Maddy Roche: Hello everyone, welcome to Childfree Life by Design. Today we are talking about a real lived experience of a financial advisor who helped his Childfree client navigate end-of-life decisions. I’m Maddy Roche, and in this episode we’re covering what Childfree people need to do to prepare for an emergency or end of life, the team they need around them, and how to prepare themselves for the decisions they may have to make as they age.
If you’ve ever wondered what end-of-life decisions look like, this conversation will give you clarity and tools to make intentional decisions to support the life that you want.
Intro: From Childfree Insights, this is Child-Free Life By Design, the go-to resource for building the child-free life you want. Every episode gives you practical guidance, clear direction, and meaningful conversations to help you live intentionally and design a future on your terms. This podcast is for educational and entertainment purposes only. Please consult your advisor before implementing any ideas heard on this podcast.
Maddy Roche: Hello, Chris Dale.
Chris Dale, CFP®, CeFT®: Hi Maddy.
Maddy Roche: Listeners, Chris Dale and I go back nearly a decade. I have known Chris as he started his firm as a financial advisor, and today we have him on the podcast to share real lived experience of helping his client who is Childfree navigate end-of-life decisions. I think this is such a vital conversation for all of us because it’s going to bring us into a space that may make us feel a little uncomfortable as we think about what it may be like to age and what it’s like to build a team around us that may support us. Chris has got such sage wisdom on all of this.
So, Chris, if you wouldn’t mind just introducing yourself and your firm a little bit, and then we can get into the meat of the conversation.
Chris Dale, CFP®, CeFT®: Sure. Sage wisdom? I don’t know that that necessarily describes me; I learn a lot by fire. My name is Chris Dale, and the name of my firm is Life After Grief Financial Planning. My firm is geared towards people like me, about 17 or 18 years ago, and it started on the heels of me experiencing a tremendous amount of grief in a short period of time and having no advisor—financial or legal—to be able to help me out. So what I did is I created that space for other people like me, and I exclusively help clients that have experienced grief. I also teach other advisors to do what I do.
Maddy Roche: Incredible. Chris, you’re so perfect for this podcast in a number of ways. What was some of the training you alluded to around how to be able to support people through grief?
Chris Dale, CFP®, CeFT®: Frankly, a lot of the training that I had before I realized that there was training was hospice training. I’ve been a hospice volunteer for about 10 years. That gives me specialized training understanding what happens to a person when they are declining in health to the point that their body is going to stop functioning. In addition to that, I’m a certified financial transitionist. This allows me to be an expert helping folks with the transitions that come along with money. My expertise is well beyond just the Xs and Os working with money; it’s really the emotional component and being their advocate and quarterback.
Maddy Roche: How do you work specifically when you have someone that maybe doesn’t have traditional next of kin? I imagine you become even more crucial to those clients.
Chris Dale, CFP®, CeFT®: One of my biggest fears, quite frankly, are clients that have no next of kin because I know they rely so heavily on me. I had a client I nicknamed “Mr. Hugh Brees” whom I had known for 20-plus years. I started seeing signs of decline when he was in his eighties. He didn’t have estate planning, and part of my fiduciary responsibility is to recommend it. He initially told me he didn’t care where his assets went because he had no next of kin. My “in” was explaining that if he reached a point where he couldn’t advocate for himself, I wouldn’t even be able to give him his own money without a third party involved.
Maddy Roche: Chris, you’ve just alluded to a number of things that could come before someone passes away that would warrant having a team around them. Could you paint a picture of a couple of things a person may need?
Chris Dale, CFP®, CeFT®: In late 2024, I searched for a fiduciary who could honor his wishes, act as power of attorney, and handle healthcare directives. That person is not me—it’s a conflict of interest. I found an attorney whose firm provided these services. My client signed his estate planning paperwork in November 2024. In January 2025, he had a major car accident. Because the paperwork was in place, the attorney could immediately step in as medical power of attorney and make decisions for him while he was in the hospital.
Maddy Roche: Those are decisions like whether he wants to be kept alive with artificial support or his specific medical history.
Chris Dale, CFP®, CeFT®: Exactly. While he was recovering at home later that January, I noticed he was short of breath and called an ambulance. They found out he had cancer. At that point, we had to find a rehab facility. It was a team effort between myself, the attorney, and a close personal friend. I realized we couldn’t be there every day, so I vetted and hired a companion service within 12 hours. This gave us checks and balances. A week before he died, the companion reported his breathing had slowed and he wasn’t eating. I knew he had about a week to live. Because we had the team in place, we were able to uphold his dignity and ensure he was the captain of the ship until the end. I wish Childfree Trust® had been online then because I could have pointed him to a dedicated team specifically for this.
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Maddy Roche: Chris, thank you for sharing that story. If he didn’t have those papers signed, how would life have looked for Hugh Brees?
Chris Dale, CFP®, CeFT®: It would’ve looked dramatically different. He would not have been able to get into a good rehab facility as easily, and I wouldn’t have been as free to make recommendations in his best interest. His end of life would not have looked as good as it did. He was very thankful and vocalized that he had the best care.
Maddy Roche: It sounds like you were an advocate who could address things like large insurance claims. How do you have this conversation with people around emergency planning before it’s too late?
Chris Dale, CFP®, CeFT®: I share real-life examples. In Hugh Brees’ case, I had a “ticking clock” feeling. He survived a miraculous car accident but was happy he took my advice. In Florida, we have specific training regarding seniors being taken advantage of, so I had the attorney act as a third-party set of eyes to protect both the client and my firm as our relationship shifted from typical financial advising to managing his quality of life.
Maddy Roche: What’s your advice for proactive planning for aging?
Chris Dale, CFP®, CeFT®: Delegate as much to a professional as possible. When things go bad quickly, that is not the time to do planning. You want to do all of this before heated emotions or major medical events take place. I would rather dictate my own wishes than leave it to the state or an unprepared individual.
Maddy Roche: How did you manage the accumulating costs of his care?
Chris Dale, CFP®, CeFT®: After his 10-day hospital stay, he received a bill for roughly $130,000. Because he had allowed the hospital to give me information, I was able to talk to them and point out that his actual out-of-pocket expense should be less than $2,000. Thirty days later, he got a right-sized bill for $1,100. He said, “I guess you earned your keep.” My services on an hourly basis were an allocation of funds that got him what he needed at the highest level, but Childfree Trust® would have been a natural layup at a much lower cost if it had been available.
Maddy Roche: Chris, I want to summarize this in three points: how important it is to have a team listed in your documents, not making a plan during an emergency, and having advocates who can act for you when you can’t. We end the podcast with a segment called Deliberate Detail. What’s something intentional you do to design an amazing life?
Chris Dale, CFP®, CeFT®: My faith. It leads to a lot of support I’ve had in my life.
Maddy Roche: Beautiful. Chris, you’re also about to be a published author. Tell the audience how to find you and about your book.
Chris Dale, CFP®, CeFT®: You can find me at lifeaftergreeffp.com. My book is called Life After Grief: Holding the Numbers with Shaking Hands. It covers the tragedy, grief, and trauma I’ve experienced and the unique gift I’ve been given to help people through life and even into death.
Maddy Roche: Chris, thank you so much for this podcast. That’s all for this episode. Remember, intentionally choosing to invest in moments of joy is just as important as investing in your future. Until next time, happy designing.
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