One thing I’ve learned in my life as a freelancer and writer is always to ask for more. It’s tough – my cultural background views taking any obvious interest in money as vulgar, and asking for things as rude. But I’ve overcome the internalised messages I learned as a child and now, although I still feel a twinge of awkwardness, I always push through it and ask, ask, ask.

Early on in my writing career, when I received a contract from a publisher I was so thrilled to be published I signed it, no matter what. But I’ve had some bad experiences, and ended up once owing a publisher money because the contract stipulated I had to pay for artworks. As it was an illustrated book this turned out as pricey. So pricey that six years later, after abysmal sales, I had still not earned a cent. Everyone was paid, the printer, editor, proofreader, book designer, artist – even the tea lady had been paid their salary. But I hadn’t earned a cent for a book they asked me to write.

It taught me to be more hardnosed about my intellectual property, and to take the contract as presented to me as the opening offer. I negotiate on everything – they’ll give you three free copies of the book – I’d like five. They’re offering x percentage royalty. I’d like x plus 1. More often than not they give you what you ask for, or somewhere in the middle. It’s rare that you get a flat out ‘no.’

It’s amazing what people will give if you just ask. And not just when it comes to contracts.

Often you just need to phone up the company and ask for a discount. My security company had become very expensive. A rival company was cheaper. So I rang my company to cancel the contract and discovered I was paying extra for a feature I will never use. They gave me a new quote and I was able to drop the annual costs by R1500.

We’re selling our house. The compliance quotes were ridiculously high. R240 to tighten a tap? R1200 to put a gas cylinder on a level paver, replace a length of pipe and put up two signs? Don’t make me laugh. I managed to get them to drop their quotes by over R1000.

The secret is to be non-emotional and polite. Rushing in and saying, ‘What a rip-off, you’re crazy if you think I’m paying that,’ is not going to work. The calmer, ‘I noticed that Builder’s Warehouse is selling this for a third of the price. Could you meet their price please?’ is much likelier to get you the result.

You can often get good prices when business is slow. We bought a keyboard at a music shop in January. The shop was empty – nobody had money to spend on instruments. I’d noticed that takealot had the same keyboard on special at nearly half price, and I mentioned it in passing. The salesman was eager to make a sale, and offered to match the takealot price. We had the benefit of trying it out and getting his expert advice as well as the lower price, and he made a much-needed sale.

When it’s a big sum you’re spending, the chances of a discount are higher. I always push for a discount when my husband or I are buying a car. If they can’t discount the asking price they may give a higher price on the trade in. I’ve always got what I asked for and the salesmen seem to expect it.

I’m hyper vigilant at supermarkets. Woolworths often mislabel their food products, or the till price doesn’t reflect the current discount. If you go on a Monday when the changeover happens between one week’s discounts and the next, you often find the shelf price and the till price differ. They are great about giving you one of the products for free.

And then there’s good old-fashioned chutzpah. I buy gifts often from an online kitchen equipment company. Once I sent them an email: I’m a little bit sad today. Please, can I have a present?

They sent me some quirky fridge magnets and a box of delicious biscuits with a handwritten card saying ‘I hope this turns your frown upside down.’ It’s a clever move on their part because I told everyone how generous they are, and they gained more than their R100 worth of free advertising.

When my husband died I was left with a huge bond and very little money, and the private bankers called me in and explained that I’d have to return to ordinary pleb banking, and stand in a queue like everyone else. The poor guy who broke the news looked so miserable to be kicking a new widow out that I decided to milk his misery and to ask him for a present.

‘Wait here,’ he said. He disappeared upstairs and came back with a very nice set of designer salt and pepper cruets, which apparently is the welcome gift they usually give the wealthy when they join private banking. For a moment, I felt bad taking them, but the twinge of conscience didn’t last long. Plus it made him feel better about kicking me out so we all won.

Sometimes people get annoyed if you ask for a discount. Factory shops are usually pretty rigid about saying no, and you can get slapped down sharply.

There are some people I would never ask for a discount – like small mom and pop companies who are presenting good products at a fair price – I like supporting them, and their profit margins are usually low.

Another group is self-employed creatives – I almost always pay full price because I believe their work is a valuable contribution to society and it’s usually very labour intensive. It’s tough having to generate creative energy every day to produce something of value, and it’s even tougher putting it out there and hoping someone will buy it. 95% of writers, crafters and artists will never earn anything that reflects the amount of hours they put into a work. They often will give a discount because they’re desperate for a sale, but I feel mean asking, so I don’t.

It’s horrible to ask for a discount at a charity shop or fete, unless something is accidentally overpriced. In fact, when things are under priced at charity shops I sometimes offer to pay more. I once found an Ashford spinning wheel in perfect condition at a charity shop for R90. I bought it, but paid them R300 for it, which was still a bargain.

But big conglomerates and even many smaller companies seem to have a built-in marketing/promotions budget and if they can’t give you money off may throw in a free gift. As the saying goes, ‘there’s no harm in asking.’ You may just get lucky.