The Talk You’re Avoiding: Why Planning for Your Parents’ Future Starts Now

The Hidden Entrepreneur Show with Josh Cary

You’ve heard of the talk about the birds and the bees, but are you prepared for the other talk? The one you need to have with your aging parents about their future care, finances, and final wishes?

In this emotional and eye-opening episode, author and former EMT Will Holditch joins Josh Cary to reveal the conversation that every Gen Xer and younger Baby Boomer must have with their loved ones. With stories pulled from real-life emergencies, personal loss, and the chaos that comes from being unprepared, Will lays out exactly how to get your family on the same page before it’s too late.

Whether you’re in your 40s or 60s, this episode is a wake-up call. You’ll walk away with practical steps, life-saving context, and the motivation to finally take action.

What You’ll Learn in This Episode

The Conversation You Can’t Afford to Avoid

Discover why it's time to sit your parents down and start documenting their wishes, medical details, and key information before a crisis makes that impossible.

Why Most Families Are Totally Unprepared

Learn from real stories of emergency room chaos, missed benefits, and heartbreaking confusion, all because no one had the right information when it mattered most.

Inside the 168-Page Workbook

Will shares why he created Strategic Planning for the Golden Years, a practical, fill-in-the-blank workbook that breaks the process into manageable steps to help you and your family plan proactively.

The 3 Pillars of End-of-Life Preparedness

Get a clear breakdown of what you need to know: personal information, medical history, and financial details, plus the overlooked category that could create massive complications: digital access.

Handling Resistant Parents with Grace

Worried your parents won’t cooperate? Will explains how he got his own reluctant father to fill out the workbook without pressure or conflict.

What Doctors, Nurses, and Case Managers Need From You

You’ll be shocked to learn how much lifestyle info (like what snacks your parent enjoys) matters when placing someone in the right care facility.

The Role of Siblings and Family Dynamics

This isn’t a solo mission; learn how to divide the responsibility among siblings and extended family so you’re not carrying the burden alone.

What Happens When You Wait Too Long

From misplaced DNRs to lost VA records, Will shares examples of what happens when planning is postponed and how to avoid the emotional and financial fallout.

Memorable Quotes

“You’re 54 now. It’s time to sit your parents down and have the talk. Because one day, you’ll be the one advocating for them.” – Will Holditch

“There’s legal power of attorney and medical power of attorney, but there’s no such thing as digital power of attorney. You need the passwords.” – Will Holditch

“This isn’t about taking over their life. It’s about making sure they get the care they earned and deserve.” – Will Holditch

“If you’re waiting for the crisis to get prepared, you’re already too late.”