Real talk: how to make easy work of hard conversations

Life is full of difficult conversations, but few are harder to initiate than the one about what will happen to your assets, and perhaps even your children, when you are no longer here or able to take care of them. Facing our own mortality is overwhelming enough without the stress of making crucial financial decisions that will have implications long after you are gone. But getting your affairs in order is one of the most important things you can do for your loved ones, says Shelly Eweka, a Senior Director, Financial Planning Strategy at TIAA. "People think, oh, I don't have anything, or this person will just take care of it, but that's just wrong. Your spouse or children could be dealing with your death or incapacitation, and on top of that, now they're trying to gain access to your accounts or find out whether you had a life insurance policy," she says.

Talking to your spouse

While it's worthwhile to hire an estate attorney to draw up a living will, power of attorney, a healthcare directive, and a will that includes instructions for guardianship of your minor children, the first step is to talk to your spouse or partner about what their thoughts are on all of these topics. "If you're hesitant to start the conversation, it helps to remember that your spouse or partner doesn't really want to talk about this either," says Patricia Saul, Ph.D., a psychotherapist in Wyckoff, New Jersey. "There's a natural desire to avoid this topic at all costs, and that needs to be respected."

With that in mind, Saul recommends setting aside a stress-free time (maybe on a Sunday morning after you've both had coffee) where you'll discuss heavy subjects like who will be the executor of your will, or what your wishes would be if you were to become incapacitated. Keep the conversation to no more than an hour, and if things get sticky, table the discussion and schedule another time to talk. "The most important thing is to preserve your relationship, and sometimes that means backing off," Saul says.

However, if after several attempts you still can't come to an agreement on serious questions (such as who's the best guardian for your children) Saul suggests asking a trusted mutual friend or family member to sit in on your next roundtable and observe, after which they can give you input on where you might be at an impasse. It's also helpful to think about how your decisions will affect those you are leaving behind, like if you have adult children, and you need to select one of them to be your executor. "Ask yourself, 'If I'm not here, and I want my kids to still talk to each other, which kid can I pick where that will be the case?'" says Saul.

Talking to your parents

Once you've made headway on your own affairs, it's natural to want to know if your parents have done the same. Healthcare decisions are often a good starting point, says Saul, especially if they've recently overcome a bout with a non-life threatening illness. "Use this as your 'in' and ask your parents, 'If you get sick, what would you like me to do? How can I help support you?'" she says.

Whatever they end up deciding regarding both their health and their finances, make sure it's written down in a legal document (again, that's where an estate planner can help) so that everyone is on the same page. "One of the biggest mistakes people make is implementation," says Mark Schrader, a Financial Planning Strategist at TIAA. "They make the plans but don't line up the beneficiaries. All of your documents have to line up."

And finally, focus on the positive: There's a tremendous amount of relief that comes with getting your affairs in order. "Family members feel better, you feel better. There's a real palpable satisfaction knowing that if the power goes out, things will still keep running," says Daniel Ruppel, another Financial Planning Strategist at TIAA. "It's like having a backup generator."