Today, I interview Katherine Kennedy, who grew up feeling the need to appear like everything was perfect, avoiding hard conversations and hiding behind a mask. As the youngest in her family, she was often seen as the one who brought fun and laughter, but underneath, she struggled to express her true emotions. This sense of needing to present a perfect life, while holding in difficult feelings, left her disconnected from her authentic voice.
Her turning point came when she started working with students who were the first in their families to go to college. Listening to their stories of struggle and resilience helped her recognize her own need to speak her truth. Over time, Katherine learned to have deeper conversations with her family, especially her father, which brought them closer and allowed her to release the secrets she had held for so long.
Now, Katherine guides others in finding their voices through storytelling workshops and retreats. She believes that finding your voice is a muscle that can be built over time, and she creates spaces for people to share their stories, just as she learned to do, fostering deeper connections and personal growth.
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Katherine has spent over 30 years helping thousands of people share their stories with authenticity and confidence. Her career highlights include working with Teach for America and playing a key role in expanding the youth leadership program Summer Search into a national nonprofit. As a mentor, fundraiser, and Executive Director, she has dedicated her career to empowering others to express their true selves.
Katherine is also a skilled storytelling coach, guiding individuals in various settings to articulate their personal stories—whether through public speaking, writing, or meaningful conversations. In 2023, she published her first book, Speaking to What Matters: My Story of Learning How to Share What’s Inside, which reflects her passion for the transformative power of storytelling.
Living in San Francisco with her family, Katherine continues her mission to help people connect deeply with themselves and others through the art of storytelling.
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Transcript of Interview
Transcript of Interview
Find Your Voice, Change Your Life Podcast
Podcast Host: Dr. Doreen Downing
Free Guide to Fearless Speaking: Doreen7steps.com
Episode # 146 Katherine Kennedy
“Building the Inner Muscle of Self-Expression”
(00:00) Doreen Downing: Hi, this is Dr. Doreen Downing, and I am here today, and I’m so happy because I get to introduce you to a beautiful person who truly understands inner work and the depth we need to go to find our voice as well as has had a personal and we’ll share her personal story of the struggle to find who we truly are because who we truly are that’s where the voice comes.
It’s not just you’re working on your voice; you’re working on who you are that has and can have a voice. This is Katherine Kennedy. Hi, Katherine.
(00:41) Katherine Kennedy: Hi, Doreen. I’m so happy to be here.
(00:43) Doreen Downing: Yes, fabulous. You sent a bio, but I’m going to read or at least speak to it because you’ve had a 30-year career and you’ve helped thousands of people tell their story with authenticity and confidence.
I hope that’s ringing for the listeners right now, the juxtaposition of confidence and authenticity. I think it goes along with what I just said, that finding yourself, your true self is where you can be more confident to speak.
And I know Katherine, you feel grateful every single day that you get to do this work and you and your husband live close by to me in San Francisco and you have this phrase that you use, you have three adult-like kids, which shows me one of the things about your humor. You don’t take life so seriously.
Nothing brings you more joy than an honest, deep conversation. Hello, anytime you want to have that, I am available with you, for you. Then you said, “Well, maybe a hearty howling laugh.” The humor and the joy and the transformational work that you’ve done, I’m so glad to highlight and feature you today.
(02:02) Katherine Kennedy: Thank you. Well, you know that I’m a big fan of you Doreen. Fell in love with you and with that group of people at the Speaking Circles retreat, so I’ve been following you and listening to you. I do feel like we have this synergistic and mutual belief that everybody has a story and everybody needs to be heard and that it’s possible to feel more confident and become more of the person you were meant to become in this life. So, thank you for having me. I’m happy to be here.
(02:31) Doreen Downing: Wonderful. Just listening to you, I feel like I’m opening up myself and my curiosity, because you have obviously a strong belief in story, and you have a strong belief that all of us can come to know ourselves better through the stories that we have. But that means turning around and looking at our lives, doesn’t it?
(02:54) Katherine Kennedy: Yes, it can be really scary, actually. It’s not for the faint at heart. It takes not just stringing together a story, but it takes being able to talk about the hard stuff.
(03:06) Doreen Downing: Big breath. Let’s turn around together and let you put some eyes and help us see your story, your struggle finding your voice. I usually start pretty early back in life, but the twisted up or the abandonment of self, all those kinds of things can happen really early, but it could be later. So, just any place you want to land to share what you think were some of the early struggles you had around having voice.
(03:39) Katherine Kennedy: I’ve done a lot of reflection about this because I wrote my story a few years ago, and I’ve helped students and people of all ages tell their story. But when I look back on my own life and my own upbringing, it’s hard, as you said, to pinpoint potentially one moment but there was a moment when in the writing of my story and in the living of my life, I realized I was too afraid to speak about what was going on at home and what was going on inside of me.
I was 17 years old when a school counselor called me into his office. I was rushing around school. I was the student council president and he said, “Hey, Katherine, can you come into my office?” I said, “Sure,” but inside I thought, “Oh, no.” I thought of my troubles. So, I sat across from him and he said I hear you laughing in the hallway and I see you rushing around school trying to be helpful, but I look at you and I wonder, “Are you okay?”
(04:41) Doreen Downing: Wow, somebody who’s noticing, and somebody who’s in tune and sensitive. I’m already riveted by that moment, so say more.
(04:54) Katherine Kennedy: I didn’t know what to say and I couldn’t speak. I had such a mixture of fear and doubt and inability to let him into what was going on. And I have to tell you, what was going on for me was that I was from this incredible family.
So, I ended up working in my twenties and thirties helping low income kids be the first in their families to go to college. I got to listen and experience and help them tell their very hard stories. But here I was looking back when I was 17, I couldn’t speak about the hard stuff because I felt like this commitment to make everything appear like it was perfect.
I’m from Pittsburgh, Pennsylvania, and I had two parents. We had a red brick house and two-car garage. My parents were chasing the American dream, and so, on the outside, everything looked great. And for the most part, it was. But there was this commitment to not talk about messy things.
And when I was 13 years old, I heard my father on the phone talking to somebody outside of it. It wasn’t my mother because she was upstairs. I didn’t know what to do with that information because my father was an incredible man. I mean, he was. He was ambitious and dynamic. He’d walk into a room and light it up. I mean, he was my hero.
(06:25) Doreen Downing: Yes, but there was a secret.
(06:27) Katherine Kennedy: There was a secret and I held it in and that holding in of a secret—actually there’s this interesting thing that I’ve thought a lot about lately is when you hold in a secret, it becomes a betrayal and it’s almost as a betrayal of yourself.
(06:39) Doreen Downing: Absolutely. That’s a whole conversation right there. Let me just catch it. A secret that you have is a betrayal to yourself. Is that right? Okay.
(06:55) Katherine Kennedy: I betrayed myself by staying silent and holding all that in and not getting the help I needed. It was a moment in time when my parents had this incredible marriage of 57 years but there were a few years when my dad finally did, in essence, reach a pinnacle in his career that he had been working so hard to get to. Their marriage just was on shaky ground.
And I didn’t know what to do. I was the last one at home. I was the youngest of four. I don’t know in your podcast when you talk to other people, the baby of the family, the one that takes too much space and the loud one, that was me, but I wanted attention and I got attention, but I usually got attention in the wrong way.
Now, you mentioned that I like to have fun and that I like to laugh and I was fun, and I do love to laugh, and I was, on the one hand, so adored in my family, but what hurt me wasn’t the love that I felt. I felt so loved and I felt like I knew that I was in a wonderful family.
I just didn’t know how to talk about the things that hurt me and my resentments and my anger. And when you shut out that part of you, the person that gets hurt the most is the person who’s holding it all inside.
(08:10) Doreen Downing: There you go again, talking about us, whether it’s secrets or betrayal or holding ourselves back, even if it isn’t a secret, we’re just holding ourselves back and I love all the connections you’re making about these words that are like, how do we be more of ourselves when we lock ourselves away and, oh, you just got to take a deep breath already with listening to those moments in your life, what you’re talking about now, the learning, the perspective you have now around what we do to shut ourselves out.
(08:48) Katherine Kennedy: Yes and keep that mask on and keep ourselves distant from other people. I longed for connection. I long to speak the truth. I long to even just get mad and upset, and maybe even throw a tantrum. I don’t know. But I was too afraid to rock the boat.
(09:07) Doreen Downing: Well, I think that we both do the deeper inner work. We know the value of listening, and it feels like what you’re saying is that you weren’t listened to early on. So, that’s one way we get to practice having a voice. If somebody’s listening to us, we get to express ourselves, especially if it’s a safe place and we get to say, “Oh,” or whatever is bothering us. We get to tell the truth by listening. If there’s no—if listening is thin, we don’t get to practice using our voice, and we come up with all these strategies.
(09:45) Katherine Kennedy: And usually those strategies are self-defeating. Usually. I was very, very lucky though, Doreen, in my 20s. Well, not just 2 things happened, but 2 dimensions in my life, 2 things changed. I met this nonprofit that was helping kids be the 1st in their families to go to college and the way in which they worked with students was to listen to them and to help them—
(10:10) Doreen Downing: There we go. Listening. I must have anticipated something but—
(10:16) Katherine Kennedy: I learned this fundamental skill, this fundamental dimension of life, which is to listen longer and deeper and ask better questions.
(10:26) Doreen Downing: Yes.
(10:27) Katherine Kennedy: And conversation by conversation, I got to really understand how we are underneath it all when we take off the mask and despite our circumstances, I actually felt validated more for my upbringing for what I experienced on the inside and less, even though our backgrounds—the students I was working with were so different—I felt I found more similarities. I found more connection.
I found more shared humanity because we all struggle with isolation. We all are afraid to have the conversation. We’re all afraid to tell somebody how we really feel and I help them speak truth to those feelings. I realized over time that a lot of what they were feeling, they were finally naming for me the words in the ways that I was trying to express myself.
So they gave me so much courage to eventually have deeper conversations within my own family and ask my dad about the conversation that he’d had decades before and ask my mom about what was going on for her. We became so much closer because of that.
I just want to say, simultaneously, my father, to his credit, in my 20s started something called family meeting, which was about once a year when we’d get together—again, I’m the youngest of 4, so I have 3 older siblings—when we get together, we’d meet from whatever time in the morning, 9:30 to 12:30 or whatever, and everybody would be given a chance to just talk about what was going on. It wasn’t a chance to say, “Well, when you did this, this upset me.” It wasn’t that interventional meeting.
It was just a chance to sit down outside of cocktail hour, outside of a meal, and just be there for each other and listen to each other. So, here I have my professional life, learning how to listen, and I’m having it modeled at home, so to speak.
Between those two concurrent changes in my life, chip by chip, I really learned that the muscle—and it is a muscle—using your voice, speaking your truth, saying out loud what you feel, even when it doesn’t make sense, all of that is a muscle that can be built over time.
Frankly, it does take time. It’s not one therapy session. It’s not one workshop. It’s not one family meeting, but over time, little by little. You can develop into a more authentic person, version of the person that you want to be, and you can be more confident in what comes out of your mouth.
And, as you know, I’ve pursued lots of ways to learn and grow, like speaking circles and other ways to invest in my voice and in others. So, finding your voice is a lifelong voyage.
(13:25) Doreen Downing: Set the sails. And especially if you’re together with people who are sailing. It’s just a thrill and that’s how I feel about you, especially today, us having a deeper conversation like this and me getting to know those particular moments in your life. Thank you.
(13:52) Katherine Kennedy: I feel like I was a little bit like in the hero’s journey of being called to see if this was the work that I really was meant to be, and to have, and to become in my own marriage too. I must tell you one more personal thing that really challenged me a few years into my marriage.
My husband and I were with the stress of three kids, just feeling distant, and instead of doing what I knew, which was to just hunker down and accept what is, and to maybe fester on the inside some uncomfortable and not so beautiful feelings towards somebody you actually care about, we had the courage to ask for help and went and saw a therapist and got a lot of help early on in our marriage.
That alone was such a gift because it’s inevitable to have challenges with people. In learning how to be intimate, that to me is as much around finding your voice as learning the skills to be intimate because asking for what you need in a deep relationship, knowing what you need, knowing what you want, to me, finding your voice isn’t just about being confident enough to like get up on stage and tell your story, it’s really about the deeper, more personal, frankly in my eyes, more important work of being in a relationship with somebody, and really being yourself, and showing up as the person that you really want to be.
(15:18) Doreen Downing: Beautiful. Yes, I absolutely agree. In fact, I think that it took me years and years to find myself, my true self, and then, of course, the voice follows because we line up more confidently if we are more confident about who we are. It took me into my fifties to connect with the man I’m now married to, and we’ve been married 15 years, and I totally relate to what you just said about the willingness to step into the harder conversations.
Yes, it’s hard to show up on stage, pick up a microphone, and share your message or your story, but life is your stage is what we say.
(16:03) Katherine Kennedy: Oh, I love that. Life is your stage. Yes, the most important stage you can live on and the most important audience is usually that audience in 1.
(16:12) Doreen Downing: You are just hitting all sorts of nuggets, digging out, or hitting balls out of the park. Well, I’m going to come back. I’m going to take a break quickly, but I want to come back and talk about your book, Speaking to What Matters: My Story of Learning How to Share What’s Inside.
So, we’ll be back in just a second. You guys get to listen to what Katherine has to say about her story, about finding more about her story.
We’re back with Katherine Kennedy, and we’re going to open up right away, but if you’re just tuning in, please go back to the beginning because there has been nugget after nugget, maybe half a dozen nuggets that have already—the wisdom that comes from Katherine—she’s just naturally herself. Phrases pop out and I’m going, “Yes, that’s so great.”
So, let’s move on. You’ve got a book, Speaking to What Matters. Tell us about the book, and I know you mentioned earlier what it was like to come to write it, but anything else you want to say about the book itself?
(17:26) Katherine Kennedy: Well, I think so many of us don’t believe we have a story to share, and if we think we have a story to share, we’re afraid to share it. Everywhere you look, it’s just a lot of fear around sharing your story. I’d helped so many people share their story through this work at Summer Search, which was a beautiful two-decade career.
But I left at a moment in my life, in my early forties, where I knew that I needed to develop myself. I had this opportunity. I had learned all these skills. I had done really good work. My kids were on the precipice of going into high school. I’d done work in my marriage and I just felt like it was time for me to repot myself and grow.
So, I became a storytelling coach and helped people mostly on stage, actually, share their story, and also prepare for interviews, and ways to use their voice, and talk about who they are, what they do, and why they do it.
In 2020, around when COVID hit, my husband had just finished a year of colorectal cancer treatment, and my father was dying from pancreatic cancer, and it was a very hard year, but it was such a rich year.
It was one of those years, one of those moments, extended moments in life where everything was crystal clear about what was important, right? When COVID hit and, in my own circumstances, time opened up, I recognize and I’m very grateful for that COVID was a chance to slow down and quiet down, and I understand that wasn’t the case for everybody, but that was for me, and I decided to use that time as a way to sit down and, in a way, walk the walk.
I’ve always believed that everyone has a story. I’ve always believed that the work that I’ve done in my own life, and in my own family life, and with my relationship with my father was something to be so proud of, but he was dying, and he died in May of 2020. That summer, I started working. I had actually written my eulogy for him while he was still alive, and I shared it with him, and that was so incredibly powerful.
But when I started my coaching business, I started working on my own writing because again, we think we don’t have a voice. We don’t know what to say. Oh my gosh. When you sit down to write—I didn’t dream of being a writer all of my life, but to sit down and write, that’s another muscle that needs to be built. That takes time and that takes confidence building. Let me just say.
So, it was in 2020 though, that I took the time to work through my fears and tell the most honest version of my story that was possible, which was my story of learning how to open up and to be honest with others and be more real. So, I’m so proud of it.
(20:17) Doreen Downing: Learning to open up, be more honest, and be more real. There’s that “with others” but it starts with yourself. I think this is what I got.
(20:28) Katherine Kennedy: Yes, and that work of mapping out my story, telling my story, going deep into my story was just the most incredible experience. It’s a short book. I set out to write a short book. But for a while, it was just a Google doc, and I shared it with my husband, and I shared it with my sister, and I had the courage to share it with my mother, and my brother, and there were these rich, deep, honest conversations about what happened, and what it all meant, and how I felt, and how they felt.
It was beautiful because I didn’t set out to write—I didn’t throw anybody under the bus. But to share your deepest, most honest, true story of the person you are and the person you’re becoming just is a scary venture, even regardless of content.
So, I did share it and we had these amazing conversations and then I tucked it away. Because while I was writing it, I hoped someday I’d have the courage to share it as a book, but I just wasn’t sure, and I felt like what I had done with it opening up these deeper conversations with the people who mattered the most to me, it was enough.
But then about a year later, I thought, maybe it’s time to actually turn it into a book that’s of service for others. And so, I had to work through my own fears and self-limiting beliefs that what I had to say was good enough for quote, unquote, the public.
As I said to my mother right before it was published, “The public could mean three people, mom.” I have no idea how many people are going to read it. Well, I’ve been so gratified by the way that it’s rolled out and the way it’s been received by many, many, many, many people, so I feel so lucky.
I turned it into a book. That was the same story that I had written early on, but it’s written in a way to tee somebody up to be inspired to tell their own story. I feel like when you read my story, you will know actually a framework, you would be given a model on how you could tell your own story.
(22:23) Doreen Downing: Well, I think you must have a place where people could actually, other than the book, also to get the book to learn how we can tell our story, but you must have a workshop or a website.
(22:38) Katherine Kennedy: I do. So, actually Lee from Speaking Circles, he asked me, Doreen, “The launch, are you going to do a book tour?” And I said, “Oh, I don’t know. But what I really want to do are circles where people read the book and I do a workshop and facilitate a discussion for people to share their own story.
So, I’ve done these beautiful workshops where people share their story. That’s one thing I’ve been doing. I’ve been teaching a writing course. I’m now on my 3rd writing course. I can’t believe it. I’m starting one this fall on October 2nd.
(23:12) Doreen Downing: You mean teaching?
(23:13) Katherine Kennedy: I’m teaching a Zoom class and I did two in the spring that were just incredible. I have another one starting up in the fall and then I did a retreat in the spring and I’m doing another retreat on November 14th and 15th, out at Stinson Beach. So, people come to my retreats and workshops and the class who want to learn how to tell their story, who want to write, want to share, want to go deeper, want to get more connected to themselves. They want to do that inner work that you’re talking about in a safe container.
It’s been a beautiful thing. I’ve joked with people; I had no strategic plan with the book and it has far exceeded any hope or expectation I could have hoped for. I’d insisted to people for 30 years that when you share your story, you can change your life, and it has changed mine. It’s brought me so much closer to so many people in such an honest and real and authentic way.
(24:11) Doreen Downing: Honest, real, authentic. There you go again. And you’re such a testimonial for your own work. I do want people to look you up and I do want people to take advantage of these circles that you’re talking about, but I also want to give people at least, you said that there’s a way, there’s a process, maybe if you just tell them what the first step is. Anything you want to say about the process, but I don’t want you to give it away because I want them to come to you.
(24:42) Katherine Kennedy: I understand. Well, I think the first step in sharing your story is to—every story has a beginning, middle and end, and we’re all overcoming something. I do believe that. We have to be honest with the challenge. We’ve all had many challenges in our life, but the deepest struggle that you experienced growing up, to be honest with yourself, as you paint a picture of your own upbringing, and you do this work and therapy, Doreen.
(25:12) Doreen Downing: Yes, but it is looking, it’s turning around, and looking at yourself with curiosity, but not going at it with a hammer or a chisel. You just want to say, “Oh.” I like what you just said. Ask that question. What was the most—
(25:29) Katherine Kennedy: The deepest struggle. The hardest.
(25:31) Doreen Downing: The deepest struggle. The hardest struggle. I just asked myself that and came up with a different answer, so it’s good. When you sit with yourself and have a good listener like you in a space to drop down, drop in, and go, “Oh,” and you get a little emotional about it too.
My mother was a borderline and I don’t talk about that much at all, so you just gave me a little something I’ll get to work with now.
(26:01) Katherine Kennedy: And all that came from the challenges that you experienced, the choices that you made in response to that deep challenge, the choices you made over time, Doreen. Some of the choices you’re going to look at, that you’d say, “Oh, I’m so proud of myself for that choice,” and other choices, you’d say, “Oh, that was unfortunate.” Yes.
(26:22) Doreen Downing: That’s a kind way to say it. Unfortunate.
(26:26) Katherine Kennedy: But over the course, my guess is, what I have learned, and what I have noticed, and what I’ve helped people see over the course of your life, get to see the choices that you’ve made in response to that deep challenge, and without fail, there’s an upward trajectory of learning and growth. Without fail.
We are hardwired to find the redemptive story, to find the story where we were changing and we’re growing. And we learn, if we don’t see it, that we’re stuck, we are given the option to get more self-aware and make a change. It’s storytelling, but it’s deeper than that.
(27:07) Doreen Downing: Oh, it sure is. I’ve just experienced it. The possibility to link some of those. questions that you just said, the challenges where you feel proud of yourself, but also where you’re less proud of yourself, that all links together in a story as opposed to, “Oh, get to the ark and then you get to the—
(27:31) Katherine Kennedy: To the end, and it’s all over, and it’s wrapped up in a bow.
(27:33) Doreen Downing: Yes. No, I love it. It’s just such an organic process that you’re talking about. We’re coming to the end of our time and thank you for gifting me a little bit of what storytelling, the depth, the new way of telling a story is. It seems to me it’s not learning how to tell a story; it’s learning first how to know your story.
(27:59) Katherine Kennedy: Yes. You’ve just helped me, because I think that’s exactly right. It’s not just a 1-2-3, thank you very much. Let’s all go home. It’s how to really know yourself, how to really know yourself, and then show up, and be more of that self with others. That’s what we want. I mean, that’s what I want. That’s what I’ve worked hard to create, and it’s possible for all of us. I do believe that.
(28:22) Doreen Downing: Right. Well, this is full circle. That’s what you said in the beginning. It is possible. So, thank you so much, Katherine, for sharing today with us.
(28:32) Katherine Kennedy: Thank you so much. I’ve loved being with you. Always.
Also listen on…
Podcast host, Dr. Doreen Downing, helps people find their voice so they can overcome anxiety, be confident, and speak without fear.
Get started now on your journey to your authentic voice by downloading my Free 7 Step Guide to Fearless Speaking: doreen7steps.com.
Get started now on your journey to your authentic voice by downloading my Free 7 Step Guide to Fearless Speaking: doreen7steps.com.