Creating a Future of Flexibility & Financial Security with Jackie Kasper

Episode Number: 432

Episode 432: Creating a Future of Flexibility & Financial Security with Jackie Kasper

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This week on the Journey to Launch podcast, I’m joined by Jackie Kasper, a fellow Journeyer who’s intentionally building a life of connection and financial freedom. Jackie is a mom of two, a director of operations at a Chicago-based fintech startup, and someone who’s actively pursuing Financial Independence (FI) within the next 2–7 years.

We also dive into how she and her husband are navigating the journey together (even if they’re not always on the same financial page), the influence of motherhood on her long-term goals, and what reaching Coast FI means for her family’s options and freedom.

In this episode, Jackie opens up about:

  • How she got into the FI movement after being introduced by her sister-in-law
  • The mindset and financial shifts she made to go from spending freely to strategically investing
  • Buying her first multi-unit property with her brother at 25 and how real estate plays into her FI goals + much more.

Connect with me:

Jackie Kasper 0:02

You can do it all. You just may not be present or as calm. And I think that that's one of my goals, is to be present, to be calm, to have that connection, and obviously with less responsibility at a nine to five job, or six to four, whatever it may be, you know, it definitely helps.

Intro 0:26

Welcome to the journey to launch podcast with your host Jamila Souffrant as a money expert who walks her talk. She helps brave journeyers like you get out of debt, save, invest and build real wealth. Join her on the journey to launch to financial freedom in 54321,

Jamila Souffrant 0:52

if you want the episode show notes for this episode, go to journey, to launch.com or click the description of wherever you're listening To this episode in the show notes, you'll get the transcribed version of the conversation, the links that we mentioned, and so much more also, whether you are an OG journey or brand new to the podcast, I've created a free jumpstart guide to help you on your financial freedom journey. It includes the top episodes to listen to, stages to go through to reach financial freedom, resources and so much more. You can go to journey to launch.com/jump start to get your guide right now. Okay, let's hop into the episode. Hey. Hey, journeyers, welcome to the journey to launch podcast today. I have Jackie Casper, a fellow journeyer, someone who is in the thick of it, on the journey to financial independence, and wants to share her story. And she is a mom of two, a director of operations at an automotive Fintech startup based in Chicago, and she's been in the financial independence world for a little bit now, and she's focused on growing her investments, balancing life with two young kids, and challenging the status quo by intentionally choosing time and connection over consumerism. Love all that. She has a goal to reach fi within the next two to seven years. So I can't wait to talk more about that, and so she's on the show to share her journey so far and in insights and lessons we all can learn. So thank you, Jackie, so much for coming on.

Jackie Kasper 2:20

Thank you so much for having me. I'm thrilled to meet you and to speak to you today.

Jamila Souffrant 2:24

Yeah. So it's funny because Jackie, you were saying for press record that you were actually been following or have been aware of my journey before I quit my job, which I was like, oh my goodness, that's been a bit of time now.

Jackie Kasper 2:38

Yeah. So you know, thinking back, you were someone that was going through probably exactly what I'm going through now. You know, trying to set myself, my husband and my family up for success, to have the confidence to make decisions and live the life that we ultimately want, regardless of what that might look like. So I've followed along for many years, and I love listening to your podcast and learning all of the little tidbits. Yeah, yeah.

Jamila Souffrant 3:07

And now you get to be a part of the story someone else is gonna learn from you. So this is great, I guess. Let's take it back a bit. When did you first get into financial independence, and where were you at that point? I like to say there's like, we all are on the journey, whether we know it or not, but when we become conscious of, like, financial independence, there are certain things we have done up to that point that either like, Oh, that's a lot of work I have to kind of dig out of, or you're like, wait, I kind of did some things, right? So where were you when you first found out about financial independence in your financial

Jackie Kasper 3:38

journey? So I was lucky enough to have a sister in law who introduced me to this concept. I was working for a very lucrative, successful startup company. I was making good money at a young age. Unfortunately, during that time, I was spending a lot of it, you know, I didn't necessarily know that that I should be investing, that I should be thinking about my future. Luckily, I did. I did save. I did start and max out my 401, K, so I was doing the basics, but she really introduced me to the entire concept of setting myself up for success. So that is where I was at. So I definitely made a lot of changes. I was spending a lot trying to keep up with all of the coworkers, whether or not it be in Designer purses or clothing, shoes, sunglasses, all of the above. And once we started to think through what it was we wanted our future to look like. We really dug in and tried to learn as much as possible. How long ago was that? Would you say? Oh, gosh, that was probably 10 to 12 years ago. So since then, you know, we continue to. To try to hear other people's stories, learn from other people. I may have mentioned this prior. You know, there is no blueprint that that were handed that everyone can follow. If it was that easy, we we'd all be doing it. Everyone has the unique scenarios, situations, and so it's really just trying to find that balance and what works for you and your family totally,

Jamila Souffrant 5:24

totally true. So I guess if we go back a bit, you're doing this with a partner. So I'm curious to know if, when you find out about this, it was easy to get them on board, or did it take some work?

Jackie Kasper 5:37

It has definitely taken some work. I would say that I'm very focused on this. My husband is learning to get more invested in it. He is a numbers guy, so I wish that he did spend a little bit more time involved in it, but I think he also has the mindset. I have it figured out. I have it under control. He'll let me deal with it. But over over time, we've definitely continued to talk more about our money, what we're doing with our money. Obviously, you've heard of the the money date concept, and so I'm trying to incorporate those types of things more often, just so that we're aligned on where we're allocating our money.

Jamila Souffrant 6:27

Yeah. So I'd love to hear some of the changes that you've made and how you kept them up, because I know for a lot of people, you know, they hear about it sounds good. It sounds like you didn't have a budget before, maybe, and not you started with one, and you started to aggressively invest. So how did what did that look like on a day to day logical basis?

Jackie Kasper 6:45

Yes. So I think one, it's very important to have a budget, to understand where your money's going, what's important to you. Obviously, you talk a lot about this, understanding what's important to you. Where are you allocating your money? So really just identifying all of those expenses and then breaking it out into needs, wants, savings and ensuring that you're allocating appropriately? I think that that's probably, you know, the most important. Another thing that I just wanted to touch on was the fact that, you know, when I was making good money, when I was contributing to my 401, K and then wasn't sure what to do, I relied on a financial advisor, and that person took care of my money. And I would say that that was one of the first things that I did, which was tried to gain as much knowledge as I could and sever ties with that financial advisor. Once I felt confident in what my next steps were and what I needed to do, obviously, I no longer was paying an advisor fee. I no longer had high expense ratios that I was paying and and so really, the knowledge and confidence there was the starting point to continuing to do some of these things on my own

Jamila Souffrant 8:10

right. And I think that the whole gating confidence is something that we hold all people back. It's like the lack of confidence and not feeling like they can do it. And even if you currently have, you know, the different types of financial advisors and how they get paid. And then I don't think all of them, you know, are bad. I've used a financial well more planner, and was considering financial advising, actually, but decided against it, just because, you know, for me and where I am on my journey, I just, you know, I'm confident in being able to kind of manage things right now for myself, but I just want to say that it's if you are currently in that situation, you know it's okay to re evaluate and to not think about hurting someone else's feelings, because sometimes that there's a lot of emotional energy charged with like severing ties with someone or someone providing a service for you, but to have the confidence in yourself, to be not be afraid to ask the questions and that this is something that for most people, things are simple enough that you can do it yourself, but also if you do need the additional help or advice, that there are other options for you too,

Jackie Kasper 9:16

absolutely Yes, it obviously was not an easy conversation to have, but again, I think the confidence really helped that I knew why I was making a change. I knew how it was going to impact me, how much I would be saving and gaining from making this change. So that definitely helps.

Jamila Souffrant 9:39

It sounds like you had some real estate involved in your strategy, right?

Jackie Kasper 9:45

Yeah, I'll just give you the background there. My brother and I were able to purchase multi unit buildings back probably 15 years. Go at this point. And so that was a part of our strategy, you know, knowing that by investing in the buildings at that time would allow for a return at a later date. So that is a part of our strategy. Still trying to understand how that will impact us. Once the buildings are paid off, they are paying for themselves right now, you know, minor maintenance, but that is a part of our strategy, and something that we are banking on for the future.

Jamila Souffrant 10:35

Yeah. Well, I'd love to learn a little bit more about you getting into that just because real estate, for some people, is a option. They want to use or they're using. And some people are like, Nope, I don't want to deal with it. And so how did you get into it, and what are the pros and cons of using it as a strategy?

Jackie Kasper 10:52

Yeah, so I was again, 25 living at home. I graduated college and moved home, had no problem living at home. I know that's not for everyone, but during those years, I was able to save my money, so once I started to get the itch to move out. It's interesting. You know, it wasn't a long time goal or anything like that. But my brother and I just decided, okay, if we're going to move out, we might as well try to ensure that there is going to be a return on moving elsewhere. So we started looking at at multi unit buildings. Luckily, it wasn't just a condo, you know, we were, we were able to rent out other units, live in one, and that, that was the start of our journey.

Jamila Souffrant 11:50

Did you guys live together in one? Yes, we did. Oh my gosh. Okay, so you're, I know you're a parent also, right? But whenever I hear adult children being able to do things like that, I'm like, Ah, my kids, one day, are still going to get along and want to do that.

Jackie Kasper 12:04

Yeah, I agree. And like I mentioned earlier, my brother and I are very close. We always have been and and luckily, the the woman that he loves and fell in love with and married and brought into our family has only helped us even more. And so hopefully, you know, we're all succeeding on this journey together. Yeah,

Jamila Souffrant 12:26

I just, I love that, and honestly, this, like that collective, like pooling money together, and I mean, whether it's with a partner or family, and I know that, again, is not, not ideal for everyone, but if it's possible that community and investing together, that that can take you far, if you can find the right partners, because you can just get your money together, get mine, you know, your mind hive and work with each other and things that the other person's maybe not good at.

Jackie Kasper 12:55

Yeah, we always talk about that. My sister in law and I just so grateful that we do have a very similar mindset. Don't get me wrong, we love nice things, we love to travel, but at the end of the day, we are each other sounding board and our reminders that that isn't always the most important thing. And yes, we may not be able to do all that we want to right now, but that's going to ensure that we're doing what we want in a few years. You know,

Jamila Souffrant 13:33

right? And what I'm hearing too with your partner, you could correct me if I'm wrong, but he might not be as involved or on it as you, but he's also doesn't seem to be hindering or undoing the work that you're doing.

Jackie Kasper 13:43

I won't say absolutely not I was going to say that, but I think that he is learning and going about his own journey. So he has definitely made changes, made improvements, contributed along the way. Obviously, I started this 1012, years ago, and maybe didn't necessarily introduce it to him right away, because we weren't married at the time. It wasn't as serious as as it is now, obviously. But he he has come a long way, so it's just taken a little bit of a different path for him to get there, but he definitely understands the positive impact and the influence that this is going to have for my life as a mother and on his life eventually, when he's ready to hang up his suit and tie, whatever, however you want to say it, yeah, no,

Jamila Souffrant 14:39

but it's good, because I think too, like your partner doesn't have to be intense or as intense as you, I think just as long as they're not totally undoing any progress you're making, because sometimes you're pooling money together, sometimes you're separate with your finances, but that it doesn't have to be or look the perfect way, it's going to look different for everyone. And so don't. That's encouraging. Let's talk about how children changed your mindset, or how you're approaching financial independence. Because I know for me, they definitely encouraged me to want to seek out financial independence. But as they are getting older, you definitely see a change in the way I'm viewing my work life balance, even now as an entrepreneur. So how, how does that work for you with your kids.

Jackie Kasper 15:20

Yeah, so right now, I am working full time, and I think my goal eventually is to be able to spend more time with them and go part time. I don't know if I could say, you know, I'll never work again, but I want my energy to be dedicated to my family and building a connection and the memories, which is what I want to focus on. My job right now is very flexible, but with that, it still feels very hard to keep up with it all, with the home, with our kids, with their activities, dinners, cleaning, laundry, the list goes on. And so I would really love to be able to alleviate that pressure and that kind of rat race and focus on them. Before my son was born, I remember saying, Okay, I'll work for the next five years. I'll work while he can't remember, with the goal to change my lifestyle so that when he can remember, he remembers that I'm there, that I'm present, that I'm that I'm supporting him. And so I would say that that is that's the goal, that's where things may have shifted. Because obviously with children, expenses change, goals change, but ultimately that is what I want for the future. I obviously now have to think about education and saving for their for their education. So, you know, just in again, going back to ensuring that I'm allocating the right dollars in the right place to optimize what it is that we we have.

Jamila Souffrant 17:09

Hey, journeyers, if you are loving this podcast, then you will love my book, Your journey to financial freedom, a step by step guide to achieving wealth and happiness. I wrote this book for you. This book is for you if you want a clear and enjoyable path to having more money, options and a rich life, this book is for you if you hate your commute and the fact that you need to seek approval or permission from a boss, I hated that when I worked. This book is for you. If you weren't born into wealth, you didn't marry rich or win the lottery, but you still want freedom. This book is for you. If you're at a crossroads, a major decision or event is imminent, maybe a career change, marriage, starting a family, pressures are reaching a tipping point, and the discomfort and the desire for more can no longer be ignored. And this book is for you. If you find yourself zoned out at meetings, looking out the window or daydreaming about the life you truly want. So go pick up your journey to financialfreedom.com so I can show you how to map out how to get from where you are today to where you ultimately want to be, and enjoy the journey while you're on the path, head over to your journey to financialfreedom.com. To see where you can pick the book up. It's available on Amazon, bookshop.org Barnes and Noble, your local bookstore everywhere go to your journey to financialfreedom.com to get the book now on your financial independence journey. Where are you currently? Are you in debt? Are you mostly so my five journey or stages, the cadet stage is paying off consumer debt. That next level is the aviator stage of building up your investments. And then the fourth stage of being a commander is all about having work flexibility. So where are you on that spectrum? And then we can talk about kind of how far you are from the ultimate goal. Okay,

Jackie Kasper 19:01

so I would say that I'm in the commander stage. I've saved for my retirement. We have no consumer debt besides our mortgage, and feel like we have a good foundation, and anything additional that we're doing is only going to better when we're ready to to maybe make a change,

Jamila Souffrant 19:24

right, right? And just like to help people too and with like a timeline as they thinking about their journey. So it sounds like you have achieved Coast fi, where, if you didn't invest anymore, you're on track for standard retirement at like 65 or plus, or whatever age that is. Is that correct? Yes, yes. So for anyone, I have a couple episodes about this, if you search like what coastify is, but I think it's definitely a great measuring stick on this journey, because once you do that, and once you are invested enough that the investments can grow on their own to where you are. I. I can live off those investments at the standard age. Then the work becomes anything additionally you do is, can I, like you said, dial that time back, like, buy more time back to do it earlier. So you're investing aggressively still, or more than the standard amount, or you're looking at, okay, I just need enough money to pay for my actual expenses until I retire, and so I think income then becomes important, obviously, because your income now is either going to be, can we just live off of this and depend on this for the next 20 years, or do I want to work and invest more to just buy back more time? So for you, what do you see that your journey looking like for the next few years as you're approaching or want to approach financial independence?

Jackie Kasper 20:46

Such a fun question, because there are so many options. You know, I enjoy my job right now. I enjoy the company and the people that I'm working with, so I don't see a need for change right now. I think that what I am working toward is the ability to make decisions regardless of a job in the future. So let's say I'm here for the next three years and they no longer need me, or I'm no longer happy. At that point, could I step away without worry, without having to find something else? And I think that we're at that stage, at this point, where we wouldn't be reliant on my salary to invest more or or for our expenses, I feel like we have a really bulletproof plan, and bulletproof plans can can be thrown out the window at any point when life changes, but we understand what maybe our wants are and where we could pare down if we needed to if I was no longer working, and have that understanding between us that, yeah, these are, these are nice to have. These are great things that we're able to do now. But if our situations change, and we do want to accelerate, maybe me not working any longer, this is where we'll need to cut back. So I think that that we're in a in a really good place, my husband is actually potentially thinking about changing jobs, and, you know, having the conversation with him more money isn't the goal. You know, you don't need to make more money. You need a better quality of life. You need to ensure that you're going to be happy. If this is something that's going to be exciting and you want to get involved, then great. But otherwise, you know, we're not dependent. We don't have those golden handcuffs, and that's a great place to be.

Jamila Souffrant 22:56

Yeah, I think you know, ultimately, what I would love is that most people realize they can get to at least this level. It's like the level where you have more options, and maybe you know you do have to work. Someone needs to work, if you're in a household with two people or but you can choose what you do and how often or take breaks. And like you said with your husband, my husband's a teacher, so he has opportunities to earn more in different ways, whether that's summer school or evening school and all these other things that have been brought to him. And I'm like, I just want to make sure you actually want to do that, because I don't want you to think we need it. I mean, there, there are things we'd like to have, you know, we I've been talking about, I feel like this for years on the podcast, like, you know, be nice to have for him especially, be nice to have nicer cars. But I'm like, do you want to work like the extra, you know, shifts and hours? Is it worth it to you? Because I'm fine. Even though I like a nicer car, I'm actually fine with the kind of work I do and the amount of work I'm timing it takes that. I don't want to work extra for it. So if you want to work extra for it, you know? And so kind of having those conversations that trade off for our time and energy, especially with the kids, and I know what you mean with the whole just activities. My kids are like, you know, school ends early, and I'm just like, there's so many things that I'm able to do with them and enrich them with because I have the schedule I have, and that if I were working more, I couldn't do that. So all that you have to consider and think about as you're especially with a partner or kids when you're on this path?

Jackie Kasper 24:25

Yeah, totally, you can do it all. You just may not be present or as calm. And I think that that's one of my goals, is to be present, to be calm, to have that connection, and obviously with less responsibility at a nine to five job, or six to four, whatever it may be. You know, it definitely helps.

Jamila Souffrant 24:48

Yeah, this sounds like you made a lot of great decisions up until when you found financial independence that helped you, like, have that head start. So even before knowing about financial independence in the fire movement. It. And even afterwards, even after finding it that the mind, like the mindset that you have, that you see maybe other people not to judge, but that you see other people like, wow, like you have the income, or you have it seems like you have the capability, but they're not, maybe focused as you like, what are some of the things that helped you?

Jackie Kasper 25:16

So I think one of the things that has helped me get to where I am is being open. So listening to different people, listening to different situations, scenarios, tactics, strategies, and really trying to understand has helped me. So, you know, there have, there are probably a lot of people that don't want to hear it, that don't want to hear what they should be doing. So being open to hearing those things, I think, has allowed me to get to where I'm at. I think having people beside me who have had a similar mindset has also helped extremely if I was only surrounding my people or myself, with people who were buying the extra car, buying the bigger and the better house, which, don't get me wrong, there are plenty of my friends and family who are doing that, but to have people that have a similar mindset to remind me you don't have to do that. There are other options. These are why you're choosing those other options and and this is where we're going to get because of it has been extremely helpful.

Jamila Souffrant 26:27

Yeah, I think those are great points. And to see maybe you're listening as a journey or and thinking about your pathway, is that, like you said, being open, I think being a learner, just like a lifelong learner, and being interested and curious in things is so key. I call it in my book, just like clicking on the hyperlinks, like hearing something and be like, Oh, let me find out more about that. You know, I feel like I'm doing that in a lot of areas in my life. I've always done that where it's just like, that sounds interesting. Let me find out, you know, and then also really important, what you said is like the community, like the people around you, where you can have different like, I have different types of people around me, where it's like, not everyone needs to be on the path, even though I think it's beneficial to be, but it's just like having and knowing that there is someone there that understands it, that you can talk to, is such A important part of the process.

Jackie Kasper 27:20

Yeah, I think also continuing to dedicate time and effort into the journey is important. So I listen to a lot of podcasts, I read a lot I may have to hear something 10 times before it clicks. So this isn't cram it all in, make sure you understand it, know, know everything, and then you're all set. I think that it's important to continue learning, gaining more knowledge, taking in all of the content, so that you can understand how it can help you. Your life changes over time as well. So what situation I was in maybe 10 years ago has definitely changed, so my tactics and strategies have had to change. So I may have had to go back to the drawing board and re Listen, relearn, okay, what should I be doing now that I have two kids? What should I be doing now that I'm in my 40s? You know, just constantly going back and continuing to to be involved and to learn right,

Jamila Souffrant 28:28

that evolution and knowing too Right, like you're also, you know, 40 years old, and I feel like the 20 something year old me, like that journey looks different. You know, someone could look at me and say, oh, like you have it all figured out, like, you know, or your life, you have three kids, you have the husband, you have the house, but it's like it took time to get here. Just experience and age do have something to do with it. So if you are later in life and you don't have those things, maybe you don't even want them, that's fine. But just to be, just to be aware of who you're comparing yourself to, and know that, depending on the season of life you're in, it's going to definitely impact your wants, what you're capable of. And you know, you can evolve and change too, with that, it's not just one thing all the time,

Jackie Kasper 29:10

yeah, I think also just being open to change. So what may have been working for me 510, years ago may have to change, and also not dwelling on some of the mistakes or things decisions that I made in the past. I may have mentioned that my husband and I bought our home maybe seven years ago at this point, and at some point, we refinanced to a 15 year mortgage, and I was really focused on paying off that, that mortgage, only to later realize, oh, now I'm going to be having children. Oh, now I should probably be using that money elsewhere. So it's just being open to change and understanding that you're not going to. Get it perfect. There is no blueprint, and that's okay. All you can do is your best and continue to move forward on the journey.

Jamila Souffrant 30:08

Yes, I love that. It's funny. I was just gonna ask you, as we're like closing out, what advice you would have for someone listening, and I think you gave this great advice just now. But do you have any additional tips or action items or just anything you want to share with other journeyers. Before we sign off,

Jackie Kasper 30:24

sure, I would just reiterate the fact that being on this journey is a mental game. If you can see past the distracting, flashy items and stay the course, you know it will pay in the long run. I don't know where I heard it. It has not come from Me, but I heard it at one point and wrote it down. You know, discipline equals freedom, so be intentional about where you're spending your money, what you're doing with your life and your time, and it will pay off. You know, the last thing that that I would want to do is just coast through life, even if I had all of the money in the world. And things always came easy. You know, be intentional and ensure that you're thinking about the larger picture.

Jamila Souffrant 31:19

Yeah, I love that. And I was just writing down you just had discipline, which reminds me of, like boundaries when it comes to, like, with your money and even friction, right? Like the life we have, if everything was easy, or some people assume that, like the discipline in whatever area, whether it's money, maybe health, whatever that is, actually feels more constrictive, but like, when you have it, life actually becomes, like you said, there's more freedom in it, because you know the boundaries and what you can do and can't do. So yeah, love that, Jackie. Thank you so much for coming on the show again. I know that this will be helpful to a lot of journeyers. So just thanks again. Thank

Jackie Kasper 31:58

you. Yeah, this was so much fun. The first time that I've ever done anything like this, after I filled out the form and was reached out to, I was like, oh, Should I, should I be doing this? Is this something that I you know, but so fun, so exciting to talk about all of these things, because I don't really talk about them with the larger group.

Jamila Souffrant 32:19

Yeah, no, this is amazing. And this is, I'll keep saying this. These are my favorite interviews and conversations to have, and I just think that if you are listening, so partly, what I think is cool about this is that you, because you listen to probably so many other people, and they have inspired you, that now your voice will inspire someone else, and it'd be a part of their journey. And so we definitely have to keep in touch, maybe bring you back in a couple years to do an update on what's happening and where you are. So again, thank you.

Jackie Kasper 32:47

That would be great. Thank you, Jamila. Have a great day.

Jamila Souffrant 32:50

Don't forget you can get the episode show notes for this episode by going to journey, to launch.com or click the description of wherever you're listening to this. And you can still grab your jumpstart guide for free to help you on your journey to financial freedom by going to journey to launch.com/jumpstart

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