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Meet Olivia Gagan – a super savvy freelancer

By June 14, 2024 10 Comments

Olivia Gagan is the kind of writer that many people aspire to be – she’s a full time freelancer living in London, having written for titles such as The Times, Psychologies and The New York Times. Olivia cut her teeth working as a journalist for trade media before making the decision to go full time as a freelancer. She transitioned to full time freelancing in such a smart way; by building up her savings, drawing on her existing networks, establishing boundaries and learning about running a business. I hope you enjoy the interview – there’s absolute gold here.

Meet Olivia Gagan – a super savvy freelance writer

Can you tell me a little bit about yourself and your path to becoming a freelance journalist?

I’m a full-time freelance journalist, living and working in London. Writing has always been my thing. I used to write and illustrate little books and pamphlets when I was a kid, which I realise now were essentially my version of a newspaper!

I studied English Literature at university – then graduated straight into the 2008 recession. I couldn’t find a writing job for toffee, so I was waitressing for a while, until I got the funds together for a journalism course (the NCTJ, which is a British qualification for journalism). That took a year, and I’ve worked as a news and features journalist ever since.

What kind of split do you have with the type of writing you do?

At the moment, I’d say the split is 70/30.

Seventy per cent is articles for newspapers and magazines, and 30 per cent is writing reports, speeches and website content for companies.

I used to be a bit of a purist and only wanted to write news and features – I then very quickly realised I needed to be able to write across a variety of mediums if I wanted to make a living.

Which publications do you tend to write mostly for? Do you have a niche?

I guess I have a couple of niches – I write a lot about sustainability and renewable energy (which was my beat when I was a full-time business journalist). I’m commissioned by Raconteur, which is a business supplement in the UK’s The Times newspaper, most months to write on that topic.

At the other end of the spectrum, I write a lot of culture articles (interviews, reviews, think pieces) for magazines like Psychologies and websites such as Refinery29. I write a essays and profiles for a great Dutch title called Flow, which also has English, German and French-language editions.

You write a lot of profiles. What do you like about this type of writing, and what do you think the key is to writing a compelling profile?

I love profiles because I’ve always felt it’s a privilege to get to sit down with someone for an hour and talk about their lives. People are endlessly fascinating and given the opportunity, most people love the chance to talk about the choices they’ve made and what they want out of life.

Things I’ve learnt about doing profiles: there’s a skill to making someone feel comfortable and like they want to open up to you. You have to establish trust really quickly. I try to do plenty of research beforehand, ask original questions, and give people room to breathe and talk.

I feel particularly in women’s magazines, there’s a script for interviewing people (‘She walked in wearing Acne boots, wrapped in a $1000 cashmere sweater…she ordered an egg white omelette’) and I try as hard as I can to deviate from that script and talk about the interviewee’s work and how they see the world and current issues.

All that said, I struggle with the transcribing element of interviews; I’m really slow at it. I recently interviewed seven people in one day. Transcribing seven hours of me talking is hellish! (I recently decided to invest in using Rev.com for transcribing, a tip I picked up from your site, Lindy, so thank you!)

You went full time freelance in August 2017. I’m interested to hear about what you were doing before you went freelance, what prompted you to go freelance and how you’ve ensured that you have plenty of work.

I was working full-time as a news reporter for a trade title.

I really enjoyed it – I got to travel a lot and I was writing every day. I’d then do bits of freelance work in my spare time, trying to build up a portfolio and expand into consumer magazines and newspapers.

In early 2017 I had a secondment to Paris, where I was working on my own for a few months. I loved it – and I realised I could work alone. At the time, I also felt constrained by the limits of my job, and I started to wonder if I’d be able to build a career I was really excited about if I became self-employed.

I found the prospect of going freelance terrifying at first; I don’t come from a wealthy family, so being able to look after myself financially is really important to me. About six months before I went freelance, I came up with an exit plan.

I built up some savings so I could support myself, did loads of research into starting a business, got my website up and running, and started talking to friends and industry contacts about potential work before I finally handed in my notice.

It meant working in the evenings but slowly phasing myself in to freelancing was essential for me.

I get the attraction of going nuclear and just jacking in your permanent job without a plan, but I needed to take very considered baby steps. I also had a tonne of gentle but firm encouragement from my family and friends – I think they could see I was ready for a change.

In terms of making sure I have work – the ‘marketing myself’ side of things can make me feel uncomfortable, but it’s been essential.

I post articles I’ve had published on social media, I make sure I’m in contact with old and current employers, and I tell people all the time what I’m doing and that I’m available. If I’m having a quiet week, I update my website and draft pitches to send to editors.

You initially had difficulties juggling the expectations of multiple clients – could you tell me a little bit about that?

I’ve found if I’m not careful I can slip into people-pleasing really easily. I was picking up non-essential calls from editors at 8pm on a Friday night and responding to work emails on a Sunday; if you’re a freelancer there’s often an expectation that you’re always ‘on’ and available.

How have you addressed that and how do you now manage clients’ expectations of your time?

The irony of going freelance so I could write whenever, wherever I wanted…is that I’ve now decided to work 9am-6pm, Monday to Friday. Office hours, basically. For the first few months, I’d work through the weekend and until 9pm, while everyone around me had clocked off and was relaxing, and I was getting resentful.

So now when I start working with a new client I outline the hours I work, when I’m available for calls, and how quickly they can expect me to respond.

I don’t pick up the phone outside of 9-6pm and I’m trying not to check my email outside of those hours as well. I think boundaries are important – it’s made me feel less stressed and people know what to expect from me.

Nowadays, what’s your favourite kind of writing job and why?

Profiles, and I also love writing longer-form articles about current issues – anything that feeds into a wider conversation about the way we’re living.

It’s always a thrill when an editor accepts a feature pitch. I wrote a piece for Refinery29 on renting problems in the UK (house prices are absolutely extortionate here) and I was happy I got to give people who are making exciting work about the issue a voice.

Do you have a writing routine? What does ‘a regular week’ look like for you?

Outside of sticking to a 9-6pm schedule, my other constant is to write a list as the last thing I do each day, then try and work my way through it first thing the next morning.

Being organised is absolutely essential, because with multiple clients, queries and invoices flying about it’s easy to lose track of what’s due.

This week I’m writing up those seven interviews, I’m writing a series of articles for a sustainable fashion website and I’m writing a piece on a trend in the energy industry. It changes every week though – some weeks it’s not exciting at all, and I’m just chain-drinking tea and ploughing through admin and emails. 

What are your favourite ways of finding clients?

Being recommended. I’ve just been referred to a new client by someone I last worked with eight years ago, which just goes to show how important your working relationships can be. However, I didn’t know any other journos or interview sources when I started out and I wasn’t well connected at all – a lot of my work has come from cold pitching. I’m a big believer in approaching people and publications you admire with ideas.

What do you find most challenging about being a freelance writer?

I do miss the buzz and chatter of an office. I don’t actually find being alone too much of an issue, but I’ve noticed my mood and my productivity can dip if I’m not out and about meeting people every week.

And the best thing?

The ability to decide what I do with my time and to make long-term plans for my writing and work. I feel a lot more in control, because I get to write the job description.

Anything else you want to add?

I’ve been surprised by how many people have asked me about the mechanics of going self-employed. There’s a lot of ‘Earn A Bazillion Dollars In Your First Day Freelancing!’ websites out there, but not many that talk about the nitty-gritty of starting up a business.

Lastly, how can people get in touch with you?

My portfolio and all my contact details are here, and I’m also on Twitter. Come and say hi!

Thank you Olivia!

I just love how strategic and sensible Olivia was when she was looking at going full time freelance – what did you like about this Q & A?


  • Claire says:

    What an inspiring woman. I love how Olivia was certain right from the start that she wanted to be a journalist and that she made a plan and stuck to it. And great to hear from someone who is doing well writing about sustainability and who is also a UK writer. I completely understand the fear aspect she mentions, I feel very much the same about freelancing. But with hard work things do build, both work and connections – like Olivia I started out with neither, I didn’t know a single person in the writing business. A great interview, I really enjoyed hearing her story.

    • Lindy Alexander says:

      Thanks Claire – yes, I felt the same! How encouraging that she writing about big, important issues and making a living from freelancing full time. I think there are lots of parallels with your story! Thanks, as always, for your comment.

  • Rashida says:

    I really enjoy these insights into the lives of other freelancers. Olivia definitely took a considered leap into freelancing which is the way to go I feel. Whenever I read these kinds of articles, it gives me a buzz and reminds me why I love to write. Great interview Lindy!

    • Lindy Alexander says:

      Thanks so much Rashida. I feel the same – I always come away so inspired and I learn so much from these Q &As. Thanks for your comment 🙂

  • Kylie says:

    It is great to hear from another freelancer who has a passion for profiles and has found success doing what she loves. I can relate to the feelings that Olivia describes when hearing and sharing someone’s story. Thanks for this interview Lindy and Olivia, it has inspired me to chase more profiles!

    • Lindy Alexander says:

      Thanks Kylie! I love how Olivia is writing a different kind of profile (I was vigorously nodding my head when she talked about the usual kind of women’s profiles you read!) – do let us know how you go if you pursue more profile writing.

  • Cathy says:

    I found everything Olivia said really interesting. I found her comment about making her writing different from what is out there really informative. A really great interview. Thank you Lindy and Olivia.

  • Anne-Liesse Persehaye says:

    Thanks for this interview, Lindy! I loved reading about Olivia and how she handles her job on a daily basis.

    I LOVE writing profiles too, but find the transcribing part excruciating as well. Rev does not offer services in French if I’m not mistaken and I yet have to find transcribing services I can afford. But other than that, it’s great!

    I’m off to doing an interview now! God I love my job! #luckyashell (on some days at least!!…)



    • Lindy Alexander says:

      Thanks Anne-Liesse, so glad you enjoyed this interview.

      That’s tricky about transcribing – I wonder if there’s scope for Rev to offer a french transcribing service …

      Hope your interview went well 🙂

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