How to Write a Letter Someone Will Keep for Life | Lindsay Hurty

0:00Jonathan Fields: So what if the most meaningful thing that you could do for someone you care about is simply to write them a letter? A few honest words written by hand maybe to someone you love, even if you're not a writer. What if a few words could literally change both of your lives? Our guest today is Lindsay Hurty. She spent years as a high school English teacher before stepping away to raise three kids. On the day her first child was born, she started writing her a tiny letter. one line a day, every day for five years. Today, she helps people write the letters that matter most. Love letters that live alongside a will or just a love letter in general.

0:39Jonathan Fields: Letters that mark big life's turning points or the small notes that maybe we keep meaning to send but kind of never do. The ones that would mean so much more than almost anything else that we could do. In this conversation, Lindsay walks us through the five types of letters she believes all of us can write and the simplified part structure that makes them doable, even if you're convinced that you are a terrible writer. And she has something to say about that too, on behalf of every English teacher, whoever made you feel that way. But it all traces back to one letter that Lindsay wrote at 14 to a math teacher who stopped her in a school hallway and told her he was dying.

1:18Jonathan Fields: Years later, she wrote him a second letter. He passed away five days after she mailed it and she never her back. And then years later, in a scene straight out of a movie, his daughter came running down a different hallway towards her with something she needed to say, and it changed the direction of Lindsay's life. You'll also hear Lindsay read the very first and very last entries from that five year journal I mentioned. And I'll share the story of the one book that I've written that will only ever exist as a single copy. So pull up a chair and maybe grab a pen or a pencil and a piece of paper.

1:55Jonathan Fields: So excited to share this conversation with you. I'm Jonathan Fields, and this is Good Life Project. And we'll dive right in after this short break.

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3:17Jonathan Fields: So produced by the Center for Effective Philanthropy, it offers grounded, honest, and practical guidance on how to make your giving count, whether you're donating$20 or$20 ,000. Phil brings on nonprofit leaders and experts to talk through philanthropy's biggest questions with heart and rigor. So if you want to move from intention to true impact, search for Giving Done Right wherever you listen to podcasts. Good Life Project is supported by Peloton. So full honesty here. I am not a runner. or never really have been. I'm a hiker. Give me a trail, some elevation, and a few hours, and I am genuinely happy.

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4:28Jonathan Fields: And once you're on it, you've got instructors who feel more like friends than drill sergeants with programs for wherever you're starting from. Call yourself a runner if you're just getting into it all the way to full race training if that's your world. Let yourself run. Explore the new Peloton Tread Flex at OnePeloton.com. It's so good to be hanging out with you. You and I have been in each other's orbits for a number of years now. You were a part of our, in the Spark Type days for me, the Surefire Advisor program. You've been out there doing amazing work in the world, if we take a step back in time, you spend a chunk of your professional life as a teacher, teaching kids, English.

5:12Jonathan Fields: Brave job. Thank you. At some point, though, you switched gears and you said there's this thing out there also called letter writing. It's not a new thing. It's been around for a million years, but this became a focus of yours. Take me into this evolution. Well, I loved being a high school English teacher. I loved the job. It's something though that when I became a mom, I had this moment where I thought, will I be able to do both well? And I'm someone who holds myself to a standard where if it's not going to be done well, I'd rather not do it. And motherhood was this thing that I was a kid who dreamed about becoming a mom.

6:02When I grew up, I wanted to be a mom more than anything else. So it felt like an opportunity that I needed to be most present for. So I left teaching for parenthood. And when I was pregnant with my first child, I have three, I was in a local bookshop, and I saw this five-year line-a-day journal and I plucked it off the shelf.

6:30Jonathan Fields: What does that mean? So it's an actual journal that each page is one day of the year and there's a little chunk on each page for a year going five, like five chunks. So you can write a journal entry every single day of the year and only take up the top fifth of the page. So like literally like basically write one line. There's room for one line, but yes. You can write really small and have a few sentences. And I thought this was called like a mom's line a day journal. And I thought this is perfect for me because I knew I was going to be leaving my career temporarily probably for parenthood. And I thought this is a great homework assignment for me because everyone says it flies by.

7:17But I think substantive stuff will happen. So on the day my daughter was born, I picked up this empty journal and I wrote my first entry. And I wrote it in the form of a letter to my child who was born that day. Like a really short, sweet. Just a really short. You were born today.

7:35Jonathan Fields: Do you remember the first line? I actually brought the journal with me to show you. I pulled it out of my fire safe suitcase to bring it to show you. Would you like to see it? I would love to. I'll show you. The handwriting is so small, I have to put on my reading glasses. So this, Moms, one line a day. And for those listening, it's holding up this kind of like almost like a quilted cover type of journal with gold edges. And it's fairly small, but really thick. So you can see it's filled. Wow. And every year I changed the color. You could see that. Kind of see it. It's different colors and it's really teeny writing.

8:14It's tiny writing. I can't even read it without my reading glasses now as I'm 16 years old.

8:18Jonathan Fields: Would you be open to reading the very first entry? Sure. I haven't read it in so long, but it was November 19th. Okay. This is 2010. And then we were three. You arrived at 5.05 a.m. today, and our hearts are permanently bigger now. you were born at home and you've already met all four of your grandparents and your aunt jenny you are our miracle does it make you feel just seeing and reading that now it's it takes me right back of course and i didn't even really realize i was writing her a letter You asked how I got into letter writing, and it's so part of me that I didn't even notice that I was writing letters, because I did this for all three of my kids every day of their lives for the first five years.

9:18Although, I'll be truthful, my third kid got three and a half years, because I got really burnt out. And so that started. And so letter writing was just in me from the get go. And I feel, how does it make me feel? I feel grateful that I can revisit that person that I was. I treasure this because should my child become a parent, she'll have access to me at the same stage, which we change so much in life. So I could look back at this time through a reminiscent lens and speak wisdom. But being in it, as we all remember who are parents, is very different. It's like this connection on a different level that you have with your parent.

10:08So I feel it wasn't something I set out thinking, I'm going to create a piece of legacy here. It was more the person in me who wanted to prove that every day was substantive because like a lot of parents who choose to be a full-time home-based parent and interrupt your career path for it, there's judgment and stigma. And a lot of people think that that's pure luxury. And to me, and I'm not saying it's not for some, you know, but for me, I took it very seriously. I still do. It's a huge part of my purpose at this stage of my midlife. And it has been for the last 16 years. And I wanted for myself to show myself that every single day there was value to it in this job.

10:59Jonathan Fields: Yeah. So when you're writing, when you start writing these tiny little like micro letters, are you writing to yourself or to your kid? In all of them, I found myself writing to them. I remember having this conscious moment of I want them to have access to who they were through their mother's lens because I knew them like nobody else did and they were too young to have their own consciousness. So they might have vague memories of their first five years, but I wanted them to be able to see them later in life. I want them to be able to see themselves more fully in that formative stage. That makes sense.

11:42So I wrote it to them. I wanted them to be self-aware, almost like a mirror, trying to be a mirror to them.

11:47Jonathan Fields: Yeah. Would you be open to, so you just shared the very first mini letter that you wrote to your first child. Would you be open to sharing the last one? Absolutely. I actually, when I finished her album, I mean her journal, I felt a little lost, to be honest. I had two more children at that point, and I still had their journals to write in. But those were to them. And I ended up writing her a longer letter that I started an email address for her that she didn't access until much later, until she was 14. It is her email address today. But I wrote the first email to that email address on her fifth birthday when there was no more room in this journal because I wanted it to be a marker.

12:40And that's actually become something I call these life letters that I help people write is markers in time that aren't necessarily monumental, but you want to capture a time in life that right now is what it is, but will someday be the past. And so I can read you what I wrote in the journal. I also happen to have the letter that I wrote her right after that, if you'd like. You showed up, the teacher in you.

13:06Jonathan Fields: I brought props. I'm showing up prepared. I had no idea. Your conversations always go down the most interesting paths. All right. So this is the night before her fifth birthday on November 18th, 2015. It was a Wednesday. day. I'm sad to complete this entry as it marks such a real closing chapter to a part of our lives. Good night, goodbye to age four. Goodbye sweet pink journal that's walked with us through every single day of your first five years of life. We went to see the Lion King tonight after sharing your first frozen hot chocolate at Serendipity. It was magical experiencing that with you and will forever be imprinted as one of my favorite memories.

13:53On this, my final entry, darling Penelope Kate, I want you to know being your mom is the luckiest, most treasured thing that will ever happen to me.

14:07So. How's that? it's just it feels perfect to know that i was able to capture that then and that's preserved i mean time moves forward with all the people in our relationships in our lives and one thing i've learned as a writer who really enjoys capturing small moments of everyday life and exploding that into meaning is that when you write it in the moment, you capture things that you simply forget as time goes on. And then it can start to feel generalized or we kind of put it into cliches. But then if you actually sit down and write the thing you're feeling in the moment, it's more raw, it's real, It captures something that's so pure about a moment.

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18:03Jonathan Fields: letter writing for you also is i mean this this was an example of you know you starting to write these tiny little letters to your kids every day for five years but there's an older bigger practice embedded in this for you and there is a story from years before that is when i first heard you tell it just so deeply moved me would you would you take us there i'd be happy to so i'm going to take you back a few decades. And I was in my late 20s, high school English teacher. And I'm walking down the corridor that's empty. It's between classes. I'm headed to the photocopier. And I hear my name being yelled from all the way down the hallway, Lindsay, Lindsay.

18:48And I look up and it's Regina. She is a new math teacher. We're not close, but she's running towards me. She's on a mission and I'm somehow involved. And although we're not close, we have a connection. And that is that her dad was my middle school math teacher, Mr. Minor. And I loved Mr. Minor. And when she and I first met, when she was at teacher orientation, I brought up, the connection was made and I brought up that I had been her dad's student. And to be honest, she received me, it was very passive reserved. She was very reserved about it, almost cold. And I thought, oh, I get it. I mean, this was her dad.

19:32And I had been a student 15 years before. So I didn't tell her any of my stories of remembering her dad, but he was the best. I mean, in middle school, I actually had him for two years, seventh and eighth grade. And when, you know, middle school is middle school. We all know it. It's a yucky, hard time. But we would go into his classroom and he was someone who was seemingly very cranky, but he was super sharp and just impossibly funny. Always. Every day we could count on that. And it just being in his classroom, I think every time we walked in, we felt intimidated, but lucky. So it was this fabulous pull for a middle schooler of I get to be here, but oh my gosh, I'm nervous.

20:19Humbled, I guess. And so he would do things that just got us all laughing. So for instance, on the first day of school, he said to us, because the class was set up in a very classic way, rows separated. And he was facing us at the teacher's desk. And he said, I'm going to be sitting in my seat this entire year. But there will be one day when I will get up and I am going to clap my hands and I'm going to say, okay, kids, it's time for oral math. This is the day that the principal comes in to observe me as a teacher. So what you're going to do is I'm going to start rattling off math equations. You're not going to understand any of it.

20:58And I'm going to go and go and go. And I want you to look as eager as you've ever looked like you're following completely along. And then I'm going to say, who has the answer? I want you all to shoot your hands in the air. And I'm going to call on one of you. And you're going to say something, anything. And I'm going to say, you got it. And I want the rest of you to go, yes, as if that was what you were thinking too. Because then the principal will know that I'm good at my job. Oh, I love that. And so he just did stuff like that all the time. He treated us like we were capable of maturing. And he let us in on the secret truth that sometimes even adults make stuff up.

21:35And he also was really, really good at teaching us math, hard math, algebra, you know, that stuff that you look at it at first. and you feel like you can't figure it out and then you get there. And it just, it was beautiful. Like in middle school, when everything is so open-ended and strange, math being so beautiful felt so perfect. I just loved it. And Mr. Minor often bragged about never taking a sick day in his 20 years of teaching. And so in my eighth grade year, when he missed a day and then a week, and then it turned into a long-term sub for a month, we all noticed. And one day, I was in the middle school hallway by myself.

22:21I was trying to get out of gym class and going to get a nurse pass. And I was walking past the faculty parking lot, and in walked Mr. Minor. And I couldn't, I was so happy to see him, but I also was taken aback by his appearance. His skin appeared gray. He looked starved. And I still said, hello, we miss you so much. How are you doing? And he looked me straight in the face and he said, I'm dying. And I'm having a surgery tomorrow and I don't know if I'm going to survive it. I was 14.

23:05And we continued to walk down the hallway together. And when he peeled off to the main office, we bid each other farewell. He was a little teary and he said, I'll do what I can to get back to the classroom. And I went on to the nurse's office. And at this point, I was actually undone. The nurse called my mom. She picked me up. and I in my emotional you know I was just a mess my mom had a suggestion for me and that was to write him a letter and so I took her advice and I did I sat down and I wrote a letter expressing to him his value in my life how he was a teacher in math of course but also I felt like he was He was a guide in how I wanted to live my life as a person with humor and intelligence.

24:03And we ended up driving the letter to his mailbox. He lived in our town. We knew where he lived. I don't know why, but we did. And we put it in his mailbox. And the next morning before school at the crack of dawn, Mr. Minor called my home. And he thanked me for the letter. And he said he would do everything he could to get back to the classroom. Now, that very night, coincidentally, I had a plan to go on this middle school pilgrimage with my youth group, and we went into New York City to St. John the Divine Cathedral for this overnight experience called Night Watch. and part of that experience is that there is a midnight candlelit service and they really help you embrace prayer and so obviously Mr.

24:54Minor was so on my mind that day and I prayed for him I lit candles and a week later we got the news that he survived his surgery and he went back to the classroom eventually and he was healthy and well for another nine years. So now flash forward, I'm 23 years old. I'm living and working in New York City and I get a phone call from my dad and he has gotten wind that Mr. Minor is again gravely ill. And so I did what I did the time before. Now I only needed to take a subway. I went back to St. John the Divine. I lit the candles where I seem to remember that they were. I prayed and I wrote him another letter.

25:43And in that letter, I told him that all those years ago, I had gone to the cathedral. I'd lit the candles. I had prayed and it had worked. So my hope is that that would happen again. And I also told him that at this point as a college graduate, I calculated that it had maybe been 90 teachers later, that I still held him up there as one of the top three teachers who really saw me and made me feel valued and helped me discover my purpose and how I wanted to pursue my education. and my early part of my life. Mr. Minor died five days later. He, my candles and my prayer didn't save him. I never heard from him.

26:35I went to his funeral. I didn't get a chance to talk to his wife and his daughters in the vast sea of former students of his. It was packed. but now five years later i'm in the hallway of the high school where i'm now a teacher myself and barreling down the hallway is mr minor's daughter regina and she comes up to me and she grabs my shoulders she shakes me and she said you didn't tell me you were that lindsey now this is out of context i mean i have no idea what she's talking about what do you mean and she says you didn't tell me you were the Lindsay who wrote the letters and lit the candles.

27:21My dad got your letter before he died. It meant so much to him. And it means so much to us in his legacy. Thank you. And right there in that hallway, something just clicked into place that I understood that, yeah, he was my math teacher, but he was teaching me something way bigger than that this whole time. And that was that there is tremendous value in writing down your emotions, expressing them and giving them to somebody. And in this case, yes, it mattered for Mr. Minor before he died. But it also really mattered for his family, for his daughters, his now grandchildren, his wife, because they didn't get to spend time with him in the classroom.

28:08They heard legends about him, but that wasn't the dad they knew. And so now they had this little piece of his legacy that was very real that they get to keep. And so for me, that really, and to be completely honest, I didn't realize that that's what that was teaching me, like in helping people write letters until a few years ago when a friend of mine who is a listener and subscriber to my sub stack actually asked me if I'd ever considered helping people like her, she has adult children, write a personal statement to live alongside her will. And I just hadn't ever really thought about putting the whole thing together as letter writing in this way.

28:56But that's when I recognized, oh my gosh, absolutely letter writing, there's so much value to it. Yeah.

29:04Jonathan Fields: I mean, I love so many parts of that story. So when then three years ago or so, so you're in a very different stage of your life, you have a love of writing clearly that has followed you. And that manifests, one way it shows up is you saying, hey, I'm going to write more regularly and publicly, I'll start a substack. and you're writing your substack and this one reader turned friend eventually asks you, hey, can you help me write this one very particular type of letter, which is a really interesting letter. I've sometimes heard that kind of letter referred to as an ethical will. A lot of us are familiar with the concept of a will.

29:41Jonathan Fields: I bequeathed X, Y, and Z to whatever my state is, here's who gets pieces of it. This concept of ethical will is kind of like a letter or another document that says, here's who I am, here's what I believe, here are the stories that matter, and oftentimes here's what I want you to know about you and you and you and us. Is that sort of like the gist of what she was asking for? It's similar. When she had known what an ethical will was, I hadn't at that point, I now do, but she had the unique and brutal experience. I guess it's actually unfortunately not too unique, but her mom had just passed from Alzheimer's.

30:23And so she had gone through the experience of caretaking for the last few years of her mom's life. And then when her mom did pass, you know, after death is a largely administrative experience for those who are left behind. And she just felt this absence of her mom's voice. She hadn't had contact with it for so many years, really, because her mom just wasn't who she knew her mom to be. And it made her so sad in the aftermath of her mom's death. When she was caretaking, she was so in the caretaking. But afterwards, and she was really reflecting on her mom's life, she felt something was missing. And so she was thinking ahead that while she is healthy and vibrant and not at all thinking about dying, her young adult children, she wanted them to have her now, her voice now when they experience her death.

31:19And I thought, first of all, that's incredibly wise. This particular woman happens to be a life coach, so I can tell why she's so smart about just living. So I see why she had the idea. but when she really wanted it to be a love letter, something that the lawyers might call a side letter if you're doing a typical will. But if you, yes, an ethical will is something where you do all those things you just described. And from what I understand, it's mostly about capturing who you are, how you live. Like you said, the stories that matter to you so that two generations out, instead of just hearing the name, oh, you know, great grandma Anna, you can actually read in her words who she was, what she stood for.

32:05And she's not just a name in the family history, right? You can really learn about her a little bit more. So it's a beautiful practice for those who do it. But the actual letter to someone, yes, I suppose it could be considered part of an ethical will. But it's also, when I think about end of life, so much focus is on net worth. our belongings, our money, our property, and that matters for sure. And our attorneys are very equipped at helping usher that process and help that process. But when I think about the worth of a life, I think about love. I think about relationships. I think about the invisible substance that matters.

32:52And I just don't know if we're accounting for that through our written words, it's not normalized in the, at the end of life preparation process.

33:03Jonathan Fields: And it kind of brings you back into a path of like, okay, so I want to actually create an opportunity for other people to be able to write letters and not just end of life letters, but letters for all different, that mark moments in time. I remember you talking about launch letters, which I guess is sort of like a parenting to a kid after maybe a high school graduation or college grad or just some moment where they're transitioning into something bigger and different? Some very clear moment. It could be a retirement. It could be a big move. It could be someone becoming a parent, a graduation, a marriage.

33:45Those are very sort of more common ones or typical ones. But when there's a clear before and after on a date. And although the next phase might be welcomed and joyous, it will never be the same from what it was before. So I call those launch letters where we're marking time of this before and encapsulating it before we get swept up in the after. And then the life letter is another one because, well, to take a step back, yes, when I started working with people on what I call legacy letters, these end of life love letters to accompany a will, I realized that a lot of people wanted to share their letters now.

34:34And they weren't dying. They said, I'm so happy I've put words to what I'm feeling. I want to share this. And so I thought, well, how beautiful. I love that. But I came up with five different types of letters that are all love letters. They're all infused with gratitude. But they're big letters that you would write and give to somebody. And so the first is this legacy letter that we've been talking about. The second is this launch letter. Next is something I call a life letter, which is a bit of a softer moment in time. I think of it as a time capsule. something now is so meaningful to you and you want to capture what this is, but it's not necessarily changing tomorrow.

35:17You just know that at some point in the future, this won't be normal. Like this isn't life anymore. So I actually just wrote one to my 12 year old son because he had a really pretty magical summer in his baseball life, his young little league baseball life. He, My son and his Little League team became state champs and got to represent Connecticut and play on ESPN. And they almost made it to the Little League's World Series. They were one game away. And yes, he has his memories. There are newspaper articles. There's a ton that will hold this summer in memory. And I got to be right there with him for the whole thing.

35:58and it was incredible and magical and hard and a lot of growth happened. A lot of self-awareness came about and I suspect that for my child, this is a pivotal moment in his becoming that we will look back at when he's say 18 and point to this. And so I wanted to capture it of what this has been and what I'm seeing in him and things he's said throughout this process that I just wanted it. So I did not give him the letter yet. I'm holding it. I'm going to tuck it away in the album of the whole thing and maybe he'll find it years later. Yeah. And he'll find it at some point. But that's what a life letter is.

36:47It's like a little time capsule that you want. So we got three letters. Yes. And then I also have a listen letter, which to me, this is like a personal reveal where you have something of great importance that's personal that you just need to tell somebody. And then I have a leader letter. And this is one that's personal in nature, but it's a professional audience. So, you know, let's say you have a company that you lead and something's happened in your own life that they do need to know about to better understand what's going on with you. And it's not necessarily going to affect the business, but you want them to know what's happening with you.

37:29So I call that a leader letter. So that just has a little bit of a different audience.

37:33Jonathan Fields: Yeah. It's interesting. So the five different types you just described, four of those resonate with me for a very specific reason when our daughter graduated college. So when people ask me, like, oh, you're a writer, like, how many books have you written? Which is always a weird question. And my tongue-in-cheek answer these days is six, four that you can read. And the one is because the first is really unreadable. But the other is because the last, I spent four years writing to a single person and there's one copy in print. And that was a book that I wrote to my daughter when she graduated college.

38:09Jonathan Fields: And it took me four years to get it out. And the book is a series of letters to her. And it includes all four of those first categories, like end of life legacy, launch letters, life letters, listen letters. There's just a whole mixture of all of those across, like enough to form a book. And it was things that I wanted to share about me, things I wanted to share about her and what I noticed in her. And it was in my mind in part also conversations that I really want to have that I think really matter that I don't think we'll ever just sit down and have. So I wanted to write, write it out in letter form and I gave it to her when she graduated.

38:52Jonathan Fields: And to me, that may be the most meaningful thing I'll ever write if I write a hundred more books, you know, and it was the thing that took me the longest to write because I was, and I'm still curious, like what your take is on this, because as I was writing this thing, and fitfully starting and stopping. And I generally don't do it. When I write, I generally, I flow pretty rapidly. It just comes out of me. This was so hard to do. And the reason was I kept finding myself dropping into teacher mode, teacher and preacher mode. And I was like, let me tell you about the world on high. Let me tell you about this.

39:30Jonathan Fields: Can we talk about perfectionism for a moment? And I'm like, you're being an idiot. This is not what your kid needs from you. Your kidneys, you just show up as a human being, like flaws and dorkiness and just kindness, you know, and owning the fact that you really don't know anything and that that's okay. And really just sharing like on a deeper level. And it literally took me four years to keep stripping that away, keep stripping it away and keep stripping it away until I finally got to a place where I'm like, yeah, this feels true to me. and it doesn't feel like I'm being arrogant or teaching from a lot.

40:11Jonathan Fields: It just felt like it was what it needed to be. This can be a challenging process. Can I ask you a question? Yeah. So it took four years. Were you continuing to add new letters to it over the four years or was that revision? No, it was mostly just new stuff. And also I would just step away for long periods of time because I would write and I would realize it's just not working. and I would kind of set it aside. And the thing that actually made me finish it was that I started writing it when she graduated high school with my intention to give it to her before she started college. Wow. And I wrote one letter and in what was then an old black and white composition notebook that we all used when we were kids and I shared it to her and then she wrote back to me.

40:59Jonathan Fields: And then I went to write more and that's when the switch flipped and I just couldn't get back into the place that I needed to get to. And I literally was carrying this very, very low-grade, probably shame that I told her I was doing this thing for her. And for years, I just couldn't make it happen until finally I said, okay, there's another opportunity here. She's about to have another big moment, and I want to do what I said I was going to do. and the October before she graduated college, I took a one-month sabbatical and that's all I did for a month and I just wrote and wrote and wrote and then revised and revised and in that month, that's when it came close enough so that I could say, okay, I'll be able to revise and edit and make it what it needs to be and then design it and then literally have one single copy, like book bound and printed for her like when she graduates.

41:58Jonathan Fields: I mean, there were times where I was writing in tears. you know the times where I was writing and I was laughing out loud largely at just like how insane I was or silly I was or like some of the kooky memories that I had so it was really deeply meaningful to me and what I was hoping was that I could I could somehow bestow to her like the feeling that I had while while I was reliving those things that I wanted to share and the feelings that I had in seeing her in so many different ways in her own life. I want her to know that I saw her in those ways. It's really beautiful. I wanted to ask you a question about your letter.

42:42Was there ever a point when you thought, is my audience my professional audience? Were you ever thinking about publishing this for a wider audience? For a hot second. Right, early on, I bet?

42:53Jonathan Fields: No, later. Much later? I need to completely push that out of my mind while I was writing. But I did keep finding myself writing to an audience when I was trying to write to her because that is my training. Yes. I spent 20 years writing to an audience. One of the other challenges for me, I had to keep pulling myself back from that saying, this is not what this is about. Yes. You're writing to one person, your kid, the person who breathes you in this world. Yes. To let all the other stuff go. So there was a hot second after I finished where I thought I was like, I think there's probably actually some really poignant things in here that would maybe matter to people beyond my kid.

43:33Jonathan Fields: And I considered it. And what I realized pretty quickly is, A, I don't own this anymore. It's actually not mine. And B, I would never even ask her for permission to do that because to me, even asking would cross the line. It takes away the gift of it, what you did for her. But who knows? Who knows the ripple effect that could come from this. She may share it with a future partner, future kids. Maybe she'll publish it. Maybe. I get viscerally how powerful this experience can be for a giver and receiver. And we'll be right back after a word from our sponsors. Good Life Project is sponsored by Wild Alaskan Company.

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46:57Jonathan Fields: There are going to be a lot of people joining us who are saying to themselves, well, this sounds lovely for you, your writers. Yes, and honestly, most people feel that they're terrible writers. That is a narrative that I think a lot of people hold from high school. Somebody somewhere, and I just want to apologize to all of you on behalf of whatever teacher was having a bad day or a bad moment. The former English teacher is officially apologizing. I am telling you that you are a good writer. We all have it in us. We do. And I also want to tell you that your personal letters are not being graded.

47:37No one is taking a red pen to them. No one is going to read your letter and think it could have been better. Because that's not what they're looking for. When someone is reading your letter, it is all about what they are feeling. And back to this idea of for the people who are out there saying, Yeah, good for you guys. You write, you're comfortable with a pen in hand. It's the voice in the letter and that connection of you being you in your most natural way is what you feel in a letter that is different than if you plugged in to chat GPT. send a loving letter to my child about how proud I am of them at their college graduation.

48:24And so if you sit down to write it, of course, I love to support people who feel a little helpless with the writing because it is a real thing. But I try to encourage people to channel just who I am and what you would say to someone, your loved one, if you saw them right here. If you just walked up them? How would you greet them? What would you say? What are the words? What's the nickname? You know, is it dear? Does it even start with dear, you know, Molly? Or is it something different? Is it her nickname shouting out with an exclamation point? Is it something else? What is an authentic greeting for you?

49:04And leading into an opening that very much sets that familiar tone so that you're not thinking so much about crafting words and language as much as you are about establishing this familiar tone with this person who you know and they know you. And then sort of breaking it down. I have a whole scaffolding that I'm happy to share with your audience.

49:32Jonathan Fields: And I think actually it would be helpful. I mean, I know every letter is going to be different and the focus and the emphasis is going to be different. But you do have this very simple sort of like five-part structure basically that's sort of a general overview of how you would think about these are like the major blocks. Could you walk through that? Yeah, sure. So it starts with, like I said, the opening. And that is to set the tone, create your attitude around what it is, what you're saying, establish context. So one little trick of that, especially around a life letter or a launch letter, a little tool is to just think of when it is that this person pops into your mind in your day-to-day life.

50:22What's the kind of thing that you're doing? So let's say you wanted to write a life letter to a former college roommate, let's say. and let's say you're in your home right now, it's 30 years later, there's a fly buzzing around, you pick up a fly swatter and you have this memory of being in your college dorm when there was that night when that fly wouldn't leave you guys alone and you woke up in the night. To start a letter with something like that, tell the story of I'm in my kitchen, there's a fly, I grab the fly swatter And I'm dropped right into that memory of that night in college. And boom, here we are, you know, in the relationship that only you and I have.

51:10You've used a little anecdote. And so that and then that one image could then seep into the next part of the letter is what I call the landscape of us. And this is just establishing our relationship and who we are. You know, gosh, all these years later, spending that time together in college as roommates has been one of the most meaningful pockets of time in my life. I adored that time with you. You know, so the landscape that this is who we are. Then the next part of the letter is the heart of the letter. And this is where you really open up with vulnerability about the thing you wanted to set out to say.

51:56And in some letters, this can be a little bit harder thing to admit. In some, it might feel awkward because it's so obvious and maybe cheesy. But this is where you open your heart with an I statement and say the thing. Like, I just miss you. I miss being around you. I miss your energy, if that's the thing to a college roommate, let's say. And then the next part of the letter is what I call the nurture of the letter. And this is where you then give them something of you. This is like where you, I think of it as giving them a hug with your words. You express your gratitude, your love, how much you value the memories you have and hopes for more shared memories in the future.

52:43and then the last is the closing and I actually suggest kind of making the closing really swift and neat and tidy. And if you find yourself in the closing having a lot more to say, it's probably because you didn't say everything you wanted to in the heart of it. But then another little tactic I share with writers is whatever image you started with, so in this example, the silly example I'm giving about the flyswatter, is that you might then close the letter by saying, it just amazes me that so much of your way of doing things has seeped into my way of doing things all these years later even in the way I swat a fly I swatted a fly or something like that and then you just close it out I think with a familiar sign off and a a nickname or a

53:31Jonathan Fields: just your name yeah I love that and by the way for those joining us Lindsay has been incredibly gracious and um well in the show notes we'll include a link to just a one pager which you don't have to memorize this or go back through it yes where we kind of walk through a little bit more process for you if you want to actually sit down and do this yourself um i love the the like the invitation i'll say you don't have to be a writer to do that or consider yourself having being right we're all writers at the end of the day yeah it's it's not about the craft or the prose it's just about in whatever form it takes just sharing what's in your heart sharing what feels like needs to be shared and said in that moment.

54:08Jonathan Fields: I'm curious whether you have a take about handwriting versus typing. I mean, I think handwriting is something of value that especially if we feel connected to the handwriting of say a parent, it's nice to have that. I think like you saw earlier when I was reading my journal that I kept my handwriting, even I have a little bit of a hard time reading it. So there's a part of me that wishes this whole thing were typed up. I think it's personal preference, but if it's a personal letter that is meant to be saved, I will then handwrite what I've typed. You work out what you say on the screen, and then once you feel like this is it, then you actually sit down and handwrite it.

54:52Jonathan Fields: That process works for me. At the end of the day, let's say somebody's joining us, and they're like, this sounds really cool. I've always been scared of doing something like this. I feel like I don't have the ability to do it, but you've kind of convinced me to at least give it a shot and they're going to go and do this. And I would encourage anyone to do this, right? And do you feel like it would be helpful for that person who's just really like, this is strange for them. It's a little, it's an alien. They're concerned, are they going to be able to do it? To think about first just writing it and assume during the writing process that maybe the recipient is actually never going to see it.

55:30Jonathan Fields: Yes. I very much recommend that. And I think I've written plenty of letters that will never be shared because it's a wonderful tool for figuring out what you really feel. A letter, writing a letter is very helpful in that way. But I think that's a very comfortable way to start to write the letter and know that it's not going to be shared. You'll tuck it away. but to experience it and see what it feels like. I have an offering once a month. It's called the Year of Meaningful Connection Letter Writing Project, where you can join me and I send you an email, you know, inspiration once a month to write a letter and have a little bit of accountability.

56:13And a recent one was writing to a lead character in your life. And someone wrote a comment that said, I just feel so awkward writing that to my wife. I just think it would be so awkward. And I get that because if you're not in the practice of pointing out to someone what they mean to you, it is hard to do. And often we let Hallmark take care of it, right? We just get the card that says the right thing and we just say from whoever. And that is a beginning. It shows that we feel something and we want to connect, but it's harder to do. but I wrote back to him I gave him a little challenge and I said well I guess I'll ask you this what feels more awkward never letting your wife know what she means to you or saying it in all your beautiful awkwardness and giving her the chance to feel seen and appreciated and that she can revisit that whenever she wants.

57:19He hasn't written back yet. But I think it's just, it's a little risk. Vulnerability is a risk. I would recommend getting really small note cards at first, you know, that you could write a little note on and, and just practice a sentence that you give to someone maybe, maybe not a full letter, just sharing little bits of thoughts. I mean, I keep on my desk, I keep note cards of various sizes so that I can do that when I have just what would be a fleeting thought. But it's a beautiful thought about somebody that I could send in text and sometimes do, but I maybe want it to be saved. I will just write it on a little note card and drop it in the mail or drop it at their house.

58:05because it doesn't need to be a whole long thing for me to express a moment of thinking of something that someone said and how beautiful I thought that was and that I haven't stopped thinking about that for a week now. I just want you to know that that mattered to me. Something like that. It's just starting a practice of saying the thing. I can honestly tell you, well, maybe there was one time, but for the most part, I'm pretty unapologetically vulnerable. I'll put it out there. And I can't remember a time when somebody hasn't smiled when I've said something positive about them or how they made me feel or made an observation of something about them that I think is special.

59:00people appreciate it. They feel good. It's not awkward to notice something about someone and name it. It's not awkward to have emotions. We all have them.

59:12Jonathan Fields: And I love the invitation that you just sort of, in a gentle, almost backhanded way, offered up and says, okay, if the long letter feels a little too much right now, it counts to just do a quick little note card. Like you don't have to actually sit down and write the big thing. Maybe eventually you do, but maybe also just work up to it and maybe just like a short little note, like literally like a thinking of you type of thing with a few sentences. It's a great, maybe that's all it ever leads to. But over time, if it becomes a practice, it really makes a difference. Or maybe that becomes sort of like the gateway drug to a fuller expression.

59:53Yes. Imagine opening the mail and receiving a note from a friend that said, I can count on my five fingers all the people who matter to me the most. And you're my pinky finger.

1:00:08Jonathan Fields: I think I'd cry. That's all you need to say. Just one. That's it. It doesn't have to be long. It doesn't have to be the full letter. but it's such a perfect package, an emotional package to put something into words, to write it onto paper and to gift it. And like you said earlier on, there's a ripple effect even if it's just within that receiver because you feel something when you get it but I think of what you wrote for your daughter and I think about how she received that at probably age 22, right? And to think of her reading that at 32 and 42 and 82, I mean, that's powerful connection that lasts.

1:01:01It just lives beyond our memories. Our brains can't hold on to the tangible emotions in the way that I think we'd all like them to because our brains aren't designed like that. But to read something that your parent wrote you, you know, 60 years ago is good stuff.

1:01:27Jonathan Fields: Yeah. Making for a good life there, I'd say. I hope so. It's a good place for us to come full circle as well. So in this container of a good life project, if I offer the phrase to live a good life, what comes up? I've been thinking about this because I know that you asked this question. And I think it's really that to be open to collecting wisdom from people all around you, collecting that, putting that into your life, and being willing to be an ambassador of that wisdom in other ways. So in the way that someone might collect sea glass, you find this little thing and you don't necessarily know how it came to you, but you find it and it's like treasure.

1:02:15I think wisdom's like that. And I think we all have that. I think everybody has something that they can teach us. I call them life teachers, people who are just out there and their human experience somehow positively impacts my own human experience or one's human experience. but to be open to it and let it seep in and just allow yourself to be a vessel where we share wisdom. Thank you. Thank you.

1:02:47Jonathan Fields: So let's talk about some of the big takeaways from this. One thing that I keep thinking about is Lindsay's line that your letters are not being graded. Nobody's taking a red pen to them. The person reading them is not evaluating your prose or your grammar. They're just feeling something. And most of us have let a high school English class talk us out of that for 40 years. Three other things maybe that we can hold on to here. First, her five letters. The legacy letter, the launch letter, the life letter, the listen letter, and the leader letter. Different moments, same job. Second thing is her structure, which starts with a small concrete anecdote and moves into what she calls the landscape of us.

1:03:30Jonathan Fields: and then the heart, then the nurture, then a short close. So straightforward, any of us can do it. And third is that ripple effect. Her letter reached a dying teacher, and then his wife and his daughters and his grandchildren, and she only found out years later by accident in a hallway. Most of the time, you may never find out at all, but that doesn't mean it's not worth writing it. So maybe here's something to do this week. Get a small note card, not even a letter, a card. Write three simple sentences to one person about something specific that they did that you haven't maybe stopped thinking about, and then actually mail it or give it to them.

1:04:11Jonathan Fields: And hey, before you go, do me a quick favor. Think of one person in your life who would really benefit from this conversation and send it to them, forward it to them so they can watch or listen too. And if you feel like it, go ahead and leave us a review wherever you get your podcast. truly does help us get discovered and brings more people into these conversations. This episode of Good Life Project was produced by executive producers, Lindsay Fox and me, Jonathan Fields. Editing help by Troy Young and Alejandro Ramirez. Chris Carter crafted our theme music. And of course, if you haven't already, go ahead and follow us wherever you get your podcasts so you never miss a conversation.

1:04:47Jonathan Fields: Until next time, I'm Jonathan Fields signing off for Good Life Project.

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