Have you been freelancing for a while? Are you ready to level up?
In this episode, Kaleigh Moore and Michael Keenan skip the basics and get right to the techniques and tactics you can use to become an advanced freelancer.
+ “I was thinking, “Okay, I’m at the point now, where the business development side of things—it’s going really smoothly. I’m good at that I enjoy doing that piece, what things can I do to make the actual execution piece more efficient?” –KM
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+ “You never feel like an advanced freelancer.” —MK
Kaleigh: Oh, hello, we’re back!
Today we are talking about premium freelancing and stepping up your game and [giving] advice [to] more advanced freelancers. So stepping away from the more generalized folks who are getting started and speaking a little bit more directly to the folks who have been at it for a while, [and] are ready to level up.
What are the things they need to be thinking about doing? And what are some of the things that we’ve done over the course of our careers to get to the next level?
Mike, I want to start with you and ask, first of all, how did you know when it was time to start taking things to the next level? Did you reach a certain point in your career? Was there a shift that happened? Was it a benchmark? Talk to me.
Michael: Alright, that’s a great question to kick off with because I was going to ask you what defines an advanced freelancer. But this is actually a more pinpointed way to define it.
I think it differs by industry. Also the capacity that you can take on as a sole person and how many projects you can take on—how many clients you can take on your own.
You never feel like an advanced freelancer. But [I] started noticing around the 150 thousand 200 thousand a year mark. It was around there that I noticed, I’m teetering [on the edge] of becoming [either] an agency or just being myself. It was in that moment where I noticed that I was delegating out a few tasks and kind of like playing around with the idea of agency model.
(Mind you, I also had an agency, so I was familiar with how agencies are run.)
That’s when I was like, “oh, okay, I’m making, around 200K right now a year, and I’m overloaded with work and I’m delegating out tasks. So maybe this makes me an advanced freelancer.”
“It took everything out of me to get to this place where I was like, ‘oh, okay, I’m not just taking assignments anymore. I’m managing assignments.”—MK
Kaleigh: How many years did it take to get there?
Michael: I would say like five years, five or six years until I really broke the mark for that income level. And [that] also came with learning more about my craft over time and fucking up and getting fired from clients and firing clients. It was like a whole mess to get up to that [point]. It wasn’t like I just turned on the dial one day and I was like, “I’m advanced.”
Kaleigh: I’ve arrived.
Michael: “I’ve arrived. I arrived here at this advanced freelancer thing.” But it took—I literally have cried—it took everything out of me to get to this place where I was like, “oh, okay, I’m not just taking assignments anymore. I’m managing assignments.”
Where was it? Where was it for you? Where did you start to feel like you were transitioning out of [being] 18 [different] peoples’ employee?
Kaleigh: Similarly to you, I feel like I reached a breaking point where I was like, “wow, I am really busy all the time. There’s a ton of demand for the work that I’m doing. People seem to know me in the space that I work in.” So the Referral Engine is really going strong.
I also started delegating things out. Did it really, really slow and kind of stair stepped things. Also [I’m a] major control freak. So I was like, “I have to do everything.” So I started with baby steps.
I’d be like, “Okay, well, I’m gonna get help building my briefs for these clients and help with the research piece.” And then I was like, “Okay, I’m gonna get help with a first draft just to kind of speed up the process, so I have a jumping-off point. And I’m going to do the briefs because I’m super efficient at that.” And then I was like, “Okay, I’m going to outsource the editing piece. Because I’m spending a lot of time doing kind of nitpicky grammatical type edits, I could surely hand that off to somebody else who’s really well-versed in that.”
So really just started getting to the point where those pieces of the puzzle were coming together. And like you, I was thinking, “Okay, I’m at the point now, where the business development side of things—it’s going really smoothly. I’m good at that I enjoy doing that piece, what things can I do to make the actual execution piece more efficient?”
So for me, I would say that was probably about four years in, and I don’t think it was really a specific income or earning point of view that made me do it, it was more, “I am so stressed out, and I have way too much on my plate. And if I don’t do something, I am going to fall to pieces.”
I think [when] you’ve reached that point where you’re like, “Wow, this is really great. This is so amazing. But also, if I don’t do something differently, I’m going to die.” That was it for me.
Michael: I hope you have some tips for us to not die. I’m a little scared.
No, I think that’s a great point. I feel like I became an advanced freelancer when I looked inside. When I was in the beginning, I didn’t pay attention to my weaknesses, or my strengths. I was just like, “I’m gonna do everything, I’m going to appease every single person out there.”
It was when I started looking at, “What are my weaknesses? I’m not a good editor.” So I started hiring editors to edit my work. Also, where am I spending the most time? Research. What parts of the research can I get out to other people? I can do interviewing and talking with sources, but maybe there’s someone that can do stats roundups that I can use in the articles, or dig through publications and pull out fun facts, and [look through] recent news [and find out what’s] going on.
It’s definitely when I started looking at my strengths and weaknesses and seeing where I had the money to delegate out to was when I self-qualified as an advanced freelancer. Put it in the lights, you know, whatever that means.
So the question is, how do you, Kaleigh, build your workflows? What [does] your workflow look like from beginning to end? And how can people replicate that type of success?
Because I know, just from knowing you, you’re very good with your workflow. You have it to a tee and super tight. I need your help, too. So if you could give us a little insight as to how a freelance workflow works.
‘How can I play to my strengths? How can I delegate the things that I either find really tedious or that I’m not super great at?’ And I think that really enhances the outcome of the material as well.—KM
Kaleigh: I would say, first of all, I never wanted to have an agency. I feel like the agency models, [are] not super aligned with what I want for my day-to-day. I don’t want to be a manager. I still want to be very hands-on with the work that I’m doing and the people that I work with. So that just felt like a level that I wasn’t interested in and I still kind of wanted to keep my fingers on things. Because again, control freak.
So for me, my workflow is very much just like, “What are the things? How can I play to my strengths?
I really like editing, polishing, doing a context edit when I have a first draft, and poking holes in and saying, “How can we make this better? How can we go deeper here, this is missing, we need to pull in examples from X, Y, and Z.” So my role [now], I feel, is not only am I developing a really thorough brief to help the writer get that first draft kicked out. I’m doing a lot of the kind of heavy lifting with brief development, early research planning, developing outlines, [things like that].
What’s happening now is, I’m more of a, “let me just put my hands on it and make it what it needs to be.” So it sounds like I’m Jesus saving the content, which is not what I mean.
Michael: You’re making it the Kaleigh Moore content. That’s the point.
I’m gonna jump in here real quick. I think that’s the big difference between whether you’re deciding, “Do I want to be an agency or do I want to just be myself?” Because agencies, in my experience—very hands-off on that. Whereas if you’re bylining under your own name, or these projects reflect you and your personal brand, then yeah, you maybe want to consider not going agency model and having that Jesus saving the content, or Jesusing the project and making it the Kaleigh Moore or, you know, the Michael Keenan or whatever.
Kaleigh: That’s the thing. A lot of times I still really want to get in there and get into the weeds and write on a topic and build out sections and do stuff like that. So this type of operation gives me the ability to do that while still being super efficient.
As far as workflow goes, it’s nothing fancy. It’s really just kind of like, “How can I play to my strengths? How can I delegate the things that I either find really tedious or that I’m not super great at?” And I think that really enhances the outcome of the material as well.
It makes the content better, stronger, and more effective, because, yes, I’m using the things that I’m good at, but I’m also playing to other people’s strengths as well. At the same time, it’s kind of an apprenticeship model where the people that I work with are learning from me, and I’m learning from them. So it’s everybody wins in this equation.
Michael: Okay, very interesting. Thanks for sharing how your workflow works.
You say it’s like an apprenticeship model—which I love. I love learning because I always think there’s something to learn, no matter what stage or “advanced whatever”, you can always learn from the people around you.
So who are the people? Or how do you decide, “Hey, this person is going to complement my workflow or my project?” How do you know? Are you looking for juniors? What’s the profile that you’re going after?
+ “You still have to be very selective about the things that you say ‘yes’ to, and saying ‘no’, is a superpower.” —KM
Kaleigh: I don’t work with a ton of other freelancers. It’s a very small group of people. Most of them I’ve worked with for a long time, either I’ve helped them with projects, or they’ve helped me on past projects. So I know what their subject matter expertise is, and kind of what their strengths are as writers.
It’s not even a matter of keeping a spreadsheet, there are like three or four people that I work with regularly, and here’s what their bandwidth is, and here’s what they’re good at. So just delegating based on that. And again, a lot of the time, it’s still, “I really liked this topic, I want to get in there myself, I just kind of need a little bit of help to get this first draft rounded out, fleshed out, finished up things like that.”
Sometimes it’s not even a super heavy lift, but it’s really just a matter of knowing your people and knowing who’s good at what. It’s not super complex. I think it’s just a matter of just communication and keeping an open door. Knowing what people like too. Because you don’t want to give people projects or assignments that they’re like, “I don’t want to do this” because it shows [in their] work.
Michael: In this sense of building out your team and working [with] people, what’s the biggest mistake that you’ve ever made? And what have you learned from that mistake?
Kaleigh: I think my biggest mistake is…there was a point in my business where I was really, really busy all the time. I was getting a ton of projects, I was saying yes to everything because… money. Opportunity. Wonderful. It was too much.
So I was bringing in people who I hadn’t worked with a ton before and I wasn’t super happy with the quality of work, so I ended up having to do it over myself. Kind of a word of wisdom is, don’t get in over your head. Yes, there’s endless opportunity once you get to a certain point within your freelancing business where you’re getting a ton of opportunity, but you still have to be very selective about the things that you say yes to, and saying no, is a superpower.
I think that’s a big lesson to take from this for premium freelancers is that when you get this influx of work, and you get all these people who are like, “ooh, we’d love to work with you.”
Being highly selective, number one, is good, because it shows that you’re in demand when you can turn down projects or refer them out. And number two, economics 101, when demand increases, price increases.
The more in demand you are the higher you can charge because you can say, “If I lose this project, that’s fine. There’s somebody else who’s going to scoop up the slot.”
Michael: Oh, wow, I love that. I didn’t even think about that. Like “no” as a superpower. Because I usually just say, just say no to things that you don’t want to do.
Okay, so given the luxury of additional time, how would you approach building a workflow from scratch? If you’re just a freelancer outside of content, it doesn’t matter what the industry is, how would you approach it?
+ “That feels like premium freelancing to me. When you have the flexibility to be like, “I’m only going to set my work day to be this long. This is what my ideal day workwise looks like. And here’s how I’m going to build it and construct it so it looks that way, and how it functions that way.”—KM
Kaleigh: Looking back, I was like, “Oh, I have the bandwidth now to do so much more.” And I said, “Yes, yes, yes, let’s do it. Let’s do it.” So in hindsight, now, what I would do is build a workflow to where I’m working no more than like five and a half hours a day. Because what I found is that is my sweet spot. That is where I feel happiest [and where] I do the best quality of work. It’s [a] good work-life balance.
That feels like premium freelancing to me. When you have the flexibility to be like, “I’m only going to set my work day to be this long. This is what my ideal day workwise looks like. And here’s how I’m going to build it and construct it so it looks that way, and how it functions that way.”
So I would just be highly selective. I’d find like three or four really good, high-quality people that you trust, that deliver projects on time, that do what they say they’re going to do and pay them well.
And when they go above and beyond, reward them. Send them their favorite alcohol or send them a gift card to Amazon—do things that let them know you appreciate [them] because they’re what’s helping you build the business and get to that premium freelancer level. And you can’t do it without them. So you have to really be good to those people.
Michael: I agree. 100%. And I just want to say, I did help you with that brief once and I really love red wine in the fall so if you’re planning on sending me my favorite alcohol. I like red wine at this time of year. So I’m just going to put that out there.
Kaleigh: Okay. On it. What about you? I’m curious, what things have you done that you feel have really helped you level up your freelance business?
Michael: Teaching what I know, is actually one of the most rewarding things that I’ve done. Outside of the financials, teaching what I have learned has been the most rewarding thing for me. And I do that through Peak Freelance.
What I really love about it (and I’m going a little off-topic here), beyond the courses and everything, it’s the community that I’ve worked to build with the Elise in Peak Freelance that has been the most rewarding because I’ve learned so much from other freelancers about how to freelance. You know, all the different styles, the problems, and then just connecting with other friends (well they weren’t friends, but now they’re friends), and connecting with other people who have the same challenges and issues and kind of solving them together.
That’s the byproduct of how I wanted to take the skills that I’ve learned and share them with other people through Peak Freelance. I got all these other amazing benefits that I really am grateful for every single day. I get into Slack, into Peak Freelance and I get to chat up with my new friends there—we get to engage in the conversations.
It was going outside of just the traditional like, “hey, make an online course now that you know what you’re doing. Because the truth behind that is, they’re actually not that easy to sell. I know there [are] so many get-rich-quick schemes to sell your course and stuff. But they’re not that easy to make a lot of money off of.
They’re a good avenue. You can get trickle income—that’s not a word—I was thinking trickle down economics. But you can [get a] trickle in the income but—
Kaleigh: Selling is hard.
Michael: Yeah, selling is hard, really hard.
My newsletter has been another way.
+ “I just continued learning and really becoming a strategic asset in clients’ businesses, and not being just the assignment taker…That’s something that makes clients look at you as an advanced freelancer, not just you feeling like you’re advanced because you made money.”—MK
Then in terms of client work, I just continued learning and really becoming a strategic asset in clients’ businesses, and not being just the assignment taker. Creating [my] own assignments, pitching ideas, pitching projects, pitching opportunities to [my] clients. That’s something that’s outside of the workflow, outside of the money. That’s something that makes clients look at you as an advanced freelancer, not just you feeling like you’re advanced because you made money.
It’s those things that I think have had the biggest impact and that have given me the opportunity to charge more. Because we both win, right? They get an amazing project, they get whatever metrics that they want, whether it’s to increase customers, yada, yada, and you get more money and you get more experience.
Kaleigh: To kind of close things up here. The other thing to think about getting to that next level of freelancing is, what are the things adjacent to the service you’re offering now that maybe you could bundle together and package up? To number one, make your clients’ lives easier and number two, take things off their plate.
Because when you think about it, for freelance writers especially—you think about the content manager, they’re responsible for so many different things like; uploading content into the CMS, and doing the SEO audit, and a myriad of things like that. [So], are there services that you could package into your rate where they’re going to get more value out of working with you? It’s also going to simplify things on their end.
For example, if you were a content writer who was helping with the actual execution of the writing piece, you could say [to your client], “I also have someone who can help build a really strong SEO outline for this, and I can kind of work from that. So if SEO is a big goal for you, this is something that’s going to make your life easier, because I’ve got somebody who can handle this, I just need a little bit of direction from you.”
Another example of this would be, “So I have a friend who specializes in content strategy.” And I don’t work with anybody unless they have a content strategy. But I don’t want to do that. So I refer those people to her and she gives me a referral fee and then sends them back to me when it’s time for the content strategy to be executed.
It’s a win for both of us, and the client is getting more out of working with me [than] if they didn’t have the content strategy.
I never want somebody to spend money with me aimlessly, I want them to have a plan. So pointing them to somebody who can help them do that makes my work better, too. So again, everybody wins.
Michael: I’ll just tack on one last thing is, even outside of marketing and content, that is also applicable. I’ve worked in a design UX design firm and—I should mention he was kind of like us, he was a solo person. His business was structured like a firm, but he was the main person—he touched every project. He hired the resources, but his specialty was UX and that was the main sell. But he hired UI people to come in.
For example, maybe he would build the wireframes and someone would build the interface, and they can ship the whole project together. So a client doesn’t have to worry about building a UI, they can get it all in one place. Because again, like we’re saying, that’s a way to become an advanced freelancer.
What are the things that your clients don’t want to do after you submit your project to them? How can you offer that so it makes life easier for them? Because that’s all they want. They just want their lives to be easier.
Kaleigh: Yeah, maybe it’s coming up with a distribution plan or social media copy or having like a CRO audit. If you’re doing landing pages, having that built-in to your copywriting proposal— whatever it might be.
I feel like all of these are ways to charge more and earn more, but also kind of level up your business and the services you’re offering as well. So lots of options here.
We’ve given you a few to think about. I would say just think about what makes sense for you. Think about the things that you enjoy doing versus what you don’t enjoy doing and find a way to kind of make those puzzle pieces fit together. That’s it. That’s it.
Creative Class reopens for new students in Spring 2023: