would still untick the beginning jobs and go at the higher level, or would you say as a beginner, I would still want to stay in those low-paying, well, they’re not all low paying, but those beginner jobs?
Laura: Well, I would say that the strategy would vary based on how new you are. If you’ve ever done professional level writing before, if you have clips, if you have other clients, you’re not an entry level writer. So what I might check if you’re new to the Upwork platform is uncheck expert because maybe you don’t feel like you’re there yet, or you don’t feel like you’re there yet on Upwork. What’s the biggest challenge is the overwhelm in the number of job postings, because you could spend all day sorting through them. And so I recommend using the search features to break things down and make it a little more digestible for you. So it’s worth scanning through them. For writers specifically though, I’ve noticed the vast majority of the jobs tagged as entry level are extremely low paying and they’re taking advantage of people who don’t have any writing training who really just want some experience. I told you about that one that pays $4 for 400 words, and that’s before the Upwork fee. And so you will have to sort through more of those things if entry level is tagged that you want it to go through that. That’s why I really use my first order of searching are the keywords and the category, and then I may check or unchecked those experience categories based on how many jobs pop up. If it’s been four days since my last search and nothing new is showing up in my search results, I might play around with that a little bit to see if I can just have some more things pop up and see if they’re a fit for me. But I think it’s just, continue to work on a strategy that exposes you to as many jobs as possible, and don’t waste your energy on the ones where the client is clearly difficult or not a fit.
Rob: Okay. Really good advice. Enough Upwork chat. Let’s talk about how your business evolved, after that first year where you were starting out proof of concept, clearly it worked. As you left your marketing job then, what did you do to grow your business?
Laura: Well, I had been spending 40 hours a week doing a full-time job. And so my freelance business was very much crammed into the fringe hours when I could fit it in, and simply getting those hours gifted back to me was a huge opportunity where I increased my revenue substantially. So from there, my transition became, “Okay, now that I have these hours back, how can I scale my business to a level where I’m not feeling overworked or burned out, but how can I get more of these clients on retainer?” That really became my number one focus, because I felt a lot in my side hustle, every month I was starting over at zero. I’d have to go out, I have to acquire clients all over again, I barely learn their guidelines and turn in their project, and then that project was wrapped up. So for me, that’s really where it became about, “Okay, how do I reposition myself to be a person who provides these services on a monthly basis?” Because I could see not only would that relieve a lot of stress for me, but it allowed cashflow projection because I could tell how much marketing I needed to do in the rest of the month, based on how many set clients I already had. And I still run my freelance writing business today just like that, over 90% of my clients are on retainers with me. And it makes my life a lot easier because I know exactly when I need to pivot or when I need to go out and acquire more business and things like that.
Rob: As you sudden engage with a client, then what does that pitch look like as far as like, “Hey let’s set up a retainer.” Are they coming in with the expectation that they’re going to be working with you for several months? Or is that something that happens as you’re talking to them about how you’re going to help them? What does that whole process look like?
Laura: I think you’d make your life a lot easier if you offer a service that obviously fits well with a retainer, email newsletter writing, SEO blog writing, social media copy, all of these things have a recurring need, and so it’s a lot easier to convince the client that it’s easier to just outsource that every single month. Of course, not every project fits well within that. And so you can choose how much of your business you’d like to be retainer based versus project based. And I know that’s a preference too. I’ve worked with a freelancer before who was a web designer and she’s like, “I want all my projects complete in two weeks or less. That’s my preference. I’d rather do a bunch of really quick turnaround projects and plan my life that way.” So you know you do have that option available to you, but I think the biggest part of it is have something that fits well with the retainer, even if you don’t have a perfect retainer package, you can offer a hybrid to your clients of, “Okay, we know you typically need X, Y, and Z every month, would you benefit from having several hours of my time,” whether it’s consulting or it’s creating one landing page, or maybe it’s two short emails in that time period, or giving them some flexibility to choose different things, I’ve found that works well with some clients to having a cap of, “Hey, our retainer is for $3,000 a month, here’s some different ways that this could look like if you choose to go forward.” But you will make your life a lot easier in many ways by offering a service that is retainer friendly to begin with. And most of them, it starts with a sample job. You do a good job on the sample job, and most of them know they need to outsource that thing on an ongoing basis. If they don’t, that’s when you want to bring it up to and say, “Hey I work with some of my clients on a long-term basis, you won’t have to worry about going out and hiring somebody else. I can work on these projects for you every single month. Obviously, I’m going to get faster at them. And I’m more of an expert in your industry and your business as time goes on.” So that benefits them. I think sometimes it gets positioned the wrong way as like, “Hey, I want to have clients on retainer because it’ll be easier for me, and I want to have ongoing revenue.” Make it all about the client and how it really benefits them to have you in their corner every single month.
Rob: And if I’m thinking as a copywriter, I want to work with more retainer clients, is there a business size that is optimal for these kinds of projects? I can imagine that mom and pops or very small businesses, single sole proprietors, they have the needs, but maybe they don’t have the money or maybe they don’t have the marketing direction. If the other side of the list you’ve got massive enterprise companies that maybe they’re using agencies for this kind of stuff, do you look and say, “Okay, X number of employees,” or there’s certain amount of income? How do you make a judgment call there?
Laura: That’s a great question because I’ve heard lots of other people have specific rules on, well, the company has to have at least a million dollars in revenue. To me, a lot of the times what it really comes down to is something that you can easily research ahead of time, which is how much do they value writing, because some companies may generate $5 million in revenue a year and believe that paying somebody five bucks per piece of website copy is fine because that’s how they’ve always done it, or they had someone in house that was getting paid $40,000 to do that job and crank out copy all the time. So it’s really more about how much do they value it, do they see that this is a service where it’s not just a deliverable, you’re really hiring an expert? Because you don’t want to get into an argument with your clients of, “No, I really do know what I’m doing. I’m following all these best practices.” So there’s a good balance that you have to walk there. I like the medium-sized businesses, and more and more, there’s some really fantastic solopreneurs and small companies that are generating seven figures in revenue. And that’s a great place to be because they don’t have the infrastructure to necessarily hire an agency. Their business still feels too personal to them to hand over to an agency, and they have the need as well. They have to continue producing a lot to have digital course launches and sell books, and all that kind of thing. So I like those what I’d call the high level solopreneurs. And then I also like those small to medium-sized businesses that have a decent budget and value the service, because I don’t know about anyone else, but I know for me working with some of the really big companies, there’s a lot of bureaucracy, there’s a lot of red tape, there’s a lot of this has to be approved by 16 departments before it can get published. And as a writer, that’s just maddening and doesn’t really feel worth it to me.
Rob: Yeah. And you didn’t mention this, but a lot of the enterprise companies too often have net terms, 60 days payables, that kind of thing, which can start to press a writer a little bit on their budget when they’re not getting paid for that work immediately. Let’s break in here and talk a little bit about some of the things that Laura mentioned. Jacob, I’m going to start with you, what jumped out to you from this first almost 25 minutes of discussion?
Jacob: There was a lot to break down in here, there’s a lot packed in. Kudos to Laura, but something that stuck out for me, especially in this first section, was that she mentioned, she decided on a service that she knew was in demand and suited her personality first. She took her time obviously to get her feet wet and get some wins under her belt, but when she backed in and knew that she was going to be doing a lot of work to scale, she decided that she needed to approach it like anything else we would do for a client and figure out where she could fit in best from a positioning standpoint. And I thought that was genius and something a lot of people can model.
Rob: Yeah. I think you’re right about that. A lot of us, when we start out as copywriters, it’s like, “Oh, well, I’ll just do copy, I’ll do whatever the client needs.” And the fact that she focused on something that she knew clients needed without making them figure it out is like you said, is genius. And having that thing that she could do that helped her identify who the right clients would be and then have something for them immediately, I think is a good first step that anybody can borrow, and using their own business and start out farther ahead than those of us who when we were starting out, it’s like, “We’ll just do whatever. We’ll just do whatever it takes.” And along with that, she was trying different things. The side hustle that she put together for herself, I think is another really smart approach, rather than having it all ride or die on the success of being able to land a client or two in that first month or two, having a job, a full-time job while she proves the concept of the copywriting thing, can I find the right clients? Can I figure out what they want? It gives you that safety net in case something goes wrong in your copywriting business, it gives you time to learn, not just how to write better, but the business side of the business, all those things that we talk about in the Copywriter Accelerator that I promoted earlier, all of that stuff, I think her approach there was really smart.
Jacob: Yeah. 100%. And something that I’ve noticed about other folks who’ve build their career as a side hustle, they might not start under the same amount of pressure as other folks who dive in full-time right off the bat is that that space allows you to be so much more strategic in the long run. She said that something she constantly went back to was thinking about, how do I reposition myself to be a person who provides the kind of services that I want to offer? And it’s hard to do that when you’re constantly just worried about replenishing pipeline, and figuring out where the next deal is going to come from. You don’t get a chance to realize where your strengths are at and pay attention to where the market’s actually showing you that it needs more help.
Rob: Yeah. I think that’s a really astute observation and when we started talking together, I didn’t have a plan to talk a lot about Upwork that wasn’t anything that we discussed beforehand, but she had so much, really good information to share, not really about Upwork itself, but really how you succeed as being a copywriter. Obviously, you can do it on Upwork. And what she shared about the specifics of Upwork, I think is really good, but a lot of that stuff applies to how we launch our business with clients outside of places like Freelancer.com or Upwork or whatever. You wouldn’t copy and paste a 16-paragraph pitch to a real client or a referral client that’s coming from somewhere else. So obviously the advice that she gives about stuff not to do on Upwork matters, and it matters to the way that we conduct our business any way that we build it, target a niche, find that thing that is in need, work in promoting your business the same way that you would if you’re on Upwork or off Upwork in order to succeed.
Jacob: Yeah. I agree entirely. And I’ve known quite a few folks who’ve been massively successful on Upwork. We’re talking run in 10, $15,000 a month, student things on there. And what they all have in common is exactly the same as folks who are doing the same numbers off of any platform, or on any other different platform, or no matter where they find their clients, is they understand first and foremost who they’re serving, and then they do all of the background research and work to tailor their pitches to what the pains of those specific folks are. And then they show up and say those on a place where they know that the clients they want to work with are pre-sold, is how I think Laura mentioned it. And that’s not tied down to Upwork, that’s Facebook groups, that’s networking events, that’s different kinds of webinars and Slack communities, and anywhere that you can be on the internet, it’s just all that matters is that you know there’s folks who have a need for what you provide there and you know how to speak to them.
Rob: Yeah. I think the big takeaway for me here, my piece of advice here is if you were just listening to the last 10, 15 minutes or so while Laura is talking about all this stuff to do on Upwork and you thought, “Well, this doesn’t really apply to me,” maybe go back and re-listen to what she was doing and say, “Okay, how can I use the same approach the way that I want to reach out to clients off of Upwork, or with my referrals, or on Facebook,” or wherever it is that your clients are, because what she suggested to do will work anywhere.
Jacob: Let’s go back to our interview with Laura to find out what our business looks like today.
Rob: You mentioned after doing this a few years people started asking you for help doing it in their business, you’ve changed your business a lot. What does your business look like today as far as how much you write versus how much you coach and versus all of the products that you’ve put together? And you’ve got a ton, you’ve got like 16 courses, something two courses, you’ve got three to four books. You’ve done a lot. So how does that all break out today?
Laura: Today my business is probably about 50/50. I actually track my time every week, because I used to be an overworker and was addicted to work and have to be very specific about the time I spend on my computer. So I use a tool that tracks what I’m doing and how much of it. I work about 30 hours a week. I would say half of that is on my freelance client work, and then the other half of that is on what I would consider my coaching or course business. That’s got my books, my podcasts, my courses. I run a free community on Facebook, I have an email list of freelancers who follow me. And so I treat those as two separate buckets. They’re pretty much even now, our freelance business still generates more revenue than the other side of my business, just because I’ve had some client… I have one client who’s had me on retainer for eight and a half years and I have another few clients in the four to five-year space. And so it’s hard to serve that when you lock in those good clients. But that’s something I’m working on so that I have that flexibility to decide how much freelance work do I want to take on and be responsible for versus how much of my time is spent doing things like thought leadership or doing a podcast like this and coming to talk with you.
Rob: I’m curious about those long lasting clients, oftentimes we’ll see retainers last a year or two years, like four years, five years, that starts to be pretty incredible, obviously speaks well of you and the work that you’re doing. But I imagine that you’ve raised your prices with those clients more than one time over the course of that time. Will you tell us the approach that you take as you do that, what’s that conversation look like and how do you make it a net plus for everybody?
Laura: Yeah. So the first thing is don’t raise your prices too often. I’m a huge advocate of getting paid what you’re worth and raising your prices, but it should not be something that’s happening every couple of months, obviously, if you’ve got people on retainers and especially if they’ve worked with you for a long time, because the way that I like to think of it is I’m saving a lot by not having to go out and market for new clients. When some of those new clients may be shorter-term projects, or it might be that retainer that lasts six months or a year or so, I always think about how much easier is my life because I have these clients. So I never want to make them feel like they’re being hit too often with a price increase. I usually let them know several weeks in advance, and I usually give them some type of offer or incentive, or something to help them prepare for it. And I usually do it around the same time every year so it’s not a surprise. It’s not like, “Oh, it’s randomly February and Laura’s raising her prices.” They always know that could come in the summer or that could come in as January gets closer. People are thinking about that anyways and it’s easy to just say, “My prices are going up on January 1st.” So I give them an advance notice. If they’re a really great client, I might offer to keep them at their same terms for a little bit and gradually move into that other place, or if they’re going up and I think my prices are going up and I think there’s a possibility they might leave, I might use that to get clarification on that, figure out like if me saying that my prices are going up is going to drive them away. I have some advanced notice to do some marketing so that I can replace that client as well. But I’m a big fan of not necessarily justifying it. You can if you want, but it’s weird what clients think should cause you to raise your prices. I’ve done a lot of different things in the last couple of years, but for some reason, three of my clients fully expected me to raise my rates after I did my first TEDx Talk. And they all reached out to me about it independently and were like, “Oh, I thought I’d have to pay you more.” And I was like, “Why that particular thing? What was it about that that made you think that my prices were going up?” So people have different perceptions of stuff. I usually just say, “My prices are increasing on January 1st, this is what it’s going to look like. Here’s your options to deal with it? We can wrap up what we have going on and conclude, or this is the date on which the things will take over.” And if they’ve been a really good client, I will often try to give them some type of incentive just to make it feel a little bit less like, “Hey, I’m raising my prices.” And I want to respect the fact that they’ve been with me a long time too.
Rob: When you talk about incentives, are you talking about like three more months at the regular, at the same price and then you move it up or are you adding things to the retainer deliverables, that kind of thing?
Laura: Yeah. It can be simple things. Maybe if it’s a client that I really liked, like the client I’ve had for eight and a half years, I think I’ve spoken to them on the phone four times in that period. So he causes me no additional stress and pays his bill on time every month. So that might be something where I’m like, “Here, I had this idea for some social media copy to go along with the next four blog posts. I’m just going to throw that in while we transition to this new retainer.” So it could be discounts for an extended period of time. I’ve also rolled out a referral program whereas I’m making that transition and I’ll tell them like, “Hey, here’s a way to get some money back, I’ll give you 10% off your next invoice, or I’ll give you $200 cash if you refer any client that books $1,000 or more monthly retainer.” So there’s different ways that you can try and play around with it just to make it not seem so much like you’re just coming at them with a price increase. And my other favorite tip for this, and I’ve coached a lot of my freelance writing clients through this, never just go into it if it’s one of those off times, but you’re like, “It’s October and I have not raised my rates in forever with this client,” or they’re about to resign a six-month or a year-long retainer. Don’t just go in and say, “I’m raising my rates.” This is a great opportunity to recap the work you’ve done together. So talk about some wins. With my SEO freelance writers, I tell them, “Go back, grab their rankings, tell them how many blogs you’ve published. How many of them are ranking in the top 10. If you wrote lead magnets for them, how many people have downloaded that lead magnet?” You want to butter them up and talk about like, “Hey, here’s all the great stuff that your company accomplished in large part due to the work that I helped you with. And by the way, my rates will be going up.” It doesn’t seem as much like you’re just talking about money, and it puts them in a more positive frame of mind to think about the value you bring to the table.
Rob: Okay. That’s super smart. I like that. Let’s talk about your business today then, the coaching that you do, some of your programs, what does that look like? I’m throwing a bunch of questions, I guess, together, but how many people are you coaching at once like one-on-one? And how does that play out as part of your business?
Laura: I have two different ways that I coach with people, one is an all-inclusive coaching, which has done over the voice app, Voxer. That’s basically, you can send me messages between traditional business hours, Monday through Friday, and I usually respond to those messages within 24 hours. That’s a three-month engagement. That’s really for someone who’s working on multiple things at once and has a lot of things they’d like to accomplish during that period. I usually only work with one to three of those clients at a time because of the other things that I’ve got going on, and it’s really hard to be that involved in someone else’s business m