Look For Joy And Possibilities To Break Through Dark Times And Create More Good In The World With Donna Skillman

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LYP 14 | Joy And Possibilities

Even in darkness, we can still create more good. In this episode, Donna Skillman, a lover of life and seeker of experiences, shares her journey and how she managed to stay lit with joyful hope and possibilities despite the dark moments of life. She admits she didn’t believe in self-help, but meeting Darrin Tulley pivoted her belief, and taking small steps allowed her to move forward in her journey. Donna also shares her passion for serving others and why helping kids with cancer resonated with her. She encourages everyone to do good for others because good deeds make things better in the world. If you want to find more joy in the world, feel worthy of opportunities, and believe things are possible, tune in to this inspiring episode. Let’s light up your torch with hope and together, let’s face the dark moments of life.

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Look For Joy And Possibilities To Break Through Dark Times And Create More Good In The World With Donna Skillman


I welcome a former colleague from MassMutual, a significant contributor to Ignite Happy and my book, Live Your Possible, and my friend, Donna Skillman, to the show. Donna describes herself as a lover of life and a seeker of experiences. She defines herself not by titles or jobs yet as a joyous and active participant in her life story. Donna is an avid nature explorer, butterfly gardener, and happiness champion.

She loves any time spent in nature and considers the beach her happy place. Read Donna’s story and her steps to stay lit with joyful hope and possibilities in the face of many dark and challenging moments. This episode is for anyone looking to find more joy in the world, feel worthy of opportunities, and begin believing you are possible as she shared relevant ideas and stories throughout the show. Donna is also passionate about serving others in the world, and her greatest joy comes from spending lots of quality time with her husband, Greg, and her three cats.


LYP 14 | Joy And Possibilities


Donna Skillman, welcome to the show. It’s been a while since we’ve seen each other. We worked together at MassMutual. We were colleagues. We’ve been helping each other out for many years and seeing how we can spark possibilities that bring more joy out in the world. I’m excited to have you on the show because I think there are many people out there that are probably struggling nowadays and have had bad days and great days. You’re going to help us learn how to pull out of some of those dark days and how to keep joy, possibilities and love in the world and keep it alive for all of us to keep moving forward each and every day.

Thank you. I’m super excited to be here. I’ve waited for this day since the day we met because our story has been so eventful in terms of the changes that I’ve had and then the ways that I’ve been able to put some of those things into action. It’s been an action-packed journey that we’ve had. I’m super excited to tell this story and if my story can help inspire anyone else to rise above where they are, then that would be the best thing I could do. I’m very excited to be here. Thank you for having me.

You are one of the stars of the book Live Your Possible that I wrote. You’ve edited and read it a few times. You certainly know the path of possibilities. I think you’re the first one that took the path. I know a lot about your past. I want the readers to know a little bit more about you. I’d like to go back in time a little bit because I know you are a big believer in connection, potentially even synchronicities and those types of things. I remember this cool story about where and how you met your husband, Greg. Would you mind sharing a little bit about that?

I love that story. I’ll always share that story. He’ll be very excited to read this because he loves to tell that story too. I met him very young. I met my husband Greg when I was nineteen. At that point, I was in a very transitional point in my life, which I guess a lot of people are at that age. I came out of high school and realized that my high school persona wasn’t who I wanted to be. This is a theme of other times of my life where I was playing a part of this person who was in all these extracurricular activities and doing all of the things in high school.

When I was leaving high school, I wanted to go somewhere where no one knew me. To re-establish this identity of mine, this newfound like, “Who am I? Who do I want to be? What do I want out of life?” For a series of events, I didn’t end up going away to school. Those series of, at times, unfortunate events led me to Greg. Probably the biggest thing I can say about that is had I not purposefully gone down that journey of looking into myself and pulling out those things that I wanted to be, I wouldn’t have been open to meeting him. Meeting him is the kickoff of the happiest story of my life. It’s like a magical story.

I was working. I was going to college at Palm Beach State, which is a community college here. I was working full-time at Toys R Us, and then I was working in the evening at home for the elderly. It was a rehab facility for folks who were older or had been through some physical surgery, and they were rehabbing in this facility. That was an amazing journey. I met a lot of older people who didn’t get a lot of visitors. I have seen a lot of things. That was a magical time in my life when I was in my zone and making these amazing connections. One night, very early on in the new school year, we had a tropical storm down here.

It was Tropical Storm Jerry on August 23, 1995. I’d been to school all day. I worked at Toys R Us, and then I was working in the evening. I was flooded. I didn’t drive at the time. None of my people could come and get me. My mom couldn’t come out and get me because all the roads were flooded. My buddy Steve couldn’t come to get me. I couldn’t get home. I normally walked home. I couldn’t walk because it was pouring and the streets were flooded. I called a cab. It was maybe the second time I’d ever called a cab in my life, but I had no choice. I said, “I’m in this situation. Can you please send someone to come get me?”

It’s 8:30 and 9:00 at night at this point, and I’m waiting. I called back. I was like, “I have no choice. I have to leave. Please tell me you’re going to send somebody.” They said, “We’ve got someone on the way. It’s just taking a while.” I said, “Okay, great.” I go out, and there’s this pink and white cab that drives up. There’s a guy fumbling. I’m getting soaked because he’s pulled up to the door but hasn’t unlocked it yet.

He will probably kill me for telling this part of the story, but he’s fumbling to get the door unlocked. I’m sitting there getting drowned. I get in the car and it’s Greg. I don’t see much of him because it’s dark. He’s got his back to me and he is driving. We had a long ride home. What would’ve normally been about 5 minutes took almost 1 hour because of the flooding. Waves literally crashed over the hood of the cab. It was super bad weather out there.

He had on a local radio station at the time that was like an alternative music station. I am always fumbling for things to say because I don’t know how to shut up, so I was like, “I love the music you’re listening to. I love this song.” We started talking about music, and that pretty much fueled an amazing chat for the next 45 minutes on the way home. When he dropped me off at my house, he was acting uncharacteristically for a cab driver, I didn’t know it at the time, but in subsequent cab experiences, it’s very uncharacteristic.

He repositioned the cab after I got out to make sure that the headlights were shining on the front door so I could see to unlock the door and get into the house. I thought, “That was kind.” I went into the house and thought about him, but that was it. I didn’t get his name. I didn’t know anything about him. We had this magical little chat. Two days later, I went back to the elderly home to go back to work. There were some of those very stereotypical pink “While You Were Out” notes from the ‘90s. It said, “This is Greg, your cab driver from the other night. I’m not a creep. I’d love to talk to you,” with his phone number.”

It’s this incredible connection. Sometimes when we have these chats with cab drivers or folks that are bringing us around in the world, there are some key messages there. It sounds like you guys are connected on many levels. The one is obviously around music. I know he’s been going through some tough moments. I’m hopeful he’ll be playing music for you again soon.

That’s my hope too. I bought a new sign that says, “Live music,” and I’m going to hang it, going into the room to his office.

Live music is to come for many years. Keep getting well, Greg. I’m inspired by what he’s done. We’ll talk about that later or maybe another episode. I remember when we connected in person in Boston. You and your husband at the time were on vacation. You diverted a day. I asked for you to be on my team and wanted to connect with you to figure out a little bit about you and what you’re looking to do. I got to learn a little bit more about what was going on because there was a lot going on in your life at the time.

I do remember you were guns blazing, saying some things to me about how you didn’t like your job. I was on my own journey, as you probably recall, that I started to have my own awakening and started to do some coaching and self-help stuff. You said something about you don’t believe in the self-help nonsense type stuff too. Tell me a little bit more about what was going on. You had a lot of life events happening and at that point, you weren’t sure where you were headed. We are excited to have you on the team because we were at MassMutual together at the time. Tell me what is going on.

Back to that time, I think like, “He had some crazy patience to deal with me,” because I was a hot mess at that time both from a professional and personal perspective. That was many years ago. At work, it was a mess. I had been moved from manager to manager. I didn’t have a leader. I had people who were watching me. I didn’t have an environment where I felt like I could thrive. I had a lot of frustration and angst about my role and not understanding where I fit in and not feeling like I was supported in any way.

Personally, a few years prior to that, my husband and I had been on an infertility journey for many years for the majority of our marriage at that point. A couple of years before that, we had learned that our last attempt was unsuccessful. We knew about that time, I was in my late 30s and it probably wasn’t going to be in the cards for us. It was accepting that because we didn’t want to spend the rest of our lives chasing something and missing out on the happiness that was here because if you’ve been through anything with infertility, it’s grueling. Three in vitros later, we were unsuccessful. It was a very emotional and trying time for us.

LYP 14 | Joy And Possibilities
Joy And Possibilities: What we didn’t want was to spend the rest of our lives chasing something and missing out on the happiness that was here.

I’m coming out of that, having the job stress be what it is. Eight months before you and I met, I had turned 40, which is that midlife time or what does it all mean? I was evaluating, “Is this what I want? Is this where I want to go?” Obviously, with Greg, everything is amazing, but in other parts of my life, I wasn’t feeling fulfilled.

The funny thing about that is if you asked anyone around me except maybe Greg, everyone would’ve said I was fine, even at work. Maybe I had my issues here or there, but I think anyone that knew me would’ve said, “She’s one of the happiest people we know. She’s always positive. She’s always celebrating. She’s inviting everybody in.” I was that person outwardly, but internally I was a disaster. I was very unhappy. We’ll probably talk more about my mom later, but at the time, my mom was in a very tumultuous state and had been my entire life.

I’ve spent most of my life worried about my mom. I was in a feverish pitch about that and where she was. I’m worried about her constantly, what her future was, what that future meant for me and all of these different things. Turning 40, seeing what that all was about, and then my oldest brother unexpectedly passed away. That brought up a lot of childhood trauma and feelings that I didn’t expect and that I didn’t have that I would’ve expected to have. A lot of feelings that I was very surprised I was having. It all culminated in this ball of unhappiness, insecurity and unhappy time.

When he passed away, I took some time off. I came back to work for a couple of days to get my mind off things. At that time, I got the news that my current manager and my whole team had been laid off due to some org changes. I was the last one standing. I was done. I was like, “I can’t even handle the impact of this. I don’t know where I’m going now.” That’s ultimately what led me to you. It was amazing, but at that moment, I felt like I didn’t have anything left in the tank. I felt like I had given and let it all out.

At work, I was maybe taking things out on work that were personal too. I’ll give it that for sure. You definitely met me at the height of one of the lowest points of my life up until that point. I would say it was probably the lowest point of my life. The subsequent year that I’ve had, which we’ll talk about later, has surpassed that now. That’s when you met me. When you were like, “I want you on my team. I want us to do these great things,” I was like, “I don’t care. I don’t want any part of it. I don’t want to know you. I don’t want to like you. I’m done and I want to move on.” Now here we are.

You’ve gone through much. It’s quite amazing to see where you’ve gone. I have to think that there are many readers that have gone through elements of what you’ve gone through that you went through in a period of a few years that people have either dealt with or tried to cope with. I feel for you, especially on all those fronts and even the events you’ll talk about. I’m quite amazed about how you’ve kept it together.

To your point about when we met, you were guns blazing, yet, it’s important to know that we all have a story. We all bring things that we don’t know where people are coming from. I knew a little bit about what was going on at work. I knew you were frustrated. I knew there were limitations and barriers that were put in front of you.

At that point, why would you want to continue, and how could you trust anybody? How could you trust folks that were trying to give you a vision or a thought? That was something I know we talked about in Boston. I think there was a takeaway from that discussion. We were pretty open. That’s an important thing for readers.

At that point in time, we were working together. We were very direct and open, I think quite authentic, especially where you were at the time and where I was at the time trying to figure out what could be done, what we could do and some of the things that were frustrating at work we were trying to solve.

It’s important that we were pretty direct as much as some people and leaders don’t want to hear some of those things. It’s important as human beings that we are willing to hear those things and we did that. One of the things you took away was the book called The SPEED Of Trust. I finished that book. I remember thinking about my own part and maybe not giving everybody the full feeling of trust in me or I lacked the level of trust.

I was spinning a little bit about the book. That’s why I shared it with you because I felt like you were spinning on different fronts. We talked about other ideas. That’s when you were telling me about the self-help stuff. I encourage you to take one step or a small step and not think about it as this self-help thing.

A lot of people struggle with self-help. As we’ve talked about in the past, it is taking small steps because it is about self-care because even externally, if we’re not sharing our best self, internally, it’s coming out. If we could work on ourselves internally and focus a little bit more on joy, happiness and trust, those are the things that sparked in that conversation. I don’t know if you recall that or if that’s something you took to heart from that meeting. What do you remember?

If we're not sharing our best selves internally, it comes out externally. Share on X

I remember a lot. That meeting was important because I had all these good feelings about you. I didn’t have good feelings about anything. At the time, I was ready to be done and not saveable in many ways and checked out. From that very first conversation, I was very open to your point and very direct about it because, at that point, I felt like I had nothing to lose, like, “This is it. Don’t waste your time with me,” and then you did. I couldn’t understand it at the time. I was like, “Why is he trying?” It wasn’t like you were overtly trying. It was from this place of care about me as a person, not about saving my job or because you wanted me on your team to do this project. It is not because of any of that.

I was getting this sense that you were hearing me and seeing me. That was something that I haven’t experienced a lot in my life and certainly not in my professional life. I was caught off guard by it. I remember even telling Greg and friends, “I don’t know about this guy. He’s different. I don’t know why he’s taking this time with me. I don’t know why he cares.” I didn’t want to believe it because I’d been shown that little, especially professionally. When we met in person that time in Boston, it was important to me to get a feeling for you because I’m all about my gut. My gut tells me what to do. I’m all about those feelings. I’m very squishy in that way. I had to know. That’s what it was. It was almost like an interview of like, “Is this guy authentic?”

“Who was interviewing who?”

Exactly. It’s like, “Is this guy authentic? Is he genuine? He says a lot of the right things, but is it for the right reasons? Is it because of care for me or he needs this person in this role on his team?” Within minutes, I knew that you were authentic because it oozes out of you if you have not been told that or if you don’t know that your authenticity, genuine kindness, and care ooze out of you.

I was immediately at ease and you started asking me questions. I’ve told you a million times that’s your gift and one of the things that annoys me too, but it’s amazing in an annoying way. You ask questions and never let me fall back on an excuse or answer that was maybe not the root of what you were trying to get to at the question or what you were trying to probe in me for an answer. You would keep asking.

I got peeling back the layers of these areas of frustration and different things that I had. It came to the negative where I didn’t want to say this because this was aggressive, but my back was against the wall. There were no more layers. It was at its most raw. I was like, “This is it. This is my problem. This is where I am,” and very quickly, it went from that, “We’re talking about work things,” to now there’s more of this personal element that is affecting this work thing. How can we start to unpack some of that? It turned into this amazing journey. I didn’t want to do self-help stuff.

I thought it was silly. I thought it was all people who couldn’t handle their own stuff or people who were trying to sell a magic potion or things of that nature. You were never any of that. It was this authentic set of questions and suggestions for me to go follow. I’m big about dates. It is many years ago that I sat on Memorial Day in 2016 when I left you in Boston. I went and bought The SPEED Of Trust in the airport on the way home from Boston. I sat from literally 7:00 in the morning until 10:00 at night. I prepared this document called Working On Me. I still refer to it to this day. I read The SPEED Of Trust and another book.

You’d recommended The Happiness Advantage to me at that point too. I started reading that one. I was also doing this working on me. That was at your suggestion because as I was trying to figure out my professional stuff, you were saying to me, “What do you want? What is important to you? What are your values? What do you believe in? What do you want to put out there?” I was like, “I don’t know. I don’t know. I’ve never thought about that.” You were asking, “What are your interests? What are you good at?” “I can tell you all the things I’m terrible at, but I can’t tell you the things I’m good at.” That’s what that document was.

I still refer to it. It’s all the things that I view as my strengths and things that I can bring and offer to a job and the world, things that have opportunities where I can work on them, perceived weaknesses using my terminology opportunities and yours. What are my beliefs? What do I want? What am I looking to do with my life? What do I want to be a part of? What are my non-negotiables?

What are things that, even in a data job, which is what I do for a living, there’s still complexity in what you do for that job? What do you part of in the community that you’re in at work? How are you relating to your leadership teams? How are they relating to their people? How are you relating to your colleagues? Is it a fostering positive culture or is it something that’s toxic? Is that important to me? It turns out all of those things are super important to me, but I had never thought about it until you spurred me on to do so.

It seems that has taken a life of its own the way you talked and you made a lot of different connections at work and how you started to think about all those important things. We often talk about purpose, beliefs and trust. I love that you did the work to pause and reflect, investigate and inspect yourself. I wonder if people say, “I don’t have time. Those are fluffy words.” Those were things that we were probably talking about at the beginning. If you don’t take it seriously, it’s fluffy, yet I know for certain when the words are taken seriously into heart, certainly connecting mind and heart and maybe even your soul, it transforms. That’s something that I’ve seen happen in you over the last few years.

It all starts because you did the work. You did that working on me. You tied into Happiness Advantage, which I love that book and TED Talk because it helped me realize that happiness is a platform for a change. I also recognize, I think at the time I recall some of the work from that is, that Shawn Achor said something like, “To be successful at work is only about 25% of our intelligence,” which is counter to what a lot of people think. It’s about how we show up.

It’s 75% of how we show up and the actions we take. Nowadays, a lot of people are hiding. They’re not stepping in or maybe they’re not welcomed by their manager. Maybe they’re not cared for by the people they work with and their colleagues. It’s important. In having a belief in each other, you talked about beliefs, like what are some things that you talk about and think about as you talk about beliefs? Maybe there were some from the beginning or before you even started this journey. Maybe those changed, I don’t know. I’d love to know if there’s any contrast or anything that’s developed over time.

For me, it’s more about how I want to put out what I believe to be goodness into the world. My fundamental belief is in being good and what being good means. That’s a very broad and general statement, but it’s how do I make others feel valued, heard and seen? How do I bring joy to other people? How do I serve people who have less privilege, are in need and are in crisis? How do I lift people up who maybe need a little bit of a lift? How do I bring this good into the world? How do I foster that? What boundaries do I need to set for myself to keep that good within me? That was part of my struggle before I met you. I knew what I wanted to do and I was a good person, but I didn’t have good boundaries and I didn’t have a dedication to that goodness.

What do I mean by that? You met me as you met me. A good person isn’t going to curse at her new manager the first time she talks to him. A good person isn’t going to annihilate the folks that have come before him in terms of frustration and anger. There are many things that when you’re in this place of toxicity, it changes you. If you don’t have that focus on what your purpose is or what you believe to be prevalent in what the world is that you want it to be, you lose focus of that.

How many times are you having a bad day and then you’re subsequently mean on the roadway or you’re not kind to the cashier at the grocery store? Maybe you’re less patient with your children, spouse or parents or all of these different things. Though it’s easy to do, we’re all human. We’re all going to do that. However, when you let your beliefs go and you allow yourself to get into these routines of toxicity and reaction rather than being intentional, you lose sight of what those beliefs can do for you and how they drive you to be in the world.

LYP 14 | Joy And Possibilities
Joy And Possibilities: When you let your beliefs go and allow yourself to get into these routines of toxicity and reaction rather than being intentional, you lose sight of what those beliefs can do for you and how they drive you to be in the world.

I love how you said the word reaction because exactly what you said when we know what we’re trying to stand for, aligned to what you said, the greater good and some other things. If we’re not thinking about that, we’re not pausing. We’re not keeping a calm mind. People hear this and say, “What do you mean a calm mind?” It’s like no stopping to think, feel, notice and figure out, “If I say this, this isn’t going to disrupt everything.”

It’s probably why I ask a lot of questions because I might not always agree or I’m trying to learn more. I’ll ask questions. To me, that’s a path of being open-minded and curious, which is one of the steps in the book, as you know. You said something that was critical about staying focused and disciplined. What do you do to keep that? What have you done?

You have to work at it every day. As I went through my transformation with you and bought into the fact that I needed help, I didn’t want to let go of that either as a concept before I answer your question. I didn’t want to admit I needed help when I met you, even though it was clear to you. I thought I didn’t need you. I can take care of myself and move on with this. You broke down those walls for me to say, “I need help. What does that help look like to me? What help am I willing to accept? I’m still stubborn. I’m still me.” I’m still all of the things that make me me. How do I accept that help? How do I take that help and incorporate it into my life?

That’s the key to all of it because if you can’t understand what will help you, you can’t understand how to take it forward. You can be helped for a moment, for a day or a month, but if you don’t understand what it means to accept that help and then be able to help yourself with it, it’s never going to last. You say it all the time, “It’s within you.” You always tell me I did all the hard work. I always want to give it to you because, honestly, I’m a product of so much of you and the inspiration, motivation, mentorship and guidance that you’ve given me, yet, I can’t deny that I do the work every single day.

Every day I focus on, “What is my purpose? What do I want to bring into this world? How do I want to be? What do I want my life to be?” That can be as simple as if I’m getting riled up about something. I’m human. I am far from perfect. There’s nothing perfect about me, yet I try not for perfection. I try to be better or good each day. Good for myself, my husband and my family. What does that mean? It means I have to be okay. I need that sense of calm, that peace in my heart and joy to spark my own light. If I want to be a light to others, if I want to bring joy to other people and if I want to serve other people, I can’t do it if my own light isn’t on.

I did do it for a long time. It exhausted and drained me. It created this very unhealthy person inside of a seemingly happy person. Every single day I am mindful of happiness. I’m seeing WGs. I see them all the time, everywhere and every day. Before this show, I found a banana. I see them everywhere. Greg referred to it once and I loved it. It is my happiness reset button. I love that because it’s true because every time I see him, wherever, if it’s outside, a dust ball and some cleaning, wherever it may be, it makes me pause and smile. That pause and smile are intentional and grounding.

From wherever you are, it’s like, “Here it is. I’ve seen this. If I’m still open to it, if I can still see it, even if I’m all riled up about something, I’m still here.” I go for Jeep drives because that’s my peace. I go to the beach because that’s my happy place. I go out in my garden because now I’m a butterfly gardener. I find my peace there. I am going out with Greg. I reach out to friends. These different things that we do that keep me lit and that help keep me solid for the day, week, or year ahead. We’ve touched on where I’ve been in 2022. Without those tools, dedication and many years prior to 2022 of what my life has been, I would not have been successful.

I would not be smiling and sitting here, certainly in front of you, wanting to do this show given where we’ve been, without that toolbox or doing all of those things and making it a habit and a routine to always check in with myself, with the world and to make sure I’m being authentic and I’m not straying off of the life I want to have for myself. It’s not for anybody else. It’s like, “I want to be happy. I don’t want to be this stressed out, crazy, worried and anxious person.” I want to be genuinely happy and present that out.

There is so much there that the readers are probably saying, “What is a WG, first of all?” I love the fact that you call it your happiness reset. It’s one of those things that you’re putting in the front of your mind. You’re actively looking for it and it’s available. I’m with you. I find these one-eyed smiles, called a WG that are out in the world everywhere.

For folks that are following along, it’s a big segment in the book. It’s part of the logo of the icon of this show. It’s cool to think about what you said about we are imperfect. We’re perfectly imperfect. Just like this one-eyed smile, each one that’s found is imperfect. It reminds us all that were unique and there is so much joy to be had if we’re willing to have a happiness reset, calm down and take a look at what’s going on in the world.

It’s a beautiful thing. I love the fact that you’ve seen hundreds, probably thousands, at this point. I love that there are other readers that are also sharing and people are sharing directly with you. You’ve shared some of those as well, which I think is fascinating. It’s truly amazing. You’ve put your focus there. If other folks put focus on happiness, be it this one-eyed smile or other things, other people have shared with me like, “If I see a red cardinal, a penny or feather,” all these other things remind them of people they’ve lost or that the world has their back. We’re not alone. I do recall when you felt like you weren’t worthy of joy. You felt like you were lacking trust.

I feel like this is also giving you a space to say, “No, I am worthy of this stuff. I am worthy of this like anybody else.” It’s important for folks to understand that nobody is perfect. Sometimes, as you mentioned earlier, we have this shell that we present to the world. We need to unmask and take that shell away. We need to be our authentic selves for us to shine and exactly what you said is beautiful. It’s fascinating. You’re giving that out to the world. You’re sharing that authentically without that shell.

You are guarded at times, yet I think the way you’re sharing is much different. One of the important things I want to reiterate is the level of focus that you have to do every day because I want to go back to that for a second. We did some challenges at the beginning. I was the “mentor.” You were the mentee type of thing. We did some challenges together. There were 30-day challenges. That was the start of the future and the practices in the Live Your Possible book, which is the intentional practice action.

LYP 14 | Joy And Possibilities
Live Your Possible: Ignite Your Happy, Authentic Self and Live a Fulfilling Life Rooted in Joy, Inclusion, Love and Possibilities!

There are over 100 of these practices in the book to experiment with, as you know. For the readers, these actions help you connect back to your authentic self. Not to become somebody else, but to realign and reconnect back to being you. That’s what you did. That was one of the wonderful things about that connection. We learned how to step in and take those daily actions, and then we started to build more trust and more belief. You started to see these WG and more joy even when there were dark days and moments, as you shared. Do you recall any of those challenges?

I will never forget the first one. That would be many years ago. I told you in the various talks that we’d had a little bit about my life and upbringing. My childhood wasn’t awesome. A lot of folks, unfortunately, are similar to me in that way that there are imperfections in our parents and our lives. I definitely had some pretty big challenges along my path. I’d love to talk about that and to tell people, “This is where I was. You can come out of it. You can get better. It doesn’t have to define you. Whatever has happened to you in your past, in your current situation and what will happen to you, it doesn’t have to define you.”

That was something that was always in me. I do have a gift for words, whether it’s I talk or write too much or any of that. I am definitely very wordy. I’d always love to write a book. I’d always said, “I’ll do it someday.” one of the things you pressed me on was, “Why someday? Why can’t today be the day?” That morning of August 1st, you sent me a video and said, “You could become an author in 30 days if you write every day for 30 days.”

I’m one who doesn’t back down from a challenge. You probably knew that about me at the time. I was like, “I can do that. I’ll do it.” My answer to you was, “What are you going to do?” You wrote back and said, “I’ll exercise every day,” and because I’m an overachiever and can’t ever back off challenge, I said, “I’ll do that too.” August 1st, a couple of months after having met you and starting on my journey, we’re doing this first 30-day challenge together. I did it. I wrote every single day for 30 days.

Probably the hardest set of things that I’ve ever written in my life was this book that someday I’ll do something with it. For now, it’s been a gift that has been given to me more times than I could ever express. I did end up finish finishing the book a couple of months after, but I did write at least 1,500 words or something every day. I did workout every day. I should have done the numbers before we got on this show. I’m somewhere 2,000 something. I’ve only taken off two weeks. I took seven days off when my mom passed. I took seven days off when Greg was in the hospital. Other than that, I’ve worked out every single day.

You said 2,200.

LYP 14 | Joy And Possibilities
Joy And Possibilities: Whatever has happened to you in your past, in your current situation, and in the future, it doesn’t have to define you.

It’s 2,200 or 2,300, something in that area. It’s been amazing. That’s been a journey in and of itself because of that commitment. Talk about holding commitments to yourself, like that commitment to myself has gotten me off that couch more than you could ever imagine because I sit there and I’m like, “Why do I not want to work out today? Just because I’m tired? Am I going to let that be why I don’t do it?” It gets me moving. I’ve lost a ton of weight. I’ve kept off 60 pounds since I met you. I’m healthy, happy, mobile and all of these things. I have my bad hip. I have all of these things. The gift of that is both physically and mentally, which maybe even mentally is even more of the gift because it did inspire that confidence.

It did let me know I could do things. It did make me feel worthy of your pride. When you told me you were proud of me about having done it and your celebration of that with me, Greg is proud of me and in having done it. My mom at the time, like all of those things that I have struggled a lot with that feeling worthy and stuff. I will talk quickly about the book because I do want whoever reads this to know this part about it. I wrote this book. It’s not like a murder mystery. It’s the story of my life. The story of my life, unfortunately, contains some pretty tough things. Some things that I’ve spent my entire life feeling very ashamed about.

Shame is such a powerful feeling, full of secrecy and degrading of your worth, your value, and feeling like you are worth anything because you carry this great shame. Brené Brown has a ton of great quotes about shame. I’ve listened to some of her talks. Here I am writing this book and at the end of it, through another series of challenges, I knew you were going to read this book. Now this book is full of things that I had never shared with a soul.

Greg knew about the big-ticket items that were in there, but not the details because I was very good about keeping details and emotion out of it. Here I am writing this book with the certainty that my boss, you, this guy that I just met, for all intents and purposes, are going to read this. You’re going to read these things as my boss, friend and mentor. Those are things that have kept me down my whole life, things that were terrible.

The gift you didn’t know you were giving me at the time and inspiring me to write was freeing me of that shame and burden of having to hold the secrecy of it because the moment I put words into it, it became less scary and burdensome. The moment I shared it, now I may have been a little nauseous if you recall the night that I hit send and emailed you that book, but it was also one of the most liberating feelings I’ve ever had. I was like, “This is it. It doesn’t get worse than this. Here it is. He’s going to read it. I’m going to have to look at him in a meeting after he reads this. We’re going to still work together and he’s going to have to do my performance reviews and sign off on things.”


LYP 14 | Joy And Possibilities


I did it. It was a revolutionary moment for me to do that. It wasn’t just the challenge itself and the fact that I rose to that. It was what the challenges were that we did together, especially early on, that I think changed because your challenges started to evolve into Ignite Happy. We challenged each other with big things, not just little things, but big scary things. We both rose to those challenges incredibly.

The key message is that the commitment was there, then each followed through. There was an element of belief in each other and trust. At that point, you sent me that book. I’m like, “How could I not read it?” That would’ve blown another door wide open of someone you can’t trust. At the time, I didn’t know what was in the book. After reading it and I said, “That would’ve been awful if I had didn’t read the book.”

There are a couple of things here. Regarding this, like the mentor-mentee relationship. Anybody that has a mentor relationship, it’s not a one-way relationship. It’s two-way. It’s mentee to mentee. I’m trying to encourage people to stop thinking they’re mentors because we all can learn things. I learned a ton by taking on these challenges. I learned from you about what you were learning and you’d share.


LYP 14 | Joy And Possibilities


I would share back. I had more belief in the fact that I was even committing to myself to do the challenges. I grew stronger in my beliefs. I saw you change quite a bit as a front-row seat to what was going on. It was transformative. I started to believe like, “This Ignite Happy stuff is real.” That was the spark of my own writing. You wrote this book and that was a race to who’s going to publish first. That was fun. It got to this amazing place where, “The book’s out now. This show is here.” There is so much opportunity out in the world about how people could work together, human to human,” and about showing care and being there for each other.

That’s the key point with all that, in my opinion then, and then taking this forward about what you’ve gone through, not only from what you wrote in the book to what you said, 2022 was even harder than that. How did you get through it? Could you tie some of the things that you’ve practiced over the years to help you get through it? I know that you said the WG is one of the big elements. What are the things that helped you get through it? It’s important for folks to understand that you’ve been working at this and it put you in a place to get through it. I’d love to know how you would describe it and what you would say.

It’s pretty amazing. In June 2022, my mother, who I was very close to and also had a very complicated relationship with in many ways, from childhood to adulthood, unexpectedly passed away. When you met me, that was part of what I was wound up about. I was worried about her. She had a host of health issues. She had an abusive husband and many different things. I’ve spent the majority of my life worrying about her and going through scenarios of what’s going to happen, what could happen and how it is going to happen. She wasn’t quite gone when I found her, but the day before, and nothing prepared me for it.

None of the worry, the anxiety I had or the years of joy I stole from myself prepared me for when it happened. That 24-hour period between finding her and losing her was by far the worst time of my life. It felt dark, inescapable and smothering, yet I knew I didn’t want to stay there. To answer your question about what brought me out, what tools I used, and what I recognized when I first started working with you as I was in this place that I didn’t want to be in. I was sad, depressed, angry, frustrated and all of these negative emotions and very few of the positive ones in a genuine way. Over the six years up until that point, I’d been working on myself and working with you and focused on the fact that life is a gift and celebratory.

Life is a gift and life is celebratory. Share on X

I’m grateful for every breath and every moment. Even if it’s the last one, I’m grateful for it. As I sat there in this darkness, I still knew I wanted to find the light again. I knew it might not be now or tomorrow. I knew I might only find flashes of light in the beginning, but I knew that I wanted to find it and it was there. I knew the darkness wasn’t inescapable, which is maybe a different way of saying, “I knew I could get better. I knew that this was not permanent.” I didn’t want it to be permanent. I knew it could be permanent if I chose that, but I knew I could choose not to have it be permanent. I’ve shared a lot of the emotion, pain and terror of it with you has been tremendous.

It’s been such a difficult, at times feeling powerless, desperate and overwhelmed, yet I knew I had to make a choice to come out of it. I did. Over time, I took seven days off working out. I could have stopped and said, “The streak is done. I’m done,” but I said, “No, that’s a commitment I made to myself.” My mom was proud of me for what I did. This is my step back to normalcy. These are my guardrails. I’m going to go back to this as soon as I’m ready because I need that for me. The grief for my mom will always be here, but I needed something for me right now.

LYP 14 | Joy And Possibilities
Joy And Possibilities: My journey has been difficult. I feel powerless, desperate, and sometimes overwhelmed. Yet I knew I had to choose to come out of it. And so I did.

That was it. It started with baby steps. At the time, I didn’t even feel like I could get off the couch. I didn’t even have the energy days to even take a shower. I was in this depressive terrible state. I said, “No, I need this for me. This will be what helps to pull me out.” I kept Live Your Possible next to me. I kept a copy that I’d given my mom that she had started to read before she passed. I kept it in her house up until we sold it. When I would go through the trauma of going to her house, I purposefully kept that bright pink happy cover looking at me so I could look over that and say, “I’ve got happy. I’ve got this. I can do this.” I’m still reeling from that.

Greg started feeling some weird health things going on. Fast forward to now, he is post-op from an emergency quadruple bypass. We’re very grateful that we found it before something terrible happened. That terrible thing was looming. We suspected it was looming a couple of weeks before the surgery. We knew it was looming for about a week. There has never been more terror because he’s my person. As a matter of fact, every nurse or doctor he had, every single person I connected with that took care of him in the hospital, I would say to them, “He is my person. You work with a lot of people. You see a lot of people every day. I need you to know how important this man is to me. He is my everything. As you work, operate and take care of him, you need to understand how special this human being is.”

It was such a terrifying experience. I’m thinking of my mom and how my mom would’ve been because she loved Greg and not feeling the loss of her so much. Now we’re selling her house, which is traumatic and all of these things are coinciding. I don’t think I would’ve made it. I mean, honestly, I’m still going to go to therapy. I know I still have things to unpack, but I knew the whole time I was going to be okay. Greg was such an inspiration. He was positive and optimistic.

That helped keep me positive and optimistic. My positivity helped keep him positive. It was about gratitude. We were grateful to have the opportunity to fix it and have the love story we’ve had. This focus on gratitude and being better. The last story I’ll share because I want to tell it. When we were in the doctor’s office and about to get the bad news that we already knew, we already suspected and knew that he had failed a stress test. We were waiting for the doctor to come in and speak to us. I look up and I see this artwork on the wall.

LYP 14 | Joy And Possibilities  





Joy And Possibilities: We were grateful to have the opportunity to fix it. We were grateful to have the opportunity to have the love story we’ve had.

I’m like, “You’ve got to be kidding me.” I walk up to it and it’s a picture that I could have taken. I’ve taken a similar picture of a one-eyed smile of WG inside of Black-eyed Susans in front of these little flowers. They look like sunflowers. There is the exact same picture I’ve taken in my life with a WG in the middle. Here’s this flower. I’ve never been in this doctor’s office before. I’ve never seen this before. I don’t know this man. I’m in this terrible state of knowing that my person is having this critical health issue and I see it like, “You’ve got to be kidding me right now.” Before that, my mom had sent a sign to us in the room where he had done the stress test. She sent me a sign that she was with the doctor that let me know it was okay.

Even as I’m in this turmoil of this urgency, like everything was very emergent at that time, like, “We got to do this right now,” it was chaotic. I was like, “One thing at a time and focus on it being good.” There’s every chance it could not have been good. I would still like to believe that I still, in those moments, held onto it. I didn’t steal joy from any moment that we had up until he went into surgery and out of surgery. Greg jokingly said to me, “This is what you’ve been training for.”

When I was saying, “I don’t know how I can do all of this.” He said, “This is what you’ve been training for. You did a little boxing thing.” I was like, “You’re right. This is what I’ve been training for.” There he is over there, healthy and happy. We’re about to start a new chapter of our lives together. If there’s ever been any test because a lot of things with self-help are transitory. They’re only as effective as you make them and as when you continue to focus on them.

LYP 14 | Joy And Possibilities
Joy And Possibilities: Self-help is only as effective as you make it. They are only as effective as when you continue to focus on them.

That’s true with anything. Any disciplined activity, it’s only as good as your habitual and ritual of keeping it healthy. The fact that I’ve had all of this time now to create this very fundamental and reflexive, rather than reactive per personality, is a reflex. I’m geared to, “Find the happy spot. Get to a place of gratitude. Feel your feelings. Go through it. It’s terrible. You’re human. You have all of those bad feelings, but come ck and bring yourself back.”

I’m sorry you’ve gone through all that. The experiences have been difficult. You’ve seen some dark times and moments where you probably can’t believe this is happening. You’ve limited how far you were going to let it take you because it could put you in a tough state. I do appreciate that you’re going to continue to have those conversations with other folks. It’s important.

At the same time, I do think having positivity, Greg, your gentle warrior, you worked through having the surgery. There’s something important to that about keeping a level of optimism and hope, looking for the signs. I definitely believe there are signs out there waiting to be seen and noticed, as your mom was there for you.

You found that WG with that flower. That’s something you’ve been doing. It’s giving you a piece to do other things. I know when you left MassMutual, you started to pursue other things. In particular, an area where I think you probably would say you might never have done before with Little Smiles. It’s a place where you’re giving back. You’re doing some amazing work there. It’s incredible what that program represents and what you’re doing there. If you don’t mind sharing what that is and how that’s helped you as well.

Little Smiles has been absolutely an incredible journey. I wouldn’t have done it had I not focused on what those beliefs were. How did I want to put something into the world? What did I want to be and put out into the world as myself? That culminated in I wanted to give back in some way. I didn’t know what that was. I floundered about it as we do. We don’t prioritize things. We don’t do them. I thought about it, put it on the back burner and didn’t ever make it something that had to happen. I did our work together and I started to look at my life. I’m a Shriners’ kid. I had hip surgeries as a kid. Two summers I spent in the Shriners Hospital.

I intimately know what that life is like for those kids. Having had some childhood trauma myself, I know what that situation is as well and without being a mom. I have all this maternal instinct. My niece and nephews get a lot of that and my cats. I had so much of this that I needed to give somewhere. My brother-in-law, Dave, knew that I was looking for something. He said, “I heard about this charity on the radio, Little Smiles. Maybe check it out.” I checked it out. Instantly, I was hooked because this charity does amazing things every day. Their whole thing is to bring smiles to children who need them. I mean, talk about the connection.

LYP 14 | Joy And Possibilities
Joy And Possibilities: Little Smiles bring smiles to children who need them.

Ignite Happy, my journey, Living Your Possible, all of these things and when I read that, I was like, “I know how important it was as a Shriners’ kid.” Being in the hospital, there were kids that I met on that journey who had lived in the hospital sometimes their whole lives. You have these children who don’t know normalcy. They don’t know what a regular day of being a child is, either due to illness or some unfortunate home situation. The whole mission of Little Smiles is to bring smiles and joy to kids when they need it the most. There’s almost nothing in this world I could get behind more than that. I went in. I was like, “This is it.” As my first volunteer opportunity, I was hooked.

I didn’t think I could ever work with the kids because a lot of what we do is fundraising for the programs that we do with our children. A lot of the volunteers don’t work with the kids because, oftentimes, the kids are sick, especially during COVID. It was very limited to all of that. I didn’t think I could do it. Because I’m very emotional, I didn’t know if I was strong enough to witness what these children are going through without becoming emotional. I wouldn’t have wanted to put that on them then I did it.

It was the most rewarding experience of my life with these kids who had cancer, doing arts and crafts with them, singing Disney songs, and having this amazing moment where they were normal. They did have pure childhood joy regardless of the fact that they were losing their hair or going to chemo or whatever the situation was.

It lifted me up so high. I went to my Jeep afterward and I cried for fifteen minutes before I drove home. At the moment, it was powerful. I look at these kids because now I’ve been volunteering with Little Smiles for years and a lot of them are in remission. Not all of our stories are positive, but a lot of them are. You see these kids, and they’re hopeful, grateful, optimistic and all of these things that we lose as adults, these kids who have nothing and are in these terrible circumstances. They have all of it. They’re grateful for every little thing.

You serve them ice cream, and it’s the best ice cream they’ve ever had. You’re doing arts and crafts with them, and they’re having the best day of their lives. It’s this pure joy. To witness these kids who need that joy so much go through it is the most amazing thing I do with my time. I love my service to Little Smiles.

I encourage, especially, as we get older and maybe those who have kids, your kids are growing older and you maybe have more time that you didn’t have, find something. It doesn’t have to be with kids. It could be with whatever you want. Maybe for some people, it’s pets or the elderly. Find that place in you that sparks you and makes you want to help people and bring out the best in other people because I promise you it will give you more than anything you ever give. Anything you give, you’ll get back tenfold.

Anything you have ever given, you will get back tenfold. Share on X

It sounds like it’s firing you up. It’s slowing you down to see what you appreciate and what you’re grateful for, to see that some people have only a few days and certain things are going to be cherished. It’s a great message for all of us to take the time. I know we all say, “We’re going to do that.” We do that when other folks pass or we go through some of the struggles like you’ve mentioned. We slow down. I imagine going forward, you’re not going to stop slowing down to notice the beauty in the world, the things that make you have those happiness resets and every time you see Greg smile at you, the things that we take for granted.

It’s important for us to slow down, see that, cherish it, love it and let people know that, which is powerful. I love that you’re giving back because when we give back, it does reward us. If some people say it’s selfish, like, “No, it’s don’t expect it yet.” We should accept it when it does come back our way. It should fire us up like you, which is phenomenal. I have a couple more questions. What would you say is your superpower?

LYP 14 | Joy And Possibilities
Joy And Possibilities: Find that place that sparks you and makes you want to help people and bring out the best in them.

It is in lifting up others when I see something special in them. I have a knack for looking for the best in people. I’m very vocal about expressing that to people authentically. I’m never going to tell anybody they’re amazing if they’re not, but I do think my superpower is in intuitively knowing when folks may need to pick me up and being very happy to give it to them.

LYP 14 | Joy And Possibilities
Joy And Possibilities: My superpower is in intuitively knowing when folks may need a pick-me-up and being very, very happy to give it to them.

That’s a gift to be able to see that. A lot of folks don’t know maybe the awesomeness that they might have or what they are giving out to the world because maybe there’s a lack of confidence, self-doubt and they don’t feel worthy. Those are certain things that I’ve struggled with and I’m sure a lot of other people struggled with over time. You give so much out to the world. You have a big heart. You’re giving with Little Smiles. You’re there with Greg and your sister.

You’re there with many people in the world. Thank you for everything you’re doing. I hope you feel the love and the support back to you, especially through these tough times. Before we sign off, are there any final words or maybe words that you want to spark someone else to start their journey to know that they can also get through tough times or maybe say, “I could do better?”

There is so much I could say there, but to summarize, it’s to believe in yourself. Sometimes it takes someone else to say it to us. Sometimes it takes ourselves, to believe in ourselves and to know that we can do things. As insurmountable as something may seem, you don’t have to tackle it all at once. You can have faith in yourself. In anything that you want to have, you have to include yourself in that because it is within you to do what you need to do. I didn’t believe it. You had to tell me. You said I can do anything because I didn’t feel worthy. I had all of that self-doubt and all of that.

Believe in yourself. Sometimes, it takes someone else to say it to us. Sometimes, it just takes us to believe in ourselves and to know that we can do things. Share on X

I don’t think people outside would thought that of me. A theme with a lot of people is we outwardly play that we’re very confident and that we can do anything. We’ve got this or that. Inside, it’s a different story. It’s hard for some people to ask for help like me, accept help or even admit to themselves that they need help, especially those that put on this mask of strength, confidence and all of these things. We all need to be told we can do something. We all need to believe that we can do it. No matter what path you take, how you want to get there or what you choose to do, have faith that you deserve happiness and you can make it happen.

I can’t thank you enough for giving me that faith in myself and for making me proud to be me, which is something that is wild for me to ever say. I’m proud to be who I am. I love myself, the people around me, you and the life I lead. I celebrate it. We can all get there. No one is perfect. You don’t have to be perfect every day. You just have to try your best to find what will spark you and go get it, even for five minutes a day. Start with 5 minutes and then get to 10 next month and then 15. Wherever you have to start, find it and go be happy.

LYP 14 | Joy And Possibilities
Joy And Possibilities: No one is perfect. You don’t have to be perfect every day. You just have to try.

Know that happiness doesn’t have to be constant yet. We know we can get back to that place because it’s never far away. Everything you said is great. I, I’m looking forward to reading your book. I know you have some new chapters you need to add based on the last few years in tying it all together. I do think it would inspire folks. You are an inspiration. You’ve been vulnerable. You’ve been openly sharing your journey with u. I know folks can relate to it.

I know people are saying that, “She went through so much.” We all admire you, what you’ve done, what you’re doing, how you show up, how you contribute to the world, how you give back and how you open yourself up to make an impact.” It is rewarding you back. I only hope that’s only good and positive thing for the rest of the time. You’ve had enough to deal with. I am certainly honored that you’ve been on a show. I’m grateful that we’re friends. I’ve learned a lot from you. I will continue. I’m a believer. I appreciate you being on the show.

Thank you for having me. Thank you for all you do to put goodness in the world. The world needs more of you. I’m glad you’re doing it.

Thank you so much.

Thank you, Donna, for joining us on the show. You are such an inspiration for coping and excelling through life’s ups and downs. Let’s all send her a message of love and support for all the good she’s doing in the world and consider practicing some of the ideas coming out of this show. For example, let’s start to be grateful for the little things. I know we say we do, but let’s do it. Take notice of ourselves, our strengths and our weaknesses to connect back to what impacts we want to make in the world.

One of the most extraordinary beliefs Donna shared is to constantly do good for others and good deeds and make things better in the world. What is your greater calling? Think about it and start believing you can make an impact. You’ll see when you pause and take intentional actions, you’ll light up the world around you. Stay focused on your journey and practice specific actions that will help you live out your calling and what you would like to see more out in the world, like happiness and joy from what Donna’s practicing and now she’s putting it back out in the world every single day.

Even consider following in the footsteps that Donna took by following the path of possibilities in my book, Live Your Possible. Her Little Smile story was awesome about giving back to kids in need of a smile and joy. It makes me think I must do more. I know it will fire me up, but it should fire you up. What can you give back on? What mission can you follow? Let’s do something together. In honor of the show, try to see the good in others intentionally and help to bring the best out in everyone we meet. Be your happy, authentic self. Serve others and you will live your possible that was once unimaginable.


Important Links

About Donna Skillman

LYP 14 | Joy And PossibilitiesDonna describes herself as a lover of life and a seeker of experiences. She defines herself not by titles or jobs yet as a joyous and active participant in the story of her life. She is an avid nature explorer, butterfly gardener and happiness champion. Donna loves any time spent in nature and considers the beach to be her happy place. She enjoys any reason to celebrate and loves planning events for any and all occasions.

Donna is passionate about service to others and is honored to sit on the Board of Little Smiles of Florida – a charity with a mission of delivering smiles to kids who need them the most. The charity serves children in crisis – whether from critical illness, physical challenges or who are in personal trauma from domestic issues and homelessness.

For her career, Donna found herself working with data early on and discovered she had a passion for that too. She finds a way to weave her desire to serve others into her analytics career by seeking to make data accessible and understandable for all. She believes in the power of data and enjoys innovating in how data is delivered. She is currently fulfilled and happy leading the Data & Reporting workstream for a Business Transformation project for Driscoll’s.

Her greatest joy comes from her role as wife to her loving husband of 26 years, Greg. Together they enjoy traveling, attending concerts and festivals, Jeep drives, spending fun time with their amazing family and friends and lots of quality time just the two of them (and their 3 cats.)

More To Explore

Live Your Possible