From Doubt to Do: Navigating Your Pathway to Possibility

Kat O’Sullivan is an author, speaker, podcast host, and transition coach. She is known for doing the seemingly impossible and helping others do the same. For over 25 years, Kat worked across sectors — corporate, nonprofit, education, and privately owned businesses, providing a roadmap, support, and tools to bring their vision to life. Her new book, From Doubt to Do: Navigating Your Pathway to Possibility supports people wanting to make a significant transition to move toward the future just waiting for them to say, “Hell, YES!” to dreaming big, living boldly, and creating a fulfilling life they will love.

Is there something tugging at your heart, a “calling” that you would love to pursue, but you have doubts about what else is possible for you or your organization? What assumptions or limiting beliefs keep you from making a “Hell, YES!” commitment to that thing that could expand your reach and your impact? My passion is helping you make the shift from impossible to possible and providing a roadmap to help you bring your vision to life, beyond your expectations.

1. I am a professional credentialed coach and Gallup Strengths-based Coach. As an author, speaker, trusted advisor, trained improv artist, and educational entrepreneur, I’ve helped individuals and organizations discover what else is possible for over 25 years. I’ve worked across sectors — corporate, nonprofit, education, and privately owned businesses, with long-lasting results. My experiences as a businesswoman, foster parent, adoptive parent of a special needs daughter, and caregiver to ill parents have fueled my belief that we are all LIVING our legacy, moment by moment and choice by choice. I’m passionate about helping people move toward the future just waiting for them to say, “Hell, YES!” to new possibilities. 

2. Make Magic Happen, LLC is committed to helping others make the shift from impossible to possible. I’ve personally navigated difficult transitions multiple times, providing tangible proof and inspiration. My empathy and clarity around related challenges demonstrate I genuinely understand what gets in the way. 

3. I take a holistic approach with both mindset and practical steps. I’ve delivered long-lasting, transformative results through a blend of mindset, strategic planning, and support. Results for individuals focus on equipping them to find a new or renewed sense of purpose, overcoming doubts about what else is possible, and equipping them to proactively design the next chapter of their lives. For organizations it’s about facilitating a process that shifts mindsets that will allow them to take the organization to the next level with clarity about what they want that to look like and why it’s so important, leading to a “Hell, Yes!” commitment and the new capacity needed to make it happen. 

4. While I specialize in helping accomplished women 50+, my insights are relevant for any person/organization who is at a crossroads, needing to make a significant shift, and has doubts about what else is possible. 5. Website is katosullivan.com. They will have access to pages that focus on my keynote speaking, my books, access to my podcast, and coaching.

More at – https://katosullivan.com

 

The Interview Transcript

Hugh Ballou:
Welcome to The Nonprofit Exchange. This is Hugh Ballou. This is our 426th episode in a little over nine years doing this and we’ve interviewed some great people Today is no exception. I don’t know good people keep finding us and they want to share their wisdom and their experience and some other stuff with you today. It’s a new acquaintance, Kat O’Sullivan. Kat, tell people where you are, a little bit about your background and your passion for the work that you do. Now, before you start, our title for today is From Doubt to Do, Navigating Your Pathway to Possibility. So Kat, tell us about yourself.

Kat O’Sullivan:
Well, I am coming live from Lake Chapala, Mexico. Yes, for sure. So in the middle of the pandemic, my husband and I made this crazy decision to move from the Los Angeles area to Lake Chapala, Mexico, which is kind of in central Mexico near Guadalajara. And my intention in doing that was to figure out what else is possible in my life at this point. Because I’ve done a lot of seemingly impossible things throughout my life. And I began my career in the corporate world in HR, human resources. And, you know, after years of that, I realized it wasn’t really that fulfilling. And more importantly, there were just way too many constraints on what I could do, and how I could make a difference. So I decided to shift into the nonprofit world. And that evolved into a consulting and coaching practice. And along the way, I’ve also served on several nonprofit boards, which I continue to do today. But I know you asked me to share about my passion and how that came to be. So I want to share how that came about, and what influenced my passion today. well, and along the way. So I discovered it at a very early age. Now, I was 14 when I experienced an Up With People performance. Now, little did I know how that would change my life. So for those that aren’t familiar, Up With People’s mission is to give young people a way to make their voices heard through a two-hour performance and along the way to help build bridges of understanding and become lifelong change makers. I mean, it’s akin to like a full immersion leadership program. So joining a cast of 100 youth traveling for a year and staying with host families wherever we went or wherever they were going, became my dream. And again, it was like a transformational journey. So at 16, two years later, I was invited to join their very first high school cast. And the challenge was finding a sponsor. And here’s where some real learning happened, OK? I was so excited about going, but I had to find a sponsor to pay for my travels. At first, it seemed impossible. But then I thought, I woke up and I thought, well, what if it is possible? What am I not seeing yet? And I have to tell you, those two questions can change everything because it’s amazing what happens when we shift our mindset to one of possibility. So imagine this, I’m 16. I pick up the phone. I called NBC Studios and asked to speak to Bob. Now I’m talking about Bob Hope. You know, like one of the biggest entertainers of his time. And Providence took over, because he was there, and they put him on the phone. I share how traveling with Up With People has been my dream for like two years, and I know it’s gonna be life-changing, my chance to make a difference in the world. And when I hear, where do I send the check? I know my life is never going to be the same. So I affectionately refer to that call as my Bob Hope strategy, which is all about starting with shifting your mindset to one, a possibility, having the courage to ask for what you want, and believing you’re going to get a yes. So then it’s all about saying hell yes to the opportunity and making it happen no matter what. And it helped me take on many, many more seemingly impossible opportunities throughout my life. And I’ve since renamed it my hell yes strategy.

Hugh Ballou:
Your hell yes strategy. Whoa. That’s a magic story. And the fact that you did make the call. You said, Bob, I want to talk to Bob. And you went right to, I guess, you went right to the explanation. This is why it’s important. And then you got him.

Kat O’Sullivan:
I did. And being willing to do that allowed me to travel all over North America with this super diverse group of 100 teens. My experiences on the road helped me see what I’m capable of and realize, you know, I can make a difference in the world. It also, along the way, I experienced the danger of limiting labels and the stereotypes and assumptions and lies that go with them. So if I could, I’ll share one of my first host family experiences that revealed that to me, which subsequently has become my passion in terms of challenging those labels.

Hugh Ballou:
Absolutely. We want to tell people who have just come by our livestream broadcast, that this is The Nonprofit Exchange. You can find this episode at thethenonprofitexchange.org. You’ll find this wonderful episode, and if you don’t catch all the things she’s saying, there’ll be a transcript. so you can go back and pick up some of those gems that you’re going to hear. So, Kat, I can’t wait to hear this.

Kat O’Sullivan:
It’s an amazing story. And like I said, it’s influenced what I’ve been doing since. So this is my very first host family experience. And it completely shifted my perspective. So picture this, two white chicks from middle-class families spending five days with an African-American family in the deep South. And when we arrive at their home, we’re thinking, oh, my God, are we in the right place? And, you know, Carla and I are beyond nervous. We’re kind of terrified because we’ve got all these labels and assumptions about this part of town and what the experience is going to be like, which was not a pretty picture. So we show up day after day, after a long day of rehearsals and school, and we’re like running on empty. And what do we find? A meal waiting for us. And they tell us, oh, we’ve already eaten. But we know it’s not true. They’re giving up their dinner for us. Then there’s Grandpa, who’s sitting in his rocker, smoking his pipe, rocking back and forth in his world. He never joins in on any of our conversations. And to be honest, I’ve already secretly labeled him disinterested or maybe even unfriendly. But when it’s time to leave, he stands up. He surprises us all with tears running down his face. He gives us this big hug, and says, thank you, girls. And I’m like, for what? And I’m stunned when he says, I didn’t think anyone would want to stay with us. And, you know, in that moment, every label, every stereotype that Carla and I had carried with us into that experience shattered, because this wasn’t a family mired in poverty. It was a family rich in kindness and humility that redefines generosity. And, oh, by the way, I realized Grandpa had made some assumptions about us, too. You know, it was very humbling. It was a transformative experience that forced me to confront my biases and challenge those labels. And I walked away with an entirely new perspective.

Hugh Ballou:
That’s amazing. You know, we do have we all have biases. But in the non-profit world, we have myths that we tell ourselves. And I’m guessing, so do you have a copy of your book there?

Kat O’Sullivan:
I do.

Hugh Ballou:
Do you want to hold it up and show us?

Kat O’Sullivan:
Sure.

Hugh Ballou:
So, From Doubt to Do. So, we have a challenge from the very beginning because the word non-profit is a lie in itself. And it puts us in this scarcity thinking. So let’s unpack some of the stuff that you said. We’re not willing to ask people because we don’t want to bother them. We don’t talk about money because we don’t like asking for money. But, you know, we’re giving people a chance to connect their passion with our passion. And the bottom line, we’re doing the work. They’re writing a check.

Kat O’Sullivan:
Well, yeah, I mean, I’ve always said, I’m glad you said it, not me, that as nonprofits, you know, we have this kind of scarcity mentality and fear, you know, around asking for money. But I learned early on that when we don’t, we’ve robbed people of the opportunity to join with us in whatever our passion and purpose is.

Hugh Ballou:
I want to note this, you heard it right here. You’ve heard this before for our audience that’s been here before. You’re hearing it unprompted. In our stage, my wife and I donate to several charities, and there’s joy in giving. And we forget that. So you took a step of faith. you approached somebody you didn’t know, you were very clear on your message, and you said, this is what it’s gonna cost, and he said, okay, where do I send the check? Instead of saying, oh, good luck.

Kat O’Sullivan:
Yeah, and you have to know, it was an immediate yes from Bob Hope. It wasn’t, well, let me think about it. He said, here’s the phone number for my secretary. I’ll let her know that you’re calling, and she can find out where to send the check.

Hugh Ballou:
Love it.

Kat O’Sullivan:
I mean, you know, we underestimate people’s desire to be of service, to help. And, you know, I knew that Bob Hope, you know, was familiar with Up With People. He had emceed an NBC special with them, which gave me the idea. But, you know, a lot of people have ideas but never act on them. Or, I have to be honest, all of my friends and family told me I was crazy. There’s no way Bob Hope is going to sponsor me.

Hugh Ballou:
Well, isn’t insanity a prerequisite for doing this work?

Kat O’Sullivan:
It is. I mean, honestly, it is. You’ve got to be willing to set your preconceived ideas aside. And, you know, I’ll never forget one of the nonprofits that I worked with as a consultant and coach when, I mean, they have an amazing mission. And when I started working with the leadership team, They were, you know, their budget was about $200,000 a year. And I’m like, are you kidding me? With what you are doing, you’re only expecting $200,000 a year. You should be a million-dollar nonprofit. And I have to say, initially, they thought I was crazy. And I will tell you that they now have a million-dollar plus budget because they were willing to rethink, you know, and to consider what else was possible, you know when they asked for what they needed.

Hugh Ballou:
There’s a leadership book by a couple, Benjamin and Rosamund Zander called The Art of Possibility.

Kat O’Sullivan:
Oh, yeah. Love it.

Hugh Ballou:
Yes as a music conductor myself, I relate to that but it’s not about me. It’s about the possibility of Empowering people. So let’s let’s talk about the why what’s the purpose? Why did you write the book? and the book is from from doubt to Do and Why Did You Establish you said you left corporate America, but you established a business but your book is just part of that So, why did you do both of these? Why did you do the book first?

Kat O’Sullivan:
well, so I mentioned that when COVID hit, you know, everything came to a halt. And I realized I was completely burned out, completely burned out. I wanted to do something different, but it felt impossible. Here we are in the middle of, you know, a pandemic. But my husband and I made this amazing, courageous decision to move from Los Angeles to Mexico. So financially I was in a place where I had more wiggle room because in LA, especially in the middle of a pandemic, limited resources and a very high cost of living. So moving to Mexico, it allowed me to take a breath. to be able to think about what I want to do next. And what I realized is it was time to finally write my book. Because for so many years, people have said, oh my God, you have so many amazing stories. You need to write a book. But of course, I was always oh so busy. So, you know, it gave me the chance to deeply reflect on what were the things that allowed me, starting with that Up With People experience and many others, you know, what allowed me to take on what everyone else thought was impossible, do it successfully, And, you know, what were the specific things that contributed to that? So I wanted to share, especially at that time when so many people were facing the seemingly impossible because of the pandemic, you know, to give them not only inspirational stories but also specific tools and resources to be able to step back and do the same thing. Think about like, what is important to me? What am I passionate about? What could I be doing? What do I want to be doing? And if there were no constraints, you know, like if I knew I couldn’t fail, what would I do? And how would I do it? And so that was the impetus for my book. And since then, I’ve had a lot of opportunities like this to share. And so I’ve been able to expand my reach, expand my impact, and talk about the things that are most important to me now, which goes back to the whole issue of challenging, limiting labels and everything that goes with it. to make sure that people get unstuck from those and are willing to pursue what else is possible.

Hugh Ballou:
Let’s talk about your business. How does it help people? And how do you bring value to the world? And who do you bring value to? So your business, what does it do for people? And then who needs you? Maybe you have a story of some progress that somebody’s had.

Kat O’Sullivan:
Yeah, I mean, people are facing a significant transition in their lives, you know, in the world that we’re living in today. And many of them, you know, are burned out. And what they’ve been doing has lost its meaning, or maybe it’s just no longer available to them. and they have doubts about what else is possible. So they also, there are also many of them like us, are looking back and they’re wondering, what is my legacy gonna be? And to that point, what I wanna ask your audience is, how many of you woke up this morning thinking, I’m gonna live my legacy today? Have you ever caught yourself daydreaming about the legacy you’re going to leave someday? And the reality is, it’s happening now. No matter what we’re doing, it’s not something for the future. It’s something that we’re living moment by moment, choice by choice. So we’re all creating our legacy now by who we are, how we live our lives, and the impact that it has on us, our loved ones, and others. So, you know, the business that I’m in now is really for those people who want to make a difference, who are trying to figure out what they want their legacy to be. I say, like, what if this is your moment? a once-in-a-lifetime chance to shatter limiting labels and the deceptive lies that go with them, and create a revolutionary new label? A label that reveals who you truly are, which is full of potential.

Hugh Ballou:
Oh, of potential. Isn’t that a great perspective to have? So we have time for just a quick story. Do you have any story of how it’s impacted somebody’s life, or your work?

Kat O’Sullivan:
Yeah. I mean, I guess the thing that got me into the label-challenging front was when I went to work for a residential treatment program that was offering hope and a second chance for these, quote, at-risk girls. And they were just one step away from lockup if they didn’t get it together. But what hit me is it wasn’t a second chance. It was a first chance. how can you have a second chance when the only thing that you’ve ever known is one thing? I mean, where’s the choice in that? So I decided to challenge the traditional methods and, you know, really take on that at-risk label head-on because it oversimplified the girls’ stories. It discounted their individuality. It created a stereotype that kept them stuck. questioned what they were capable of. And what it didn’t do was inspire change. It just bred resistance, and resentment, and kept them stuck. So I saw this new opportunity. And when I told my boss, he said, Kat, you’re either on something or onto something. Which is it? So my idea was to get these girls out in the community volunteering, and doing some meaningful work. And he was like, you know if you can get enough nonprofits to say yes, We’ll do it. And we did. I found 20 nonprofit leaders who had the vision and the courage to partner with us for a summer-long program. And midway through, we had probation officers calling saying, why aren’t these girls AWOLing? I’m like, I’m not sure that’s the right question. But the reality is that these girls discovered that they mattered to somebody and somebody mattered to them. And it shifted the girls and the community’s perceptions from at risk to full of potential. And there was no turning back. It completely shifted my focus. And I was able to create many more programs that led to other opportunities for underserved youth in the community and, you know, confront those labels that are not just transformational, but revolutionary.

Hugh Ballou:
Love it, love it. So, speaking of that, we’re going to go to your website. And your website for people who are listening to the podcast is your name. Kat O’Sullivan, S-U-L-L-I-V-A-N, and it’s K-A-T O’Sullivan, just like it sounds. So, here’s your homepage. It says, Make Magic Happen. So, tell us a couple of things that people will find when they go to your website.

Kat O’Sullivan:
Well, I’m known for saying when shift happens, it’s time to make magic happen. So I’m all about helping individuals and organizations who are in a significant transition to figure out how to make magic happen. I’m doing that through my book, through my speaking, and I also have a coaching program available for people who do want to make a shift but don’t quite know how to get over those doubts to do the thing that they want to do.

Hugh Ballou:
Yes, and there’s a tab for each of those things at the top in the menu tab. Here’s the book from Doubt to Do, Navigating Your Pathway to Possibility. What a great perspective and Kat, you’re an inspiration even to us old folks that keep doing the same old stuff. I’m an advocate for changing the words to change behavior, so it’s a change. But you’re underneath, you’re fundamentally helping people shift their paradigm and transforming their thinking. So it’s powerful. So this has been a fast 25 minutes. My golly, you’ve covered a lot of stuff and given us some great material. What do you want to leave people with today?

Kat O’Sullivan:
Okay, I want to leave you with a challenge. So before the sun sets today, deeply reflect on what embracing full of potential could mean for your life and the lives of other people on your path. And then tomorrow, and every day after, set a daily intention aligned with the bold new label and live your legacy, not someday, but right now, moment by moment, choice by choice.

Hugh Ballou:
Do it now. That’s powerful, you were ready for that one. Thank you. You’ve helped us rethink a lot of things, Kat, today. Thank you for being our guest today on the Nonprofit Exchange.

Kat O’Sullivan:
Thank you so much. Have a great day.

Hugh Ballou:
Thank you.