Three conversations every man over 40 should have had by now. Most haven't. Here's how to start.

The conversation with your wife about what happens if you die

About 60% of married men over 40 have not had a substantive conversation with their spouse about the financial consequences of their death. Where the life insurance documents are. Where the will is. Who the financial advisor is. What the passwords are.

The version of this conversation that fails goes like this: "We should probably talk about what happens if I die." The version that works goes like this: "I want to spend an hour this weekend walking you through where everything is, in case anything ever happens to me. Can we do that Saturday morning?"

The first version is a topic. The second is an appointment. Topics get postponed. Appointments get kept.

The conversation with your aging parents about their estate

This one is harder. Most men avoid it because it forces a conversation about mortality with the people whose mortality they don't want to think about.

The frame that works: "I want to make sure when something happens, I can take care of it without making things harder for you. Can we sit down and you walk me through what's where?" Not what they have. Where it is. The information you'll need at the worst moment of your life is the information they'll be unable to give you when that moment arrives.

The men who have this conversation in advance lose a parent and grieve. The men who don't lose a parent and discover, in the middle of grief, that they have to figure out a fifty-year financial puzzle in two weeks.

The conversation with your business partner about the worst case

If you're in business with anyone — partner, co-founder, family member — the conversation about what happens if one of you dies, gets divorced, or wants out is the conversation you should have had before you started. If you didn't have it then, have it now.

Buy-sell agreements. Key man insurance. Operating agreements with dispute clauses. None of this is fun. All of it protects you when the relationship breaks, which it will, in some form, eventually.

The pattern

The conversations men avoid are the conversations that protect the people they love most. The cost of having them is one uncomfortable hour. The cost of not having them is sometimes everything.

Schedule one. Have it. The next two get easier.