Setting your freelance rate and chasing up late invoices can be two of the trickiest parts of working for yourself. Money conversations aren’t always easy, especially when creative work is personal and pricing feels... well, a bit made up. Many freelancers undercharge or stay quiet on overdue payments—not because they’re unprofessional, but because they’re human.

These struggles are incredibly common, and you’re definitely not alone in feeling awkward, anxious, or unsure. The good news? There are practical tools and mindset shifts that can make this part of the job feel more manageable.

This question was explored by Regina Stroombergen (Head Creative Tinker at Thinkerbell and founder of MIA – Mums In Ads), who brings broad experience across sectors including auto, healthcare, retail, fashion, FMCG and more. She was joined by Dr Aileen Alegado, a registered clinical psychologist and Director of Mindset Consulting, with over 15 years' experience supporting professionals and business owners. The conversation was hosted by Andy Wright, Founder of Never Not Creative, Co-Chair of Mentally Healthy, and CEO of Streamtime.

Determining your freelance rate

Regina shares several tried-and-tested ways to set your rate:

"Recruiters are really good at knowing sort of what rate you should be asking and then they know obviously what other people are asking for as well so they can sort of slot you in."

She also points to helpful external guides: "Esther Clerehan has a really good guide on freelance rates."

Peer networks are another useful source:
"You could also ask other people who either work with you who are freelancers at abroad in what they earn or friends of yours who might know someone who knows someone," says Regina, noting that,
"Freelancers are more likely to tell you than people who are employed by companies how much they're on."

And when it comes to flexibility:
"Some freelancers also charge hourly or a day rate so you can be flexible for different clients."

The takeaway? There’s no single 'correct' rate. Start with research, stay transparent with your peers, and adapt based on the job, client, or project type.

The psychology behind pricing your work

Dr Aileen dives into the mindset behind undercharging:
"From a psychological perspective, it's checking whether where your level of confidence is as well because I know that a lot of people often would undercharge because they feel like they're asking for too much."

This isn’t about greed—it’s about self-worth.
"Really being a little bit more self-aware about what beliefs you're carrying in terms of your self-worth, self-esteem... that starts to become connected with pricing, business and money."

In short: how we price our work often reflects how we value ourselves. Being aware of that can change everything.

Communicating your rate with confidence

It’s not just what you charge—it’s how you say it. Regina offers this practical advice:
"If you're trying to get your freelance rate right, try and practise it so that when someone asks you, you don't say 'oh, it's 300?' You want to be like '300.' You want to be direct, not that you're questioning your own ability."

She adds:
"Practise saying it without the little question mark on the end and then it always helps."

Andy echoes the sentiment:
"It's a very hard one because often you want a price so that you get the job and so as a result we constantly under quote... but having a bit of confidence in the price is a really good point."

Practise out loud, in front of a mirror or with a friend—whatever works. That calm confidence can make all the difference.

Strategies for chasing payments

Talking about money is tough. Chasing it can be even tougher.
"Invoice chasing is hard. I hate chasing people for money, I know most people do hate chasing people for money," says Regina.

So how do you make it less painful?

• Work with those who respect your time:
  "Ideally you find the agencies that are good at paying and stick with them, and then the ones who you know aren't, maybe if you've had a bad experience, don't go back repeatedly."
• Set expectations early:
  "Make it very clear your payment terms when they hire you, and then know the correct person to chase after that if they're not paying you."
• Be strategic with follow-ups:
  "Don't go straight to the creative director... maybe you need to go to the payment person or the talent person who brought you in."

In other words: be clear, be polite, and be firm. And remember—this is business, not begging.

How NNC Circles can support freelancers

Freelancing can feel isolating. When it’s just you, your laptop, and an unpaid invoice, it’s easy to question whether you’re doing it right. That’s where Never Not Creative’s Circles come in.

NNC Circles are monthly peer support groups made up of 8–10 creatives. The goal? To create a safe, non-judgemental, confidential space where you can share what’s going on and get support—from people who get it.

Whether you’re struggling with self-worth around pricing, or unsure how to word that payment follow-up email, Circles are a place to practise, reflect and learn. You’ll gain confidence, community, and real strategies to tackle challenges like setting fair rates and chasing what you're owed.

You don’t need to do this alone. There are people out there navigating the same awkward conversations—and cheering you on as you find your voice.

‍