Admittedly, estate planning is not an easy topic to bring up with parents and other family members, but dealing with the topic when there are no looming health issues is definitely easier than discussing estate and disability planning after a diagnosis or accident. You’d probably assume that the parents of a middle aged estate planner would have their affairs in order, with all of the big issues ironed out and documented, but in my case you’d be wrong. Last summer my mother was diagnosed with stage 4 small cell lung cancer. When the doctor met with our family to discuss diagnosis and treatment, she gave us a time horizon that seemed unimaginably short and then asked whether my mom had her estate planning documents done. It was under those circumstances that I started walking my mother through the issues I had discussed with countless clients and I desperately wished I could turn back time and nudge her to think about the tough issues before learning that she was ill. My mother had draft documents, but had been sitting on them for a year, unable to make decisions and unwilling to discuss the uncomfortable issues. Nobody wants to ponder their incapacity, physical and mental decline, and mortality. But I can attest to the fact that those uncomfortable issues felt much more daunting when faced with a terminal illness. Starting these discussions while everyone is happy and healthy can be helpful and lessen the stress of planning during an already difficult time. There’s no time like the present to engage your family members in dialogue. A recent Washington Post article discusses the importance of this topic. Additionally, it is important to work with professionals who are deeply experienced and knowledgeable in estate planning and can help you and your family navigate hard issues and think through alternatives.