Is the fear of rejection stopping you from negotiating?
There is no doubt that practice helps to build confidence when developing a skill. Negotiation is no difference. Every day encounters offer us opportunities to practice our negotiation skills ahead of that super critical pay rise negotiation with your boss. Spotting opportunities to negotiate can depend on your culture and personal experience.
The most obvious opportunity is when you are shopping. In Australian and New Zealand culture we are trained to see prices as 'fixed' and generally not open to bargaining. However, we also know that pricing can be flexible, just think of the multitude of sales that come up across any given year. So asking the question, "That's an attractive item but it doesn't fit my budget, can you do better on the price?" can be a way of practicing that moment when you assert what you want. My hot tip is to really give this a go when you next visit a grocery or farmers market, where you are more often dealing with items that don't have individual prices. Especially if you are paying cash!
A further opportunity is around purchasing items in the days immediately before or after a sale. Asking sales people something like "Excuse me, would it be crazy to think that you can give me the 30% discount today? I'm heading out of town tomorrow and I won't be able to take advantage of your offer". This is definitely a wasted moment, if you are getting the part-time shop assistant, you will need to find the person who has a little authority. However it's a great way to get that moment when it feels like you are being outrageously cheeky, but that is what it feels like when you are practicing and building your confidence to negotiate. And who knows? You might come away with a discount!