How Designer Olivia Charlesworth Found Clients and Built a Network in a New City

What do you do and what kind of clients do you typically work with?

This is a tough question, but it’s ok. I am getting better at answering it. I am a graphic designer who likes to try a bit of everything. Design is cool like that. So, typically, the project I work on isn’t something I’ve done much of before but I use the experience from the last to inform the current. I hope that this leads to a more interesting and unusual outcome. Right now, I am designing websites and packaging, before that I designed an album cover and before that I ran a photography workshop with a friend. I sometimes find my own clients and other times work in studios or agencies on a freelance contract.

Can you describe your journey into the world of freelancing?

After I graduated from Kingston School of Art I became a kind of serial intern on a wild safari ride through design studios in London. I was determined not to take the first full-time job that came along. I was eager to keep learning and meeting new people. After doing this for a while, the internships morphed into freelance gigs which meant I could drop the Camden pub crawl tour guide job I had on the side. It was tough being a junior freelance designer though. I felt the pressure to deliver but sometimes lacked the experience to know how. That said, I think I secretly liked the challenge and, besides, everyone is just making it up as they go along aren’t they?

I took a full-time design job at Wieden+Kennedy when I felt ready to commit to a company. Over time I had developed a strong sense for creative places that felt good. I never thought I’d end up in advertising but really enjoyed working alongside art directors and copywriters. Two years later they let me go, so I went back to my familiar freelancing ways before thinking “Actually, fuck it – I’m going to move to New York and start over.”

What does your daily schedule look like at the moment?

In light of the current events I have two answers. (BC is for Before Covid-19 and DC is for During Covid-19). Life is different for everyone during this time and it’s necessary to acknowledge that.

BC: I work between two studios right now. I have a desk space with some good people at XXXI on East 9th Street and I am working with Human (also good people) in Chinatown. So, I get to choose where to go in the morning. I wish I could tell you that I wake up early and go to a gallery or read poetry before I start work, but honestly a walk through the East Village listening to music is enough for me to feel inspired. The first thing I do when I open my laptop is write a list of what I need to do that day. Then I get it done. That list could involve a bunch of things like coming up with ideas, letting myself get lost in some visual exploration or tidying up design bits on a lingering project.

DC: I try to get out of bed before 9 AM. Maybe I’ll shower, maybe I won’t. I saunter into the kitchen to make coffee and then head to Studio Olivia, aka my bedroom, where I just was. I write a list, then I get it done. Internet radio stations keep me company all day as I sit at my fold out desk. I break for lunch. At random moments of the day I just sit on my stoop and think about stuff. Sometimes I get a lot done, other times I don’t. It’s okay either way as it seems to balance out by the end of the week.

You recently moved from London to New York; how did you find the transition in terms of finding new clients and building a new network?

I think you can engineer luck and I think that’s kind of what I did. I came to New York with some savings and I stayed for a month in an Airbnb (which is now my home, but that’s another story). The plan was simple: meet as many people as possible. I’d set up a bunch of meetings with agencies and studios before I left. ‘Hello from London’ read the subject line of each email. Thankfully, most replied and were happy to talk. Some of these contacts became my friends and, to my surprise, Google Creative Lab offered me a freelance gig, so it just fell into place. I feel very lucky but also know that my experience freelancing and interning prepared me for giving it a go in a new city. Although I was born and bred in the UK, my mum is American and my dad British, so I have dual citizenship, which entitles me to UK and US passports. I feel very fortunate to be in this position and wanted to make the most of it.

Would you say that there are any marked differences between the two cities with regards to the freelance scene?

In New York I have met many more people who work for themselves and find their own clients instead of doing freelance stints in studios and this was really inspiring for me. Another thing I have noticed is that hardly anyone I knew in London worked in-house, whereas they do in the US. At first, I thought in-house was kind of lame but now I understand the context around that choice. The cost of living in New York is higher and healthcare is tied to employment. Oh, what a luxury it is in London to work exclusively for small studios that focus on cultural, artful projects!

Did the business side of things come naturally to you?

Erm, no. I joined Instagram a few months before arriving in NYC because I thought I should probably have more of an online presence. Taxes and things like that are confusing and, to be honest, I’m still getting to grips with how much I should charge. The best thing to do is talk to people about it. I ask friends and have frank conversations about money. Women in particular need to do this!

How about the freelance lifestyle – does it suit you or do you prefer the structure of going to the same office and working for the same company each day? Also, how do you provide your own structure without these things?

I left Google because I’d been there nine months longer than I was expecting to and I was itching to get out and explore what else the city had to offer. I like things to feel fresh as it has a positive impact on my ability to create. Being in charge of my own routine is the biggest attraction of freelancing to me. I think it’s hard to go back to a full-time job once you experience that type of freedom. I love being able to take advantage of an unexpectedly sunny day, or be able drop work for an hour to meet a mate. I do recommend that anyone who is going freelance should try and find a desk space or at least somewhere to work that isn’t their home. I find that a commute and someone to eat lunch with makes a big difference to my productivity.

You’ve been freelancing for quite a while now; what have been the highs and lows?

The shit thing about freelancing for agencies and studios is that sometimes you just touch projects for a short period instead of seeing it through from start to finish. This means I have done a lot of work that I can’t really talk about. However, now I work much closer with the client and even find some clients of my own, so I get to experience the entire process. Another thing about full-time work that I sometimes miss is having a team. I liked having colleagues that turn into friends because you see them every day. I learn a lot from others and enjoy the camaraderie of a permanent team.

It’s also worth saying that when I was just starting out as a freelancer, I definitely cried a few times because I had no idea when my next job was going to come in or because I hadn’t the foggiest idea about how to do my taxes. Freelance anxiety is real!

The highs of freelancing are continuingly proving to myself that I can do something on my own, having the time to teach and being able to take extra-long holidays when I feel like it.

What key lessons have you taken from it?

I think freelancing has helped me to separate my work from my personal identity. Designers can often be harsh on themselves because the work they’re making or the job they have does not perfectly reflect them as a person. Freelancing has taught me to value my time differently. If I make work that I really love then that’s great, but it’s also ok to not always be in love with it and instead just get the job done so I can go outside and be the rest of who I am. I feel very privileged to be able to do that and I try to remind myself of that regularly.

Would you ever go back to a permanent job? If so, under what circumstances?

Never say never! It is likely that I’ll eventually crave the security of a regular paycheck. It is also likely that a studio or agency could win me over because I’m into what they believe and the vibe feels right.

-As told to Daniel Milroy Maher, April 2020. Transcribed and edited for clarity.