This topic challenges all of us. You have run a P&L. You have negotiated contracts. You have made calls under pressure with real consequences. And you have not asked your mother what happens to her money. Christopher Lochhead ran an episode on this that I think belongs in this room. Episode 453, Follow Your Different, built on a Category Pirates piece. The setup is simple and it will make you uncomfortable, which is why I am posting it. One of the pirates gave his mom financial advice years ago. She ignored it. He did not follow up. He recently checked back in and found she had put large chunks of her money into annuities. He made her cry trying to fix it. His words on what went wrong: he was so smart he was stupid. He put being right ahead of the relationship. That is the whole trap in one sentence. Most of us in this group are competent enough to be dangerous here. We can read the documents. We can spot the fee structure. And that competence is exactly what makes the conversation go sideways, because we walk in like a consultant and our parents hear an audit. They get defensive. They stop telling us things. And then the decisions get made without us, usually by someone who sells for a living. The move is to lead with what they want, not what they own. What do the next ten years look like. What do they want left behind and for whom. What are they afraid of. You get the numbers eventually, but you get them because they invited you in, not because you demanded a spreadsheet. Two more things worth naming. Keep your siblings in the room. Secret arrangements are how families come apart after the funeral. And there is real money on the other side of the table working to get to your parents first. This is the relationships pillar and nobody wants to touch it. It is inconvenient, it has no clean win, and it does not fit in a calendar block. Listen here: https://lochhead.com/fyd-how-to-talk-to-your-parents-about-money-2026/