Jessica Collins: The Simple Path To Wealth Workbook, F*ck It Money, Retiring At 32 & Living Life On Your Terms | FRLP 119

JL Collins wrote The Simple Path to Wealth for his daughter. Jessica Collins followed those lessons and retired at 32. But when she told her dad she wanted to leave her corporate career, his reaction wasn’t what she expected.

In this episode of the Fit Rich Life Podcast, I sit down with Jessica, author of The Simple Path to Wealth Workbook, to explore growing up with the godfather of financial independence, finding the courage to leave a successful career, and figuring out what ambition looks like when you no longer need to work for money.

Jessica shares what it was like being the “little girl who wouldn’t listen,” how her reluctance to talk about money inspired her dad’s writing, and why her mom’s everyday spending decisions were just as influential as those financial lessons. We talk about prioritizing experiences, resisting lifestyle inflation, and saving half of everything she earned long before she understood what that habit would make possible.

We follow her journey through AmeriCorps, the Peace Corps, and a successful tech sales career. As her income grew, her lifestyle stayed relatively steady, and her savings rate climbed. But bigger paychecks and recognition couldn’t make up for working 70–80 hours a week at a job she didn’t enjoy. Jessica explains why leaving still felt scary, how she approached it as a six-month break, and why she never went back.

Then we get into The Simple Path to Wealth Workbook and the questions behind the numbers: What do you want your money to make possible? Why does financial independence matter to you? And how can you enjoy the benefits before you reach your FI number? Jessica explains her distinction between FU money and F-It money, including when spending a little more can protect your time, energy, and peace of mind.

We also explore talking about money with a partner, supporting each other without needing identical spending habits, and enjoying the journey instead of putting your entire life on hold.

Finally, we talk about redefining ambition after leaving work. Jessica shares how pottery, pole dancing, scuba diving, fitness, and writing have become part of her “hobby era.” I also open up about my own identity shift after leaving tech sales and learning to pursue things simply because I love them. We close with Jessica’s advice for fitness, money, and life: keep it simple, stay consistent, and get more curious.

Episode 119 of the Fit Rich Life Podcast with Jessica Collins is available on Spotify, Apple, YouTube, and wherever you enjoy your podcast entertainment.

The Simple Path to Wealth Workbook — available November 24, 2026: Pre-order here

Website & Resources: thesimplepathtowealth.com

Get a FREE copy of my Fit Rich Life Money Guide: mwob.fitrichlife.com

In This Episode:

• Growing up as JL Collins’ daughter and the “little girl who wouldn’t listen”

• How Jessica inspired The Simple Path to Wealth

• The money lessons her mom taught through everyday decisions

• Saying yes to experiences and being intentional about spending

• Childhood allowance envelopes and learning to pay yourself first

• Saving 50% before fully understanding why

• The college conversation that revealed how differently her friends thought about money

• AmeriCorps, the Peace Corps, and finding her way into tech sales

• The seductive pull of bigger paychecks and external validation

• Increasing her savings rate while keeping lifestyle inflation in check

• Working 70–80 hours a week and questioning what it was all for

• Having enough money to leave before feeling ready to leave

• Why JL initially hesitated when Jessica wanted to quit

• Turning a six-month career break into early retirement

• Helping update The Simple Path to Wealth and writing the companion workbook

• Finding the personal “why” behind financial independence

• FU money vs. F-It money

• Buying back your time and knowing when frugality stops serving you

• Enjoying more freedom before reaching full financial independence

• Talking about money and FI with a romantic partner

• Supporting each other without needing identical spending habits

• Redefining ambition when it’s no longer attached to a career

• Pottery, pole dancing, scuba diving, and embracing the hobby era

• Choosing work because you enjoy it

• Keeping fitness and investing simple and consistent

• Asking better questions and becoming more curious about other people

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Full Transcript:

Jessica Collins: The Simple Path To Wealth Workbook, F*ck It Money, Retiring At 32 & Living Life On Your Terms | FRLP 119

Introduction: Jessica Collins and The Simple Path to Wealth Workbook

Justin: JL Collins originally wrote The Simple Path to Wealth to teach his daughter, Jessica, everything she needed to know about money. But Jessica didn't just inherit her father's philosophy. She became the first person to walk the entire path from childhood to financial independence. She reached FI at 32, walked away from a successful corporate career, and discovered that having enough money doesn't automatically tell you what to do with your freedom. Now she's helping a new generation turn her father's ideas into action with The Simple Path to Wealth Workbook, coming out at the end of 2026.

Today we explore what it was really like growing up as JL Collins' daughter, how Jessica made the simple path her own, and the question that begins when the money problem ends. What are your ambitions for when you no longer have to work for money? Welcome to the show, Jessica.

Jessica: Thanks, Justin. I'm excited to be here.

Becoming the Person JL Collins Was Writing For

Justin: So, your dad began writing the ideas that became The Simple Path to Wealth after you told him you knew money was important, but did not want to spend your life thinking about it. Fifteen years later you reached FI at 32, left corporate America, and wrote the workbook. When did you realize you had become the person he had been trying to reach?

Jessica: When did I realize that I had become the person he was trying to reach? I think I always knew that I was the person he was trying to reach, because I mean anybody who knows anything about Dad's journey knows that this has been 34 years of him just drilling this into my brain. So I think I always knew. I just didn't get it. Maybe I got it in my twenties, but I always knew he was trying to teach me something.

Justin: Yeah. And when do you feel like you actually took ownership of feeling like you actually became this person who took what he was trying to teach you and implement it? Was it when you hit FI and left the corporate job? Did it happen before you actually left corporate America? When did you actually feel like, wait a minute, I think I am financially independent and Dad's lessons did actually work for me?

Jessica: I think there's two parts to that question that I'm hearing. I think the first time I realized that his lessons had sunk in was when I started corporate America because now we're making big girl money. And so now we actually have real adult big girl money to play with and to put these lessons into practice. I think when I had that "oh shit" moment of, maybe he was onto something with the whole financial independence, retire early, FU money, I'd probably been at corporate America for three or four years and I was like, oh my God, I hate this. I hate this.

And I have to do this for the rest of my life. Wait, no, I don't have to do this for the rest of my life. That's kind of the whole thing that's been drilled into my brain. So I think there was a little bit of a progression there. It was now we get to actually put the teachings into practice. And then there was that moment of, wait, maybe I could actually be the person that pulls the trigger and walks away from this job.

Growing Up With Monthly Money Meetings and Vanguard Statements

Justin: So what did young Jessica find annoying or irrelevant about these money conversations your father forced you to have from, to my understanding, a very young age?

Jessica: Justin, I thought all of it was irrelevant. In my defense, I was an only child, and I wasn't going to school the day after having these monthly meetings with my parents, with the Vanguard statements in front of me, and telling my friends about this stuff, right? I was bored, I didn't care. But I was genuinely under the impression that everybody was learning this stuff. Right? You don't know what's going on in other people's houses, right? And for most people's childhood, you just kind of assume that whatever your childhood is might be the normal. So I just assumed everybody was learning about it. And I thought all of it was irrelevant.

I thought all of it was boring. I didn't understand why it was important. I was just like, this is a thing that Dad needs to do because this is what dads do. And my goal was, how do I get out of this conversation as quickly as possible?

The Little Girl Who Wouldn't Listen: The Origin of The Simple Path to Wealth

Justin: Your dad told me yesterday when I was talking to him that he refers to you as the little girl who would not listen.

Jessica: Correct. I wouldn't, and isn't he grateful for that? Because if I had listened, we wouldn't even be here right now.

Justin: So explain that. I know what you mean by that, but explain it so people who've never heard of JL Collins or The Simple Path to Wealth understand what you meant by that comment.

Jessica: Sure, sure. So it's in the most endearing way. My nickname is The Little Girl Who Wouldn't Listen because the backstory is my dad has been trying to teach me about financial literacy, specifically what everybody knows now as The Simple Path to Wealth. He's been trying to teach me these strategies since literally my first memory. We were probably three or four at the dining room table. And I wouldn't listen. I wasn't interested. I didn't want to participate. I was dragging my feet. I wasn't engaging. It was my least favorite thing to talk about.

And so, as you mentioned at the top of our conversation, Justin, he had a moment with me when I was coming home from college my freshman year. He starts again on one of his lectures. This is lecture like a thousand and one in my life. And I said, Dad, I know this is important. I just don't want to have to think about it all of the time. For him, he says that was an epiphany because he's one of the few that loves to think about all things finances.

And from that moment, he started to write letters to me with all the information, hoping that when I was ready to absorb it, it would be there for me to absorb. Then that became a blog, which then became a book, which then led to who he is now, as far as being known as JL Collins and The Simple Path to Wealth, which led to the workbook, which led to me being here.

Justin: So essentially you are the reason JL has become the godfather of financial independence.

Jessica: Yeah, and the next time you see him, make sure you remind him of that. He knows, but it's always good to remind him.

Justin: I definitely will. Yeah. And it's such a beautiful story because it's just a desperate father wanting to impart his money wisdom to his daughter so that she grows up with a life where money is not a source of stress and worry. And I love how it all unfolded because it obviously worked in the long run because you did retire early at 32, financially independent, which is pretty incredible.

What Jessica Learned About Money From Her Mom

Justin: But before we get to that, I do want to pause and just ask because JL gets a lot of the glory, but I know your mom, Jane, also contributed to your relationship with money. And that doesn't always appear in many conversations. And so in your own words, what are some of the things that you feel like you learned from your mom, whether that was a conversation or just observing her behavior as you grew up?

Jessica: The latter for sure. If my dad was the vocal one about having all of these conversations, my mom was the one who led by example. Not saying that my dad didn't, right? Both of my parents had very healthy, very good money habits. But my mom was the one that I was going shopping with. I was going to the stores with. So while my dad is talking to me about these things that kind of feel like fantasy, right? What's a dividend? What's an interest rate? Who the heck is Vanguard?

Mom is the one that I'm going to the stores with, and she's the one showing me, in real time, what life looks like to actually have a money exchange. You know, if we go to the store, what are we buying? What are we looking for? What are the prices we're looking at? Why are we buying certain things, right? We were never going to the store, my mom and I, and buying something frivolous or for the sake of having it or something that was really expensive when you could have got something just as good, same quality, for a better price.

So that's where the real life application was being demonstrated for me, even if at a young age I didn't realize that that's what was happening.

Justin: I love that. So essentially your mother was modeling not keeping up with the Joneses and making purchases based on what is a good deal and what is good quality, not what is the most expensive, impressive thing we can buy.

Jessica: Yes, and what do we need? Right? There were plenty of times where I can't think of a straight example, but let's say, for example, we needed a new couch. For example, okay, we're not gonna go find the cheapest couch that we can get. We wanna get a nice couch. We wanna get a couch that feels comfortable. We wanna get a couch that's gonna last us for years so we don't have to buy another one next year. That's what I was witnessing, is we're not buying something to keep up with the Joneses. We're buying the things that we need, and when we need them, we're being really intentional about them. So it's not that we're constantly looking for the bargain. We're just being really thoughtful and intentional with where our money is going.

The Sweet 16 Story: Saying No to Cars and Yes to Experiences

Justin: Can you share the story about your friend's birthday and the cars?

Jessica: The friend's birthday, the Sweet 16? Yeah. I think that's one of my mom's favorite stories. So I was 16, around that age, and a girl in my class was having a Sweet 16. That was a big thing, for at least my generation in my school, to have a Sweet 16. And so she had a Sweet 16. It was this huge party. Everybody was invited. It was a great time. And my mom picked us up. It was myself and another friend, and she was picking us up. And we were leaving the party kind of early.

And there were two cars in the parking lot, and both had big bows on them, and both of them were for the birthday girl. And one was a summer car. And I don't know anything about cars, so don't even ask me what the brand is or any of that. But one was a summer car because it was a convertible, and the other one was a winter car. And my peer, for the rest of the time that I knew her, drove those two cars for their respective seasons. And I spent a lot of time trying to bargain my parents to buy me a car. One car. I never won that battle.

Justin: So I think that's a really important part. And in preparation for this, I listened to another conversation you had. And you said that as a child growing up, your parents said no to a lot of things like a car, but they also said yes to a lot of things. And I'm just curious in your own words, what was it like growing up having parents who wouldn't get you a car when you're watching your friend get two cars? Not one, but two.

Jessica: Yeah. That's such an interesting question, Justin. Because now, as an adult looking back on it, I have to remind myself that my parents said no a lot because my parents always said yes to experiences for me. And in a lot of ways, now as an adult looking back on it, that's so much more valuable. So they were always looking to say yes for an experience. It was things that felt silly and frivolous that they would say no to. What was it like?

I'm sure it felt frustrating and I'm sure it felt unfair because I was an angsty teenager who had a very wonderful childhood with two supportive parents who loved her unconditionally. So of course I was looking for something to be angsty about. But the other thing too is my parents were very fair. There were a lot of times where we only had one car. So as long as my parents were able to do what they needed to do, get what they needed, go wherever they needed to go, they were very willing to let me have access to their car.

So, yes, there was a lot of no to things, there was a lot of yes to experiences, but there was a lot of compromise as well. It wasn't like I was sitting there constantly mooching off of people for rides and feeling like I couldn't have an experience or hang out with my friends because you didn't buy me a car. It's just interesting that I'm sure at the time I was like, This is so unfair and now looking back on it, I'm like, I wasn't deprived of anything. It was totally fine. They were very willing to let me use their car when I wanted it.

How Parents Shape Spending Habits: Experiences Over Handbags

Justin: In your own life, as you've gone through it, do you think that them saying no to you helped you formulate your own habits around what you personally say yes and no to when it comes to spending money?

Jessica: When I think about why I have the spending habits that I have, I don't think it's based off of what they said no to. I think it's based off of what they said yes to, and I think it's based off of what I witnessed. Because when I think about how I spend money now, when I think about my values, where I want to spend my time, a lot of that stemmed from what they were willing to say yes to. And a lot of that is experiences. I will drop money on an experience. You will never catch me dropping money on a handbag. For me, that's important. Those are my values.

That's what I grew up with. And I think that is a direct response to not them saying no to something, but them saying yes to something. Yes, and witnessing how they were spending their money. Again, to use the couch example, they were always willing to drop money on an experience as well.

And when we needed something, maybe a couch or something else, we're gonna find the one that we like that we can afford that's gonna bring us the most joy, and we're gonna spend money on it, and we can do that because we're also not spending money on an impulsive purchase decision because it feels like the thing that everybody else is doing.

Justin: I love that. It's such a beautiful example of how important it is for parents to do the thing, not tell you to do the thing. Because they literally just modeled the value of spending on experiences and not spending on things to impress other people. And by default, that's what you do in your own life.

Teaching Kids About Money: Show Them, Don't Tell Them

Jessica: It's funny that you say that because one of the most common things that people will ask me is, I want to teach my kid. So what could I do? What's the thing that JL told you? Or what's the thing that he did in your childhood that I can do with my kid to replicate that and instill this in my kid's brain? And 10 out of 10 times I go, just show them. Just show them. I mean, I think it's good to have those conversations and they're gonna be boring and it's gonna go in one ear and out the other, but at some point it's gonna get absorbed. But it is just better to lead by example.

The Four Envelopes and the Dollar Allowance

Justin: Share the envelopes and the dollar allowance story. Because I think this illustrates the frustration as a kid, but we're contrasting this against how your parents behaved and you just modeling their behavior.

Jessica: It's a good story. I think it also highlights the frustration from Dad's point of view. So when I was young, my allowance was like a dollar. And I think it was just like that because Dad was trying to show me some of these habits. And I had four envelopes. I had a charity envelope, I had an investing VTSAX envelope, I had a university/college envelope, and then I had a fun envelope, right? And I would get a dollar and it would all be in coins, right? 25 cents, 10 cents, whatever here and there.

And we would sit there and we would have to take the coins and put them in all of the envelopes. And it was a 25/25/25/25 split. Easy. And we did that for years. And what my dad was trying to show me, he was trying to instill the habit of: where does your money go? And paying yourself first, and thinking about we are always paying ourselves first, aka investing, thinking about college, because that was a conversation we had a lot, learning how to give back, and then also you have some for yourself. I get it now as an adult, makes total sense.

As a kid, and even up until I was like in my 20s, to me, three out of those four envelopes were just black holes. And so my frustration was, why are we even having this conversation? You say I have a dollar, but I'm walking away with 25 cents. And I'm sure from Dad's point of view, he's like, What do you mean? You have a dollar and you are choosing where to put it in all of these envelopes.

And I remember there was one time, I want to say I was in high school or something, he flipped the script on me and he goes, You choose where to put all of this money. And I was like, What do you mean? This feels like a trap. This feels like a trap. Because at the time these were all still black holes, but I was babysitting. I was waitressing, right? So I was making more money. And so I was like, is this really my choice? Because if it's my choice, like 100% of it's gonna go to me. What do you mean?

And all of it was just really frustrating for all parties involved because I just didn't get it. And he was probably sitting there being like, why the fuck doesn't she get this?

Starting Late vs. Starting Early on the Path to Financial Independence

Justin: So I can only imagine how frustrating it was for you as a child, but I do have to give a nod to JL because I didn't even discover the idea of investing and reaching financial independence until I was 34, your current age. Now fortunately, I'm a very obsessive person. So, and listeners to the show know, I went from $80,000 in debt to millionaire in two years. But you hit FI years before I did, because I didn't hit it until I was probably 38. And you basically hit it in your early thirties or before you're thirty, in part because of that teaching from him. Because I didn't have that.

My parents knew nothing about investing. And, you know, I grew up very poor, for lack of a better word. My parents went bankrupt as farmers, and money was always a struggle, and money was always super fucking stressful. And in my view, my parents divorced because of money. So my experience was very different than yours. And so it's just so funny to me that basically kids are going to find some reason to get frustrated with their parents. But if I had a choice, I'd be like, Fuck, I wish my parents did what JL did with you.

Because even if a little bit of it sank in, which I think it did with you, it allowed you, once you got to corporate, to be like, Fuck corporate, I don't wanna be here. You were already on your way to saving and investing and getting to FI. So you're so far ahead of me in your twenties than when I was in my twenties. So I do wanna give a hat tip to JL for doing that, despite you being frustrated and him probably being frustrated that it didn't seem like you were getting it.

Jessica: Yeah, 100%. And I think the other thing too is because I had such wonderful loving parents and we had a good relationship and I had a good childhood. Even when I didn't get it, I still had Dad's voice in the back of my head. So when it was my choice, I was still acting on these habits that he had instilled in me, even though I didn't get why. I didn't get why it was important, but I was still saving 50% of everything.

Anything that came my way, babysitting money, birthday money, when I was having jobs like waitressing, or I had jobs in college, 50% of that all went into investments and saving. And I remember being like, I don't know why I'm doing this, but like I have to because I've just always done this. So 100%. My parents get all of the credit, and thank goodness that they were relentless. It's like they kept doing it because I'm in a better place for it. It just took me a while to put all the pieces together.

The Student Loan Conversation That Changed Everything

Justin: So I want to talk about your senior year conversation with a friend about student loans. And this is college, I assume, senior year. What did she say and what did you suddenly see when you had that conversation with her? And set the scene for us. Let us know, you know, kind of how it went down and what you were talking about.

Jessica: Yeah. So second semester, senior year of college, this was a group of my close friends. We'd been friends for the full four years, and we're just having the conversations that you can imagine we're having. And so you're in your last semester of college, you're talking about life after college, what are we doing, jobs, where are we living, all that stuff, right? So part of those conversations are logistically what happens next. What are we doing? Where are we living? Are we moving in with our parents? What cities are we moving into?

I had a friend who, and this was probably a bit of a hyperbolic comment, if I'm gonna be honest, but it stuck with me enough to continue with the conversation with her. And it was our group of friends together. This wasn't a one-on-one conversation. She just off the cuff goes, and Justin, I'm gonna be honest, I don't actually remember the number that she said, but it was low. She said something like, I can't wait to pay like $50 or $100. It could have even been $150, I don't know. But I can't wait to pay this student loan bill for the next fifty years of my life.

Now at that point, I'd been friends with this girl since freshman year. So I knew what her plan was after school. And I also knew what her plans could have been. So she could have moved in with her parents to save money and commute into the city, because she had a job, she had a car, etc. So my brain is like, what are you talking about? Are we being serious with this comment right now? And so I said something. I was like, what do you mean?

And that's when it all kind of came together where she was like, Well, I won't be able to afford anything else because I have to get a new car. Well, your car's fine. I don't know why you have to get a new car. I have to get an apartment in the city. Again, I don't know why you have to. You could move in with your parents. I know that's an option because we've talked about this previously, and you could commute into the city. You could also take public transit into the city.

I am also, at that point in my life, fresh off of a conversation with a woman that I had met a couple months earlier who was a waitress and also had a part-time photography business, and she was a couple years older than me, maybe like 25, and she was working her ass off to pay her student loan debts down and aggressively paying. And she had shared numbers with me and everything. So I'm sitting there thinking, but there's ways for you to save money. The second level to this story is I also knew what her job was gonna be.

So she was about to enter into a career where she was gonna start making, I think it was like 45K. So not a lot of money, but we had never had that kind of money before. And she was also on a career path that would allow her to get bonuses and potential commission and raises and things like that. So I'm sitting here being like, why do we think that that's the reality we have to live with?

And through the conversation, it was just because we have to get the expensive apartment, we have to have the nice house, we have to do all of these things, and paying off the debt is just not our priority. And all of my friends agreed. And that was a fundamental moment for me because I was sitting there saying, but why? Why would you not prioritize paying off your debt when you know this is gonna be a ball and chain situation. We know that it's just gonna get worse, right?

I don't know why you would be okay keeping that for 50 years when you could actually just keep the car that you have and use whatever money would go to a new car payment to pay off this debt. And so that was a pivotal fundamental moment for me because I think that was the first time in my life I was having real money conversations. Remember at the beginning, you think everybody is having these conversations that I was having with my dad. And that was the first time I was like, no, we fundamentally think differently about this. And that is wild to me because I really thought we were all on the same page with this stuff.

Looking Rich vs. Getting Rich in Your Twenties

Justin: It's such a great story because the average American is your friend. They feel like they have to do these things. They have to get the nice apartment in the city. They have to get the new car. Because they just graduated college. They got a job. They gotta look like they're making it.

Jessica: And we have adult money now.

Justin: Yeah, we got big girl, big guy money.

Jessica: Yeah, yeah. We got big human money. We gotta spend it. Yeah.

Justin: Yeah. And I was the same. As soon as I started making money in my twenties, I wanted to look like I had made it. And I just dug myself into debt. And so I was, you know, in my twenties, the average American who gets caught up in looking rich instead of actually getting rich. And I think this is such a beautiful story because this is you actually recognizing, like, wait a minute. I am not the same.

Jessica: Yeah, exactly. It was a wild turning point for me.

Justin: I love it. Well, thank you for sharing that story. That was really important for me to cover that on the show.

From AmeriCorps and the Peace Corps to Tech Sales

Justin: I wanna briefly touch on post-college. You decided to go into AmeriCorps and Peace Corps. Kind of walk me through that decision and then get me to you joining a tech company.

Jessica: Sure. So I had dreams of joining an NGO or the UN. I studied international relations. I wanted to travel, so I said AmeriCorps, Peace Corps is gonna be really great boots on the ground work for me to achieve these dreams. I came back, applied for jobs, no one gave a single fuck. And it kind of crushed me a little bit. There's a part of me that sometimes reflects and says, you should have had a little bit more grit and you should have gone for it a little bit harder.

I kind of gave it a shot, and when I say gave it a shot, I came back from the Peace Corps and like chased that dream for maybe six months. And then I was kind of resentful. I was like, I had done all of this four years of boots on the ground work. It was really intense and I was doing the hard shit, thinking that somebody working at an NGO would care. And again, I wasn't thinking I was gonna do the UN immediately, but I thought I could start somewhere small. No one gave a fuck. And I said, okay, well, let's go do something else.

And I have my dad in the back of my head, in the back of my mind, saying, and his philosophy was, if I was gonna work, might as well make the most money doing it. So I was like, let's get into sales, let's see what happens. The worst thing that happens is this is the thing that I do until I find the dream job, whatever that looks like.

And one thing led to another, got into tech sales on a whim because anybody who's been in sales for a big software company, a big SaaS company, knows that it's an easy entry because they'll teach you the skills so you can get in, and then you kind of just gotta show that you can hang. And I was really good at it. And I got promoted and I got recruited and I kept doing it. And the paycheck kept getting bigger. And I didn't like it. But there's something really seductive about being good at something and getting rewarded for it. So it's not a sexy story, but that's the fast and dirty version. Yeah.

Why a Sales Career Is Seductive and a Cheat Code to FI

Justin: I think it's a sexy story. What man or woman doesn't want to make a fuck ton of money and get rewarded for performance? And that's the thing I talk about a lot on my show. I think a sales career is a cheat code to financial independence because if you can get commissions, it's based on how well you perform. And if you're a top performer, guess what? You make a lot of money. But you nailed it on the head. It is seductive and addicting to get paid this way because you're like, shit, I feel valuable. Every time I perform well, they pay me even more. And it's hard to stop. So tell me about that.

Jessica: Yeah. And fundamentally, I'm like, wait, you're paying me to talk to people? All right, let's go. It is so... seductive's the word of the day. It's so seductive to be good at something and to get validated from it. And when the validation is money, and I'm coming off of Peace Corps and AmeriCorps and being a college kid where I am broke as fuck. And then you have to remember who my dad is, right? Like if you're gonna work, get the most money as possible, do the thing.

You just keep going and then before you know it, and this is what happened to me, I am working 70, 80 hours a week because it's all about the contract. It's all about the deadline. It's all about the funnel, right? You probably know this from your career, but also anybody else in sales, it's a numbers game, right? So how do we fill that funnel so that we get that small group at the bottom? And all of it just becomes like a game and it's addicting until one day you wake up and this is what happened to me. You're like, have I sold my soul to the devil?

What am I doing this for? What is the end goal? Because the other thing about it is there's no promotions unless you want to become a manager. Absolutely not. There was no part of me that wanted to manage anybody because I liked that I got to control my paycheck, my hours, my workday. I liked being in control, which was great. But then there's no next step, right? The next step is just maybe a bigger book of business or bigger accounts, right? Which means more money, which is great until you have that moment of, whoa, I am working so much. I'm working so hard. I kind of don't like this.

It's seductive, but I don't actually like it. I don't feel worth or satisfaction from it. Am I committed to doing this for the rest of my life? Whoa. What are we doing?

Top Performer With No Desire to Manage: What Am I Doing This For?

Justin: I went through the same thing and I was fortunate in my 10-year career in tech sales in the SF Bay Area that I at least was proud of the mission of my company and what we were doing. But similar to you, I had zero desire to be a manager of other salespeople. I had zero desire to one day become chief revenue officer, even though they tried to get me on that track multiple times. And I was like, Yeah, fucking right. I don't want to manage people. I just want to control my schedule and make as much money as possible.

And the game of making money is a fun game, but eventually you realize, like, what the fuck am I doing? Like, am I just gonna play this game for the rest of my life? Like, isn't there more to life? Like, aren't there things that are more meaningful to me? So my question to you is, what were you doing with all that money you were making?

Saving 50% to 80% of Income and Avoiding Lifestyle Inflation

Jessica: Not spending it. We were saving, we were saving 50%. And the thing is, is because I had that habit instilled in my brain, and at that point I was getting it more. Like I was getting more of the lessons, right? But we were saving 50%. And the thing is, is as my paycheck continued to increase, my lifestyle stayed the same. So, and I was already a pretty frugal person, right? So as my paycheck goes from high five figures to low six to like slightly higher six, I'm still living on decently low five figures. And I was happy.

I didn't feel like I was depriving myself, but I share that just to say that we go from saving 50%. Now we're saving 60. Now we're saving 70. Now we're saving 80 because I didn't feel deprived in my life. There wasn't anything I wanted to spend money on. And also I didn't have time to spend any money because I was in this hamster wheel of just like, let's get the contracts in, let's keep going. Who else can I talk to? Right? Like my whole life is whatever this job is.

Build Financial Independence Before You Need It

Justin: So I love this conversation because I don't have any problem with people making as much money as possible. But please, for the love of God, make sure you're investing a healthy portion of it. Because when you get tired of the job or it starts to feel meaningless, you've already got the financial independence part solved. So you can stop doing the meaningless work once it starts feeling meaningless. Now, some people love to work. They're going to find a sales career. They're going to be in it for a lifetime. I have no problem with that.

But I think a lot of people in all types of careers, not just sales, for a while it's fun, it's interesting. You're kind of on that growth track where it feels like you're leveling up your skills, you're becoming better at what you do, and that's fun. But eventually it gets old and you realize there's more to life than work. At least there's more to life than working for somebody else.

Jessica: Yep, the novelty wears off.

Justin: And so please get the workbook, The Simple Path to Wealth Workbook. Because while you're enjoying making money, do the workbook exercises and build the financial freedom on the side while you're having fun making money. So then when you do have an awakening like Jess, where you realize, wait a minute, this isn't what I want to do for the rest of my life, you don't have to then start the financial independence journey.

Jessica: Yes. Yeah, I think figure out your why. You might love it now, but you don't have a crystal ball. You don't know how you're gonna feel. I remember when I first got my corporate job, I was so excited to go into an office. Because, like I said, I was a college kid, AmeriCorps, Peace Corps. I was like, yeah, let's go be a big girl. Let's go into the office. I was so excited. I loved having teammates. I loved that there was HR. I loved all of that stuff. And that novelty wore off so fucking fast. Actually, maybe it lasted for like a year and then it wore off.

And there was no more excitement. And it was the rat race. And thank God I had these skills that my parents instilled in me and I was saving. I didn't know what I was saving for. I didn't know what I was investing for. But that's okay. Do the thing, set yourself up for success, invest so that when you figure out your why, or when you figure out that you need a change, you have that cushion. You can do it. You have that freedom and that flexibility.

Better to do that proactively than get to your "oh shit" moment and be like, well, fuck, now I have to create the plan and I gotta be here for another five years or whatever it is, right? Depending on your job.

Justin: Yeah, for most people it's a ten to twelve year journey from start. Now there are extreme examples, high earners who are really good at keeping their expenses low can do it in, you know, if they get a 70, 80, 90% savings rate, they can do it in three to five years. But most people it's gonna be a ten to twelve year journey. So if you start that journey at your early twenties, then by your thirties, you're pretty much free.

Having Enough Money to Leave Before Having the Courage to Leave

Justin: So my next question is about the transition from loving everything to realizing you don't want to do this for the rest of your life. And you had enough money to leave before you had the courage to leave. What took so long? Because I believe it took you about nine months from when you decided you were ready to leave.

Jessica: Yes, ish. So the idea actually came into my brain when I was 30. I was like, and this tells you how little grit I probably had, because at that point I had only been in corporate America for like four years, and I was like, no, I'm done, I'm done. This is awful. So it was like 30, where I was like, wait a second, doesn't Dad like talk about this stuff? Doesn't he like teach this stuff? Isn't that what the Chautauquas are for and the book and all of the other conferences? Isn't that like what this is about?

Okay, maybe we should like pay a little bit more attention to people's stories and all of these conversations. So it was actually like two years prior that I'd started thinking of like, hey, I hate this. Maybe I don't have to do this for the rest of my life. Maybe at some point I can pull the trigger. And that's when I'm starting to really look at what is my spending? What is my lifestyle? Right? If I walked away right now, what would I have to change? What would I have to pull back on? Those are the type of questions that I was ruminating in my brain.

But I was doing this quietly to myself. I wasn't having this conversation with my dad. And then yeah, like nine months before I pulled the trigger, and September of this year, 2026 will be two years for me pulling the trigger. I just was like, I can't do this. I have to do this. But it was really just kind of fear. And this is gonna be ironic for everyone. When I had first floated this idea to my dad, he wasn't thrilled. He was like, no, you can't just walk away without having a job. Which took me by total surprise because I was like, What do you mean? Hold on.

We have spent my whole life, you drilling this into my brain. You literally wrote a blog and a book about this stuff. You are the godfather of FI at this point. I am coming to you. How are you not thrilled at the success story that is me coming to you declaring that this is what I want? But he was not on board. He was like, What are you gonna do? You're gonna be so bored. He's like, work is productive, work is good. He's like, I loved my job. You're so good at sales, don't you wanna stay in it? And Justin, I was like, what the fuck?

Like what universe is this? So it was fear, and it was also being taken aback by my dad's reaction of like, did I miss something? Like what's going on? So those were the big main reasons. And honestly, we just got to a point where two years I had been like, maybe we could do this. And then nine months I was like, I can't do this anymore. And then even with Dad's reaction, we had a lot of conversations about it.

And a lot of it was just like, listen, I'm a big girl, I've done the math, I'm talking to you about it, I've read the book, I get why you think it's scary and I am scared by it, but I also feel confident that if this is a bad decision, I can go back. It's not gonna go anywhere. And the interesting thing about this too is I made a plan where I said, and this is what I told my bosses and my job and everything. I didn't say that I was quitting forever, retiring. I said, things have been a lot. I need to take a step back.

I'm gonna take a step back for six months. I'm not saying hold the job for me. I am saying that in six months, I would love the opportunity to reassess coming back here. And Dad loved that plan. My job loved that plan. And funny enough, six months later, the people who came knocking on my door was my old manager and my old bosses. And I was like, no, I'm good. We're great.

Justin: You tricked your dad. I'll go back in six months. He's like, okay, then you can do it.

Jessica: Yeah. He's like, Yeah, yeah, yeah, that's a good point. He was like, Why don't you trial run this whole thing? And I was like, Sure, sure, sure, we'll trial run this. And then six months later he's like, How you feeling? I'm like, This shit's great. What do you mean? Yeah.

When JL Collins Didn't Want His Daughter to Retire Early

Justin: And I really appreciate you sharing this story. Obviously, you know I love your dad. He's become a great friend and mentor of mine. But to me, it's really interesting to see that even the man who wrote The Simple Path to Wealth, which is really a blueprint of how to retire early, was afraid of his own daughter retiring early. And it just shows, you know, his own humanity as a loving, caring father. And most parents, what they care about most is the safety of their child. And even though you were totally financially independent, he was like, What do you mean?

The unproven path that he did not take, because JL worked until his late 50s or 60s, is retiring early. So this is the unsafe path, even though he knows tons of people who retired early. Still, when it came to his daughter, he was like, Wait a minute. This isn't safe. I don't know this path. And I just love that you were open in sharing that. And I love that despite him writing about this shit for over a decade, he still had a challenge when it came to his own daughter retiring early.

Jessica: I think the other thing I would add to that is, it's interesting that my dad wrote The Simple Path to Wealth, but he never actually walked it, right? He retired in his 60s, right? So he did the very traditional path to retirement. And he loved his career. Like he loved it. So I think the other element of that for him, too, was a father wanting his daughter to have a fulfilling life. And I think there was a part of him that was worried, because something that brought him so much joy and satisfaction was his career. And he was in sales, right?

So his joyous, fulfilling sales career was a path that I had started on. And I also just think it was a father having concern that his daughter wasn't going to have the joy that could come with a successful, fulfilling career. I think now on reflection, that was also a big piece of it, too. Of, hey, you are allowed to, and you've done the thing, but have you really thought about this, right? Like, is there a way that you could still have this beautiful thing in your life that I had that brought me so much joy and so much satisfaction?

And I can understand as somebody who's never had kids, I can understand how that's a thing for a parent to get over because you just want your kid to have the best that they can. And if something was super meaningful for you, why would you not want your child to potentially have that opportunity?

Career Prestige vs. Freedom: Choosing Your Own Path

Justin: So, 100% agree with you. And it's just, you know, I think a big part of that is you choosing to take your own path in life and him learning to be okay with that if it looks different than the path he took. And you know, it's so funny you said that about your dad and the sales career thing because when my company came to me and asked me to be chief revenue officer, I told my dad and he was like, yeah, you definitely should do that. And thank fucking God my wife was like, No way, you wanna be free. You don't wanna manage people.

Jessica: Voice of reason, yeah.

Justin: And thank God I listened to my wife and not my dad. And again, my dad's just, you know, he saw the proven path, the title, the prestige, the money, and it's safe. So of course he's like, Yeah, do that one.

Jessica: And I also think it's generational. I don't know your parents' age, but I wonder if there's a generational thing of success is whatever the next step is in the career. So of course, I have no problem believing that your dad was so excited for you to have that opportunity presented, because in a different generation, why would you not take that? Like what reason could there possibly be to not accept this amazing opportunity for career growth?

Justin: Yeah. 100%. And my dad is the same generation. He is five years older than JL.

How Jessica Became an Author After Leaving Corporate America

Justin: Alright, Jess. So you left the sales job, corporate America, despite your dad's wishes not to. How the heck did you start the path of becoming an author? So you have this amazing book coming out, The Simple Path to Wealth Workbook. And for those who don't know, because we didn't really talk about it in the intro, JL's been on the show, I think, three times. The Simple Path to Wealth has sold over a million copies. It is a blueprint, as I mentioned, to achieving financial independence. And I want to know how you actually went from corporate America to now a published author. So walk me through the genesis of your foray into becoming an author.

Jessica: Sure. So like most things in this life, all roads go back to Dad. The pieces all kind of fell into place, to be honest. I quit my job, and then along those same lines, Dad was starting to have conversations, because he had originally self-published The Simple Path to Wealth, about pulling in a publisher. And I was just trying to help him through those conversations, you know. What does that look like? What do you want? And I am somebody who is, by nature, interested in just learning about how things work in all facets of life, right?

So I'm sitting here being like, well now I have all this time and you have this cool opportunity to have like an agent and publisher. Cool, let me be a part of those conversations because why not? And my dad and I are really close. We have that kind of relationship. So I'm involved with these conversations between him and the now publisher. And the idea behind it was, Simple Path was published almost a decade ago at that point. So it needs to be updated. There are certain numbers that are outdated. Maybe there's certain things that have changed that would be beneficial to add in.

And Dad doesn't want to do it, but it should be done. And I was like, I'll do it. I'll help. I'll help edit it. I'm not writing anything. I'm not, because we all know I'm not interested in this stuff, but I'm not actually writing anything. I'm just editing. And that's cool. Show me what this is like to get a book published. What is it like to go through the editing process? So I did that. I'm working closely with Dad. I'm working closely with the team. And I just think it's really cool. And it was a cool way for me to learn.

It was a cool way to fill my time, do a cool project with my dad, get to know the team. Fast forward, there is a lot of conversation in the nonfiction book world of having a workbook, right? And anybody who doesn't know a workbook, it can be a standalone, or it can be an accompaniment to another book.

Basically, I like to think about it as if you ever had a textbook in school that was the actual textbook, and it came with like a spiral-bound paper workbook, and that would be where, okay, you read chapter one and then you go through the questions in the workbook about chapter one just to check your understanding, right? I had a lot of those in college. I don't know if other people relate to that. So with this new relationship with these publishers, a topic of conversation came up of like this actually should have a workbook to it. It kind of lends itself really nicely.

There's a lot of cold, hard facts and things you have to think about for the simple path, but there's also some other things that people are always asking about. It could be nice to have an accompaniment. So then the conversation changes to who's gonna write it? Dad doesn't want to write it because he just doesn't want to, but he's also never actually walked the path. He's not really the best person to write this workbook. I am. And that was conversations that I had with Dad. That was conversations I had with the publisher. Do you even want me to write this?

From Dad's point of view, do I feel like somebody that you trust to carry the legacy and also create this addition to this monster of a book that you've created? And everybody agreed. And I was up for the challenge. I was like, let's do this. Let's make it happen. And I have had enough conversations with people that I feel like I could do this. And I feel like I could do it justice. And we did it. And we started at the beginning of the year. And here we are, August, and it's getting ready to go to print. And it's gonna come out at the end of the year.

Justin: And if you hadn't early retired, this would have never happened.

Jessica: Exactly. If I had stayed at that job, Dad would have had to do a lot more work. I wouldn't have had time.

Justin: You wouldn't have even had time. You'd be like, sorry Dad, I'm too busy closing deals.

Jessica: It's your book. You edit it. Yeah, exactly. 100%.

Justin: Yeah. So once again you are the reason. Not all roads lead back to your dad. All roads lead back to Jess.

Jessica: All roads lead back to me being the girl that wouldn't listen. Justin, you are brilliant because once again I was the girl that wouldn't listen to her dad when he said, Don't quit your corporate job.

Justin: Yep. And it's so good. And now you get to go back to Dad and say, because I didn't listen to you, now we got the updated Simple Path to Wealth that you didn't have to do all the work. I did a bunch of it. Now we have a workbook that I did and you didn't do.

Jessica: He never looked at it. Yep.

Why Jessica Wouldn't Let JL Read the Manuscript

Justin: So tell me about that. He told me yesterday that you wouldn't even let him look at the manuscript until it was finished. So tell me about why.

Jessica: Well, it's two reasons. One is to respect his wishes first and foremost. He was really adamant that he just didn't want to do it. He didn't want to be involved. He didn't want to do any of the work, etc. So respect his wishes. But the other thing too is my dad is my biggest supporter. So I knew that if I asked him for help, he would say yes. Like he's not gonna say no to me in that capacity. But the other thing with Dad is he likes things to be his way.

And it was really funny because I remember as a kid, I had to learn at a really young age that Dad wasn't the person, even though he was an English major, he wasn't allowed to proofread my papers. Because I would give him a paper to proofread just saying, Hey, can you check for spelling and grammar? And he would return it to me with a completely new, rewritten paper. And it's important for me to say that. I was an excellent student. I was a straight A student. I didn't need you to rewrite my papers. My papers were getting A's.

But he would just read them and be like, well, if I was writing it, I would put it in this order. Actually, I'll just write it. And there were lots of times I was like, Dad, you can't. Forget it. I'm just gonna proofread it myself. And if I have a spelling error, that's okay. So I knew that if I gave him an inch, he would be really willing to help me. And I would be so appreciative of it because who's the better person to help on this workbook than the guy who wrote the OG? But I also knew that I wanted this to be what I wanted it to be.

And this was my vision. This was what I thought would be helpful based off of conversations that I've had. And candidly, as the person who had the tools but didn't understand the why, I understand that most people are in that position. They kind of like have the tools, but their why might not be set, or they have the why, but they don't have the tools. And let me write it. Let me create the thing that I think would be the most valuable based off of my experience walking the path and conversations that I've had. To his credit, he was really respectful about it.

Finding Your Why for Money and Financial Independence

Justin: That's so powerful, Jess. I think one of the beautiful things about the workbook is it helps you with both the tools of implementing what is taught in The Simple Path to Wealth, but also helping you answer the deeper question of what is the why of doing the simple path? And I'm speaking as if I'm the listener: why do I want to achieve financial independence? What is important in my life? What is unique to me? And what's important to Justin is different than what's important to Jess or to JL. And we all have to answer that question: what is the why behind our money?

Jessica: Yes, 100%. I think at a certain superficial level, people have an answer to that question, but the superficial answer isn't the thing that's going to get you to financial independence if that's what you actually want. You do have to dig deeper and sometimes that takes time and sometimes that's not comfortable. And then people will shy away from it.

Justin: 100% agree. So I work in the coaching capacity with people on both fitness and money. And one of my core principles is you have to have a strong why for your fitness and for your money. Because if you don't, guess what? Everyone has something called life happen to them, and your goals get thrown off course. But if you have a strong why or a strong set of whys, then you can stick to the path of achieving a certain fitness goal or achieving a certain money goal.

But if you have a weak ass why or no why, then as soon as life happens to you, those goals get thrown out the door.

Jessica: Yeah. And it's interesting because when it comes to money, I actually think everybody has a really strong why, like why they spend the way they spend. But I think people get embarrassed about it or they don't want to admit it because we should ourselves, right? I should do this, I should do this, I should do this.

And then that becomes a really interesting cycle of so now we're just not gonna talk about it or dig a little bit deeper or do the thing to make the change because we feel embarrassed, or we feel like we should think a different way, or we should have a different why, and so now we just stay stuck.

Debt, Shame, and Being Programmed to Consume

Justin: Or we get into debt and we become ashamed of that debt and shame loves secrets. So we don't talk about it. So then it just gets worse. And we should have not gotten into debt and we should on ourselves. And then we feel ashamed and guilty. And then we just avoid money and it just gets worse and worse. And we all go through life with different circumstances and different life experiences and different parents. And unfortunately, most humans, especially in America, are programmed to be consumers and programmed to spend beyond one's means. And I'm pro-capitalist, but one of the problems of capitalism is it's based on people continuing to consume.

And so if you are unable to learn the skill of saving and investing, which is kind of the opposite of consuming and spending, then you get stuck in this machine and you can't get out from underneath it. So even if you fucking hate your job, you can't quit because you got bills to pay.

You Can Choose a New Money Why at Any Time

Justin: And so I love that you said everyone has a why of why they're spending in a certain way. It's 100% true. But just because that is one person's why at one point in their life doesn't mean you can't say, wait a minute, I don't want that to be my why anymore. And I'm a great example of this. In my mid-thirties, my why of spending all my money was to look like I had made it. So I drove the Range Rover. I ate out at the nice restaurants. I wore the nice clothes. And I looked rich, but I was fucking broke and I was ashamed.

And I definitely did not talk about money with anyone other than pretending that everything was okay. And I still remember to this day waking up stressed at 2 or 3 in the morning about my debt. But having to pretend to the rest of the world that everything was okay and dandy. And I was doing great. And then, fortunately, your dad's book, The Simple Path to Wealth, as well as all the other FI bloggers, made me realize holy shit, there's this other path of financial independence. And so I chose to change my why of money. So my why was no longer to look like I had made it.

My why became my freedom. Because even though I actually loved my job, I really did. Now I wouldn't do it for free, but I love the money I made. I really loved the people I worked with. I loved what we did, but I never liked the idea of being beholden to other people because I have bills to pay. And so once I understood, wait a minute, there is a path to financial independence where all work becomes optional. Doesn't mean I have to retire, but guess what? If I get a boss that I don't like and I'm FI, I can quit.

Or I can say, No, I don't want to do that and they can fire me. And so the point I'm trying to illustrate is we're all programmed by parents, society, peers on our money why of both spending and saving or not saving and investing. But at any time you can choose a new why for that. And one of the things I love so much about the workbook is it empowers you to get clear on what why you want to choose.

Jessica: Yeah, yes. And I think it's so interesting because I think people forget how much control they actually have. Right? You can't control if you're gonna get a new boss. You can't control if your company is gonna fire you or get bought out, whatever. You can't control if your landlord decides that we're gonna hike up the rent or property taxes change. But you can control a lot in your own life. And your why is one of them.

And I think it's wild that people forget that, but I also understand when you think about how we've been conditioned, when you think about how we've been conditioned to work and what your life should look like, we have been told that our identity, our satisfaction, your happiness needs to come from your job because you spend so much time there. And that's just wild because there's so much about your job that you cannot control. So you're telling me that my identity and my satisfaction in this one life that I have is supposed to come from this thing that I can't even control? That doesn't sound great.

And to your point, you did like it, but what if one day your why is nothing to do with your job? Might as well make sure that you've made the choices for it, planned accordingly.

Getting Laid Off With Financial Independence Already in Place

Justin: Or, as you mentioned, we got acquired and I got laid off. So thank fucking God I'd been planning, because when it happened, I was like, well, okay, I guess I'll just actually use the FI that I've built. So it wasn't this big scary thing. And I knew it was coming because I knew we were either gonna go under or get acquired. And it actually took way fucking longer than I thought it would. I thought within a year or two of COVID, we're either gonna go under or get acquired, but it actually took four years.

Jessica: Whoa, more time to make money.

Justin: Exactly. So I just kept making money and kept getting more FI. And so even though I didn't know what I was gonna do with that FI ultimately, similar to you, because it was in place, I had all the options open to me. So it's like, cool, I could go get another job, or I could just not work, or I could do more online fitness and money coaching, or I could podcast more, or I could go explore things, or I could do whatever the hell I want.

Inside The Simple Path to Wealth Workbook: How It's Structured

Justin: So let's talk a little bit about the actual workbook. So I wanted to break down real quick for the audience the way it's structured, because I think it's really structured in an awesome way that makes it very easy to understand and easy to put into play. So part one is the destination. Part two is where is your money going? So this is like debt, spending, saving, investing. And then part three, probably my favorite part because it's where I'm at, is FU money, relationships, the life of FI, and kind of where I'm at over the last two and a half years and for you the last two years.

So it's a little over 180 pages, the whole book, but it's a great read. If anyone has not read The Simple Path to Wealth, which is, in my opinion, the most enjoyable personal finance investing book I've ever read. Because most finance books are boring as shit. But JL makes it fun. And what I love about the workbook that you wrote is you tell your own story, and there's a lot of stories in it, and it helps people understand these different concepts from the original book, The Simple Path to Wealth, but shown through someone who's actually walked the path.

FU Money vs. F*ck It Money

Justin: And you know, one of the things I loved about the workbook was the distinction that you talk about, the F it money versus the FU money. So explain that to me and the audience.

Jessica: Sure. So that was kind of something I came up with on a whim. And to be frank, there is no right or wrong way to think about F it or FU money. If you've never heard of FU money, it is something that my dad taught me, surprise, surprise. And it's not financial independence money. So FU money is not that you never have to work again, but you have enough in your investments to walk away from something that's not serving you, right? And so think big-picture stuff.

Maybe you have a job, and we've been talking a lot about that, and you have a boss that you don't like anymore, and you're just like, F you, I'm done with this, and I'm gonna leave, and I don't have a plan, I don't have another job lined up. F it money, to me, feels like something on a smaller scale, but still that same mindset, right? We're not talking, F it, I'm not gonna pay rent this month or I'm not gonna pay my mortgage. But when you're thinking about reaping the benefits of this path, this simple path to wealth, maybe before you've actually hit financial independence.

FU money is, I'm walking away from something that's not serving me. F it money is, I'm actually gonna conserve my energy. This is a small example, but you get a package that's stolen. And maybe the items in the package is worth like a hundred, two hundred dollars. And now you're sitting here being like, God, that really sucks. But we all know that customer service these days also sucks. And if you call, chances are you're getting a robot and you're gonna have to yell at the robot for 10 minutes, representative, representative, representative. You're maybe eventually gonna get a representative.

Maybe you're not, maybe you're gonna have to do all of this email. And now you're spending so much time and energy trying to get a hold of a person to explain the situation to either refund you or get the box sent back to you, the package sent back to you. And it's just like fuck it. Like, I don't have to worry about that, right? Like, I don't have to worry about that $200 because I have been diligent and I have been consistent on this path, and I'm working towards financial independence. Might not be able to retire yet or walk away from working completely, but you know what?

My time and my energy is really important to me. And dealing with this, not worth it. I'm just gonna bite the money. I don't even know if that's the right way to say it. Bite the money. I'm not gonna worry about the money. That's what it is.

Justin: Yeah. I'm just gonna eat the cost.

Jessica: Thank you, that's what I was looking for. I'm just gonna eat it because my time's important.

Justin: No, it's totally true. Think about a busy parent who needs to take his or her kid to soccer practice and he or she's stressing about this lost package, but she's been saving 50% of her income and investing for three and a half years and has close to half a million invested. Does she want to stress out about that package or just be like, fuck it. I'm taking my kid to soccer practice. I'll either just order a new one or when I have time I'll deal with it. But right now I don't. So I'm just gonna go enjoy my life because I'm on the path and I've been diligent.

Buying Back Your Time: Car Washes, House Cleaners, and What's Worth Your Energy

Jessica: One of my favorite examples is, last year was my first time ever getting a car. I've never had a car before. And I'm learning that it is a very annoying thing to have. It needs a lot. And I was like, cars get dirty. That is so inconvenient. And I tried to clean the car. And it got dirty. I wasn't doing a good enough job. I didn't know what products to do. And finally I was like, fuck it. I'm just gonna pay somebody to clean it for me. Because I don't want to spend the time to learn, how do I clean upholstery? What cleaning supplies do I even need?

Nothing in my kitchen works. Like I don't wanna put my energy towards this. And it sounds so small and so stupid. And I'm sure there's a lot of people listening here being like, God, she can't learn how to fucking clean her car. I could. I could. I don't wanna. I don't wanna. So fuck it. I'm just gonna pay somebody else to clean it. It's not just about like the package going missing is annoying and now I gotta deal with it. It's also just where do I wanna spend my time? Where do I wanna spend my energy? I'd rather go to pottery class.

Justin: 100%. Or you could be like me and I don't even know if I've washed my car in the last five years. Now, I have a silver car, which doesn't ever really look that dirty. So that's a trick. If you have a white car or a silver car, it's actually very hard to tell if it's dirty and we live next to a beach and I'm at the beach all the time. So there's always sand in my car. And I'm just like, fuck it, I don't care. Who am I trying to impress? My wife loves me. We've been together for almost thirteen years. She doesn't care if my car is dirty.

Jessica: No, she actually probably brings some of the sand into the car because you go to the beach together. Yeah.

Justin: 100%. Well, we take her car. She'll get her car washed every once in a while. She cares a little bit more than me, but still it's you know, she'll usually just go to a car wash and have it done there when she does do it. But I think another thing that this made me think about is and this is more for the people that are well on their way to FI or even post FI, is applying the F it term to shit you don't want to do. So my wife and I have a house cleaner come every other week.

They deep clean and they do all the stuff that we just don't want to do. And I swear to God, getting a house cleaner has been the best investment I've ever made in my marriage. Because no one wants to clean the bathrooms.

Jessica: Right, exactly. And you probably have other things that you want to do. Like play pickleball. Like record a podcast. Or go to the beach. What is worth your time? Where do you want to put your time and energy if you have the choice?

Justin: Or go to pottery. 100%. Now, obviously there's nuance to this because if you're at the very beginning of your FI journey and you have nothing saved and invested, probably not the best use of your money to pay a few hundred dollars to have a house cleaner, unless that allows you to go make two to ten X whatever you're spending. And that's the nuance, because as you get further down the path of financial independence, you start to buy back your time and really buy back your highest expression of living your best life. And living my best life means I don't clean the house at all.

So I might wipe the counters down after I make a fucking mess, but I'm definitely not deep cleaning the bathrooms or mopping the floor or vacuuming the rug or any of that.

You Don't Have to Wait Until FI to Enjoy the Journey

Jessica: I'm so glad you brought that up because there is nuance. There's nuance to all of this stuff, right? The stage that somebody is at on this journey is gonna look vastly different than somebody else. And that's how I designed the workbook. There's a reason why the conversation about FU money is in the third part, right? This idea of like, we've done all of the other shit. We got our ducks in a row. We are further along. Now we have that. But if you are starting out, there's other things that we need to check off on that list before we can get to FU money or F it money.

The beautiful thing about FU money and F it money is a lot of people are like, God, I have to be on this path for at minimum 10 years, but for a lot of people it's longer. I have to wait so long to reap these benefits. No. If you get out of debt, you make sure you're saving and investing, and you understand where your money is going, when you get all of that figured out and you start being consistent, you don't have to wait 10, 15, 20, 30 years until you can pull that trigger to enjoy this. Like, enjoy the journey now.

Part of that is recognizing when you have FU money and F it money, and that's so empowering. That's so empowering because you might not be able to walk away, you might not be financially independent, but wow, you can really start living life on your terms a little bit more. And that's really cool.

When Frugality Goes Too Far: Savings Rate vs. Enjoying Life

Justin: And that's something I think your dad's done a good job of talking about in the book and in conversations I've heard him have on various podcasts is you get more and more power as you go further and further along the FI journey. So, you know, in the beginning you might not have the power to walk away from a toxic job or pay for a house cleaner. But at some point on the journey, well before you hit FI, you do get that power to hire a house cleaner and leave the toxic job. And then also at that same time, you start to realize like, hey, it's great to be frugal.

It's great to save money. And one of the reasons I want to talk about the F it thing is because I think a lot of FI people get so obsessed with being so frugal that they actually make their life suck when they could just say F it and actually just enjoy their life because all their habits are so fucking good 99% of the time. The one time where the package didn't get delivered, they don't need to spend three hours saving a hundred dollars. They should just go fucking watch Netflix or go to the beach or go to the pottery class.

Jessica: Yes. I love that you brought that up because I think it just speaks to how personal this journey is. Caveat: it's your money. Do whatever you want. I don't care how you spend it. I'm not gonna sit here and fight with how you should spend it. But I do think it's something, and this is why understanding the why, and yeah, you wanna understand the 4% rule, you wanna understand the math, but you also need to understand the more like emotional questions about this and how it pertains to your life.

Because for me, somebody might say, I'm gonna grind it out and I'm gonna deprive myself of everything that is joyful because I want to get there in eight years. And you know what? That's on you. That's great. That sounds miserable to me. But in my brain, I'm like, well, let's think about this for a little. Think of how you want to live your life. Think about the fact that you might decide to deprive yourself for eight or ten years, but you don't know your health in eight or ten years. You don't know your energy levels. You don't even know if you're gonna be here in eight or ten years.

So would it make more sense to grind it out? That's cool, think about it, or maybe live a little bit more. And you know, I'm all for a high savings rate, but if you're gonna save 90%, could we figure out a way to save 70% and maybe enjoy life a little bit more? Again, it comes back to what are you looking for? What do you want to do? What are you trying to achieve? And if you have the habit built, if you know that you are saving, you are always going to pay yourself first. You are not going to get into debt. You're going to live below your means.

You're going to invest the surplus. Cool. Great. Now we can have a little bit of flexibility because you know you're always going to do that. You know you're going to be consistent. How do you enjoy the ride? Because it is your life. You only have one life.

Three Years Without Restaurants: Spending Every Dime on Freedom

Justin: And I've said this on previous podcasts, but I think it's worth sharing here. When I discovered financial independence, I decided that I was gonna pursue it with a vengeance of having started late. But while pursuing it, I was gonna have as much fucking fun as possible and feel as free as possible. So I actually did not eat out at restaurants for three years. Because I was on this mission. But for me, it was this fun experiment. And it was temporary. It wasn't forever. It was just at the time when I first discovered FI, every extra $10 I could throw into my investments was my highest happiness.

Now I eat out two to four times a week, right? But the whole time I was pursuing FI, I was having so much fun. I was feeling free. I wasn't like, God, I can't go to the restaurant, but I really want to go to the restaurant. It was like, I don't even fucking care about the restaurant. I want to fucking go have a picnic and fucking save this $80 and put it in the investments. And then later, now I'm like, fuck it. I don't want to fucking pack a picnic. Let's just go pick some shit up from Whole Foods.

Jessica: Because you knew your why and you've done the work to trust yourself to be consistent. I think that's the other caveat here. And again, this is why I designed the workbook in the order that I did, because I wanted it to be a book that you could pick up and go to the section that relates to where you are right now. Right. The honest truth is if you're somebody who has decided that financial independence is something that you really want, but you're in a lot of debt, that's the first thing you have to tackle and you do have to grind it out.

The conversation you and I are having is probably not gonna be on your radar until you can get out of that hole that is debt, right? But part of the reason you were able to have the attitude that you have now, which is like, fuck it, let's go out to eat, is because you did the work ahead of time, right? And you said that you were having fun with it, which is great. But for a lot of people, that's not fun. For a lot of people, that's really forcing you to hold the mirror up and be honest. And that's really scary.

But if you really want this, you have to do this. You have to build the habits, you have to make the changes, you have to do the audits. But oh my gosh, once you do it, if you just trust yourself and give yourself the opportunity to be a little bit consistent and build those habits, ooh, you're gonna have a lot of fun in like a few years. And it's gonna be cool.

Justin: 100%. Yeah, and for me, when I was doing that those three years of frugality, it's because my why was so crystal clear. My why was my freedom. And so it was like, fuck a restaurant. Like, I wanna be free. You know? Yeah, I wanna buy my freedom. That's the best thing I can spend my money on. So now I have my freedom. So now I spend my money in other ways that are aligned, you know. I have way more pickleball paddles than I need. At one point I had three gym memberships because I wanted to be able to go to three different gyms.

And one of my values is fitness and health. So it's like, fuck it, let's have all three of them. Why do I have to seclude myself to just one of them because I'm trying to be frugal when I already have my freedom? I don't need to be frugal.

Jessica: Yes. My dad has this great saying that he goes, I spent every dime that ever came my way, I spent it on my freedom. And that's exactly what you were saying with like that $80 is going to be buying my freedom. And now you have your freedom. And you can spend your money whatever you want.

How to Talk About Money and FI With Your Partner

Justin: So let's say you're a listener and you're like, hell yeah, I'm so excited to master the fundamentals and pursue this thing called financial independence. And I know my why, but you have a romantic partner. How do you start to talk about money with a partner? And I wanna look at it through two lenses. One, let's say you're like me and discovered FI after you've already been in a relationship for a while. How would you recommend somebody start to have that conversation? And then I'll remind you the second part, which is let's say you're getting into a new relationship. How soon should you talk about money?

So let's talk about for the people who've been in a relationship, because a lot of people discover FI after they're already in a relationship and they've never talked about money at any depth with a partner.

Jessica: Yeah. So, I know that finances can be a really hard thing to talk about. And in full transparency, I also realize that I'm not the expert on this. I'm still so private about my finances, which I know everyone's probably like, that's so ironic. Yeah, I know. And I don't even know that I have the best piece of advice, but at this point, through my own experiences and just through talking to people, I've met so many people in this community who found FI and dragged their spouses along.

I think if you have a spouse or a partner or even a family member, and you're the one that's discovered this, you're on the journey. Maybe you've already achieved financial independence, or maybe you're well on your way. I am hopeful that you already have a foundation of good communication with whoever this person is, right? And we've already talked about finances to some point because I think we all know, regardless of FI or not, having financial conversations with your partner is really important just to understand where do we want to spend our money? What are our values, right?

I think having a conversation about financial independence with a partner that you already have is probably going to be really scary because this is a unicorn path. You're going to go against the grain. You might be the person that comes in and says, Our house is actually a terrible investment, right? Or you might be the person that says, I want to achieve financial independence, and actually I've decided that I want to get rid of these expenses. Maybe we have a joint bank account, maybe we have a joint credit card, and I want us to start saving X amount of money, and we're only saving this.

Those are scary conversations for you to tell somebody that you've lived with or been with for a certain amount of time because you're kind of uprooting their life. And if they're not bought in, that's really scary. So it's situation by situation. You can be on the path by yourself. That sounds really scary, and people don't like to hear that when you're in a relationship. And I get it, right? You've built this life together. Doing something on your own might feel wrong or like a betrayal. You can do it. You don't need everybody to go on it with you.

You just need to make sure you don't get pulled off of it. Now, for every current standing relationship, that's gonna look fundamentally different because I don't know what your finances are. And like I said, I'm not the expert on it. If everything is so intertwined, it might need to be a conversation where you do have the hard conversation that says this is something I want. And if you're not bought in, I'm gonna do X, Y, and Z to figure this out. It could also be that you say, Hey, this might feel scary. Let's do some of these workbook activities together, right?

Because there is a whole section in there about relationships and there's some partner activities just to really get crystal clear on your whys, your beliefs. Where do we overlap? Where do we differ? What similarities? What differences do we have? Right. Maybe that's a baby step intro into it. But fundamentally, I think if this is something that you want, you should feel empowered to do it and be okay that you and your partner might be on different pages for the moment, as long as we're communicating and we're not pulling the wool over anyone's eyes.

Your Partner Doesn't Have to Pursue FI, Just Support the Vision

Justin: I love your answer, and I'm going to tell you why, for a few reasons. As a coach, I talk to many people about financial independence. And I can't tell you how often they blame their partner for the reason they're not making the progress that they want to make on their FI journey. And I always tell them, look, let me tell you about my journey to FI. When I discovered it, of course, I tried to get my wife to read some Mr. Money Mustache articles, and that shit blew up in my face. And ultimately, what I realized is exactly what you just said.

I don't need my wife to be fucking crazy like me and not eat at restaurants ever for three years. So I said, Hey babe, I'm not gonna eat out in restaurants for the foreseeable future, unless someone else is paying. I don't care if you take your money and go eat out with your friends. And she said, Great. Guess what? She went out with her friends, had lunch, dinner, etc. And I saved and invested every fucking thing I could. And I got us to FI really fucking fast. And most of the money in our current household up until recently was from me.

And all I needed from her was to support my vision of financial independence. I did not need her to save and invest. All I needed her to do was not take away from my ability to save and invest. And support the vision of us getting to financial independence, even if I was the main fucking driver. And guess what? I was happy to be the main driver. So I just needed her to support my vision. I didn't need her to do what I did. And I love your answer, because I totally agree.

Many people who discover FI are gonna have a partner who's just not interested, and that's okay, as long as they support you pursuing it, right? That doesn't mean they have to add to the investments or do anything. It just means they need to support you doing it.

Jessica: And not get in the way. Yeah, if this is something you want, you can do it.

Justin: 100%. So obviously, if my wife was like, No, I'm gonna, you know, go buy a brand new fucking car and you're paying for it with your money from your job, I'd be like, that doesn't work. But obviously she did not do that. And all of this kind of coincided with when we first got engaged, and at the time we had racked up a bunch of credit card debt together and she had a car loan. And I just said to my wife, hey, I'm really passionate about financial independence. So before we actually get married, it's important that we pay off all of our debt, including your car loan.

And that's your car loan. So, like my expectation is that is paid off before we get married. And that is your responsibility. And she was like, heard. I'll work on it. And guess what? She fucking did it before we got married. We had zero debt. And so obviously I had some breakdowns and it wasn't always sunshine and roses and unicorns. And what I realized is it's really important to have these conversations, even though a lot of times they are hard.

Because if you haven't talked about money at a really deep level with your romantic partner and you've been together for some time, it's kind of really scary territory because it's unknown. We haven't been there before. We haven't had these conversations. But like anything that's scary, the more you do it, the more comfortable it becomes. And then eventually it's just we talk about money all the time.

Jessica: Yeah. It's a habit that you have to build. Money is so personal and I think money is personal because it's a direct reflection into your values. And I think that can be touchy. People don't want to get judged. Whether your values are good or bad, right? People don't want to get judged. And it's a habit that we haven't built. We also grew up in a society where money is taboo, right? All financial conversations are taboo. So it's hard, but it's a skill that you have to build and it's a muscle that you have to build. And you gotta do it, especially if you're gonna choose to be with someone.

Justin: 100%. Yeah. And money is a critical part of every relationship. And if you don't get aligned, and again, you don't have to be the same or behave the same around money. You just have to be aligned. And that's all that matters, right? So, you know, my wife continuing to eat out while I didn't worked great for us because we were aligned. Right. And so I want to encourage anyone who is newer to FI and is trying to figure out how to talk about money and FI with their partner: number one, you just gotta start to have these conversations. Number two, use Jess's workbook. There's a section in there for couples.

And number three is don't try to make them do what you are doing or want to do. Just ask them to support your vision of financial independence.

Dating and New Relationships While Pursuing Financial Independence

Jessica: You can't force somebody who's not ready, you know. All you can do is focus on your own journey. And then the second part of your question is, what about somebody who is on the path and then meets someone, right? Way easier question to answer, because you've got the upper hand. These are your values. You've decided that this is something you care about. You've decided this is a non-negotiable for you. Just like anything else with any other relationship that you let into your life, you get to decide how you want to approach it. You get to decide how are we going to have these financial conversations?

When are we going to have these financial conversations? And even more so, it's a personal preference. Maybe you want somebody who is 100% aligned with you. That's okay, that's your prerogative. But also, you don't owe this person anything. All you need to make sure is that they don't pull you off track. So you can stay on track. You can let them know. You can not let them know. But you have already created these boundaries. You created these boundaries before them. So as long as you just hold true to that, you should be fine. And then, of course, there's the conversation of maybe they're uncomfortable with it for whatever reason, right?

But that's okay because it's a new relationship. That's just part of what happens, right? But if you are on it and you meet somebody, this is your boundary. This is your non-negotiable. This is the path that you've chosen. Don't let anybody pull you off of it.

Justin: Yeah. And you can be kind and compassionate about it. And I think, you know, when you're getting into a new relationship, the sooner you do have these conversations about money and financial independence, then they're not surprised when, instead of spending a few hundred dollars on a fancy dinner, you choose a much less expensive thing and are focused on saving and investing. They're like, yeah, well we've already talked about this. I know that's important to you.

And even though he or she may want to do the expensive dinner, they're gonna understand why you don't wanna do it and they're not gonna be upset about it because this has been talked about already.

Jessica: And if they are, that's another...

Justin: Maybe you're not the right long-term partners.

Jessica: Right. Deciding factor. Exactly. It just becomes another one of those topics of conversations that you have when you meet somebody and you're deciding whether this is the person you want to invest any time with.

Life After Early Retirement: Redefining Ambition

Justin: So let's transition to the last section, which is life after leaving the job. You've been early retired for two years, and one of the questions I wanna open with in this section is that you've written that the hardest part was no longer having a clear answer when people asked about your ambition. So what did ambition mean in corporate life and what does it mean now?

Jessica: Yeah, so ambition in corporate life meant make as much money, hit quota, hit goal. So just backstory for anybody who hasn't been in sales in corporate America, you live and die by your numbers, right? You hit quota. If you go over quota, whether it's yearly quota, so like your yearly goal or your monthly quota or your quarterly quota, depending on where you work, there's extra bonuses, right? You get a little extra something. And there's also President's Club. So if you hit a certain percentage of your goal or your quota or whatever, you get that all expense paid trip to Mexico at that all inclusive.

So seductive, the word of this whole interview. And so that's what ambition was. It's like, what's your ambition? Well, my ambition is to hit quota. My ambition is to hit my goal. My ambition is to hit whatever that quarterly prize is. My ambition is to hit President's Club. And it doesn't have to just be with my job, right? A lot of people's ambitions, right? If you ask somebody what their ambition is, I would be willing to bet that the vast majority give you an answer that is related to whatever their job is. My ambition is to become manager, my ambition is to become a C-suite executive.

My ambition is to get this job instead of the job that I have. All are great. All are fantastic. I'm not here to tell anybody to change their ambition. But when I walked away, I remember the first time I told my dad, I was like, I don't think I have any ambition. And he was like, What did you just say? He did not like to hear that. I think he was just really shocked. But I was like, yeah, I don't. What is an ambition without a career to be attached to it? I don't know.

I grew up in this American society where you are a cog in the machine and you just work, work, work, work, work. And that is your value. That is your identity. And that's been that way my whole life. What's my ambition? Well my ambition is to graduate high school with straight A's and to go to university and get the best education that I can so that I can get the best job that I can. That's the ambition. And then I walked away and I was like I don't have an answer to that question. I've become more comfortable with it now.

The joke is, now I tell people I don't have an ambition. I just want to be here and be the best person and live the best life that I can live and just be happy. I don't have an answer to that question anymore.

Identity After a Sales Career: Where Drive Goes When You Stop Working

Justin: And I love this. It's so good too because, as I told you briefly before we hit record, I really struggled my first year of early retirement because I was so used to being the top performing salesperson for ten fucking years. And I had so much of my ego and my ambition all tied up into that. And then when that's gone, literally all I did was like, okay, how do I make half a million to a million a year with my online business? My coaching, my podcasting, my content creation, et cetera. Even though I was already FI.

So it's like, why the fuck do I need five hundred thousand to a million a year doing this? Like, why? So of course I built a course so I could make more money online. And then eventually about a year into it of being early retired, I discovered pickleball. And because I think anyone who achieves FI, and I think I can confidently say this about you, Jess, you just have a natural, innate drive and ambition. And you may be taking a current break from feeding that part of yourself. But when we're coordinating this interview, you had just gotten back from a scuba diving trip in Egypt or some shit.

So you have massive drive and ambition. Still, it's just manifesting and expressing in different ways. So previously in your corporate life, it manifested through being a top performer salesperson, through getting President's Club. But now it's expressing itself in writing a fucking workbook.

Jessica: Yeah, you're 100% correct. I think, and my dad and I have talked about this a lot, and I'm sure you've had these conversations with other people who have achieved financial independence. Humans are productive. We want to do stuff. And if you give us the opportunity, we will. We will. It might just look differently than this dream that we were all sold about find the job, do it for 60 years, and basically figure out a way to find satisfaction and happiness from it. But the reality is if you give us an opportunity to fill our time, we're gonna do it.

And we're gonna fill it with things that make us happy, that bring us joy. And you hit the nail on the head. It's like now the ambition is I've been taking pottery for 18 months. I want to get really good at it, right? The beginning of this year, I started taking pole dancing classes. I want to get really good at it. The scuba diving, the pickleball that you're talking about. It's like we all have ambition.

It just feels weird to give it a different font because our whole life, ambition seemed to me to be reserved for whatever that career was that you were going to do for the rest of your life. But again, taking that word and just writing it in a different font is really kind of empowering and a great way to just solidify that, like, nah, this is your life. Do what you want. Go play pickleball for eight hours.

Justin: 100%. And I think you just uncovered something. The opening question that I presented was, what are your ambitions for when you no longer have to work for money? And we as Americans, and I won't speak for non-Americans because I don't know what it's like in other countries, basically, our ambition is tied to money and work. But if you've won the money game and you no longer work, then it's really weird channeling your ambition in something that doesn't make money or doesn't involve traditional work. So pottery and pole dancing, I'm sure you could make money doing those, but you don't want to make money from them.

Jessica: I don't want to make money on either of those. And also, I spend money to do those.

Justin: 100%. I spend a fuck ton of money on pickleball.

Jessica: Yeah, I spend money on my ambitions now. My ambitions don't pay me. And that's okay. Oh my God, they're so much more fun. I'll spend money on them.

The Hobby Era: Pottery, Pole Dancing, and Pickleball

Justin: And I love, you know, you say you're in your hobby era. And I think that's so cool because that's one of the whole points, one of the joys of being a human is pursuing your hobbies. The things that you just enjoy doing because you enjoy doing them, not because they make money, but because you purely enjoy doing them. And for you in this current season of your life, it sounds like pottery and pole dancing is one of them. For me, it's pickleball.

And it doesn't matter what the thing is that you enjoy, but that's one of I think the biggest points of financial independence is to be able to pursue whatever you want that lights you up, whether or not it makes you money or it means anything to anyone else other than yourself.

Jessica: Exactly, exactly. Because you have the time and the resources. You can just live life how you want. And the cool thing is because you have the time and the resources with financial independence, you can just walk away. You're obviously in fitness. I have part-time jobs working at gyms as well. I'm a personal trainer and a group fitness instructor. And that was something I did part-time while I was in corporate America. And then it naturally like fell in my lap to do more of it when I had the time. And I love it. And the minute I stop loving it, bye. You won't see me again because I don't need it. Probably the same with you in pickleball. If you ever stop loving pickleball...

Justin: And podcasting. Like, I don't make a ton of fucking money from podcasting. I just do it because I fucking love it. Because I get to talk to people like you and your dad. And for me I'm like, hell yeah, this is two hours well spent.

Jessica: Yes, exactly. It's so fun. And this is why people who like discover financial independence get so excited about it and they want to tell everyone. I totally get it because it is so powerful. Like just to have the power to live your life however the fuck you want to live it. Doing whatever you want to do. Oh my God, I can't think of a better dream.

Justin: 100%. Even if it makes zero sense to everyone else.

Jessica: It makes sense to me. Makes sense to you. Yeah, that's why we're here.

Justin: That's all that matters. 100%. Pickleball, pottery, and pole dancing. Let's go. Awesome.

Where to Get The Simple Path to Wealth Workbook

Justin: Well, we've been talking a long time. I really appreciate you giving me the extra time. So let's wind this down. Obviously, everyone, go get the workbook. It's on pre-sale, and we'll release this probably before the book is officially published. November 24th, 2026 is the current publish date according to Amazon. So I'll put the link in the show notes. So if this comes out before it drops, go pre-order it. So it's on its way. It's an amazing workbook. I really enjoyed it. I think anyone who's either starting the path, on the path, or even at the end of the path, it's really powerful for various different reasons.

Jessica's Tips for Fitness, Money, and Happiness

Justin: But let's answer the questions I ask every guest on their first appearance: give us your tips, tools, and strategies for fitness/health, money/wealth, and life/happiness. So let's start with fitness and health. What do you got for us, Jess?

Jessica: So I'm actually gonna cheat. My one for fitness/health is the same for money: keep it simple and just be consistent. I think for both of those, maybe money not as much because there's a lot of noise in society, so it might not be as well known. But especially for fitness, we all know what we have to do. There's no secret to it, right? You peel back the noise, and it's the same stuff we've always known. Move your body, make sure you're eating right. That's it, right? Find any way to be consistent and just do it. It's not sexy. It's just not, right?

And candidly, and this is the same with finance. This is why I was like, I kind of have the same answer for both of them. If it feels sexy, it's probably not gonna work. And it's probably not worth your time. At minimum, it's not gonna get you results. And worst case scenario, it's gonna bite you in the ass. Either it's gonna end up being a money suck, or you're just not gonna lose the weight or change your body in the way that you want. So for both of those, you know what you have to do.

Especially if you're listening to this podcast and you know who my dad is and what he's written, you know what you have to do. For health and wellness and finances: just be consistent, keep it simple, shut off the noise.

Justin: I love it. What do you got for life and happiness?

Jessica: So life and happiness, I think people need to start asking more questions. I think we have become way too comfortable with not being curious. And I think that in every aspect of life, I think about it from when you're on Instagram or TikTok or watching the news and we hear clickbait tidbits of stuff, and we just don't take the opportunity to be curious and ask more questions to understand. But I also mean that with interactions with other humans. I think we have lost an ability to find understanding and give grace.

Think of how many conversations you've had with somebody and you've walked away and you're like, wow, they didn't ask a single question, a single follow-up question, right? And I just think if we try to be a little bit more intentional on, I'm gonna be curious, genuinely curious, and just ask you to tell me more about that thing that you said, right? Just tell me a little bit more about what you mean about this. Tell me a little bit more about anything, and just being more curious about the world, the people in it, the stuff that you see on the news, the stuff that you're reading, about a book, right? Anything.

I think if we could just become more curious again, I think you're just gonna learn a lot more. I think we're gonna become a lot more tolerant. I think we're gonna be more willing to give grace and empathy and compassion. And I think you're just gonna be happier for it.

Justin: Amen. Somebody said to me one time, it was actually in a wedding speech or whatever the dinner is before the wedding. And he said one of the best ways to be interesting is to be interested. And that's pretty much what you just said. And you're so right. When you have a conversation with somebody and all they do is fucking talk and they don't ask you a single question. You're definitely not excited about interacting with that person again.

Jessica: Right. Yeah. And with that interaction, it goes both ways, right? Maybe they were talking at you. Okay, that's not always the best feeling, but there were times where I've been in those conversations and I checked out, and I have this moment of reflection of, maybe I should have just checked in a little bit more because that's a thing that I think we all, including myself, could be better at. Ask a question. And ask a question with a genuine intent to understand and not respond.

Justin: Yep. Amazing. Everybody, Jessica Collins, author of The Simple Path to Wealth Workbook, the official companion to the New York Times bestseller, The Simple Path to Wealth. Thank you so much for coming on the show. Thank you for going extra long with me, going deep, and just bringing your full self to the show. I really appreciate your time, your energy, and your wisdom.

Jessica: Justin, thank you so much. This was so fun, and I really appreciate it.