Interview with Jillian Richardson

Freelance Writer

Jillian Richardson is a freelance writer based in New York, New York. We talked about going viral, humanizing brands, and taking charge of your business. Check out her website and Contently portfolio to learn more about her work. You can find her on Twitter, too.

Your work has appeared on the Freelancer by Contently, the Establishment, the New York Post, and more. Which stories are you most proud of and why?

I really like the work I’ve done for The Establishment. I’ve written personal essays about sexuality. For me, the pieces that make me the most anxious and nervous are the ones I know I definitely should be writing. I wrote about taking an orgasmic meditation class to help me understand why I can’t orgasm, which got a lot of attention. A lot of women reached out to thank me for putting their experience into word. That was one of my proudest moments.

I wrote a piece for Quartz about why co-working spaces should have sexual harassment policies. That was difficult to get published, because many publications are involved with co-working spaces and didn’t want to slander them in any way. It took me eight to nine months because a lot of places wouldn’t touch it, but got a lot of great responses after working with Quartz.

Some co-working spaces told me they hadn’t even thought about sexual harassment policies, but started making ones.

When did you start freelancing?

I started part-time freelancing when I was 19. I had an internship at Contently. When the internship ended, they offered me a freelance position. I got lucky and started writing about content strategy and the gig economy.

How did you land that internship?

I was at Boston University. I applied for the job because I knew I wanted to work in New York City over the summer. I met with Joe and Jordan in their offices, back when it was one floor before it blew up. I remember Joe really liked I was into comedy and that I wrote for The Bunion, the school newspaper. He liked one piece in particular that went mildly viral on the internet. At the time, I was surprised about what they cared about compared to writing about marketing.

What was your first story about?

I don’t remember exactly, but it was definitely something about content strategy. It wasn’t exactly what I imagined my first freelance article would be about, but that’s how I got my first freelance gig.

What do you enjoy about freelancing?

I love the flexible schedule. I love waking up and doing work immediately. I work well in the morning, so it’s awesome to make breakfast and do two hours of work and it’s only 9am.

What don’t you enjoy?

I do not enjoy the financial instability. That’s something I’m really working on right now — figuring out ways to get contracts from creative agencies and brands. Starting the month not knowing how much money you’re going to make can be terrifying. I’m lucky I have savings, so I know I’ll be okay no matter way, but it’s exhausting to be starting at zero.

Talk to me about your copywriting services like live-tweeting for conferences.

The biggest thing I do right now is writing blog posts for companies in a way that humanizes them. I notice a lot of companies struggle to communicate what they’re passionate about and their message in a way that’s fun and understandable.

I write for companies that have a complicated message so people can just as excited as the people who started the company are.

I also cover events. Sometimes, it’s real estate conferences, finance events, or tech conferences. I have to find a way, especially with Twitter, to summarize what’s going in a concise way. That’s a skill not everyone has. It’s awesome when a freelancer can do that for someone running event, so that person doesn’t have to worry about it.

What values are important to you as a writer?

One is definitely hustling. I know it’s an overused buzzword, but it’s so important because no one is telling you what to do, when to do it. No one cares if you make enough money except for you. You need to figure out a way to make it work for yourself. You need to be okay with not having a boss. I ended up getting a career coach for that reason, to have somebody that knew the context of the career and what was happening. I started to feel overwhelmed that everything I did was on my shoulders lone. I find it helpful to talk to someone once every other week to let off some steam and share the challenges I was facing.

What message do you have for the Millennial Freelancer’s audience?

If you want to pursue freelancing part-time or full-time, look at it as a business. That was something I didn’t do for a while. I pitched pieces and let my career happen, letting editors shape how much money I was making.

Then I heard someone referring to their writing as a business. I needed to learn about marketing and pipelines to figure out brand’s weaknesses so freelancers can help them.

At least initially with freelancers, they say to make a website and start getting some samples, but no one says before you start, learn how to run a business. That’s where lot of freelancers struggle, that’s where I struggle.

Additionally, find an online community. For instance, join American Society of Journalists and Authors. It gives you professional credibility, but also a group of people to be able to reach out and just ask a question. People always reply and want to help you out. It’s nice to have that support when you’re in a job that can be really lonely sometimes.


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