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Quick chat with Rosalyn Page

You’ve had an interesting career journey that’s taken you overseas for a stint and has given you bylines in some big names. What have been your most memorable career highlights?

Still being here, while having had two children, working part-time for years and riding the waves of tech-driven changes that have upended and fundamentally altered publishing over the last 20 years. A few bylines and articles that I loved seeing in print. Helping consumers with their tech and advocating for fairer rules in my time at CHOICE.

Best bits and worst bits about working for yourself?

Flexibility! I schedule my exercise every day and almost always have time because I’m not commuting and not bound by set office hours. I also like running my own show. Choosing how and when I work, connecting with people and it feels more interesting and exciting as work’s always a bit different. 

The hardest bit is dealing with pricing, investing time on emails and calls about prospective work that doesn’t always happen, chasing invoices and feeling like you have lots of bosses/editors instead of just one.

Business technology is one of your niches which is interesting given the hoopla around AI at the moment – and you’ll be talking at the Summit around how AI might be impacting getting work at agencies. Interesting times, or nerve-wracking?

Both! I’ve written about technology for over 20 years, business and consumer, so it’s been incredible to see the changes and the amazing innovations in that time. But the latest, with generative AI, is really shaking things up across so many different professions – and it’s happening at light speed. 

Generative AI… is really shaking things up across so many different professions – and it’s happening at light speed.

What are your thoughts on using AI / ChatGPT yourself?

If you’re not a writer or editor, I think you’re more likely to be blown away by ChatGPT and generative AI. Having seen brilliant sub-editors at work who could turn out smart, pithy headlines, I’m yet to see ChatGPT get anywhere near that. 

I’ve dabbled but question the time it takes to write and re-write prompts and drill down to try and get content that is useful – and original. At a basic level, asking it for alternative words or subject lines is a bit like going to thesaurus.com for inspiration. It’s a thought starter at the very least. But any writer mindful of their reputation and longevity in the industry would never try to submit work written in large part or entirely by ChatGPT. 

Have we even scratched the surface on where this tech is going to take us? 

There’s no doubt the technology is advancing, and rapidly, so there’s a lot more to come, and plenty of issues to iron out. Is it plagiarising? Does it need attribution? Is it ethical? We’re already seeing IP lawsuits, calls to pause development and attempts to develop some kind of ethical guardrails. Time permitting, I’m reading different sources on gen AI, from the new breed of prompt engineers to The New York Times, and every week there are new plug-ins, tools and services coming out. It’s certainly unleashed a frenzy of innovation. 

What skills do you think are the most important for freelancers to acquire, especially now?

I’d describe it as both technical and human. Humans want to communicate with other humans where you convey trust, understanding and relatability. I want to believe that the magic of gen AI will never replace these needs. So as a freelancer it’s important to have strong human qualities, which means showing editors and marketing managers you understand their needs, their constraints and their goals. 

Equally, having a grasp of technical skills is important, which might be adding some marketing skills to your repertoire if you do a lot of content writing, UX skills, or strategy and ideation.

Maybe it’s looking to add training, coaching, hosting to your CV so you can take different jobs that don’t rely on just writing. 

It used to be adding social and SEO but these might be the areas that chatGPT will hit hard; so if that’s your area, I’d be looking at ways to do more higher value work and/or see where gen AI can help you help your clients.

Hopefully things that are more sophisticated than something gen AI can produce. 

We may need to demonstrate to clients and editors why we’re a safer bet than gen AI with a new human value prop!

As a freelancer, it’s important to have strong human qualities, which means showing editors and marketing managers you understand their needs, their constraints, and their goals.

Why do you think the Summit is important for freelancers?

Freelancers spend many hours toiling away on their own, often just emerging for coffee catchups every now and the annual Rachel’s List Chrissy shindig. We need opportunities like this to come together, in both an informal way for networking, and for professional development. And that’s what the Summit offers. A fantastic opportunity to gain a whole host of valuable insights, ideas, strategies and learnings about the business of freelancing from a great cross-section of people, plus a good dose of freelance camaraderie.

The conference theme is all about futureproofing your career. What steps are you taking to futureproof your own?

I took Ed Gandia’s strategy course with Austin L. Church last year so I’m offering more strategy services such as thought leadership ideation, content strategy and brand strategy. I’m staying in touch with gen AI, as much as possible, so I know what’s happening and where there may be opportunities to help marketers, for example, utilise it. I’m considering doing more presenting/hosting for client events. I’m also considering doing a marketing course to provide more potential services. 

Do you think the future is exciting for freelancers, and if so, why?

There’s a lot of uncertainty at the moment, and that’s understandable. But having a staff job is no guarantee of safety, as we’ve seen with the large numbers of layoffs; so being freelance is less vulnerable if you’ve got a variety of sources of work. The thing that’s great about freelancing is that you’re able to create the kind of work life that suits, whether that’s taking your skills and turning them into a business, working the hours that suit or deciding on your income goals. 

I think the times suit micro-businesses, but I do think it’s important to approach things with a professional, business mindset. That means defining what you have to offer and its value; managing your time and money; adopting a marketer mindset to develop a pipeline of work and actively; and keeping a lookout on the technological changes and being prepared to adapt. SWOT analysis anyone?

There’s a lot of uncertainty at the moment, and that’s understandable. But having a staff job is no guarantee of safety… so being freelance is less vulnerable if you’ve got a variety of sources of work.

What are you most looking forward to about the Summit?

I’m really keen to hear some of other speakers’ ideas and thoughts on gen AI, of course! There are a few people I know virtually, who I’d like to meet IRL. I’d also like to pick up some intel on other work avenues such as government. Oh, and drinks on the destroyer, of course!


Rosalyn will be a panelist on Day 1 of the Summit. The panel is: How to find work (with your finger in all the pies).


Find out more about Rosalyn Page on her profile page.

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