In an article from HN, I came across the following advice: Always tell your customer/user "yes", even if you're not sure. 90% of the time, you'll find a way to do it. 10% of the time, you'll go back and apologize. Small price to pay for major personal growth But I've always thought that one should do a feasibility analysis before making any kind of promises to a customer/user, so that they aren't misled at any point. At what circumstances, then, should the above advice applicable?