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Have you ever listened to someone speak and thought, wow, they are so authentic and grounded. I would love to learn more about their story? That was my experience meeting Dr. Jesse and Omar. We had such an amazing conversation that this podcast episode is actually two parts. Today we'll do part one and we're starting where most people rush past the early chapters, the childhood patterns, the coping, the roles you take on the way you learn to survive. Because when you understand what shaped you, you stopped blaming yourself for patterns that were trained into you. This is the Your Next Success podcast, and I'm your host, Dr. Caroline Sangal I'm a life first career coach and strategist on a mission to normalize questioning your career because I believe each of us is made on purpose for a purpose only we can fulfill. The longer we live out of alignment with who we are, what we do best, and why we are here, the more we miss out. And the more the world misses out on what only we can give. The Your Next Success Podcast is where we explore how to build a career that truly fuels your life. We talk about self-discovery, smart job, search strategies, professional growth, and you'll hear stories from people who have navigated big career transitions themselves, so you can create a life, first career and become your own version of authentic success. My guests today are Dr. Jesse and Omar, founders of A Souls Quest. They co-host the ASQ podcast and guide people through defining transitions with psychospiritual insight, with practical tools and grounded conversation. My conversations with Dr. Jesse and Omar touch on the place where you can look fine on the outside and still feel that quiet questioning inside you where you have titles, degrees, competence, and effort, and your body still whispers. Something is off. Where you try to power through and life keeps redirecting you until you finally stop arguing with what's true. You'll hear a love story here, and it's also a leadership story, a story about belonging, a story about pain that turns into purpose. A story about learning to give with wisdom, speak truth with integrity, and build a life that is authentic from the inside out. Today's part one of a two-part conversation. And in this first episode, we go back before the degrees, before the titles, before the now, and we talk about the early experiences that shaped how they learned to connect, protect, push, and persevere. And as you listen, you might notice yourself reflecting too on what trained you, what you carried. What you've been trying to prove. So if you've been at a turning point and you're asking, why do I keep doing this? Or Why does this feel so hard, even when I'm doing everything right, you are in the right place.

Caroline Sangal 3:21

Welcome Dr. Jesse and Omar, I am so excited to have you here on Your Next Success today.

Dr. Jessie and Omar 3:28

We are super equally, maybe more excited than you are. We're super excited. I agree. I was telling you I love your energy. I love the excitement. We've met before and I would love to have the conversation right now. So, yes, thank you for having us.

Caroline Sangal 3:40

And so, yeah, I think we have a, a aligned, maybe parallel interests in how we help people. Mm-hmm. And so this is a great opportunity. I was on your guys' podcast that'll be coming out in a couple months, and now it's awesome to have you here on mine. Mm-hmm. So we can kind of tell each other's stories and help as many people as possible.

Dr. Jessie and Omar 4:01

Absolutely.

Caroline Sangal 4:02

All right. Well, as you guys know, one of the things that I love studying is careers, career transitions, those sorts of things. And so I listen to a lot of your individual stories, from your podcast. I highly encourage people to go back way, way back on the ASQ podcast to listen to the beginning ones for even more of the story.

Dr. Jessie and Omar 4:24

Oh, wow. Yeah. It was good.

Caroline Sangal 4:26

It was great. Thank you. It was great for me to see a little bit because now you guys are, how many episodes do you have out in this moment? A hundred something.

Dr. Jessie and Omar 4:34

One a hundred and thirty two. Yeah. 132. Yes.

Caroline Sangal 4:37

Yeah. So it was refreshing for me to go back to your beginning and be like, they made it and they still sounded really good. Gives you some hope.

Dr. Jessie and Omar 4:44

What did we sound like on our first episode? Oh my goodness. Oh, it's been a learning experience, which is great. We'll get into all that. Yes, because it's part of the journey.

Caroline Sangal 4:52

Yeah. So I'd love to kind of dial it back to both of your childhoods. Can you, like, whoever wants to go first. Tell me a little bit about um, growing up and specifically what kind of work did you see your family members doing? What did you think in that moment as far as did you have visions or dreams of what you thought you might do when you became an adult? Those types of things.

Dr. Jessie and Omar 5:19

So I was born in San Juan, Puerto Rico, and I know I'm saying it like I should be saying Puerto Rico, right? Um, so I was born in San Juan, Puerto Rico, and I, my mother is Dominican and my father is a New YorRican. So he ended up back in Puerto Rico and ended up joining the military. So he wasn't around for the first couple of years of my life. Um, So it was just me and mom and, um, growing up we ended up moving to the states and first thing my mom said is I wanna learn how to speak English. We're speaking English in our house, period. Oh. So sadly, that sort of forced us to kind of lose our language and not, or my brother never had the language I did, but we just didn't hold onto that. We helped my mom learn English. Um, and then we ended up moving to Rockford, Illinois, which is right outside of Chicago. Some people know it and some people don't. So I always have to refer to Chicago. Um, and my family structure was very, um, sort of normal. Like we grew, I reflect on it now and I think, wow, I really didn't have a lot of you know, relationships with my father. And that's something that has been, punctuated now throughout my adult life, right? Um, but we had a really great relationship with my mom. She was like the mom on the block, like everybody loved my mom, right? She had a three wheeler. She'd throw all this stuff in there, we'd go do campfires and roast, marshmallows and hot dogs. And we just had a really good upbringing in terms of that, But one thing that I did notice is that one I wasn't very close to my father, he was not that dad that kind of went out to the park with us and did things like that with us. And he was kind of hard on me, because I don't know how my brother looks at this whole thing, although we have similar feelings about it, but we didn't really get a lot of optimistic interactions. It was very, pessimistic, we don't have any money for that. We're broke. There was common language that we picked up that I brought with me into adulthood, right? I realize that I did a lot of striving to make him happy, like to people please and get that affection that I was looking for. And I just never got it. And every time I would do something that I thought was good, you know, bring home good grades and do this and do that, and I'm evolving and transforming, I'm growing into this young little lady. It was just very negative. His interaction with me was very negative. It wasn't like, I love you, you're amazing, you're beautiful. It wasn't any of that ever. I mean, I can count on one hand how many times he said he loves me.

Caroline Sangal 7:54

Did you ever see his parents? Like, I wonder if that's just like my husband's family and my family grew up differently in terms of the affection. Yeah. Or like on one side, you know, it was hugs and kisses and I do love you. And even if you were pissed at somebody, it was, I love you, right? I love you. And then in my husband's family, it's like, don't say thank you, we're family. It's just like, understood. And it's not as touch and it's just, it's a different kind of love than I had. So my husband, either just stays with me 'cause I'm amazing or he does love me, but I think he does love me.

Dr. Jessie and Omar 8:31

Both. Both, both.

Caroline Sangal 8:32

But I wonder, is that how your dad was or that's just part of the family dynamic? Maybe his parents or grandparents or the things that he had seen, maybe he didn't have that. If you see it, you can be it kind of thing, right. Did he have it?

Dr. Jessie and Omar 8:45

I think for me, for almost all of my life, I'll be 53 next month and almost all of my life I was. In my adulthood, let me say my adulthood, I was always very frustrated with my father because I was always blaming them, you know what I mean? Blaming them for how could they treat me this way? Why, what do I have to do to get attention? I've done so many things that even as an adult earn my PhD. And not once has he said, congratulations. nothing um, from him at all. I think now as I've spoken to multiple people, I can look back and think this is what he had and this is what he did, because this is what he had and this is what he learned, right? I was very close to my grandmother at one point. His mom, um, she recently passed away and, um, but my grandfather passed away when he was 16, so I don't know about him and I don't know what it was like growing up. In that house, I assume that there was probably not a lot of emotions um, that were talked about. Um, but again, those are all assumptions because that's how it was in my house. We weren't allowed to grieve. We weren't allowed to have emotions. We got hit with the belt at that time. That was a normal thing to do, you know? Yeah. Um, we were told to just look cute, don't talk, you know, that kind of thing. Um,

Caroline Sangal 10:05

be seen and not heard.

Dr. Jessie and Omar 10:06

Yep. Exactly. Yep. I do think that a lot of it has to do with that. I can look back now and I can see that that's the case, that he didn't get a lot of affection. And I think there was almost an unhealthy sort of relationship between him and his mom. He was very, very attached to my grandmother. You know what I mean?

Caroline Sangal 10:22

With his dad passing away, then he had to step into a role Yep. Mm-hmm. Mm-hmm. You know, just being a,

Dr. Jessie and Omar 10:28

So, yeah, exactly.

Caroline Sangal 10:29

And did your mom ever work like she seems like an amazing mom, very welcoming to whoever wanted to come by and always made sure you guys were doing amazing things.

Dr. Jessie and Omar 10:39

She did work. I think my mom, again, when you reflect on this, and especially since I'm evolving and growing and learning things and trying to capture things that I feel and trying to kind of dismantle these things to understand why I feel this way. Why is this happening? Why does this feel this way? And doing what we say on ASQ asking what, right? What is the experience that I can learn from this moment or from those moments? My mom was a work person. She was very involved, like I said, in everything that we did. She worked, she tried to stay close to us so she would get jobs like at the school. So she worked in the cafeteria, so my parents were very blue collar workers. They were never people that sort of were like encouraging us with education, encouraging us with you know, it doesn't matter if you get a C on this test. Keep looking forward. You're doing great. We didn't get that sort of like support, It just wasn't like that. It wasn't something that they put on our purview, like, you can be this or you can be that, you could do these things. It was very much a very curiosity driven home. Like we weren't encouraged to like, be curious, try, in fact, we were told not to. You know what I mean?

Caroline Sangal 11:49

And even in the military, what kind of job did your dad have?

Dr. Jessie and Omar 11:55

In the military he was like a, I guess a diesel mechanic is what they call it. So, and even when he exited the military and went to work, he worked at a place, the whole industrial thing was going on and rock, lots of industrial stuff. My mom worked at a place where they built those plastic, you build these toys or airplanes and stuff. And you paint it with the paint.

Caroline Sangal 12:18

Oh yeah, like the little model airplane model set, yes.

Dr. Jessie and Omar 12:21

That she used to work at a place like that and she bottled the paint, if I'm not mistaken 'cause we, we used to get these little kits all the time at home, but we were never allowed to put them together. our curiosity was so stifled when we were children. It was almost like, go outside and play. Don't be messing up the house. So we didn't have a lot of that oomph, to try out.

Caroline Sangal 12:42

And did you ever consider oh, when I'm an adult, I want to.

Dr. Jessie and Omar 12:48

I used to think I wanted to be a doctor. Then I said I wanted to do, a lawyer.

Caroline Sangal 12:51

You are a doctor. My kids tell me I'm a doctor without any patience.

Dr. Jessie and Omar 12:55

Exactly. Right. Exactly. It goes always truth, facts. Yeah, but again, I didn't. I remember there was this conversation that I had with my dad, just to give you a kind of an overview. And I had told my dad, I wanna be a doctor. I told him, I was in the backseat with my brother, and I said, I think I wanna be a doctor. I was telling my brother that, and my dad said, not with those kind of grades, you're not gonna be a doctor. So it was just very, like, even to say things was very just, ugh.

Caroline Sangal 13:21

There was a tension there.

Dr. Jessie and Omar 13:22

And I didn't realize it until now because now I'm trying to be more curious. I'm trying to get more involved and trying to get my hands into all the things that we're doing with ASQ, And it's like, sometimes I'm like, I feel like overwhelmed and like lost. You know? And I'm like, what can I capitalize on? What can I focus on that I am good at? You know what I mean? Yeah. And then that leaves all the it to him. And I feel terrible because I wanna be helpful.

Caroline Sangal 13:48

So I used to feel bad or terrible when I was like, some things that I'm thinking like, oh, come on, I should be great at this and I'm not, right? Or like numbers. I freaking gotta have a PhD in science for God's sake. So like numbers I can do, right? But let's say like remembering numbers, like my phone number, like my anybody else's phone number, right? Yes. What time were my children born? Like I just don't know. And so those kind of moms that were like, oh, it was 6 52 on a Wednesday morning, and I'm like, you know what? My kid was freaking chopped out of me emergency. So he's healthy. I don't know what the freak time that was. Or my phone number. I used to have a sticky note. So if I was leaving a message, I would do that. And I used to feel so bad, what a you know, imposter or horrible person I am, or I think I'm smart and blah, blah, blah. And then when I took one of the assessments that I now offer the Highlands Ability Battery, and I saw, we are all given gifts and talents. We know that, right? Theoretically, like by God, by universe, by whatever you wanna say, by somebody, genetics, who cares? We all have certain stuff poured into us on purpose. For a purpose only we can do and for a reason, right? And it's okay. I didn't get that one poured into me in that respect, but I had others. Mm-hmm. And so that sets me up for other things, like maybe dealing with people a little bit more than dealing with accounting and bills and invoices. so I think leveraging, especially you guys as a partnership so that you can, like when you're doing things that's aligned with how you're wired, it feels energizing. It feels exciting. It feels good. Mm-hmm. And just because you can do something doesn't mean you have to. And so by default it's just gonna fall on Omar. And I don't know if you got that poured into you or if you're just taking it for the team, but how about when you were growing up? Like, tell me a little bit about that experience with you.

Dr. Jessie and Omar 15:41

Yeah, um, um, you know, it's interesting 'cause I'm listening to Jesse talk about her childhood and stuff. And over the weekend, um, I'm gonna be doing a presentation on ACEs. And ACEs are all these adverse experiences that we have as children. And how did they manifest as we go through our life. Right? So, uh, growing up, my mom has always been an entrepreneur uh, she was a hairdresser uh, all her life, and always worked, only worked for someone maybe once or twice in her life. So all I've seen from her was always that independence, you know? Yeah. That idea of doing her own thing but she'd always encouraged me to go to school and get a dedication. And she always used to tell me, Omar, I don't have money to give you all like all I could give you is an education, which is a bad advice, number one, because most people don't understand what the word education means and what the concept of education really is. So when I was growing up, my aunt was, she was a nurse. she grew up with us, a lot of my immediate family were professionals. Now they were in Dominican Republic, which is, an island in the Caribbean but nonetheless, they were professionals, nurses, entrepreneurs, people that owned their own business. My grandfather had a lot of land, so not wealthy in terms of money, but wealthy in terms of, they always worked and they always did their own thing. They never worked for anyone. Moving from Dominican Republic to New York City to South Bronx when I was 10. I was fortunate enough to be a Boy Scout leader, right? So I became a Boy Scout a couple years later I became a junior assistant scout master, and I was introduced to two people, Ken Mullen and Betty Medina. And this is when a lot of things changed for me, because I want you to think about a 13, 14, 15 year olds having to plan a Boy Scout. Entire year, including the summer. Downtown Manhattan at the AT&T building boards room. So my experience was at that early age was planning programs from beginning to end, setting a goal, understanding what could go wrong, understanding all these different nuances about strategic planning, about how to think, how to set goals, and then being able to teach that at that early age. So I was exposed to that as a very young age and being 14, 15, 17 and being in charge of like 120 kids. And you're responsible for manifesting and not just me, it was just a couple of us that were the leaders. Yeah. And Ken put us in charge. There was a certain level of confidence and cockiness that at 17, 16 years old don't understand. Right. So here I am and Ken encouraged it. I was talking to one of my friend Danny, we were talking about this one day um, we were going on a field trip. So Ken, Danny and I planned a field trip. Ken has cancer at the time, so he was getting treatment. So he asked a parent and adult to make to go with us because they needed an adult. And then the parents started getting a little mouthy with Danny and I, and you just call Ken. Ken got on the phone and Ken told them the only reason why you're there is because you are over 18 and they're not, so you better listen to what they tell you. Right? So that was a pivotal point in my life because he gave me the confidence. Um, But also what I saw with a lot of my friends. And Ken was a military man. He was a former New York City police officer. So the that idea, the para military concept was in there, but I had a lot of ACEs up to that point, and I, in retrospect, looking at it, so I went to school to go to criminal justice, and I wanted to go into the FBI but there was something inside of me that they just, that wasn't it.

Caroline Sangal 19:31

Why, how did you get that idea then? Was it because of your mentor being military, being a police officer, and you're kind of thinking in that realm? Or did you know anybody that had done it or just it looked so cool on TV? Where did that idea even come from?

Dr. Jessie and Omar 19:48

I love Point Break the original with Keanu Reeve. Practic Swayze. So I wanted to be Keanu Reeves from Point Break. How about that?

Caroline Sangal 19:57

Okay. A lot of people, he was pretty, he was so cool in that, right? he was such a cool, cool guy.

Dr. Jessie and Omar 20:02

You know, "Vaya con Dios" right. You see movies like Seven, those investigative movies and you see all that. But it was interesting though, because I never wanted to go into the military. I remember Ken gave me this book to read, and it was called Outbreak and I, they made it into a movie with Dustin Hoffman. And this idea of rebelling against the system, right? Mm-hmm. You know, you have your marching orders, but you know that if you do this, this is wrong, right? Yeah. And you have to do whatever it takes to stop it in an environment in which you shouldn't do that. So Ken was always putting all this devil advocate things right? Like, what are you going to do? In addition to that, we used to go to Catholic church on Sundays, but afterwards we will have these in-depth conversations about morality and what does it mean to do this and things like that. So, as that was already part of my makeup. But when I got into college and I did great through how high school I always was top of the class. I graduated number five on my class.

Caroline Sangal 21:00

And your class must have been big then being New York City?

Dr. Jessie and Omar 21:03

I think it was like 400, 500 in our class. Oh, wow. And, we have certain gifts, I couldn't study. I can't, I'm always fidgeting and moving so I was always good at remembering things. I love math and history and literature, like I love that part but I was never really good at focusing. So when I got to college, I struggled a lot, particularly because it was that time I was in that gap in which you were, you went from doing everything manual to starting using scientific calculators. So I will do all my work manually, but I wouldn't get good grades because you needed to use a scientific calculator. But I'm like, I got the answers right. He is like, Nope, but you didn't follow the process. So there goes that rebelling yeah. part in me, which I get from my mom and I get from Ken and I get from Betty so in my twenties I struggled quite a bit just to find my place. Um, I went into a spiritual journey, so to speak um, um, I was very depressed once I figured it out. Criminal justice is not for me, but I have a semester left in college what am I gonna do? I'm gonna just drop out. No, I finished it. You feel like an empty accomplishment?

Caroline Sangal 22:07

Ah, yeah. Yep. Okay. catch Jesse back up to this timeline, right? Because last we left you were, you were in Rockford, Illinois elementary. But tell me about high school then. Like when, 'cause I think you moved.

Dr. Jessie and Omar 22:21

And yeah, we did. So when I was 14, my aunt was, um, unbeknownst to me and my brother, my aunt, who was everything to me, everything, everything in the world like I loved her so much. She was that person that really made me feel good like she is the one that said, your Afro is so cute. And I was just like, oh my God. Mortified. 'Cause I had short, curly hair and it was like Afro, I didn't know how to take care of it. I was chunky. And she was like, you're beautiful. Let me do your eyebrows. And she just did all the things I felt so connected to her. So when we moved to Florida, I was excited about it. I didn't know she was dying um, and the first thing that we did was we got off the highway and we went straight to the hospital and me and my brother were like, what are we doing here? And we go upstairs to the IR or to the um, ICU and we have to put on gowns from top to bottom. Everything has to be covered, hands, feet, everything and um. it turns out she's in the hospital dying. And it was a shock. And so this is the way my parents were.

Caroline Sangal 23:26

And so your parents, it sounds like there was not a lot talked about. It was kind of like a need to know basis. And there was a lot of things that you, they decided you just didn't need to know.

Dr. Jessie and Omar 23:34

And so that's where I found out that my aunt was transgendered, which blew my mind 'cause I again not talked about. So I don't have any idea what this is. And, um, I was devastated by her death. And I'll never forget, me and my mom and my mom and dad in the front, my dad was driving me and my brother in the backseat and I am crying, like boohoo crying, like baby crying. It was really bad. Yeah. I was just devastated. And I'll never forget us driving out and my mom she just, this reaction from her, she turned around and she slapped me and she said, stop crying, and it was like we weren't allowed to like yeah. process even our feelings or talk about it, you know? And so that stuck with me for a long time. And of course, being, um, not having a lot of encouragement, like the, there's such a difference as to how Omar grew up, which it's a beautiful thing. He had all this encouragement and trust and we didn't have a lot of that. So it was very much me trying to fit in and belong anywhere I could belong. And so that's how it was all through high school. I didn't try new things for fear of failure. The things that I did try,

Caroline Sangal 24:43

Where did the running come in? So I, because I heard something about you being like, becoming, this was a runner. Amazing. Like, come on, cross country. Like, I don't know. I, for me, if I was running, then I would start to be sweating and I would start to feel uncomfortable. Like I loved jumping in water. Yeah. Because that was different. But the other, like, I didn't realize till way later that was connecting to trauma responses of not wanting that feeling and that feeling also came with running or exerting without water, But like where did that, how did you just like?

Dr. Jessie and Omar 25:17

So I wanted to get involved in something and a friend of mine, her name was Jania, she was like, you know, I'm doing this thing. Why don't you come? Why don't you join? And it was like an afterschool thing. And that's how I got, so it wasn't even on the books. We didn't get like a grade for it. It was just something that we got involved in. It was like an afterschool program. So I started, I did not wanna fail because I was like, I'm gonna be good at something. I'm gonna do this. And I started to really like it. I started to like this. Oh my God. I just ran a mile. Oh, wow. I just ran two miles, and then increasing my miles and doing this whole like it was a running club an afterschool club. And the coaches were really cool. It was different, and they were really hard on us but I found myself doing what I was doing because I was liking this. You're doing great. Keep it up, Jess. Keep going, keep going. And I wasn't getting that in any other area of my life. Gotcha. Except for there from these coaches. There was two coaches, a man and a female, and I was just like, really just wanting to belong to something. And so I took this up as a, as a sort of to, to like just buy that po that, that moment or, or to fill that void. You know what I mean? And it was great. It was fun and I continued to do it, as I became an adult. I loved to run, I ran whole marathons. Not on the books or anything, but still did it with this boot. And it was great. It was really, a really good, exciting time for me. But I didn't have my parents come to any of these things that we put on any of these events. They didn't come and see me do these things. It was just kind of like, Jesse's just

Caroline Sangal 26:57

that was your thing, but you found this like freedom and encouragement and release and maybe community With other people striving.

Dr. Jessie and Omar 27:05

Yep. It, but wasn't a conversation ever though. It wasn't like that. It was just that exercise moment. I don't know if I'm explaining it very well, but just that moment of I'm achieving something in that moment, but I'm not talking about what I'm feeling and we're not having these discussions. So it's kind of temporary

Caroline Sangal 27:22

and still there's so many things that have to move through us and so without even consciously knowing it, you're giving space for maybe some of that process and then when you started working, what kind of jobs did you take? what did you do? I'm so curious about how this went out because I think after graduating high school, what were you doing? Let's talk about that a little bit.

Dr. Jessie and Omar 27:48

So for me and my family, it was, again, school wasn't encouraged. I wasn't encouraged to go look at different colleges. I wasn't encouraged to like, whatever it was, you need to get a job because when you're 18, we're done taking care of you and you need to figure things out um, and I'm making it sound really bad, but it's kind of like that's really what happened. I wasn't, it was almost like me and my brother were burdens and it was, okay, we've done our time. When you're 18, let's go like chop shop. Time to go. So for us it was, oh, well damn, we need to get jobs So I got my first job at Burger King when I was 14, when I first moved down 'cause my mom and dad were like, we're not buying clothes for you anymore. You need to buy your own clothes. And then as I went through high school, I worked at different places. like a, something that was, oh, it was called Builders Square. I don't even think it exists anymore as a cashier, I worked at like Winn-Dixie. I did things like that and then my high school and right after high school I got a job as a, like a hostess or a waitress at the Breakers Hotel here in Palm Beach. And I was making crazy money, but my desire to belong and my desire to be needed and my desire to be looked at as somebody who was accomplishing everything, I spent all my money on my friends and on stupid stuff like crazy ridiculous. I wasn't even thinking about finances. And we didn't get really taught about finances and how important it is to save and budget and look at what we were doing and how, you know what I mean? It wasn't that whatever. And I didn't have mentors and people that said, Hey, Jess, calm down, you are spending all your money. Relax, look at this, or do this or do that. So it was me just kind of trying to figure things out on my own, you know, as I went along. So I worked at The Breakers for about a year, and then I got totally like rebellious, just going to the club, doing this, doing that. I was just, when I look at that point in my life, I think I was just in a fog, just trying to just let loose and just have fun, go through, you know, friends and having some boyfriends and whatnot and so on and so forth, and just, not even, it's just like a fog, seriously, when I think about it, you know what I mean? Because you're bringing up a lot of memories for me. But when I look back at it, I mean, I was like sneaking out my window to go out to the clubs. My parents, one day my dad found out that I snuck out and I came back and I can see it's completely dark in the front of the house and all I see, 'cause he was a smoker, is this orange dot, and it was bright for a while and I knew he was upset and he told me, you have to move out. That's enough. Oh wow. You're home late. It's enough. This is a third time. And so it's almost like I pushed that to happen because I knew it was gonna happen. I was gonna get thrown out if I didn't respect the rules, but I was just, I can't even put a finger on what was going through me. I was just in a fog. I was just so desperate to belong and to be needed and to be like, somebody acknowledged that I'm doing something right. So I was like, if I'm not doing anything right and I can't get a knowledge, I'll just do everything wrong. He acknowledged me then, does that make sense? And I can't, I'm not a therapist, so I'm not really sure how to kind of determine what that was. But it was a lot of really trying to, a lot of people pleasing. So then I got pregnant. And, I wasn't living at home. I was kind of jumping from couch to couch. I did have my own apartment at one point, um, with a friend that we shared, you know, and it was crazy just doing all kinds of crazy stuff all the time. And, I ended up getting pregnant and then I ended up marrying this guy six months later because that was the right thing to do. You can't have a child outta wedlock, like, how dare you do this to our family? Um, And it was a very loveless marriage. I didn't want to get married. I was like, we can just have this kid together and not be married, can't we? And, they didn't want that, so we ended up getting married and, uh, yeah. What else? What am I missing?

Caroline Sangal 31:48

Okay, so now you have a child. How that affect your outlook on and when the baby came, did you have to work? Did you choose to work? what happened there?

Dr. Jessie and Omar 31:59

I did. Yeah. I, we did, I did have to work. I, I went to school to be a medical assistant while I was pregnant, and the program that I was in was like an eight month program.

Caroline Sangal 32:07

And so how'd you pick that? Was it maybe seeing stuff with your aunt

Dr. Jessie and Omar 32:12

No, I think it was just me thinking this could be a way into the medical field

Caroline Sangal 32:17

and you had thought about being a doctor.

Dr. Jessie and Omar 32:19

And I was like, I don't know. Again, just my mom and dad were like, you need to do something. Something's gotta give and I needed to get a job, and this person that I was with, you know, wasn't making a lot of money. We were both just getting started, you know? Yeah, yeah. And, uh, so I became a medical assistant and put my son in daycare, and that's what I did for years. I was a medical assistant for a couple years. I was a medical assistant until one day I just wasn't. And I ended up staying home with, at that point, I had three kids. I had twins. It was way expensive to put three kids into daycare, so I had no choice but to stay home. And it was sort of, I was trying to get out of this marriage at the time, and then I found out I was pregnant and I'm like thinking I'm having one additional child, then I'm having two and I'm like, I'm so, I was gonna say the F word. We're so, I'm so screwed. Go for it. I was gonna say, I'm so fucked. You know? I'm like, I'm stuck here in this relationship that I don't wanna be in. My parents really liked this person and it was never this, it was like I was doing something right because I got married to this person who was doing things right. He was working, making money at that point. And here I am, just kind of like, stay at home mom, pregnant.

Caroline Sangal 33:30

Had you ever seen, did you have like cousins or something that had little babies? was your child the first little baby that you had to.

Dr. Jessie and Omar 33:39

Yeah, pretty much. Didn't know how difficult it would be. We didn't have that program where they give you the fake baby and the baby cries all night 'cause if I had that, I probably would never have gotten, had never, I would never have done this, um, but I didn't go through that. We didn't have that experience in school. You know, I, I was just very careless and just doing things, just going with the flow of things. It was very, just like I was having this out-of-body experience. I'm not even present. I'm in a fog for so many years of my life up until literally when I met Omar, when things started to kind of open up for me a little bit. And even then it was very, I need to get a job. I need to get an education. I gotta do the right things, I gotta pay bills. I gotta do, you know, then I'm, yeah, more all.

Caroline Sangal 34:23

But how did, how did you transition from like Yeah. all of a sudden now you're full-time caregiver for three children. and you didn't have any models of that? Prior to. Yeah. How did, how, how were you not? Yeah, yeah.

Dr. Jessie and Omar 34:46

When I reflect on that time, Caroline really, that was probably the most unhappy part of my life. I'm getting emotional. It's probably the most unhappy part of my life. You have kids.

Caroline Sangal 34:58

You get P-P-D also because I felt like I had PPD, but just going from the growing up. You know, if you, if you showed emo, Although we said I love you all the time, right? But, and, you still couldn't necessarily feel. Certain feelings were allowed to be shown and others were not. And so I didn't, anybody that had mental struggles. They were crazy people, right? And so I'm sure as heck didn't wanna be crazy people. So I wanted to be known for smart, but not for crazy. And I didn't even think, and then I didn't wanna get anything, do something wrong or whatever. But yet I was not myself.

Dr. Jessie and Omar 35:42

I was going through it. I literally can reflect on those days. And I have curly hair naturally. And usually I'll get it to a point where I'm like, okay, it's time to cut my hair and take care of myself. I had hair past my butt. and that to me was kind of gross. No judgment to anybody who has their hair past their butt. Just me. That was gross. I hadn't taken showers in days. Not like me at all.

Caroline Sangal 36:04

Where was the time though, if you are the sole person and now there's three things and like, 'cause somebody always needs something. Yeah. Right. Or is cry like, And I don't know, like with the first kid, I didn't want him to cry at all. Then with the second kid, I'm like, I'm gonna just strap you in this bouncy chair and you can just have at it while I brush my teeth. You know? But, but still, no, but, But like before that there were days that you like, it doesn't make sense until you're in it. Because without having kids, I'm thinking like, are you kidding me? What do you mean you don't have time to brush your teeth? And then I'm like, because nobody tells you that when you're nursing a baby. And it's like, oh, well they eat every, you know, one to three hours and that start to start. Yeah. Okay. So if you got a grazer, you are not having a time for your yourself.

Dr. Jessie and Omar 37:31

And, and so then you have three kids, each of them are different in their own ways. with the twins, when one would poop, the next one would poop. When one would puke, he was the next. It was when one was sick and it was like constant chronic sick. All. Oh yeah. They had their tonsils removed, they had their adenoids done, they had all kinds of shit done. It was crazy. And I was doing this by myself. You know what I mean? I was like a single married woman, literally. And it was hard. And I don't think that, you know, sometimes my son will say, oh, you just don't understand how he's got one kid. Yeah. It's hard for me to it. and she doesn't cry. She doesn't cry either. She does. She's a fun baby. My granddaughter's a fun baby. Fun and the thing, But I know it's hard, but dude, multiply that times three. And then talk to me about,

Caroline Sangal 38:22

And being young and being super young where you're in so many cases, just trying to grow up yourself. Yeah. Oh, totally. And now you've got responsible for other lives in the world.

Dr. Jessie and Omar 38:31

By the time I was 23, I had three kids. Wow. And I would begged the gynecologist after when I was gonna have the twins, I was like, please, please, can you fix it down there? I can't 'cause I wasn't supposed to even get pregnant with the twins. I was cold. I had a cold and I was on the pill and I was on antibiotics. And somehow or another, it didn't get to me that you're, you know, you need to use protection 'cause something could, you could get pregnant. You're on cold medicine anyway. I don't regret having the kids, but it was a very tough time in my life. And a lot of those days just blended together. I remember when the kids would get on the bus, I would go right back to my bed and sleep until right before they had to come home because I wasn't sleeping. Yeah. Yeah. Mountains of laundry constantly, um, sick kids constantly. It was just like. The only thing that I had was a phone to talk to people. And I didn't even really have that many friends 'cause they're like, oh, she's got three kids.

Caroline Sangal 39:25

That's right. Right, right. Because yeah, if you're one of the first ones in your friend group to have kids, all of a sudden you become untouchable.

Dr. Jessie and Omar 39:32

That's it. You know? Something, something. Yeah. Totally untouchable. And so I didn't have a really big support system. And even when I left my ex-husband, everybody that I knew turned their back on me because somehow he painted this picture that I was the bad guy and never took accountability for his stuff, you know? And what about what you did? None of that mattered. And, um, so I literally just did.

Caroline Sangal 39:57

And you weren't the type to be telling anything of your thoughts and feelings

Dr. Jessie and Omar 40:02

Even my parents felt that I was wrong for leaving him, I mean, even my parents chose him over me and didn't support what I was going through. It was just a really dark time for me because who do you talk to? And then how do you share what's happening when you can't even put the words together to figure this out? Because it's not normalized. It's not something that people talk about. You don't have any friends, you have no family support. It's like I was alone.

Caroline Sangal 40:33

And still you had this inner inside you realizing the pain of staying the same is worse than the pain of leaving. And so you chose yourself, your own wellbeing that of your kids. And then when you went back to work, 'cause sometime you had, would've had to go, then what did you choose to do? Were you still doing medical assisting related things or what happened there?

Dr. Jessie and Omar 40:59

So what happened was, I did this exodus and I knew, and I was making a conscious decision at the time I knew that if I leave I cannot physically support financially. I can't support my children financially I also knew that if I stayed, I would rather just be dead. I wasn't a good mom. I wasn't good to myself. it was a really tough decision to make. So I left and I left the kids with him because I needed to just leave everything in everybody. So I did literally an exodus. I left the state, I went to another state, and in that year I discovered a lot of things about myself. I discovered that, you know, I'm not so bad. I discovered that I do like things even though I don't know what they are. Yeah, I discovered a lot of things. Most of all, I discovered that I could take care of myself rather than depend on somebody to take care of me. So I learned how to do that, to gain my independence and not be relying on other people to take care of me. That was the key thing. So when I came back, made the mistake of going back to him because I really wanted to be with my kids. Yeah. But leaving him the second time was much easier than the first time 'cause I was like, I have a car, I have a job but the job that I had was not in medical assisting I think it was like I was doing like cashiering at like Walmart or something. And then I got a job at the Boys and Girls Club and at this point I had separated from him. And that's where Omar comes into the picture.

Caroline Sangal 42:31

I met him at the Okay. I was wondering how it line. So, but, but when you, when you left, and that must have such a difficult decision that that's your only option. but if you had stayed, I might not be talking to you today. So I'm glad you did what you had to do. Because You had to break free for a moment. To take care of your own self. You had to be able to have the time to put on your own oxygen mask before trying to help others. How old were your kids at that time?

Dr. Jessie and Omar 42:59

So Jacob was, I'm gonna say he was probably four or five, and the twins were about three. They're two years apart. So yeah, they were pretty young. they were, outta diapers and whatnot, and he had a lot of support. So he had a lot of people that came in and I'm grateful that those people were there when I was not there. But I literally needed to, like you said, I needed to put my own oxygen mask on. I was like dying. I was suffocating in that life that I was living. but when I came back again, I had this freedom, this realized freedom of I can take care of myself, I can do this, I can balance my own checkbook, I can do these things, where I wasn't doing any of that before. Like he took care of me.

Caroline Sangal 43:39

Was there formal support that you got? Like had you broken into like, okay, there's people called therapists that could be great, helpful, or you just were on your own sorting it out?

Dr. Jessie and Omar 43:51

I was on my own at that point, but when I did come back, I did get therapy.

Caroline Sangal 43:55

How did you know that was a thing though?

Dr. Jessie and Omar 43:58

I don't even know, to be honest with you. I have no idea. But I do recall going to therapy, but I gotta tell you, sometimes there are no offense again, but I'm gonna say it, some therapists suck.

Caroline Sangal 44:08

They do. They, so, they certainly do.

Dr. Jessie and Omar 44:10

Some therapists suck.

Caroline Sangal 44:11

And I feel so bad about that. and some people suck too, right? but then it gives a bad rap for others. And if you have somebody in such need of help and then you don't get, and so it's so trial and error sometimes. It's like, who has time for that? it's already so hard to be vulnerable. And then you like try to trust somebody and you realize that they suck. they're try to do it all over again, you know?

Dr. Jessie and Omar 44:35

It's almost like I was going to this therapist and I'm going there for daddy issues 'cause this is all stemming from this missing peace in my life of not being encouraged, not being loved, not being told you're beautiful, so much of this ties into that, when I think about it, like not getting the encouragement that I needed to figure out finances, to look for a career that would be good for you. We did that for my kids like I encourage them, Hey, you have choices, you can do this, this, and this. this choices and consequences. like this whole methodology that we gave them and they landed in a space where they're completely independent right now. Completely. they're in service, public service. they're firefighters and police officers but they made decisions based on the encouragement and when they failed a test, it's okay guys, just pick it up, study harder. I didn't get that. So I was giving what I didn't get, but now I'm realizing I'm over overcompensating in this whole nurture area. I wanna be accepted by my kids. Now I gotta do this because I'm scared to lose my kids because I was a bad mother. Like, It's this whole vicious cycle that you go through. Until you start to sort things out and understand that you have to have a balance in these different areas. Right. Something that we talk about in ASQ. But, I'm not sure if I answered your question.

Caroline Sangal 45:53

Thank you so much for sharing that beautiful part of your journey. It does, at the time I'm sure it was just freaking terrifying and exhausting it. Seeing what you guys have built beyond that. It is beautiful from this viewpoint, for that one it must have been terrifying. Okay, so Omar, let's catch this up 'cause you think you're gonna be a FBI agent and then you realize, nah, it's not like the movies or tell us what happened there. Well, not everybody was as cool as Keanu.

Dr. Jessie and Omar 46:26

Nope, nope, nope. I remember, I enjoy a lot of my criminal, criminal justice classes. they were very interesting, learning about organized crime, terrorism, and all this stuff. It was really cool but I remember it was my senior year, first semester, we were doing a project and then this FBI agent came in and I was just like, Ugh. No.

Caroline Sangal 46:47

What was it? Let's, he was just articulate that a little bit more. What was it about that? Just funny.

Dr. Jessie and Omar 46:51

He was just a prick. He was just like one of those guys that it was like, this is what law enforcement is. And again, it's like I just making a generalization, but just, just seeing what he stood for and the arrogance and the thing, it just wasn't me. Plus most people don't understand that the FBI, it's not really you know, guns blazing type of stuff. Right. Uh, a lot of the FBI, what they do is really accounting and Yeah. and investigating white collar crimes and a lot of tech, a lot of that stuff, which is, I've learned that's not my skills. It's not one of my innate things.

Caroline Sangal 47:25

You seem to kind of maybe love and need that people centered environment. Exactly. The opportunity to be interacting face-to-face with people yes. as much as you can.

Dr. Jessie and Omar 47:38

So what happened at that age is that confusion steps in you know, because it's like, wait a minute. by that time, um, I was an assistant manager at The Gap. I went through their, their internship program.

Caroline Sangal 47:50

Were you best dressed?

Dr. Jessie and Omar 47:52

I was, uh, I was actually called Gap Boy in Orlando. Yeah. Yeah. So I was known as the Gap Boy. Um, but I was, I went through the internship program um, but that time I already had my own apartment. Um, I, I had every, I set the goals because again, I was taught to set goals. during that time, it was a very, unlike Jesse, 'cause again, what she went through, it's parallel because it brought us together. But at that time, that idea of who am I? Really came in. You know? And I was fortunate enough that,

Caroline Sangal 48:24

and how old were you at this moment?

Dr. Jessie and Omar 48:26

19.

Caroline Sangal 48:28

See, there's normal times people start questioning their life and their career, and they happen at predictable stages. Yes. And they can kind of shift a little bit, depending on if you bring somebody else into your world or maybe people come outta your body. Um, if we can, can skew those. But one is around 18, another could be around 22 to 26. Mm-hmm. And so both of you though, had these things, you know, and, and you can have by choice or by force or, but it's just, it is a natural time of questioning. And so here you are and it, but you kind of paid attention a little bit, right? Sometimes people override it. Yes. By, what they should do. You know, or.

Dr. Jessie and Omar 49:09

And like I said, I was fortunate. I mean, like you mentioning, what you're mentioning is Eric Erickson stages of development and the crisis that happens in between if you don't understand that. Right. So, but again, I was fortunate because I was always challenged, if I don't know something, there's something out there or someone out there that knows it. Right? So, um, I remember, and I tell people, this is one of the stories that was uh, my, um, formative in my life at that stage, right? Uh, my mother, you know, right away when you are in our culture or whenever something's going on, it's like, oh, you gotta go to a doctor. Right? So she takes me to a neurologist and I'm like, look, I don't want to take medications. I don't know. I know that I'm not crazy. I just don't know what I'm going to do with my life. I'm lost. I'm lost. I just, that's, that's what I know, what I know that I'm lost. So he laughs at me, he goes into his desk, gets a prescription pad, and then he starts writing things down and I'm rolling my eyes like, dude, I just told you I just don't know what to do next. So he writes these things down, he gives me the prescription and he says, take this. And he's like, I completely understand what you're saying. but he has three books. So the three books that he gave me on the pad on the prescription was number one, 'Awaken the Giant Within' by Tony Robbins yeah. Yeah. which is a good book, but I wasn't really crazy into it. I was like, ah, okay, whatever, the second one was 'How to Win Friends and Influence Others again', it was okay. It's a great book, but meh, that's not my thing. But the last book was the one book that really transformed my life, and it's called 'I'm Okay, you're Okay' by Thomas A. Harris and this idea of transactional analysis and the different personalities of the different things that you have, the adult, the parent, the child, and being able to understand that but the one thing about that book at that age that really hit me was that idea of forgiving and primarily forgiving your parents. Right. Because like you mentioned earlier, it's like they, they only do what they know and they only did what they knew. So at that point, I grew up without a father. So one of the first things that I did, well, actually the first thing that I did was write a letter to my mother, because her and I, although I was doing all these different things now, I'm no longer her baby. I'm doing all this stuff. So I lived two lives, right. At home, I was just a child, but outside, I'm this person that is getting awards from the city and all that stuff, and it was that conflict. And then I had a girlfriend, though, that was another conflict. And I wanted to do my thing and that was another conflict. So I had to write that letter for her, then I went to seek out my father and confront that situation but then after that, after doing all that, it's like, okay, what am I going to do? So I said, well, I finished college. I got a degree. Why do I don't, what do I know what, how to do? What do I, what am I good at? Oh, you know, how to work with young people. So I got a job at the Boys and Girls Club And this is back in 2001, 2000 actually but what ended up happening is that although I enjoy that, there were still those splintering questions as to like, who am I? Why am I here? What is my purpose? You know, like deep down inside and I really didn't articulate it. And Jesse used to tell me that it's like, all you do is just read books. 'cause at that time, all I did was just take information and take information and I went into quote unquote a spiritual type journey, so to speak. Learning different ideologies, learning different modalities of spiritual things. I took classes in Miami for a place called the Kabala Center. I ended up working there. I actually ended up trying different careers. I worked as a door-to-door salesman, which was something that, although very challenging, it was extremely beneficial to learn, right?

Caroline Sangal 52:52

Absolutely.

Dr. Jessie and Omar 52:53

Because he's like, how could you build a relationship in 10 seconds?

Caroline Sangal 52:57

And you gotta be real comfortable with rejection too. And just be like, next, all right, you said No, I'm gonna go to this one. But I sometimes I feel like that would've been a good thing to try. Although I was always thinking that there was a boogeyman or somebody was gonna get me, so I didn't really explore a lot 'cause I don't know, just when I'd get my nerve up to go and walk on my own, then it's like you read a story about some crazy guy, something on the trail i'm like, well, fuck, stay back home again. You know?

Dr. Jessie and Omar 53:27

And you know what I've learned about that is most people are very nice. The people that you may think will not be are the ones that are super nice, right? I remember this one story I was sitting, I think it was somewhere in West Fort Lauderdale, right? And it is like you know, uh, redneck town, right? The confederate flag, no trespassing. And I'm like, I'm going in and I knock on the door and the guy says, what do you want? And I'm like, oh, I'm here, blah, blah, blah, blah, blah and he's like, you want some steak? Aw. Just like that. Nice. Just like that. Yeah. Because, you know, we have these preconceived notions about people, and by doing that job in particular, number one, you learn the skills of selling, which is important because it's our relationship building. But again, for me, it was just seeing like, people are more like that they are different if you really look at it. that job taught me that, right? from there, um, I worked, um, with um, I started actually a call center at the Kabbalah Center I worked with one of the teachers and I started a call center there. Then I also work with a good friend of mine, Fred, who's part of our organization right now and IT and some technology stuff and, and all.

Caroline Sangal 54:42

That's where you learned it.

Dr. Jessie and Omar 54:42

That's what I learned it from, right? So I've been getting a lot, I got a lot of those skills with the web design and all that, HTM, all that stuff I'd learned from there I worked in sales again with Comcast. But then finally there was one day, and Jesse kind of like started noticing that I was getting a little bit, I was depressed 'cause yes, I was making great money. Comcast making, in sales.

Caroline Sangal 55:06

were you inside sales? Outside sales? Where was your workplace?

Dr. Jessie and Omar 55:09

I was outside sales in Comcast and we were making, I was making like $80,000 a year, working maybe like four or five hours a day, so the rest of the time I go spend the, reading and all that stuff, but it was, it was very unfulfilling, you know? Because it wasn't, you know, it wasn't like the thing that was calling me. So there was always that splintering, like there's something more out there than just maintaining yeah. And I needed that because we had kids, we had to make sure we maintain the house and all that stuff. But then one day she just said, you are so unhappy. And she called someone that we knew from the past that worked at the Boys and Girls Club and I, and they say, Hey, Omar wants to come back. And I went from making $80,000 a year to making uh, $7 and 45 cents an hour, uh, part-time.

Caroline Sangal 55:55

But you can be outwardly successful by many external measures and inwardly unfulfilled. And then at what cost is that? So that's beautiful that she saw you. She knew you, she knew what had been good for you. And if you guys met at the Boys and Girls Club, to be able to find a way of like, how can you holistically be you, your best self and then be able to build from that.

56:19

You've just listened to part one of a two-part episode with Dr. Jesse and Omar, the early chapters, and in part two, we will pick up with how they met, how the relationship deepened, and what happened when real life applied pressure, career detours, financial stress, and the kind of internal unraveling that forces a rebuild. Thanks for listening to your next success with Dr. Caroline Sangal. Remember, authentic success is yours to define and includes aligning your career to support the life you want.