June 17th 2020
Carolyn Zhang (@carolynz) and I met over Zoom, just like so many others have in the new state of the world. The Brooklyn-based independent designer has worked with a range of clients from big companies to young startups and is now working through another "season" of freelancing. We chatted about all kinds of things, from what it took to make the leap, to her take on the future of freelancing, to what it means to make meaningful and creative work.
Can you talk a little bit about your journey into freelancing?
My first-ever freelance gig was actually while I was still in college—in 2013 or so, I started doing front-end development and graphic design for local startups and campus events. I was studying computer science but wanted so badly to do design that I’d prioritize the freelance work over my actual coursework in order to fill up my portfolio. After I graduated in 2014, I moved to SF and spent about half a year unemployed, trying to find a full-time design job. During that time, which was mostly marked by depression, anxiety, and general what-the-hell-am-I-doing confusion, I did some contract work here and there to pay the rent. Once I found my full-time job, I was busy enough that I didn’t really have the time or energy to moonlight.
This current period of freelancing, which started in May 2019, is my most serious attempt at it. I had been working at my job for four years, and I was reaching a point where I was like, “If I don’t leave now, I’m afraid that I’ll never leave. I’m afraid I’ll never learn how to function outside of this job.” Plus I was in the really lucky position of having no dependents, a healthy body, financial stability, no family to take care of… When else in my life am I going to have this opportunity to just kind of figure things out? This is my chance, and I’m going to enjoy this freedom while I can. I had a good savings cushion, so my initial plan was to take six months to reset and figure out what I’m going to do next, to approach things proactively (seeking out what I wanted) instead of reactively (reacting to the good and bad of my last job). The first month, I’m just going to take vacation… and then after that, maybe I’ll do some freelance work… maybe I’ll think about what companies I want to interview at… or maybe I’ll try to start my own thing, a startup or something… or maybe I’ll do personal projects, creative projects, explore new things…
What actually happened was: On my last day, a Friday, I tweeted about leaving. By the time Monday rolled around and I was unemployed, a bunch of people had reached out, and I was already setting up new business calls. It was mostly friends or people who I’d known and wanted to work with for a while. It’s so flattering to be contacted, and I was super intrigued by all these potential projects, and everything was so new and exciting, so I started those conversations right away. Then, by the Wednesday after I’d left my job, I had signed my first contract. It’s been pretty much nonstop ever since.
I was curious about things like setting up an official company and setting up my own contracts and getting a business bank account, so I went ahead and did those things too. You really don’t have to in order to freelance — I had been freelancing without those formalities since 2013 — but I did it just to learn.
As time went on, I kept adding more and more work to my plate. I didn’t intend to do this, but I was definitely subconsciously afraid of dipping into my cash cushion even though I had plenty of runway. I knew it was a good economy and an ideal time for freelancers, and I was afraid that it would end soon. I wanted to take on a bunch of work just to build up a second cushion.
The big question is always, “How do I get clients?” It seems like for you, you said you were going to leave, and you quit on the Friday. Then, by Wednesday, you already signed contracts. What do you think contributed to that, how you built your career, and the kind of capital you were able to build to get to that point?
Freelance is ultimately a network game. In many full-time jobs, the things that determine your personal success is the quality of your work, your ability to hit your goals, and your ability to manage the politics of the job. As a freelancer, you’re running a one-person small business, and in order to keep getting work, it’s ultimately just about who you know and who trusts you. You could be an incredible designer but not know the right people, and never get work.
My new business pipeline was half from Twitter (tech and design folks who followed me because of my employer’s brand, or because of my dumb design jokes), and half from college (people who didn’t know many designers, but needed to hire designers). My university didn’t have a design program, and my classmates are now at the age when they’re starting their own thing. They have a strong network of engineers that they know, both from previous jobs and from school, but they don’t necessarily know where to look when hiring designers.
Because it’s a one-person small business, you don’t need that much work in order to keep the business going.
For digital design, the projects are usually longer-term (for better or for worse), so you only need 1 to 3 concurrent projects to have a full plate. The long-term nature of product design in particular means that you don’t need new clients knocking on your door every day in order to stay busy. Contrast this with illustration or photography, which are often shorter one-off projects that frankly don’t pay as well for your efforts, so you need a higher volume in order to pay the bills.
What does your day-to-day look like now?
Now, I’m in a situation where I’m actually just full-time freelancing with one client, which is pretty much full-time work. Before this, I was splitting my time between two clients, so basically three days with one client and two days with another, and I’d alternate my working days with each client to try and maximize efficiency. Working nonconsecutive days makes it less likely that I’ll be blocked on feedback. The potential downside is that there’s a lot of context-switching, but I only feel the pain of context-switching when I’m working with multiple clients in the same day.
I worked with one team on-site in New York, and the other remotely, since they were in San Francisco. They were both small start-ups, and I would just be doing a mix of web, product, and brand design work, depending on what phase of the project was happening and what the client needed at the moment. It was very fluid — one day, you need a new logo, and the next day you need a new product feature.
In an ideal world, I try to do most of my generative work in the mornings; avoid email, Slack, social media before lunch; and only schedule meetings in the afternoon. At the end of every day, I do a design review with the client to go over the day’s work, either via an in-person meeting or a video call. It’s a habit I picked up from my previous job — when I do reviews at the end of the day, I can let feedback sink in overnight and start the next day with a plan; if I start the day with a review, my work for the rest of the day feels reactive.
And after the end of the regular workday, I’d do any administrative stuff related to my own career or business — answering emails, sending invoices, etc.
There’s a bit of structure that you’ve built in. Is that from your end or more so from the client’s end, or does it depend?
That was from my end. I realized in the first few weeks of freelancing that the lack of structure in my day (working from different places, working at random times, meeting all these different people) was causing a lot of unnecessary anxiety and distraction. Having a predictable cadence to my day helps center me.
My approach to working with anyone is to have really frequent check-ins and conversations, to stay motivated and to minimize miscommunication. It becomes especially important for small startup clients, where everything is changing so fast that you need to talk frequently to have as much context as possible. It’s impossible to always have full context as a freelancer or outside agency.
I know other folks that like once-a-week meetings, or just written feedback over Slack or email. That can work if things are changing less frequently on the client’s side, or if there’s a familiar working relationship, or if the client is great at setting up a project well and giving clear and actionable feedback.
At this point would you ever go back to a job, or are you really enjoying what you’ve built with your freelance work?
A rewarding full-time job can certainly be appealing: having just enough stability to be able to focus on the actual work, diving deep into a space that I can stay interested in for a long time, and learning from a great team.
When I went freelance, I went from working with mostly designers, to working with no other designers at all. I was lonely and frustrated because it was a lot of new relationships to handle at once. A lot of different cultures and different values for decision making, which can feel thrashy to jump between day-to-day. Normally, when you switch jobs, you have to unlearn the decision-making values and culture of your old company, and adapt to how things work at the new company. Going freelance was like adapting to 4 different new sets of values at the same time — and while I learned a lot, they weren’t necessarily values that I really wanted to keep working by for extended periods of time. That’s not to say that I experienced bad working environments; everyone’s actually been very easy to work with. It’s just that what was best for my startup clients — usually something simple, not-broken-looking, easy to build and maintain, and done quickly — was not necessarily the type of work that I wanted to be doing for the long term.
This is just my own experience in this period of freelancing, with this set of projects. One thing I’ve heard a lot from other freelancers is that it’s hard to feel a sense of career growth when you’re freelancing, unless you have a super clear idea of what you want. I’m definitely feeling that. I didn’t really know what I wanted when I started freelancing, and I still don’t have the clearest idea of where I want to go in my design practice. But usually, after I do the same thing for a while, I want to mix it up and do something completely different.
It makes sense for a lot of creative people who are like, “I kind of sometimes just need to have that one job and then sometimes not, and it’s not necessarily like I’m tying myself down and being like, ‘I need to do this way of work forever. I just kind of have seasons of things.
“Seasons” is really the right word for it, because it’s not like I’m trapped in one mode forever. It’s just like, “Oh. This current phase.” I’m in a season of freelance work, and I’m open to seasons of full-time work. Going back and forth between the two sounds good.
It feels like a common misconception that people have, where even new people who are nearly graduated. They’re like, “I really want to go freelance. I don’t want to work for anybody. I want to do freelance, and I want to be in freelance forever, because it is ultimate freedom”, but it barely works like that. Then, a lot of people who are freelance kind of go back and forth between full-time jobs too.
There’s financial freedom and creative freedom, and honestly neither is guaranteed for freelancers. Often you are getting one at the expense of the other. And in a bad economy, you might be stuck with neither. You can only turn down creatively unfulfilling projects if you have the financial means to do so. Plenty of folks have a day job — to help ensure their financial freedom — and do freelance work or personal work where they can exercise their creative freedom.
Going back to what you said about loneliness, is that what you find most challenging about freelancing?
In the beginning, it was the sense that I didn’t have anyone to bounce ideas off of, and that I didn’t have anyone who “got” design to give me feedback. I really missed having that culture of really pushing the design to just the absolute best it could be. Startups need easy-to-build, easy-to-maintain designs, and generally only need a good-enough version of most things, because the much bigger problem is figuring out how to keep the company alive. It makes total sense, but it was just such a big shock for me coming from a team of perfectionists that really focused on the details.
At one point, I just signed up for too many projects, and didn’t set end dates on my contracts. Everything was exciting and sounded doable individually, but I forgot to account for the context-switching cost that gets added with each new project and client. I was just way too busy, half-assing everything, and I was like, “Why am I even doing this? This isn’t what I set out to do.” I got caught up in the rush of new work, but burned out since it wasn’t sustainable. I tried to stop all my client work, but I’m still bad at saying no to new things that come up. Getting better, though.
As I burned out, a lot of the business tasks of freelance that I had to manage by myself — things like expenses, invoices, etc. — fell into disarray too. And I’m still playing catchup there. I haven’t tracked my expenses since September, yikes.
How have you found learning the business, sales, and marketing side of freelancing?
It was pretty straightforward for me, partly because at my last job, the founder was a freelancer and I joined just as he started building his team. I just adopted all his freelancer habits. Through my agency background, I’ve also developed a good spidey sense for who will be good to work with, so I was able to avoid toxic clients. The freelance designers I knew were also very generous in sharing resources and tips with me.
All that, I feel, really set me up for success in the beginning. It just felt like running a one-person agency. I didn’t do much active marketing work, because I had enough work to sustain one person. If I were trying to run an agency, that would be a pretty different game. More people means more overhead, and more projects needed to keep the lights on; I would need to really turn up that marketing and PR machine in order to get more business.
Aside from client work, where are you hoping to take your freelancing?
Before COVID-19, I was really interested in doing more experimental design work, maybe getting back into code, playing with machine learning stuff as a creative tool. And I had realized that I couldn’t do those things while I had all this client work going on, because client work is my comfort zone at this point. It’s so much easier to do work that other people need and are asking for, rather than to explore what I want, which is undefined. I was hoping to wind down my freelance work for a while and work on self-initiated projects.
But when all this COVID stuff happened, I knew the uncertainty would send my anxiety haywire, and I scrapped all those plans. I looked for stability in everything I had control over. So I’m still full-time freelancing with my one client, and learning how to basically operate in-house.
The next time in my life when I’m able to just have three months of uninterrupted time, I would like to pursue more experimental and creative projects, learning new tools, exploring different ways of thinking, or making novel work that I haven’t seen before — work that’s not necessarily commercially viable.
Or maybe just doing something completely different, not related to tech or design. For a while actually, before I left my job, I was like, “Maybe I should just go apprentice at a neon shop or something to make neon lights,” because I really loved doing that too.
Do you think the future is freelancing? What kinds of things do you think need to change in order for more people to become successful as freelancers?
I don’t know if the future is freelancing, but I can offer my observations. I see two classes of freelancers. One is the gig economy workers who are forced into freelancing, because they’re being preyed upon by companies exploiting a legal loophole to get away with paying their employees less and not paying for benefits, health insurance, and all of that. It’s not just the Uber and Lyft drivers, it also includes freelance writers and illustrators who work in struggling industries like media. They’re all very vulnerable members of the workforce.
Then, there’s the much more privileged class of freelancers and consultants and independent creators, who are much more empowered to move about and pick the projects that they want to work on and have the freedom to set their own hours and such, which I feel like I belong to. I recognize all the advantages I’ve had in my own freelance journey, starting from early cash cushions, the mental sense of having a safety net, and feeling secure enough in my employability that I could walk away from potentially toxic clients. I have a good network of people who have access to lots of money and treat their collaborators well.
There’s this tweet that I’ve been thinking about a lot. I’ve tried to find it again but can’t — it was something like, “your parents moved here for grad school, my parents were refugees, we are not the same.”
There’s parallels to these two classes of freelancers. In the immigrant example, these are both seeking a better life, but one is more empowered to do so. The other is escaping persecution and war and violence. One is a proactive reach, and the other is reactive escape, if it could even be called an escape. More like, being forced into a path.
There’s a lot of macro forces shaping the freelance experience, from labor policy to technology. Software helps individuals be more productive and gives them a lot more resources to run their small business, which is great for freelancers and entrepreneurs. But it’s also siphoned money away from traditional advertising and media companies — which makes them turn to underpaid freelancers. And since everyone expects internet content to be free, a lot of creative work has been devalued.
We also see different countries treating their freelancers very differently. In the United States, there’s much fewer social services and protections for freelancers than many countries in Europe. I would love to see a world where anyone who wanted to, could become independent and work on their own terms. But it would absolutely be devastating if everyone were the other type of freelancer, where you’re actually just a cog in a broken capitalist machine.
I see it as being ultimately about the power dynamics between the person receiving the money and the person paying the money. For more people to become successful as freelancers, there needs to be a continued structural shift in power towards these individuals. When people talk about labor and power, it’s traditionally been about workers collectively organizing to get bargaining power against their employer, and I’m all for that. But I’m also excited about the new power structures and business models that the internet makes possible for individuals. The iconic example is Ben Thompson running Stratechery, a popular subscription-based newsletter with tech business analysis—he just does his thing and writes for his niche, his audience will pay good money for it, and I’m sure he makes a mind-boggling amount of money for his time spent working. A one-person business of that scale is only possible with the internet.
So there’s a plausible path to building a successful one-person business by finding a niche, building your brand and audience, and making money through subscriptions, merch, client work, or some combination of all that — whatever works for you. I’ve basically done a very modest version of that.
But I also know so many people who have a huge audience on Instagram or Youtube but still struggle to get projects and pay the bills. It’s a very tricky path depending on what niche you’re in. So, making it easier for people to bridge that gap between audience and money, and improving social services (e.g. healthcare) for individuals pursuing that path, are big parts of what needs to change for more people to have a successful independent career.
Last question! Now that you’ve settled in a bit into freelancing this time around, do you feel more creative and fulfilled with where you are and what you’re doing?
Clients come to you looking for things that they know you’ve done, or things similar to what you’ve done before, and you reach for a familiar set of solutions. The more familiar it gets, the less challenged and less creative I feel.
Right now, because everything about my freelance setup still feels new, I do feel more creative than I was at the end of my last job. That being said, because I’m working with a bunch of B2B SaaS startups, there are very similar constraints across all my projects. I can be creative in terms of how I work within those constraints, but there are certain types of high-production-value work, or certain “styles” or “genres” of work, that I know are just completely off the table.
I’ve enjoyed learning from all the different company structures and cultures. I’m learning how to get things done when you’re really embedded in a team, and really just learning about everything outside of design, from my collaborators in other disciplines. I like to take ideas from their worlds and adapt it into my own practice — for example, how the PM sets up projects might translate into how I set up projects as an art director.
And above all, I’ve been spending a lot of time thinking about what matters. To me, to the end users, to my clients, to the world. I started thinking a lot this when doing heavily-constrained work, and I think about it even more now that COVID has hit and we all have a clear reminder of what work is “essential,” and what is not. To some extent, it’s demoralizing because plenty of things I care about seem trivial in the grand scheme of things — picking the perfect typeface, making sure things are aligned on a grid, getting the easing of an animation just right. But it also helps me look at my familiar work with a fresh set of eyes. Does this feature help the make the product better with each use? Am I helping the team communicate more clearly and work more efficiently? Do these designs legitimize the right people, and the right companies? Does this work help create a world I want to see? It’s been a hard but creatively enriching process.
-As told to Ana Wang, April 2020. Transcribed and edited for clarity.
Illustration by Adamastor