Yesterday I watched a friend who was struggling with homelessness unpack her few belongings. Inside her purse was a large, rather expensive, luxury-brand chocolate bar. She held it up and twiddled it back and forth in her hands, letting the silver foil catch the light. “Sweetie, I’m homeless,” she said, very matter-of-fact. “You’d better believe I’m getting the good stuff.” And boy was she making a great point.
I’m a little wary of asking for discounts, especially from very small companies. When it’s just one or two people running the show, it means those one or two people spend an inordinate percentage of their time doing things they don’t like to do. Nobody starts their own business because they love filing quarterly taxes—they soldier through it for the 10% of the time where they’re actually doing the thing they love.
And every small business owner I’ve known has lost sleep over their pricing. No matter what you’re selling, there’s local and global competition for it, and consumers have tools now that didn’t exist 10 or 20 years ago that allow them to find, compare, rate, and review similar services. The world is a buyer’s market, and it’s really hard to measure what you know your work is worth against what you know people are willing to pay for it. Asking to pay less for the same product is almost always a wearying and unwelcome question… with one very special exception.