Where do you start a conversation like this? “Hey honey. How was work? How much money do you think the kids will need in case we’re murdered in our sleep, while the kids are sleeping?” What’s the best way to start about something like this? The best way is the most sensible way; just be frank. “We need life insurance . We have a complicated estate, and in order to make sure things happen the way they should, after our unfortunate demise, we should have wills, we should have trusts and executors of those trusts, and we should have life insurance policies taken out.” That makes a good deal of sense. And of course, your accountant might have a say in this. Your estate planner might have a say in this. These are the sort of folks that you should feel comfortable talking with, like a physician or a lawyer, comfortable enough to bring up the most unpleasant things.