How Coaching Helped Jenna Embrace Her Financial Choices

Money Files

This episode is one of my favorites because I get to sit down and talk with one of my clients. Jenna first started her journey working with me as a coach in 2021. She joined my program when she realized her financial management style didn’t align with how she wanted to live her life. Now, two years later, she is a six-figure earner, a new condo owner, and feels empowered to make good choices with her finances.

I chose Jenna for this client spotlight episode because her experiences relate to women who feel stuck in their finances. Before working with me, Jenna worked five jobs, struggled with credit card debt, and had an inherent belief that she was bad with money. As a result, she felt stuck and didn’t know how to regain control of her finances. Since starting her journey, Jenna has shifted her mindset about herself and her money after learning to budget without restriction.

So listen in as Jenna shares what inspired her to choose me as her money coach and how a shift in her financial mindset has positively impacted her life. I love sharing my clients’ wins with you and hope this candid conversation with Jenna inspires you to take control of your money and make the shift toward a healthier financial mindset. 

While listening to this episode, take inspiration from Jenna’s journey…

[00:05:18] I found that working with you is not just about money. It is extremely therapeutic because I think what you unlocked in me and what you made me realize is I always have a choice.

[00:11:21] I’m making close to $15,000 now. If I had not worked with you there would be no change to how I spend money, because my mindset was not in a healthy spot for myself.

Tune in to this episode of Money Files and get inspired by my client’s experience with money coaching and how the decision to work with me shifted her mindset and empowered her to reach her goals.



Transcript for “How Coaching Helped Jenna Embrace Her Financial Choices”

Intro: Hi and welcome to Money Files. I’m Keina Newell from Wealth Over Now. I work every day with professional women and solopreneurs to help them get out of financial overwhelm and shame so they can experience more flexibility and ease with their finances. Are you ready to gain confidence and learn to manage your finances intentionally? Tune in and grab financial tips that will help you master the way you think about and manage your finances.

Keina: Hi and welcome back to another episode of Money Files. So today I have a client interview which are my favorite episodes because I get to talk to clients about the work that we’ve done together. So today I’m with my client Jenna. Jenna actually reached out to me in June of 2021. And so today we are in March of 2023. So it’s been almost two years since you initially reached out to me. But I will go ahead and let you introduce yourself.

Jenna: Ok. My name is Jenna and I am a speech language pathologist at a school. I originally was an elementary education teacher for 7 years and then made the transition to be an SLP in 2017. And I’m also a workout instructor. Have two dogs. I think that’s it.

Keina: She does a lot. That’s what you should understand from that, that she does a lot. So I would love to dive in and I know this but if you want to share like how did you actually find out about me and what I do?

Jenna: So yes I do a lot and I am very much a go-getter. So my school offers a program in special education where you can get your certificate in special education if you don’t already hold it and you get a nice little stipend if you do that program and then stay at the school for two years after. So I was very much like stipend and I’m not going to pay for this so I jumped right on it. And at the end of the program there was like wellness, like stuff to help you as an individual like outside of education and things that you do to help yourself and live a very whole life and one of them was working with you. And so Keina came and did a little like mini seminar on what she does with clients and what kind of happened. It gave us a little taste of what it was like to work with her.

And at that time I wouldn’t say I’ve had money troubles. Like I’ve been very fortunate. I come from you know, middle class family, really have always had everything that I needed or anything that I wanted but it kind of was always categorized by myself and by my family. Like they weren’t trying to be mean or anything, but I just was kind of the one pinned as not being good with money. At the time when I reached out I was experiencing some credit card debt and I just didn’t see a way out of it and her slogan was, or not slogan but her kind of offering was like I’ll help you get out of credit card debt and I’ll help you make choices. Like you don’t have to live this really crazy intense budget but you can have a budget and do the things that you want to do. And that really was the first time I had heard someone in that finance space tell me, okay, you can have a budget and be mindful of your spending but that doesn’t mean get rid of all stuff.

I think also in the past and the way I grew up, it was kind of like well you do this to make this money and then so you can do this, this and this. And I didn’t really see travel in there. I didn’t really see extracurricular things or just kind of ethic money of like hey like let’s just do this because we’re in the moment. I am a very spontaneous. I have joy tattooed on my arm because I’m very do things that make me happy and fill my cup. And so it was kind of the first time I had heard from an individual in that realm that you can be mindful of what you’re doing but also not [04:31 inaudible] that really bring you joy.

Keina: I love that. I actually have a money class. I’m trying to think about when this episode will come out but the money class is going to be on Wednesday the 22nd. March 22nd. So you’re listening to this and I think this is going to air probably the Monday before but if it doesn’t air before that just keep watching my money class series and join me. But I love that you’re talking. The money class is called how to Budget without restriction, is why I’m saying that. So I’m so curious for you just as you’re highlighting like hearing someone and that someone being me talk about, like you can be on a budget and live your life and have joy. Like what has that actually, like what does that look like for you in practice?

Jenna: So I think also that working with you is not just about money, it’s extremely therapeutic. Because I think what you unlocked in me and what you made me realize is I always have a choice. You hear all the time life is full of choices and it’s kind of one of those phrases, slogan that you just hear. But when you really think about it, it’s so true. And I think that’s what you unlocked in me is that I always have a choice and that comes down to my mindset, which is what changed everything. I have the choice to believe that I’m bad with money, whether that has been portrayed on me or that’s what I innately feel or I have the choice to think differently. And I think that was the catalyst and what opened up my mindset to then say, I’m in whatever financial situation I’m in, I want to get here. I’m not stuck. And I think that’s what I was feeling like when I first started working with you is that I felt stuck. I felt like I’m in education, I’m never going to make that million dollar check. And I think I was feeling stuck also transitioning from teaching to speech language pathologist. So I was in North Carolina and then I came to Washington DC for grad school and I’m in Washington DC SLP.

 I made a 40k jump in my salary, student loans and stuff. But that’s a significant jump. But I still was feeling stuck, like here I am making a significant amount more money, [07:01 inaudible] that’s a lot pricier but I still feel like I’m down the same road and I felt like I couldn’t get out of it. And so that power and choice has just illuminated things for me and has given me this sense of freedom that hey you’ve got a choice. You either can save and know, say you want to go on a big trip, I have an option. You can put that on a credit card, you can save for it. That is an option you make and you’re in control of that. Maybe one person thinks one option is better than the other. That can be very subjective and go back and forth with whoever, but you’ve got that choice and I think that was very empowering to me. 

Keina: How did you feel before you felt like you had choices? Like what options did you feel like were available to you?

Jenna: I felt like I didn’t have an option. I just felt like I’m never going to make enough money to do all the things that I want. So I’m just going to, A, I’ll put it on a credit card. B, I will work my off to make sure that money is never the reason that I don’t get to do something, which kind of created your perfect [08:13 inaudible] because when I met Keina, which absolutely this is kind of monumental as well. I think I was working four or five jobs. I was tutoring, I was babysitting, working as a workout instructor, working at a private practice and working at my school. And so while I think it’s somewhat admirable to be like that “hustler person” and I’m not going to anything stop me from doing something that I wanted, I was running myself ragged and when I actually do the things I wanted to do, I was too tired to do them. So I just think that, I felt like I didn’t have an option. I felt like I chose the road of education, I was never going to be wealthy and that was the end of it. And I would just constantly remind myself, well you didn’t go into education for the money, you went into it because of your passion for kids. And that was just kind of like my out.

Keina: And I work with a lot of people that are in this like nonprofit space or they’re educators and you start to like coddle yourself with like a narrative. Like it’s okay because and you give reasonings for why it’s okay. And just like, I’m thinking about how that plays into how you also spend money. Because it’s like, I remember I actually looked at your sheet before we started talking and by sheet I mean like the application that you fill out that’s like hey, tell me about the challenges that you have. And one of yours that you talked about was like impulse buying. And so I’m just thinking about how like when you’re this perfect storm you’re talking about where you’re like okay well money’s not going to be the thing that holds me back and so I’m going to have these like five jobs and I’m going to get whatever I want. And I think that there are a lot of people that are in that mentality and doesn’t even have to look like you having five jobs. It could just look like I’m going to continue earning more so I never have to say no.

And it’s a sneaky little thought that ends up with, people are waiting for more money to make them feel a certain type of way or for more money to mean that they have more in savings but when they’ve never addressed like the mindset like you’re talking about, which is like I always have a choice and I can choose how I want to do this because I’m not saying like, don’t make more money or don’t have five jobs. But it’s like is it actually creating the result and outcome that you desire or is it just actually causing more pain because like you’ve acquired these habits that you don’t even realize that you have established for yourself.

Jenna: Exactly. And I think I’m kind of your perfect example of that because when we first met I was not making six figures and I was making probably like, high 70s.

Keina: You were at 78.

Jenna: Yeah I was at 78 and I’m an open book now too and I’m making close to 115 now. And so the reason I share that is because I think you’re exactly right. I think if I had not worked with you, there would be no change in how I spend money now, even with that great jump because my mindset wasn’t in a healthy spot for myself. And I am realizing now too figure is like making 6 figures I’m like yeah this is great but you still got to watch where every dollar is going. And I even used to think too like you’re maybe an NFL player or another sports or an actress. They have all this money and then all of a sudden they’re broke. And I used to always be like, that would never happen to me if you just give me the million. Like I’ll be fine. And I’m like, nope, that would’ve been my ass on the corner on the street.

But yeah you’re right. You just don’t realize how your habits and your mindset affect your day to day. And I think that’s what’s so powerful. Like when we were meeting, you were like, you’ve been to South block 20 times this week. Like why do you keep going south block? And my initial I think, when we very first started working together or my nerves going into that was like I don’t want anyone to tell me that I can’t get south block when I want to. But what you were trying to show me is like, okay, well that $12, $14 a bowl, you’re getting up to $100 a week and then that’s $400 you’ve spent a month on [12:47 inaudible].

Keina: They’re amazing. I love their bowls.

Jenna: You never at any point said you cannot get that. But it’s like let’s, and also too, when you put the numbers on the paper and you look at it, it’s like oh, like that $400 could have gone to a trip or to paying down credit cards or your student loans. Like yes, you can’t get too up and like what it could been, where it could gone. But it just makes things in your face realistic to know where it’s going. 

Keina: And I think it’s about like, do you want to, do you consciously know you’re spending $400?

Jenna: Exactly. Right.

Keina: And generally that’s my question to anyone that I’m working with, it’s because if you want to spend $400 because south block brings you joy, that’s fine, but do you know that you’re doing it right?

Jenna: Right. And yeah, you’re exactly right. You hit the nail on head. It’s like I didn’t realize how much money I was spending in certain areas. Also too I would get paid and then I’d be like where did it all go? I’m like what but then realizing that also made me reflect too, is like, ok you’re working all these jobs, why are you ordering food to go so much? Because I don’t have time to prep it. Because by the time I get home I’m so exhausted I don’t even have, so it like, is that money really helping you or is it causing you to snowball and let other healthy habits go by the wayside?

Keina: Yeah, I was going to say, I do remember talking to you about the number of jobs you had. And it was like, because of time, we want convenience. But then it’s once again questioning is that what we want? Is this the life that we’re trying to create? What is this in service of? What do you want to, like what’s the ultimate goal? And for those of you listening, when I say ultimate goal, it could literally be like in three months what’s the goal?  In six months from now, what’s the goal? So that we can actually have something to monitor that we’re actually working towards because you’re talking about having those five jobs but you still had credit card debt. So if the goal was to like work the jobs so you wouldn’t have to say no. It was like, but something was off and in your intention and then like the actual reality of it.

Jenna: Right. Exactly. And I think also, just naturally it all snowballed into what are you living for? What do you want in life? Like it comes to this whole bigger picture that your day-to-day habits. I know we’re talking about money here, but whether it’s working out or meditating, whatever it is. It is like, do you do have to take that step back and be like, what do I want each day to look like? What do I want next month to look like? And really, really getting to know yourself and what you want. And I think that’s what’s so powerful too, is like it’s me. Like I’m in my thirties, this is my life. My parents, my sister, my friends, they can give me all the advice in the world of what I should do. But what do I want to do? What do I feel most comfortable doing? What am I willing to step out of my comfort zone to do? Like what do I want my life to look like? And ultimately like I was just plain exhausted. I was tired of not getting enough sleep. I was tired of feeling tired all the time. And I also got to a point where I didn’t feel like I was doing any of those jobs to the best of my ability because I was just trying to skate through to get to the next thing. 

Keina: What changed for you in working together and even your outlook on those jobs? Like did you, I don’t remember you giving up any of the jobs while we were working together, but I guess like just to speak to like where we started versus where you are now.

Jenna: Yeah. So I would say the mindset obviously overall helped me change things. This is the first year that I’m only doing school and the workout job, everything else is gone. And one of the reasons that occurred is from like your encouragement of woman empowerment of my school was redoing the compensation scale. And when I first signed on my seven years teaching experience did not count as experience towards my salary. So you know, woman empowerment, I was emailing HR all the time and I was like, you know what? I really think my teaching experience should count towards this. Like I know it’s teaching and speech pathology but if you’re in a school you know what to expect. You know my ability to connect with teachers and students.

Keina: I’m returning a calm child back to the classroom.

Jenna: Exactly. Like would you rather have an SLP that has never been in the schools or one that has seven years experience in education?

Keina: Yes.

Jenna: And granted they ended up changing kind of the whole formality and steps for everybody, but I also had put myself on this committee. You had to like apply, so I could voice my opinion. So I do believe that I was one of the people to help push it in the right direction. So anyways, all that to say, that’s how I got from 78 to almost 115 now because I was advocating for myself. And again that came from you. Like you need to advocate for yourself. Your time is money. Money is time, like you come very qualified and you need to be compensated for it. So that was a huge blessing that did allow me to cut back on those jobs. Because A, they’re contracting jobs, so we didn’t have to pay taxes in the end. But B also it was the mindset of like, I’m not willing to sacrifice how I feel in my body every day of scrambling from thing to thing.

And I did also feel like it was impacting myself at school because I wasn’t showing up for the kids. I mean I was physically there, I was getting things done. But like now I’m wholeheartedly there for the kids. Like I give them the time they need. If things need extra time, we’ve got it. Like I was trying to do so much before that I felt like I couldn’t give my undivided attention. And overall I just feel like my nervous system is calm. There’s a reason why we go into fight or flight. There’s a reason why we feel certain things when we feel stressed. And I have the ability now to take time to do things that I need in order to ensure that I’m living a healthy lifestyle that I deserve.

Keina: Yeah, I love that. I know you talked about when you came from North Carolina to DC, you got like a 40k jump, which a little part of me laughs because I came from St. Louis to DC and I think I got like a 20k jump, but then my rent went from like $600 to like $1480 a month. And I’m like Oh Huh, interesting. And so like I think the natural inclination is to be like, I’m making so much more. And they’re like, yes, pay $2,000 a month for rent. And so, you’re like wondering where the money is going. I say that for anyone listening because I think one of the things that we kind of miss in taking on a different opportunity when we’re talking city and location, is like also checking cost of living. Does my $38,000 salary match up with what is a $78,000 salary somewhere else? And I know, like I’ve heard different clients, they’re like, but Keina, I got this big pay raise and I should be able to do more. And so you end up in this like mindset of just being I think disappointed because you can’t do them more but your brain hasn’t really considered the numbers because it didn’t have all the facts.

Jenna: Yeah. And I honestly have felt that the past few months and really the past year in terms of wanting to buy a home because I’m like, I’m making a good salary and I still feel like I cannot afford a home. Again, I had to shift my mindset because I didn’t toy with the idea. I’m like, ok, do you want to leave DC, do you want to go to a place where the cost of living is less and accept that lesser salary. Like I had to weigh a lot of different things. But again, when I would get frazzled or go down like a rabbit hole of like, this is crazy. And feeling down about myself, I would always come back to, you have a choice. Like that was kind of my mantra. Like you have a choice and if you want to move you can. You also need to know though, that salary might go down, cost of living might go down but there are tradeoffs, there are a thousand different tradeoffs. So ultimately what I’ve decided, which I’m very excited about, I did buy a condo a couple weeks ago.

Keina: I know I’m so excited for you.

Jenna: Very excited. So I went with, I’m going to have a postage stamp on a place.

Keina: A postage stamp. What you’re telling me is you got a studio?

Jenna: Basically a studio. The bedroom still has a door on it. So technically one bedroom,

Keina: They’re like nope, it counts.

Jenna: But I made that decision, I made that decision that I’m going to invest in something that’s small. Like initially when I started this home search, I was like I want to be in an old town. I need to have a yard and 2 dogs and now we’re in a condo inside of 550 square feet. But again, what I kept going back to is you’re not stuck. This is your choice. If you do not want to make this choice, you do not have to. You can keep running, you can keep doing all these. But for me personally, my biggest is that I wanted to stop renting. I wanted to invest in something. So ultimately like the return on it, it weighed out the negative of being in a smaller place. But again, I just kept going back to you’re not stuck. You have choices and one choice is not wrong, not right. Because even, my dad is so funny. He’s like I just want to let you know that I paid $400K and I have a five bedroom house, three bathrooms and like an acre of land and you just told me what you paid for yours and you have 550 square feet.

Keina: What did you pay for yours?

Jenna: I paid $330.

Keina: Ok, that’s good.

Jenna: With, now woman empowerment, once again I negotiated the parking spot in there.

Keina: Oh that right there. Listen guys that don’t live in DC she basically just paid $2.

Jenna: Yeah, exactly because when I told my mom too, she was like, well yeah, just so you know, your grandfather in Boston sold his parking spot for 100k. Like, you know, back in the day. And don’t get me wrong, it’s going to be a stretch. Like that mortgage is a little bit higher than my rent. I’m going to have, and what I did though. I had 3 plans. So I put that number in my budget and looked to see where adjustments need to occur in order for this to happen. I am very excited and proud that I was able to do that. But again, I had to, I mean this only happened two weeks ago and I literally up until the moment was like, this is your choice. You do not have to do this. But you have the option and it’s in your power of what you want to do.

Keina: And you get to win it. If you’re like, you know what, this was the worst decision I’ve ever made. And somebody will be like, thank you for your shoebox. 

Jenna: Exactly. Exactly. And now you know, listeners don’t judge me. The dogs get plenty of exercises, they get everything they’ve needed. But even with them too, with the dogs, in some of our sessions you’re like wow, you’ve got two, that really you know, eats up some stuff.

Keina: Oh everybody I work with, they these pets, I’m like y’all, these pets. I don’t want to tell you to get rid of Fido but he’s expensive.

Jenna: Oh yeah. Try with severe anxiety, because that one you have to go to the behavior list for a job. 

Keina: The other thing. We had pets when we were little, they didn’t have like additional needs and now everybody’s pet has like additional needs. They need like this special food that’s raw because otherwise I’m like you got them from the pound?

Jenna: Yeah, exactly. And both mine are rescues then that’s yeah, just what happens sometimes. But again, I remember even I was having like a down moment and I was on the phone with my sister and she’s really great too about like reminding me that you’ve got choices. And I did, I was like dogs are so much funny because at the time I was having alot of behavioral issues with my youngest dog that has a lot of anxiety and I just felt stuck. Like I was like how am I going to support him? Like training costs so much money and all this stuff. And she was like, why do you have your dogs? I was like because I love them, they bring so much joy? Like they comfort me. She was like and that’s what you need to keep going back and she was like and that’s the choice you made. You choose not to have your dogs anymore, that’s an option. But these are choices that you’ve made and you made it because they make you happy. And while that comes with responsibility and cost like again, nobody handed me two dogs and said you have to take care of these. That was the decision I made. Now was it the smartest decision to get a second dog? Hell no but here I’m.

Keina: And for all my dog lovers, somebody was asking me because on Instagram today, I asked them what questions do you want me to ask someone that I’m interviewing? And so I told them a little bit about your profile but what type of loan did you go with for your apartment or your condo?

Jenna: I went with a conventional loan and I did so it’s going to be in a up and coming area so the reason I was able to do it is because is because it got a 10k grant. So that is why I’m able to do it because it’s in an area that they’re trying to get more and more people in. It’s a brand new construction as well. So if you went with their preferred lender you got that grant.

Keina: $10,000 like down payment?

Jenna: Yep. Towards down payment and closing costs.

Keina: Did you bring money for down payment too?

Jenna: I did. So I’m bringing about 10 grand, 10 12 grand and then they’re bringing 10.

Keina: Do you know if your loan has PMI?

Jenna: It does not.

Keina: Okay. And for anyone listening to this, because someone asked that question today, I was like Oh I don’t think I’ve ever talked about me buying my house on the podcast. But when I bought my house I did a conventional loan as well. But my lender that was like for the town homes that I live in, they had a conventional loan with 5% down with like no PMI. And I had never heard of that like loan tool if you will. Because generally speaking, if you don’t put in 20% then you’re going to have to deal with PMI, which just makes your mortgage higher because they’re waiting for that 20% equity in your home. So I just wanted to put like a little asterisk there for anyone who’s like, what is she talking about? But also like it’s one of those things where when we have money conversations, like money conversations don’t have to be about how much debt you’re in, saving money or like how much do you make.

It could be like can you tell me about your home buying experience And just like being able to learn like someone’s going to learn from you that there’s an option to potentially buy in specific areas of DC where you can get like a $10,000 grant and it goes towards your down payment or your closing costs and those closing costs they’re expensive, the title and deeds and you can even shop around, I’ll say this too, you can shop around for the title company, which I didn’t know. I mean I knew at some point in time before I went to the table but I just thought I had to go with the person that was given to me. But yeah, everything’s negotiable apparently.

Jenna: Yeah, everything’s negotiable. And I’ll say too, if you’re interested in buying a home, again I’m by no means an expert but I did get like quotes I guess you would say or numbers from three separate lenders. That was the other thing too, it’s like you would’ve told me 10 grand down the road, I’d be like I don’t want to go with anyone else. Just give me that. And I was like no. Like ok this is appealing. But if they give you 10k like is there a caveat? Does that mean, the interest rate going to go up? So I looked at multiple different ones before I ultimately decided on this one.

Keina: Yeah. I love that you ask additional questions. Because like that is a good curious question to have is like, well why would they be giving me this incentive and what may not be like in black and white that I can see and at least you have two other offers to also look at and be like, okay well this is actually a good deal or it’s not a good deal. Or can you actually match their deal and still give me the 10 grand. 

Jenna: Exactly. And I think the other thing to remember too, regardless of what you’re going through or looking into purchasing or whatever it may be, is to feel comfortable asking those questions. Granted my real estate agents are phenomenal and one I went to college so I feel very comfortable. It’s also two women so I just feel more comfortable asking them a bunch of questions but don’t ever feel like you can’t. And I felt more empowered for a purchase like this because I’m like this isn’t 20 bucks. This is my savings. But yeah, just ask a ton of questions. If you don’t understand something, make sure they explain it to you. Just really advocating for yourself because if you’re not going to do it, nobody else is going to do it.

Keina: Very true. And don’t feel bad for asking questions. Going through a new experience. I think that’s the other thing is like you could sometimes feel scared because you’re doing something new and unfamiliar. But it’s like all of the reasons in the world to ask questions. And I love the point that you make about talking to people that you feel comfortable with. Like, when I bought my house, I had one realtor that I had ended up firing because they didn’t communicate well. And the same thing happened. I want to say it took me, I think I went through three realtors, but it was like I want to make sure that I’m getting the information that I need. Because ultimately you are paying them like you’re not paying them directly but they get a percentage of the home sale. So make sure that they’re doing their job and that you feel supported. 

Jenna: And I will say even with my realtors who I adore, I’ll say in the beginning I felt almost like they were kind of pressuring me because I would go to an open house and be like, I really liked it. They’re like ok, what do you want to offer? And I’m like, no, no. Like I’m just looking. I don’t want to offer anything. It’s kind of that happy medium if you want them on top of it. You want them to be really communicative. But then also there was a few times I wasn’t stern with them but I’m a people pleaser so I didn’t want to hurt their feelings. And I was like Jenna, you got to cut that. You’re not hurting their feelings. In fact you’re probably making their job easier if you tell them exactly what you want. So if they would say like, do you want to make an offer? I would just say, nope, I don’t want to make an offer. I don’t want to do anything else. I’m just letting you know this is what I liked so you can have a better understanding of what I’m looking for.

Keina: I love that. Yes, please advocate for yourself. And also I’m looking into investing in real estate and so I’ve been listening to like podcasts on it and just doing my additional research. And so sometimes I think to fill in gaps it’s like well where else can I get information? Because you could have somebody in front of you helping you but then also continuing to inform yourself. Especially when you’re like in the dark, type in first time home buyer in your Apple podcast or Spotify and you could let something like that guide you in regards to anything that you’re doing I think financially or even fitness-wise or any of those things. But like just giving your brain some additional information to digest and to really think about. I want to ask you before we wrap up since we were working to what, almost two years ago now. Like what are you most proud of in terms of like what you accomplished?

Jenna: I would say the thing I’m most proud of is being aware of my mindset, being aware of when I’m talking down to myself or when I’m encouraging myself, making sure I do write down my wins. Those are important. And I think those help catapult you forward. I think a lot of times we’re very much overcome and overwhelmed by the overarching goal instead of your small wins. Because in anything that you do, it’s those small wins that’s going to get you to that big win. And I think it’s a lot of these small wins that I’ve had that have allowed me to come to this big win purchasing a home. And yeah, I think I’m most proud being aware of my mindset and always going back to the mantra I have choices.

Keina: I love that. What are three wins that you’ve written down that you’re like really excited about?

Jenna: I think maybe specific for like in January. I was going to Aruba at the beginning of January. I was going to Costa Rica in February and I had to pay for dog training in February. So it’s like three big like financial things and instead of just either A freaking out or B, giving myself a pity story about how I wish I had more money, I was like write it down so you can plan. And so I did and I planned and was able to do all of those things. Like, don’t be about this but I sold my Peloton, not that I don’t like it, it’s just now that workout classes are back in session I’m not teaching more in person so I just wasn’t having the time to write it. So I sold that and I did little things to ensure that I could cover those costs. And that was a small win for me because literally all it took was writing down in the budget what’s coming and then planning for it. 

Keina: It’s  like you had tools or something. 

Jenna: Exactly. I don’t know where I got those tools from. Yeah. That was just a win. And it just helped me realize like once again you can do it. I think another thing that I’m proud of is that money and a budget is always fluctuating. It’s a living document. I think my biggest hold up with budgets in the past was, okay, well I was doing great and then I got a flat tire. But then you work with the numbers. You’re like, okay well you’re not going to get south block this week because that’s going to go towards, you’re getting a new tire, like, you see the numbers and you’re able to tweak them. And I’m proud about not only being able to do it but also having the confidence in myself that I can tweak those things to make it.

Keina: I love it. I also remember when we were working together Jenna, I feel like, just to go back to your family, which you mentioned earlier because they like told you basically that you were bad with money. But I can’t remember exactly when it was that we were working together. But your mom realizing for you that something had changed in how you managed your finances.

Jenna: And I think, they never like sat me down or like you are bad at money. It was also I will say part of my own narrative too, like my [38:02 inaudible] is a very successful business woman and so I would often compare like our finances to each other. So it’s kind of the narrative I told myself. But I think what my mom has seen in me is that I have been invested in myself and as a return I’m growing and becoming more of the person I want to be. I’ve always been and I’m seeing more joy and happiness in my life. I’ll not lie to you, when I told her I was working with you and told her the cost, she was like, you’ve got to be kidding me, are you joking? And now she’s always like, can you send me that spreadsheet that woman gave you? Because she just sees that I just, again, it does not mean that I don’t ever have down days or I don’t run into financial situations where I need to make a plan or I need to make a better decision. Like those things still occur but I feel like I’m in the driver’s seat, before I just felt like life was coming at me and I didn’t know what to do. Whether we like to believe it or not, money is a huge driving force in how we show every day. Because it’s just our world. It’s how we get stuff. How we do things. 

Keina: I’m curious, did you tell your mom you were investing in a coach before or after you paid me?

Jenna: After. So I did. She was like, I do not think you should do that. And I was like, well it’s already happened. I don’t know what you want me to say. And I’ll say too, like I’ve had so much support from my family. Like when I was in grad school, they helped support me financially. Like I have been blessed with that. And I think also, but that’s where a lot of guilt came from too. It like, I have people supporting me and I still can’t get it right. But yeah, I think she just overall sees this kind of like, not caring, but like I know what I’m doing and also I’ll ask for help if I need it like advice and stuff like that. But overall I’m just not freaking out about it.

Keina: Yeah. What would you say to someone because I’m a defaulter in terms of, usually I go to my mom when I’m like, mom, I’m thinking about this or sometimes I go to her like, you went to your mother. And I’m like, well you don’t really get to chime in on this. I just need you to listen. Like when I quit my job, I was like, I’m just telling you I quit my job. It’s not open for a discussion. I’m just letting know. Just in case. I mean you don’t even see my W2, but just in case you were looking for it. But what advice would you give to someone who maybe is on the fence about like, working with me, but it’s similar to us in the sense of like, but yeah, let me check with my mom or whoever their person is that like, this is a good investment for me. If they need to make that decision for themselves, like what would they need to know? What would they need to tell themselves to be able to move forward?

Jenna: I would go back to you have choices, you’re the person that gets to decide. And again, this is corny, but I’m corny, like it’s priceless. I have been given the knowledge and tools that are going to serve me for the rest of my life. And have allowed me to have small wins, big wins, everything in the middle. And it’s changed my mindset. And again, not just about finances, about everything. Romantic relationships, friendships. Like you have the choice and it’s scary. I put the charge for working with you on a credit card. You’re like we’ll help get that off. I’m like I hope so. I hope you’re for real because this is scary. But it goes back to the other phrases too of like, things that scare you the most you should do them because they’re going to propel you forward. And I always love when I see things that you post about how much you invest in yourself and really you can never go wrong if you’re investing in yourself because that knowledge, those tools, no one can ever take that away from you.

And yeah, I mean of course you don’t want to put yourself in like some crazy financial situation, but at the same time, who is going to have that money just laying around. Unless you are a billionaire or something, like who does just have that money? It’s an investment in yourself. It’s an investment in your future, it’s an investment in your mindset and the ability to free your mind, give yourself permission to do the things you want to do in life. 

Keina: I love it. I mean I always tell my people too, I’m like, you can’t afford not to invest in yourself. Because what I do know to be true is that you’re going to end up spending the money in some other way. Like even, we were talking about South Block in our conversation. So say that you are spending $400 a month on South Block. And it’s not to say that like that South block purchase all goes away, but like when you’re aware of that, it’s like, dang, I get to decide if I want to put that money in my pocket, if I want to start saving money. Like you are going to be aware of so many other choices. And I do tell my clients like, yeah, you could pay for it if you want to on a credit card and we’ll figure out the plan to pay it off.

But one, I believe in you that much. And two, I know this is like the singular best investment that you can make to support where you desire to be financially. And it’s about the money that’s in front of you, but it’s also about every other dollar you’re going to make after that. As you were just talking about, like, I planned for my house and buying this condo and what it looked like. And I felt really confident in that. And like I know for you what you’re making right now isn’t the least amount of money you’re going to ever make. And so now you get to continue to use that skill and every time you share on Instagram with me, you’re like, Keina I did this. Like when you moved to Old Town, and you bought a car too, right?

Jenna: Yeah in the past two years I bought a car and a condo.

Keina: And it was like. I remember we were working together. You were like, I think I want a car. I’m going to need a car. I’m moving. And like, you figured out all of these things in a way that feels really good to you. So I’m excited.

Jenna: Yeah. I’m very excited and I am grateful for you, I mean I probably think about you everyday because I’m always like, where’s that dollar going? But again in a very positive like empowering way of like, again, this is your choice. Do you want to do this or do you not? And feeling confident in those decisions. Even if you’re out one night, you give everyone around shots. It’s like, ok, well I don’t feel bad cause that was my choice. 

Keina: Yeah. And like you were talking earlier about your budget being flexible, like, it’s not to the point where you’re like, well. No, you just like switched some other things around. Whatever that is. But it’s all about having that knowledge that it’s happening and the awareness that it’s happening. And the confidence that you can adjust. Because like there are things like that, opportunities that are going to come up and you want to know that I have the money available and if you are budgeting, like you’re not going to have to live a restricted life because you are going to know where your money is.

Jenna: Yeah. And I think also being comfortable with the fact that whatever decision you make is the one you thought was most appropriate in that. Because maybe 10 years down the road, I’m like, buying that condo was not smart, but in this very moment it was smart. It was the right decision for me. I remember I had a friend that I have a bunch of little tattoos and one of the ones he was looking at and I was like, oh, I don’t really love that one. He was like, but did you love it when you got it? And I was like, yeah, I did. He’s like, that’s all that matters. It’s like in whatever moment, whatever phase you’re in right now, whatever decision you make, you’re making the best decision that you can with the information that you have, the knowledge that you have and whatever emotional state you’re in, you’re making best decision in that moment and being comfortable and confident in that and knowing that probably would change in 10 years or in five years.

Keina: Yeah. I love that. And I just love hearing about like, just knowing all of the shifts because Yeah, I know you’re out there in the world making good decisions, whatever that may be. Like I’m seeing you in Costa Rica, I’m like, don’t you guys have school? But it’s not even about whether or not you have school.

Jenna: Yep. That’s always on the top of my list. Reset myself and then came back.

Keina: Thank you Jenna so much for joining me and I appreciate it. I know that someone, you probably, whoever’s listening to this podcast has taken some notes and some tips and I just love you talking about like, you have a choice, which I think is a great one-liner for anybody to use, especially when they’re thinking about their finances and finances being something that you can feel so much shame around. So I appreciate your voice and your input. 

Jenna: Thanks.

Outro: Thank you so much for listening to Money Files. If you’re ready to take the next step to reach your financial goals, head to and let’s get started.

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