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yb+ys season 2: episode 6

The ROI of FreelanceDesign

with Sarah Casterline

Freelance Designer

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Are you having trouble managing profitability as a freelancer? Freelance designer, Sarah Casterline, discusses how she has remained profitable as a design freelancer; we also talk about building a portfolio of “passion” freelance projects.

About Our Guest

Sarah is an award-winning graphic designer and marketer who has been making things pretty with a purpose for almost 8 years. She helps businesses grow through engaging brand style & identity. Due to her diverse marketing background, she understands the role of design in a greater strategy. She designed the pitch deck that secured $20M in Series B funding for HUNGRY. Learn more and see past work at

Season 2: Episode 6

podcast transcripts
0:53 Megan Ingram (MI): Sarah Casterline joins the podcast this week. She is an award-winning graphic designer and marketer who has been making things “pretty with a purpose” for almost eight years. She helps businesses grow through engaging brand style and identity. Due to her diverse marketing background, she understands the role of design in a greater strategy. Today, she discusses with us how she has remained profitable as a design freelancer. And we also talk about building a portfolio of passion freelance projects. How's it going Sarah? 

1:22 Sarah Casterline (SC): It's going well, I'm happy to be here. 

1:26 MI: Yeah. I'm great to have you on. Well, to kick things off, storytelling is a big thing through this podcast and I'd love to hear about your journey from full-time creative to now a freelance designer. Can you talk a little bit about your journey through all this? 

1:47 SC: Absolutely. And my journey in particular was not linear at all. I mean, like a few people are at this point. I actually started off not even as a full-time creative, and was more or less a self-made and self-taught designer. My first job out of college was at an ad agency and I was an assistant. It was a very administrative role, but I had access to all of these really creative people. And so I took everyone to lunch, all of the different roles, including the creative directors, but also the account manager, project managers. I was just fresh out of college, super eager to learn. And most of the time people are so willing to share what they've learned, they spend their whole lives amassing this skillset and this knowledge and all the lessons they learned. Most people jump at the opportunity to mentor someone in the right situation. And I always found that amazing to me, how many people didn't take advantage of that. So the more I learned about creatives, the more I was like, that's exactly where I want to be. But there was this idea that creativity is binary. You are either creative or you're not, and it's really hard to jump between the two. And I knew if I wanted to make that jump, I had to make it early. I was commuting into DC. It was like an hour and a half or more, each way. So I had to wake up really early, go into a coffee shop and get a client and make something in the early hours and in the nighttime hours. It was like cheap or free client work in the beginning. It was pulling any projects in school that were somewhat relevant. And then it was also doing spec work, coming up with projects that were similar to things that I really wished I could create to just make a body of work. Switch into that field, get any creative job that I could. And as soon as I did, we just took off from there. I just needed one person to give me a chance. And as soon as they did, I had to go along the path and find where I fit. It all kind of stemmed from that. And then once you get into the startup world, that's when your skills get to be utilized because startups are not one cog in the machine and you only do this one thing. They really can use all the help that they could get. So there is nothing like you're creative or you're not. You can do all kinds of different things. So I got to flex all the different muscles of all the things I was interested in relating to marketing. I got to learn a lot more about the strategy piece, the marketing piece, and I've been working for several years now to pull them all together to have a well-rounded strategic approach to design. The most fun is all of that coming together now. 

5:02 MI: Yeah, that's totally awesome. And I like that you touched on the startup environment, because that is a great opportunity to learn a lot about different things. Cause you get thrown into a lot of different roles and hats, so to speak.

5:19 MI (voiceover): Whether you're talking about different sizes of companies, different types of brands, different types of roles, whether you're a freelancer, solopreneur, or a full-time employee, there is so much value in education and having different types of roles, different types of projects, different types of working experiences. You learn so much about what you like, what you don't like, what are the things that you want to focus on? What not to focus on. Listen in.  

5:49 SC: Definitely 

5:50 MI: Talk a little bit about some of the lessons you learned as you were going through that journey to being a full-time freelancer.

5:59 SC: Yeah. I think the biggest thing for me is, you're the one who's living it day in and day out. So other people's opinions, take them with a grain of salt because you're living it. No one understands your vision, but you. No one understands your dream, but you. I think taking that time to self-reflect and really think about what's important to you because prosperity and balance and success are different for everyone. Deciding what you really want and what your dream is and going for it. I think having that clarity is something that is like the hardest step for people. Once you have that clarity, you are able to achieve it because you can go, okay, well, now that I have even a rough trajectory, it doesn't have to be a super concrete thing that never changes, your priorities shift as you get older, or could shift as you get older. But having that trajectory, you can clear away everything else that's a distraction from that and focus and move forward. And I think if you just do a little bit every day towards that, you really move the needle and you see that progress over time. But I think most people don't get past that. And they let everyone else decide for them. I think that's the hardest part about entrepreneurship. You see things differently than other people and you really have to believe in your vision, even if other people don't understand it. 

7:30 MI: Yeah. That's great. Great advice there. We talked a little bit about working in a startup environment. I know you've worked on a variety of brands of all sizes from large to start-up to medium size. Do you have a preference? And what do you enjoy about working on different types of brands and sizes?

7:50 SC: Yeah, that's a great question. I'll preface this by saying, you need both to have a well-rounded portfolio of work. The bigger companies can afford you, and they can compensate you well, and having a few of those balances you out financially so that you can give a little more help to some of those smaller companies. I think smaller companies are so special because you can really make such a huge impact for them. Make a couple of designs that transform their whole business, and that is so impactful and it's so fulfilling. And so I think those are definitely kinda my favorite to work on. I think you do need both to keep the lights on at the same time.

8:40 MI: And I agree with that. I've had experiences both working on the large side of things and small, and I agree I've learned different things from both and things that are really fun and cool about them. And on the opposite side, some challenges that are tough. So it's like a give and take with what you choose, but I do agree that having a well-rounded experience of working on different types of things teaches you a lot. 

9:05 SC: Definitely like some of the resources you get access to when you're working with a big company and you can learn and take that experience and then help some of the smaller companies. 

9:15 MI: For sure. Yeah. Agreed. What advice do you have for freelancers who are trying to decide between a niche and going after businesses more broadly? 

9:24 SC: My advice for that would be don't narrow yourself down too quickly, to scare off a bunch of work, but I definitely think you should be working toward a niche, based on what really lights you up when you're working on it and what your superpowers are. When you find that your strengths really lie here. I say, definitely start to niche down based on those things. But I wouldn't start out right off the gate if you're a brand new freelancer, I wouldn't say like, no, I only do tech web design for this specific type of company. I mean, if you have enough clients and you can just do that and you know, for sure, right off the bat, that that's exactly what you're good at and that's the only thing you want to do then. Great. But in general, for most people, it takes a little time to really find what those things are.

10:25 MI (voiceover): Freelance focus - to specialize or not? An Upwork study found that specialist freelancers had great success with 50% of freelancers providing skilled services, such as computer programming, marketing, IT, and business consulting, up from 45% in 2019. The decision about whether you should specialize or not really comes down to how much you love this one thing, if you really do, whether it's design, analytics, writing. If you really love that one thing you want to focus on it, maybe a specialized career path is for you, but in order to determine that you really need to figure out what is it that you like, what is it that you don't, what are the types of marketing projects and experiences that you want to have, maybe your best, more suited to a variety of different projects, to be more of a marketing Swiss army knife of sorts. Figure out what that is that you're passionate about and pursue a career path down that road.

11:22 SC: Again, it takes some time to get there. 

11:26 MI: I think that's good advice, especially when you're starting out. I like to think of it as looking for qualities you want in brands and people, as opposed to this very targeted industry or thing and getting people who align with the types of qualities that you're looking for in a more broad sense and starting from there.

11:48 SC: Yeah, that's so smart. 

11:51 MI: I know you have a personal passion for working on feminine brands. I wanted to have you talk a little bit more about that. But how do you navigate your personal passion for freelance projects versus trying to just make it as a freelancer?

12:10 SC: Yeah, that's the number one question, right? For me in particular, I am now at a point because I worked for eight years within the creative industry learning as much as I could before going off on my own. I think now I'm fortunate to be in a position where I have a network. I have a personal brand that I've been building for a long time. I have a reputation for my work and I have a body of work that you can see, and confidence in my skill set and in what I can bring to the table that you don't always have when you first start out. Like I said, when I first started out, you are doing maybe some discount things just to get your foot in the door. I don't think you have to do that forever. Fortunately, once you've been doing it for long enough, and you have developed your super powers and you kind of know what differentiates you and where you lie and who you're going to gel with and who you're not going to gel with. You're more in a position to be choosy about what projects you take on. And so that is the biggest joy where I am now is that I feel like I had my years where I was just learning and doing as much as I could. And now I'm in a position where I can raise my prices, make my time a little bit more valuable. Saying no is so empowering at this stage. I really do believe in what you said. Align yourself with customers that, you know, are going to value your work and respect your time and respect your expertise. I can spot red flags a mile away now and I can tell right off the bat, if a customer or a client is going to just be a nightmare. Like I said, I'm fortunate enough that I've been able to increase this and do more of this and kind of figure out okay what my balance is and how much I can increase my prices and still be in a good zone. Some of that comes with just experience that you're able to be a little bit more choosy and know yourself and know those values that you're going to connect with and things like that.

14:48 MI: Yeah. And I love that. I always say it's a process where it should be about both people involved. Where they’re looking at you and determining whether you're going to be the right freelancer for the project. It's also you evaluating whether they're the type of person that you want to work with. I always encourage freelancers. It's a two-way street. It's a project that you don't think is the right fit, for whatever reason maybe it's not the right project or the right client or things like that. You want to make sure that it fits for both parties involved so that it will be a successful project. 

15:29 MI (voiceover): Work with people who align with what you stand for. For Ingram Digital Consulting: It's to be curious, be creative, be bold, be socially conscious. When you're going through the client vetting process, be very careful. It's time for you to evaluate. Are they a good fit for you? Are you a good fit for them? It's a two-way street. So make sure that you're looking carefully and you're identifying whether these are truly the types of people that you want to work with. Because believe me, the red flags will show up later on. It won't be a long-term project. You won't get a referral out of it. And at the end of the day, you want to be building long term, positive, sustainable, relationships. Those are the types of people that you want to be invested in. Those are the types of people that you want to work together with as partners.

16:18 SC: Exactly. Yeah. And I think if you know that it's not going to be a good style fit or timeline fit, that the work will suffer and like you said, you want it to be a successful project. Emphasizing that is a great way to gracefully decline. Just because we're saying no doesn't mean we're being rude, but I think it is such a powerful thing to be able to say, I just don't think this is a great fit. Here are some people I recommend that you work with and just move on and then everybody's better off. Not just you, not just them, like everyone. 

16:58 MI: As someone who works a lot with freelancers, I've got some really great referrals that way where freelancers are like, Hey, this may not be right for me, but then I've gotten to meet some really cool, new people that way too. So it's still a good opportunity to build relationships and network, which is a huge part of being a freelancer.

17:16 SC: Yeah, definitely. 

17:20 MI: So what has worked for you to help you find these passion projects?

17:27 SC: It's a great question. I see a lot of small businesses on Instagram and on social media, really small, like brand new businesses. A lot of them might not be able to afford me. But, I try to reach out to some at different times when I have the ability to, and maybe do some discounted work here and there for different female owned small businesses, just because I love what they're doing, or I love the mission. I have been fortunate to find just through my network, people I've either known from college, or high school or, working. I think entrepreneurship seems like it's the way that people find balance in their lives. Sometimes when they can't find it in a corporate situation, entrepreneurship allows them to follow a passion, fill a need that they've seen, a gap in some market that they feel like they can fill. It's really cool. It seems like it's everywhere. I've been able to reach out to people who I've seen have a really good idea. One of my favorite clients right now. She was an Amazon developer for years and she just left completely to sell headbands on the internet. They're like adult headbands. They're beautiful. She found such a great gap in the market because most of the headbands that are competitive with what she's selling are way more expensive. Hers are good, they're great quality and all that. They are not cheap, but she's just found that sweet spot. And I told her right away, I said, “you have something here and I really want to help you.” I offered to help her pro bono a little bit in the beginning, and she saw the growth. She saw the results. Just in general from her own success in being able to grow, she was like, “I can afford to take you on, let's continue to work together.” You've helped me see that this business really could be something. Finding those people is being able to recognize when you look around within your own network and you see different people doing different things. It's just being able to recognize which opportunities are really going to mesh well with you. And I just knew from the beginning, I would do all of this for free because I love your brand. I love you. We clicked. We were both helping each other. It was just empowering on both levels. Everybody was just having a good time. And that translates into magic in the work, you know? 

20:31 MI: Yeah, that's well said. I completely agree. And those are the types I talk about building long-term relationships. When you work with people who you sync with in that way, it makes doing that and having more long term relationships, much easier and much more likely to happen. 

20:52 SC: Yeah. Yeah. In those scenarios it becomes a no-brainer. 

20:54 MI: Yeah, exactly. So I know for freelancers, often we talk about the business of the business. It's wearing the hat of now I got to manage this thing, now I got to actually manage a business. And so I did want to talk a little bit about the dreaded word of ROI and how you remain profitable as a design freelancer, day to day. 

21:20 SC: Yeah. Well, so one thing that I recommend doing, if you are full-time at a company and you're thinking about taking the plunge that I did, that was risk mitigation on my part. When you are set on leaving potentially it cannot hurt to negotiate with your current employer. I had built a great relationship with the startup that I was at and they were very innovative, forward thinking people and have a great relationship with them. So I said, hey, this is what I ultimately want to do. This is my dream. These are my goals, but I think this could be a win-win for both of us, because I can continue to give you these high value items that are the most important thing that you get from me day-to-day being a full-time employee at a lower cost. And then I can have a safety net going into my own thing. My boss at the time, his response was amazing. He was like, you're really good at what you do. And we're definitely going to support you. And I knew this day would come and he was like, all right, let's do this. But, you have to raise your prices. You have to make sure that you value yourself. I was like, okay, great. It sounds good. And so going into it, I had at least one steady recurring client and that alone can be a huge starting point for you. And also can allow you to be a little bit more choosy about who you take on. And so I wasn't desperate to add new clients to my plate and grab whoever I could. I could wait it out and get clients I was really passionate about. And back to what we were saying no or knowing your vision and being a little bit selective. I always try to remind myself that when you say yes to something you're saying no to something else. So sometimes when you feel bad about saying no, remember, you have to remain open for the opportunities that you really want. I don't think that will last forever working with your employer because it is a little bit of a gray area because you were an employee and now you're a freelancer and you definitely want to be careful not to be treated like an employee, but paid like a freelancer. So you do have to really advocate for yourself and that transition can be a little gray area, but it's a great starting point. In general, if you can't do that, I think like you said, building those relationships is really important and I've often found that if you just do one project for someone and then you do a great job, they come back to you and you end up with recurring work because the nature of today, there's so much design and marketing work to be done with everything being so visual and everything being online and businesses have so much that they need, because there's this expectation that brands are going to be cohesive and well-branded at every touch point in the customer journey. And that means everything from if you're e-commerce, the packaging that you get when you make an order, to the social media that you see, to the confirmation email. So there's a never ending list of things that a company is going to do. So if you can just do one project, well, there's a high chance that it ends up being a recurring project and you can just build up your list that way. 

25:09 MI: That's well said. Really good advice especially when you're starting out. What are some challenges that you've run into as you're balancing profitability and just all the various things that you have to do to manage a freelance business? 

25:26 SC: Yeah, that's a great question. The pro is that you can choose what you want to do, but the con is that every job you turn down is money. So it really feels like you are constantly balancing your work-life balance or your financial goals. So you're constantly weighing those two things and I'm guilty of this. A lot of entrepreneurs and freelancers are, too. It's very easy to overwork yourself. Very easy. I talk about saying no, but it's also really hard to do, especially if you want to do everything, you know? I think it's important to remember what your goals are, what success means to you. Sometimes it might mean, I want to take a season of a little bit less work and that might mean a little bit less money for the season, but my mental health is going to benefit from that. Or this might be a season where I'm just really going to power through and do a ton and do all of the things. And maybe be a little uncomfortable, but my business is going to move forward because of that. So you're always evaluating these pros and cons. And the ultimate goal everyone should be working towards is getting to a point where you're confident in your skills, you have a network, you have a differentiator, and you feel like you can raise your prices and then bring in some other types of income like you get speaking gigs based on a certain topic that you know, something about you can teach a group of professionals how to do something or teach a course or, get some sort of profit multiplier so that you can do two of those a year and drastically reduce the amount of clients you have to take on to reach this revenue goal. Like I think there are ways to be smart about it and that's what I'm working on right now is determining my ideal pricing so that I can do a little less work and still meet my financial goals. And then finding other creative ways to do things other than just your hourly core product, which again, limits you because then you're only able to make money the hours you are working.

27:50 MI: Yeah. And I'm glad you mentioned the pricing part because that's a key part too, and not overworking yourself to death because if you're taking lower rates, that means you're not coming in at the place you want to be. So make sure when you're having those negotiations and conversations that you're coming in at the right number for you, so that you can have that freedom and that flexibility to do the projects that you want to work on and not feel like you're just working crazy amounts of hours every day and stressing yourself out over it. 

28:22 SC: Absolutely. And it's so easy to do. You really have to just value yourself and say, no, this work is worth it. I have to, these are the rates. Someone gave me great advice. They were like, say, “these are the rates." Don't say you know, “these are my rates." These are the rates. They're non-negotiable if they don't fit your budget, that's unfortunate, but don't lower your rates for people because that doesn't work out in the end. 

28:49 MI (voiceover): Pricing can be one of the toughest things as a freelancer, especially when you're first starting out. Some pricing lessons of mine, as you figure out what is the right price you should come in at. Where should you price out? What types of different offers should you have? One, define your monetary goals. Well, we can offer so many marketing services under the sun. We need to define and tailor services that consider the service value, the time constraints, the marketing tools, the education needed and the scope. Make sure you're thinking about all those things when you're setting your goals. And then secondly, and probably even more importantly, have confidence when you're presenting that to a client, don't be intimidated when proposing a price. Don't let someone come in and make you unsure of the price that you set. Set that goal, know that goal, and come in with that confidence and believe me, that will come through in a conversation and you'll get your clients to agree, convert and win the business. 

30:01 MI: Totally, totally agree. Well, last question, obviously we're big on trends. I love marketing trends. What's one design trend, or maybe a few that you foresee right now, as you're looking through looking at the back half of this year? 

30:18 SC: Yeah, that's a great question. Some of the ones that have already been in play that I've seen are definitely Serif types. Like custom Serif type for logos and things like that. The design world is blowing up about those. I think that's something that people are really into and you get something that's really unique to your business. Then colors wise. It's either all neutrals beige and black and white, or you're going with these sickeningly sweet, bright pastels. Those two kinds of odds, one or the other, those are the design trends that I'm currently seeing. And then I think futurewise, we've already started to see a lot of movement as another design element, which never used to exist when everything was print. And even in the beginning of everything being digital now, anytime they make anything, the question is, can I make it a GIF? Can I add movement to it? And it can be done in a very simple way. And often should be in a very simple way, if you can add movement, people really love that. And that's so cool that you have this 3-D way of designing. You're not just working with this 2-D like okay. Colors and fonts. You've got movement, where are you drawing the eye? So I think people are really gonna have the attention span of like toddlers, but we love when things move.

31:58 MI: So true. And I like the comments about the gif, the animation, the movement. Part of it is definitely something I've seen myself that a lot of people are going towards, especially with digital and social kind of moving in the direction they've been moving over the last year. 

32:14 SC: Definitely I've seen it a lot, particularly in email marketing. I really think designers like brand new designers should really try their hand at email marketing. I don't know if this is being pushed in design schools at all. I don't think it is, but I think if you can get really good at that, it is such a coveted skill because it really benefits companies. It's a really powerful marketing tool. And I see some companies that do it really well. They have beautiful email marketing, but I would say the majority of companies have a ton of room for them to improve their email marketing in terms of design. They're using very classic grid layouts with a ton of text. And there’s a ton of opportunities on that platform to do really cool things. Like I said, movement, cool visuals and make really striking art that converts. I think that's the thing that every designer should be just trying their hand at. 

33:26 MI: Yeah. That's a great call out. I like that. Well, thank you so much for joining the podcast today. Where can people find you? 

33:35 SC: They can find me on Instagram. I post a lot of my work there. My handle is @sarahcasterlinedesign, and then also on TikTok that is the same handle, sarahcasterlinedesign. And they can see my full body of work on my website,

33:54 MI: Amazing. We'll definitely go check her out. And again, it was a pleasure having you on the podcast today and I definitely wish you the best of luck. 

34:03 SC: Thank you. Thanks so much for having me. This was fun. 
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