Let's Ride w/ Paul Estrada

Athlete Advisor: Faith, Purpose, and Raising Kids with Character

Paul Estrada Season 1 Episode 29

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0:00 | 43:04

What makes a goal worth chasing if no one is handing you a trophy? We open with that simple, disarming question and follow it into a rich conversation about character, faith, and the kind of grit that lasts longer than applause. Our guest, leader and advisor Jen Paulino, grew up in a military family where “it builds character” and “remember who you are” weren’t slogans—they were scaffolding. She shares how that foundation carried her into entrepreneurship, why starting a business exposed hidden insecurities, and how returning to core values rebuilt her confidence.

We zoom out to the bigger picture: faith versus organized religion, and how belief can inform work without becoming a wedge. Jen breaks down the myth of tidy success formulas and shows why presence in the process matters more than any playbook. We talk athletes, trauma, and purpose—how scarcity hardens discipline, why achievements don’t heal old wounds, and what drives many high performers to give back through schools, nonprofits, and community projects. The throughline is clear: purpose outlasts status, and alignment outperforms hustle theater.

Parents will find practical takeaways, too. We tackle screen time with nuance, showing how to trade passive consumption for creative play and social skills without demonizing tech. We share smarter reward systems—affirm effort, teach endurance, and skip the hollow participation trophies. Jen also makes the case for seeking wisdom in community: journaling, scripture, mentors, and elders who help us see what we can’t yet name. For creators and founders, she offers a powerful reframe—rejection is redirection—especially when earning trust in guarded spaces.

If you’re ready to build goals that stand on values, not vanity, this conversation will meet you where you are and nudge you forward. Subscribe, share with a friend who needs a reset, and leave a review with the one insight you’ll act on this week.

New Year, Goals, And Dishes

Adrian

What's your questions?

Paul

Well, the first thing I want to know, because I haven't talked to you. Well, I do talk to you every day, but I haven't talked to you with a microphone in front of me for a long time. And I just want to know, like, how was your New Year's?

Adrian

It was really good.

Paul

Did you set any people set goals for themselves in the New Year's? Did you do anything like that?

Adrian

Uh no. Did you set me a goal?

Paul

I don't set you any goals. You gotta set your own goals.

Adrian

Okay. You can set me goals some if you want.

Paul

Uh like goals about your school or what kind of goals do you think?

Adrian

Goals whenever you want.

Paul

Alright. I want your goal to be to do the dishes every single day for the whole year. Could you do that?

Adrian

No.

Paul

You just said I could set the goal however I want. Are you kidding? No, I'm not kidding. You said I could set it however I want.

Adrian

But what if I'm not home every day if I'm like spending my night at grandma and grandpa's?

Paul

I'll give you a break on those days, but all the other days. How about that?

Adrian

Like when I'm not gone?

Paul

Yeah, when you're home.

Adrian

Well, what if I don't have enough time?

Paul

That's the whole thing with the goal is whenever you set a goal for yourself, you have to prioritize it and make time for it.

Adrian

Well, I might accept my uncle later.

Paul

Do you think if you were to set a goal and you were to make it happen really fast, does that mean that you made the goal too easy? Or what do you think?

Adrian

Too easy.

Paul

Too easy, right? So then maybe you could make a your goal harder?

Adrian

Yeah.

Paul

Okay.

Adrian

Like to do it for longer.

Paul

And what if you set a goal and at the end you accomplish your goal and then nobody gives you a trophy or nobody gives you money or anything like that? You just accomplish your goal. Yeah. Do you think it would still be worth it?

Adrian

Yeah.

Paul

Why?

Adrian

When you accomplish your goal or something, you don't need a trophy or anything. I feel like all you need when you have a goal is just to accomplish it.

Paul

Why do you think that?

Adrian

Because like, as people work for money and to buy trophies and stuff, so then they don't like they don't have to get all the time for you. And then you just win.

Paul

Alright. So there's something called like self-satisfaction, meaning you don't have to get recognized, you don't have to get money, you don't have to get a trophy. But just the thought of knowing that you worked really hard for something and then accomplishing that is what's supposed to feel really good. Not the other stuff. Does that make sense?

Adrian

Yeah.

Self-Satisfaction Over Trophies

Note From The Host And Setup

Introducing Jen Paulino

Paul

Alright. Hi, let's ride listeners. Quick thing before we start. This podcast technically has a boss. His name is Adrian, he's seven. He checks the subscriber numbers every week, he sets aggressive targets, and I've been told just try harder is his full management philosophy. So follow or subscribe and tell a friend to do the same. It'll help me keep my job. And stick around because this is a real-time journey. Learning, parenting, work, life. I'm sorting through all of it out loud for your entertainment. So come on this journey with us. Now, let's ride. Our guest today is someone whose story, perspective, and wisdom go far beyond a job title. She's a leader, entrepreneur, advisor who works closely with athletes and high performers, but at the core of everything she does is character, faith, and purpose. Raised in a military family and constantly on the move, she learned early that identity isn't tied to a place or title but to values. Grounded in faith and shaped by the idea that it builds character, she's built her life and career around growth, discipline, and internal development rather than external validation. From advising athletes, navigating identity beyond sports to helping people build businesses and impact-driven initiatives without compromising their values, she brings a rare mix of clarity, depth, and lived experience. This conversation goes deep into faith and work, privilege and work ethic, parenting, pressure, purpose, and what it really takes to live aligned with who you are, not just what you do. Our guest today is Jen Paulino. So I won't read the whole thing, but it says she's driven by her values of faith, accountability, integrity, temperament, and humility, and strive to do good works and help others elevate. She's also an open book who loves if you talk about some things that you love. And then finally, which I really loved is she welcomes anyone who wants to connect and chat with her. Well, Jen, I'm that anyone. So thank you for welcoming to connect with me today. I really appreciate it.

Jenn

Thank you for having me. I'm really excited about the heart behind this and just you deciding to do this to teach your kids different careers and to be able to like show them something different, give them something to choose from. And so I think that's really beautiful and that speaks a lot to where we see media going now, especially media geared towards kids, which is let's give them examples of what life really looks like.

Paul

If you begin to just take us all the way back and give us some perspective into who Jen was growing up and kind of some of the things that helped laid the foundation for who you are today.

Jenn

That's a very loaded question. So I'm gonna kind of consider.

Paul

Yeah.

Roots, Faith, And Identity

Jenn

Um, so my dad, when I was growing up, he would always tell me two phrases it builds character and remember who you are. And my favorite movie was The Lion King. Um, and then my secondary was Spirit Sally and of the Sigma. And I would say those two movies really shaped my childhood in the sense of the Lion King was this consistent, like, you need to make sure that you are always rooted in where you came from and who you were destined to be, regardless of where life takes you. You always come back home. And for me, that was my faith. So home to me was never a place. It was a heart posture, it was a character development point. It was always something that allowed me to, wherever I went, to touch down because my dad was also in the army. So I grew up changing towns, changing friends. Um, and then most of the people that were around us were in the military or they were athletes, baseball players, etc. And so people were always on the move. And so I never had this sense of like this is my village and it looked the same year over year. It was all changing. And so I needed to anchor myself in something. And it was, this is who you are.

Paul

Let's go back. You talk about loaded. There's so much in there that I gotta go back and unpack. So let's let's do my best here. So let's go back and talk about you mentioned two phrases that your dad um said. Can you remind us of the first one?

Jenn

Um, it is it builds character.

Paul

It builds character. So how often, I mean, clearly it's resonated because now all these years later, it's something that still sticks with you. Is this like a daily like affirmation thing that you were hearing? Is it how regular was it? And maybe just give us an example in which you would apply that phrase.

Jenn

Yeah, so I'm actually, I just finished my book not that long ago, and I'm in the process of like editing it and refining it, but it's called It Builds Character. Okay. And the reason that I called it that is because I'm a big believer in the process. So I think a lot of people fail um to be present and experience everything that is happening around them because they're always trying to strive for something, right? And so I mentioned I anchor myself in my faith, which is I follow Jesus. And in that, one of the things that the Bible teaches you is that the process is important. And it also calls us to be peacemakers, not keepers. And when you think of keeping something, you think of never changing it and just kind of like storing it in a little box, right? But when you think of making something, you are consistently pushing, you're consistently changing, you're moving. It is an ever-flowing thing, right? So I'm starting to equate what is process and creation in the same space. So that for me is where character comes in, which is there's never a destination. Your character is never going to be perfected. Every level that you go, you're gonna learn something new, right? And one of the things that was really challenging for me was when I started my business three years ago, I didn't realize that starting my business was going to expose the parts of me that I didn't even know existed. So I started to have these moments of like, oh wait, I didn't know I had abandonment issues. Oh wait, I didn't know that I had insecurities of that magnitude. I didn't know that I cared about validation like that. And it was this consistent, like unwrapping and unraveling of me. At some point, I was like, wait, I don't even know who I am anymore. And then I got to a place where I was like, wait, let's go back. Let's start with the fundamentals. Who are you?

Paul

Right.

Jenn

And how do you show up in the world? And that really gave me the stepping blocks to get back to that foundation that I had built and say, okay, this is who I am, this is my character. And that doesn't change even in my circumstances or the way that I make money, any of that.

It Builds Character: Process Over Outcomes

Paul

Yeah. Well, I think you saying this is my character, like an avatar, like this is like I'm this is what I'm showing to the world, right? Yeah. And I I think you know what you do when you're talking about your upbringing, and I, you know, I was thinking about, and I this is episode 20, 29, something like that. Congratulations. Thank you. The idea of faith and how that plays into work and things has not come up. And shame on me because, you know, I grew up in going to uh Catholic school and and doing all these things, and part of me was a little bit, you know, I try to stay away from things that are controversial, so I don't talk about politics and I don't talk about this. Yeah. And maybe I I think religion falls into that category, although saying that out loud is is kind of like, wait, why is that controversial? It doesn't have to be this specific faith per se, but just the idea of being spiritual, of being and how that inner um how that plays a role in how you present yourself in a professional way and things like that. So I do want to spend some time talking about that finally. So um, yeah, if you could just uh touch and you know, you made some references already, but just how does the faith piece play into how you approach the world of business?

Jenn

Yeah, I think I'll start by addressing something that you just said about you you always kept it out because it seemed controversial, right? I want to add another layer to that, which is in the United States, we've been taught that there's a separation of church and state, right? Um, we've been taught that we separate certain things. So when you go to businesses, you typically don't see people approaching their faith outwardly, right? Because faith is associated with religion. And I think once we start to unpack the fact that religion and faith are not the same thing, organized religion is structure, it's a way of worshiping and expressing your faith. But it's not your faith in its totality because even within organized religion, people approach it differently, right? So there are multiple denominations of Christianity. And I think that's if we can be more open and transparent about that, religion wouldn't be such a hot take everywhere. It would just be a conversation of how we worship something bigger than ourselves.

Paul

Well, I think, you know, so we decided to to send our kids to a Catholic school as well. Part of it was just for the for the educational aspect, but also the religious component of it. And, you know, just uh call myself out here. But we said, hey, we haven't been to church in a long time. So if we're gonna, you know, send our kids there, we better start showing up once in a while and at least uh getting involved with the community and like we can't just say this and do something else, right? And so we did start to go in there. There was a there's a very young, uh, vibrant priest there. And one thing that he says is my generation, me being uh, you know, let's say in the 30s to 40, for early 40s range, has said that faith and and church is optional. We've decided in our head for most of us that it's optional so that for the next generation, it will become almost like obsolete. Meaning every generation you go, the further away you get. And so he kind of jokes around now, but he said, Hey, look, when I go out now and I just try to get people to engage, I've already decided you guys are lost. And he kind of says it with a smile on his face, right? Yeah. But his point is, I want to get to your kids because there's still hope for them. There's still a chance that they can integrate uh into this and you know, and do it that way. And so it's just a fascinating take. And I try to take it more so not, and I I like what you said about not necessarily the religious aspect, but just focus on the faith aspect of it. Is now that I think about it and I think about some of the most successful people that I see in the industry in which I operate, they've achieved the wealth, they've achieved, they've got the house, they've got all the material things that they could possibly need. And I've seen a bunch of them now kind of shift focus and they still run their businesses, but they create these nonprofits. They're they're building schools for less fortune, they're doing this. So they've kind of unlocked this. Okay, all my needs and my wants have been met. And so now I can go and take all my abundance of resources and go do these other things on top of that. And then almost like that faith piece becomes like a centerpiece for them again. And I know you're working with athletes, I would imagine kind of in that similar vein, right? It's like they're all making good money and things like that. So if I know I'm bouncing around a little bit, but if you kind of speak to that uh piece of where does that, for these athletes that that are trying to do for their community, where does that inspiration for them, do you think, come from? And like, do you see what I'm trying to tie this bow around people that have been successful and now want to shift their focus to that? Is that something you commonly see? I would imagine.

Faith And Work Without The Labels

Jenn

Yeah. And I think it's the concept of for so many people, like it's one of the things I tell to people about athletes. What makes athletes really good, a lot of times is their trauma. That's the unfortunate piece. What makes them really good is the circumstances that they had to fight through in order to become as good as they are, right? So whether that was being in a really competitive environment or that was being in a very impoverished neighborhood, whatever the case may be, what ends up happening is that trauma, that lack, that scarcity, that need to survive and compete propels them to a place of unimaginable mental discipline in order to reach that goal. Once they get there, they realize, wait, that didn't heal my trauma. That didn't really fulfill what I thought was missing. And then they go on the search to do for the little version of them what they wish somebody would have done for the little version of them back then. Um or fulfill a need that they see could propel somebody to get to where they are. But then you see the fact that it doesn't matter how many needs you fulfill for some people, they never actually reach what that pinnacle of success is for them because they didn't have that drive internally, that hunger, that desire to get somewhere, right? And so for some people, once they've reached that, they're like, okay, well, I gotta keep going. I can't just stay here. And faith comes into play because they've seen that there's that something has to be driving them. And then you have the people that don't, which are the ones that you see that just kind of plateau, and then you never see or hear from them again. And you hear about the depression and the suicidal ideations and all of these things because people stopped having a purpose, they stopped having a reason to get out of bed, they stopped having that goal that was pushing them and constantly moving the goalpost um to do something, right? And so it's just about balance. You can either choose to have a goalpost that you're constantly moving, or you can choose to believe that there's always something greater out there. And if you're present and you just continuously go on a journey and every day try to just perfect yourself versus having an arbitrary goal, then life becomes a little bit different.

Paul

I had a so my son's seven years old, and he obsessed with baseball. And just like every seven-year-old that plays baseball is right there, the idea there is, hey, I'm gonna be a professional baseball player. And you know, in the back of my mind, you know, and I and we did have a professional baseball player on here to tell us about just how low the odds are of that happening. Not to discourage us, but just to put things in perspective and reality. And one thing he he talked about several times was, you know, here these kids in the US, it's like, like I just told you, my kid goes to Catholic school, there's always food on his plate, he's always clothed, he's got, you know, the equipment that he needs to be successful. And he's out there and you know, he's you do one extra practice, and it's like, yeah, I'm working really hard. I'm working harder than everybody, right? I'm like, no, no, you're not. There's there's kids all over the world, especially, you know, in the DR in Puerto Rico and uh places like the Cuba, where this is like their only means or their perceived only means to get out of the position that they find themselves in. And one of the things that I notice with that in those impoverished communities, in addition to that, and just to kind of tie this together, is they seem to also be very tied in their faith, right? Like they don't have much. Yeah. And so it's almost like, hey, I have to rely on my faith to like give me what I'm not getting from other places. And so I don't, I just see this kind of circle as I'm as I'm trying to piece all these things together. And I'm just curious as you see and you work with these athletes and and these communities, is how I'm describing it, how it is, and maybe if you can just talk about some of the other nuances associated with that.

Wealth, Purpose, And Giving Back

Jenn

Yeah, I think there's two things that play into um that play into this. And the first thing is structure and organization. The United States has created this concept for the middle class and higher that if you just organize things and you follow the instructions and you follow the rules, eventually you're gonna get where you need to get, right? So I remember when I was learning sales, people would always tell me you just need to do 10 calls a day. And then 10 calls out of those 10, five of them might answer and call back. And out of those five, maybe one of them, right? So there's always this formula that people tell you is you do a certain amount of work, that's gonna equate to a certain result, and that result is eventually gonna lead to your success. That's a lie. That is such a lie that we have told people because we wanted to make things accessible, right? You have this um, this culture with social media where you have a lot of business coaches. I remember when I first launched my business, everybody wanted me to go the coaching model and teach people how I had raised money for nonprofits and helped generate thousands of dollars in sales for for-profit companies. And I was like, listen, I can't tell you who Jennifer is in a one, two, three step. And that's where my sales came from. That's where my success came from. It did not come from following a formula, it came from showing up as myself, having intentional conversations with people, and from there finding the yeses and the no's that would lead me to the path that I needed to be on. Right. And so, yes, there is organization and structure that should go into that, right? I needed to show up every morning and send the emails, but the emails had to have my flavor in it. I think we need to think about how when we're teaching our kids here in the Western world about success, we teach them that there are certain things that they have to their advantage that puts them a little bit ahead of other people in terms of how they get started. But the work that they are doing on the field is internal so that when the competition rises, their mental state is strong enough to endure because that's where we're seeing them tap out. It is not like kids in the Dominican Republic might not have a glove, but they gotta walk to the field every day for miles. So that endurance just to get to the field is what is propelling them ahead of the game. It is the work that they are doing unbeknownst to them that by the time that they get access to that glove, they can feel like a 16 year old at 12.

Paul

Right.

Jenn

And that's where we miss the steps.

Paul

You see the videos online, it's like, okay, they got the broomstick and they're hitting bottle caps and they're right, they're doing, they're making use and they're being as resourceful as they can be. But even you know, even still, most of them. Are not going to become professional baseball players, right? So to your point and what you're saying, is it the case though that, you know, they are putting in a ton of work with this big goal in mind? Most of them won't achieve that. But is it the case that for those that don't achieve, you know, professional baseball player, they've built a certain work ethic that then allows them to become successful in whatever business or career path they decide to choose, or do they just fall off a cliff and end up I don't know where?

Jenn

And that's where we get into the concept of what are you doing it for and why are you doing it? And that's what we're seeing the shift in baseball right now, especially internationally, where people are trying to teach these young men that they are more than just athletes. They're more than just providers. They're more than just the sum of their work ethic because they have work ethic when they think there is a reward, right? The reward is becoming that baseball player and getting that money. They a lot of them don't actually care to become a baseball player. A lot of them care about making the millions to support their village. It's not their mom or their dad, it is their village. It is the people who have raised them, the people that have fed them. And so when that's no longer tangible, when I can no longer buy my grandmother's house or my mom or just help my neighborhood, I've lost all motivation and all fuel to put that work ethic into place. It's kind of like having a car that you've built, but now you don't have any gas to put it in. Right. And so that's what happens there. And it's a problem because we go back to the same. Both places have a similar issue. The United States, because of our privilege that comes with having access to being able to because people don't realize being able to get yourself in debt is a privilege, oddly enough. Because not everybody has access to somebody else's money that is gonna help them do something with it, right? And that's really odd to think about. But when you put it into perspective, how many people don't start businesses off of a credit card that they were able to get, even if it was a fifth $500 credit limit? That $500 would have taken somebody in a different country that doesn't have as sophisticated of a banking system years to save up, to start that business, right? That's a privilege in and of itself.

Trauma, Drive, And The Athlete’s Edge

Paul

So I'm curious since you have this unique perspective where you lived it, like you were in another country, you you kind of both you have the US experience, you have the experience in the Dominican Republic. Like you said, they're at advantages in certain ways, where the US is at advantages in certain ways. How do you think about just for those that don't have family that live in a you know a third world country? What are some ways that, hey, we really want our kids to have that sort of work ethic, but you know, it's not realistic for me to go have my kid go spend a couple years in Mexico, for example, right? Yeah. What are some ways that you could see us instilling that type of work ethic with the you know disadvantages of just the privilege that we have?

Jenn

I think there's two things. Um one, screen time, limiting time your kids, like actually making them go outside and interact with each other. That human interaction, like I've met so many kids that won't say hi to adults and they'll won't say hi to other kids because they're not socialized in a way that really lets them see other humans as like tangible things. To them, it's like you're not on the other side of a screen. Like, I don't know what to do with this. Um, so I think just socializing them and getting them away from screen time and getting them into environments with other kids is helpful because they develop. It's like they've done studies on language where if you take small kids that are just learning how to speak and put them with kids that have already developed language, the younger child will develop language faster than if they don't have that child because with amongst themselves, they're able to say, Oh, we're the same age, like they have commonalities, and then the differences and different skill sets will help refine one another. It's kind of like saying when you're in business, they one of the first things they teach you in mentorship is you want people that are 10 steps ahead of you in business to mentor you and then 30, 40 steps ahead of you because you're learning through being in that environment and that high pressure. The second thing is reward systems.

Paul

Sorry, Jen, before we move on, let's just I want to talk about this one because this is, I think as my listeners hear that first one, it's gonna be a trigger, right? And as you heard when he just said, I was like, oh, hang on. First of all, it's super, super easy to put your kid in front of the screen. It works, like in the sense that you want them to stop yelling, screaming, kicking each other, destroying the house. It works. Like you can put them in front of there, they'll be quiet, they'll do like you won't hear a peep. And it's so, you know, you say the screen is addicting, it's addicting for the parents as well to get that calmness that is like coming from that screen as well. That being said, you know, we try to be a little bit deliberate about how much time is given. We do do it, but you know, so they have their time. Yeah, but when they break up, it's like, okay, guys, it's time to break up. And what always blows my mind is how creative that they can be to find entertainment for themselves. Yeah. So yesterday, for example, my son was in the garage. There was a box that I had from Costco. I, you know, they put all your groceries in there. I left the box there. He went in the front yard, he found a stick, and he just starts beating the box, like like he's swinging a baseball bat. Yeah. He's like whacking this box with the stick, and he's having like the best time of his life. And that's like loud, and it's like he's making a mess. I'm like, I don't care. Like, it's like hilarious that he just like went out and he has all these other toys that we paid money for that he could go in his closet, go pick out, go do something. But what does he do? He goes outside, he plays with a stick in a box. And so, as we were thinking about you know, Christmas coming up, we're like, hey, what what do we get these kids? And we're almost joking, like, literally, like, let's go get them five cardboard boxes and like some duct tape and a sharpie. Yeah, and just like do it at that. Um, because these kids, they don't, you know, they don't need the video games and all, like, they're perfectly happy. And the more I thought about you know, growing up as well, it's like, yeah, you just would get really creative. And I think we have gotten away from that a little bit. And like I said, I I don't blame people because it is super easy. Um, but it is kind of amazing that if you just shut it off and let them run around, like they'll amaze you. That's what I've been finding lately.

Beyond Sports: Purpose After The Dream

Jenn

And I think also with the screen timer, I think screens are amazing for communication, education, entertainment. I love like my family has a regular movie night um when we're all together. And my brother and I are grown. And my dad started that. I'm 31 and my brother's 26. And since we were kids, my dad always had Sundays was movie day. So we would go to the movie theater, and then once Blockbuster became a thing, we would go to Blockbuster and we would pick three movies. And there was a Friday night movie, Saturday night movie, and Sunday night movie, right? And then Netflix became a thing. So then we started doing it there, right? So with the evolution of this tradition, we've evolved. And now my brother's married, and he, him and his wife, when we're all together, she knows it's movie night. She knows when we are with my dad, it is movie night, and we are sitting as a family doing this, right? And so I think screens can create a tradition to bring people together to educate your kids and everything. I just think it's a matter of how you introduce them. So my brother and I, my brother had a Game Boy. He, I had we both had PSPs, we had Game Boys, we had literally every sort of handheld device you could imagine. And my brother was hyper. He was hyper child. But my parents found a way to organize the chaos, right? So for my brother, it's like he had limited screen time, but my brother had this little rug that had this track on it, like car track. So he would run his little Hot Wheels through it. So he didn't have like a whole Hot Wheel system. He just he ran it through the rug, right? And so they implemented things into his room that helped him be more entertained and added sensory to his environment. And I've been seeing a lot more parents do that where they have like a room where they've built like some sort of jungle gym system for their kids, or they've put in toys that are more sensory focused. And I think if you can give your child a controlled environment, so maybe you don't have a whole room for the child, but maybe you have a space in your living room that you've designated that has a little table there with coloring and wall things, and like that's their area to just do whatever they want and you teach them discipline, and this is your area. You can do whatever you want in this little box in this area, it creates this space where you have a little bit of control in the chaos when you pull them away from the screen.

Paul

Okay, so we went off on something. I'm really glad we dove deeper into that. So, number two, you're getting enough. So number one is screen time, number two us.

Jenn

The number two thing is the trophies and reward system. Is like, how do you add a reward system to your child that actually teaches them work ethic and not reward only? Um, because a lot of people they reward the small wins, which I think is beautiful. It's encouraging, right? But what happened to just affirmation of the child that they're on the right path, right? We need to start thinking about the way that we engage because we're rewarding everything. We started at some point giving participation trophies out for low-level um effort. And so now people think that they've done one thing and all of a sudden they should be the best of the best because we've been rewarding all of these things. And I know all these things are really hot takes, but I'm in the center of my brother and I, two different generations, and we're only four or five years apart. And I've watched the difference in the way that he approaches life and the way that I approach life. I was taught you didn't get a trophy for for participation. You got a trophy because you were the best of the best if you work towards it. He was taught you get a trophy for participation, right? And so his ability to endure mentally through challenges and obstacles is very different than mine. And he's having to relearn a lot of things that he thought was normal because everybody around him operated that way too. Versus me, it was like, no, if you don't work, you don't get it. And I'm having to learn from him. It's like it's trying is sufficient. You don't always have to kill yourself to get to the end. And so I think it's finding that balance between affirmation and pushing that you can really find the beauty and that you don't have to be in a low-income, impoverished neighborhood to try hard and drive, but you also don't need to ignore your privilege in order to get where you want to go.

Privilege, Access, And Real Work

Paul

Yeah, I think that's that's fascinating. And you know, just on the I'm smiling over here because on the trophy thing, I just I was, you know, pulling down some the Christmas stuff so you can, you know, go decorate and things like that. And my parents in the way back in their attic, they I found boxes of trophies and they had my brother's box. It was full of trophies, and I found two of mine. And I said, you know, I'm gonna bring these home. I think my my kids will get a kick out of seeing these trophies from way back when. First thing I'm gonna say is they don't make trophies like they used to, man. That thing was like a brick. That thing was like 10 pounds. It was like, I don't know, two feet tall. So the first thing my son just like, Wow, like this is what did you win? I'm like, this is actually a second place trophy. This isn't even the championship trophy. Um, and then two, when I showed it to him, that the second thing was it reminded him he just finished his fallball season. And he's like, wait, dad, we just finished fallball and I didn't get my I didn't get a trophy. I'm like, you're not getting one, it's fallball. Like it's this is not like this is like the practice, this is not the real, the real deal. And he kind of got bummed out for a second. And to your point, I said, you know what, you know, your trophy was without sounding without trying to sound too uh, you know, full house uh-ish right now, is when you were, you know, when we were doing a bullpen session and you couldn't throw a strike to save your life, and you know, you you stepped off the mound, you took a breath, took another breath, you even melted down a little bit, you know, you let yourself cry, yeah, you came back, reset, refocused, and all, and then you're throwing strikes. And we ended the day, and you know, you struck out up invisible batter, or you know, whatever. And I don't know that I mean he's seven, so I don't know that that necessarily resonated or clicked in the way that I'm thinking, but I'm just trying to, to your point, be very intentional and deliberate um with those sorts of things. Cause yeah, I don't know. I I don't know. It's so Jen, I want to call this out, and that is you mentioned a few minutes ago that you're 31. I'm 40. The things that you're talking about, the concepts that you're talking about, I feel like I'm just now like figuring out. So in the back of my mind, I'm thinking like one of two things is true. Either one, I'm like a super slow learner, or two, like you just have really figured out, you know, the key to this stuff pretty early on in your career. I'm gonna go with that. Um, that it's the latter, not the former. Where does that come from? Like, where where does that I feel like you really got a lot of wisdom to share that just from growing up? Like, what what is it? Because there's something there that I'm like, what the heck's going on here?

Jenn

Yeah, so it's two things. So one, it goes back to faith, right? So for me, I spend a lot of time reading my Bible. I spend a lot of time sitting with God and analyzing myself. So I do a lot of without external validation or external noise. I try to just sit down with God and journal and just allow there to be this like development within self, right? Because I go back to my base, which is if we are, you know, beings that are multi-layered, there's a specific word that is escaping me right now. But we are flesh, spirit, soul, mind, body, heart. All these things operate differently. My mind operates very different than my physical body. Sometimes you feel pain, like when you go to the gym. You go to the gym and you're working out. Your muscles might be fatigued, but your brain can tell you to keep going, right? Right. Your heart might be in pain that day because you experience some sort of disappointment or loss. So these three things are doing something very different. And then there's something external to you up here somewhere that is like just push a little bit more. And your brain is like, and then your body's like, ah, and then your heart is like, this is healing something inside of me, and I'm not sure. And then all of a sudden you leave the gym, your muscles are stronger, your heart is no longer in pain, your mind is like, whoa, I didn't know we could do those things. And there is something above you that is like, I'm proud of you, right? And we don't stop long enough to experience all of that. And that's where being present is so important because if we can just stop long enough, we're always trying to just, okay, I finish this onto the next thing. I finish this on to the next thing. And we teach kids that we teach them you you finish a project, you start a new one. They don't get to celebrate, they don't get to enjoy, they don't get to reflect and look back. And so I think having that for me as a part of the development my dad gave me, which is, I'm not gonna tell you what you did wrong. You need to figure it out. My none of my teachers would tell me. And so I had to find a way to process all of that at a young age and be like, how are you gonna show up? You're gonna show up for each person individually, you're gonna show up differently for every group, or are you gonna stop long enough? Process who you are, how you want to show up, and regardless of what anybody thinks or feels, show up that way. And let me tell you, I learned a lot of really hard lessons and I wasn't able to fit in in a lot of places, but all of that helped me acquire a lot of the wisdom that I have now because I didn't need anybody else's validation to learn a lesson. I didn't need to learn the lessons everybody else was learning because I realized I was on my own journey. And the older the community around you, the more wisdom you acquire and the faster you acquire it. So I spent a lot of time with my grandfather who passed away on the back in September of last year. And we would have coffee dates anytime I was in Dominican Republic every day. We had our coffee date at 12. He did not drink coffee, but I did. So I would drink my coffee, he would drink his water, and I would talk to him about life, and he would give me his perspective. Same thing with my dad. I sit with my dad for hours on end and I give him what I'm going through in life. I actually caught him right before this, and I was like, Dad, I told you that all of these different things were gonna happen in the next few months because God had been putting it on my heart, but I feel overwhelmed in the best ways, but also I just need somebody to talk to. And sometimes he tells me everything I need to know, and sometimes he's telling me things I already know.

Teaching Grit In Comfortable Homes

Paul

You know what's interesting about that is that is how my brother is. In fact, when I was telling you about going up in that attic and getting the trophies out, my mom was, and it's funny, she's just like him. She's out on the front lawn pacing back and forth on the phone. And I'm like, she can only be talking to one person, and that's my brother. And sure enough, afterwards, that's what it was. Um, and it got me thinking, though, that we are very different in that way. Yeah. Where I don't want help from anybody. Like I want to figure it out on my own. Even if I'm going through some things, for the most part, I'm not gonna open myself to anybody. Uh, partially it's like uh am I being a little bit of a burden on them. Part of it could be like embarrassment, part of it could be just like this perceived independence where I just, hey, I gotta figure this out for myself and I don't want anybody's help. Yeah. And I think there's something to that, but at the same time, there are people out there that can help. And maybe it's not, you know, they're not solving the problem for you, but maybe they're giving you, hey, have you looked in this area, have you looked in that area, or just something that helps kind of continue the flow of the thought process and how you're solving this problem. That I just, as you were saying that, I just I I realized, you know, I tend to just go on these things on my own. And I think I do get to the intended destination, but it's not without a lot of work and sometimes some heartache to get there. So I think what I'm hearing from you is like, hey, you know, you just gotta kind of one, you talked about just reflecting, right? Is sitting down, being very deliberate and finding time to just shut the noise off, try to play back. Wait, where are you at? Where am I going? What am I doing? And then the second thing which you said, which was, hey, and when once you've kind of figured out what's going on inside and you need a little direction here or there, like go out and get it, right? And so I love both those things. So that's how I understood what you just said.

Jenn

Yeah, and there's actually a book, um, well, it's not it's a book in the Bible, but it's the book of Proverbs. And in Proverbs, it Proverbs is considered the book of wisdom. And it says that common sense is a gift or a treasure that you find. And I think about it from this perspective if common sense is a gift or a treasure that you're finding, that's not coming from you, it's coming from external to you. And I think if we can think about wisdom, common sense, and these things that we think we should inherently just have as a gift or a treasure that we gotta go out and seek, it'll take the pressure off of us having to always feel like we have to have all the answers. I'm going to go seek it. Because even when you do things on your own, you're having to figure it out. You're having to go seek. So why not seek in community? Why not seek with people who may be a few steps ahead of you? You might not take everything from them, but you garner what makes sense for you. And then you move on to the next person. And after a point in time, you'll have all of these different pieces that now make this beautiful piece of art that you wouldn't have otherwise had the colors to paint with because you didn't know that if you mixed this tone and this tone in the middle, you could now put a rut, right? And so it's through that journey that you're really learning how to take different parts of people to create a masterpiece.

Paul

So now you're gonna take all this wisdom that you just uh shared with us, and you're off creating something of your own, uh, your own business. And so I'm just curious, and you know what you're doing, you know, you're working with athletes and things like that. These are people that are very guarded, I would imagine. They've got people that have been coming out of the word work asking them for this, that, and the other money and status and houses and cars and right. So there's there's probably this I don't wanna I'm a little apprehensive when I meet people and guarded and you know you're trying to go into that space and work with them and in, you know, whether it's creating a business or creating a charity or something like that. So I wanna end with just you talking about how you navigate exactly that, right? Which is like, hey, I I kind of want something from you, but I also want to I'm gonna give you something in return, or just kind of talking through and and just like not in a in a general sense, all of us, right? If we're creating businesses, if we're selling, we talk about this trust factor. So it's all kind of there's that overarching theme, but just specific to what you're doing, I feel like you pick this industry where it's even harder because of of what I just mentioned, right? So if you can just kind of like speak to that and how you overcome those obstacles.

Screen Time, Social Skills, And Play

Jenn

Rejection is not failure, it's redirection. And once you've gotten that down, everything else flows, right? So for me, every conversation I go into with an athlete, I don't care whether you want to work with me or not. And that sounds arrogant, but the reality is that if you want to work with me, is because we have a mutual platform to stand on. If you don't want to work with me, that's okay. I do want to know why, right? So for some athletes, I will, you know, I'll either have a conversation or I'm able to kind of just self-reflect and be like, okay, this person and I just didn't align on this project or on these values or on this, and it helps inform my decision, right? It helps inform my direction. I've worked with athletes before where I'm like, I don't think that you respect women.

Paul

Jen, I'm gonna call it the the book of gen, because that's why I feel like what I just did for the last 55 minutes was just learn from the book of gen. And so I I know you've got the book coming out, and I'm sure it's gonna have a lot of those types of anecdotes and things in it, and just really appreciate it. It's just really a like a a pleasure to to get to know you and just like seriously the wisdom. Like it's kind of blown out of the screen, and I just I I love it. So thank you for sharing with us and um really appreciate it.

Jenn

Thank you for having me. This has been awesome, and I love the conversation. It feels very organic and genuine, and I really pray that a lot of parents are able to hear your podcast in a way that will teach them from all the different people a way to help expose your children to something more than just what their environment tells them, right? Everybody's environment is the same, and so I pray that it continues to reach people and that you are motivated by every speaker that comes on here.

Paul

Thanks so much, Jen. Really appreciate it. Bye. Bye. We drive on that.