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B
No, I don't. No, I don't think I have a favorite. I guess I know the most about fdr.
A
Oh, yeah, well, that's just, you know, you're very into World War II, so that's probably. That's where that comes from. I don't have a favorite either. I think there's good and bad in many of them, and it's nice to have President's Day and to just have a day off in February where the markets are closed. So that's what I'm mostly happy about. Hey, if you are thinking about your money today, and this was the moment where you decided to gather up your tax documents, by the way, for all the organizations who have yet to Send me my 1099s, get on it. I can't believe how late they are. It's ridiculous. They're like, oh, no, it's in the US Postal Service. And give it 14 days. I'm like, well, why don't you FedEx it to me? I'm so angry about this. Drives me crazy every year, but so be it. I don't even want to blame the Postal Service. I feel like it's the organizations themselves. They could do this much more efficiently. Anyway, if you are gathering up your tax documents, get them together and then maybe get in touch with us, because maybe something has come up for you. Maybe something in those documents is a spark for an idea you have or a question you have. If that's your situation, go to jillonmoney.com, click the contact us button, write us a note. And if you'd like to come on the air live, just check the box. Mark will do everything else while you're on the website, check out our subscription service. It's called Jill on Money Live. That is where you have access to four live webinars. Over the course of the next 12 months, you. You will also be entitled to the entire back catalog of those webinars and bonus audio and video content. It's all 45 bucks for the next 12 months. And our upcoming webinar is with the amazing Ed Slott. Thursday, February 26th. We are going to do tax planning. Remember, he's a CPA by training. He is an IRA and Roth IRA expert. He loves talking about the Medicare planning that all freaks you all out. It goes crazy. The Secure Act. All, all of the new tax provisions, everything that you could think of when it comes to taxes and Roths and retirement, Ed's on top of. So why don't you join us? To join us live, you have to be a member of Jill on Money Live if you would like to purchase the webinar after it airs. Can't participate, but just want to check out Ed and what's going on with the community. 15 bucks. That's it. Just for that one webinar. Okay, let's get on with it. Today we are joined by Jennifer in Washington DC. Hi, Jennifer, how are you?
C
Hi, I'm good, How are you?
A
Great. What's up?
C
Well, my question that I wrote in about is whether or not this plan I have for quitting my job to become an artist is ridiculous or not. And I just have a lot of anxiety about money and doing something that is not practical on the surface.
A
Well, but wait a minute. Just because it's not practical on the surface doesn't mean you can't do it. Let's kind of figure it out. So I like the idea of the creator class saying, I want to create. This is a good thing. This is good for society. So let's figure out whether or not you can do this, Jennifer. So first, let's start with the easy stuff. How old are you?
C
45.
A
Are you single, married, partnered?
C
Single.
A
And you have kids?
C
No.
A
This makes the planning a little bit easier. I gotta be honest with you. I mean. Okay, and right now you're fully employed.
C
So I work part time. So I have what used to be a full time job. I got them to give me three days a week. So I work three days a week.
A
And at three days a week, how much are you earning?
C
About 94,000.
A
Okay, and does that 94 cover your needs? Does that kind of give you the basics covered? Is it more than you need?
C
It could. I've calculated that with the lifestyle that I want, I need, I don't need, I want an additional 30, which I, I am able to supply that through my writing. So I could live off of that, of course, but I choose it.
A
So right now. Okay, wait, so part time you got 94. And then for your artistic endeavor, how much are you bringing in right now?
C
That's part of the problem is that it varies dramatically. The lowest it was, was 69,000 and the highest it was, was 311.
A
Whoa. Wow. What a variance. Okay, yeah, but if, let's, let's even make it narrower. If we said right now where you're working three days a week, you got 94 grand. But then it's, you know, I don't know, let's make it more like 70 to 150. Is that fair? Is that more of like a range? That seems very doable. Okay. You're able to do that even while you are working three days a week. Okay. And so the need you have in general is somewhere around 120 or let's say $10,000 a month. Is that what you think you need to live on? For real?
C
I actually looked at my budgeting app. I spent 7,000amonth, and that's the average, including, like, vacations and like. That's great savings and stuff.
A
Amazing. That's great. That's great. Okay, so seven grand a month. Okay, so now let's talk about the money that you have saved already in order to try to make this transition. Five days to three days to maybe zero days. What did you. What have you saved already in. Let's call. Let's start with retirement assets.
C
So for retirement, I have 561 in an investment account.
A
You mean. When you say an investment account, do you mean that's a brokerage account and it's not. Okay, it's a brokerage account, but not an IRA. Not a 401K. Okay.
C
No.
A
So 561 is just a plain old brokerage account. Taxable.
C
Yes.
A
Got it. Next.
C
And then I have 383 in my TSP.
A
Okay.
C
I have $120,000 in a regular IRA.
A
Regular. And the TSP is not a Roth. It's a. It's also a traditional.
C
Well, so my contributions into it are Roth, but matching is actually in. Not in Roth.
A
Okay, so of the 383, what portion is Roth? Would you figure, what, like 30% or smaller? Percent?
C
Maybe like 50%.
A
Oh, okay, that's great. Okay, good. Okay, so I'm back with you. So 561 brokerage. 383 tsp, split between Roth and traditional. A traditional IRA of a $120,000. What else?
C
And then I have my separate brokerage account. That's my quit, my job fund, and that's $157,000.
A
Is that in cash or is that in investments?
C
Stocks, yeah.
A
Okay. Is that it for the investment side? Do you have some other money and checking, savings, CDs, anything like that?
C
I have 30,000 in a high yield savings account.
A
Great. You mentioned a thrift savings plan. Are you entitled to a pension?
C
Yes, I can collect that when I am 60 if I. Yeah, I mean, I'll have 20 years. So when I'm 60, that is 4200amonth. If I quit my job, I would not get the health insurance for life, though.
A
Okay, but if you quit, in other words, if you quit your job tomorrow and wait until you're age 60, then you would receive $4,200 a month. But not health care for life, Right?
C
Yeah.
A
Okay. That's a, that's a great benefit. What about your house? Do you own it? Do you rent? What's going on?
C
Yes, I own. I have a mortgage of about 230 and the house is worth about $793,000.
A
About 793. You know what I'm going to say? I'm going to say 800. I don't care. I can round up. What's the mortgage interest rate on the 230,000?
C
6.75.
A
Oh, you bought this recently?
C
Yeah, I just couldn't. I had a great mortgage rate, but it was 600 square feet and I just had to leave.
A
Okay, but Even with that 6.75% mortgage, you are still looking at a $7,000 a month need, right? That includes the mortgage.
C
Yeah, it goes.
A
Everything. That's great. I mean, that's why I wouldn't go crazy. I know you wish you had the lower, but you. Do you like your space? Is this a space where you could. Okay, great.
C
It was a great decision. Yeah.
A
Okay. See, I'm glad that you say that. Is everybody listening? You can give up a low mortgage interest rate. You ran all the numbers and you can afford it, so that's good. Are there any other assets that you own that we should know about?
C
No, not that I currently own.
A
Okay. Do you have parents that are still alive?
C
Both my parents are alive and to be honest, not in great health.
A
And what about financial health?
C
They're in really good shape financially, actually.
A
Okay. I'm just, I'm really, you know, I, I kind of tease this out more to find out whether you need to help them. Them, you know. And you have siblings?
C
Yeah, I have two.
A
I mean, I don't know how old they are, but if they're not in great health, is that something that we could look in the future and say there's probably going to be some inheritance down the line. We don't know what it is because we don't know how much money they're going to really need to, you know, maintain their care, especially if their health isn't good. But do you. Do you anticipate some inheritance?
C
Yeah, I mean, that's been their long term plan. I also manage their finances. So I am kind of, you know, I want to make sure that they get all of their medical needs covered and stuff and not think about the inheritance stuff. But I am aware of that, like floating around.
A
Okay, all right, well, that's. At least, you know that now. Jennifer, tell me about working this schedule right now. Forgetting. Let's forget about the pipe dream for a minute. How is it for you? Are you feeling like, oh my God, I really am doing like one and a half full time jobs and then three days. Like, how are you managing this?
C
I, I think a three day work week is incredible. And for anyone listening, if you can, your employer will let you do it.
A
Do it.
C
I mean, I can live off $94,000. It's fine. The reason why I'm having the itch is that I think I've, I've done my fail of civil service and I kind of like the job has lost its heart for me. So I was intending to do this job until I retired and I'm like, you know, I don't know about that now. And maybe if I wrote full time I could kind of see how far I could take this other career. But the balance between the two I could do. It's not the balance, it's the actual job itself.
A
The job is sort of like, ugh, I'm sort of over it. Like it was great for some period of time. Not so great. I'm just. You still like, I'm just kind of bummed. Is that kind of like. Yeah. Yeah. Okay, so if, if you were to do this, let's say that you gave your notice, I don't know, you're going to probably like, you sound like a, a good employee. So when would you want to give your notice? Like the end of this year Would. How would you want to handle it?
C
Well, I guess my thought is that I, I couldn't ever give notice until I had enough money in my bank account that I didn't feel scared. And I arbitrarily decided that that number would be a million dollars. And I don't know if that makes sense.
B
Which account? You have a million dollars now.
A
You have a million dollars right now. But let's.
C
A million dollars in the. Quitting my job fund.
A
You mean the 157. What about the, what about the half a million in the brokerage?
C
You don't count that I consider that my retirement money or like my I bought a house money? Like I used some of it for that.
A
Okay.
C
I mean I could be being very arbitrary, and maybe that doesn't make sense.
A
Okay, let's. Let's think about this. I mean, by the way, if you went from three days, could you go to two days? No, I don't think this is the end of the line. I just wanted to make sure. Okay, so part of the planning of the quit my job fund is making sure that you'll be able to actually eventually retire. So if we look at your pension, that's a huge benefit for you, right? You've put your 20 years in, and that is helping build the case for writing full time. It really is. Okay. Now I look at the quit my job fund at 157,000. What I would think is if you want to ramp up and you want to start to see what happens if I write full time, you would probably want to have a couple of years set aside in terms of. I would want, I don't know, two years of expenses set aside. So you're $7,000 a month, right? We have that. That's what you told me you need. And we'd say, okay, well, what would that mean for 24 months? It would be, you know, 106, maybe you say, wait a minute. No, Jill, I want to have three years set aside of expenses. Three years to really give it a go. And so if you have your 36 months. Right. Times your $7,000 a month, that would be 250 grand. So I need a quarter of a million dollars in the quit my job fund. Right. Okay. In some respects, I agree with Mark that, like, you kind of already have it. You could sort of take some of the money that's in that brokerage account, throw it into the quit my job fund and not worry about it. But if you, I mean, having more than three years to figure out whether or not you can make it or not, you know, all that means is you say, I'm giving myself three years to make sure I can support myself. If I can't, I'm gonna have to go get a job and make 100 grand a year doing something. And you may not be able to go back into the civil service, but you may be. But you do. You have a kind of job where you could go get a job in, you know, presuming that, you know, you've got certain skills.
C
I have a good skill set. I will say for people. I know it's been really rough with all the federal workers who've been fired. I could get a job, but part of my resistance is, oh, they're going to want me to work 40 hours a week.
A
Yeah, they are more. Yeah, but that's the risk. Right? Here's the risk that you take. The risk is I have sort of a soulless job right now. But if you want to really try this, it's not. I think that if you're waiting till you have a million dollars in this account, you're going to be working in this job for a long time. You know, it's. I don't know how much you're saving, but I think that out of your 94, if. How much are you contributing to retirement right now in the 94?
C
373 for pay period. And there's 26 pay periods, so that's $10,000.
A
Okay.
C
But then I also send $400 to my investment account a month. And then I like randomly, whenever I have extra money, I put that in my quit my job fund.
A
Okay.
C
So I do save quite a few.
A
You're saving like 20 grand a year basically.
C
Yeah, I guess. And then I.
A
Sounds like it.
C
I've been, I guess I'm pretty good at investing.
A
So it's been whatever. Don't pat yourself on the back, lady. Let's get this, let's get this down. It's a bull market. So yes, you're good at investing and it's a great bull market. But Jennifer, here's the thing. I think you can do this, but I think you have to really weigh the risk. And I can't make this determination. Mark, do you agree with me that if she took a three year period of time, and so let's say during those three years, there's no retirement contribution, there's no saving. Let's just pretend. Stay with me here for a second, Jennifer. There's no saving. There's nothing. You just got what you got. Okay. And then we make sure that you have, you know, $200,000, $250,000 in your quit my job fund. And you look at this as a three year experiment. You give yourself three years. Can I really make this happen? And if you can, then great. You don't look back. But if you can't, then you are taking the risk that you have to go back into the labor market at a good or a not so good time and you say, I got to go back to working. Otherwise you keep working in your soulless job three days a week. You can build your quit my job fund up over time. Maybe wait till you're 50 and see where you stand. But then you're not really, you know, you're. You're still stuck on this job. Now, Mark, do you agree with that analysis that if we have a time horizon where this could be a limited experiment, or do you think she can just do it?
B
I actually do think she can do it because she's kind of doing it already. She's on the low end. She's making 60,000. She's made as much as 300,000. Is there any way I get that you're nervous about doing this, about just kind of going all in? Is there any way you can ramp up the passion project while maintaining those three days a week for, you know, another two years and see how it really, really goes?
A
Let's do it like a. Let's say it's under two years, that you do it this year, and then you do one more year, and then you see what the ramp up looks like. Can you do that or not?
C
Yeah, I mean, that was one of my intents for this year, is to try to write two books, one of which I'm already contracted to the next. Hopefully, I would be getting a new contract and then a new source of funding.
A
Oh, I write a book every five years. This is great. You're doing two in one year. Thanks for trying to feel bad about myself. All right, here's what I'm going to say. I think you can do this. I think that you should try. Let's get this book done. Why don't we do this? Let's make a little pinky swear with each other. Why don't you get this year under your belt, get this book done, get back in touch with us. Let's see where you are. And then from there, let's see if you have the ability to say, at the end of this year, you say, I'm done, and we move forward. And. And maybe you even have another contract by then, and then maybe you'll feel more confident with that contract in hand. Look, you now already have this sense, and everybody listening, you have something that's like an artistic endeavor. But you've already proven the thesis that you can make money doing this, Jennifer. So I want to encourage you to keep doing it, because I think working for anybody is the pits, but that's me. And if you can get comfortable with that and you really can, look at the assets you gather during this period of time, and you have house and you have everything you want. I think you just need a little bit of Runway to get there. And I don't think you need a million dollars in the quit my job fund. I really don't. I think you would want to have three years of your expenses in the quit my job fund. So that's 250. And maybe by the end of this year you'll do that. Or maybe you siphon off some of the money that's in the brokerage account and just put it in the quit my job fund. By the way, once you decide to do that, the quit my job fund, one year of expenses has to be in cash, not invested.
C
Okay, that was. One of my questions is how do people live off investment accounts? They just cash out.
A
Well, you have to cash out. You have to cash out a year in advance at least. At least. Like whatever you're going to need for the next year cannot be at risk, full stop. Okay. And for you, maybe it's going to be more. Maybe you'll feel more comfortable if instead of having, you know, the. Maybe you'll say, I want 18 months in cash. You just don't want there to be any accidents. Because if the market craps out, let's just. Let's pretend it's a year from now and it's 20, 27 and you're done. You've given your notice, the market craps out, and you got 200 grand in that account that it quickly goes to 150. You're going to feel freaked out because it's a lot easier to manage losses when you don't need your money.
C
Yeah.
A
Okay. So I would say at least. I would say most people. I would say one year in cash. For you, maybe I would just do. I would do 18 months. Okay. But I think it's exciting. I can't wait to find out who you really are and what your book is. I will not put this on the air because we don't want to expose Jennifer. But I'm excited and I think you've done it the right way. This is how a side hustle becomes your main hustle. And it's exciting. Yeah. Stay in touch and we'll figure it out. It really does seem like you're on your way.
C
Yeah, I think I just need various people who know more about money than me to tell me this.
A
Who else is there? You got your back. Mark and I. That's two. You need, like, maybe one other person. Be careful. The people who say you're crazy because sometimes they have their own motives, like you're crazy to give up your pension. Which is something that I may say in some instances, but not this moment, because it does seem like you've done a really Good job of expanding how much money you can make doing this.
B
Just remember with a future pension you right now you basically have like two and a half million dollars saved.
A
Yeah. All in. Yeah. Because that pension is not going away. I mean it will be worth less in the future because you know, inflation. But that's still a nice chunk of money coming in.
C
Yeah.
B
Plus Social Security.
A
Right. And Social Security. And you don't spend that much money. But which is a best selling author. She'll be spending more than seven grand a month. Trust me.
B
She's got the.
A
Yeah.
B
You've got the ability to, to try and make this happen.
A
Yeah, I think you should try. I think it's fun. I like it. Dream makers. We're dream makers today. So are you like Jennifer? Are you seeking the permission structure or just the guardrails to figure out whether you can make your side hustle, your main hustle, get in touch with us. Go to jillonmoney.com, click the contact us button which is in the upper right hand corner. Write us a note and if you'd like to join us on the air, just check the box. Mark will do everything else. Hey, if this is some, if this is something you are considering, then maybe you want to buy my book. The Great Money Reset. You know, this is the various ways that you can turn the chaos of this kind of decision into opportunity. And again, erecting the guardrails that you need so that you don't blow through all the money you've accumulated without thinking through what the different possibilities are. So check that out. The Great Money Reset. Okay, you could subscribe to us on the Odyssey app or wherever you find your favorite podcast. Please leave us a rating and review wherever you listen and of course lift someone up. Change your work, change your wealth, change your life. Thank you for listening and we'll talk to you tomorrow. Need contract help for those workload peaks and backlog projects? You're not alone. Robert half found that 67% of companies surveyed said they will increase their use of contract talent. That's why their recruiters leverage their experience and use award winning AI to quickly find the skilled candidates you want. Learn about their specialized talent in finance, accounting, technology, marketing, legal and administrative support at Robert Half. They know talent. Visit roberthalf.com talenttoday Go behind the scenes of one of TV's most watched true crime series with the 48 Hours Postmortem podcast where correspondents and producers take you inside each case Every Monday. Listen to a new episode of 48 Hours and then join me 48 Hours correspondent Ann Marie Green every Tuesday for a new episode of Postmortem. Follow and listen to 48 Hours on the free Odyssey app or wherever you get your podcasts.
Podcast: Jill on Money with Jill Schlesinger
Date: February 16, 2026
Host: Jill Schlesinger, CFP®
Guest: Jennifer from Washington, D.C.
In this episode, Jill Schlesinger takes a listener call from Jennifer, who is contemplating leaving her stable government job to pursue her artistic ambitions full time. Jennifer grapples with financial anxiety, wondering if her plan is feasible or reckless. Jill and her producer, Mark, dissect Jennifer’s financial situation and offer thoughtful, pragmatic advice, discussing how to weigh risk, build a realistic safety net, and recognize when it’s time to take the leap into a new career. The conversation is candid, upbeat, and filled with actionable insights for anyone weighing a similar life transition.
Jennifer on work-life balance:
“I think a three day work week is incredible. And for anyone listening, if you can, your employer will let you do it… Do it.” (13:06)
Jennifer on risk aversion:
“I couldn't ever give notice until I had enough money in my bank account that I didn't feel scared. And I arbitrarily decided that that number would be a million dollars.” (14:20)
Jill, on having enough runway:
“If you're waiting till you have a million dollars in this account, you're going to be working in this job for a long time.” (17:17)
“I would want... three years of expenses set aside... all that means is you say, I'm giving myself three years to make sure I can support myself. If I can't, I'm gonna have to go get a job...” (15:00, 16:55)
Mark, on confidence in Jennifer’s transition:
“I actually do think she can do it because she's kind of doing it already. ... Is there any way you can ramp up the passion project while maintaining those three days a week for, you know, another two years and see how it really, really goes?” (19:37)
Jill, on cash management:
“Once you decide to [leave], the quit my job fund—one year of expenses has to be in cash, not invested.” (21:52)
“You have to cash out a year in advance at least. ... Whatever you're going to need for the next year cannot be at risk, full stop.” (21:58)
Jill’s encouragement:
“This is how a side hustle becomes your main hustle. And it's exciting.” (22:38)
“I think you should try. I think it's fun. I like it. Dream makers. We're dream makers today.” (24:12)
Jill and Mark give Jennifer their blessing to move forward with careful planning, reasonable financial guardrails, and a willingness to treat her new venture as a structured, time-limited experiment. Their advice is practical, warm, and tailored to both Jennifer’s financial savvy and her emotional needs, making this episode a must-listen (or read!) for anyone dreaming of a major career reset.
For more listener calls, expert interviews, and financial advice, visit jillonmoney.com.