She Became CIO Five Weeks After Giving Birth — Here’s What Changed

[00:00:00] Kevin Rice: Just five weeks after becoming a mom, she stepped into the CIO role. And suddenly the badge of honor she had worn for years, outworking everyone, stopped working for her.

[00:00:10] Deena DePhilips: My relationship with time completely changed. I became interim CIO five weeks after I had my daughter. I was that corporate athlete. I was working 80 hours a week, seven days a week, sleeping under my desk. I definitely crashed and burned. When you’re an executive, there’s really no off switch. There’s three lessons. First, my relationship with focus and discipline. I didn’t have five hours to work on a PowerPoint. I had 90 minutes. It was about getting into that flow state and removing all of the distractions. Second lesson, just to fall in love with fluidity and let go of structure. I say let go our be drag. Last but not least, done is better than perfect. I think motherhood is a launching pad. It’s not a pause. Work is my passion, but my daughter is my purpose.

[00:01:00] Kevin Rice: Welcome to CEOs and ABCs. Real stories from execs who lead at work and show up at home. Career moves, parenting wins and fails, and everything in between. I’m your host, Kevin Rice. Here’s today’s episode. Welcome back to CEOs and ABCs. My guest today is Dina D. Phillips, CIO of Red Robin. She’s a trailblazer in the restaurant technology industry, one of the youngest executives ever to be promoted at her company, and she’s been steering Red Robin’s technology strategy through one of the most pivotal chapters in the company’s history. From simplifying complex IT systems to transforming the brand’s digital consumer experiences, Deana’s built a reputation as both a workhorse and a visionary leader. But her story today is also very raw and real. Just five weeks after becoming a mom, she stepped into the CIO role, and suddenly the badge of honor she had worn for years, outworking everyone around her stopped working for her. In this episode, you’ll hear how she rebuilt her relationship with time, traded perfectionism for presence, and found new ways to lead by empowering others instead of doing it all herself. We talk about burnout, resilience, parenting as a mirror for leadership, and breaking generational patterns so our kids inherit something better. If you’ve ever felt the tug of war between being, being all in at work and truly being present at home, Dina’s wisdom will deeply resonate with you. My guest today is Dena D. Phillips. Dina, thank you so much for being here.

It’s great to see you.

[00:02:30] Deena DePhilips: Thank you. Such an honor.

[00:02:31] Kevin Rice: Why don’t we start by just kind of what does life look like for you today? How do you spend your time and what lights you up these days?

[00:02:38] Deena DePhilips: Well, I spend a lot of my time working, being a mom to a three year old. I became interim CIO five weeks after I had my daughter. And so between the two of those things, there’s not a whole lot of time left to do. To do much more.

[00:02:56] Kevin Rice: Yeah, I mean, I find that right in this phase of life, it’s really family and career and if I can blend in some personal activities, that’s great. But you know, that’s where I get most of my fulfillment from anyways, is really being present for my family and for somebody like you who’s, I guess, what about three years ago, stepped into a CIO role. That’s a lot. That’s a lot of pressure. That’s a lot of responsibility.

And so maybe you could share a little bit about what that transition was like when you moved from a vice president to a CIO at Red Robin.

[00:03:30] Deena DePhilips: When I became a mom, my relationship with time completely changed. It hit me like a freight train and I didn’t know what I didn’t know.

And so I was really trying to juggle this new responsibility and my job and then this new responsibility of growing, of taking care of a human.

And for me, I think the hardest transition was I was that corporate athlete. I was working 80 hours a week, seven days a week, sleeping under my desk. And that’s not an exaggeration. I did that for more than a decade and it served me very well. I was one of the youngest directors ever promoted, youngest VPs ever promoted. I was an interim CIO before the age of 40.

So it working hard served me well when I was younger in my career. And I always, I’m a big believer that hard work beats talent when talent doesn’t work hard.

But then that way of working didn’t serve me when I became a parent.

So I had to, I had to figure that out. And it, it took me probably a good year of finally getting a groove of being a new mom and managing an executive career.

[00:04:45] Kevin Rice: Yeah, I think that kind of workhorse ethic can be a badge of honor, but it also can be a really heavy weight. And I certainly felt it myself. I did the same thing 10 years, working really long hours, traveling a lot. And eventually it did get to the point where I was burnt out and I needed to take some time off. For me, burnt out, burning out wasn’t like physical exhaustion, but it was more of a disconnect from myself emotionally and Then I realized by being disconnected from myself emotionally, I could, I could work really hard, but I was missing a lot of the connection with my. With my family and even with my team at work. I’m curious if you ever got to a point where you did start to feel burned out in a small or large way. And if so, what was that experience like for you?

[00:05:35] Deena DePhilips: Yeah, I. I definitely witnessed from the sidelines. But I remember you and Jesse, and I just remember thinking those guys have been working their tail off, especially with COVID You got all that influx in business. For me, I cr. I definitely crashed and burned. After I had my daughter, I. Like I said, I didn’t. I didn’t know how to integrate being a new mom with this new executive career. And so I just wanted to overdrive on both. I mean, you know what it’s like to have a newborn. I drew the short stick. My daughter is. Been the worst sleeper in the history of the world.

And so that first year was really rough, but you still have to show up for board meetings. And when you’re an executive, there’s really no off switch. It’s kind of like being an on call doctor. You don’t get to really punch out. So. And at the same time, our company was going through so much transition. I mean, we were already in a turnaround of a turnaround after Covid, so we’ve just had a really steep hill to climb. And so to your point, that workhorse mentality served me very well, but I had to figure out really quick on how to adjust.

And I think there’s really three lessons in that. Like, first and foremost, I. My relationship with focus and discipline. I didn’t have five hours to work on a PowerPoint. I didn’t have six hours to analyze an Excel spreadsheet. I had 90 minutes. And when I was doing that task at hand, it was about getting into that flow state and removing all of the distractions. Because, Kevin, let’s be real. Everybody is distracted right now, right? It’s so loud.

[00:07:15] Kevin Rice: We have gotten three text messages already since we started.

[00:07:20] Deena DePhilips: I mean, people laugh at me, but I think I have a thousand text mess, unread text messages. But it’s no doubt. It’s the slack, it’s the team’s message, it’s the text messages, it’s the email, it’s social media, it’s Twitter, it’s Instagram, it’s Netflix, it’s. I mean, our attention is constantly being pulled. And so I had to figure out, you know, when I had it, when I had when I was at work, I was at work and I try to remove every. When I was doing a task, I was doing that task. And so the second lesson in that too was just to love chaos a little bit. And for type A people, that’s really difficult. I say let go or be dragged. So just to fall in love with fluidity and let go of structure. I had to stop thinking that my old life and structure was going to be something that I could really execute in the future. There was no get up at 5am, do a sauna, do red light therapy, work out for an hour, get the kids ready, go to work and the kids in bed by seven.

It just, it doesn’t work that way.

That would, that’d be the second lesson. And last but not least, you know, Sheryl Sandberg said this in her book Lean In, a very iconic book. I’m sure a lot of your listeners have know her or, or read the book. She says done is better than perfect. And again, for type A people. I used to be an inbox zero person. I think I have 20,000 emails in my inbox now. And, and just again, just done is better than perfect. And try to really live by that. I again trying to. I used to analyze a PowerPoint if the font was right and the bullet points were straight and if the title was centered. And now it’s the presentation is more important than the PowerPoint. So just let it go. Right.

[00:09:13] Kevin Rice: Yeah. You can’t let your OCD take get the best of you. I actually, I love Sheryl Sandberg. If anybody’s listening and knows her someday, I would love to have her on the podcast.

[00:09:22] Deena DePhilips: Oh, that would be amazing. You might be able to get her.

[00:09:26] Kevin Rice: So what I think you’re really hitting on is presence. And with an executive career or any aspiring executive career, there’s so much stress, so much pressure and it can be really hard to walk in the door and step out of your CIO role and step back into your family role, your parenting role, your partner role. How do you stay present in the moments with your families when you’re probably still getting slack messages at 8 o’, clock, 9 o’ clock at night, your emails are coming in at all hours of the day. How do you stay present so that you can give your family as much as you give to your career?

[00:10:01] Deena DePhilips: Yeah, and I’d love to hear your answer on this too. There’s a few things so I don’t think it’s possible to be to again that fluidity. There’s weeks where there’s a lot going on at work, and there’s a lot going on in my mind because of that. And so when I’m with my daughter, that’s running in my head. I, I do in that, in those moments, whether it’s an hour, two hours, I do really try to dedicate that this is my time with her, but I can’t stop the thoughts. And sometimes some of my best epiphanies for work have been when I’ve been playing with my daughter on the floor in the living room. Right. And it’s just, it’s not that black and white because our brains can do. Can do multiple things at once.

The one tactic, though, that I really do like to employ is I like to go into the future when I’m 67 years old and I’m alone on a rocking chair in my backyard.

[00:10:59] Kevin Rice: I don’t think you’re going to be in a rocking chair by 67.

[00:11:04] Deena DePhilips: Okay, maybe I’m exaggerating just a little bit. Um, that I would give anything to go back in time and to be in that moment in my living room when my daughter is three, playing with Legos.

Right. I know that we will give anything to go back in time and to be present with our child. And so I really try to put that little scene in my head. So when I’m in those moments where maybe my mind is not with her, it’s on work, I try to think of that. And then maybe the second tactic too is when I. I always just try to make it up. So when there’s a lot of weeks that are heavy travel or board weeks or anything like that, I, I know that I’m not going to be totally present for a good five to six days, but the following week, then I really try to shut it down. And Friday, Saturday and Sunday, it’s all about her. Let’s go to the zoo. Let’s go to the botanic gardens. You know what I mean? And so I try to always make it up somehow. And I, I think being a parent is very much like any relationship is make a lot of deposits in the bank. So when you do have to take some money out, there’s plenty of deposits where she doesn’t feel it.

[00:12:16] Kevin Rice: Yeah, I think that’s a great analogy. It’s something that I’ve heard before and it’s worth restating because, yeah, it’s like a connection bank. And the more you put into it, if you have to withdraw from it, it doesn’t feel like such a rift in the relationship. Whether it’s career or your partner or your kids. And as your kids get a little bit older, they’re more conscious of the connection.

And the more connected you are, the better they listen to you.

Hi, Kevin here. If you’re enjoying this conversation and you know someone else who’s working to grow in their career while staying present at home, I’d really love it if you could share this episode with them. It’s one of the best ways you can help us and help more leaders build their careers in a way that they’re proud of without missing the moments that matter most.

Have you ever had any moments where you’ve had some really intense tug of war between career and family life that you had to choose one or the other? And how did you balance or how did you manage that situation?

[00:13:15] Deena DePhilips: I can think of one. And the turmoil was five weeks after I had my, my daughter, the, the CEO at the time anointed me interim cio. And the turmoil was, can I really do both? Is this possible? But I think that that is from years of, of people telling women that it’s not possible. And I, I, again, I like not to go down a rabbit hole, but I really commend you for this podcast and having just as many men on it as you do women, because I didn’t, I didn’t get it. Well, I had a kid myself where that question is really geared towards only women of how do you do it all? How do you balance it? But they’re not asking my co workers that. So as, as you grow up in your career, as, as a woman, as a female, there are those perceptions that, that exist. They’re very real. And women have to consider being pregnant while having a career, postpartum while having a career, and then managing the newborn after that. For, for me, when I was presented this opportunity, I really was. I don’t, I don’t think I can do this.

But I, I think that was all the noise and I was listening to outside perceptions that just weren’t real.

And like I said, I think motherhood is a launching pad. It’s not a pause in your career. And so I really embodied that at the time.

[00:14:44] Kevin Rice: Men want to play a role and be a part of the family and have relationship, like be connected with their kids. But at the same time, I think if we’re honest, it’s. It’s very different.

Women, as you mentioned, are going through so many more changes, right? You’re, you’re actually growing as human.

You are going through physiological changes that are completely different that men can never experience. So as much as we empathize, we’ll never experience that. And so I can only imagine how difficult it would be creating life and then having to go back to work, just seeing the dynamic of your life change so dramatically.

I guess what I’m saying is like giving so much credit to the women out there. I love having men on talking about being a father, but it is very different.

[00:15:36] Deena DePhilips: It’s funny that you mentioned that because I. When I came back to work too, I felt like I was.

Like nothing was as hard as what I had just been through. But I could challenge, could. I could accomplish pretty much anything. I’m a big believer. And you can do anything. I know that sounds really cliche, but if you put your mind to it, you can figure it out. You can solve the problem. If it’s a challenge, you’re. You can. If you have enough resilience, great. And stamina, you’re going to get past it. But then when I had it, when I created life, I’m like, I created organs and an elbow and eyeballs, which is one of the most intricate parts of the body.

I can. I can get through this meeting. Right.

Like, nothing. Everything else was. Was not as difficult as what I have just done.

[00:16:20] Kevin Rice: Yeah. I’m constantly amazed when I look at my partner who’s actually now my fiance. We recently got engaged.

[00:16:29] Deena DePhilips: Congratulations.

[00:16:30] Kevin Rice: Thank you. When I. When I look at her and how she cares for our son, who’s 17 months old, I’m just constantly blown away. Like, the amount of care and attention and love and connection that she has with him is so, so beaut and so special. So, yeah, I’m just constantly blown away by what women are able to do and life that they’re able to create.

[00:16:53] Deena DePhilips: Well, thank you. It’s a compliment to women everywhere.

[00:16:57] Kevin Rice: You mentioned kind of making the shift of being a workhorse, which I wore that badge of honor for many years to more of a strategist and strategically thinking about being a leader and empowering others. How has that journey been for you? Have you. How has that transition been for you? What’s the hardest part of it? How have you kind of reshaped people see you and how people see you in your career?

[00:17:21] Deena DePhilips: Yeah, I think that’s the. Probably one of the hardest transitions for as you make when you’re escalating up from director to VP to C level. And I think I shared with you, working hard served me very well. But I think it has a rebounding effect as you mature in your career because people, they do associate you with Being the doer, the one that’s going to get everything done. And it, It’s.

I do wear that as a badge of honor. I want to make sure that also everyone hears that I don’t care who you are or where you start from, I. You’ve got to put in the hours in the beginning. Right. You just do that. Transition to being a leader, a thought leader, a strategist, is one of intentionality, thinking about how you’re showing up and that you’re not the one that’s always the anointed getting something done, but you’re the one in the room that has the ideas. And yeah, I would say, or probably to some degree, all or even some of the best executives I know still kind of struggle with reverting back to, I need to be in that meeting. Do you really need to be in that meeting? Hire great people and get out of their way.

And so I think it’s just a good reminder I don’t need to be in every meeting. That’s why I pay really great people to get the job done.

[00:18:38] Kevin Rice: Yeah, Yeah. I struggled with it too. Like, dipping down the leadership pipeline. Right when we started, I was the account executive for every account. I did all the sales, I did all the marketing. Right. And then over time, we built up teams, and then I led the client services team and then led project management.

Ultimately, towards the end of Pathway, I was the president running the leadership team, you know, the majority of the organization. But I’d still find myself dipping down the leadership pipeline because that’s what I was comfortable with. That’s what I knew, that’s what I really where my roots were. And so just because I. I knew I could do it and I felt like, oh, I’m good here. That gives me value or that makes me feel valuable. Wasn’t necessarily the right thing to do because like you said, I’m not trusting the team. I’m not empowering the team. And so I had to make that shift, too, and be more strategic about how I allocate my time. Even when that poll is strong and when I became a parent and when I became a parent of two boys and now I’m a father of three, my relationship with time changed too. I didn’t have the hours that I could put in anymore without sacrificing more than I would be willing to sacrifice for my family. So that shift can be really, really difficult.

[00:19:54] Deena DePhilips: Yeah. And I, you know, when I was younger in my career, I was. I was put in a domain that didn’t have any Expertise in. I was kind of thrown into technology by accident. And so I’ll never forget the person who promoted me. He was the CEO at the time, Steve Carley. He said, all we need right now is a leader. Your expertise will catch up with you. And also I was really lucky to have people believe in me more than I believed in me. And then when they do, the lesson is, is try to try to meet their expectations.

But I had to work really hard because I was the most unqualified in the room and I had to quickly in order to get qualified, in order to, to be an expert in my domain, you just had to put in the hours. But it is very easy to revert back. And it’s just something that I constantly, every single day that I wake up is how am I empowering my people? I don’t need to approve the color of the change on the website.

You guys got it right. Not everything has to be ran through me. And. And so, yeah, it’s a constant journey though.

[00:20:59] Kevin Rice: Yeah. It’s interesting for some reason when you said, when you talked about being the most unqualified person in the room, my brain went to parenting and how when we have a child for the first time, we’re literally the most unqualified person. At least for me. I had no idea what I was doing. How did that same kind of thinking apply to you becoming a new mother?

[00:21:18] Deena DePhilips: Yeah. And I shared this with you already. I’ll share it again because I think about it a lot is especially for the woman on the phone. I don’t believe motherhood is a pause. I believe it’s a launch pad. I became a better person, a better leader simply by having a child. Because there’s nothing more in this world that’s going to make you a better human than raising little humans.

Because you’re constantly reflecting your intrinsic, intrinsically thing about how what you do impacts your child. And you want to be a good role model and you want to be present, you want to be a good listener and you want them to think of you as a superhero. So you’re quickly like, I got to fix some of these flaws real fast.

And that that translates over to leadership too.

[00:22:04] Kevin Rice: Yeah. Kids are like our greatest mirror. If you are constantly picking up your phone or you’re on a tablet, pretty quickly you’re going to see your kids mirroring those same activities back to you with their own toys, picking up a phone, holding it to their, to their ear, or like trying to swipe on a book. And so everything you do like more is Caught than taught. And, and just parenthood is such a great mirror for reflecting on how you carry yourself, how you behave. I’m curious, after becoming a mother, how did that change how you showed up in your career or how you acted as a leader at work?

[00:22:39] Deena DePhilips: Yeah, I think some of the things that I, that I just mentioned is you become more patient, more empathetic, a better listener. You want to be more present. And I don’t want to translate my employees to my kid by any means.

[00:22:54] Kevin Rice: Of course. Yeah.

[00:22:55] Deena DePhilips: But to some degree, you’re, you’re also developing other humans in a different way that you care about. And I would find myself kind of using some of the tactics that I do with my daughter, with my employees. And again, I don’t want that to sound demeaning in any way. It was, it was just, I, I, I was more calm and again, present and, and thoughtful. I, when you have a child, I don’t know, it just like ruptures, you know, there, there’s a rupture that happens that you kind of shed this old skin. And inherently, I think subconsciously and consciously you just want to be a better person and that of that better leader. So those, it starts seeping out in ways and small ways and you just mature. I know. I, I just, you, you have this maturity to you that I think I didn’t have prior to having kids. Now, the last thing that I would say too is I had kids later in life, like much later in life, and I didn’t, I, I couldn’t relate to my employees or my team members that had kids.

They, I didn’t totally get the having to go to the soccer game at 3:00 or Friday, there’s a baseball game that they have to get to that’s five hours away. And, and I became a little bit more sympathetic to that. Work life balance. I hate, I hate the terminology, work life balance. I don’t think it exists. But you know what? I’m, what I’m trying to say. So I also became more relatable to them because I became a parent myself. Things started clicking for me a whole lot more.

[00:24:24] Kevin Rice: Yeah. Yeah. Everything you shared wasn’t about your employees. It was about you. It was about how you evolved through becoming a parent, becoming more patient, becoming more calm, more present. So I agree. Right. This is whether you’re in a work dynamic or a family dynamic, it’s about a human connection that you are creating with other people. And I think that’s beautiful. It’s, it’s something that we all evolve in this journey called life. And parenting is a major inflection point in that journey. So you have a three year old, right?

[00:24:57] Deena DePhilips: Yes.

[00:24:58] Kevin Rice: Yeah. How’s your daughter in that kind of three year old stage? Is she a three nager? Is she still a good listener?

[00:25:06] Deena DePhilips: She is. You know, we avoided terrible too somehow. And she’s not quite hit three nager. She’s still, she’s still kind of that sweet toddler. I, I do have a sense it’s coming because there’s a little bit of sass coming.

[00:25:19] Kevin Rice: Yeah.

[00:25:20] Deena DePhilips: That I see from her. But you know, she is aware when mommy leaves. You know what I mean? And she, there’s sometimes there’s tears, sometimes there’s her wrapping her arms around my neck so tight, knowing that I grabbed my jacket and she doesn’t want me to walk out the house. And I think those are the moments that just crush your soul a little bit. How do you, how do you rip your daughter’s arms off your neck and just get in the car and go to work? And that’s a whole nother battle in itself.

[00:25:48] Kevin Rice: Yeah, it’s really tough. It’s hard. I experienced that a lot when I used to travel for work. If I was packing my suitcase, my kids, they were during this time they were probably about three and a half and two months old, something like that.

And my three and a half year old would see me packing my suitcase and he knew exactly what was happening. And in those days I might be gone for three or four days. And it was really, really hard on him. And it was hard on me because yeah, if he’s sad, crying, grabbing my leg like that, it does it like tears your soul apart. So getting back to like the connection bank, it was really important for me to spend undivided time with him before and after. And there were during that period I probably wasn’t great at it, but it was something I learned to do later on in my care career was that even if I couldn’t be with them for multiple hours a day, like I wanted to, 30 minutes of really good quality connection time doing something that bonds us was better than a couple hours of me being distracted thinking about work. And so today I really do try to focus on giving presence. Right. There’s like quotes about presence being the greatest gift you can offer somebody. That’s why they call it present.

I try to purposely plan my personal life as intentionally as I would plan my career. And so my career crazy. Scheduled calendars, color coded events, time blocks. I try to apply the same kind of thinking with my kids. So when I look at my personal life, I’ve got time allocated for different activities that I feel like bring us different value, whether they strengthen our family values, whether they’re building connection, activities that might be building resilience. So I try to be more intentional about the time, recognizing that I’m never going to have, or at least right now, I’m not going to have as much time with my kids as I do in my career. And as long as I’m intentional with it, then that time can be really valuable and worth more than distracted time.

[00:27:47] Deena DePhilips: Perfectly.

[00:27:48] Kevin Rice: I think one of the things our listeners really love to hear about and understand is if there are any things that you do to create rituals or routines that help you show up in both places, whether it’s in your career or at home, with more intention and more presence, I’d love to hear anything that you do in that area.

[00:28:08] Deena DePhilips: You know, when we talked about the letting go of structure and kind of falling in love, falling in love with chaos, that means that there’s not as many rituals as there used to be. Yeah, I, I would say our rituals are just making sure that when, when I get home from work, that we have like an hour and a half, two hour window before she goes down to bed for bedtime. And for me that’s, that’s really difficult because I’ll walk out the door at 8 or 9 in the morning and then I don’t see her again till 6pm and then I only have two hours with her at night. So trying to capitalize on those two hours before bed. And you know, you said something when we were talking about your, when you asked how are you present? I think it’s a really important. What you called out is putting the phone away. Like I don’t need to see any more screens. When I get home, if something is a 911, someone will know how to get ahold of me. But putting away the phone, turning off the tv, eating dinner together, we’re not always great at it, but really just trying to be together as a family. Go to a park, hang out, go in the backyard. And that is, it’s not the sexiest ritual, but it’s the ritual that keeps me really connected to my daughter. At least Monday through Friday.

[00:29:21] Kevin Rice: Yeah, well, and what you mentioned about when you look back and you’re in that rocking chair at a 120 years old, you’re. You’re gonna wish that you had like five more minutes in the backyard or reading to your daughter, putting her to bed, you’re not going to be thinking about, oh, I wish I would have spent a little bit more time preparing for that executive board meeting presentation. So just always keeping it in perspective. I think maybe that’s a lesson is that, like, perspective can really help you get into presence.

[00:29:51] Deena DePhilips: I love that. I love how you said that.

[00:29:53] Kevin Rice: I read to both my kids before bed every night. We were not great with dinners. I’ve heard a lot of guests talk about how dinners are a really strong ritual and routine for us. Dinners are kind of messy. I’m making dinner while putting dishes away, while cleaning the kitchen. We’re eating in different areas at different times.

It’s not that, like, family dinner that I grew up with. We’re really good about breakfast, but our routine happens right after dinner and that’s when we usually play. There’ll be some, like, wrestling or pillow fighting. And then there’s always reading. Every night, at least Monday through Friday before bed, I’m reading a certain book with my middle son. And then when he goes to bed, I’m reading another book with my oldest son. And that’s been a really strong ritual and routine. And I’m hoping that it will create a love of reading and learning for them as they get older, too.

[00:30:44] Deena DePhilips: What someone said to me, bedtime is a sacred time because there. I think that there’s a set of parents that definitely dread it. And for me, I don’t dread it because, again, I don’t see my daughter the majority of the day. So I look forward to it, even if it ends up being longer than I love. But you said bedtime is a sacred. Sacred. I really took that to heart.

[00:31:08] Kevin Rice: I know you’ve described yourself as a very driven leader. And one of the things I think about is how I’m often really giving my children a lot of comfort, things that I didn’t have as a child and giving them a lot more opportunities. But sometimes I worry that that might strip them of the opportunity to actually learn how to work hard and learn how to be resilient. How do you think about your children and helping them learn to adopt? The same kind of work ethic and drive and pursuit of passion that you’ve had without stripping that away by giving them too many comfort.

[00:31:47] Deena DePhilips: Yeah, I. I don’t know if I have a perfect answer, but I do think about that a lot. I grew up very, very, very humble beginnings. Foster care parents are. Were addicts, very bad situation. And so I. I try to think, am I overcompensating with, With.

With my daughter? Because I never Ever want her to feel anything that I felt growing up. And so I don’t. It’s. It’s on my heart and it’s on my mind, and I haven’t quite figured it out, but I do. And I think almost a lot of your podcast guests are probably saying a different version of the same thing. We work on a regurgitate version of this, but I think I’ve heard this a lot on. On your show, which is the role modeling that takes place.

Their mom or dad is working hard, getting up, going to work on that computer.

I hope I’m role modeling for her that you do have to work hard to get things in life, and I want her to be proud of that. And especially when she’s. She’s only three. Right. But as she gets older, I really look forward to her asking questions about what I’m doing and why am I working so hard. And for that conversation to spark an interest in her that she has work ethic, too, as she grows up.

[00:33:09] Kevin Rice: Yeah, I appreciate you sharing that. I think you are a great example of overcoming early childhood challenges and trauma. Both my boys haven’t seen, or at least my two oldest haven’t seen their biological mom for four years because she struggles with alcoholism.

And that’s why I became a single parent back in 2020.

Covid happened the way was doubling in size.

My world on the outside looked really successful, but internally, like, things were falling apart and it was incredibly difficult. So I think a lot about at some point, Levi and Liam, are they’re going to have that fork in the road, too, where they’re going to have to decide, are they going to let those circumstances of their early childhood give them an excuse to be a victim of life, or are they going to use it as, you know, springboard to overcome and be resilient and make something of themselves? Did you ever have a period where you were growing up where you thought about your childhood and how that made you aspire to be who you are today?

[00:34:16] Deena DePhilips: Yeah. You know, so first of all, to the alcoholism, I think it’s the worst drive out there, and it’s too accessible. So apologies. I’m just so sorry to hear that. I believe you are who you are because of your choices, not because of your circumstances. And for me, growing up, I just knew I never wanted to live that kind of life. I needed to get away from everything that was associated with drugs and alcohol and carve my own pen, which was breaking generational curses more than anything. I mean, I don’t drink. I’ve Never been drunk in my life. So I think for Liam and Levi. Is that right? Yeah. Hopefully they. They also maybe have witnessed something that it changes their perception of with their relationship with alcohol when they get older. But yeah, I think when you live that kind of life, you do everything in your power to make sure that you can change your trajectory, which includes changing your future children’s trajectory.

[00:35:18] Kevin Rice: Yeah, yeah. Generational curses. Generational trauma. Right. It’s really interesting when we look back at past generations now, you see how these things are just consistently passed down.

And I think this time period or our generation is really the first to think about, like, making those changes and it will cascade through our children and their children.

[00:35:41] Deena DePhilips: Yep. Yeah. Well, and going back to your. Our comments about being a workhorse and working really hard, I think for me, that burst out of wanting to be. Become more than what I was and making sure that there was nothing in my. In my adult life that I could never experience what I experienced when I was a kid. So in my head, I was just. I just have to work hard enough to get, get away from all of that.

[00:36:09] Kevin Rice: Yeah. I think where it hit me, and I recognize this isn’t a super relatable story for a lot of people, but I took a couple years off work after Hathaway was acquired, and during that time, my kids didn’t see me be productive at all. Right. Like, I, I was. I mean, I was around. I was full time parenting. Right. So that’s super productive. Not trying to downplay that, but they didn’t see me acting in any sort of like, professional capacity.

And I realized that they’re. They were so young when I was working long hours and when Jesse and I were building the company that I was like, if I keep doing this for another 10 years, these kids are going to grow up and they will have never seen me actually work and pursue something. So when I look back, I saw my dad work really hard in his career, and obviously that left an imprint on me and I worried and I wondered, well, if I continue to take time off, what’s that gonna show them? What’s that gonna tell them about the world? All they’re gonna ever see is me being at home. I was playing a little bit of golf at the time, but you know, what, what would that show them as they grow up? And so that was part of the reason I wanted to get back into some career activities. I started doing investing, I started doing advisory work. Now doing the podcast, which has actually really been a good checks and balances for me because the whole spirit of this podcast is about balancing or showing up at work and showing up at home. And so it constantly reminds me that I have to keep that balance and I have to stay present in both areas. But one of the reasons that I started getting back into various ventures was because I wanted my kids to see me and I wanted to inspire them to pursue their own passions and go out and build something for themselves.

[00:37:56] Deena DePhilips: Yeah. Well, I saw one of your boys was doing the lemonade stand and really put in the work for it, and I loved it. Very cool.

[00:38:05] Kevin Rice: It’s so cute. He, he’s probably made easily $500 doing his lemonade stand and built all kinds of LEGO projects as a result of it. I do think too, by making his own money, we went to buy a LEGO project. He had made a hundred bucks. After a few days, went to the store and he realized how small a hundred dollar LEGO project is. And it really helped him click in the value of money. He’s like, why is this so expensive? Like, why can’t I get that big project? This is $100.

And so he’s starting to understand the value of money a lot younger and it’s kind of like changing his relationship with money. And he’s willing to work for it. He. He’ll be out there for five hours selling lemonade.

[00:38:51] Deena DePhilips: That’s amazing. I think we can all remember that first job where we got that money in our hand. I worked at a laundromat.

I, I think I. This is back in the day I had child labor laws. I don’t know, but I was 14 maybe. And then I realized money does equate to freedom. And so again, going back to that, if you work really hard and you get more money, you can, you have a little bit more freedom and you can get the things that you want to get. But that moment for him on making $500, it is resonating to your point. It’s clicking for him. That’s awesome.

[00:39:23] Kevin Rice: Yeah. What are you hoping to like? What lessons or values are you hoping to share with your daughter as she gets older?

[00:39:30] Deena DePhilips: I said this to you already, but as when I became a parent, I used to think like work was everything.

My world revolved around it. Again, seven days a week, sleeping under the desk, 80 hours. That’s. That was definitely the reality of my world probably for a decade. And again, you know what it’s like building Hathaway into what it was. When I had my daughter, I realized work is my passion, but my daughter is my purpose. And I want her to have a healthy relationship with work too and not to over index your identity into your career too much that there are more important things in life like family and your kids and that your mental health and taking care of yourself. And so yeah, I hope I instill work ethic in her, but I hope it’s a little bit more balanced than, than what I did.

[00:40:20] Kevin Rice: Yeah, no, I love that. My career is certainly a passion area for me too, but clearly my kids are the purpose, like they’re my why for everything that I do. So I, I certainly resonate with that. When you, when you look back and you’re in that rocking chair, when you’re 120 years old, what do you hope your legacy looks like both in your career and, and as a mother?

[00:40:46] Deena DePhilips: Yeah, I hope all that red light therapy gets me to 120.

I that that I was a, that I was a good mom and I made a difference and an impact in my career. And for those who worked with me, I think it’s, it’s that simple.

[00:41:05] Kevin Rice: Beautiful Dina, thank you so much for joining me today. You are such a talented executive and like deeply conscious parent. I really enjoyed our conversation. I know our listeners are going to take so much from what you shared.

[00:41:18] Deena DePhilips: Yeah, well, thanks for thinking of me. I, like I said, I’m a big fan of the show. I listen to the podcast. Please keep it going. Every episode has resonated with me in some way. So I think what you’re doing is really cool and it’s a topic that needs to be discussed because I don’t care who you are and how high level you are, everyone is going through this challenge of how do I be present at home and also make an impact in my career. So thank you for just bringing this.

[00:41:46] Kevin Rice: Today. I think what’ll stay with me most is how you shared your belief that motherhood isn’t a pause in your career, but more of a launching pad. And the way you’ve embraced chaos and chosen presence over perfection, they’re really powerful reminders of how to lead in life and in work. So thank you so much for joining me today. If you’re enjoying this conversation, make sure to hit subscribe so you don’t miss future episodes. CEOs and ABCs is all about helping you grow in your career and show up at home. We’ve got many more amazing guests coming up, so tap, follow and stay tuned.