Caryn Flanagan: Continuing Bonds With Those We’ve Lost

"Eyes up, roll through."

"Eyes up, roll through," is the mantra of Caryn Flanagan whenever she encounters challenging terrain. She, a member of legendary ski team The Jackson Hole Air Force, founding member of and SkiGearTV, certified paddle board instructor, and now author. Twenty years ago, Caryn, and immediate family, experienced tremendous unexpected loss at the hands of a plane crash, when her daughters were very young. From this, Caryn has come to share her interpretation of death and loss through adolescent eyes in her brand new book, "Heaven In Your Bones." We hope you enjoy this episode, and please check out her website as well. Thank you, Caryn!

Emy Digrappa (00:00):

Hello, my name is Emy Digrappa. Each week we bring you stories asking our guest the question, why? We learn about passion, purpose and the human experience. Brought to you by Wyoming Humanities, with the generous support of the Wyoming Community Foundation. This is What's Your Why?

Today, we are talking to lifelong creative, Caryn Flanagan, and her newest work is called Heaven in Your Bones. Welcome, Caryn.

Caryn Flanagan (00:40):

Thank you, Emy. Great to be here.

Emy Digrappa (00:42):

Yeah. And, and I love calling you a lifelong creative because, your whole life you've been working in creativity in some way. Tell me all the ways that you've been creating and aspiring and-

Caryn Flanagan (00:57):


Emy Digrappa (00:57):

... learning new things.

Caryn Flanagan (00:59):

Oh my gosh. Well, I don't know how much time we have, so I'll just give you the bullet points. Um, I mean, I, I think my first love was writing as a child. I did a lot of writing as a young person. My second love was theater, which I discovered at the ripe old age of 12 and, uh, worked professionally in theater.

                 That's actually how I met you, what, 15 years ago maybe? I don't know. I've worked in jewelry design. I, I had a little side hobby that I turned into a side hustle and it was a great little, uh, business when my kids were young. A work-from-home business that I sold after a few years. Um, and yeah, a full circle back to writing with this project.

Emy Digrappa (01:44):

Well, tell me about this project, Heaven in Your Bones. And, and what was your journey to start writing this and, and how did this become a passion of yours?

Caryn Flanagan (01:53):

So, 20 years ago, we, my family suffered a terrible tragedy. My mom and dad were killed in a plane crash in Alaska. And you know that impacted us all extraordinarily deeply, and was a hard thing to reconcile. It's a, a, a lifetime of walking through grief and getting to know it and coming to terms with it.

                 And this particular book sprung from a conversation that happened maybe the day we even got the news. You can imagine that we got the, the phone call, uh, late one night end of August 2000. And, um, we were up all night trying to figure out what this meant for us and what we were gonna do and how we were gonna tell our children, who were six and four at the time, very young.

                 And we consulted with some friends and some, uh, professionals (laughs), uh, who gave us advice on how to, how to talk to the kids about this, about loss. And so, we started that journey. And Sarah, our youngest, well, both of them, they ask lots of questions. And kids wanna know, when you say to them, "Well, your grandparents have gone to heaven and we're not going to see them again," and they wanna know what that means.

                 "Well, where is heaven? And what do you mean I'm not gonna see them again?" And so, we tried to explain, um, that in a way they were with you. That they're always a part of you. That they'll be watching over you. And these were the kinda conversations we had throughout the day.

                 And later that evening, Sarah, who was only four at the time, came into my room and she said, "So mom, does that mean that heaven is in your bones?" And I'll never forget that moment. I just got goosebumps, and I thought, "Wow, that's something I need to use someday. Because that's so profound and it's simple, but it's beautiful."

                 And just, I was just blown away with how her young mind processed that in such a simple, but profound manner. And so, this book honors what my family experienced, but also the wisdom of a young child under duress.

Emy Digrappa (04:11):

And after you heard that and, and you kinda took that into yourself and said, "I, I relate to that. I get that. I'm gonna use that," because it obviously resonated with you too.

Caryn Flanagan (04:25):

Yes, it did. And, and I don't know, honestly, if I, if it, I was gonna use that at the time, but it was certainly, "I'm going to remember that."

Emy Digrappa (04:25):

Well, that's what I meant. Sorry.

Caryn Flanagan (04:31):

"And I'll use it through personal, just through my healing process." But then at some point, it became clear that that was a message that I wanted to share with the world. And I, and I wasn't really clear on how to do that. Um, and I just sat with it for a while. Obviously, we were dealing with a lot of other things at the time, so I think f- maybe five or six years later, um, I started thinking back on that and I came up with a manuscript for what was the original book. So this, this has been in my system for a really long time, literally 20 years. So I'm really happy to have it finally out in the world (laughs).

Emy Digrappa (05:09):

So you've literally been thinking about, because you're a creative writer anyway.

Caryn Flanagan (05:14):


Emy Digrappa (05:15):

And 'cause you've done a lot of theater.

Caryn Flanagan (05:18):

Mm-hmm (affirmative).

Emy Digrappa (05:18):

Have you written plays-

Caryn Flanagan (05:19):

I have.

Emy Digrappa (05:19):

... as well?

Caryn Flanagan (05:19):

I have.

Emy Digrappa (05:20):


Caryn Flanagan (05:20):

Yes. Yes.

Emy Digrappa (05:22):

So that, that really is part of who you are, is to put something out there in the world. And this was probably broiling up to the surface.

Caryn Flanagan (05:32):

Yeah. Yeah. It just felt, uh, for me, those messages through, through the written word are expressions that, that deserve a life beyond the soul that created them or the brain that created them. Um, and, and this became, you know, a children's story became the, the wheels, the, the, um, for this to happen.

                 And the original manuscript was lengthy and wordy and, and every word was precious to me. And I just didn't really know how to put it out in the world. I, I was afraid that a, you know, an editor was just gonna slash and cut and burn, and it wouldn't look anything like my story.

                 Um, but I did, um, a year ago, uh, in 2019, I took this manuscript to the Jackson Hole Writers Conference and got some critique and feedback on it. And that really was exceptionally helpful to me, um, in terms of sh- shaping it, defining it, figuring out who my audience was, and then really how to tell that story to that audience.

                 And it's a young audience. Um, three to six years old is really the target for this book. I know it's a hard topic to talk about with children, death and dying, especially sudden loss. Um, but I was encouraged by professionals in the mental health realm who said ver- really very few resources for young kids and to go for it. So I did. And so, here it is.

Emy Digrappa (06:53):

That is super exciting. And I think, I think writing it from that perspective is something probably very needed. And I noticed that your book proceeds go to a no- a nonprofit organization called ACCESS.

Caryn Flanagan (07:08):

Yes. Aircraft casualties support, um, for people who've lost loved ones in airline accidents, and they will get the proceeds from this book above my landed costs of publication. So yeah, I'm very happy to share these proceeds with them. They offer, um, phone, um, consults and they'll put, they'll pair people together, um, who have experienced similar losses.

                 The woman who started it, her name is Heidi Snow, and she lost her fiance in the Lockerbie crash. There was a big airliner crash over Scotland, boy, like 30 years ago. Anyhow, that prompted her to start this nonprofit. And she has consulted and helped people all over the world who are dealing with, with that type of loss.

Emy Digrappa (07:54):

Do you go through that grieving process all over again when you write a book like this?

Caryn Flanagan (08:00):

You know, because I started this so long ago and then kept coming back to it, not every time. But there certainly were times I feel like when there were breakthroughs in the writing process where I would, it would suddenly make itself known to me and said, "That's your story. Boom, that's it." And it would just wreck me (laughs). It was an emotional process, to be sure.

                 And now that I'm sending it out into the world and I'm getting responses from people, whether they knew my, my mom and dad or not, I'm feeling it, I'm feeling all those feels, but in a really positive and uplifting way. And I'm, I'm so glad I've, I went through with this. Again, it's such a personal story and it's, I just didn't know that people would wanna read it. But apparently, they do.

Emy Digrappa (08:44):

And maybe it's not just the plane crash, but it's also children who lose their parents in many other-

Caryn Flanagan (08:50):


Emy Digrappa (08:50):

... ways and experience that same loss that you probably have created a way for them to work through that through your book.

Caryn Flanagan (08:59):

Sure, sure. Everyone is experiencing loss at this time, whether it's loss of a job, loss of a lifestyle, loss of contact with friends. COVID has changed our world. And yes, this story focuses in on a specific type of loss, but the aftermath and what you're left with and what a child processes is probably pretty similar. Whether it was a plane crash or, or some other devastating event.

Emy Digrappa (09:31):

Caryn, this is the first book you've written, correct?

Caryn Flanagan (09:33):


Emy Digrappa (09:34):

So, what, what kind of lessons did you learn that you could share about writing a book, writing a children's book, and the steps you have to, to go through to make it happen?

Caryn Flanagan (09:49):

So, it's a great question. Um, number one, I would say, get as much feedback as possible. Get it into the hands of people whose opinion you value and people who might challenge you a little bit. Get it in front of strangers too, because they're gonna be more candid with you than your best friend (laughs).

                 If you have a story to tell, be brave and just tell it. Nobody has lived your, your experience, and so your perspective is unique. Even though to you it seems mundane and every day. It's 'cause you live with it every day (laughs). But to everybody else out there, it's a fresh story. So, so be brave and tell your story.

                 And then the third thing would be that there's one thing about writing a book, but then once you've pushed send and it's done, there, it takes on a life of its own, in which you have to wear lots of hats. You become a marketing director, a finance director (laughs), all of these things that, that maybe writers who, some happen to be a little bit introverted. Um, these are hard things for writers to do, I think. So I, I have a whole new respect for writers who find success after publication, but they do so through their own grit and their own, their own gumption.

                 Uh, you know, having worked in theater for a number of years, I'm comfortable in front of a crowd. I'm comfortable in front of a microphone. If I had been writing these past 40 years, not working out in front of crowds, um, it would be another story. So I really have a lot of respect for, for writers who then go out on the road and, and, and talk to people about their books. That's gotta be a big, a big, uh, a big deal for them.

Emy Digrappa (11:36):

And, and scary.

Caryn Flanagan (11:37):

Yeah, for sure.

Emy Digrappa (11:40):

Caryn, tell me what was, um ... After you talked about process, it's always really interesting to learn how you choose illustrations and how you choose an artist.

Caryn Flanagan (11:50):

So, um, for Heaven in Your Bones, I had a very clear image of what I wanted, the field that I wanted. And, uh, one day ... I live in East Jackson and one day I was waiting at the bus stop to go to the village to ski. And I was looking at, um, a public art installation. I don't know. A few years ago they, Public Art did this installation where they hired local artists to do wraps for these electrical boxes.

                 Well, the electrical box by the start bus stop at Redmond has the most charming illustration of a young girl running barefoot through a field of wild flowers. She has a board tucked under her arm, and she's running up towards these snow-capped mountains. And you assume it's a snowboard, maybe a surfboard. We don't know, but it has this levity and this energy and this lightness that I absolutely adored.

                 So I did a little research and found out that that artist, um, that created that is Kelly Halpin. And Kelly Halpin is a l-, uh, I think she was born and raised here in Jackson, and she's a terrific artist, illustrator, and she's also a total bad-ass mountain athlete and a wonderful young woman. So I hired her to, uh, I, I commissioned her to do the artwork for Heaven in Your Bones. And she did a spectacular job.

                 The story goes from kind of the surrealism to a little bit of mysticism as the kids sort of delve into these deeper questions of, what is heaven and how does it all work? And Kelly did a spectacular job of morphing that reality and ch- and adding some, some twinges of, of sort of mysticism to her artwork. And I just love the outcome. She did a terrific job.

Emy Digrappa (13:27):

That (laughs) is exciting. I can't, I can't wait to see that. Were you surprised at how welcoming, um, your book was, how it was well-received? Were you like blown away by that?

Caryn Flanagan (13:38):

Totally. Yes. I, uh, I only ordered a small number of books that I thought I would sell personally. The rest are available online, and I figured that a handful of people would contact me and say, "I would love a copy of your book." And I figured it would be like my aunts and uncles and maybe my old neighbor. And I'd get one to my mother-in-law (laughs). And I've had to reorder twice now and it's been less, it's been a week (laughs).

                 So, and, ah, such an incredible thing. Um, one of my little side hustles is I work as a ski instructor and I work with this extraordinary gentleman from New York. And I told him about my book, and he said, "I'm sending you money to buy 50 copies of the book so that you can donate them wherever you like." So I'm gonna have fixed, 50 extra copies. Did I say that right? 50 extra copies (laughs) to donate to schools, preschools-

Emy Digrappa (14:38):

Mm-hmm (affirmative).

Caryn Flanagan (14:39):

... wherever it can be of use. So I'm really excited about that and really honored by his gift.

Emy Digrappa (14:45):

And what does ACCESS think about this? I bet they're super excited that, not only did you create something is so relevant for, like you were saying, people during this time are experiencing loss in many different ways.

Caryn Flanagan (14:45):

Mm-hmm (affirmative).

Emy Digrappa (14:58):

And so, it's really an amazing gift to them as well as an organization.

Caryn Flanagan (15:04):

Yeah. I think they're happy to have the book as a resource that they can, um, they can recommend for their clients. Um, and I'm, I'm sure they're happy to have some extra funds too, yeah. And we're really happy to provide that for them.

Emy Digrappa (15:19):

So what has this done, uh, for your girls? Because, they knew their grandparents and then they lost them.

Caryn Flanagan (15:19):


Emy Digrappa (15:26):

And then you wrote this book and it was, was that f- full of conversation with them about how they felt then and how they feel now?

Caryn Flanagan (15:34):

Uh, that's such a great question. Um, you know, over the years ... Well, when we first lost my parents, we said, "We're gonna keep their names alive. Ellen, Grandma Ellen and Grandpa Allan. We'll talk about them daily. We're gonna, we're gonna just keep them close." 20 years goes by and a lot ha- a lot of water under the bridge, they're still a part of us, one hundred percent.

                 I think that for my kids, it was more their observation of my process of grief. And I feel like creating this book and seeing it as a resource for people, a way to help, was a way for me to, to give back. And it helped me to, it just helped me to process the loss and make sense of it, I think.

                 And I think my kids, because this project didn't really come live until the, you know, now they're 24 and 26 years old. So they're old enough to, to see what it's doing in the world and see what, what it's created. Um, so I think their relationship too through it is a little different now, because they're seeing it as adults.

Emy Digrappa (16:42):

Mm-hmm (affirmative).

Caryn Flanagan (16:42):

At the onset of all this, they were children. But I think they're really proud of me, it's just sweet.

Emy Digrappa (16:47):

Oh, I'm sure.

Caryn Flanagan (16:47):

And I love that (laughs).

Emy Digrappa (16:49):

Oh, I'm sure they are. Um, not just losing your parents suddenly, but when your parents die, there's this connection in the world that's lost. Even if they die of old age.

Caryn Flanagan (17:03):


Emy Digrappa (17:04):

It's, it's that grounding connection that I've, I've read about.

Caryn Flanagan (17:08):

Yes. But some of, some connections remain. And, and I'd like to address that, because ... So, my parents spent, at the time of their accident, they were spending the majority of the year in Jackson, Wyoming. And they were very deeply embedded in this community. They were volunteers and they were fundraisers and they were philanthropists and they were ... They took classes at the art association and (laughs), and ...

                 You know, they did so much in this community and they were well loved. So when, at the time of the accident, I was living in Colorado and we ended up moving up here two years later. Um, part of the reason we did that was because, every time we would come visit, we would inevitably run into people who said, "I loved your parents. They were remarkable people. It's great to see you. It keeps them close having you here." And so, yeah.

Emy Digrappa (18:10):

That, that's really great.

Caryn Flanagan (18:10):


Emy Digrappa (18:11):

And I love hearing that, and that you can still have those connections.

Caryn Flanagan (18:16):

I still do. I still run into people and, and those stories just, you know, boom. It's like, they're right there. It's really, it's so healing. It's, it's-

Emy Digrappa (18:24):


Caryn Flanagan (18:24):

... terrific.

Emy Digrappa (18:25):

Really heartwarming.

Caryn Flanagan (18:25):

Yeah, it's good. It, it is good.

Emy Digrappa (18:27):

Well, thank you so much for talking to me today, Caryn.

Caryn Flanagan (18:30):

My pleasure, Emy. Thanks for having me.

Emy Digrappa (18:40):

Thank you for joining us for this episode of What's Your Why? Brought to you by Wyoming Humanities, with support from Wyoming Community Foundation and generous supporters like you. To learn more, go to, subscribe and never miss a show.