Should I Pursue a Great Money Reset?

Summary

Jill on Money with Jill Schlesinger

Episode: Should I Pursue a Great Money Reset?
Date: February 5, 2026
Host: Jill Schlesinger, CFP®
Guest: “West Coast Rob” (Listener caller)
Producer/Co-host: Mark

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Episode Overview

In this episode, Jill talks with “West Coast Rob,” a previous caller contemplating a major career and life change after experiencing burnout and being passed over for a promotion. Rob seeks advice on whether he’s financially secure enough to take a “great money reset”—a significant pause or pivot in his professional life. Jill and Mark walk through his financial specifics, evaluate his flexibility, and discuss the psychological, practical, and tactical aspects of making a big work-life move.

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Key Discussion Points & Insights

1. Rob’s Background and Situation ([03:05])

• Rob previously called the show for advice about pursuing a promotion. He decided to go after the role but didn’t get it—a new, external hire filled the position.
• Already feeling burned out, Rob now faces the need to support the new hire and is feeling worse, not better, even after a holiday break.
• He is considering a “great money reset” in March (after his bonus), and wants to know if he’s financially ready.

2. Rob’s Financial Facts ([04:31] – [07:56])

• Age: 41, turning 42 in the summer
• Status: Single, no kids, lives on the West Coast
• Income: ~$250,000 per year (salary, bonus, dividends)
• 401(k): $777,000 ($100k already in Roth, additional after-tax funds available for conversion)
• IRA (old employer): $494,000
• Roth IRA: $177,000
• Brokerage account: $680,000 (invested via index funds, self-managed)
• HSA: $94,000
• Cash (saved in anticipation): $140,000 (+$5,000 bank account for monthly expenses)
• Pension (old, not yet annuitized): $48,000 (would pay $1,800/month at age 70)
• Social Security (estimate at age 70): $32,000-37,000/year
• Primary Residence: Home valued at ~$515,000, no mortgage
• Annual Spending: ~$60,000 (half fixed, half discretionary—not including health care)

Memorable Jill Reaction
"[On net worth] Oh, poor you. Too much money." (Jill, [06:04])

3. Evaluating the Reset – Can Rob Afford It? ([08:35] – [14:21])

• Jill and Mark probe what kind of income Rob would need if he were to pivot to a less lucrative but happier position.
• Rob thinks that a step-down job would mean at least a $50k cut. Jill encourages him to cast the net even wider:
  • "I want to cover your spend and then a little bit more... You never have to make $250,000 again if you don’t want to." (Jill, [13:35])
• Rob estimates he could secure a $120k–$150k job within 3–6 months if necessary.
• Jill and Mark agree financially, Rob is in an enviable and flexible position. He could even take a sabbatical without major money anxiety.

Notable Quote
"The can is not even a question. Of course you can. You’ve socked away so much money that it has given you the opportunity to make a transition." (Jill, [11:35])

4. Psychological & Practical Guidance ([10:06] – [17:17])

• Jill advises not to make any rash decisions until Rob gets to know the new boss; there’s a chance things could improve, or at least that Rob's support will be valued.
• Encourages Rob to test the job market, start looking for opportunities, and get comfortable with flexibility.
• Jill and Mark reinforce that Rob’s diligent savings and low spending mean he can afford a reset with little risk.

Advice Highlight
"You don’t have to make proclamations… For right now, I think you can walk away. You can feel good about that. You’ve put yourself in this great position." (Jill, [14:21])

• Mark points out Rob could retire early if he wanted:
  • "If early retirement in your 50s is part of the plan, you’re going to have more than $4 million. You spend no money, you’re going to have $1,800 a month in a pension, your Social Security… I don’t see any problem here." (Mark, [17:01])

5. Tactical Financial Suggestions for a Transition ([12:26], [15:12])

• Jill recommends consolidating the old IRA into the current 401(k) for simplicity and ease of Roth conversions if/when Rob leaves the company.
• Suggests Rob consider being less aggressive in his investment allocation (currently around 90% stocks), and to increase cash reserves to 10%.
• Points out that a lower-income year could be an opportune time to realize capital gains or perform Roth conversions at lower tax rates.

Tactical Tip
"If you are going to truly be in a lower tax bracket, just freeing up some money and maybe that cash position, I would like it to be 10%, not 5%." (Jill, [16:49])

6. Overarching Messages

• Don’t Let Yourself Be Pressured
  "Don't be bullied or cajoled into doing something that you actually don't think is right for you… You know yourself better." (Jill, [17:17])
• Trust Yourself
  Rob is urged to prioritize his well-being and to trust his judgment, especially after recognizing his burnout much earlier.

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Notable Quotes & Memorable Moments

• "[On not getting the promotion] So now I get to support what they were going to have me do or have me do. So in addition to the burnout, now I've got another person, and I've been kind of rejected from that." (Rob, [03:37])
• "You have no pressure. You never have to make $250,000 again if you don’t want to." (Jill, [13:35])
• "You totally can do this." (Jill, [13:35])
• "If early retirement in your 50s is part of the plan, you're going to have more than $4 million..." (Mark, [17:01])
• "Just because a promotion is dangled out in front of you doesn't mean it's the right move for you. Right?" (Jill, [17:46])
• "[On the pressure to always achieve] You get wrapped up in that. But yeah, I know, that's great advice." (Rob, [17:52])

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Important Timestamps

• [03:05] Rob shares his story: burnout and missed promotion
• [04:31]–[07:56] Rob lays out detailed finances
• [08:35] Discussion on annual spending and reset feasibility
• [10:06] Jill explores psychological and practical options
• [12:26] Advice on consolidating retirement accounts
• [13:25] Mark affirms Rob’s strong position, potential for sabbatical/early retirement
• [14:21] Jill’s summary: “You can walk away, feel good… you’ve put yourself in this great position”
• [15:12] Asset allocation, cash reserves, and Roth conversion strategy
• [16:49] Jill: Increase cash to 10%
• [17:17] Final wisdom: don’t be pressured; trust yourself

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Summary Takeaways

• Financially prepared? Absolutely—Rob can easily afford a job reset or even an extended hiatus, thanks to smart savings, low spending, no debt, and significant investments.
• What next? Get to know the new boss first, then test the job market; don’t rush or panic.
• Practical steps: Consolidate accounts, tune asset allocation for flexibility, and build cash reserves.
• Emotional wisdom: Don’t let social or workplace pressure drive your decisions—trust your gut and recognize your limits.
• If you’re feeling like Rob: Use this as a blueprint for a smart, risk-aware job or life reset.

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For listeners facing similar crossroads, Jill’s essential message shines through: Prioritize your well-being, know your numbers, and remember—money well managed is the foundation for living on your terms.

Transcript

[A]

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[B]

Hey, Jill, thanks for having me back. So I actually emailed you guys a question back in October, and the title was should I go for the Promotion? And you guys gave great advice. I had kind of been saying that I was burnt out, really didn't, you know, really wasn't necessarily interested in the job, but I was being pressured by management to go for it, and I didn't listen to you guys. And they pushed and pushed, and I actually did end up applying for it, interviewing, going through the whole process, then come to find out they picked someone else from outside the organization. And so now I get to support what they were going to have us do or have me do. And I get to support someone else who ended up landing the job. So in addition to the burnout, now I've got another person, and I've been kind of rejected from that. So that was right before Christmas. And so I took time off between Christmas and New Year's. It was like 12 days. And I thought, you know, usually that's good enough for a recharge. Now here I am into January, into February and not getting better. As a matter of fact, you know, I kind of actually feel worse from when I emailed you guys. So really just want some help figuring out, you know, I'm really considering a, you know, great money reset or to do something different in March, which is when my last bonus pays. And so just looking for yours and maybe Mark's advice, too. Am I ready? And, you know, if I can share some quick numbers, maybe we can go over it.

[A]

Yeah, let's do it. So first of all, Rob, remind us, how old are you?

[B]

I am 41. I will be 42 this summer.

[A]

Okay. And are you single, married? What's going on? Partnered.

[B]

I am single and I live on the west coast of the United States.

[A]

Okay. And no kids?

[B]

No kids? Nope.

[A]

Okay. And how much are you currently earning?

[B]

About 250k. That includes, you know, the base salary and then some bonuses. And I have some brokerage money that comes in. You know, you got dividends and all that, so about 250k.

[A]

Okay. And are you currently using the company's retirement plan?

[B]

I am, yeah. We have a 401k with a 10% match.

[A]

A 10% match. Dollar for dollar, up to 10%.

[B]

Something. Yeah, something like. I think you have to put 8% in and they'll give you 10 and are you maxing? Oh, yeah, yeah, yeah.

[A]

Okay.

[B]

I'm one of those people that do those backdoor, mega, backdoor type.

[A]

Oh, okay. So let's talk a little bit about the value of the account right now. So you've got a 401k. Part of it is traditional, and part of it is Roth. Give us the traditional balance.

[B]

So I've been doing rollovers. So some of it hasn't been rolled over into the Roth yet. But currently the 401k is worth about 777,000.

[A]

Okay.

[B]

And what I would say about maybe a hundred of thousand of it has already been rolled into a Roth. And another is in after tax that I could roll over at any time. It's just the market just keeps going up and I don't want to pay the tax bill quite yet.

[A]

Oh, poor you. Too much money. Okay, so $677,000. Traditional 100 is Roth.

[B]

Yeah, roughly.

[A]

Okay, got it. What about outside of the retirement account?

[B]

Yeah, So I have an IRA from my old company that has 494,000 in it. And then I have a Roth IRA when I was able to contribute that to that. That's with 177K.

[A]

Okay. And brokerage?

[B]

I do. I have a brokerage of 680.

[A]

Great. And you're managing this all yourself, right?

[B]

Yeah, I just do index funds. I'm a Vanguard guy.

[A]

Yeah. I mean, sometimes simple is better. Okay, what about your housing? Do you own a home on the west coast or not?

[B]

I have some other accounts, too.

[A]

Oh, let's go.

[B]

Yeah. So I have a HSA.

[A]

Okay, good.

[B]

And that's got 94,000 in it. I have cash that I've been saving for this potential change because I know it's kind of been coming about 140k. And then I have an old pension that the current value of it is 48,000. I went in preparation for this call, I went and looked to kind of see what it would be worth when I annuitized it. And at age 70 would be worth about 1800 bucks. I did pull Social Security as well. I know I'm young, but it says 32,000. 37 at age 70.

[A]

And you have like a bank account in addition to the 140 in cash right now?

[B]

Yeah, but it's got like five grand in it. That's just like monthly expense?

[A]

Yep, Yep. All right, so let's talk about what are you doing in terms of housing. Are you renting or do you own.

[B]

Yeah, I own a house. It's worth about 5, 15 or so.

[A]

And is there a mortgage that's outstanding?

[B]

No.

[A]

Oh my goodness. Mark, stop giggling.

[C]

And he must spend no money, I'm guessing.

[A]

That's what I'm thinking. No rental property? No. Anything like that?

[B]

No, just, just. I invest in just financial assets. Keep it easy.

[A]

Yeah, exactly. Okay. Anyone you have to take care of, Parent, sibling, anyone like that?

[B]

No, Very fortunate. I've got some brothers and my parents and they've. They're all working or retired with pensions. So everybody's good.

[A]

Great. All right, now tell us how little you spend even though you live on the west coast.

[B]

I spend about, about 60k a year. I would say my fixed expenses are about 30. That does not include healthcare, though. And then discretionary is about another 30k. That counts. Like, you know, buy a new car every now and then, put a roof on the house renovation.

[A]

So it is fair to say that if you just called it quits at this job and we just needed to, you know, you could, we could assume that you're gonna work again, like you're gonna reset to something where you're happier. What should we assume you can earn?

[B]

Yeah, see that's where like I don't have any like side hustles or like extra skills that I've had that are like money making. So basically I just work a kind of a 9 to 5 job. And so pulling the plug on it kind of makes me nervous because I think that probably if I went and found another job similar to this, I'd probably be taking a $50,000, if not more pay cut.

[A]

Okay. But that's okay. Why don't we even say it's beyond that? Let's say to do your great money reset, let's put the bar much lower. All I need you to do, truly, is you go find a job, eventually you relax and your base and bonus doesn't have to be 200, it could be 150. You think you can do that?

[B]

Yeah, I mean, the thing that just has always held me up from that is just because you take less money somewhere else doesn't mean you're not gonna just get yourself in another stressful situation.

[A]

Absolutely. This is how always counsel people against divorce. I'm just kidding. Says the girl has been divorced. So I just, I mean, yes, there is no guarantee, but you have a. Like, have you met the New person who stole. I mean, got the job that you never wanted in the first place.

[B]

No, I have not. I have not met him yet. He's.

[A]

Maybe you like him.

[B]

Yeah, maybe.

[A]

Oh, my gosh.

[B]

I mean, part of the issue though, too is just. It's the new director that's coming in and just leaning on. On me and changing things around. So, yeah, maybe. Maybe I would like that person. I don't know.

[A]

Yeah, I mean, listen, it's certainly. I wouldn't do anything until you met the person, but to start looking, I would. Yeah, I'd start looking. I would absolutely start looking. Because who knows, maybe you get somebody who's like, smart and says, hey, West Coast Rob, I don't know jack about what I'm about to do. I know you got passed over for this, so why don't you stick around, help me out and let's see how it goes. I mean, no one does that because, like, then that would admit that they don't really know what they're doing yet, but it would actually go a long way. But let's just say, let's not make any. Let's not judge yet. But, you know, if you had to go even stay in your industry, do you think you could find something? Even if we don't know what the next devil is going to be? Right? The devil, you know, and all that. Do you think you could find a job at 150 all in?

[B]

Yeah, I probably. Yes, I think I could. I don't think that would be too difficult. And I think I could do it within probably three to six months of, if not faster.

[A]

Yeah, I mean, Even if it's 120, that's all I care about. I want to cover your spend and then a little bit more. I mean, the thing that's incredible, Rob, is that you're asking, can you do this? Should you do this? I don't know about the should. The can is not even a question. Of course you can. You've socked away so much money that it has given you the opportunity to make a transition. And, you know, even if it took you a year to get a job and, and you, you, like, really did, like, you're going to be fine. You're totally going to be fine. And, you know, by the way, if you get. If, let's say new guy comes in, you're like, oh, I hate him. And you give your notice. Right. You know, a couple things can happen. You can take your time. You can start converting more of your money, by the way, into a Roth And I think just to make things a little bit tidier for you as you anticipate that, I think what I would do, Mark, don't you think that not knowing what's happening and you know, being able to convert and do things like that. What do you think, Mark, about rolling the old retirement account, the 494, into his current traditional account?

[C]

Just to consolidate?

[A]

Yep, just to consolidate. And of course, if he wants to convert at the, on the, you know, once he's no longer employed at this place, we get rid of that IRA account. So he can actually just convert easily.

[C]

Yeah, I mean there's no downside to doing it.

[A]

So do you, do you like where your current plan is held?

[B]

Yeah, actually I think it's good. We have a lot of good options and it's cheap. It's a really big corporation, so they've got some good options for their employees.

[A]

So I would do that. I would make sure that you roll that in. So now you're 677 will have an infusion of almost a half a million dollars. It's all there, it's all tucked away nice and neat. Presuming you get your next job, you don't have to move your account so fast. You can just leave it there or, or you can, you know, we'll see. If you get another job, you might be able to roll it into the new company. But the amount of money you have saved is absolutely incredible. And you're not saying you want to just be done and never work again. You're saying I want to work. I mean, Mark, aren't you looking at these numbers and saying this is a slam dunk? Because I sure am.

[C]

Yeah. I mean he's given himself this opportunity based on everything that he has accumulated. Yeah, no doubt. I mean, if he wants to take a six month sabbatical and do nothing, go sit on the beach, go for it. I mean, you have the ability to do it.

[A]

You totally can do this. I mean, so I think just as Aunt Jill in your life, because you're a young man, I'd like to just offer the, let's wait and see what the new person's like. If the person is a nasty so and so, you can like just, you know, play it cool. You don't have to like say how dare you overlords have chosen him over me. You say very nicely, going to take some time, goodbye. And you leave. Well, and then look for a job. And honestly, if you started to look around now and you just to get a sense of like convincing yourself that you'll find a job that could make you 120 or 150. Great. You have no pressure. You never have to make 250 again if you don't want to.

[B]

Okay.

[A]

Really don't.

[B]

That's good to hear.

[A]

You know, and so the only other thing that is important here, just, you know, as you proceed and you go forward, is that, you know, I really just, I would hesitate to, like, make a life. Like, I'm going to do this or I'm going to, like, don't. No proclamations. But, like, for right now, I think you can walk away. You can feel good about that. You've put yourself in this great position. You don't have to do anything outrageous with any of your money. You really don't. You already have the money set aside to get you through the next period of time. And so I wouldn't really change much. I also wouldn't, I wouldn't burn up that cash anytime soon. So I wouldn't necessarily trigger a tax event right now if I didn't have to, because I like, I like you having that cash on hand.

[B]

So that leads me to kind of another question when it comes to, like, asset allocation. So right now I'm invested pretty aggressively. I'm like 90% stock, maybe 5% bonds if I count that pension and 5% in cash. Would you recommend, as I'm kind of working through this and still at my current job, that I just keep stacking as much cash as possible to fund either Roth conversions like you were mentioning, or obviously longer Runway, potentially of either not working or working for less money and having that.

[A]

Yeah, I would. And I also would suggest that especially if you start making less money this year, like if you leave this job, one other opportunity is, hey, maybe you've got some money in that brokerage account that has like an embedded long term capital gain, and maybe it would be really nice if you could just pay a 15% capital gains tax on it, free up some money, pop it in your cash account, use that potentially to help again that gap period of not earning income and also to finance the conversion to the Roth. And I think that'll work great. And you know, listen, if you. I think that a lot of this will be predicated on what happens next, like, what is the next job? So if that, if the next job, you know, if you say, oh, my God, Jill, I found something, I really like it, they like me, but it's only 80 grand a year, what should I do? Come back to us. Okay, okay. But I would, I mean, I would pull back being so aggressive and one way to do that would just be selling some low basis stuff in the brokerage. If you are, if you are going to truly be in a lower tax bracket, just freeing up some money and maybe that cash position, I would, would like it to be 10%, not 5%.

[B]

Okay, I'll work on building up that cash then in the meantime.

[A]

Yeah, I think it's great. Mark, any parting words for West Coast Rob?

[C]

All good. I mean, these assets are just going to continue to grow. You know, if early retirement in your 50s is part of the plan, you're going to have more than $4 million. You spend no money, you're going to have, you know, eighteen hundred dollars a month in a pension, your Social Security. I, I don't see any problem here.

[A]

I don't either. And by the way, the other thing to take away from this is don't be bullied or cajoled into doing something that you actually don't think is right for you, which I think you knew all the way in, but you sort of, they were like, come on, do this. And like, you know what, you know yourself better. And I think that you knew yourself when you first asked us about this, like you were already fried. So trust yourself. That's the other lesson here. Trust yourself because I think you have done a great job and you know, you don't. Just because a promotion is dangled out in front of you doesn't mean it's the right move for you. Right?

[B]

Yeah, it's hard when you, you trying to achieve or you're always trying to go for the next thing and people are encouraging you. You know, you get wrapped up in that. But yeah, I know, that's great advice.

[A]

I know. All right, West Coast Rob, thanks for joining us. Hey, are you considering a career change? Are you thinking about making a move that is sort of not a conventional part of what your previous thought process was? I'd love to hear from you, Mark, and I love these conversations. This was actually what prompted me to write the great money reset. And I think that if you're considering like something move like this, then of course buy the book. It's on our website, jillonmoney.com, you'll find the 10 Bold Signature Steps to turn chaos into opportunity. And of course you can always find [e-mail] the contact us button's always in the right hand, upper right hand corner. Write us a note, let us know if you want to come on the Air. We'd love, love, love talking to you. You can subscribe to us on the Odyssey app or wherever you find your favorite podcasts. Don't forget to lift someone up. Change your work, change your wealth, change your life. Thanks for listening. We'll talk to you tomorrow. Hey gang. I just made a first time ever purchase on behalf of the pod. I was so psyched because Mark and I don't do a lot of promotional materials, but I was able to create a branded sweatshirt. Yep, a Jill on Money branded sweatshirt with vistaprint. Now I'm not usually good at these things, but vistaprint made it simple to bring this idea like, oh, wouldn't it be cool if Mark and I could create some sweatshirts that we'll try out and maybe the listeners would want to get them as well. They've got these great design tools, they have fast shipping, human support. If you need a little guidance along the way. Because the sweatshirts were so easy to execute, now I'm thinking about doing some other stuff. Maybe there's some baseball caps or, I don't know, other fun stuff that you guys would want. You'll let us know. There's a reason that over a million people trust Vistaprint for their small business print needs. Vistaprint print your possible right now, new customers get 20% off with code [e-mail].

[D]

I'm Emma Grade, host of Aspire with Emma Grade, a podcast where I sit down with people who don't just dream big, they build big. From culture shaping voices like Mel Robbins, to leaders redefining success like Tracee Ellis Ross, to game changing entrepreneurs like Mark Cuban, Aspire is about mindset, ambition and doing the work that actually moves the needle. If you're ready to raise your standards and take charge about the life and career you're building, Aspire is where you start. Follow and listen to Aspire with me, Emma Greed and Audacy podcast. Available wherever you get your podcasts.