Leveling Up in Your Freelance Business

SEASON 4, EPISODE 3:

As the holiday season approaches, you might be anticipating a bit of a lull in your freelance business. Perhaps you're planning to take time off, or perhaps you're excited to work on your own stuff while your inbox quiets down. Whatever your approach, we're using the next few episodes of season 4 to talk about ways to shift and grow your business in 2022. Today's episode is about leveling up, taking your business to the next level, and refining strategies that may no longer work for you. First, we want to say that leveling up is not a requirement. Capitalism may make it seem like a requirement, but sometimes what serves you best is staying the course and maintaining your current pace. So if that’s where you’re at, tuck this episode away for a moment when you’re craving growth. But if you’re itching for more, this episode will hopefully inspire you to challenge yourself. We'll dig into level-up strategies like growing new skills, making more money, changing the pace of your business, hiring help, and so much more. If you haven't already, check out our season 3 episode on inflection points, which is a great accompaniment to this episode. How have you leveled up in your business so far? Where could you level up in 2022?

Full Transcript Below:

Wudan- Hello, everyone and welcome to The Writers' Co-op.

Jenni- We are a business podcast for freelance creatives everywhere.

W- I'm your co-host, Wudan Yan.

J- And I'm Jenni Gritters. 

W- Hey, Jenni. 

J- Hey, Wudan, how's it going?

W- Oh, my God. It's going. I don't know about you, but fall is a busy time of year. Summer's busy for me because I'm busy not working. And fall always feels like the final sprint before I take my winter break. I basically log off mid-December. So there's been lots of travel for work, getting in adventures with good weather windows, all the things. What about you, Jenni?

J- Yeah, same. I'm so busy. I opened up the coaching floodgates, which you know, has been awesome. But it's also just very new. So I'm setting a workflow that helps me onboard people really fast. They can self-schedule into my calendar. All good things, but it just like means that my schedule is super busy. But I'm mentally in a good place. And I also can't say yes to any more writing work this fall. So I guess that's a good thing. "No" muscle flex there.

W- Love the no. Love the no muscle. So that is a great lead-in why don't we dive into our episode today, which we are talking about leveling up in our freelance business.

J- Yeah, we get questions about this all the time, which is why we decided to record this episode.

W- Yeah, everything from how to level up? Or what are the ways to level up? Or I've been doing this for forever; does it get better than this?

J- Yeah, Wudan. When you look back and reflect on your business over the last however many years, how would you describe some of the ways that you've leveled up?

W- So it's been over eight years for me running a freelance business now. I think the major ways I've leveled up are a few things. So one, very early on, I took a gamble and a pay cut to learn how to write features. I learned how to get grants to support my long term reporting projects. And then more recently, in terms of leveling up, I made a bunch of adjustments so I could pull in a higher annual income. What do you think, Jenni? How have you leveled up?

J- Yeah, in a lot of ways I leveled up when I hired an assistant. And I think working on this podcast has actually pushed me in a lot of ways, in terms of how I talk about my business to other people. And then there's like all the little big things, right, like we just said, the no's. saying, no to assignments that don't serve me. And little things beyond that, just small behaviors. Hilariously, I think my biggest level up is not about making more money. It's actually about making less money, and working less over the course of 2021. And learning how to step back from the hustle. For me, that's one of the hardest, but most important things I've done to help my business become more sustainable. So Wudan, here's a question. When do we see people asking us about leveling up?

W- You know, I think the desire to level up often comes up when folks have hit an inflection point. We have an episode about that in our last season, when people you know, generally come to us for coaching. And we will link it to that past episode in our show notes.

J- Yeah, so a lot of my coaching clients come in, I think, at like two points asking about leveling up. The first is when they've been in the freelance world for a few years. And they're like, I survived. Now what? Right? It's that craving of a more sustainable long term path. And then to there are people who've been in this for like 10, 15, 20 years, and they want to push themselves again, like they need to second mountain. They already climbed the first one. So to me, I think leveling up in both of those cases is actually about refining what you're doing and taking on a new challenge.

W- Yeah, absolutely. I'd also define leveling up as what you just said, right? Like having the desire to take on a new challenge in your business that helps you grow your next step forward.

J- Mm hmm. Exactly. It's like your new growth edge. So what's interesting to me is that everyone's level up is different. Like, for example, for me, it's doing less, making less money, because of my personal struggles with overwork. But for some people, it's like making more, or bringing in new clients or pursuing an ambitious project. And I would also just say that you don't have to level up. You don't even have to have the desire to level up. Or maybe you're wanting to level up in different parts of your life. Like, there are seasons when it's just not nice for you to hustle, where you don't want to hustle. And I think there's a societal component that pushes us to feel like we must always be pushing, right? So I just want to throw out there before we dive into this, that this may not be your time to level up. You can chill. That's okay.

W- Yeah. And it's okay to have times where you want to level up, but you're not in a place to level up. So you're just brainstorming ways to level up. That's totally legit, too. I mean, I've had a lot of times where I want to level up at work and times when I don't, and I challenged myself in other ways. Many, many other ways.

J- Yeah. It's all seasons, right? So know that if you're listening today, and you're just like, nope, I do not want to push myself, that's real and fine. And you can save this episode for later, when you get to a time where you do feel like you want to push yourself a little bit.

W- So generally, I think leveling up is a great puzzle as a coach. And I think there's usually a lot of motivation that can come from clearly defining where you want to be in a year or two or maybe less if you have shorter term goals.

J- Yeah, agreed. I think it's a very empowering place to be to have decided that you want to take something on.

W- So today in this episode, we'll go through a few ways to level up your business. And keep in mind that you can steal as you want. And you might also pick something else entirely. But these are just some common ways we've seen people step up, step out and take risks as they grow their freelance careers.

J- Yep, let's do it. So Wudan, start us off, what is a first way that someone might consider leveling up?

W- So I think a big one for many freelancers is to value time and peace of mind enough that you start trading smaller projects for bigger ones. Jenni, does this resonate? Have you done anything like this?

J- Yeah, absolutely. So I've talked about my months where I had like 20 or 30 writing assignments due. True hell. Do not recommend. Each one paid like $200/$300. I was fried before I even got to week two of the month, like writing multiple assignments per day. To be clear, this can work for some people, I think, but for a lot of us the pace of that is just like a hard no.

W- Yeah, I agree. It's like you hit a wall, kind of, where you realize that this hustle worked for a bit. But now I have all kinds of clients and assignments, and I can show that off, right? And a lot of us do this in the beginning: the hustle. But to get more sustainable, we often need to rein it in.

J- Yeah, exactly. So one of the flexes here is that you can look for fewer assignments per month that are higher paid. You start to trade them out. So a month with eight to ten assignments instead of twenty. You hit your same financial goals. But to do that, you need those eight to tend to be pretty well paid.

W- How do you think about putting that into action?

J- That's a good question. So if I'm doing lots of one off assignments for a particular client, I will sometimes try to see if they can package them. So if there's either the potential to do multiple assignments at once, or to make this more of a long term commitment, right? So instead of one offs, can they bundle four blogs together, and then I'm hitting the $1,000 mark per month for just this one client, right? So we call this rotating or recurring stability.

W- Yeah, making things recurring, feel like less work, right? And also less hustle.

J- Yeah, exactly. So I guess the other way to think about this is to selectively pick up larger projects. So want to talk about that, Wudan?

W- Right. So larger projects in either scope or paycheck. I think you need to know what rateyou're aiming for. So I do this a lot. For instance, I don't take on projects that pay less than $1,000 a pop, it's not worth it to me anymore. And I think if you freelance as a journalist, you can make a deliberate decision to take on longer stories, rather than one off trend or news pieces. The analogy I would give is trading news for features. So news can be what got you to where you are today. But features are the things that may be a better pace for you in the long term.

J- Exactly. So one thing I'll say is that it is actually fairly common to take a pay cut when you're making this transition from smaller projects to larger ones. So it's a really brave move.

W- Absolutely. And it also takes a second for the cash flow to catch up with the new work that you're pulling in. And so when you do this, it's basically a reset button to make sure that the clients and projects you're working on align with your goals, you may end up with a month of barely any work to get more work new clients, and the checks will come in time. So as with all level ups, it's brave. And it requires trust that the thing you want exists.

J- Yeah, remember that you can also do this slowly. So one thing I encourage people to do is like, pull in one large project and offload two smaller ones. It's like a slower transition, and it can feel a little less groundless.

W- I like that. So the idea is to not let go of your security blanket all at once prioritize the things that you're most excited to trade out for what you want instead.

J- Yeah, exactly. So let's move on to level up number two. I think this one I would say is about raising your rates, right? Like your hourly rates or your project rates. So Wudan, you're a pro at this. How do you think about raising your rates?

W- So I think about two things. One is industries or type of clients who will have the budget to raise their rates. These are usually commercial clients who have higher profits, which we talked a bit in the values episode, it's a lot more likely that I can go to them with the rate that I want and that they'll be able to meet it. And then as far as journalism clients go, I tend to ignore all the publishers who won't be able to pay my rates. Just hard stop. No. I know that sounds really bold. It's been a long time since I wrote for less than $1 a word and slowly but surely I keep inching that boundary upwards. I think a lot about an interview. I heard with Taffy Akner who writes profiles for the New York Times Magazine, and that when she freelanced, she said she wouldn't get out of bed for less than $4 a word. So goals. Jenni, what do you have to add to this?

J- Yeah, I remember when she talked about that, and the Internet lit on fire. But I think the real tricky thing about high paying clients is that a) like you're saying, we do have to set the boundary that we're not gonna work for less than what we're asking for, right? But there is no "look here, do this" formula for finding these high paying clients. People are always asking us for like, give us the trick list, and I don't think there is one. But I think a lot of this is about empowering yourself to think about niches or industries that have some connection to your interest in expertise, right. And so something outside of your usual frame of who you would work for, consider those people consider what it would look like to dip your toes into that work?

W- For sure. It requires some out of the box thinking to identify those clients.

J- Agreed. And just to say it, like, I usually ask when we're having this conversation about upping rates: Why? Like, why do you want to make more? And that's because I want to know, what's in it for you, right? Like, what does it help you achieve? How does it help you feel like money is not usually about the actual dollar amounts. It's about the feelings and the things you associate with it. So when you're super closely tied to the feeling, and the things you get from a hard goal, you are actually more motivated to run at it. So if you're trying to up your rates, consider why does it matter to you? So I guess to summarize this, making more money usually looks like figuring out a how much more so you know what your new boundary is. And why? What's the reason behind it? And then considering out of the box solutions for new clients and setting standards for yourself, and then holding to them—being accountable to yourself. So I just want to say if you have blocks coming up around this, like if all of a sudden you're feeling kind of panicky and like oh my god, I probably should do that, and I don't know: I see you, I get it. And I think that actually brings us to the next level up.

W- Mindset! 

J- Yeah, mindset. So when you do something scary, your Gremlins are going to come out full force. You want to ask for $2 a word, your brain lights on fire. It screams, right? Like everybody else is better writer than me. And they aren't asking for more, or this industry doesn't pay well (that's a limiting belief. Go back to our last episode), I need more skills if I'm gonna ask for numbers like this. If I ask for more, and they say no, the client's gonna hate me. I'm never gonna have work again. I need confidence. I feel like crap, this industry sucks. I can't be a freelancer anymore. crawl into your bed, watch Netflix all day, right? Like, this is real. This happens to us. It goes on and on and on and on.

W- Yeah. And we want to say, this makes sense. It's not wrong for you to have these thoughts flying in front of your face.

J- Yeah. And I think I've actually learned that these freaked out thoughts actually mean I'm doing something I really want. Like, the more I want the thing, the greater the screaming brain.

W- Yeah, I don't know where I first heard this, but it's everywhere in the self growth books, right? It's like, you have to be scared in order to grow, you're gonna let go of something secure. It's also a sign that you're moving in the right direction. So of course, the big question is, how do you get rid of this self talk?

J- Yeah, it's a great question. So we talked about this a little bit in our last episode on limiting beliefs, which we'll link to in the show notes. But the big work is really to question these thoughts. Thoughts turns to feelings turns to actions. So if you start to question those thoughts, and wonder where they're coming from, you start to get more power. So for example, you experienced fear. That's a feeling, it leads to a thought: I'm not good enough. Then it leads to an action: you don't ask. So the work here is really to  interrupt that process. And then like, if it's not working for you, you get to pick something that might work for you. But asking those questions is step one.

W- This mindset work isn't always easy, but it's usually necessary for any kind of level up. If you want to move forward briefly, you're gonna have to, I don't know, slay the dragons. replace those thoughts?

J- Yeah, exactly. Someone told me the other day my Gremlin isn't on my shoulder anymore. It's around the corner. It lives down the street. So I know it's there. But at least that critical self talk is a little further away, just because they've been doing so much work to like understand it. And I like that analogy. So Wudan, I'm curious, what do you think are some ways to challenge mindset and tackle some of those thoughts and feelings when they don't work for us? 

W- Anything involving conversation. So therapy is great if you think it's something related to your mental health or your upbringing. Coaching, if you need a space to talk with somebody who's not in the box with you and want accountability to help you level up. OIr you can talk with friends, people in your writing group, just not in your own brain. You want somebody else to push back and challenge you.

J- Yep, absolutely. And then I think in addition to that, you can also sort of self coach yourself through journaling, or talking out loud as you run or hike. Wudan knows I record voice memos when I'm hiking sometimes. So again, our last episode on limiting beliefs would be a really good place to start with questions to ask yourself when you're getting hung up on some of these thoughts as you're trying to do something brave.

W- All right, on to the next level up. What others come up for you, Jenni?

J- Yeah, let's talk about negotiation, I think, and making a practice of holding to your boundaries.

W- Oh my god, you know, I love this.

J- Yes. Again, pro Wudan move: negotiation. So what does it look like for you to make a practice of negotiation, Wudan?

W- Negotiating for me is not just setting my boundaries, but also communicating my boundaries. That is kind of at a high level what negotiating is, to me, it's not just the back and forth about a fee or a contract. So I put up probably too many boundaries in my life, for better or worse, and I guess people still like to be my friends. So that's saying something. Businesswise, I love negotiating, I negotiate almost everything. Like I said, there are guardrails on everything. My boundaries change a lot based on my availability. And I want to remind people that like, small things are negotiable. You don't have to go negotiate the big thing right off the bat. You can start with something small. So not just contractual terms, that might seem scary, but maybe things like your deadline, or the amount of time you have to return an edit on something. I'm not so much negotiating my rate these days, which is a huge privilege. So either I'm writing for places that pay me what I want, or I'm naming my rates with client work. And I also really like to negotiate for clients to cover things like a transcription, I see negotiating as a conversation, and the person you're negotiating with is human. And I think that takes the scary part away for me. What about you, Jenni?

J- Yeah, I think it's interesting what you said about how you have a lot of boundaries in your life, and people still want to be your friend, because I've been working on this idea for myself of like, boundaries actually make it more comfortable for people to be close to us, because they know what to expect. They know what we need. And I think that translates too, to the way I run my business. One of my coaching clients called me a fierce protector of boundaries the other day, and I was like, Ooh, that's great. You said before, you don't take assignments under $1,000. That's my limit too unless it's like a steady client. And sometimes there are other reasons why I might take less for an assignment. So I don't always negotiate the rates. But like you said, I think there's a lot of other ways to negotiate. But really, for me, it comes back to knowing my boundaries. Like I actually have a document now called my business rulebook where I write down some of these boundaries, and holding to them, not just setting the boundary, but patrolling it as a matter of practice, and asking for what I need every time I have a new client. 

W- What is it that you'd like to say? J- Yeah, so for example, if I'm offered like $1200, and that's below my usual hourly rate, I would just say, hi, X, I usually charge $1500, for a project like this. Is that in your budget? It's direct, there's nothing else.

W- Keep it short. I love it. And we say practice becaus,e if negotiating becomes habitual, it also becomes less emotional. It's just something you do. It's a muscle that you use every single day, like your lungs to help you breathe, and then you don't even notice it. It's part of your business rulebook.

J- Yeah. And just to say, I think there's also something here in that negotiating is not just for yourself, it also helps other freelancers. The more we all hold to our boundaries in an industry that is, let's be honest, fairly notorious for trying to push things that may not feel comfortable for everybody, the more our clients will see what they need to offer freelancers. And the better rates or offerings will be for everybody else, because let's be honest, like market rates we determine the market rates, right? We're the ones doing the work. So there's a lot of good rising tides energy with this one, too.

W- Yeah. And I remember during our negotiation webinar way back when we talked about, you know, just trying to ask for $50 more every time and leveling up that way.

J- Yep, slow steps up the ladder. It doesn't have to be a lot, like you said, but the consistent growth will land you in a totally new place. So Wudan, let's talk about this. What if the client says no to your negotiation?

W- At this point, I frankly don't care. But you know, for a sane person, if a client says no, then it's worth having a conversation with yourself if it's worth it to you anyway. For me, it's not. I move on. There's other stuff on the pipeline.

J- Yeah, I think this level up at its root is also about not needing to be the right freelancer for every client. Like you don't need everyone to like you to be a successful business owner, which is something that has taken me a while to learn and is very, very empowering.

W- People have asked me if I've burned bridges with publications when I push back. And the answer is yes. But you know, I'm okay with that. Because I don't want to work with clients who can't meet my rates, or adhere to my boundaries that I want to hold down. There will be other clients who can treat me how I want to be treated.

J- Yeah, exactly. And you're okay with people not being 100% happy with you. And I think that's another huge mindset thing. It's really powerful stance because you are always willing to walk away which gives you the power in this situation. So let's do like, I don't know, like three more of these level ups. So Wudanm give me another one. 

W- Skill building. 

J- Oh, yeah. Good one. Okay, so investing in learning, right? Like, of course, we build skills as we do more and more of the same kind of work. But one big way to stretch yourself in your business and level up is to ask the question, what would it look like for me to become an expert in this area? And again, remember, like, not everyone wants to do this. But if you're feeling like you want trust and respect from your clients and your audience, one way to do that is to become a trusted resource on a certain topic, or maybe like on a certain skill.

W- Yeah, I think this is interesting for some freelancers, because a lot of us end up being generalists, and then wonder if we should have picked a niche.

J- I feel like this issue applies to you very much, Wudan. What do you think about it?

W- I started in a niche, and then I really broadened out. So I think picking a niche topic to specialize in is one way to market yourself and become an expert. But you can also become an expert in the craft of something you do, like the process. So it's more about the way that you do the thing than the topic that you want to focus on.

J- I agree with you. I think there are a lot of ways to become an expert, it doesn't necessarily have to be in a niche. So here's a question, how do we build expertise? What does that look like?

W- I think one way to do it is just to do it for a long time work with a lot of different clients within the same industry. Just doing the thing over and over will give you a knowledge base, basically. But you can also invest in skill building through courses, mentorship, or research.

J- Yeah, I was thinking of those options too. This is actually one of my current level ups, because I'm in a training for a coach and I was already a coach. Y'all know this. I've been doing it for two years. But I wanted to be a better coach. And I specifically was interested in improving my skills around mindset work and uncovering the causes of the issues we all face. So anyway, the level up required, honestly, me letting go of my ego a little bit to become a student again. But then also, it's really validating to see myself improve as I work with clients, which improves word of mouth. I don't have to do any marketing. There's a really good trickle down effect. So again, like I chose a year long certification, but you can invest in online courses, workshops, short things. You could even design your own course by pulling together your own curriculum and reading different things. So there are many ways this can look. Have you invested in any skills level ups recently, Wudan?

W- Honestly, it's been a second. So I signed up for business coaching earlier this year. And my coach basically showed me how I can streamline a lot of my processes. I went to her wanting to know how to one earn more money with the skills and services I want to offer and to stop feeling like I'm doing admin all the time, basically. So that's been helpful. And then other workshops I'm eyeing one of them is a narrative writing workshop for next year.

J- I love it. It's craft and business. So by the way, gaining new skills and certifications also gives you a really good excuse to raise your rates. So if you've been at the same rate for a while, ask yourself: why am I still at this rate? It might be a mindset thing. But if the answer is, in order to charge more, I feel like I need more expertise, well, there you go. That's your answer. That's your level up right now. You want to gain some new skills? 

W- All right, one more, I think we should go with maybe changing the structure of your business.

J- Yeah, I'm into it, I think of this one as kind of like a broad topic bucket. But it's like the idea that if you've been functioning by yourself in your business as a single member, LLC, or sole proprietor, like just working by yourself, basically, for a long time, you might sort of hit a top end of time and money. You only can make so much because you only have so much time and then you consider other shapes and sizes for your business.

W- This happened to me. There are so many hours in the day, and I can obviously only get so much done as one person.

J- I love it. Yeah. So there are different ways to look at this. One level up is to hire employees, or just think of yourself as an agency. So if you're doing more content work, for example, you can bring in subcontractors, if you're producing journalism, which I know many of you are who are listening, maybe you do need to be the one who's authoring the work. But you can bring on an assistant to help with admin, Wudan and I both done that. So there are a bunch of different ways this could look.

W- Yeah, we will link to our resources in hiring an assistant here, but it can be a big move. We've both done it. We have talked about it online and on the podcast, for sure.

J- Absolutely. So Wudan, tell me quickly, what are some benefits that you've seen from hiring someone to help you with your work?

W- I mean, number one, I've learned how to be a hiring manager, which is hilarious. But once I have picked somebody and they are in my system, I have less administration, I delegate very specific tasks, which means I can just focus on during the work. I think it also makes me look a lot more legit to other clients because sometimes I have an individual who acts like a filter on behalf of me.

J- Yes, less emotional labor. It's a good thing. So the other option here, like I said, is to start thinking of yourself as an agency, which some of my clients are in the midst of doing as well and which I actually considered at the start of my business. A lot of times, say you're working with clients and you find yourself with too many work offers for content development and not enough time, and your rates are already like pretty high for what you're doing, the question is, can you hire employees and subcontractors and pay them basically a chunk of your hourly or project rate?

W- We are asking how you can start to move into strategy, right? Like making decisions, working with clients to set up agreements, managing other people's work, while you hire people under you to do more basic tasks. So you're freeing yourself up to do more higher level work.

J- Yeah, and this is a level up because again, it's a risk, right? You're letting go of some measure of control, and you're letting someone else into your business, which we know can be tricky. And again, also can help you move in a more agile way as a business owner.

W- How many times, Jenni, do you think we can mention mindset work in this episode? But really, if you want to release control, because it ultimately benefits your business, you'll probably have to wrestle with a lot of that self talk

J- Yep, absolutely. I think it can help with this one to ask: what are you going to gain from hiring someone else? Like, what do you lose if you don't hire someone else is the question: revenue, peace of mind, all of that. But what do you gain? And then also just asking yourself, why are you afraid? What is your worst case scenario? And could you survive it? So a lot of times, our brain goes way out into left field, and the worst case scenario is not likely to happen. I actually have a few past coaching clients who have started to subcontract and they think of themselves now as agencies. And it's really cool to watch because they work a lot less at this point. But they're basically making the same amount or more, doing more delegation and management. It's cool.

W- It is cool. It's a big level up. It's a big next step. I'm into it. It's not for me, but that's something I've thought about a lot.

J- Yep, me too. I think it's a another cool flex, right?

W- Yeah. So to review, leveling up is about taking a risky move that allows you to grow in your business.

J- Yep. So I will quickly go through this list if I can remember them all. So some ways to level up include changing your business structure by hiring help, advancing your skills so you build up expertise, maybe making more money by raising your rates, changing the pace of your business by taking on fewer but more highly paid assignments, working on your mindset, making a practice of standing your ground with boundaries through negotiation. And yeah, I think that's it, trying to help yourself feel a little more in control and empowered when you take risks.

W- And there are so many other ways to level up like taking more vacation, reducing your work hours, adding new services, the list goes on and on.

J- Yes, it does. So we would love to hear from you. I know we always say that but specifically for this episode, we would love to hear about how you've leveled up. So if you want to send us a message on Twitter or email us, we'll drop those links into the show notes so that you can do that easily.

W- And if you haven't already, we'd love it if you could help rate and review The Writers' Co-op, especially on iTunes. It helps others find us.

J- Yes it does. Alright, so we are headed out but we hope you are having a successful fall, wherever you are. And however that looks for you.

W- Alright, talk to you next time, Jenni. 

J- Bye, Wudan. 

W- Season Four of The Writers' Co-op is made possible by you, our listeners. The Writers' Co-op is co-hosted and written by mem Wudan Yan and Jenni Gritters. Our producer is Jen Monnier. And our editor is Susan Valot.