270 | Transitioning Out of the Law with Jessica Medina

What do you do when you realize your practice isn’t working for you, and you want to do something else or leave the law altogether?

You turn to an expert like Jessica Medina, who can help you figure out the financial plan to make a transition possible.

Jessica is a lawyer turned Accredited Financial Counselor whose specialty is helping lawyers in this exact scenario.

In this episode, listen in as Jessica and I talk about her personal transitions from Biglaw to government and eventually out of the law altogether and how she helps her clients prepare for their own transitions.

• • Jessica’s experience working in different sectors of the legal profession
  • her poor money management habits early on
  • the wake-up call that made her change her financial habits when she realized her big salary wouldn’t always be there
  • the FIRE movement and how that changed how she thought about her money
  • Jessica’s number one piece of advice for new attorneys
  • balancing living your life and reaching your goals
  • the incremental freedom that comes along with achieving your goals
  • Jessica’s framework to create your financial plan for an upcoming transition
    

Jessica’s LinkedIn profile

Jessica’s website

Jessica’s exit plan resource

You’re listening to Personal Finance for Lawyers. I’m Rho Thomas, and as a busy wife, mom, and former Biglaw associate, I know all too well the tension between the culture of the legal profession and pretty much everything else you want to do in life. That’s why each week, I’m bringing you the information and tools you need to improve your money mindset and manage your money to create true wealth. Because ultimately, it’s not about the money. It’s about the freedom and flexibility the money affords.

Hey friend. Welcome back.

Today, I have a conversation with my friend Jessica Medina, who helps lawyers map out the financial plans for their transitions. We talk all about her story and the things that she works with her clients on, so if you’re a lawyer in transition, this episode is for you. I am going to read Jessica’s bio, and then we’ll get right into the interview.

Jessica Medina is a lawyer turned Accredited Financial Counselor on a mission to help attorneys create the financial freedom they need to do big things. She graduated from Columbia Law School in 2004 as a single mom of twins with over $200,000 in student loans and went straight to work at a large law firm in Washington, D.C. After eight years in private practice, she switched roles and became Senior Counsel at the Division of Enforcement at the United States Securities and Exchange Commission. She left the government to work in an area of the financial industry outside of the securities world and now teaches other lawyers how to use their money to finance their dream lives.

With that please enjoy this conversation with Jessica Medina.

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[Rho] Welcome to the podcast, Jessica. I’m so glad to finally have you on.

[Jessica] Thanks for having me, Rho – many years in the making.

[Rho] I know, I know. So, for anyone who is listening and is not familiar with you and the work you do, can you just give a brief overview, tell a little about yourself, and what you do?

[Jessica] Sure. My name is Jessica Medina. I am a lawyer turned Accredited Financial Counselor, and I really sit as a financial strategist for attorneys in transition.

My favorite clients are lawyers who may be a bit disillusioned with the way that they’ve ended up practicing law, or the way their career has gone and are looking for something that’s more fulfilling, but they’re a little concerned about what that might mean for the paycheck.

So I help people figure out how to transition with confidence to map out all the money moves that they might want to make before they transition, during and after, so that they can really pursue a career that is fulfilling to them and pursue a life of their dreams.

[Rho] Love all of that, and I know that before being a financial counselor, or accredited financial counselor, excuse me, you were a practicing lawyer, both in Big Law and in the government. So, can you tell us a little bit about your experience working in the law and what that transition to financial counseling was like.

[Jessica] Sure. I was one of those kids in high school who knew that they wanted to go to law school and basically fashioned my entire college education around it.

So I took all the courses to get the best grades possible, so I get into the best school and I ended up going to the best and most expensive school I got into. I went to Columbia in New York City, so also had the highest cost of living possible in the country, and I graduated with over $200,000 of student loan debt! Yay me.

In addition, I had some super surprises along the way. I ended up having twins my second year at Columbia, and I graduated as a single mom of twins.

So I was outnumbered by my own children upon graduation, and I’m so old we didn’t have federal student loans to cover the entire cost of your graduate school. And so a lot of my student loans were private, and even though, you know, as early as high school, I had planned on going into the government. I wanted to do public service work. That’s why I went to law school. That was not an actual path that I could take given my financial situation.

So like many folks who go to Colombia, I went to a Big Law firm. I was practicing in Washington, DC, and I stayed there much longer than I anticipated, primarily because of the money. And the recession had hit in the middle and I was just…I was running my own family, and I was the sole breadwinner. And I just did not see a path where doing anything other than practicing at a large law firm would make sense.

I also was terrible with money for most of my life, and so of course I didn’t see the path. I didn’t know how to run any of the numbers. I also didn’t want to look at any of my numbers, so I spent many years just kind of surviving on the fact that I made good money even though I lived in an expensive city and had a family. And I could make big mistakes with my money.

And when I really realized that I didn’t want to make partner at my firm, even though I was kind of on the partner track, the government finally opened up and there were positions at the Securities and Exchange Commission. I had been doing that kind of work in my own private practice, and I took a 50% pay cut to go over there, and that was my first lesson in money management, and it was a hard one.

[Rho] Yeah, that pay cut will definitely teach you how to, how to start managing it a little better, doesn’t it?

[Jessica] You know when, as I think back over so many, you know, kind of transitions that I’ve had in my life, decisions that I’ve made, things that I’ve just kind of done – I have a very push through grit your teeth, personality, and perspective on things which generally works pretty well in the law right up until it doesn’t.

And so, you know, having to do all of these things and bend over backwards, I’m sure my children would tell this story very differently.

I was super excited for all of these money experiments. They were not.

You know, I don’t think they enjoyed “no heat November” as much as I did, but you know, going over to the SEC, I was definitely more steeped in, you know, just the financial industry and wanting to get better about how I manage my own money.

It’s when I found the FIRE movement, which I know you and I share as a passion, and it’s when I realized I didn’t actually want to practice law at all.

I learned that being in the best position as an attorney, exactly where I want to be, doing work that I should enjoy, doing with a mission that I cared about was insufficient to actually bring me happiness and fulfillment.

And that’s when I realized it’s probably the law. It’s not where I’m practicing. I have to get out entirely. So then I proceeded to have my existential crisis. Uh, if I’m not a lawyer, who am I? What am I? What do I do, and how do I afford everything that I want to do in my life and for my children?

And that’s when I really buckled down and started figuring out the personal finance journey. And along the way I discovered the path to becoming an accredited financial counselor. And now I specialize in helping lawyers who also may not have some of those foundational money management skills. They want to be better at it. And they want to use it to, you know, make a transition to put more good out in the world.

So you know, it was a path that I followed with a lot of mistakes along the way and you know, now helping my clients do that a little more smoother with a little more savvy is a really fun job for me and more fulfilling than anything else I’ve ever done.

[Rho] Yes. And as you were telling your story, I was like, I know that so many people can probably relate to this because especially the part you were talking about being in big law and being terrible with money, but the fact that you had more money coming in just kind of covered that fact, right?

It’s like, oh, I’ve got all of this money coming in and it’s just going right back out and that was exactly where we found ourselves, where it was like, oh, we’re making all this money. Why do we have $150.00 left at the end of the month? You know, so…

[Jessica] Yeah, you have a big margin of error, right? You can make some really bad spending decisions, right? You don’t necessarily have to plan so much for the future cause you always have a nice big fat paycheck coming right every two weeks, you know, or every other week, whatever it might be.

And that doesn’t build great habits, right?

And so, you know, I think for a lot of attorneys, especially if you have never had to manage money, right, if you weren’t, you know, kind of paying your way through school and kind of having to manage your money from the time that you were younger, you might go from living on student loans to having…making more money than anyone else in your family. Making more money than anyone else in your community.

You may not have a lot of role models of how to manage money at that level, and it feels like a lot of extra and it is as long as you never leave the path, as you always make more money for the rest of your life.

And that’s a, that’s a pretty big burden to put on yourself for you know, the entirety of your working years.

[Rho] And you mentioned taking a large pay cut to go to the SEC. Was there any financial preparation to make that transition or like talk to us a little about that?

[Jessica] So probably when I was a mid-level right around my 4th year at my law firm, that’s when I had the breaking point of realizing, ohh I do not enjoy this.

You know? It’s kind of everything is shiny and new, right, when you start out as a junior attorney. If you enjoyed learning right, if you enjoy intellectual rigor, and if you’re intellectually curious – practicing law is an amazing profession. You get paid to think all day long.

And as somebody who basically worked in retail, hello Express right, all through college and in high school. I used to get paid to stand up and do right, basically manual labor, and now I was being paid to sit at a desk and think about, you know, problems and analyze things all day long. That was amazing to me.

And then about 18 months in, I realized, no, I’m reviewing a lot of documents. This is a lot of work. There’s a lot going on, but still interesting. I was still, you know, on active cases. I was working with really great partners.

And then when I was a mid-level. I was had been working on a very complicated expert motion to try to exclude some evidence in a very large pharmaceutical trial I was working on, and we won, and I didn’t even care. I was like, ohh, this was not worth it.

I spent so many weekends. My kids were at the firm building fort boxes in the room next to me as I’m filing summary judgment exhibits and attaching stickers. This was not worth all of the blood and sweat and tears that went into it. And that’s when I realized that this was not a long-term trajectory for me. I needed to figure something else out.

And then the recession hit. I was just happy to have a job, but I think, you know, that was really the first time that I realized the money is not always gonna be there. And if it’s not always going to be there, I’m going to need to make different decisions about how I am using this money.

And so you know, one of the things that I remember before I left my firm with my last firm bonus, I bought my minivan outright in cash. I was so proud of myself. I’d had a car payment for years before that. And, you know, I think that was kind of that was that was the shining example of really good, savvy financial decision that then allowed me to be able to take a pay cut without having to worry about a car payment moving forward. Right?

And so it was just thinking through, how can I remove things from my financial obligation sheet to make the next phase a little bit easier? I ended up buying my townhome before I left the firm. You know, there’s all kinds of things that you qualify for when you’re working at a large law firm that you might not once you take the pay cut.

So it’s really important to make sure that you’re, you know, taking advantage of all of those benefits before you leave, but starting to make some of those long-term financial decisions and put those things in place.

That really made the transition a bit easier because I didn’t have large ticket items that I was carrying over with me when I had to, now, you know, figure out how to live on 50% of what I used to bring in.

[Rho] Yeah, I love the way that you put that about taking things off of your financial obligation sheet. That’s something that I talk to my clients about a lot as well, where you know, if we are at the point where you’re living paycheck to paycheck or you’ve got that really slim margin between your income and your expenses, we got to figure out how to get some of this stuff off. Right? Get some of those expenses knocked out.

A lot of times it’s going to be things like getting that car payment gone, right? If we can pay off this car payment, if we can pay off this credit card or whatever it might be, just those monthly payments that stack up, right?

The payment itself might seem really manageable, but when you’ve got 15 of them, then it makes it a little bit tougher, right? So I love the way that you phrased that.

Want to go back to what you talked about at Express. I know that this is not the topic that people thought that I was going to go back to, but for those of you listening, Jessica and I have a lot in common, including that we both worked at Express in college.

It did not feel like manual labor to me. I was like, I’m getting paid to put outfits together for people. This is amazing. And then…

[Jessica] Well, that wasn’t my job. Dang! I ain’t get that job. I want that job. I was running all over the store.

[Rho] I was too, but I was putting these outfits together.

Anyway…but I just thought it was funny, like, thinking about the the different ways that we thought about that job.

But then when you talked about going from that to, you know, this really complex thinking, I remember when I first started working at the firm like, yes, it was shiny and new and exciting, but I was exhausted. I was like thinking at that level for the entire day, it expends a lot more energy than I’m just putting these cute outfits together, you know what I’m saying?

Like, I felt more mentally exhausted, I guess, even though working retail you might feel physically exhausted because you are on your feet all day, but it was just a different type of tired, and I thought it was interesting.

[Jessica] It may be that, right, my time at the firm felt like an escape because at home I had two screaming children, right? That required a completely different level of mental, physical, and emotional energy, and so being in a quiet, pristine, lovely office for, you know, more than 8 hours of the day was a little bit of a respite, and I’m just thinking.

And yes, I do remember coming home from Express many a night, I probably picked the wrong shoes, being very uncomfortable, had spent my day. You know, exhilarating, because I like people, and yes, the, you know, the fashion aspect was nice. But you know, I don’t, I don’t know that we share this, but certainly, you know, Express was also part of my money story in that I graduated from college with $4000 of Express credit card debt. That was one of my first debt repayment lessons.

And before I went to law school, I was terrified because I didn’t know how I was gonna manage it. I wasn’t gonna be able to work during law school. I didn’t think that would make sense for me to be successful. And my parents ended up bailing me out.

And it felt… I was relieved that they had done it, but I was also so ashamed that they had had to and I promised myself I would never find myself in that position ever again.

And then I made weird, emotionally charged, you know, decisions around money that it’s interesting seeing some of what I teach my clients in terms of making sure they’re paying attention to the emotional aspect of money, not just the mathematical aspect of money.

I see a lot of it in some of my own behaviors and how I would take, you know, something that happened in my life and completely blow it out of proportion and then make these crazy, very strict rules for how I interacted with money moving forward.

But it was because I didn’t have a lot of good role models. I didn’t have another way to experience money in my life, so every time I had, you know, something happen, it had a large impact on how I would move forward.

But yeah, Express, I don’t know, it could just be some sort of scheme to get college kids to take on credit card debt. Unclear. Unclear.

[Rho] Well, and I didn’t have the exact same experience as you with leaving with credit card debt, but my Express card was my very first credit card.

And almost my entire check would go back to Express with that 50% discount or whatever it was. So you know we would see the new stuff coming in first, and so we pick out our stuff and put it off to the side. And so I had very little of that Express money.

[Jessica] You see the margin between what you were bringing in and what was going back to Express was quite small.

[Rho] Exactly.

So yeah, but so another thing that you brought up that I want to go back to is the FIRE movement. So for anyone who’s not familiar with that concept, can you talk about what it is and what it was that drew you to it?

[Jessica] Oh yes. So FIRE stands for financial independence, retire early.

Now the FIRE movement includes many philosophies and strategies beyond stopping work earlier than normal in life.

That being said, uh, that was what drew me to it.

When I was toiling away, you know, as an attorney, I’ve been trying to… I always try to remember when did I first get bit by the FIRE bug. And I do think that it was actually after I had gone over to the SEC. I think that’s when I really started getting exposed to, um, kind of some of the people who were in this space for anybody who was early in the movement, Mr. Money Mustache was very popular at that time.

And, you know, I think part of it was because I actually had time on my hands. When I had gone over to the government, my work/life balance was completely different and I found myself bored at times on weekends, which I had never experienced before in my entire practicing life. And I had to fill that with something. And so I started consuming things outside of work, and my children, and I was dissatisfied with my life generally and my career.

I wasn’t sure why I was so unhappy. And you know, kind of like I said earlier, being in what I considered to be the perfect attorney job, doing exactly what I had always wanted to do, and feeling underwhelmed. That was really…that was disconcerting to me.

And so I felt very lost in terms of what I was supposed to do with my life, and what was my purpose, and where should I be putting my energy, and where should I be putting my brain power.

And so finding the FIRE movement and realizing I could get my freedom back. That’s actually what I missed.

And I talk about this a lot with my clients and with, you know, kind of my audience. I felt very trapped in, across so many dimensions for a lot of my working years.

I felt trapped by the career that I had chosen that I didn’t seem to enjoy. I felt trapped by my lack of skills in terms of being able to create freedom in my own life. I felt trapped that, you know, I was living in a house that was in a good school district instead of in a cool neighborhood where I wanted to live. You know, just kind of all of these dimensions.

And really the core of the FIRE movement is freedom. That’s what it’s about. It’s not really about anything else. It’s about giving yourself the choice and the options to do whatever you want to do with the time and the energy you have left on this earth.

And that was so tantalizing to me. It literally lit a fire under my butt, and got me really interested in fixing my personal finances so that I could have more freedom in my career moving forward, and in my life. And the results have been excellent. So I suggested for everyone.

[Rho] Yeah, the freedom was what attracted me to the FIRE movement as well.

And it sounds like you were a little bit more hardcore than I was at first, because I definitely wasn’t doing “no heat November” or, you know, you talked about Mr. Money Mustache like some of his views were a little bit extreme for me.

I saw people doing very extreme things, but I could see how this slightly different way of managing your money, right?

Instead of spending it all, like maybe you keep some of it. It’s like, oh, that’s a novel idea. Maybe I’ll do that. So that was something that was interesting to me that just that shift in how you manage your money can mean having more freedom over your time.

So I loved that.

But I also know you, and I know that you are not a “no heat November” kind of gal. So tell me about that switch from you know, being really extreme, no heat in November. I don’t know if there were other kind of extreme things that you were doing versus you know where you are now. Like, how did you go from there to here?

[Jessica] Oh, is that what we’re gonna talk about? Gonna talk about all the crazy things that Jessica did on her journey to freedom?

[Rho] Well, we don’t have to talk about all the crazy things. I’m just wondering what was the switch that flipped that made you not so hardcore?

[Jessica] So I think I think part of it, I think part of it, honestly, comes with age and just being able to see that the world is not black and white.

Uh, like I mentioned earlier, I have a grit your teeth and push through type of personality. I did for much of my life. And you know, I’ve gone through a lot of coaching. I’ve gone through a lot of therapy. Right.

I think there were some circumstantial things that ended up, you know, kind of creating that type of a defense mechanism in my own mentality. This is the way that I’m going to survive. This is the way that I’m going to get through things. And it took me shedding that survivor mentality to see that there might be another way, there might be a middle ground way to approach things.

And so what’s interesting is that I never require of my clients anything that I did on my journey. My journey was crazy. Like nobody should…I didn’t buy new things for a year as a challenge to myself.

Also because I had so much stuff already, like I was obsessed with camping gear. I really loved camping. And I buy like new camping gear all the time. I didn’t need anymore. We didn’t even go camping that much. It was like an idea in my head. I wanted to be a camper, so I had all this stuff, but I didn’t have time because I worked as an attorney. So it was just a weird fantasy world that I was living in.

But I think, you know, for me, part of it actually was probably getting myself out of the very strict and demanding world of Big Law, where everything does feel very black and white. Right.

You are..You have to be 100% in, you have to give 110% of yourself to everything, you know, in order to feel successful because that’s what is demanded. It really it is demanding for a reason, but it is demanding.

And and when I made the switch over to the SEC, there was just, there was breathing room for the first time in my entire life and I had never gotten to experience something that didn’t feel extreme. And so it was really kind of the first time that I was hanging out with people who weren’t… Oh, no, no, we just grit our teeth and get through everything.

And, you know, they had boundaries. They had lives outside of work. They had goals that were not just about, you know, achievement. I was fascinated by these individuals because I hadn’t…I didn’t feel like I had been around any earlier in my life.

And so I think that I don’t, I don’t want to use the term softened, but I definitely think that it allowed me to be a more nuanced individual and to approach problems with a much more nuanced perspective, which, ironic, that’s exactly how I deal with all of my clients problems as an attorney.

It’s all… it depends – literally our favorite answer.

And yet I had very black and white thinking when it came to my own personal goals and how I treated myself as a human and what I needed to do to be considered, you know, like a good human on this planet.

And so I think part of it was just, you know, having different types of people around me, and being able to see examples of a life that was not 110 percent, 110 percent of the time.

And I always tell people, you know, when they ask me what’s your number one piece of advice for new attorneys? Like go find some non-attorney friends. OK. Please.

[Rho] Yes.

[Jessica] Do not just hang out with people at your law firm. You’re all drinking the Kool-Aid together. You all have this like fishbowl mentality of this is all that there is in the entire world. There’s no ocean anywhere. You have very few examples of a variety of different versions of success.

And so I think for me, just getting out into a different community and seeing people living lives in a totally different way helped me see, wow! Maybe you can balance a couple of things and everything doesn’t have to be all, you know, all crazy hard all the time.

And so I think I was able to now apply some of that to, right, the financial journey. I also… this is what I will say, the financial independence movement is great if you are a 24 year-old software engineer and are perfectly fine living in a one-bedroom apartment in Silicon Valley with your 20 software engineer friends and eating rice and beans for the rest of your life, right? That is the quintessential hardcore FIRE model.

That doesn’t work if you’re working at a law firm that demands a lot from your brain and demands a lot, and you and you have a family that you have to take care of.

And so I think for me, I was trying to translate some of these really interesting and exciting philosophies from the FIRE movement into something that would practically work for someone that has a demanding profession, that works with demanding people, and demanding clients and, you know, still be able to, you know, have a life of some kind at the end of the day.

[Rho] Yeah, I think that’s exactly it, right. Like the mainstream FIRE that most people see, that most people talk about, it is very hardcore.

And for some people that works, right. Like I’m going to just live on the least amount I can and, you know, save all of this money. Invest all of this money to be able to retire in two years or whatever, but there is balance there.

And part of why I asked that question is I actually didn’t know that about you with that hardcore aspect early on.

And so I only know like the more sustainable, like financial independence Jessica.

And so I think a lot of people, when they first are getting started or thinking about wanting to improve their finances, their mentality is like that, you know, no heat November Jessica, where it’s like I just have to deprive myself of everything and eat ramen noodles and stare at the wall and not do anything. And then I’ll be able to pay off my debt and save all this money.

And I think your journey beautifully illustrates that it doesn’t have to be that way. That yes, you could start that way if you really wanted to, but it’s not necessary.

You can still have a life and have some balance and make progress on your goals, which is what my whole philosophy is, and that’s always been kind of my perspective on it. I knew I wasn’t doing that I’m going to eat nothing and you know, live in my van and whatever, so that I can say that I can retire more quickly.

I knew that I wanted it to be something that was more sustainable, both because my husband was not going for that and I had, you know, all of that. But I also just wanted to have a life. And so being able to make room for those things that we enjoy, but just change some of the things that we were doing with our money to redirect that money to those goals that get us closer to that freedom was everything for me.

[Jessica] See I didn’t have a you when I started on this journey and I didn’t have the now version of me who is much better at setting boundaries at taking care of herself at, you know, allowing the gray to exist in the world.

I was really hardcore in, in many respects, in an unhealthy way, right in an unsustainable way, and that’s what happened to me with my career. It’s what happened to me in terms of, you know, just kind of hard charging and just trying to survive being a single mom, you know, and a working mom.

And I think that, you and I have had this conversation, you had a very different experience at your law firm than I did because you’ve been very good at setting boundaries from the beginning, right. This is some sort of muscle that you were born with, Rho, that the rest of us have to train for years to develop.

And so I was always impressed with the people at my firm who were just like, “oh, no, my plate is full.” I’m like, are you allowed to say that? I didn’t know that was something you could do. Right.

And and that is that it’s a similar, it’s a similar dynamic when it comes to how do you approach a really big shift that you want to make in your life. And so I never recommend to my clients that they do it the way that I did because it was, it was painful.

And if someone had been there to tell me that I didn’t have to do it that way, I would have been so grateful. But, again, there weren’t role models of sustainable FIRE back when you and I were discovering the movement. You know, you created it for yourself because of your natural inclination. My old natural inclination was like, Ohh yeah, FIRE. Yeah, hardcore. Let’s go. Yeah, let’s do it.

And now as a more evolved human, and you know, as an Accredited Financial Counselor, I’m much more tuned into how damaging that can be and how unnecessary it is to get to your endpoint.

It doesn’t have to be that painful. We can figure out a way to honor your values, honor what’s most important to you, and still get you to your goals.

[Rho] Yes, I love that and something that I don’t think is talked about enough is that you don’t have to get to this full out, I can retire tomorrow to have more freedom in your life.

Like just taking those steps to start paying off that debt, to start saving more, to start investing. All of that as you start building up your accounts and you start paying down those financial obligations, as you put it earlier. All of that gives you more freedom, because now I’m less dependent on this specific amount of income that’s coming in.

And I think just having a little bit more freedom in some cases is just what people want, right?

Everyone doesn’t want to leave the law. I never thought I would leave the law. You know, I thought I was going to be a partner. Like, I was a first year, like, “hey, so how do I be a partner? Like, tell me all the things.” I got my little notepad and my pen, you know, but things change.

And so having the financial setup that we had, having started doing that work, when it got to the point where it’s like, you know what actually I think I want to try something else, I had the freedom to do that because we had done these things.

And so even if you don’t think that you want to leave the law, or if you know you don’t want to leave the law, but you know you just want a little bit more time for your family or time for yourself, having that control of your finances, like Jessica’s talking about, allows you that.

[Jessica] Oh my goodness. There’s so many early stages of FIRE benchmarks, right? Or just general financial wellness benchmarks that you can experience great levels of relief without getting to the “finish line.”

And I love that point that you know you will experience good results all along the way as you continuously improve your financial position.

You don’t have to get to the finish line, it doesn’t have to be, you know, all 110%, you know, until you’re 110% across the line, and remembering that makes it so much easier for folks to also experience that, you know, that moment of celebration and that moment of relief. Right.

When you get that card paid off and that payment doesn’t come out the following month, it really does feel very good.

[Rho] Yeah

[Jessica] You really do feel it, you know, kind of in your checking account. You know there are, there are some, for a lot of my clients they experience this every year when you know their Social Security stops being pulled out. Magically their paychecks are just a little bigger and would you believe it’s right around the holidays as they’re getting to spend a little money. Right.

[Rho] It’s nice.

[Jessica] And so when we plan for those kinds of things, right? We really can, you know, kind of supercharge how you are funding the things that are most important to you, but…

So you might be, you might already get a taste of it in your own life and what we want to do right in terms of you know helping people with their actual day-to-day finances is make more of those opportunities available to you so you can feel it faster, more often. And you know, on a trajectory that gets you. It’s all the way.

[Rho] Yes!

And so I do want to touch on your expertise, which is financial strategy for people who are transitioning. I am certain that there are people who are listening to this who want to change jobs, who want to leave the law altogether, who you know are on the verge of some sort of transition or something like that.

So what is a kind of basic framework, if you will, that they can start thinking about with preparing their finances for whatever upcoming transition they have?

[Jessica] Well, would you believe, Rho, I have a five-step framework to craft your exit plan? And…

[Rho] Do you? Tell us more.

[Jessica] There’s a cheat sheet. There’s an extensive e-mail series that goes along with it that will ask you all the questions that you want to ask yourself in order to start planning for this type of transition.

But this is, this is the meat of what I do with my private clients.

And you know, as you can imagine, right, the beginning steps of planning for any transition have nothing to do with numbers. You really want to imagine where would you like to end up? What would you like your life to look and feel like? You don’t need to know what specific job you want to have, but you do need to be able to imagine where are you living? Are you working full time in an office, or do you have a family? What kind of time are you spending with that family? You know, what are, what are your core values? Are you traveling frequently? Do you have a very nice home? Do you have a modest home?

Those kinds of questions are really important because that will help us backwards engineer to get you to that endpoint. We just don’t we don’t wanna plan to transition you into something that you are again unhappy with, right or you know, spend a lot of energy and effort and you know, financial resources on somewhere you don’t want to end up.

And then I’m not gonna belabor this point, but we spend a lot of time talking about your emotional relationship with money so that we can then do the real work to change your numbers and be able to implement any plans and strategies that we decide makes sense for you.

The third step is making sure that you are paying attention to your financial past, so that generally includes any debt that you’ve incurred that you’re still carrying, student loan debt, right, mortgages, or you know, a consumer debt. Anything that you know is an old decision that you’re still paying for.

We want to evaluate that and determine do we want to knock that out completely before your transition? Do we want to restructure it during your transition to make it a little bit easier on your cash flow or do we have to come up with a completely different plan for how we’re going to deal with it, right, as you’re getting ready for your transition and post transition?

And then we want to take a look at what’s happening with your current spending, right? That’s the fourth step.

You’re gonna have to look at your money. You’re gonna have to look at your money coming in and going out. And most importantly, we want to know what your lifestyle costs? We also want to know what your lifestyle will cost in the future, but we’re going to talk about that in a second.

But we also want to start managing the money going in and going out in a strategic way where you have a very good handle on what’s happening because when I teach my clients, I build personalized cash management systems for my clients, but when I teach them how to organize their money that skill will serve them no matter how much they make in the future, right?

Whether you get a pay raise, whether you take a pay cut, whether you go on a sabbatical, if you know how to manage the money coming in and the money going out, you will be able to adjust things as needed. But you have to build that muscle. You have to have that skill to do that confidently.

And so once we have a handle on that, then we’re looking at determining what does the future look like for you? Do you have big financial moves that you need to make? Are you trying to relocate? Are you trying to get into a new home? We need to make sure that we don’t take on any financial, new financial obligations that you won’t be able to manage under your new paradigm.

We also may want to do a rough projection of what is a safe income range for you, given all of your outstanding obligations and your lifestyle needs. And so I do some projecting of, right, kind of based on what you currently have going on in your life and what you know any restructuring that you might be doing of you know, the prior debt obligations.

What will it take for you to be able to continue your life and also reach your financial goals in a reasonable amount of time to just give you a sense of what the range is so that you know, if you take something below that, we’re going to have to make some big changes to what’s going on.

I’m not here to tell people how much they have to make or what they should spend their money on. I am here to help you make very intentional decisions in that realm so that you go in with eyes wide open and we have a plan of wherever you end up.

So you know, that’s kind of the five-step process making sure that we’re doing some of the softer visioning work first, addressing the emotional aspects, and then looking at the money in your past, in your present, and in your future to build a really solid plan so you can transition with confidence.

[Rho] It’s such a holistic approach. I love that.

And I see exactly how your clients feel so confident then to make these transitions, and if some of them have gone to positions where they’ve taken pay cuts or they’ve taken sabbaticals, and all of these types of things. And when you’ve got this robust plan for, ok, we know exactly how much life costs, now we know how much it’s going to cost in the future, these are the targets that we need to hit – excellent. Love it.

[Jessica] They really do enjoy it, right?

This is one of the things when you’re an attorney, I think you have a really keen understanding of what an attorney mind needs in order to feel comfortable. I have a lot of folks who, you know, when we get on the phone and we’re talking about potentially working together, they may have talked to another financial professional. And they were very underwhelmed by the answers that they got, right.

The people, they’re mostly, “oh, don’t worry about it. Oh, you’re a, you’re a lawyer. Oh, you make plenty of money.” That is underwhelming to someone who is trying to plan a transition that feels very important, very big, and has a lot of moving pieces.

I love looking at all the moving pieces. I love breaking it down for my clients. I love getting into the weeds with them and I think that’s why they feel so held and so served and feel so confident being able to take the next step because we have really done a lot of work to deeply understand, not only their financial position, but why they make the money decisions that they do.

And giving them tools and strategies and just the confidence that they can make better decisions moving forward and you know that’s, that’s what they end up doing.

[Rho] Yes. Well, this has been excellent, Jessica. Thank you so much for taking the time to come on to share your story, which I know is going to be so inspiring for people, but also your wisdom for people who are in transition.

Before we go, please take a minute and share where people can find you, maybe where they can find the exit strategy that you mentioned. All of those things. Give us your links.

[Jessica] Absolutely. You can certainly find me on LinkedIn, Jessica Medina LLC. I’m pretty prolific on there posting, and there’s lots of resources. You can certainly contact me through LinkedIn, but my website at jessicamedinallc.com.

I have a blog with a number of articles on exit strategies. I have an interview with Rho on FIRE strategies for lawyers.

And also a lot on student loan repayment because as you can imagine for my clients, student loans are a huge pain point, and it’s really not common sense, and it’s getting worse by the day. So you know helping people think through that is another area that I specialize in, but for the exit plan, I’m happy to drop the link in the show notes. It’s jessicamedinallc.com/exit.

[Rho] Perfect. Well, thank you again for your time. It has been a pleasure chatting with you as always, and I am just really glad to have you here and share you with my audience.

[Jessica] Thanks Rho!

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I hope you enjoyed that conversation with Jessica. Her story is so inspirational, and I have really enjoyed getting to know her and seeing firsthand the work that she’s doing and the impact that she’s making in our profession. Please be sure to go connect with her on LinkedIn, check out those links that she mentioned, and be sure to tell her that I sent you.

That is it for the episode today, please take a second share this episode with a friend or two. I know that it can help so many lawyers, and as always, I appreciate your support.

As we close out, friend, I pray that you take the information you learn here, apply it in your life and open up to the realization that wealth is available to you. As you do that consistently, week after week, you’ll continue to take steps to take back control of your time, build wealth, and live the life of freedom and choice you deserve. Talk to you later.