Navigating Career Changes, Law School, and Fatherhood with Jonathan Winn
Navigating Career Changes, Law School, and Fatherhood with Jonathan Winn
In this episode, first-year Baylor Law student Jonathan Winn joins Dean Jeremy Counseller to share the story of his path to law school. Jonathan reflects on his early years performing opera abroad, his work in journalism and marketing, and the experiences that eventually led him to pursue a legal education.
Now a father of three, Jonathan also speaks about balancing family life with the demands of law school and how his varied professional background shapes his approach to studying law.
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TRANSCRIPT
Jeremy
Welcome to another episode of Counseller's Corner. This is Jeremy, Counseller. I'm the Dean of Baylor Law School, and I'm very pleased to be joined today by first year law student Jonathan Winn. Jonathan, how are you doing?
Jonathan
I'm doing well. As best as can be expected with the finals starting next week.
Jeremy
Oh, yeah, well, you got that. You have a route to law school that includes another career.
And my understanding is that career was in journalism. So, tell me a little bit about what you did.
Jonathan
Yeah, I think you could, I think you could even safely say that I have three careers. I started off as a musician, and that's what I went to college for originally before I dropped out. And I actually spent a summer in Germany singing with a traveling opera company.
And so that was kind of my first career, and that's what I thought I was going to do ever since, like middle school. And then I decided that's not the way I want to go. So that's when…
Jeremy
Let me pause you right there.
Jonathan
Yeah.
Jeremy
Singing with a traveling opera company. What did that involve?
Jonathan
Lots of traveling around, really cool costumes.
And it was a summer gig, so they would set up a stage inside castles, mostly. And you would go to a performance. People would just kind of come out and see the performance. And then you would do the performance in this ancient castle, and then we would go home. We were staying in the somewhat dilapidated apartment buildings that were owned by a count, a German count who loved the arts.
And so, he had his castle, and then he owned a pair of apartment buildings. And that's where we stayed that summer. And we just kind of went around from there.
Jeremy
So which operas were you involved in?
Jonathan
So, the big one, the big, big one that we did was The Magic Flute from Mozart. And then we did La Traviata as well.
Jeremy
Okay, so you're singing in Italian?
Jonathan
And German. Yeah.
Jeremy
Okay. Yep. What about that made you say I'm going to go in a different direction?
Jonathan
So that's really interesting, because the way that whole thing came about was my older brother is also a musician, and he went to UNC in Colorado and did their opera program, and that's the, they have a summer program that sets that up and sends you over and connects you with the company that you're going to sing with.
So, he did that one year, and then he was like, hey, that was really fun. You should do that with me. So, on his last year when he was graduating, we went over and did that together and then he just stayed. He's been over there for 14 years now.
Jeremy
Wow.
Jonathan
And I came back and I was like, okay, is this what I really want to do?
And what really was rattling around in my brain is something very similar to what you said in Civ Pro. I had a professor who said, if you can see yourself doing anything other than music, you should go do that thing because you're not going to get rich. And the only reason you should be doing it is if this is what you love, and it is the only thing that you want to do.
So, for most of my childhood and early adult life, I assumed that I loved music and that was what I wanted to do forever. And then doing those performances and traveling around and living the lifestyle for that summer was a ton of fun. I loved it, but it really made me think, is this what I want to do forever?
And the answer was no.
Jeremy
So, you said you, you sing and you play music. What instrument do you play?
Jonathan
So, I did, I, I did voice and then I also play the double bass and piano.
Jeremy
Okay. Yeah. Is that something you still do to entertain yourself or for fun?
Jonathan
Yeah. So, my wife and I, actually, we met in high school, partially, partially through swimming and partially through double bass.
We had the same double bass professor. And so, for a while, we were playing in a community orchestra in Amarillo together. And that was like our weekly date night. My parents would watch the kids, and we would go play in the community orchestra. And then I also do performances with our church a lot of times to do solos and stuff.
Jeremy
Yeah, it's something you can do all your life. Okay, so you mentioned three careers. What's, you finish with the opera.
Jonathan
Yep.
Jeremy
Then what do you do?
Jonathan
So that's when I, really I, I always loved writing, but I assumed that was going to be my hobby and music was going to be my profession. So, I flipped them. I said, okay, I want to do writing as my profession and
I'll do music as my hobby. So that's where I started looking around for any kind of jobs that did writing and news producer came up, and that was like the main thing that producers do is they write. And it just so happens that, there was a bit of nepotism involved. Maybe, but my dad was the chief engineer at a news station in Amarillo, where I'm from.
So, there was a job open at the station for producer, and I called my dad as was like, hey, what do producers do? He's like, I don't know. But then he gave me the news director's phone and said, “Why don't you give Sean a call?” So, I did, and Sean was like, yeah, we're pretty desperate for bodies, so why don't you come over here and we'll see how it goes?
And then it turned out I had a knack for it. So, I worked in, at the station in Amarillo for a year and a half. And at that point, my now wife, who was my girlfriend at the time, had moved to Boston, and she was doing her doctorate of pharmacy up there, and she said, if you want to marry me, you better get up here.
So, I was able to make some really good connections and get connected with the news director in Boston.
Jeremy
So, I guess you did want to marry her.
Jonathan
I did want to marry her. Yes. Yep. So I made some good connections, and I interviewed for a position in Boston. And…
Jeremy
Are you now married?
Jonathan
We are now married.
Jeremy
Okay. That's good that you wanted to and you are.
Jonathan
Yes, yes. So, I was able to get a job in Boston as a, started as a part- time writer. And then three months later, I was a news producer.
Jeremy
So, so how do you go, and I'm assuming here that it's from the journalism part of your career to that you go to law school?
Jonathan
So, there was a break. So, I did journalism for five years in Boston, from 2015 to 2020. And my wife was done with her degree. We had just had our second son, and Covid happened, and everything shut down.
Jeremy
Yeah.
Jonathan
And at that time, I had actually returned online to school, and I was working on finishing my bachelor's at WT, West Texas in Canyon.
And if I continue doing online school, I was going to have about 3 or 4 years left, and my wife was looking at my degree and she said, you know, we can move back to Amarillo. Your parents would be there for grandparents’ support, which is great when you have two little kids, and you could be done with your degree in a year and a half.
And by the way, you could get a music minor on top of that. So, we packed up and left Boston and moved back to Amarillo. And that's where the journalism stopped. I did some consulting work for the station there and helped them do, launch a few shows and stuff like that. But I was really looking at, okay, what do I want to do next?
And the plan was to go to MBA school. And so, I took the GRE, applied to a bunch of schools, and then didn't get in anywhere that that I wanted to go in. So, we were like, okay, well, I'll just retake the GRE. You get a higher score and then we'll go next year instead. And so, it came time to start working on all of that, and my wife and I both had the distinct impression separately that she was supposed to go do her MBA before I was supposed to. Then we're like, you've already got your doctorate of pharmacy, why do you need an MBA? Because I don't have any kind of grad degree. I just graduated from, with my bachelors and I'm like 30 years old, so don't, shouldn't I go?
But we decided to let her go do her MBA, and she worked and did her MBA in two years. And then, I was, that's where I got into marketing. I was doing sales for the new station in Amarillo, so I was doing marketing for them. And then I left the sales job to work for Rice University for a little bit and did marketing for them as well.
Jeremy
At some point, are we going to go to law school? How does that, how does that connect?
Jonathan
So, law school, the idea for law school really started back when we lived in Boston. We had a bunch of friends who were lawyers, and they all talked about how much fun being a lawyer was because they got to fight and win. Except they use their brains instead of their fists and you get to win in court.
And they said it was really fun. So, I started thinking about law school all the way back there. And I even had a couple friends who were producers with me at the station who went and did law school after they left news to become lawyers. And then when I was doing marketing, I had to assume that I would go get my MBA and then do business stuff.
But it turned out that I didn't like the sales side of things as much, and I didn't like the business side as much. And that's where my wife really kind of pushed me into you should really look at law school. It might be fun for you because you get to deal with complex issues and do a lot of reading and a lot of writing.
And by the way, you get to, it's adversarial, you get to fight people.
Jeremy
So, have you, have you found law school so far to be sort of consistent with those expectations?
Jonathan
Yeah, I would say that law school has been more fun than I expected it to be even…
Jeremy
How so?
Jonathan
I just, this might be a hot take, I don't know, but I genuinely enjoy the reading, and I genuinely enjoy the lectures, and I cannot say that I have ever in my life truly enjoyed every single class that I've ever taken.
And maybe we'll get to like trust and estates and I'll change my mind. But so far, every, every class that I've taken, I've genuinely enjoyed the content. And it's just so fun to be learning about all these concepts and then seeing how they apply in my life. I mean, contracts are everywhere.
Jeremy
Okay. You mentioned you, well, I, you have two sons. Now three.
Jonathan
Now three.
Jeremy
All boys?
Jonathan
All boys.
Jeremy
Okay. What are their ages? And how are you balancing family in law school?
Jonathan
So, they are seven, five and three. So they are…
Jeremy
That's a lot.
Jonathan
Yeah. We're in, we're in the thick of it.
Jeremy
You are in the thick of it.
Jonathan
Playing zone defense.
Jonathan
Yes. So, it's definitely a challenge. And it's a challenge that we knew, going into law school was going to be hard. Like I said, my wife has a doctorate of pharmacy. So, she did professional school. We know how hard professional school is.
So, and to further complicate matters, my wife still works in Amarillo. She works; she's an IV pharmacist at a hospital there. So, she works seven on, seven off. So, she's in Amarillo for seven days, and then here in Waco for seven days. So, when she's here, I'm usually up at the law school much later, catching up on stuff.
And then when she's gone, I'm picking up the kids when after aftercare is over and taking them to school and making lunches and dinners, and we're going to tennis and dance, and all the other fun activities. So, it's definitely a challenge. And that's I have to be really organized and use my time wisely.
Jeremy
Yeah, which is good advice for anyone. But of course, for you, there's, I imagine, a very thin margin for error on that sort of stuff.
Jonathan
Yeah. You can, you can definitely tell like the first, the first quarter was really figuring out, okay, how am I going to fit the workload of law school and with being a dad? And on top of that, the added complication of my wife not living here still for half, half of the months.
And it was really figuring out that, figuring out that balance of what do I need to get done when the kids are sleeping, what do I need to get done when I'm at work and they're at aftercare? And it's, it's a challenge that's still in progress, I would say.
Jeremy
Yeah. And for people who don't know and aren't familiar with the geography of Texas, Amarillo is about 6.5 hours away from...
Jonathan
Yeah.
Jeremy
…from Waco. So, it's not commutable, you know.
Jonathan
Correct.
Jeremy
Yeah. I'm wondering how you have found or how you think, your background in music and your background in journalism might translate both to law school, but also to the practice of law.
Jonathan
So, I'm a very, I would say that my life has led me to believe that we are put in specific places at specific times to learn specific things, and I would say that I learned from each of my careers and each of those steps that I've taken in my life that have brought me here.
So, for music, I loved music because it was fun, but also because it brought hope and joy to people. And when I was in journalism, it was all about telling stories about the community. It was listening to people and then figuring out why those stories mattered and trying to translate that to other people who didn't know them, and just sharing the stories of my community.
And I found that really powerful and also really, really difficult at the same time. Because you see all of this bad stuff that's happening. And that's one of the downsides to local news, especially, you're reporting on the really bad stuff that's happening every single day. And as the producer, I'm not on one single story. I'm back at the news station, and I'm putting every single story into a rundown that I'm in charge of two hours of news for.
So, I got every single story every day, and that really weighed on me. And, you know, I think a lot of people get into journalism because they want to change the world and make a big difference. And that was, that was something that I felt like I was doing partially as a journalist, but I couldn't do everything that I wanted to do.
And that's where I thought, okay, maybe if I can do business and have more, I can have a bigger impact in business. So that's where I got into business and marketing, and when I was doing that, it was really at the granular level. I was helping people who had local small businesses do marketing, navigate marketing, which is a really complex.
And there's all kinds of crazy stuff out there, especially with AI. And so, it was helping people accomplish their goals. And all of these things really kind of lead to law school, where lawyers were out there telling stories, listening to people arguing, and taking complex issues and presenting them to a jury that has to figure out what's going on.
Jeremy
You, one of the things that I think is true of you is that your sons have sort of influenced, it seems, what you want to do with your legal career. How is that? And, and how have they been, continue to inform what you want to do with your, with your career.
Jonathan
So, it's no coincidence that, I tried several times after I left college originally, without a degree. I tried several times to go back to school and finish that degree unsuccessfully. And suddenly when I had, when we had our first son, I'm back at school and I'm getting the A's that I knew I should have, beginning from the very beginning. And it was that motivation of what kind of example do I want to set for my kids?
What do I want them to see when they look at my life? What, what, what can I show them that they can do? So, three boys now. Think, they all think it's really cool that we walk out the door in the morning and they've got their backpacks on, and I have my backpack on, and we're all going to school at the same time.
And, you know, we talk about homework. My five-year-old is learning to read and doing really well. But sometimes he wants, he's the middle child, so he's a little wild sometimes, doesn't want to do what he's supposed to do. And I'm like, well, I have to do my homework. You have to do my homework with me, too.
And my older, my oldest child stays up late and he gets to read before, before going to bed. So, he'll be on the couch, and I'll be on the couch and he'll be reading his fun, you know, second grade science fiction books. And I'm sitting there reading contracts or torts or whatever. And he always peeks over and he, he looks and he's like, I can read that.
I know what those words are. And I'm like, more power to you. Yeah, glad you've got it figured out. But, you know, I look at my kids and I'd say, okay, I want to be a good example for them, that even if their path doesn't take it, their life doesn't take a traditional path, they can still become more and become better and continue to grow and develop at any stage of their life.
Jeremy
Yeah. That's great. Okay, we have reached the lightning round. The questions are silly. Your answers have to be short. If you could teleport anywhere in the world instantly, where would you go?
Jonathan
Brookline, Massachusetts, for ramen.
Jeremy
Okay. Glad you glad you clarified. What's a movie you can quote start to finish?
Jonathan
Any of the Star Treks.
Jeremy
Okay. If you could only listen to one musical artist or band for the next month, who would it be?
Jonathan
Haven
H-A-V-E-N
Jeremy?
Okay. Which season fits your personality best?
Jonathan
Winter.
Jeremy
Best spontaneous decision you've ever made?
Jonathan
Answering, answering a message on Myspace for this girl who had messaged me twice. Who I had no idea who she was. Who then later became, became my wife.
Jeremy
Okay, you can only keep three apps on your phone. What are they?
Jonathan
Reddit. Weather. Kindle.
Jeremy
Childhood snack you still love?
Jonathan
Cheez-Its.
Jeremy
Simple activity that boosts your mood?
Jonathan
Reading for fun.
Jeremy
Okay. Excellent. You passed the lightning round. I understand you have a question for me.
Jonathan
Yeah. So, this is a question I ask to pretty much any lawyer that will talk to me. The main gist is, it's a moral, a moral and ethical dilemma of you, you have a client and, you know, they're couple, culpable.
They did the thing that they're accused of being doing, of doing by the plaintiff. And you also know that you can present a very strong defense and probably get the case tossed out and when and so the person who your client harmed essentially gets screwed over. And I like to win as much as the next person. But I struggle with this issue from like a moral standpoint.
Jeremy
Yeah.
Jonathan
So how do you think of that as a lawyer and how do you approach that?
Jeremy
Well, it's a, it's a, I think it's a very common kind of question that non-lawyers have of lawyers. And, and most commonly presented is how do you defend someone you know to be guilty. And so, it's usually pitched in the context of a, of a criminal case.
Of course, the same could be true on the civil side. But so, let's just take that, that I've been asked to represent a criminal defendant. Let's say it's of a very serious crime. And for whatever reason, I know that the, or I believe that the defendant is guilty of the crime. How can I represent this defendant?
And I think one of the first questions to ask is, as opposed to what? Right? I mean, a lawyer could say, “I don't want to represent this client.” But let's say that in a criminal context, it's an appointment. You know, you've been appointed. It's a place where there's no public defender's office. You've, the judges assigned you to defend the client.
“Why don't you want to defend him?” the judge says. Well, what are you going to say? Because he's guilty? Because you think he's guilty? I mean, guilt means the jury has convicted him of the crime. And suppose you do walk away from it because you think it's immoral to do that. Somebody has to defend him. Right? Unless we're just going to start convicting people based on no defense at all.
I think what's really important to remember is that one of the reasons we can have some confidence in the outcome of the civil and criminal justice system is because lawyers do zealously advocate for their clients. Is it perfect? No, of course it's not perfect, but it's a human endeavor, so it can't be. But I think that's a real, essential, part of it.
Having said all of that, you don't want to, I mean, the lawyer shouldn't be saying things that aren't true, right? You don't. What you do on behalf of that client is different, I think, than whether or not you represent someone that you, you know, know to be, to be guilty or not. But I do think it's a question that presents very clearly something which is that there are moral and ethical dilemmas and issues in the life of a lawyer.
And I think what's really important is that people be like you, which is you're pondering them, right? That that you stop and you, you think about them. I think I’ve; I've not been a criminal defense attorney. I think most all criminal defense attorneys probably have represented a client that they knew to be guilty. And, for some of them got them a result that was an acquittal or an outcome that just wasn't consistent with what their actual guilt was.
But I think it's, unless we're just going to allow lawyers say these are the people I'm not going to represent, and we're convicting people based on no evidence just because a lawyer thinks, I don't want to represent this guy, that that's a really, really bad outcome on the other side. And I also think it's true, that if the lawyer knows the person is guilty, they're probably, the lawyer's probably not the only one who's going to be able to figure that out.
Jurors are pretty good at sniffing that sort of thing out as well. And, and a lot of times that very situation is the thing that has the lawyer saying to that client, you need to accept this plea deal, because if you don't, the jury is going to convict you, and the punishment will be even worse. I think 99 times out of 100, that's the more likely outcome, is that the lawyer's giving advice to the client based on that knowledge, and that advice is not going to be, hey, you're going to get off scot-free.
The advice is going to be, you are likely to be convicted by a jury of this crime. So, but, I appreciate the question and thanks for coming on, Jonathan.
Jonathan
Yeah, of course.
Jeremy
Appreciate your input.
Jonathan
It’s been fun.
