Today Shutterfly accidentally sent a highly targeted email out to a (much) larger group than intended. “Congratulations,” it said, “There’s nothing more amazing than bringing a new life into the world.” I chuckled at the message because of the irony. My own “new arrivals” are now 8 and 10. Being played out today on social media, the happy Shutterfly message could be ironic, painful, funny or insensitive, depending on the personal circumstances of the recipient. Moms dealing with infertility, babies in NICU, single moms, estranged dads. As a sympathetic marketing person whose at least once in their career hit the ”SEND” button too soon, I felt bad for the unintentional damage it did. OK, so let’s pretend Shutterfly had sent this email to the right group instead of the wrong group of people. Does that make the message smart? I’d say not. Regardless of today’s technology in data mining, traffic stats, and cookies, we still cannot over-assume. We run the danger of projecting our own definition of how life should be, a dangerous slippery slope. “Now’s the time to send out thank you notes,” with a “tip” that thank you notes are better late than never. Excuse me? Startups, VCs and marketers aggressively look for the “pain points” as market opportunities but rarely are these REAL human pain points. As entrepreneurs and marketers, it’s better not to “go there.” Let the customer go there, and you can help them out, good times and bad. People don’t need to be told what’s important in their lives. They already know.