This week we discuss legacy letters, which are personal letters written to loved ones to express values, life lessons, regrets, and love, beyond financial matters. Legacy letters allow individuals to leave behind something deeply meaningful—sharing wisdom, advice, and affirmations, rather than just focusing on money or material assets.
The idea was inspired by a podcast featuring Blake Brewer, who shared his personal story of receiving a legacy letter from his father after his unexpected death. This letter expressed pride, love, and guidance, and became a pivotal moment for Blake. Since then, Blake has made it his mission to encourage parents to write legacy letters to their children.
The basic structure of the legacy letter includes the following:
Introduction: Explaining why the letter is being written.
Apologies or Regrets: Acknowledging any unresolved feelings.
Affirmations: Expressing love and belief in the recipient.
Memories: Sharing meaningful moments.
Life Advice: Offering guidance for the future.
The letter doesn’t need to be perfect—what matters is that it’s written and shared.
Legacy letters can offer emotional comfort, especially during times of grief. Additionally, while legacy letters can be part of estate planning, they also serve as a tool for broader life planning, helping people express what truly matters in their lives.
Don't wait until it's too late, get started on your legacy letter today!
Resources:
-How to write a legacy letter: https://www.legacyletter.com/
- Alliance of Comprehensive Planners: https://www.acplanners.org
- John's firm website: https://www.trinfin.com
-Find us on Facebook: www.facebook.com/friendstalkfinancialplanning
TRANSCRIPT:
Bridget: Hey John, I know that recently you did some work with clients about communicating more than just their wills, really about how they reflected on their life and what they wanted their legacy to be. And these are called legacy letters. Today on Friends Talk Financial Planning, we're going to talk about legacy letters and why you should consider them and what you should include. Hi, I'm Bridget Sullivan Mermel. I’ve got fee-only financial planning practice in Chicago, Illinois.
John: And I'm John Scherer. I've got a fee-only financial planning practice in Middleton, Wisconsin. And before we start talking about how to leave behind your legacy, I want to remind everybody to hit that subscribe button. It helps other people find our information on YouTube and helps spread the good work that we're doing here. So with that, let's jump in. And I'll be happy to share about what our experience was.
And one of the cool things I think, Bridget, about this, and you mentioned in the introduction, is with comprehensive financial planning we look at all aspects of a client's financial life, not just investment sort of thing. It’s not all aspects but it's a wide range of things. Estate state planning is one of those things. We're not attorneys, and neither is anybody in your office. We won't write wills, but we help talk to people about what do you want your legacy to be.
And often it's about the money side and how do we manage the taxes and who gets what and those sorts of things, which are all super important. But then we also talk about what is it that you want to leave behind? And it's not money necessarily for everyone. It's some of these other deeper meaning things, these values, and that's what this is all about.
Bridget: Yeah. Well, I find it so interesting because like you said it's not just about money. It’s not just about the dollars, it's also about what it represents. And if you're reviewing your life, it's not just about how much did I make. It's also about what were my values, what was my motivation, what am I proud of, and what do I regret? So why don't you get into the process and talk about how you got people thinking about this.
John: Yeah. So I'll just give you some of the background. I was listening to a podcast, and there was a gentleman named Blake Brewer. And we can put a link to his website in the in the show notes. But he was talking about how he sort of invented what he calls the Legacy Letter Challenge. And he's got a great video on his website, but in Reader's Digest version, he was a young adult, and his family took a vacation to Hawaii. He went snorkeling with his dad, and his dad ended up getting caught in an undercurrent and dying on this trip—shocking, terrible thing.
And back in the condo after trying to process all this stuff, his mom had found in his dad's luggage a letter he had written to Blake. And it basically was a legacy letter without knowing it at the time. It said things like, hey, here are things that are really important to me, and you're special to me, and here's what I'm proud about, and here's what I hope for your future. And for Blake, it was literally the last words from his dad. And so, he’s made this a mission in his life. His goal is to have a million parents write a legacy letter to their kids.
When I heard this, I thought, man, that sounds like the things you and I are talking about. It's not about the money. It's about all the other stuff. Having more money for 99% of people is not the goal, but it's the experiences and family and all these things. I said, “How do I help my clients with that?” And so, he put on a webinar and a presentation, and he's got a structure for helping walk through how do you do this? Everybody you talk to says, “Oh, it sounds awesome. How do you do that?” You go, “Um. I don't know.”
What do you say, how do you say it, and what do you do? And he's been through it on the receiving end, he's done it on the delivering end, and he's helped a lot of people do this, so he's got some metrics and practices for how to go through that and how to think about it. And I'd be happy to share sort of the framework and things if it's of interest, but I would say that one of the big takeaways for me was that it's never going to be perfect.
That's where I get stuck. I want to say exactly the right thing. It's not going to be perfect; it's not going to be complete, but getting it done is way more important than what gets done. And so, as viewers hear this and think, “Oh man, that'd be a really cool thing to do,” if you can do something, it doesn't matter if it’s perfect. Just doing that is really powerful, and I’d be happy to share some experiences.
Bridget: Yeah. Let's talk about the basic structure. I don't mind writing things, so if I'm going to write this, I say, “Okay, here's my legacy letter.” That's sentence one.
John: Yeah. So there's a framework that he puts together, which I thought was really useful. First, have an introduction. Why are you writing this thing? What's the motivation? Here's why I'm writing this letter to you. And then he suggests starting with an apology or expressing any regrets you have. And it sounds kind of weird when you hear it at first, but then you think, wait a minute, depending on relationships or feelings or different things, it makes sense to get all the bad stuff out of the way first.
Maybe it’s something like, “I wish I had spent more time with you,” or “I'm sorry I couldn't do this,” or anything that you might feel is hanging out there. It kind of clears the slate for the person being able to receive the rest of the letter. It depends on the relationship that you might have with the recipient. And again, I'm focusing on kids; I've written them for my kids. But I just want to bring up here too, Bridget, that when I was first listening to this, I shared this with my wife.
I said, “Hey, I think I want to do this for clients.” And her response was, “This shouldn't be just for clients or for kids, this should also be for spouses.” I thought, “Oh, what a cool idea.” And I know Blake is actually working on a segment of that because it's not just about parents and kids. That’s an easy relationship to focus on, but there're other relationships that are really meaningful in people's lives where this can be useful.
Bridget: Here's what I would have to say about the apologies: if you're getting stuck, move on.
John: Yeah.
Bridget: Sometimes people don't want to think about whatever they might have to apologize for. And if that's a sticking point, just stop. And the other thing I would say about apologies is don't try to explain it. Just say something like, “I'm sorry for…”
John: Right.
Bridget: Don't say, “But here were my motivations…” all that kind of stuff.
John: Yeah. And of course everybody’s unique, but it's interesting hearing him talk about the length. One or two pages is ideal, not a 10-page diary. If there's anything that you need to get cleaned off the plate, go ahead and do that. And then sort of the conversation is, I love you, I'm proud of you, and I believe in you. And from his experience, hearing it from his dad and as you think about it going to the kids, those things are important for them to hear. And hopefully they already know that, whatever age the kids are. But to have it expressed in writing is really important.
Bridget: Yeah. And especially because the grieving process is so mysterious. And it just seems like it might help you with that process.
John: Yeah, absolutely.
Bridget: It probably won't hurt.
John: What was that?
Bridget: It probably won't hurt.
John: Right.
Bridget: It's a low-risk proposition.
John: Yeah, absolutely. So I love you. I believe in you. I'm proud of you. Share some memories to the extent that it's useful, some things you want to leave behind, and then any life advice you might have. That's sort of the framework for these things.
Bridget: Life advice is interesting.
John: Yeah. And of course, everybody's letter is different. Some people don't address all the topics, but that's the idea. And again, getting something down is really the important part.
Bridget: Right, exactly. When we talked before the show, you were saying that some of your clients had ingenious ways of actually giving them to people.
John: Yeah. So one of the things that’s interesting is that this is not designed necessarily as something to put with your will and leave behind so that when you're gone, your kids read it. This is more a matter of sharing it with them on a current basis. And we had somebody who thought this was such a cool idea. She was visiting her adult kid’s house and put it in the Christmas tree thinking she'd find it. But the daughter never saw it until she was taking down the Christmas tree, and then she had this meaningful thing from her mom.
Bridget: What I find interesting about that story is that you don't have to set it up so you're there while they're reading it.
John: Right.
Bridget: That might make it awkward. I don't know. My social skills are pretty low, but that might make me feel awkward.
John: Yeah.
Bridget: You might feel like you have to respond in a certain way.
John: I shared this idea with a friend of mine. I said, “Hey, if you want to come to our presentation, please do.” He doesn't have children, and he said, “No, my partner and I tell each other these things. It's a cool idea, but I don't think it applies.” And I said to him, “A lot of times people, especially dads, have a hard time communicating these things, so to make sure your kids know it is super important.
But even if that doesn’t apply to you, think about when your spouse is gone. And if you have in their words, not your memory of what they said, but in their words, this tangible thing that's left behind, I think it's a really powerful thing.” You've lost parents, I've lost parents, and you think about some of those that they’ve left behind, letters and other things. Maybe these days you have videos.
But I think there's something really powerful about some of those tangible memories. And again, circling back, yup, let's make sure we take care of the wills and have all the powers of attorney in place. Where does the money go? What about the taxes? But when you think about what you're leaving behind, to leave behind something like this legacy letter for people and to have people know it while you're still alive, too, is really powerful.
Bridget: Well, here's another tip I would say, if you’re doing this with somebody and you're intending to leave it with your will, it might be nice to say, “I don't want you crying over me for the rest of your life.
John: Unless you want that😊
Bridget: So try to help them by saying, “You've got a great future. I believe in you.”
John: Yeah.
Bridget: It seems like this is a great way to wrap it up. Hi, I'm Bridget Sullivan Mermel. I've got a fee-only financial planning practice in Chicago, Illinois.
John: And I'm John Scherer. I've got a fee-only financial planning practice in Middleton, Wisconsin. Both Bridget and I are taking on new clients. We'd love to hear from you, but we're also both members of the Alliance of Comprehensive Planners, which is a nationwide group of planners that think similar to how we do. So if you like what you hear on our show and would like to find an advisor in your local area, check out acplanners.org.
Bridget: And please subscribe.
At Sullivan Mermel, Inc., we are fee-only financial planners located in Chicago, Illinois serving clients in Chicago and throughout the nation. We meet both in-person in our Chicago office and virtually through video conferencing and secure file transfer.
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