Spoiler alert: This article is about building confidence and grit – the discount is a bonus! ;)
Here's a fun challenge for you to try out next week: Every time you go for a coffee (or sandwich, or lunch) this week, ask for 10% off.
Whether or not you get it doesn't matter (though I'll tell you how often it works). This "comfort challenge" is all about building your confidence and overcoming your fear of rejection, by forcing yourself into a slightly uncomfortable situation.
There's actually very little downside to it. Worst case, you'll get told no. So what? It's like being told a coffee isn't available, it's not a big deal. You just move on with your life. The upside is pretty good, though. If you do it for a week, it will really help build your confidence and you will learn how to act in uncomfortable situations.
The way I see it – you will definitely have uncomfortably situations in the future. Maybe someone calls you out on something in a work meeting, or you get caught up in a fight, or you get told that your flight is fully booked and you need to wait for another one. Why not practice for those situations now?
In a way, it's a bit like practicing for an exam or an interview. One rule though: Since it's not about getting the discount, you can't say it's an experiment. You must own up to the request when you make it.
If you get in the habit of doing so, you'll naturally learn how to carry yourself more confidently – and I think that's a skill worth learning in just a week!
By the way, I heard about this challenge from Tim Ferriss (author of the 4 hour work week). Do check out his stuff if you found it interesting.
As promised, I'll tell you about my experience when I tried it out last week: I got a discount ~50% of the time. I'd say that's pretty good!
Do try it out this week, and reply back / email me to let me know how it went. And most importantly: if it got easier every time you asked for me!