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#LeadingLadies: Clare Cowperthwaite

When Clare Cowperthwaite’s full time role was made redundant around four years ago, she was faced with a choice: “Do I want a similar role somewhere else – to keep tracking along – or to use this opportunity to look at what really motivates me?”

It wouldn’t be such an inspiring story if Clare didn’t do the latter – she took a leap of faith into the world of freelancing and contracting and hasn’t looked back.

Clare had previously dipped in and out of this type of work, but this time she set a clear goal to put her Public Relations and Change Management expertise to use quite selectively.

“I realised that the actual task I’m doing is less motivating for me than the bigger picture,” she explains.


Clare took time to talk to Agency Iceberg about how she’s built the strength to say no, how she negotiates tough financial or contractual discussions, and how she’s developed a strong client base in the competitive and fast-evolving ‘gig’ economy.


You’re on contract with Asahi, and you’ve done work for NAB and other big names. What benchmarks did you set for the work you take on or turn down?

I look to work with people that are inspiring, and in an organisation that is going somewhere. I’ll ask myself, ‘Is this a learning experience for me?’ I don’t need a particular title like Account Director or Publicist. The beauty of freelancing is that it enables me to make those choices.

I’ve always been interested in helping with the ‘disconnect’ – organisations are doing a great job crafting these polished external messages about what is happening. But often, that isn’t exactly what the employees are experiencing internally. I’m interested in how brands can drive [internal] culture to match their external brands.


Some freelancers never have the confidence to decline work, even if it’s a sub-standard offer. There’s a fear they won’t get asked again. How have you grown the guts to say no?

You need a thick skin and confidence. When you’re starting out it’s a difficult thing to do. You can get into a headspace where you think, ‘Gosh, I’m lucky that anyone wants me to do anything. I am competing with so many people with great experience.’ But there’s always going to be someone else in the mix and you need to accept that. You need to be more confident in your ability than ever before.


Have you always been that assured?

It’s easy to say this 20 years down the track when you have experience!


You’ve had full time offers after finishing contracts, but you’ve stuck to your independent approach. Why haven’t you been lured into the fold?

I always ask myself the question, ‘Why would I want to be a permanent employee?’ Not in a negative way – but I’ve looked at organisations and considered what my next role would be, or who I would emulate in the company, or if there’s a challenge [past the contract] that I could be the right person to solve it. It’s not that the organisation isn’t amazing, but I couldn’t see it for myself.

Clare Cowperthwaite Leading Lady 2 1

Negotiating money can feel awkward. How do you say, ‘this is my value’ and still win the jobs?

Freelancers have the luxury of not having agency overheads, and we can be agile and responsive, so generally speaking there’s a financial advantage for someone wanting to hire you. So don’t feel like they’re doing you a favour, it’s a two-way exchange. Set a price and stick to it. Do your sums and work out what you need to live and to get ahead.


I recommend building up multiple income streams – read The Barefoot Investor and get some financial advice. Don’t just walk out and think things will fall at your feet and you’ll make a million. If you charge $100 an hour, there are only so many hours you can work in a day. If you want to do more, you get into the realm of sub-contracting and small business.


Building a client base takes time and work, and you have a solid line up. So what’s been your trick?

Networking. Consciously keep my contacts warm. But old school networking – going to functions to meet people – it drives me nuts, I hate it! You don’t need to do that, but you need to consciously keep your contacts warm. A good way is through social media – but I confess that it [social media] is something I need to do better. But you have to think about how you’re going to position yourself online – don’t just ‘like’ Richard Branson’s quotes!


How do you go about integrating into new workplaces or new teams?

It can be tiring and quite disruptive going into new businesses, as you are constantly having to understand their business. Even socially, it can be about finding someone to have lunch with if you go into the office, which I tend to do. It can be very challenging and you need to build some strategies to shortcut that learning curve.


I have seen freelancers and contractors that remove themselves so much [from the environment] that the task and what they contribute is extremely narrow. If you are contracting – try not to remove yourself from the social aspect of the business – that’s how you learn a lot about the business, make friends and contacts that can help you later on.


You spend so much time helping others craft their brand image and culture, but what about your own?

I think about what I’m working towards in terms of my professional reputation. If there’s a thing you want to specialise in, you have to be quite deliberate in the choices you make. I think about what makes me special – it could be as simple as responsiveness. Or that I can spend a little extra time learning about a business because I’m not bound to time sheets.


The ‘gig economy’ is taking off thanks to technology and the changing way companies are hiring. Many people are shifting into freelance. Do you feel like a bit of a pioneer?

Yes, it’s the way the economy is going. In future, we’ll have a two-speed economy – the mass companies and individuals, and very little in the middle, making more opportunities for freelancers and contractors to fill the gaps on the services they need.

Clare Cowperthwaite Leading Lady 3

So where’s the freelance work of the future?

Content creation will continue to be important. It will be more about understanding the customer journey. How do we help people have a connected experience with a brand or an organisation?


Has having your two children Will and Sophie influenced any of your work decisions?

It was easier having a permanent job when I was having kids. It wasn’t the maternity leave and entitlements, but with your first child it’s such a tough thing to go back to work, so it helped to go back to a business that I knew.


Forgive the cliché, but what are your aspirations for your work?

This may make me sound less ambitious, but truthfully, I just want to keep doing work that makes me happy. I chose freelance because I never really saw myself as the CEO or the Chairperson of a Board. But that didn’t mean that I didn’t want to do good work, or be known for good work.


I also need to balance work with family – and I say that with caution – as I don’t want people to think that I believe family is the only reason to choose a flexible arrangement. Everybody has different stuff going on in their lives, and our ability to be our whole selves when we’re working makes us better at what we do.


Get in touch with Clare on LinkedIn here.


Photography by Breeana Dunbar.