From Single Mom at 18 to Attorney: How to Reinvent Your Life With Jessica Lynn Silva

Your past does not decide your future. Jessica Lynn Silva grew up poor, became a single mom at 18, and still earned 4 degrees with no student debt and built her own estate planning law firm. She shares how she kept moving when she was terrified, and why fear became her green light.


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What you’ll learn

  • How Jessica earned 4 degrees, including law school, without student loans
  • What it took to work full time, commute 3 hours a day and study at night as a single mom
  • Why she forced herself onto pageant stages and speaking stages as an introvert
  • How she built a profitable law firm through relationships and referrals
  • Why taking action builds confidence faster than waiting until you feel ready

Episode chapters

  • 0:00 Meet Jessica Lynn Silva
  • 2:35 Growing up with love but no money
  • 7:52 Single mom at 18 and life as a military spouse
  • 10:25 Success is the best revenge
  • 15:28 From single mom to attorney
  • 20:31 The setbacks that change you
  • 23:04 Forcing yourself to face your fears
  • 28:13 27 years building a law practice
  • 30:51 Why you have to get moving
  • 33:26 Growing a personal brand as an introvert
  • 38:35 Seeing fear as a green light
  • 41:12 You don't need a perfect plan

About Jessica Lynn Silva

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Full transcript

Read the full transcript of this episode

Heather Monahan [0:00] Hi, and welcome back. I'm so glad you're here with me this week. Okay, you're gonna love our guest today. Let me give you a little bit of background on my girl, Jessica Lynn Silva. She's an award-winning estate planning and probate attorney, mediator, and entrepreneur, helping individuals, families, and business owners protect what matters most. As the founder of the Law Office of Jessica Lynn Silva PLLC, she blends legal expertise with strategic insight, guiding clients through wealth preservation, ooh, that's a big one, legacy planning, and life transitions with clarity and confidence. Beyond the law, Jessica is a trusted coach and speaker for high-achieving individuals and professionals.

Jessica Lynn Silva [0:28] Thank you.

Heather Monahan [0:37] who are navigating growth, reinvention, and leadership. Her work bridges strategy, mindset, and self-trust, helping people move from survival mode into intentional, empowered living. With a grounded yet inspiring presence, Jessica is known for making complex topics accessible. while creating space for meaningful transformation. Jessica is the reigning Mrs. Hawaii International 2026 Call to Lead Woman of the Year, Marquis America Who's Who Top Attorney, Tampa Bay's 40 Women to Watch. International best-selling author of Wealth, Wills, and Winning, and the host of The Jessica Lynn Show, a podcast and YouTube channel dedicated to conversations on wealth, legacy, leadership, identity, and personal growth. Through these platforms, she educates and inspires a global audience to think differently about money. purpose, relationships, and generational impact. Jess, thank you for being here today.

Jessica Lynn Silva [1:32] It is my pleasure. I'm so excited to spend time with you, Heather. Thank you for having me.

Heather Monahan [1:37] I'm so excited to hear. Okay, so let's take it back because people see you now at the level of success that you have.

Jessica Lynn Silva [1:40] Thank you.

Heather Monahan [1:45] And like most people, they think you just — you were born like this. So take us back to actually who — take us back to the beginning, please.

Jessica Lynn Silva [1:51] Oh gosh, no. Okay, if we're going all the way back to the beginning, um, I grew up poor. So, I grew up with no air conditioning in the house, and people gave us their cars because they felt sorry for us, but they gave us their junk, not the functioning, so we had a car, the El Camino, where the brakes didn't work. And then we had a brown station wagon where my mom turned it off and it literally caught on fire. Which, when you're a kid, having the fire department come to your house was kind of cool. But I couldn't understand why mom was so stressed and crying. But, you know, so we had a lot of moments. Definitely school was one of those where we'd beg our parents to park down the road so people didn't have to see what we arrived in. So that was kind of the experience I had growing up. We knew we were loved, but money wasn't a big thing. Um, and then… so the dollar was very important, but there was no mentorship. So, Dad had a dream, but he had no mentors pouring into him. and mom, and things like that. And then at 18, I actually found myself a single mom. So, I was a single mom at 18, I knew I didn't want to be a statistic, and so that changed the trajectory of my entire life, right there.

Heather Monahan [3:07] So how did you overcome that? What were the steps that you went through? I mean, that could not have been easy.

Jessica Lynn Silva [3:13] Wasn't easy, but I have to tell you, I'm a woman of faith, so since the time I was 12, I literally have had an intuition that I'm meant for more. Like, literally, I could tell you, the Lord said, Jess. You're going to connect people, you're going to add value to people's lives, and I'm going to do something with your life. So I always felt like even when I had nothing and I was the oldest of four, so I was kind of like that mother hen to my three brothers. I just always felt like there was something just beyond the horizon that I was supposed to be moving towards. Didn't know what it was, didn't know how to get there, but I had a feeling inside me that I was headed to something, and that's what just kept me going one step in front of the other.

Heather Monahan [3:54] So what was your journey with faith like?

Jessica Lynn Silva [3:57] I was saved at 6, um, and then I was raised in a really strict Christian home, so not… it was the kind where my mom, her mom, my grandma, actually had a thing. She was a singer in a movie and dabbled in dance and things like that, and she dabbled a little bit in tarot cards. So they had a little thing. So then when my mom was saved, she went from one extreme to the next. So she went from kind of… and what happened is, apparently from what they've told me, when I was 2, my mom had a scare of breast cancer. And she thought she had breast cancer, and I guess they were giving her all of the bad signs of, you might not make it, it's really dangerous. So she prayed and said, Lord, if you're real, if you will save me, I will forever dedicate my life to you. She went back to the doctor, the cancer was gone, and she became a Jesus lover on a whole. So, to this day, I swear, I tell my mom, I'm like, Mom, I think Jesus and church are more important to you than your own kids, because. She is very full-on black and white, which is amazing, but she did kind of go to the extreme. She didn't really have a mentorship on how to have a relationship with Christ, and so she went super strict, like, lots of rules. Courtship. ATIA. Jess. So, it was so rigid, um, my brothers and I kind of didn't know what to deal with it, you know? When you… I remember one time I said, oh, that boy's cute, and she's like, Jesse, you're not going to be a slut, you're going to do this, you don't need to pay attention to that, you need to go learn some Bible verses. So it was that kind of very extreme, where you… so that… so I did ashes in my heart when I was 6 years old, but I wasn't really sure what to do with that. And then I was rededicated, I rededicated my life at 17, which ironically is what saved my life because that is where as soon as I rededicated my life, I found out a week later that I lost my virginity and I was pregnant. So it's like the Lord took something drastic. to get me off the path I was headed down. And so he did. Like he does, he will take the ashes and turn them into something beautiful, but it doesn't come without cost and without hardship.

Heather Monahan [6:09] Wow. Okay, so a lot going on at a very young age for you.

Jessica Lynn Silva [6:13] Yes. Yes. Yeah. My friends, it was my senior year of high school. So all my friends were talking about where they're going to go to college, where the dorms are, all the parties they were going to do, you know, prepping, packing, decorating. And I was literally like, I need to find a job. I need to go to college, and I have a little human to take care of. So, what the heck am I gonna do with my life? So, it took me about a good 6 years to get over missing the college experience, like the dorm life. Um, and I joke and tell people, I literally, to this day, have never been drunk in my entire life. And so when people are like, oh, my party days, I did this, I was like, I have no idea what that's like. I was a mom at 18. I did not have party days. Yeah, so the Lord probably had a purpose in there, too.

Heather Monahan [6:55] Yeah, the… I mean, that could not have been easy, raising a child on your own. So how do you go from there to becoming an attorney when you weren't going to school at the same time everybody else was?

Jessica Lynn Silva [7:03] Mm-mm. Yeah, so what I did is I enrolled in college and funny enough, right before I went to college, I thought I would just go in the military, but this shows how naive I was. And so my parents were loving and they did come around, but at that time they weren't talking to me because I committed the ultimate sin. So the church was mad and my parents were mad and it was, it was rough. So I was pretty much an island of one. Um, so I went to the recruiter's office, told him what I wanted to do, and then he said, well, when you have your baby, who's gonna be the guardian? And I'm like, guardian of the baby? I thought he was asking me to give him up for adoption. And I was like, I just went through hell to keep my son. Are you kidding me? I am not giving him up. Now, being an estate planning and probate attorney, I know what he was asking. It's when you leave, when you deploy, who's gonna be watching your son for you? I didn't know that at the time, so I went from the recruiter's office to the college campus, and I was like, I need to take an entrance exam. I need to be a secretary. I took it, and I'll forever be grateful to whoever that counselor was. She came out, and she's like, your results were outstanding. You were, like, scored so high. Have you ever thought of doing paralegal instead? And I go.

Heather Monahan [8:20] Wait, she said to you, you should be an attorney.

Jessica Lynn Silva [8:22] Yeah. No, well, first she said paralegal. So, paralegal, and I go, what's that? Do they deal with handicapped people? Because, you know, para, it just sounded. And she's like, no, they're the right hand to an attorney. And I'm like, sign me up, it sounds perfect. And that's where I did it. And these are steps from the Lord, because I started college, but then at the same time, I knew I needed income, so I went and worked for a temp agency. And when I went and worked for a temp agency, our receptionist, her name was Star. She asked what I was in college for and I told her, she's like, oh, my daughter works for Brock and Scott. She's like, would you like me to get you an interview or see if they're hiring? And so out of the blue, and granted, this was not local, this was an hour and a half away from my house that she did. So I interviewed with them, they hired me, they promoted me very quickly, so entered the world of, I commuted three hours round trip a day. I went full-time, worked all day for Brock and Scott, went to college at night, and then went home and took care of a baby that wasn't sleeping through the night, and I did that for 4 years.

Heather Monahan [9:23] All right, wait a minute. All right. I just want to recap this again because this is crazy. You worked full time for a law firm as a paralegal.

Jessica Lynn Silva [9:33] Yes.

Heather Monahan [9:34] And then you would… Commute three hours back and forth, an hour and a half each way.

Jessica Lynn Silva [9:39] Yes, round trip.

Heather Monahan [9:40] And then you would get home, take care of your child as a single mother.

Jessica Lynn Silva [9:44] Well, on the way home, we'd stop in college. So I would do all my college classes in the evening at the campus. So I would go… I lived in Mount Olive, I'd drive an hour and a half to Raleigh, and then halfway from Raleigh, I'd stop in Smithfield, go to college, then continue back about 11 o'clock midnight, I would be going, yes. I would… yeah, there was times… I have notes still from that school where I'd be so tired, my notes would go off the paper, because it would be… I'd be in class at 10 o'clock at night.

Heather Monahan [10:10] Because you're falling — you're literally falling asleep while you're at school.

Jessica Lynn Silva [10:13] Yeah. But I just kept knowing, like, to me, there wasn't any other option. I was responsible for another human life, and I wanted him to be proud of me, and because I was so hurt. from the church and the other people, it's like, you know where they always say the best form of revenge is success? So I was like, oh, that's okay. You guys can judge me, but that's… I'm gonna go make something of myself, and I will make, like, proud, so you guys will eat your words. So that was kind of my inner fire. So when I was exhausted and tired, those were the things I held on to.

Heather Monahan [10:46] When you look back now, can you even believe that you did that?

Jessica Lynn Silva [10:50] No, no. I'm like, when I think of it now, I'm like, who humanly possible can do that much stuff?

Heather Monahan [10:51] No.

Jessica Lynn Silva [10:58] Yes. So, it was good. Another fun fact that the Lord did for me is I actually have 4 degrees, and every single one of my degrees was paid for. So, I have… even law school was debt-free. I'm one of the rare humans. And I don't say that to brag, I just say that. that when the Lord puts a purpose and a plan in your life. He literally creates steps and makes miracles happen in a way you would never even expected, and so that was truly awesome, and I will never forget the time I was in law school, and I go, Lord. You've given me 3 degrees debt free and it would be so cool if you would cover my law school too and I'm like I know that's a big ask that's like ridiculous people graduate with a quarter million in debt but I'm just asking literally a week later my prosecutor comes in I worked for a judge at the time he comes in he goes hey Jess how do you like your law school paid for I go excuse me he goes yeah you work for the judge so you get the tuition waiver assistance through the state and I'm like how do I do this he goes you talk to HR then your judge. signs off, and you just put your classes, and then we waive six credit hours every semester. And just like that, the Lord covered law school. So, it was, it was really incredible. It keeps me, I have a prayer journal, so I put my wins. and my request in there, and it helps, because the Lord's not a genie. He is a miracle worker, and he's amazing, but he doesn't say yes to everything. And so there's other times I'll joke with him, and I'll be like, okay, Lord, I know you heard me, because you answered that one in five minutes, but this one's been, like, 10 years, and I've got nothing, so… It's… but in the hard seasons, that's when I'll go back and remember the wins, and they help get me through, so… because there's been a lot of hard seasons, too.

Heather Monahan [12:45] Wow. Did you — looking back as a single mother as well and knowing how hard and how much pressure that is, there is a level of self-judgment, self-doubt, lack of confidence when you go.

Jessica Lynn Silva [12:57] Mm-hmm. Very much.

Heather Monahan [12:59] For sure, right? That's, and it's very normal. When you were, you're elevating, you were a paralegal, then you're becoming an attorney. Were you doubting yourself stepping into these different roles?

Jessica Lynn Silva [13:11] Every day. Every minute of the day. Even now, when I speak, speaking on stage and speaking is outside my comfort zone. I am a natural introvert, which shocks people, but that is just naturally where I am. But… I feel a calling, and I told the Lord, any doors you open and paths you want me to take, I'll go willingly. And I literally was just telling my husband earlier today, because I've had a couple more opportunities that are amazing open up, and I was like, I'm in awe of how the Lord works. But I also recognize He gave me these big things, He knows I'm terrified, but He gave me you, and He gave me a best friend who's a big prayer warrior for me, and He goes, you too, He knows where my anchors, that even when I'm starting to doubt myself, I feel it, they build me up. They'll send me long voice notes, they send me texts. They remind me of the value I'm adding to others and that it's not about me. This is literally about just using my story and testimony and embarrassing moments and wins and using all of that to remind everybody else in the audience of what's possible. And all you have to do is keep going. So, that's… when I put it like that. then it takes some of the pressure off. I'm like, okay, it's not about me anyway. Some are gonna love me, some will be bored out of their mind, and some will be like, you've changed my life, and I so appreciate you. So, I try to talk as if I'm talking back to my 18-year-old self, who would have desperately loved. the tools that we have today. The podcast, the learning, the access to great people that have gone and are willing to share their stories. So, I want to be one of those people that shares my story.

Heather Monahan [14:48] It's so inspiring and I'm so grateful that you're doing it and you're helping people right now. Okay, so tell me, how did you go from this come up and your marriage with your husband being deployed? Talk us through a little bit about that window because I think that people hear that you're married now, you're happily married, you have a great husband.

Jessica Lynn Silva [15:04] Okay.

Heather Monahan [15:08] Everything looks so easy on the outside. But again, this was not easy.

Jessica Lynn Silva [15:12] Oh, no. Even every day is not easy. We're two totally different personalities. I'm a lawyer. He's a graphic artist. And artists are sensitive. And I'm a Libra, so I'm sensitive. So it's like we had to learn each other's triggers and not step on each other's air hoses. So that took years. And then you just have to care enough because some people you can know and you just don't care to even try. So there's a lot involved. But the funny story is I went from being a single mom. I met and married my husband, and I worked for a law firm, so they handled the adoption for free. So that's my husband is all my son is known as his dad. He knows the story. But he is his legal father. And then we had 2 more children, so we have… we currently have 3 children and 4 grandchildren. And when we had the 3 children, I was like, okay, great, I have a partner, I have a life partner, we can do this. But I married a military man, and a military officer. So, he was never home. Especially for 11 straight years, I would live in one state, he wouldn't even be in the country. So I'm like, oh, this feels like deja vu, except now I'm a single parent of 3 kids, and managing properties, and trying to move us across the nation by myself. This is jolly. So that brought on a whole nother experience. Um, I tell people sometimes when you're married to someone military or, like. NFL players, you know, anything where they're highly traveling and they can't really be fully present all the time, because they have multiple, you kind of go through these cycles of. shock first, like, oh my god, you're not gonna be with me every minute of the day? I thought we were in our honeymoon phase forever. And then you go through, okay, I'm a little pissed at you that you did this. And then you go through, like, this grief, like, okay, you broke my heart, I don't know where's my teammate, my. And then for us, you came to this realization of, are we in or are we out? So are we gonna make this work? And when we did go through a hard time and it really stretched us, a friend of mine spoke into me and she's like, you have reasons to leave. And you have reasons to stay. So you need to figure out which one you want to do, and be all in. You can't be half in and half out, because all you're doing is, you're losing your fun personality. You're losing that thing, and you know, men love admiration, women love to feel safe. So as I started not feeling safe, I lost my admiration, which he then reacted to. So it was kind of a cycle. So that's where we just had to learn to, one, are we in this together? And if we're going to be in this together, let's make a game plan. And what are your triggers? What really matters? Things like that. So that's what had to work for us.

Heather Monahan [17:56] And then once you had that discussion, things changed.

Jessica Lynn Silva [17:59] Yeah, because we start caring. Like, it's not perfect by any means, and we always have to raise some, but it was one of those… like… like a life with the Lord. I went through my season of… I'm not sure what I believe on advances, this, and then I'm like, okay, Lord, you might not tell me the whole playbook, but I know I'd much rather have a life with you in it than you not in it. And I think it's the same with marriage. It's like, do you see yourself? Do you want Him in your life or out of your life? And once you know that part, then it's making it… I always told people, I didn't want a mediocre life, I wanted an amazing life. And the Lord always says, even in the Bible, I bring you abundance, I bring you joy, and I feel like if you're in His will, you'll feel peace about it, even if you don't understand all the steps. So, those type things. But communication is huge. I really feel like if you stop communicating, it starts dying.

Heather Monahan [18:50] And that's with anything. That's with business partnerships, clients, that's with friendships, that's with everything, your children. So, okay, so now you're a successful attorney. You have worked on your marriage. You are, you've got three kids now.

Jessica Lynn Silva [18:53] Mm-hmm. Yes.

Heather Monahan [19:06] You have multiple practices. Why in the world did you decide to become Miss Hawaii? Like, where does that even come from?

Jessica Lynn Silva [19:14] My husband was born and raised in Hawaii, so, um, I have a really good friend, he's a mutual friend of ours, Sandy Glant, and she's the one that brought me in the beauty pageant world. And to tailor it back a little bit. Six years ago, I was in a car accident, my daughter and I. A guy hit us, threw us an I-4, and it was awful. You don't understand why people struggle with drugs, alcohol, depression, until you're in chronic pain 24/7. Where you're like, what just happened in my life? I was, go to sleep, sleep eight hours, wake up like a little chatterbox at 5 a.m. all the things after that hadn't slept a night in six years, a full night toss and turn, had fractured ribs, whiplash, different stuff. Um, and so it was a constant sense of pain. I personally didn't fall for those things, but I can now… I can now more understand how people go to struggle, because they reached a point where I was like, give me anything, just make the pain stop. Like, I don't even recognize myself anymore. I gained 40 pounds, my daughter gained 40 pounds. At the time of the accident, she was doing competitive, um, she did football, and she did rowing, and she did competitive dance. She, all of that halted. She hasn't worked out that competitively anymore in 6 years now. It's just because you can't. She tried. She tried to continue with rowing and ended up in the ER twice. So, those type things change you. Um, and… When that happened a couple years ago, I said, Lord, I feel like I've lost my compass. I don't even recognize myself. I feel like just everything is struggling, and then… oh, and 3 weeks after the car accident, my dad died. And we… I had 3 office locations for my law firm, and we had sold the house that the whole family loved, which we all regret that we did that. We own multiple properties, and we sold one that was everyone's favorite. Shouldn't have done it, but we did. Um, and so all of that happened in the span of around the same time. So it was just a lot to process and go through and find your footing again. And so when I had prayed, I was like, Lord, I need a miracle. I'm really feeling lost, like I've lost my trajectory of what my next path and purpose is, and entered a really, really close friend of mine named Crystal, and she entered my life, and she's really strong prayer-oriented faith, and she goes, the Lord only puts me in people's lives when they have a big plan for their life. She goes, I just want to let you know. You have an anointing on you, and you're welcome, and I'm sorry. And so she is one that she was like, you're my blonde Barbie, and I don't know what's happening to you, because she didn't know me before then. She goes, but we're about to teach you hair, makeup, get you in shape, and lose some weight, and I'm going to teach you how to speak, and teach you, like, and all that. Like, she came out of nowhere. She was just literally an answer to prayer. And she came, and then that's what naturally just started going, and then Sandy is like, Jess, you need to be in beauty pageants. I think you should apply for this. And so it was just, the Lord just put people in my life right after I prayed about, I need, I've lost my compass, I don't know my next direction. And then all of a sudden, the new doors opened. And so it was just a new path. Um, and that's kind of what led to the beauty pageant world. It also was forcing myself outside my comfort zone. Because I didn't know the Lord was gonna want me to start being a speaker and start taking stages, because that was nowhere on my radar. And it was a way, I'm like, okay, well, if it terrifies me. I'm gonna do it anyway. I'm gonna face it head on. Um, because I have a friend that told me once, and I love this analogy, she's like, we always get so terrified of the monster in the closet, and then when we confront it, we realize the monster was just a little gummy bear. And I'm like, oh, that makes so much sense. And it takes away all the scariness of it. And so that was kind of where, if I was shying away from it, I decided I was going to force myself to do it. And that's kind of what started this whole path of doing stuff outside my comfort zone. And it just naturally opened amazing doors that I didn't expect. But the Hawaii part comes because my husband was born and raised in Hawaii, and so when he retired from the military, he created his own Hawaiian clothing line that we both do, and so our business has a presence in Florida and Hawaii, so that's kind of how it was full circle.

Heather Monahan [23:38] Wow. I mean, it's incredible how many times you've reinvented yourself and stepped into uncertainty and unknown. The more you do it, does it get easier?

Jessica Lynn Silva [23:43] Mm-hmm. Yes and no. Yes, it gets easier, but then the Lord makes you level up, and when you level up, it's a whole new thing. Like, it gets easier because you're comfortable, and then he's like, okay, that's great, next level, and you're like, wait, this is a whole new level with a whole new set of rules. And so then you come back in in confidence. And I know I've told you, because we're friends outside, you were an amazing grace for me. Like, when we were stationed in Minot, North Dakota, you and Shailene Johnson were the ones who I, like, ate up your podcast. I listened to you guys on repeat. You helped save my marriage, literally. And you helped me so much with confidence, like, because I struggled with that. I struggled with that because I grew up poor, and I had frizzy, curly hair, and crooked teeth, and huge glasses. So I was made fun of by the cheerleaders, and I was poor, so I was the one that showed up at the slumber parties. with… they had the New Kids on the Block or the Backstreet Boys sleeping bags. I literally had a pillow and a blanket. They would show up with all the name-brand snacks. I'd show up with the Great Value Walmart brand. So it's like… the confidence was always low on my meter, and I didn't know how to instill it, so you were a powerful piece of my life story, even when you didn't even know I existed at that time.

Heather Monahan [25:07] Well, I'm so grateful for you saying that. That makes me so happy. Gosh. And right back at you, and you know this, I grew up poor and had those same issues that you did. And that's why I felt called to share it.

Jessica Lynn Silva [25:09] Mm-hmm. Yes!

Heather Monahan [25:22] when you start unlocking things, and for everyone listening right now, you know, in your life, when you start realizing, oh, I figured this out, share it with people and help other people, pay it forward, because you never know what door you can open for someone, you know, what… and gosh, you're such a huge connector, and it's one of the things that I've.

Jessica Lynn Silva [25:29] Correct. Mm-hmm.

Heather Monahan [25:40] really admired about you getting a chance to work with you is watching how much you show up for other people. I don't even know how you do it. I don't know how you run businesses and show up for everybody, but I also see that when you show up, that opens doors for you. Can you talk a little bit about. that strategy in your life and how it's paid off for you.

Jessica Lynn Silva [26:01] It's been amazing. It wasn't a strategy in the way that there was a plan to it because it just naturally, it too comes back to childhood where I was the girl left out and it always broke my heart. So I never wanted anyone to feel left out. So when I enter a room, I. I naturally look for making sure everyone feels included. Now, I recognize, especially as you get older, the mature, you have… especially your high profiles, you have to protect them. They just can't be overloaded with a thousand people all wanting their time and attention, because you have to preserve it. But there still is just being approachable to the extent you can, and. trying to touch everybody's life, that when they get to interact with you, you left them with something. You made them feel better, you said a kind word, you offered them a Starbucks card, like, something to… I personally look at it as a way of being a testimony for the Lord. I'm like, okay, Lord, I want to remind everyone that you love them. I don't personally feel called to save people. Like that's not my calling. I have a lot of friends. It is. My calling is to remind you when you're tired, when you're burned out, when you're ready to leave your marriage, when your kids are about to drive you crazy, you've been broken by a friend. I step in and remind you he loves you. What can I do tangible? Do you need a sleepover? Do you need Starbucks? Do you need me to connect you with someone? Do you need a business? Do you need me to watch your kids? That to me is the true act of Christ and act of love. Um, and for some who may not believe they could just be a good person. for me, it just has a deeper meaning for me and a purpose. But that is just kind of where my nurture… and then it was funny, because then I started getting the name of Jess is a great connector. Like, if you know Jess, she'll connect you. It just… it came naturally, that from there. and the Lord knows my heart, it just… and that's where the Woman of the Year Award came from, which I absolutely love, from Sandy and Kelly, because they're like, Jess, you're like a unicorn. Like, you literally just pour so much life into other people, and you do it so authentically and without expecting anything in return. Um, and that's… that has opened doors. But that even goes back to my law firm. My law firm, I've had my own firm for 7 years, and before that, I worked for a lottery winner attorney. So a lot of our clients won the lottery. And before that judge, and I've been in law about, let's see, my oldest is 29, and I went in when he was 2. So, 27 years that we have been in that world. And… I will tell people that it's just… I lost my train of thought for a second, because when I just realized my son's 29, I went into 2, I'm like, wow, where does the time go? It's nuts! Yeah, but that's kind of where I'm just…

Heather Monahan [28:39] It is crazy. It's crazy.

Jessica Lynn Silva [28:44] I don't know, I want to add value to people's lives, and I did so, I've always done so, and when I did open my law firm. people wanted to see me win. They were like, I remember Jess as being the one that would get me hearing time with the judge when the other JAs would tell me it'd be 6 months, Jess would be like, let me get you in tomorrow, let me rearrange Judge's schedule, let me see what I can do for you. And I just naturally always did that, and then the rewards came later. When everyone knew Jess, and it's like Jess opened her own business, we want to make sure she succeeds, and it was wonderful. I've been in the black since day one, I've never took a loan, and my business runs word-of-mouth referral. So, I handle the whole state of Florida, and I have physical offices in Tampa and Satellite Beach. And then we'll look to do one in Fort Lauderdale or Miami soon, and it's. that's… it's just been a natural, like, where you sow seeds, and then you reap the harvest, but because you did it with a pure heart, and that's kind of where… and I tell people, even if I grow, and as I keep doing, I don't want to… and that's what my friend, the same one that… Crystal. she'll go, Jess, I've never met someone who is so fierce, and wins in court, and can kick ass, but at the same time, you're so pure and naive, and like, she goes, you have an innocence to you, and a shark to you, and it's like you're this. person. And so, it's just… I don't know. It's whatever the Lord wants to do with me.

Heather Monahan [30:12] So tell me a little bit about your journey with your personal brand and how uncomfortable it is for you to grow your personal brand, which would seem shocking on the outside to other people when they see your website or see you on stage.

Jessica Lynn Silva [30:20] Oh my gosh.

Heather Monahan [30:27] People just assume it's very, very easy. Talk to me a little bit about why you did it, how you did it, and if it's paying dividends for you.

Jessica Lynn Silva [30:35] I have done it because I strongly believe you can have a messy beginning and still have a marvelous middle and a marvelous ending, but you've got to begin. So, you can't steer a non-moving vehicle. So, if you're sitting in park. there's nothing you can do, and you're gonna be sitting there in one year, two year, whatever, later. You've gone nowhere. But if you get moving, then you can realize, okay, I'm on the right road, awesome. I'm on the wrong road, let me turn. You can pivot, you can steer, you can do something, but at least you're taking action. So I've always been just one of those that tries to take. Action and move forward towards the goal. But yes, it, my business ran word of mouth referral and I, so I didn't do social, didn't know that thing. I'm not good at that. And then that's where, and Sandy too, when she entered my life, she was like, girl, you have an amazing story and a great brand and you need, more people need to know who you are, so you need to get yourself out there. And she goes, you need to create a podcast. And it took… I was like, um, sure, I'll do that. And then 2 years passed, and I, like, finally did it. And my first guest was the Queen of the Congo, which is amazing. Yeah, and I love that. And then my second guest was Bill Walsh. So it's just and I would love to have you as a guest.

Heather Monahan [31:54] I'd love to be on it.

Jessica Lynn Silva [31:55] Thank you. But that is just where I'm like, I just laugh. I'm like, okay, Lord, you keep me in awe and you keep me humbled every single day. I've walked into rooms before. I mean, I remember even when I was with Judge, I'd won an award for something. And I never think about it, and everybody stood to attention, and I looked up, I was talking to Judge, and I looked up, and it was to honor me, but I didn't really pay attention to it, because that's just not me. And every… there was, like, 20 people with cameras all in front of us, and I'm like, who the heck are they here for? And they were like, they're here for you, Jess, that. why? I'm just Jess. Like, I didn't think about it. Like, I just do what I do in dance, and it's just, um… so that's kind of where… I had to learn the art. of sharing about yourself and building your credibility, because you're telling strangers, they don't know you. So you need to share some of your accolades so they know who you are. But that was hard for me, because. I'm not used to, like, not bragging, but not even trying to… like, I'm a big believer in that Bible, where it's like, you don't boast about yourself, you let other people talk about you, and so I had to learn that balance. I had to learn how to have a voice on social media, like. And I deal with estate planning and probate, so I deal with death every single day, which is why I adore pictures. I will be that girl that's like, let's get a picture, let's get a picture, because I want to capture that moment, because none of us are promised tomorrow. And I just love to do them. And all these pictures I gather, probably 2% make it online, but I'm getting better. So I just genuinely want to capture the moment, especially with people that I care about. And so I had to learn that whole thing of when you post, where to post, how to have a voice, how to build your brand, what is a brand, and then how, when you have different arenas, because I also model in an extra on TV shows, I'm a voiceover artist. And that came about because law can be so stressful, and if I'm in it, I'm in it to win it, so that I would be… I'd pour so much of myself into a case, I needed a release. And because I don't drink, I don't smoke, I don't do things, I'm like, my release is to go sit on. go be an extra on a TV show, be on set 12 hours, and just, like, let it go, be around a bunch of creatives for the whole day. And there's no pressure, because I'm not the principal, so I'm gonna get paid a little money, and then… so that became my outlet of just a fun side thing. Um, and all of that just kind of opened, but then it became of, well, when you're in several things, how do you mesh those voices together? Like if, because you're, I'm more than just a lawyer. I'm also a Florida Supreme Court mediator, and then I'm also Mrs. Hawaii International, and then I'm also Brevard's best estate planning attorney for three years in a row. I either first place or runner up, and then. Tampa Bay is professional, like, how do you keep doing it? So that, I've really leaned heavily on people like you, and Sandy, and Kelly Roach, and all those people I admire and have watched, who thankfully, amazingly, have become friends. Those have been ones that have been, like, my guiding light, my mentors, the people that help, and now I'm wanting to turn around and be that for others behind me, too. So, all that to say, I just knew I kept taking one step in front of the other. I would pray for the Lord to put the people in my life, the pieces where they needed to be, and then I took action. And that's what I always encourage everybody to do, is just… I'm a big believer, and I love vision boards and writing it down. So, if it mattered… and you taught me the movie where we make a movie of how we want, so it even leveled up from a normal vision board. That's become life-changing. Things like that, because…

Heather Monahan [35:41] The mind movie is everything. It's incredible.

Jessica Lynn Silva [35:43] Yes, it really is. It's like that Henry Ford saying where it's like, if you believe you can, you can. And if you think you can't, you're right there too. So it's like it's your mindset really is going to determine your trajectory. You're your own roadblock. So if you can get your own mindset and your own goals and everything in gear, the world's your oyster. So I want to encourage more people to do that because imagine what an amazing country would be if we were all just had it together, kind, loving go getters. just really had our things in order, it would be marvelous. It would be wonderful. So I want to do my part to help impact others.

Heather Monahan [36:22] It's so important that everybody does that, and we were talking earlier, it's about helping that younger version of you, and you know that that woman's out there, and that woman's listening right now, and I'm so grateful you're sharing this testimony. So, tell me a little bit about… you still get nervous speaking on stages, and how.

Jessica Lynn Silva [36:30] Yes. Oh gosh, you have no idea. Even in law school, it'd be funny. In law school, when you have to speak, you pretty much have to present a case and then open yourself up to have about a hundred people just tear you apart, the professor and all your classmates. Yeah, they're pretty ruthless in law school.

Heather Monahan [36:41] work on that.

Jessica Lynn Silva [36:57] And so, I would literally be in the bathroom before it was my time to present, and I would be, like, hyperventilating. I'd do 10 push-ups, I would be, like, praying, sweating in the armpits, sticking paper towels in there, and then I'd be like, okay, Lord, this is the best I got, and I would be just smile and pray, and that's it. And then I would speak, I can't tell you a word I said, because I would be so in nerves, and then I would end, and everyone would be like, oh my god, you were amazing, you did so good, and I'm like, what are you guys talking about? So that started happening. And then even now when I speak on stages, people are like, you are amazing. And I'm like, I remember it's funny when you and I both spoke a million dollar message. I don't remember a word because I was so nervous and I got off and everybody was complimenting and everyone was saying kind things. And one lady goes, you did so good, it started thundering and lightning, and you just talked so confidently through it all. And I'm like, I don't even remember the thunder. I remember nothing. So it is, um, but that's kind of where I just don't stop. Does it become easier? Yes, a little bit, especially if I'm in my more comfortable zone. I love fireside chats. I love panels. I love podcasts 'cause they're conversations. And we're just implementing and trying to leave nuggets of wisdom for the audience, so those are my favorite. Keynotes are still a little overwhelming, um, and so I'm taking strategies, tips on confidence from you, um, and things like that, and that still helps, so I'm looking forward to it, but I don't plan to stop. If the Lord opens doors, I'm gonna keep walking through them.

Heather Monahan [38:35] I love that you're doing that. You're choosing to see fear as a green light that means go and go faster.

Jessica Lynn Silva [38:40] Exactly.

Heather Monahan [38:41] It's exactly how I live my life. So, and I love that idea, too, that you were talking about. Yes, you become, you level up, you become comfortable in that level, and then you need to force yourself to level up again. The real miss is when you don't, when you just stop at one of these levels. And I see that happen for so many people. How do you challenge yourself to go to that next level when you don't really need to? You could stay where you were.

Jessica Lynn Silva [38:52] Mm-hmm. Mm-hmm. Um, are you familiar? Myron Golden is someone, he actually has his headquarters in Tampa and he's kind enough to do his YouTube video live. And when he's, he's like 40,000 an hour for coaching a million a year, but he will do it as his way of giving back to people. If you're invited, he will do it in front of a live audience and answer any of their questions for a certain period of time, which is amazing, and it's life-changing for people. And he has been one that… He's just kind of taught… opportunities. I'm trying to think how best to formulate, but he has two things that I like to resonate with. One is he's known for being trash man and cash man. And so, and he's worth quite a bit, like 60 million or something. And so people have told him all the time, Myron, and he's very based on biblical principles and he's very strong believer that. the Lord wants us all to be wealthy and abundant, so it is our own blockage that we're not there. And he will say that people are like, but you already have so much, don't you think that's kind of selfish? Don't you think you should stop? And so he does this little exercise where he goes, I'm gonna hold my breath and you ask me why? And he'll go. And you'll go, Myron, why are you holding your breath? Because there's not enough air in the world for anybody. I gotta hold my breath. And he's like, that's the same with money. It circulates, it's there, it's in abundance. And that's where I feel like with kindness and money, with fares. So other businesses and things like that don't. scare or intimidate me, because I'm like, we can be collaborative, there's enough for everyone. Now, evil and backstabbing, that's a whole other thing, that… no. But just actually all wanting to try to find our place in the world, and move and level up, I think we should be encouraging each other, and helping each other step up and do things. And I don't think… will ever reach a point where it's like, okay, enough's enough. I feel like the minute you stop learning, and stop reading, and stop challenging yourself, you start dying. And so, the comfort zone is a danger zone, and then you're gonna lose your impact, and. who knows how many people and lives you could have touched and saved if you just kept doing it. So, that's… for me, that's where I go back to saying, I never had a solid plan of action, like, I will be this by this, or I will do this. It was literally, like. Lord used me, and I know this is what I want out of life, have no idea how I'm getting there, but please show me the way, and then He did, and then just taking it to prayer and wisdom, and then dealing with the roadblocks as they came. Because… and as… I don't… I don't know… I feel like, um, even Robert Kiyosaki, I… because I love podcasts, they're just the best, which… even podcast was its miracle, because… I needed a coach, and I remember praying, saying, Lord, I need a mentor and a coach, and I know no one, and I don't have the money for it. It was back in the time when I didn't, and then he literally… I introduced to the world a podcast, and it was the best thing ever. So I encourage everyone, soak up the podcast, find your favorites, keep learning from them, and then who they… see who they follow, and go listen to them, too. that has been life-changing for me, that just listening to people pour into each other all day long. Um, it's priceless, and it's really helpful, so that's kind of where… those… I don't plan to ever stop until… I plan to do this until the Lord takes me home.

Heather Monahan [42:32] Oh, my gosh. What a beautiful testimony. And thank you so much for sharing it. Jess, tell people where they can find you, how they can work with you, and how they can keep up with you.

Jessica Lynn Silva [42:43] Yeah, I like to tell people I'm a lawyer who likes to bring law to real life. So I really like to make it approachable and understandable for you. I deal with estate planning and probate, but it's not about death. It's about living and leaving a legacy. So I want to help you build your wealth, protect your assets, and leave a legacy. that's pretty much… you can find me at jessicalynlaw.com, or on Instagram at jess.lynn.silva.

Heather Monahan [43:11] Well, Jess, thank you for taking your time today to share your wisdom, your word, with our listeners. We appreciate you, and I can't wait to see you again, because… Gosh knows, the next event, you've got one tomorrow, you've got an event tomorrow, but I'm sure you'll be back in Miami, um, very soon, and.

Jessica Lynn Silva [43:25] I do. Oh, I just came back from today from Miami to Vieira, and I'll be back I think I have to go back in a week or two. Yes. It's a blur, but it is there. It's on my calendar.

Heather Monahan [43:38] All right. Well, then I'll see you in a week or two when you get back. And thank you for being here.

Jessica Lynn Silva [43:40] Yes. My pleasure. Thank you so much for having me.

Heather Monahan [43:44] It's my pleasure. And guys, follow Jess. I will put all of her links in the show notes below. And until next week, keep creating your confidence. You know I will be.

This transcript was generated automatically and may contain errors.

Heather Monahan