Hi Reader,

Recently, my mom went in for what was supposed to be a routine back surgery. The next day, she had a stroke. It was one of the scariest days of my life—advocating for her care, coordinating her transfer to a Neuro ICU, and making critical decisions in a moment of complete overwhelm.

Thankfully, she’s okay and recovering well at home. We were very lucky. But in the chaos, I was so grateful that two years ago, I’d sat down with my parents to have the hard “end-of-life” conversations—talking about what they would want if they were seriously ill, incapacitated, or unable to speak for themselves.

When the unthinkable happened, I didn’t have to guess. I had clarity and could focus on helping her. If this is a conversation you are considering, I highly recommend checking out Five Wishes as a great tool to guide these important discussions.

Have the Conversations Early—Before Things Get Hard

Addressing hard conversations before you actually need to have them allows you to engage the part of your brain that supports clear thinking and problem-solving. Waiting until the situation actually gets hard can trigger your brain’s stress response, making it much more difficult to communicate clearly and get the outcomes you want. Here are some examples of where having the conversation now can save you from bigger issues later:

• Before you hire a friend: Talk about how you’ll handle it if the work (or the relationship) starts to break down.
• Before you start fighting with your co-founder: How will you handle conflict when it inevitably happens? When hard decisions need to be made, who has the final say? (I've got a lot of resources on these convos if you need!)
• Before a big project with your team: Clarify roles, responsibilities, and what success looks like—don’t assume everyone’s on the same page.
• Before you get married: Do a prenup.
• Before starting a new role: Negotiate your exit package upfront.

Hard conversations are uncomfortable—no one loves having them. But avoiding them only makes things worse. The longer you wait, the harder they get.

So—what conversation are you avoiding? Let me know if you get stuck and I'm happy to reconnect and chat.