Why Freelancers Should Adopt a Leadership Mindset with Cynthia Pong

SEASON 8, EPISODE 3

What if we told you that all freelancers are leaders? 

The idea might seem counterintuitive at first: After all, freelancers provide services or products to our clients. We’re not leading or managing a team in a conventional sense.

But leadership isn’t just about managing a team. It’s how you position yourself, how you talk about yourself, and how you show up every day in your work. 

In this episode, Wudan talks with Cynthia Pong. 

Cynthia is an award-winning career and leadership coach, speaker, and author of “Don't Stay in Your Lane: The Career Change Guide for Women of Color.” An NYU-trained lawyer turned career coach, she founded her company, Embrace Change, to help women of color—and people of color—secure the money, power, and respect they deserve.

Wudan and Cynthia dive into how to adopt a leadership mindset—even as a team of one.

Full Transcript Below:

Wudan Yan- Hi, everyone! Welcome back to the Writers' Co-op. This is Wudan Yan. I am your host and executive producer. What if I told you that all freelancers are leaders? Think about it. At first blush, that might feel counterintuitive, doesn't it? Like, we provide services or products to our clients or target audience. We're not leading or managing a team in that very conventional sense. On the other hand, though, it makes sense. Freelancing as a business of one is still a business. Sometimes when I fill out paperwork that asks for my company and title, I get a little kick when I say I'm the CEO of my business. And so if you run your business, you naturally lead. Coming to the idea that we are all leaders may feel abstract and challenging to wrap our minds around. But I can say for sure that this kind of mindset has paid dividends. So maybe you want to become the go-to commercial portrait photographer in the city that you live in. Maybe you want to be THE marketing firm that beauty companies hire. I'm just spitballing ideas. You want to be a keynote speaker when it comes to diversity in a particular industry. I mean, all of this...wants all of these desires help us establish our place in the competitive freelance marketplace to stand out from the noise. This mindset doesn't just serve us if, say, we want to scale to an agency or grow our businesses in another way. It serves us even if we are a company of one. So this, Cynthia Pong calls, is a leadership mindset. And I have her on the show today to tell us why having a leadership mindset matters so much, even as a business of one. Especially as a business of one. Cynthia is an award-winning career and leadership coach, speaker and author of Don't Stay in Your Lane: The Career Change Guide for Women of Color. An NYU-trained lawyer-turned-career coach, she founded her company Embrace Change, to help women of color and people of color secure the money, power and respect they deserve. In 2023, the flagship leadership training program she created and launched, the Leadership Accelerator, won an Anthem Award. Cynthia has been featured in The Atlantic, NBC, CBS and NPR. Fun fact, she has shared a virtual stage with Magic Johnson and is a LinkedIn top voice for job search and career. So if you're listening and you want to do big things in your freelance business this year or just crave ongoing support from a welcoming safe space, come join the Writers' Co-op Slack community, hundreds of members are sharing best practices and tips when it comes to running their freelance business. I can't overstate how important it is to have a psychologically safe community to help bounce ideas around almost every single day. Sign up today at the All Access level on Patreon to get a link to join that's at patreon.com/TWCpod. Okay, here is my conversation with Cynthia. Hi, Cynthia, welcome to the Writers' Co-op. It's so great to have you to have you back.

Cynthia Pong- Thank you. I always enjoy these conversations, so I'm delighted to be back. Thanks for having me.

Wudan- Well, to start, why don't you tell our listeners who you are, just to recap.

Cynthia- I'm Cynthia Pong. I founded and now I'm the CEO of Embrace Change, which is a career coaching and training firm. We specialize in working with women of color in a number of different areas. Business and entrepreneurship being one of them, leadership being another. And what else? I am a big introvert. I'm a middle child. I love Rottweilers. I'll leave it there for now.

Wudan- That's amazing. So Cynthia, you actually pitched me this idea of something that—

Cynthia-Sure did!

Wudan- Yeah! That I need to cover on the Writers' Co-op and I love that. I am so welcome to that. If you are somebody listening to this show, please tell me what you want me to cover and why you are the perfect person to do it. But today, we are talking about leadership mindset. And I will say, you know, our audience, mostly freelancers, who are probably like "I don't want to be a part of a team—"

Cynthia-Right.

Wudan- "I work by myself on purpose."

Cynthia-Right

Wudan- "Why does leadership apply to me or any freelancer?" So I want you to start this conversation by kind of telling us the conventional meaning of leadership, and on top of that, what do you mean when you talk about leadership?

Cynthia-Oo. I love that. Right, so I mean, I suppose the conventional definitions, there's many of them, but maybe the one that people think of the most is kind of like a corporate leadership...official in some kind of salaried context, where you're kind of rising up this "career ladder." And, you know, this predefined goal is like the corner office and you're wearing suits all the time. And you have a whole team and staff of people. It's very hierarchical and stuff like that. So I suppose that's maybe one definition that folks are talking about. And I started chuckling when you were queuing this up, because, you know, I mentioned I'm an introvert. I'm a big introvert. I love working by myself with myself not talking to anyone else. And yet, leadership is really important to me and how I run this business. And even before I had a team when I was, you know, essentially a freelancer, too. So I, I define leadership extremely broadly. So in contrast to that example, that I gave—I'm sure there's others that are, I'll just say, kind of in the box, perhaps, I define leadership super broadly. To me, it's if you identify a problem an opportunity, a gap of some sort, and you are coming up with and offering others a solution for it. And then the other people is kind of plus or minus actually. Like, you could work with and galvanize other people in the process of solving this problem, or improving things. Or maybe it is a solo endeavor, and you are kind of leading with yourself as the example for others. So that's how I define leadership.

Wudan- Yeah, kind of in the way of like, anyone who is doing something very service-based almost.

Cynthia-Yeah.

Wudan- Mhm.

Cynthia-Sure. I mean, you know, you could lead with a product-based business too, because every product has to solve some kind of need, you know?

Wudan- Yes. So what is What do you mean, when you say freelancers need a leadership mindset? What's the leadership mindset?

Cynthia-Right. So the mindset, you know, it's a lens, it's an approach, it's a framework, to how you do your freelancing, that, to me involves a number of things. One, there's like problem solving around your work itself. Like, maybe how to deliver better services, how to reach clients more easily, how to more efficiently do your work, so that you run your business, not the other way around. How to optimize things, you know, for yourself and also for—I'll throw in the lived experience identity piece too, for those of us who are women, non-binary folks, people of color, I actually think that there's a piece of that that is really crucial to us having to lead just by default of doing what we're doing. Because it's that whole, like representation matters kind of thing. And we are all kind of like a beacon to people whether we want to own that or not. So there's the problem solving around your work and your role in it. Then there's also taking ownership over your work. Like, there's no external boss that you're answering to. So it's important that we are clear for ourselves why we're doing what we're doing, and why we're doing it the way that we are doing it. What's kind of this bigger purpose or mission or goal behind it, even if it is a purely utilitarian purpose to your freelance work. Like, we live in racial capitalism. We need money to pay bills. Like, it's the way you want to be able to live the life you want, you know. But taking ownership over that, as maybe abstract as that sounds, like, there's a different relationship that we can have to our work, when we do have more of this leadership mindset for freelancers. We have to motivate ourselves to stay on track, to drive our work forward, to stay accountable to us, to our clients, to the work, owning what we put out there. So that's kind of a second piece of this leadership mindset to me. The third is knowing how to set the right kinds of goals for you and your business. This is a little bit more concrete. But being strategic, owning that piece of the work, so that we're not simply like mindlessly and unintentionally doing stuff in a rote routine, just "this is what I do" kind of way. And then the fourth and final one is being able to get on that strategy piece to think ahead, troubleshoot ahead, be proactive. We're in such a volatile time and have been for a while. I don't see that changing. We have to be nimble in how we adjust. How are things like global circumstances, AI, like all these shifts in work, culture and business culture, how are they impacting us? And how do we kind of get ahead of it?

Wudan- Yeah, And I wonder, you know, I want this message to be really loud for the people in the back, who are just like, I just want to toil in obscurity and provide my creative services. But why, like, succinctly, why is this kind of mindset so important?

Cynthia-Because it dictates the trajectory of your work life, which then, for most of us, impacts our life life. So to me, it's super important. Otherwise, we're just at the whim of any external factor. And I personally don't like us to ever be at the whim of things 100%

Wudan- No, and in a way, it also makes me feel like this kind of mindset helps us show up a lot more confidently—

Cynthia-Yeah

Wudan- — in front of clients, especially if we work in service industries, which many listeners of the show do.

Cynthia-Yeah. The reason that I love diving into this topic, and why it also is a little challenging to talk about, is because it's not necessarily the most concrete. So the shift may not actually look any different for any of the listeners on the outside, but it will feel different, not only to you, but to your clients, and others that you may encounter along the way.

Wudan- Well, it's giving it a name, right? Like, we could be doing all the things that you've already mentioned.

Cynthia-Yes

Wudan- But we might not internalize that of like, "Oh, we're being a leader in my field, my very small field."

Cynthia-Right.

Wudan- That is the case, right?

Cynthia-Yep it is absolutely naming it.

Wudan- So you talked about how this feels abstract. So can we talk about a few concrete ways in which this ownership or leadership can show up for people who are just a company of one?

Cynthia-Yeah. Well, I mean, you already named a big one, I think, for a lot of folks. And that's the confidence piece. People can feel a shift even when you don't think that it's obvious, or you don't think you're doing anything different, like you just said. So like a concrete example could be that you navigate a conversation with a potential client in a different way. Maybe you say more. Maybe you say less. Maybe you say something different. Maybe it's simply your energy that you're bringing to it. But that is a concrete way that things can show up. It might show up in your pricing. You could make changes to how you deliver your services and how you price them properly. And with adequate regard, not only for how great your work is, and also for whatever results it's getting for other people and the impact, but also because you are in a different relationship to your business, to your freelance work. It could also be trying new things, and taking different or other or more risks, like more calculated risks in your work as well, because I think that's also owning the pathway of your freelance and your other work.

Wudan- What do those risks look like? Or what could they look like?

Cynthia-I mean, let's say, you know, let's say somebody's, like a copywriter or something. It could be deciding to continue those services in a new way. Like maybe you think of how you can deliver those services, not necessarily like, on demand if a client hires you, but I don't know, maybe you create some kind of course, or a product around it, and trying that out. It could also be the opposite, which is like, "Oh, I actually want to decide to stop offering a certain kind of services that I do. I don't know, like editing or something. And I actually want to do more of this other kind of ghost writing." Yeah, I'm making these examples up. But making those kinds of decisions before you're functionally being forced to do so by external factors, I think is a massive step in taking ownership and having a leadership mindset over our work.

Wudan- Yeah, in preparing for this conversation, you know, I sent you a bunch of questions that I wanted to discuss. But at the same time, as we're having this conversation right now, I'm just thinking about all the like, very small and subtle ways that I personally have noticed how I'm applying this leadership mindset before I gave it this name.

Cynthia-Yeah

Wudan- Right. Like last year with The Writers' Co-op, I had a webinar on how to integrate SEO into your freelance business. And our guest is somebody who I know personally. He works at my co-working space, and he owns an SEO and marketing company. And he was saying, you know, if we want to be known as a photographer or a copywriter, in like Upstate New York, you have to say that very loudly, like all over your page, so people can find you.

Cynthia-Right.

Wudan- And even that can feel really uncomfortable, if people are just like, "well, usually I target a very specific niche," right? But let me tell you that a client of mine found me because SEO for "narrative journalist in Seattle" works. Yeah.

Cynthia-Oh my gosh, I love that on multiple, multiple, multiple levels, because I don't even know if you know this about me, Wudan, but I'm a big SEO nerd. I'm a huge fan of it in the various ways we can mark it and essentially let other people like you said, who are already looking for us. Like, I want everyone to, to recognize that too. Like, for those of you who provide services, or whether it's a product, whatever it is, there are already people out here who are looking for exactly you. But if they cannot find you, and they can't find that trail of breadcrumbs to you, you know, good luck to them, right? And good luck to you, because that connect won't happen. So it is our job as leaders in our own work, because again, no one else is going to do this for you, it's our job to make ourselves seen, heard, be in the right places. So those who are already looking can have an easier time finding us.

Wudan- Yes. Yes, for sure. And what else did I think of? Oh, I recently created a like two or three page Google Doc titled How To Best Work with Me.

Cynthia-Yeah.

Wudan- And I got the idea from my pal Anne Helen Petersen's podcast Work Appropriate, where they were talking about neurodivergence in the workplace, and how, instead of asking for accommodations, we can just give our co-workers, you know, a two or three sheeter, on how to best communicate with us, how to check in, how to communicate, so on and so forth. And I was like, "That's a brilliant idea." And it took me a long time to be like, "I'm gonna make that for my own business." And when I did, my clients are like, "We love this. This is so clear. I wish every freelancer did it." But...because it's a protocol of how to operate with you as a business.

Cynthia-Totally. And not only is it a protocol, it's also an asset for your business. And people don't think about that, because that thing has value. You've already explained how it does have value to you, but also to them. So that's a value add, which may or may not impact your pricing. We don't have to get all into that. But it's also part of the infrastructure now of your business. Meaning, it's something you can refer people back to. You're not recreating it from scratch every single time. Like, how much labor is involved in having the same conversation over and over? Not to say that there are times and places for that. But for this, you know, you can put it down, get clear on it. There's just so many ways in which that is a great example of taking ownership and leadership over your work, how you want to work, how you want other people to work with you. And yeah, clarity is a gift.

Wudan- Mhm. What else are some interesting ways you think that a leadership mindset can show up in freelance businesses?

Cynthia-So one, which your example just now reminded me of, is...also your two to three sheeter, like you said, it's a protocol, right? So in a way, that is also a system, in addition to being an asset. And systems, we all have them, whether we realize it or not, but doing that hard work of getting clear on what the system is, how you want things to go, could the system be improved, can we leverage different tools at our disposal to make it better for everyone all around, that is also a rather unsexy, but like, I think it's a cool way of exerting and exercising our leadership mindset in our freelance work, is being thoughtful about what systems do we need? What do we not need anymore? What needs updating, improving? And again, those then become also assets and valuable parts of your work. We may not even think of it. But I mean, I'll also just throw in an example. In my first career, when I was a public defender, one of the things we'd have to do is staff arraignments, which is when we get our new clients, they're folks who, you know, just been arrested in the last 24 to 48, sometimes longer, unfortunately, number of hours. And I started realizing over time, as I was doing that job, there's a set set of questions that I always want to ask a new client, but I was making them up as I went along, as I learned. But then it took me like a year or two to realize, "oh, I should just make myself my own kind of intake form, and then go through this with all of my clients." So you've also done this in your podcast process, right? Like you have a very clear set process, when you have new guest. This is what they get. Like, this then also allows you, for those who are interested, to scale or take on a team, you know, and it also helps when you're a team of one, because it helps future you—

Wudan- Yes

Cynthia-—do something more efficiently. And without making mistakes.

Wudan- Yes. Well, it's so funny because I think about my protocols like a scientist, because that's the industry that I was in before I jumped ship, right? And it was really impressed upon us that we should keep a detailed lab notebook of how we did everything. So if somebody you know, we were to quit grad school the next day, which I absolutely did, the next person could come in, follow exactly what I did, and help replicate my results. So yes, I'm a big systems person. I love systems.

Cynthia-I think that's a very good example. Because if we were to draw a kind of distinction between a freelancer mindset and a—and a more leadership oriented mindset, like freelancer version of me will be like, "I don't need a system. I know what I'm doing. I've done it a bunch of times. I don't need to write it down. I just do it, I show up. I'm there. And that's good enough. I'm not going to 'waste time' to turn this into a protocol, and make it accessible, and like, make sure it's numbered and all that kind of stuff." Who wants to do that? Right, like, most of us don't. But that would be like the freelancer approach. The more leadership mindset approach would be "no, this is an investment in my work and my future work. I actually really want to put this down. It will help me in the now time. It will help me in the future. It will help other people that I may not even see the benefit to them, but it will help them. And I'm going to hit pause on the million other fires I could be putting out and do this because it's important, and it's me taking ownership over the future of my freelance work.

Wudan- Yes, when freelancers tell me that they're in a slow system, I don't I always say what can you do now to invest in systems? Like, be kind to future you. I realized this last week as I was doing my taxes for this company, The Writers' Co-op, because it was the first year doing my own taxes for two LLCs. And, you know, I discovered, not too late, that I have to file to Schedule Cs. And as I was accounting everything, I was like, how I was doing things was so wildly inefficient, and that I immediately after crunching my numbers, I just like, created a new system. And I was like, thank God.

Cynthia-Yeah

Wudan- Thank God.

Cynthia-Oh my goodness. Like that, to me, just reminds me of...well when you were talking about the lab notebook, in my head, I was like, oh, yeah, audit trail, you know? And like, I hate to say that word and speak it into existence for us. But like, the truth is, we do have to protect our work and these kinds of things, it is really important. And again, if that's not persuasive, no one else is going to do it for us. So like, let's just make it better for future us.

Wudan- Yes. So we've kind of flicked at this creating systems, not only to be kind to future us, but perhaps we can use it if we're to become bigger. This season of The Writers' Co-op is all about expansive thinking. And we'll feature the stories of people who started out, you know, working just for themselves, and then decided to make something much bigger than themselves. And I am curious how this leadership mindset could transfer between running a company where you're in charge of other people versus being in charge of yourself, which is what we've been talking about?

Cynthia-Yeah, I mean it really becomes crucial at that point, because either—and I, there's no judgment here, this definitely both have happened to me, where I'm either scrambling to set up the systems, the assets, the protocols, even kind of file management, you know, like making sure stuff is not only on my local drive, but that it's in an shareable format to somebody else, you know? Like, all those kinds of things, really, really make a huge world of difference if and when you do bring other people on. And it can be even for a very part-time, concrete thing. Like maybe you subcontract out for one discrete project, right? But like, do you have even the most basic onboarding process, even if it's like three things? Like, okay, set up a Zoom with this person, and like, talk to them about X, Y and Z expectations. It directly translates into if you do want to expand beyond yourself, and that's where you can either spin your wheels a lot, unfortunately, which sometimes happens, or where you can have a more smooth process for leveling up in that very kind of linear way?

Wudan- Yes. And I feel like the other layer of scaling into an agency or just having a multi-person team is, you learn to be a manager. And maybe that's a different kind of leadership mindset. What do you think of that?

Cynthia-Yeah, I think that's where you get more into, like the traditional definition of leadership that we may be more accustomed to thinking of, frankly. Where you have somebody who's reporting to you and, you know, you sort of have to figure out how do you show up to this person to support them or coach them up, or facilitate them getting for themselves what they need in order to do the best job they can for the larger entity or mission or project as a whole? Then it becomes kind of this cool, I think, amalgam of the different definitions of leadership mindset that we've been talking about. You know, I think that's crucial. And, you know, one other thing popped into my head, Wudan, which, you know, thanks for bearing with the non-linearity of this, but when you were talking earlier about the "How Best to Work with Me" kind of thing, another piece of this is: At this juncture, when somebody starts working with others, it's really important to be crystal clear at that point of what is your mission? And what are your values? And if there's a vision, you know, what is that? Because those are the things that actually will galvanize and motivate other people to work best with you, which is to everyone's benefit, you know? But for freelancers, I could understand why that would be like, "I don't need that. Again, it's, it's me. It's in my head. It's in my heart. I know it." And also, it is important to externalize it, not only for ourselves, and to update it. But also to put it out there on your SEO on your website. You know, like, more and more, we're seeing people put their money where their values are. And so for who I understand to be in this kind of community here, and The Writers' Co-op, and everything you do, Wudan, like, this applies 1,000% to people who are listening. So again, just making the case of why doing this and adopting this kind of mindset is like a win-win-win on many levels.

Wudan- Yeah. What kind of barriers, Cynthia, do you see solopreneurs running into when they're trying to adopt this leadership mindset? And how do you think about overcoming them?

Cynthia-Yeah, great, great, great question. So I think one of the most common barriers is, it's like a time bias. It's related to that thing earlier, where I explained that example of why you might not want to write down a protocol, because it feels like you're wasting or spending time now ,when you could be like earning an hourly rate or something. Versus saving, actually, down the line, because you now have this asset that you can rinse and repeat and use again and again. So I think a lot of freelancers, there's that struggle to get out of that hamster wheel of like, time for money, time for money, time for money, to do some of these things that are non-billable, right? I recognize that most of us are not able to—or it's not a situation where you can charge a client or be selling a product for this time to do this thing. It's part of overhead. But there's an investment that has to happen at the front end, even when you've adopted or you're kind of "bought in" to the idea of like, "okay, let me start to adopt this leadership mindset." You still have to put in, kind of, the time and elbow grease, and the effort. And be okay with things being messy. Be okay with things being "wrong." Doing something. Doing it over a bunch more times. Like, that tends to happen. I think our discomfort with that happening and/or feeling like it's a loss, in the short term, can really trip us up on doing things that will be a win, like a much more massive win in the long run.

Wudan- It relates to my life motto of "progress over perfection," which gets me very far, but definitely not close to anywhere near perfect.

Cynthia-Yeah. Right. And, you know, like, we could interrogate what that perfectionistic stuff is about. How it came to us. Do we need to still subscribe to it? Like, that's a whole other podcast, really, but—

Wudan- That's a whole—yes. A whole episode about limiting beliefs and adopting this kind of mindset. Well, Cynthia, to wrap up, I am curious if, kind of a rapid fire question, what's one or two things someone can do to implement a leadership mindset in their own business once they stop listening to us? Yeah.

Cynthia-Yes, I would block time, at least 90 minutes—I'm a fan of at least 90 minutes—to think about what a leadership mindset could look like, for you. And yeah, I'm leaving that intentionally vague, because that is for that person to take ownership and leadership over what that is for them.

Wudan- I love that listening to you talk about this, I'm like, maybe I should add a values thing to how to best work with me. Because I do this, when I'm researching or looking for sources to interview for whatever, I love reading other people's about me pages, how they want to show up in the world. So in a sense, all of this is how we show up.

Cynthia-Yes. Yes. And it's so important. And also I want to recognize it is hard, a lot of times, to concretize that, to put it into words. Although most of the people listening, I think, will be real wordsmiths. But it's hard also to do for ourselves. Because it's hard to see the picture when you're in the frame type thing. It's always the hardest for our own work. I get it. And also just try it. There's another way you could do an action step from here. Take a risk. You know, put something out there, even though you think it might be wrong. Throw it on your website anyways, and see what happens.

Wudan- Yep, you could always delete it later.

That's right. That's what the edit button's for.

Wudan- Well, Cynthia, thank you so much. This was such a great episode. And I'm sure listeners will love it as well.

Cynthia-Thank you so much. It's always so fun. And I am just really excited for everybody to marinate on this more and keep learning from you and all the great work you are putting out there, and leadership that you are demonstrating every single day. Thanks, Wudan.

Wudan- Thanks to Cynthia for coming on the show. You can follow her on Instagram @embracechangeNYC, all one word, or learn more about her work at embracechange.NYC. Also be sure to check out their self-paced course called Jumpstart Your Online Business. It's designed to help freelancers and entrepreneurs walk through the process of crafting an actually effective pitch to land clients or customers. You get clear on what your offering is, and how you're problem-solving for your clients. It's very much in line with what we discussed today. You will definitely walk out with a tight elevator pitch to land your next client. Our Patreon members are already discussing this episode on our psychologically safe and inclusive Slack channel. Join us! Sign up anytime at patreon.com/TWCpod. Thank you so much for listening to The Writers' Co-op. This season is written, hosted, and executive produced by me, Wudan Yan. Our producer is Margaret Osborne and our editor is Susan Valot.