
We continue the Solo series on aging, retiring, and dying single by continuing our exploration of end-of-life issues. Financial advisor Todd Engmann joins Peter McGraw to discuss the “Family Love Letter” – a tool designed to help organize and communicate vital information to loved ones in case of incapacity or death. We explore how this document, can be a lifesaver for Solos without traditional family structures, ensuring that their wishes are known and respected. More importantly, the Family Love Letter is an act of generosity that eases the burden on love ones putting your affairs in order.
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Listen to Episode #228 here
Aging Single #8: Family Love Letter
Welcome back. Our series on aging, retiring, and dying single continues with our series within a series on end-of-life issues for solos. The previous episode focused on advanced directives. This episode was suggested to me by a friend. I thought the idea was so good I invited him to join us to discuss it. Meet Todd Engmann, a financial advisor with over 25 years of experience helping clients build, protect, and ultimately transfer their wealth.
He runs his practice at Cary Street Partners, a registered investment advisor with an office in Morristown, New Jersey. Todd has been a close friend since our college days at Rutgers University where we were both resident advisors together and spent countless hours on the basketball court. While I’m a lifelong bachelor, Todd met a girl in college around the same time that we met and jumped right on the relationship escalator, and they’ve done so quite successfully, celebrating their 29th anniversary. Todd is a long-time audience member of the show and a solo ally.
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Welcome, Todd.
Thank you for having me. We have come a long way.
I’m so thrilled that we have kept in touch. One of the things that has brought us closer, ironically, has been the show. Before joining Cary Street, you were doing a very long commute. You were filling your time with a variety of shows, including this one. You would call me with suggestions for guests, ideas, and reactions. We’ve started talking about single living. You are a fierce ally, which is really wonderful. You’re in the business of helping people, whether they be married or single, thrive financially.
Family Love Letter
You’re going to share a tool with us called the Family Love Letter that was developed by Donna Pagano and Jeff Scroggin. You can find this at FamilyLoveLetter.com. The Family Love Letter is a document designed to help individuals organize and communicate critical information to their loved ones in the event of their incapacity or death.

While it’s not a legal document, it serves as a vital supplement to your estate planning, ensuring that important details like financial assets, legal documents, and personal wishes are easily accessible to those who need them. It is important information to their loved ones in the event of their incapacity or death. Is this fair to say it puts all these important details like financial assets, legal documents, and personal wishes in this easy-to-read accessible format?
Yeah. That’s a good summary. Donna Pagano, who was a CFP, and Jeff Scroggin, who was an estate planning attorney, many years ago came together and came up with this resource because they had a clientele that they saw had a need to collect information for their families. I look at it as a tool and a resource. I look at it as a tool to have the conversation or open up the conversation with families, friends, loved ones, and so forth, and then a resource to record where your assets are and what your wishes are at the end of life. We’ll get into a little bit more detail, but I look at it as a tool to start the conversation, most importantly.
I could see this may happen with a spouse, but it can certainly happen with a single. You pass and you’re living alone. You might have an executor to your will. You might have people that are going to support you in your final days. You’re gone and they’re like, “Where are the passwords? Where are the assets? Where is everything?” We’ll get into it.
Passing Of A Loved One
I got weirdly emotional looking through this document. It’s 37 pages. In some ways, it reveals, especially if you’re successful in life and if you’ve done a good job planning and saving, how complicated contemporary living can be. In some ways, it’s a very generous thing to do for someone who’s going to generously give their time to help put your affairs in order, wrap up your estate, and so on. We’re going to talk about how this is a valuable tool, especially for solos. There might be some special considerations. Let’s step back for a moment and talk about some challenges that you’ve seen that people face with the passing of a loved one.
Unfortunately, talking about end-of-life wishes, issues, and assets is not something people get excited about. It’s not like playing for hours at the College Avenue gym. I’ve seen it go both ways. I’ve seen the family that plans and has the discussions. What I’ve learned over 25 years of working with clients is that if a family has a discussion, it doesn’t have to be a long, drawn-out discussion. It could be some preliminaries. When that loved one passes away, there’s so much ability to grieve in peace with grace and dignity. They can spend some time together grieving the loss of that loved one.
On the flip side, I’ve seen families that did not do any planning and did not have conversations. That’s where the person passes away and the family is dealt with confusion and chaos. They also have to grieve, but they can’t spend the time to have a graceful, peaceful, dignified period of grieving because they’re suddenly thrown into, “What do we do with so-and-so’s assets? Where are all the important papers and the wills, if there are any? We know nothing.”
I’ll tell you a quick story. It’s a personal story. Unfortunately, in January 2023, I lost both my mother-in-law and father-in-law. My father-in-law was thirteen years older than my mother-in-law. He was getting up there. He was over 90. As he was physically deteriorating in the last couple of years, my mother-in-law was very dedicated to taking care of him. She wanted to be the sole provider. She didn’t want anybody in the house. Particularly with COVID, she didn’t want any caretakers to come into the house and so forth.
We pleaded with her for years to allow us to get her some help. Unfortunately, she did not. As she started to decline in 2023, we talked about what her thoughts were about assets and what is going to happen if they should both pass on and what if one does and the other one doesn’t. Luckily, we had some ideas. She suddenly passed three days after my father-in-law. He was 90-something and she was 78. We thought we’d have plenty of time with her.
When she passed, we knew a little bit about what she had done. She had gone to an attorney, had done a will, and prepared a couple of trusts. We were able to grieve her sudden loss and spend that precious time as a family grieving her loss. It was a huge loss for us suddenly. I always say this. Having a discussion with the family about your wishes helps the family grieve the loss with some grace, some dignity, and some peace of mind. We were able to celebrate her life eventually, not go looking for assets and looking for paperwork and trying to find out where things were.
I lost my mom several years ago. It’s shocking to reflect on that. I was in charge. My mom had a very simple financial situation. She didn’t have much savings and had no assets. She had a house though. That was a pretty straightforward situation, but it still took a lot of time, effort, and energy getting death certificates and communicating with her bank, social security, and things like that to make folks aware. Even in her simple case, having something like this would’ve been useful. As things get more complex, it becomes especially so. Do you have another story about someone who was well-prepared and who might have even used this love letter?
Sure. I’ve got a great example of a family that made all the preparations and talked about wishes and where assets were put together. The Family Love Letter, the book that we’re talking about, I mentioned it as a resource and a tool. This can be done on a piece of paper and written down. However, the Family Love Letter, the actual 37 pages, are prompts. You may not think of everything. That’s why it’s really useful.
This particular family, for years, talked about what would happen if their mother passed away, needed care, and so forth. They were really prepared. They had everything written down. They had folders of all their accounts, all their documents, where things were, and professionals. She didn’t use a cell phone that much so she didn’t have a lot of digital assets.
What happened after she died was they had a really nice ceremony. I went to it. Friends were invited. They knew it was important for their mother to make sure those friends came to the ceremony. She had told them what she wanted to say at her ceremony. There wasn’t music but I have seen people put music in as wishes. Mine would be some U2 songs. I’ve been a fan for 30 years. They were able to complete the estate in an extraordinarily short period of time. It’s an estate that would have probably taken 2 or 3 years to go through probate but they were done within 1 year.
Tell people what probate is if they’re not familiar.
I tuned in to your episode with your CFP and estate planning attorney in preparation for this. I thought that was very good. Probate takes the assets and makes sure that everything is covered from credit to your current assets and where they get divided. It’s the legal process of dividing assets.
The government is involved in this.
Your court process. Having organized your papers, your documents, and where everything is, speeds up that process. If you become an executor, this is a gift to you that you’re not going to go searching for things for months. You’re going to find it all in one place.
The book is magazine-style. It’s a large document.
It’s like a big workbook.
It opens with a note from Scroggin, one of the creators of it. It has some examples in there like the ones that you talked about. It covers more broadly than the letter. It talks about things that you ought to have. Beneficiary designations, for example, if you have a brokerage account or a bank account, a living will, or a medical power of attorney, which is also called a durable healthcare power of attorney. That’s something we talked about in the previous aging episode, a durable general power of attorney.
It also has something called an ethical will, which is part of this document, which I’ve never heard of before. In the back, it has these prompts. First of all, it says, “I have or have not attached a more comprehensive ethical will,” but the one they have says, “When I’m gone, I hope my family will learn from my experiences.” You could fill in the, “I believe that the most important things in life are,” etc. It ends with, “This is how I’d like to be remembered.” It’s not a will for assets but it’s a will for perspective.
I look at it as a legacy. In my experience, when clients have passed away and they have done some kind of preparation and they’ve had the conversation, the legacy of that person is tremendously enhanced by the preparation. Their family grieves for their loss. I’ve seen it where there’s a sense of pride in their deceased parent, relative, or friend who took the time to put some planning and some documents together so that the people that are left behind, their lives easier. It is dignity, peace, grace, and legacy.
That’s very well said. I can imagine as I tussle with the notion of death, think about it, and recognize that you can’t have life without death. The two define each other. I could imagine writing this in a way that asks the people in my life to celebrate rather than commiserate, to be able to tell stories, to reminisce, and to be appreciative that we got to spend time together, that we have great memories, and so on.
A Different Perspective On Death
Think about giving your loved ones a gift. There’s a very strong cultural belief that you should be sad when someone dies. It’s a tragedy when someone dies. I talk about this. When someone divorces, people say, “I’m so sorry.” A lot of people say, “Don’t be sorry. This is a very good thing.” You’re allowed to see your death as something that’s not bad. That is part of life and is a chance to signal to the people who love you to look back on the good things.
I don’t think I told you about this, but my mother-in-law was a very friendly person. She had friends all over the place. All different types of people were her friends. She was a school teacher for her career. She kept in touch with a lot of people. When she died, my wife and I and other family members decided that we wanted to have a celebration at their favorite restaurant. It so happened we knew that their favorite restaurant was Applebee’s.
We went to Applebee’s after she passed away and found out that every Tuesday afternoon they went, she would order a blue moon and my father-in-law would order soup. They had the same waiter every time, a guy named Sully. It turned out that Sully had known them so well that as my father-in-law aged and was falling every once in a while, he picked my father-in-law up in the parking lot when he fell on the way to the car. This guy was really important to their life. We worked with Sully and the manager at Applebee’s. We said, “In a few months, we want to have a celebration. We want to invite all of their friends to come up to Applebee’s. Sully, we’d like for you to be there and be part of the celebration.”
That’s so nice.
We had the greatest time celebrating my mother and father-in-law’s life. People came up to us and said, “Your mom would’ve loved to have been here.”
What a great compliment.
How cool was that? We felt really good. It’s a solemn moment. We didn’t expect her to go. We did something that felt like she was there. The spirit was there. People were happy. I’m not a big blue moon fan but we all had a couple.
For people who don’t know that, it’s a beer.
You put an orange in it.
Personal Information And Investment
That’s right. Before we get to some of the tactics and issues around this, I’m going to flip through this document and highlight some things. If something stands out to you, interrupt me and we can talk about it. The love letter starts with who it’s from, and I would write Peter McGraw on here, and its effective date. You fill it out.
The first section is contact information. It has your financial professional. I would put Money Amy in here. It has your CPA, your estate planning attorney, a stockbroker if you have one, your national service officer or veteran advocate if you are a veteran, former employers, current employers, and so on. It has your doctor, banker, etc. I thought this was really fascinating. The next thing is it says what your investment strategy is, so from being very conservative to being risky. There’s a little bit of a survey and a few questions to answer. Why the investment strategy?
I’ve seen this a lot. A client dies and has a portfolio of stocks, bonds, and mutual funds. Oftentimes, the family that inherits it or the people that inherit it don’t want to dishonor the deceased person by selling it. They may have company stock. You see this a lot with companies that have been around for a long time, Merck, Johnson & Johnson, and Coca-Cola to name a few.
A certain international business machine company.
One of those old computer mainframe companies. Families want to know the strategy of a mother, father, or relative because they want to honor their loved one’s investment style. I’m not here to give investment advice, but we can argue that they really need to make sure that for the inherited, they make that portfolio match their risk tolerance, objectives, and so forth. That often is a very emotional discussion that I have with clients where we try to reason it out and talk about it.
I see that. It is your money if it’s been given to you. Unless there are strings attached, you get to decide to make changes to fit your stage in life perhaps. It has titles of your assets. For example, where you live. It then has a whole bunch of information about where your IRAs are hosted, whether you have a 401(k), stock options, deferred compensation, and Military retirement benefits. All of this stuff is the name of the company, the amount of money, who the beneficiary is, representative names, phone numbers, emails, and websites. You could imagine going through this one thing at a time and being like, “I didn’t know that Peter had an IRA.”
That’s right, especially in this world where digital assets are hidden within the computer and you don’t have a physical statement coming to the house every three months or monthly. If you have multiple IRAs and they’re online, your beneficiaries may never understand that you named them as beneficiaries or that you had IRAs. That helps you list it out.
This is what we learned with my mother-in-law. Luckily, my wife guessed my mother-in-law’s cell phone password. When we realized we needed to do two-factor authentication on a number of online accounts, bank accounts, and investment accounts, my heart dropped. We were like, “We’re going to have to try to figure out her cell phone password.” She figured it out on try number one, which means that was not a good password. It begs the point that you’ve got to have it written down somewhere so that whoever’s going to take care of your assets can figure that out.
That’s excellent. It goes on. It goes into real estate and frequent flyer programs. You could imagine someone who’s a lifetime traveler. They retire and they’ve got 900,000 frequent flyer miles. It has, “Money owed to me,” which is very interesting. It goes into lawsuits. You might have legal actions that are pending. This is really incredibly comprehensive. It goes into other assets. It also goes into liabilities. Do you owe money? Do you have a second mortgage? Do you have an auto loan? Do you have credit card debt? It has all these kinds of things that are there. Do you have subscriptions? If you think about it, we live in a world where all these subscriptions are hitting our credit cards.
My father-in-law had an investment advisor subscription that was $89 a month. I didn’t know about it. It took a while for the process to get access to accounts. I found that he has been paying this for three months since he passed on.
It goes into insurance coverage, life insurance, and Medigap insurance, which I didn’t even know existed. It goes into employment and VA stuff, and then it has a space for notes. This is interesting. In the fourth section, it says, “My documents.” This has 25 things, last will and testament, living trust, 529s, organ donation forms, child support agreements, citizenship papers, and your birth certificate. It then says, “Date signed and location of original.” It could be, “It’s in my lockbox in the closet,” or, “It’s in a safe deposit box,” or, “It’s in the top left desk drawer.”
It’s like, “That lockbox that’s in the basement, here’s where the key is,” or, “This is the combination.”
That’s right. It then goes into general information, phone numbers, access codes or passwords, and voicemail retrieval numbers.
There is a famous story in the Love Letter community of a family that inherited their uncle’s home. He lived solo. The family was a really nice family. When they sold the house, they sold it to a family. They were overjoyed that this young family bought the house. They stayed friendly with the new family. One day, the new family calls up the uncle’s family and says, “You won’t believe this. We are doing renovations. The contractor broke through a wall and found $25,000.” He was living by himself. Nobody knew he stored the money in his room. It’s an amazing story. Because, number one, the contractor told the new owner. The new owner was friendly enough and nice enough with his family. That’s a nice story.
It may not be $25,000. You may have a family heirloom jewelry that you want to go to this particular person. How about a pet? It’s on the list. What happens if you were to suddenly pass away? What happens with your pets? What’s their vet? We called up my in-laws’ vet. The vet told us, “There is somebody here who loves that dog and would love to take that dog in.” They came over a couple of days later and took that dog in.
Digital Assets And Final Wishes
It goes into digital assets, like Facebook passwords and LinkedIn passwords. What happens to your social media accounts when you die? Do they go blank and the person stops posting? Do you decide to post to these weaker ties that may exist to say, “Peter has passed. There’s going to be this memorial service if you want to join,” and so on? How do you sunset these important websites that exist?
Since we had my mother-in-law’s cell phone password, my wife was able to keep that open for a while and take in the messages of her friends from all over the world who had heard the news and either texted or posted to her pages.
That’s wonderful. It wraps up with more final wishes, like if there’s a funeral home that you want to be used. For me, for example, I want to be cremated. I don’t want a casket. I don’t want a burial. I want to be cremated and I want my ashes spread in a particular place.
Do you want some kind of plaque or a place? You don’t want anybody to go to a place and say, “Here lies Peter McGraw.”
At this moment, I want my ashes spread in Joshua Tree. There’s a tree that I’m friends with.
I heard about that. It’s your tree friend.
I have a tree friend in Joshua Tree. My sister has a hazy idea of where the tree is. She has a picture of the tree. She might have to do a little bit of hiking to spread my ashes. It is all these special requests, like, “I would like the following songs, music, or poetry played at my funeral.” It’s interesting. I gave my grandfather’s eulogy at 26, which was an incredible honor to be able to do. I was also one of the pallbearers.
Using Paper
His brother-in-law arranged a bagpipe player. This is an Irish Catholic family. As we are carrying his casket to the burial, this bagpipe player starts playing Amazing Grace. I lost it. It was so powerful for me to do that. It’s one of the most lasting memories from that day. Having something, a request for music, whether it be sad, in that case, celebratory, fun, playful, or whatever it is, poetry, or things that make it more personal and that you know especially that the person wants it can make that more meaningful. I want to ask something here. This is a paper document. Why paper? I can imagine this being a web form that you fill out. Is that a thought-out process?
Yes. It has to do with the security of all that information that is going into that booklet or that workbook. I spoke to Donna Pagano to make sure that we credit her and Jeff Scroggin appropriately. She reminded me that they do not have a digital version because of the fear of all these online scams. We’re talking about people who may not have been comfortable in the digital age. They may have grown up before and may not be savvy in keeping documents secure online.
I look at it as a document that you put in your underwear drawer because nobody’s going into your underwear drawer until it’s too late. You put it in a place where it’s not out. It’s hidden somewhere in your house but not hidden so much that right after you pass, somebody’s going to find it. You may also give a copy. If you’re a solo person, you may tell a friend or a loved one, “When it’s my time, I have all my stuff written out and it is here in my home,” or, “Here’s a copy of it,” if you feel comfortable doing that.
I have a friend who jokes. He says, “If I die before you, there are a couple of hard drives in my closet that I want you to dispose of.”
They’re like, “Wipe my browser history too.” I’ve noticed in your previous episodes, you say that a lot.
This is a document that you want to keep secure. That goes without saying because you have private messages. You have your social security number, passwords, and so on and so forth. Who you give it to is someone you have to trust with your secret life, not just your private life. It should be accessible but not too accessible is the way to say that. I wanted to clarify why it’s on paper.
Surviving Spouse Checklist
It’s interesting. This is called the Family Love Letter. There was only one thing in the packet that I didn’t like. It’s a separate document, and it’s called a Surviving Spouse Checklist: A 12-month Guide to Working with Your Advisors. This is like your to-do list with your advisor across a year of things that need to be done. For example, figure out benefits that may be available to you and things like discuss investment portfolios, assets, and financial needs. I chafe at the idea that it’s limited to a spouse because this could be a family of choice member, for example.
That’s a good point. Let’s face it. My first probably 10 to 20 clients in the 1990s were men who were married. They traded stocks. They invested. They bought mutual funds and bonds. They die and then I get a call from their widow who had no knowledge of the investing of the money and where it was. Maybe they knew where the checkbook was but had probably never written a check out. That’s a legacy of the industry and the age of the general population that we started this process out. The love letter is twenty-something years old, so probably the roots in that.
My guess is in ten years, that page will have a different name.
I would agree.
Most of our audience is single. They have important people in their life. They generally don’t have spouses. What are the special considerations with regard to creating this love letter knowing that you don’t have a ready-made spouse to hand it over to?
That’s something I’ve been thinking a lot about because 50% of my clients live solo.
Here’s the thing. If you lose your spouse, suddenly, you’re in our demographic.
I’m also talking about younger people who lost their spouses through divorce.
Rather gained their freedom through divorce.
There are a couple of things there. A married couple is going to know a lot of things about that person on a daily basis because they’re in proximity. It doesn’t have to be married. It can be partners. They have the proximity and they know where certain things are. The love letter is even more important for a solo person to have the ability to communicate their final wishes, where assets are, where the locations of assets are, and so forth to somebody, and it has to be somebody that they trust.
Can I add something to that?
Yeah.
The trust thing is paramount. It’s probably the most important thing given the delicate nature of the information in there. This came up in the advanced directives episode, the previous Aging Single episode, where I asked who is the ideal person to execute your advanced directives should you become incapacitated.
Teri, the guest, had an incredibly long list. She said, “Someone who’s a good decision-maker, someone who’s organized, someone who is emotionally intelligent so they can manage their personality, someone who can be confident and forceful in the case of conflict, and so on.” You’re like, “That’s an important skillset to be able to have.” I can imagine a similar set of skills. The person I want to give this to is not just someone I trust, but someone who’s organized, someone who’s a good communicator, and someone who has some understanding of financial instruments and knows what an IRA is, for example.
I read that. I agree with all that. I also want to add that the person that you select should really care about your legacy and be kinda the protector of your legacy. They need to be competent. They need to be a good communicator. They need to be able to spend the time necessary to make the communication necessary. They need to care about your legacy.
An advocate, so to speak.
They’re like, “When you pass on, we want to celebrate your life. We want to make sure everything that you have put down that you want to get accomplished after your death gets accomplished. We care about your legacy.”
That’s even if you might disagree with it. That’s an important thing. Someone decides to give their assets away to charity and it’s a charity that you may not agree with. Maybe they decide to give more to one person than another person that you think they should give equal. It’s not your choice, so you have to execute a decision that you might not agree with because you want to honor them.
A Lifelong Process
I told you I got a bit emotional looking through this. One of the emotions that I experienced was a little bit of anxiety because I was like, “Another thing to do on my to-do list.” This is not something that you knock out in 30 minutes. This is a major investment in time. We’ve made a strong case for why it’s worth the investment because it honors the people who are going to honor you. The biggest complaint on the apps is, “Don’t waste my time.” People are always like, “Don’t waste my time. If you don’t fill this out, you are going to waste your executor’s time.”
The Family Love Letter is only one thing. You also have a durable power of attorney. You have an advanced directive. There’s a lot that goes into this. People come to you for help. How do you get them started? You could see how you’d have cold feet, so to speak. You have to face your death. You have to think about your death, which people don’t like to do, and then you have to put pen to paper. You have to figure out your passwords and account numbers. I could see this would take a whole entire day to fill out, at least.
This is not a day project. This is a commitment to a lifelong process. A lot of people don’t deal with this because they don’t want to talk about their demise, although we all will experience that. They also are afraid that if their family, friends, next of kin, or whatever find out that they have assets, they might get stolen. They’re worried about their assets.
I’ve seen this. I had a 99-year-old client pass away. He lived solo for 35 years and did zero planning despite me begging him to do something. I even had an estate planning attorney meet us at McDonald’s. He’s a child of the Depression. I always said he never spent a dime and saved every penny. He did not trust anybody. Unfortunately, he decided to leave it to one of his sons and was like, “They’ll figure it out when I’m gone,” which is horrible because the guy’s going through it.
What I learned from that client was that he felt if he had told his relatives about his assets, his life would be minimalized to just money and that they only think about him as having this money that they’re going to inherit one day. They’re like, “Go ahead. Hurry up and die.” He was afraid of that. It was really fascinating when we sussed that out over a few discussions.
That is interesting. Suddenly, you become a walking dollar sign in the case of a not-so-high-integrity family member or a family member who’s desperate and in dire straits.
Think about this. His family has to grieve his loss, but they’re saying, “I thought he was a pretty smart guy. I thought he would have everything buttoned up. He didn’t do any planning for us. He didn’t do anything.” That family is grieving without that kind of thing I talked about before, grace, dignity, and peace of mind.
When a client comes to me and is having a struggle, we talk about how they want their legacy to turn out. Do they want their kids to say, “Dad did an amazing job taking care of the family during his life. He’s even speaking to me now after because he set up wills and trusts. He told me his passwords. I know where to get everything.” I talk to the clients about, “How do you want to be remembered?”
The flip side of that is I remember a family that lost somebody several years ago. They thought their dad was the bee’s knees or an awesome guy. The family comes to work. I had to show them where he worked and it was a mess. I remember the son saying to me, “I thought my dad was the greatest guy on the face of the earth and then I find out his desk is a mess, his office is a mess, and he didn’t do a lot of planning. We don’t know where any of the will stuff is. We’re in chaos.” It was really sad because that person, and I loved that guy, his family thought less of him.
It sounds deflated.
They wanted to celebrate his life, but they weren’t given that ability to do so because they were mourning but they were also in a state of confusion about where assets were. They didn’t know what to do. The guy was a little disorganized.
It sounds like when you’re having conversations with people, you’re nudging them or urging them to fill this out. You’re going to ask them, “Who are the people you’re going to give this docent to?” You have to ask them to think about that person. It sounds like one of the major motivators you use is to say, “Don’t do this for yourself. Do this for the people you love. It will release them of concerns. It will allow them to best remember you, best celebrate you, and honor your legacy.”
Therefore, they can celebrate their time together. In my mother-in-law and father-in-law’s example, we had talked about it for months. When we had a 2-day period where it looked like it was going to end up badly, we didn’t need to spend those final 2 days asking questions about financial assets and panicking over where things were. We didn’t ask, “Do you have a will? Do you have a trust?” We knew that already.
I want to add one other element calling back to the people you choose to share this with. As you get older, you want to find younger people to share it with. This came up in the estate planning episode. It takes some vigor to deal with all of this stuff, so you want someone who is fully cognitively healthy, who is savvy, and who is going to be, in some ways, more of a digital native, for example. I don’t want my 90-year-old best friend trying to get into my Twitter account because it’s not clear that that’s the ideal person to do that. You might have to change who that person is depending on where you are in life.
It’s also a reason why you may not choose to give it to somebody. You may leave it in your underwear drawer. I joke about the underwear drawer but think about it. What’s the first place you go to when somebody dies? You go to the underwear drawer to see what’s in there. You’re not looking for underwear. You want to see if there are any other things in there. They’re going to find it.
Are there any other strategies to get people going on this? I could see there would be a lot of reluctance. We live busy lives. What other tactics do you use to encourage people to get rolling on this?
In the past, I’ve had a webinar where I’ve invited clients and friends. In fact, it’s been a great opportunity to open up the conversation for people. I sent the link to everybody and said, “Spread this around. Send this to whoever you think might benefit from it.”
It sounds like everyone.
We had a great response. I’m going to do that again. I’ll have another webinar soon. One of the things it does is it allows people to open up the conversation. It might be something like, “Mom and Dad, I heard an amazing podcast the other day. It was about how families can communicate end-of-life issues so that when the time comes, and we don’t want it to come soon, we can all take the time to be together in comfort, peace, and grace and not worry about assets, who you want to invite to your service, and whether you want to have a priest or a rabbi. We’ll talk about those things now so that when you’re older and it’s getting closer, we don’t have to worry about that kind of stuff. Let’s talk about that.”
They could also say this. I did this to my parents. I said, “I’ve been really focusing on helping clients and their families have that conversation about end-of-life matters. Nobody wants to talk about it, but there’s this great book. It’s called Family Love Letter. I know you don’t want to talk about it, but let me give this to you. Take a look at it. Start writing a few things down, and then we’ll come back to it.” My dad’s a very private guy. My mom was interested in it. They’re working on it. We’re starting to talk about it. We don’t have any concerns about their immediate demise. Hopefully, we’ve got many years to go, but it allowed me to open up the conversation that we would never have had otherwise.
Certainly, this episode could be a good place to start for people. Suppose you have a loved one that you’re concerned about, especially if you are the person who is going to fall on your shoulders.
That often happens as a solo. That happens a lot.
Misconceptions
There’s a phenomenon that the solos end up caring for their elderly parent because they have a little bit more bandwidth than their married siblings with children. You might want to prompt people that this episode could be a good place to see both sides of it. Are there any misconceptions about the Family Love Letter?
Yeah. You don’t have to fill the whole thing out. Doing a little bit is going to put the family on a better footing. If you had it, pick three things. If you wanted to do three things, I would say the location of the will or the lawyer that you used, the cell phone password, and then if you have a pet, what happens to that pet.
I’m not going to speak for my friend, Clover, but she has a dog, Scout. A regular audience knows that I borrow Scout sometimes.
I’ve heard.
Scout and I are quite fond of each other. We get along great. Let’s flip it. Imagine I have a dog and I have a friend who borrows the dog a couple of days a month. No one else really knows about this. You put in there, “My friend, Clover, loves my dog, X. Check with her to see if she wants X,” and that kind of thing.
However, Shannon finds out that you’ve passed, takes a plane to Denver, sees your dog there, and says, “I got to go to the shelter and give this dog up for adoption because I got to go back to New Jersey in a couple of days. I can’t take it back with me.”
Shannon is my sister, for anyone who’s not familiar. That’s right. You don’t have to fill the whole thing out. You can pick the most important things. That’s a good place to start. Start with the most important stuff.
The next misconception is you have time. Do it when you’re older. I lost a friend who was 60 years old. She died of a heart attack overnight. I saw her that morning and didn’t come back to the gym the next day. I had no idea. I’ve never talked to her about it so I don’t know if she did any planning or any kind of organization. It reminded me, as I’m thinking about this episode, that you don’t have to be 75 and older or 80 and older to do this. You can do this anytime.
Getting In Touch
A lot of these things stay the same forever. Your brokerage account number, the phone number, the address, and all those kinds of things. You should probably change your password on occasion. Donna Pagano and Jeff Scroggin created this Family Love Letter. If someone wants it, how do they find it?
They have a website, FamilyLoveLetter.com. There are other resources on that website. The booklet is available for about $30. You can go there. You certainly can engage me in a discussion. I have a limited supply of free copies but it’s for people that engage me in planning and discussion with their investments and discussion about their roadmap. I’m happy to have that discussion, but I can’t give them all away for free. There are two ways to do that.
One is FamilyLoveLetter.com. $30 seems like a great deal for this. It is a shockingly good deal. We’ve been friends for 30-plus years. You’re one of my oldest friends. I can say this very comfortably. I trust you with my life. I would trust you with everything I have.
Thank you.
That’s my highest endorsement. What if someone wanted to reach out to you? I don’t want everybody emailing me, “How can I get in touch with Todd?”
You search Todd Engmann on LinkedIn, @ToddEngmannFinancialAdvisor.
Episode Wrap-up
What are your final thoughts reflecting on this conversation, the Family Love Letter, and the episode?
We’re all in this world together. It’s one of my missions to help people. That’s why I’m a financial advisor. I love helping people. This is after my mother-in-law and Father-in-law passed away. I got reinvigorated about helping people and helping people live a life with grace, dignity, respect, and care. It personally makes me feel good to be a part of that. My clients become friends and have long-term relationships. I want those families to have the best possible outcome that they can. I want to spread that message like you’re spreading your solo message. I want to spread the message that there is a better way. We have to talk about it. The love letter is a tool to get you to begin that conversation.
You’re incredibly of high integrity. I talk about the three characteristics of a remarkable friend. They bring value to your life and vice versa. You’ve been bringing value to my life since we met training to be resident advisors. They are of high integrity. They show up when they say they do. They keep your secrets. They’re honest. They’re reliable. They’re also anti-jealous. They celebrate your successes and they commiserate your failures. They’re not in competition with you.
I’m very proud of you.
I appreciate that. One of the things that I especially like about you, and it’s part of the value you bring not just to our relationship but to the world, is your optimism. You are an incredibly optimistic person. It has served you well. It serves the people in your life, whether it be your clients, your friends, or your family members. Your optimism shows up in this episode. You could take this Family Love Letter and see it as something very pessimistic, as a symbol of death, or as a symbol of demise. What you have done is reverse that. It’s a symbol of legacy, a symbol of celebration, and a symbol of honoring people in your life. I really appreciate that framing.
I appreciate you. Thank you.
Thank you. Cheers.
Thank you. Cheers.
Important Links
- Cary Street Partners
- @ToddEngmannFinancialAdvisor – LinkedIn
- FamilyLoveLetter.com
- Family Love Letter
- Aging Single #7: Advance Directives For End-Of-Life
- Aging Single #3: Finances And Estate Planning
About Todd Engmann

A graduate of Rutgers University, Todd’s deep understanding of financial planning is complemented by his long-standing commitment to his clients’ well-being. His expertise extends to estate planning and wealth transfer strategies, including tools like the Family Love Letter, which helps families organize critical information and ease the transition during difficult times.
Beyond his professional accomplishments, Todd is also a devoted husband, celebrating 29 years of marriage with his college sweetheart. A friend and ally to the solo community, Todd is an avid listener of the Solo podcast and actively supports the show’s mission of living an extraordinary life, whether single or partnered.