Episode 16 of The Reluctant Optimist: You sell like you buy.

For a long time, I thought looking for the best deal made me smart, but eventually I realized that same instinct was quietly shaping the way I sold. If you are always hunting for the lowest price as a buyer, it is easy to start assuming your customers think the same way—and then you price your work like you are protecting them from value they may have been willing to pay for. In this episode, I talk about how my own buying psychology trained me to underprice, overthink proposals, and unconsciously sell to the cheapest version of myself instead of the right customer. The truth is that cheap customers are often the most expensive customers because they bring more friction, more doubt, more negotiation, and less trust. Pricing is not just about money; it is positioning, belief, identity, and the first story your customer hears about what your work is worth. If you are an entrepreneur, this one is about asking whether your prices reflect the value you create—or the limitations you have not outgrown yet.