Legacy That Lasts: Storytelling, Identity & Family Connection with Kasia Flanagan

Together, they explore why storytelling is essential for family transition, how vulnerability creates belonging, and why legacy should be thought of as fluid rather than fixed. If you’ve ever wondered what it truly means to “leave something behind,” this conversation will inspire you to start recording your story today. 

What You’ll Hear in This Episode: 

• How Kasia’s childhood stories carried her from homelessness to a PhD 

• Why knowing your history strengthens identity across generations 

• The fears that keep families from sharing their stories—and how to face them 

• Why legacy is about influence, not just assets 

• How storytelling heals old wounds and opens new connection 

• A practical DIY guide to capturing your own family legacy 

 

Chapters in this episode:

00:00 Welcome & Introduction
01:17 Kasia’s Childhood and the Power of Family Stories
03:34 Why Knowing Your Story Shapes Identity
05:28 The Fears Behind Telling Your Story
08:24 How Stories Bridge Generations & Break Down Facades
11:24 Redefining Legacy: More Than Assets
15:33 Healing Through Storytelling & Vulnerability
17:34 How Everyday Legacies Helps Families Capture Their Story
19:42 Public Biography vs. Private Family Story
22:12 What Legacy Means to Kasia Personally
25:30 Legacy as Fluid, Not Fixed
26:24 A Practical Challenge: Start Recording Your Story Today
28:01 Where to Find Kasia’s Free DIY Legacy Guide

Connect with Kasia Flanagan: 

Website: https://everydaylegacies.com 
Free Resource: DIY Guide to Capturing Family History (available at top banner) 

Connect with Elizabeth Ledoux and the Transition Strategists: 

Website: https://transitionstrategists.com/ 
Facebook: https://www.facebook.com/thetransitionstrategists 
Elizabeth on LinkedIn: https://www.linkedin.com/in/elizabethledoux/ 
Transition Strategists on LinkedIn: https://www.linkedin.com/company/transitionstrategists/ 
Transition Strategists on YouTube: https://www.youtube.com/@transitionstrategists 

Subscribe to “The Business Transition Roadmap with Elizabeth Ledoux” on your favorite podcast player: 

Spotify: https://spoti.fi/3MxSYA2 
Apple Podcasts: https://apple.co/3IhMMux 

Get Elizabeth Ledoux and Laura Chiesman’s latest book, “It’s A Journey: The MUST-HAVE Roadmap to Successful Succession Planning”: https://amzn.to/3oq2LQv

 

Legacy That Lasts: Storytelling, Identity & Family Connection with Kasia Flanagan Transcript

Elizabeth Ledoux:
Hi everybody and welcome back to the Business Transition Roadmap podcast. I am thrilled today to introduce you all to Kasia Flanagan. She is our guest and she is just an incredible person. She’s the founder of Everyday Legacies, which is a boutique firm that does personal history. They create bespoke memoirs, family storybooks, and legacy films for high net worth and alternate worth families all over the world. She captures their values, life experiences, stories, all the fun stuff that a family wants and needs to keep as generations go by. She’s got a PhD in history and she’s lived in six different countries. So I’m just glad to welcome Kejia today and can’t wait to get into our conversation. So welcome.

Kasia Flanagan:
Thank you, Elizabeth, thank you. I’m happy to be with you today.

Elizabeth Ledoux:
Thanks. So why don’t we start? I just have such curiosity in knowing more about you and your background and then really what got you started in this and where’s your passion here?

Kasia Flanagan:
Yeah, great question. I would say, I tell people, I come from the opposite end of the spectrum from the high and ultra high net worth world. My parents, I grew up in Idaho, in rural Idaho, and my parents had challenges and I had a large family and definitely didn’t have any extra money or anything around. We spent a few years homeless and I missed a couple of years of high school and it was just sort of a crazy upbringing.

But through that, what I did have were family stories. I knew, I was close to my grandparents growing up. They were farmers in the Labarock area of Idaho, if anybody knows that area, and my great grandmother, I knew her story. And it really impacted me. I felt like, you my family were pioneers and that was something that I always kind of saw in myself. So as I went off into the world and did my own thing, I ended up going to university and then pursuing my PhD.

It really was my family’s story that kind of drove me forward and made me feel like, no matter what happened, I could overcome it because I had the strength of my ancestors in me. And I realized actually, I kind of laugh about that, but it’s really not a small thing. As a historian, I found I was studying identity from mixed race descendants of German Tongan and German Samoan families in the South Pacific. What I found in my research was that the more that these individuals knew about their family history, the more successful they were in their lives in many quantifiable ways.

So that was really fascinating to me. And it kind of led me into what I do now, which is the personal history side. I’m not doing professional history as much anymore, but it led me into what I do along with a love of entrepreneurs and their family stories and all that. So that’s kind of the short version of how I landed here.

Elizabeth Ledoux:
That’s great. That’s great. And it’s so interesting that you found that family members and families are more successful knowing their background and knowing their history. What do you think that connection is all about?

Kasia Flanagan:
Well, and it really is fascinating. There’s tons of research about it actually. When you start diving into it, you can see how it’s just a fact that the more you know about where you come from, it affects your identity. So it affects what you believe about yourself and where you believe you fit right inside your family, who you are.

In this world where we’re all struggling with issues of identity and belonging and connection, I don’t think there’s anything as powerful as really knowing who you are and where you come from and that that’s the foundation that you stand on. So when you have that, it gives you this leg up really in this world, again, of all these questions where everybody’s just kind of bumbling around struggling. When you know that, you have this ability to move forward in a way that without that, we flounder.

Elizabeth Ledoux:
Absolutely. Absolutely. So, you know, that brings up a couple of thoughts on my side is just with us doing transition work, working with families that, you know, we work with the founder owner at times, and they’re trying to figure out how to get the business or assets into the next generation’s hands, but they’re so sometimes afraid to talk about that and afraid to tell about that. And so I could see where some of the history, I’m wondering if, do you think that there’s fear in telling your story at times and really opening up and understanding what that means?

Kasia Flanagan:
Yes, you know what, there’s fear for so many reasons. One of them is that insecurity, right, of where we come from. For a lot of people, like, and it’s fascinating, I’ve read books about this too, that it’s almost like…

Elizabeth Ledoux:
Yeah.

Kasia Flanagan:
Ultra successful people sometimes have the worst backgrounds and the hardest times. And it’s like, they have to overcome the most. And once they do that, a lot of times you don’t want to go back to that world of pain and remember the heartache because you have to push it down in order to be successful, you know? So when you’re talking about your story, it brings up those painful parts sometimes. And so there’s that fear of the weakness, right? Because sometimes it’s just so much easier to succeed in business and it’s so much more black and white than the hard, the really hard work of the personal side and the soft side. So there’s that fear.

And then I think there’s the fear of, you know, the vulnerability of sharing the truth. And sometimes the truth isn’t pretty. But I always tell people like, you don’t have to share every nitty gritty detail. The important thing is being able to synthesize the lessons and the important information. And when I say that, I mean, it can feel kind of ethereal, like you might not know what is the most important information.

There’s lots of research out there that kind of tells us and shows us, and it’s a little bit dependent on the family and on the business because there’s some information that you’ll want to make sure absolutely your family has depending on what you’re working with, but the point is there. It’s helpful to have a guide.

It’s somebody who can walk you through and help you deal with those emotions as they come up. And then also to understand what really is the most important things that I need to record for my family. Because it can feel so overwhelming, right? Like how do you put a life down on paper? It’s overwhelming for anybody that’s lived over 15 years, right? So yeah, there’s fear in a lot of it, but.

Elizabeth Ledoux:
Yeah, absolutely.

Kasia Flanagan:
You know, like we know, there’s nothing that’s worth doing comes easily. And this is one of those things that is absolutely important and imperative really for the success of your family, know, generations down the line. But it can be hard. It can be really hard to do.

Elizabeth Ledoux:
Yeah, absolutely. Well, and just the idea of, yeah, how do you filter through what is important and not important? And one of the things that I’ve seen, because as a Tiger Chair, right, dealing with some of the conversations that we have in our Tiger 21 meetings, and then also in my 30 years of doing this, the facade sits there when the kids are looking at their parents.

And the newer generations are looking at this amazing generation that’s sitting in front of them. And they have this perception that it was easy, that it’s always been this way, that there weren’t any hardships or anything like that. And so I think as people start into really understanding what it’s going to take to take over some of the work that is behind all of this.

They look at it and it isn’t, they don’t know what to do with it, truly. Yeah, they just think it’s gonna be no problem.

Kasia Flanagan:
Yeah. Yeah. Yeah.

And you know, I think that’s where the stories become, stories are just the most powerful form of communication, right? Like they talk about public speakers. If a public speaker shares a story, it’s like 97% more likely to be memorable than somebody that just, you know, stands up there and quotes statistics. And it’s the same with our families.

When you wanna teach a lesson, the most impactful form of teaching is stories. So when you think about that and you’re thinking about sharing your story, it’s so important to share those hard times.

We learn, first of all, we as human individuals, right, learn a lot more from the difficult times of our lives than we do from the times when, you know, all the flowers are coming up perfectly in the garden. There’s no weeds, right? But it’s the work of weeding and watering and everything that really makes us who we are and shapes our character. And it can be so intimidating for a young person looking at their family. I mean, I’ve experienced this in different settings and within my family. I remember just feeling, I mean, imposter syndrome.

Elizabeth Ledoux:
So true.

Kasia Flanagan:
Like through the roof my whole life, especially with my professors and my undergrad I felt like there was such a gap between them and me right like they had it all together. They were smart. They had figured out school I was the first in my family to go to college. I didn’t even know what a PhD was, I didn’t know what degrees meant, I hadn’t heard these words like even the word the Holocaust. That’s horrible to say but I didn’t know what that was ’cause I missed those classes at school.

So there’s so much that I didn’t know. And it wasn’t until I had this professor, he had emigrated from Germany and he started telling me about what it was actually like to be him and to go through what he went through. And, you know, he worked in like a chemical plant while he was trying to put himself through school and had burn marks on his hands from the chemicals that he worked with and stayed up late at night studying.

Just, you know, his story, like suddenly realizing like he was me. I’m having to work hard and I cry at night and it’s really hard and it just it’s so powerful because stories allow us to relate. Stories are connection and when you just see that crystallized, know, finished image of your parents or the successful person that you aspire to be like if you don’t know all the hard steps that took to get there, yeah, it can feel.

Elizabeth Ledoux:
Yeah.

Kasia Flanagan:
Just unattainable, right? And then you just automatically feel like a loser because, well, if it’s hard for me and they’re suddenly just there, then, you know, but knowing that, no, there were steps they took and I can take those steps too, you know, it gives you permission to succeed.

Elizabeth Ledoux:
Absolutely. So let’s talk. Just, I want to ask you when you talk about legacy, right, and leaving that legacy, what does legacy really mean in your world? And what have you seen it mean for these families?

Kasia Flanagan:
Yeah, I’m so glad you asked that question because this is something that I talk to people about a lot. So for me,

Well, let me start with this. I think in the world a lot of the time, especially in the high and ultra high net worth world, when we talk legacy, we’re talking about what we’re leaving behind, right? And a lot of times what that is is tangible things. Like I have clients, they have universities named after them or parts of universities. They have buildings named after them. They have inventions that they’re leaving behind. Even in an academic world, you talk about a professor’s legacy and all these things that they’ve left.

About legacy, I think about it as being, you know, the people that you touched, the person that you were, the space you took up in the world, and basically what difference has your life made for people? And that does include, yes, that includes the hospital wings and, you know, the universities and the buildings and all of that, but more than anything, it’s the influence that you had interpersonally to the people that were closest to you.

And you talked about fear before and sometimes that’s the fear that you fear. Well, you know, maybe I haven’t treated my wife the best. Maybe my kids, I don’t have that relationship that I want with my kids. And part of that is the fear, right? That sadness, like maybe I focused too much on the wrong things. I don’t ever think that it’s too late. And I think that there’s a lot of forgiveness and healing that can happen as we share our stories. Because once again, it brings understanding, it brings relatability, connection and forgiveness.

So when we talk legacy to me, it’s really like, it’s the people and what you leave in them rather than just for them.

Elizabeth Ledoux:
Absolutely. Wow, that is so well said. And it is so important to remember that some of your legacy and probably one of the highest values for your family is leaving behind your thoughts, your feelings, your values, just all of those connections that you’ve been able to build. And there is such leadership in creating a family community. It’s incredible. Such leadership.

Kasia Flanagan:
Yeah, absolutely. Yeah, and I think we just can’t underestimate how impactful that is for our families because once again, it’s the foundation of their identity and identity impacts everything. There’s so much so many studies and so much research about identity and mental health and like, you know, again, knowing who you are and where you come from.

Even if, and I need to make this point, even if you don’t relate to them, right, like I have a break in my family, I don’t have a lot of association with my dad or his side of the family. So for me, hearing those stories, it’s also important for me to know the stories because that shows me in some ways what I don’t want to do or who I don’t want to be. But it’s important for me to have the stories no matter what.

Elizabeth Ledoux:
Sure.

Kasia Flanagan:
It doesn’t mean, it doesn’t always mean that you relate and you see yourself in them and you aspire to be that person or like them in any way. Sometimes, you know, we learn just as much from the bad examples and the bad stories as we do from the good. So I just share that because, you know, it’s not about, it’s not about like a rosy, rose colored glasses idea of a family or thinking everything’s perfect.

It’s really not, it’s just about being human and sharing your humanness and letting the people around you take from it what is going to be helpful for them in whatever, however that looks for them.

Elizabeth Ledoux:
Yeah, absolutely. One of our company values is basically to give yourself permission not to be perfect, but to be authentic and genuine. And I think showing up with authenticity, yeah, that authenticity and just being genuine in that moment, it really changes some of the connections and the relationships that you have. Even if they haven’t been great for you, just that small shift in doing some work with you and telling that story, there’s still time. Still time.

Kasia Flanagan:
Yes, yeah, there absolutely is. There’s so much healing that can take place. I’ve worked with families where, you know, I have a client that I just love, such a good man, but he made a lot of mistakes. He had, you know, extramarital affairs that broke his family eventually, and he has a son that he’s estranged from and was for like 25 years of his son’s life, and it was heartbreaking for him, and he had all these regrets. But over time, you know, time has a way of helping things to heal, and then the story

Elizabeth Ledoux:
Hmm.

Kasia Flanagan:
When he told his side of the story and he wrote down and he talked about you know how he the regrets that he had and things that he would do differently and what he learned about himself in the process of his own healing, you know, and I mean it’s just so impactful for the families and as a child to be able to have that from your parents especially when there’s some kind of rift I think again it might not it’s not like a perfect, you know, it’s not gonna, it’s not gonna, you can’t snap your fingers and change pain but

It helps. It just really helps to everybody, you know, to hear the side, everybody’s side of the story.

Elizabeth Ledoux:
Absolutely. Yeah, and have that opportunity. So storytelling is truly an art, and I’m sure that your clients are not artists always in that area. So how do you help people walk through telling a great story? What do you do to help them frame it and do it?

Kasia Flanagan:
Yeah, great question. Well.

I have to apologize because I love my job and I love being I love seeing what we get to produce for our clients and just how it impacts them and their families. It’s so exciting to see their stories come to life and every story is different. So we you know, we start with well, let’s just talk about our process. We start with what do you want out of this and what do you want for your children? And so we start with that conversation and you know, who is the audience? What do you want them to know? What is the end goal here? And then you know, we have these conversations

Elizabeth Ledoux:
It’s hard.

Kasia Flanagan:
These interviews, and they tell the story. And we try to stay, I mean, we try to be their voice, right? Like we’re not trying to make them sound like, know, William Faulkner or somebody, we’re making them sound like them, but we’re telling the story in a way that is compelling and truthful. And truth is the most powerful tool that you have when it comes to your story. You have to tell the truth or you lose all credibility. So again, that doesn’t mean every nitty gritty detail. But it means you can’t keep skeletons in the closet because eventually they’re going to come out and then, you know, if you haven’t talked about them, then, you know, your credibility goes out the window.

So we, we just, we tell the story, we tell it with truth and in the way that is going to be from our experience and you know, from what the client wants from that’s going to be the most impactful for them.

I will say our clients are involved every step of the process. I’ve had some clients take a lot of ownership in the actual writing and change things or write a lot of it themselves. We’ve even just come in and just edited for people and their own words as they’ve written them. And we have different levels of, you we can do something very basic, which is just their words, or we can do like an in-depth creative.

Elizabeth Ledoux:
Nice.

Kasia Flanagan:
Storytelling that turns it into this beautiful narrative that is compelling and engaging. So it’s really dependent on what the client wants and then staying true to their voice.

Elizabeth Ledoux:
Absolutely. Yeah, I have a favorite mentor and friend of mine. Her name is Deborah Girardi. And she’s so interesting in the work that she does. But she said most of the time when you meet someone, you meet their armor. Right? So most of the time when you meet someone, you don’t really meet me. You meet maybe my armor, which is my normal armor, until I feel psychologically safe.

Kasia Flanagan:
Yes.

Elizabeth Ledoux:
To start to talk and to start to let you get to know me. I would think that this process would be a little bit about that, that there might be some fear there and then it’s like, no, now it’s okay and I’m going to show you everything or at least the important parts that you want to get passed on in the legacy.

Kasia Flanagan:
Yes. Yes, and can I just say something with that? So I’ve had many people say to me and I’ve had clients actually say, well, I’ve already had, I’ve already written a book or I’ve already had a book written about me.

I mean, some of our clients, like, I mean, they’re amazing. They’ve done incredible things in the world and they’ve had publicity and they’ve had things written about them and they think, well, my kids can just go read my Wikipedia article or, know, or they can go watch me on the news or, know, there’s sports people and they can just go read about my career. But the thing is there.

There’s a huge difference, like you just brought up, there’s a huge difference in leaving, like the story that you tell the world versus the story that you tell your son or your daughter or your grandchild, they are two different stories and they probably should be. I’ve only read one public biography that I would say was, I mean it was pretty.

Elizabeth Ledoux:
Mmm.

Kasia Flanagan:
It was what I would kind of expect somebody to tell their kids that that was Larry Miller’s biography that his wife published after his death. And it was written in a way that I thought this would be really great for the family as well. But almost no other would I say. I mean, I just finished reading. I won’t say which book it was, but there was this big businessman in the US. Wrote a book and it was the worst, most boring book I’ve ever read because it was all about his business. There was nothing in there, hardly anything about his family or his kids. And I was just thinking the whole time, my gosh, please let this man have written something else for his family. Because if he lets that stand as his story in the world,

Elizabeth Ledoux:
No!

Kasia Flanagan:
I mean, it’s a travesty. Kids aren’t going to know him, his grandkids, they’re not going to have those questions answered outside of personal memories and stuff, which we could talk about that separately, but it’s very fickle. You can’t rely on communicated memory.

Anyway, just the point is, like you just mentioned, there’s two sides us, right? Like there’s that armored side, that public side, and there’s the private side. And we’re talking about the private side because it’s for the people that are closest to you that you have the biggest investment in.

Elizabeth Ledoux:
Yes.

Yeah, which makes perfect sense to me. So gosh, yeah. This has been such a great conversation and we’re getting close to being at the end of our time.

It always goes so fast for me.

So for you, what legacy would you want to be remembered for?

Kasia Flanagan:
That’s a great question. Do you know? Ever since I was a kid I have the most like burros mind. I’m constantly thinking about death which sounds terrible, but I think just like ever since I was a kid. I’ve just felt this urgency to live my life purposefully and every day I just think well if today was my last day like what would

Elizabeth Ledoux:
Okay.

Kasia Flanagan:
Would I be okay with that? Would I feel like I’d left anything undone? And of course you always do. I mean, there’s so many things. But if I’m I, and I don’t want to cry, but if my kids, have three girls and my husband, like if they know how much I love them, how much I love God, how much I love the Lord, and how much I want to serve the Lord by serving the world.

Elizabeth Ledoux:
Yes.

Kasia Flanagan:
By helping families, I think if I could set that example for them and leave that in them along with the knowledge that they can do anything. You know, they come from an incredible, line of incredible people who love them and who

You know, want them to succeed. Like, I had this insight when I was struggling one time in my PhD. Almost, it’s like a spiritual vision that I just saw in my mind some of my ancestors and had this feeling like they didn’t live their lives and sacrifice all that they sacrificed and go through all that they went through for me to fail.

Like they have a vested interest in my success in life. Like I carry their name and in a literal way and then also in a figurative way, right? Like I’m their offspring. And I hope that my children, that will be part of my legacy to them, that they’ll know that they come from a long line of people who love them and have a vested interest in their success and that they, because of that, they can do anything and they should. They should try and they should, they can do anything that they want to.

Elizabeth Ledoux:
Yeah.

That is so great. Wow, that’s so powerful the way that you put that. Thank you for sharing all of that with us today. That’s incredible. So I have, well, two last questions.

One, know, legacy is an interesting topic. And I think whether you’re an ultra high net worth person or a high net worth person or

Kasia Flanagan:
Thank you, Elizabeth. I’m grateful for your conversation.

Elizabeth Ledoux:A wonderful person who’s kind of an entrepreneurial owner, founder type person. You always have a story and there’s always a legacy to be left with the family no matter who you are I think as long as you have that family.

If one, just want to encourage everybody to consider that. What legacy are you wanting to leave, whether you’re a successor listening to this, a transition or somebody else. Just want to put that in your head. Then if we reframe legacy to be something fluid because it can change over time

Rather than something fixed. Like fixed to me is, you know, I give you my ring or I give you my home or I give you something. But if we change it to think of it as being more fluid than fixed, how do you think that would change how families and communities live today?

Kasia Flanagan:
That’s a great question. I think it becomes a little bit more purposeful and also takes a little bit of the pressure off because there’s no end point, right? Like we’re constantly, we are robust, dynamic beings who are constantly learning and growing and hopefully getting better all the time. And so the legacy that we leave and we kind of mentioned this, but it’s never too late. You can always improve as a parent, as a person, you know, as a…

Contributor on the earth and your story can always change. It can start out tragic and it can end beautifully.

Elizabeth Ledoux:
Absolutely, well said. All right, last question for sure. I always ask at the end of our sessions, what one thing would you like to leave with our audience today for them to take with them and to remember?

Kasia Flanagan:
Outside of the things that we’ve already talked about. You know, it can be easy to understand from a theoretical point of view, how important this is. But I just want people to understand how important it is from a practical side and that if you do nothing, then just sit down and actually, you know what, I’m sorry, a small plug. If you go to my website, I just released this, a DIY guide for the most important things that you need to record for your children. And if you were to just take a Sunday afternoon and do that, you don’t have to worry about writing a huge book.

I mean, if you leave a book, that is fantastic. But that can be overwhelming. It can be cost prohibitive to maybe to have somebody do it for you, but if you just, I mean just the practical aspect, just leave something. You cannot die with nothing. I mean it is a travesty.

I lost my mom last year and thankfully I helped her record about 10 pages of her personal history before she died. But there are so much more that I wish I had and the thing is when it’s too late, it is too late. You can’t go back.

So I think if people could just understand that it’s not just theoretical, it’s not just a nice idea or something you should get around to. I mean, do it now, do it this weekend, do it today. And there’s tools out there to help you.

Elizabeth Ledoux:
Yeah.

Gosh, thank you so much. And thanks for sharing that with us and all of your wisdom and all of your knowledge today. Kejia, you are just a fantastic lady doing a lot of great work in the world and really appreciate you being here today.

Can you just let our audience know where can they find you and how did they get their hands on that DIY document that you put out?

Kasia Flanagan:
And great. It’s very easy. My website is EverydayLegacies.com. So the idea is that you’re leaving your legacy every day and it’s just EverydayLegacies.com. If you go on there, there’s a banner right there at the top that is a free download. You do have to put in your email address, but once you do that, it’s right there in your inbox for you.

So please, I hope everyone takes advantage of it. It’s a really great resource and I will say it’s something that I’ve done for my family. I took a Sunday afternoon and I wrote that and you know, there you go.

Off my mind at least, if something were to happen to me, at least my kids on that.

Elizabeth Ledoux
That’s awesome. Thanks again, Kezia.

Kasia Flanagan:
My pleasure, Elizabeth, thank you.

 

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