Much like Jill has trained me to unload the dishwasher every morning, I have trained my very favorite, first wife to expect concrete answers to the following questions. When we discuss our financial future, this is what we talk about. Can you answer these questions about your financial future? How much income we need and expect: Do you have a retirement income projection showing the total amount of income you can expect to receive every year throughout your entire retirement, broken down into each individual income source? Does your retirement income analysis show when each income source starts, stops, increases, and decreases? How much tax we will pay: Do you have an income tax analysis showing how much income tax you will pay as you take income from your assets? You may believe that taxes are going higher in the future; have you accounted for that? How much money we will likely leave behind: Do you know how much money you can reasonably expect to leave to your beneficiaries after you’ve used your assets for income for your entire life? What steps we will take to make our plans work out: Do you have a written summary of your entire plan that includes the status of your current financial position, what you’re trying to achieve, and the step-by-step process of what’s required for success? How much market exposure we want / have? Do you have an understanding of how much market exposure you have and what would happen if the market lost a ton of value?