Can you afford to make a big life change?

Summary

Life Kit (NPR) — "Can you afford to make a big life change?"

Host: Marielle Segarra
Guest: Jill Schlesinger, CBS News Business Analyst & Author
Date: September 30, 2025

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Episode Overview

In this episode, Marielle Segarra and guest Jill Schlesinger explore one of life’s big questions: How do you know if you can afford to make a major life change—like quitting your job, starting something new, moving to a new place, or retiring early? Jill Schlesinger lays out a practical, step-by-step financial framework (the "Fabulous Five") to help listeners understand their resources, obligations, and possibilities when considering a significant reset. The conversation aims to empower listeners to take control, understand their situation, and make informed choices about their future.

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Key Discussion Points & Insights

1. The Challenge of Making Major Life Changes

• Emotional Conflict: Many people feel stuck due to the "sunk cost effect"—the feeling of being unable to leave something they've invested in, even if it no longer serves them.

  “Just because you’ve sunk some time, energy and money into something doesn’t mean that's the best thing for you to continue doing.”
  — Jill Schlesinger (01:08)

• Permission to Dream: Jill emphasizes the need to honestly assess your situation, not just to leave, but to give yourself mental permission to imagine a different future (01:36).

2. Jill’s "Fabulous Five": The Financial Reset Framework

Step 1: Calculate Your Resources

• What counts: Add up everything you own (assets): cash, checking/savings, retirement accounts, investment properties, home equity, and income (paycheck, benefits like health insurance, dependent care, etc.).
• Counting future benefits: Even assets you don’t have yet, such as a pension you’re entitled to later, should be noted.

• “It really is a real calculation of what you have and also what you might be giving up.”
  — Jill Schlesinger (04:08)

Step 2: Calculate Debts and Liabilities

• List all debts: mortgages, lines of credit, credit cards, car loans, education loans, etc.
• Don’t be discouraged: Jill stresses not to panic at this stage—knowing where you stand is just the first step.

  “Don’t throw in the towel in that moment… we’re just in the phase, the earliest stage of taking a good hard look at what you have and the position you’re in today.”
  — Jill Schlesinger (06:52)

Step 2.5 / 0: Take a Deep Breath

• Emotional check-in is a crucial (often overlooked) part of decision-making.

  “When you’re contemplating something in your life… it’s not, can I get this new job? It’s literally, I need to take a deep breath. I need to ask myself a hard question. Is this the way I really want to live? And the money part is the vehicle.”
  — Jill Schlesinger (08:00)

Step 3: Housing (Asset or Liability?)

• Assess what your home means for your finances and quality of life.
• For homeowners:
  • Would selling bring freedom or make you feel untethered?
  • Do the math: May not make sense to sell if you have a great mortgage rate.
• For renters:
  • Consider the total cost and recognize that renting can offer flexibility (sometimes overlooked).

  “I would really encourage you to understand that owning is also really hard and that you might have a better deal than you think. There’s plenty of very happy renters all over the country.”
  — Jill Schlesinger (10:40)

Step 4: Consider Your Spending Habits

• Track your actual spending, needs vs. wants.
• Sustainability: Question if your current lifestyle is sustainable—plans can change, and big shifts may require adjustments.

  “If you’re on this track where you’ve been spending a lot of money… you have to be sober about that analysis. Maybe [your family] will [adjust], but it is a lot of hard work to get there.”
  — Jill Schlesinger (11:42)

Step 5: Obligations to Others

• Acknowledge commitments and family responsibilities—do you have dependents, or obligations to siblings or elderly parents?

  “Have you made an obligation to your siblings… take on the care of mom? … When you consider those obligations, as you’re looking at your own reset, that could actually have a real impact for you.”
  — Jill Schlesinger (14:58)

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Making Sense of the Numbers: Scenario Planning

• Next Steps: Once you’ve filled out these five categories, look ahead. Ask, “What would the next 1-3 years look like if I made this change?”
  • Best, middle, and worst cases: Lay out scenarios for your finances and life satisfaction.

• “The first five steps are to figure out where you are today and then the scenarios that you build out… what happens to these five things in a year from now? If this is the best case, if it’s a middle case, and if it’s the worst case.”
  — Jill Schlesinger (15:47)

Jill’s Personal Example

• Worst case: The career change fails, and she returns to her old profession.
• Middle case: She transitions, makes less money, must hustle and possibly dip into savings.
• Best case: Finds fulfilling and well-paid work in a new field.

• “You don’t have to really worry about the best case. And as it turns out, the best case really did work.”
  — Jill Schlesinger (17:08)

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If the Reset Isn’t Possible Right Now: Building a Bridge

• Alternative Paths: If the numbers don’t add up, consider an interim plan instead of an all-or-nothing approach.
• • For example, work in your current field for a few more years to build up savings and create a clear timeline to transition.

  “Could you work for five more years, you’ll have some money coming in, and then you’ll build the pathway to your off ramp… I actually feel better about that middle case scenario.”
  — Jill Schlesinger (19:42)

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Notable Quotes & Memorable Moments

• On Sunk Cost Fallacy:

  “Just because you’ve sunk some time, energy and money into something doesn’t mean that's the best thing for you to continue doing.”
  (Jill Schlesinger, 01:04)

• On Taking Stock:

  “It’s not, can I get this new job? It’s literally, I need to take a deep breath. I need to ask myself a hard question. Is this the way I really want to live?”
  (Jill Schlesinger, 08:00)

• On Renting vs. Owning:

  “There’s plenty of very happy renters all over the country… most of the people… considering a reset have way more freedom to reset than those who own.”
  (Jill Schlesinger, 10:40)

• On Facing Reality:

  “You don’t know if this money reset is within your grasp unless you actually stop the fantasy land and do the math.”
  (Jill Schlesinger, 21:18)

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Timestamps for Key Segments

• Opening problem & sunk cost effect: 00:17 – 01:22
• Introduction of Jill's framework: 01:47 – 04:04
• Step 1 (Resources & Assets): 04:08 – 05:51
• Step 2 (Debts & Liabilities): 06:42 – 07:54
• Emotional Check-In ("Step 0/2.5"): 07:54 – 08:32
• Step 3 (Housing as Asset/Liability): 09:31 – 11:31
• Step 4 (Spending/Sustainability): 11:31 – 13:29
• Step 5 (Obligations): 14:55 – 15:36
• Putting it all together (Scenario planning): 15:36 – 17:08
• Jill’s own reset story: 17:08 – 19:16
• If the answer is “not yet” (Bridges): 19:42 – 21:18
• Closing remarks and actionable advice: 21:18 – 22:08

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Tone & Takeaways

The conversation is hopeful, smart, and pragmatic, focusing on both the emotional and practical aspects of major life changes. Jill brings both expert authority and personal relatability, encouraging listeners to dream big, but to ground those dreams in clear-eyed self-assessment and planning.

Bottom line:
You might not be able to do everything you want, but with honest accounting and realistic planning, you can likely do something—and perhaps even find peace with where you are.

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End of summary.

Transcript

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[Marielle Segarra]

You're listening to Life Kit from npr. Hey, it's Marielle. Have you ever found yourself toiling away at work, feeling completely burnt out and thinking, you know, what if I just quit, could I do that? Or maybe your work situation isn't dire, like it's fine, but you're ready for something new. You want to try another kind of job or start your own business. Or maybe you want to leave a marriage or move from your cold, dreary home state to a tropical climate that also happens to be more expensive. So often these callings feel impractical and out of reach. And you might feel like, how could.

[Jill Schlesinger]

I leave something I've invested so much into? This is called the sunk cost effect. It's actually like behavioral economics and it's actually pretty dangerous because just because you've sunk some time, energy and money into something doesn't mean that's the best thing for you to continue doing.

[Marielle Segarra]

That's Jill Schlesinger, a business analyst at CBS News and author of the book the Great Money Reset. She says if you're considering a reset, it helps to crunch the numbers, see what your finances look like, what might be possible for you and when.

[Jill Schlesinger]

And so part of the idea of taking this good, hard look and accounting for what's going on is to allow yourself the freedom to think beyond where you are. Currently.

[Marielle Segarra]

Schlesinger lays out a financial framework in the book, a set of steps you can use to make these decisions. In this episode of Life Kit, we'll walk you through it.

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[Marielle Segarra]

Okay, let's talk about the Financial Reset Framework. There are five steps, right?

[Jill Schlesinger]

I know, and it's kind of kitschy, so you'll forgive me if I get a little kitschy. I'm a little campy. I like a broad. If I could have put this to music, I would have, but I'm not that talented. I call it the Fabulous Five. So number one is you calculate the resources that you have and that means like what you own, those are your assets and your income and really everything. You know, like when I say what you own, a lot of people will say to me, well, I don't own anything. And I said, but don't you have a 401k? Oh yeah, I have that. So it really is a real calculation of kind of what you have and also what you might be giving up. So you know, for example, I have a lot of friends who are teachers and they'll say to me, well, I don't have a lot in retirement. I said, yes, but you have this amazing pension plan. So if you're entitled to a pension, you might include that as something you don't have today, but you would be entitled to in the future.

[Marielle Segarra]

So under income, there's obviously your paycheck, but then there are also other benefits you get, like subsidized health insurance, possibly through your job. Does that go under this category?

[Jill Schlesinger]

I think it really does because imagine what it would be if you had to do it all on your own. Imagine if you were saying, I'm going to reset, I have to go now into the Affordable Care act and buy my own coverage. And you just want to know what is the difference? Maybe you have kids and you're using a dependent care or flexible spending account, and you would lose that. Maybe you've got a match in your 401. So all that has to be taken into account.

[Marielle Segarra]

Yeah. And then in terms of assets, you mentioned one which is like, okay, so you have a lump sum of money in the bank or you have money in a retirement plan. What other kinds of assets might people consider in this step?

[Jill Schlesinger]

Anything that you would want to actually sell and that would make a difference. I'm much more concerned or much more focused on what you could convert to something easily to cash without any lag time, without, you know, paying a big tax bill. That's important. So I think it's more of your savings account. If you're in your, like, sort of middle aged, you have some investment property. And I think that a lot of people look at their home and they don't actually think of it as an asset, but it is usually people's largest asset. Right. When you have a home, there is usually something locked in there that's kind of amazing. And that's called equity. The difference between what the house is worth and what you owe on it. So I'm not saying you have to do anything with it, but it's really important to just at least count it as an asset.

[Marielle Segarra]

Yeah. And it's interesting that sort of leads us to step two, because your house can be an asset and it can also be a liability because you owe maybe a mortgage every month.

[Jill Schlesinger]

Right, right, right, exactly. And step two is calculate your debt and your other liabilities. Yes, of course, a mortgage. Maybe, um, maybe you're partnered and you say, you know, we, we took this line of credit to build an extra bathroom because, you know, we're a young family and, you know, three kids, one bathroom, not cutting it. And you have a line of credit that's also a liability. Maybe it's a credit card. Maybe you didn't quite pay everything off. It could be a car loan, education, loans, either for yourself or for your kids. All of those things come under this category of liabilities. And you know what happens when you're looking at these things. Don't throw in the towel in that moment. Okay? That's all I want to say. Like, I think that some people say, oh, I can't do it. I have all this debt. Okay. Calm down. We may be able to still do something. We're just in the phase, the earliest stage of taking a good hard look at what you have and the position you're in today.

[Marielle Segarra]

So this is not a step in your book, but I'm feeling like step two and a half is take a deep breath.

[Jill Schlesinger]

You know, it's funny. I think that might be step zero. You know, when you're contemplating something in your life and it boils down to a question of, you know, can I take. It's not, can I get this new job? It's literally, I need to take a deep breath. I need to ask myself a hard question. Is this the way I really want to live? And the money part is the vehicle.

[Marielle Segarra]

Yeah, I think that's a really good point. I mean, this is. The numbers are here to help you build a life that you want, right? It's a framework to help you get there.

[Jill Schlesinger]

It's the framework to give you the permission structure to see what's possible. You know, there's a lot of people who go through a process and they think about doing something different. And when I lay out the choices, they. They may come back to this and say, you know what? I'm actually good where I am. This happens a lot. It happens a real lot. And sometimes you need that reality check with yourself, and it sometimes can actually make you feel a little bit happier or more fulfilled on the path that you're on, rather than having that longing, because maybe your reset would force you to make a decision that you actually don't want to make. You know, I've had people who call me up and they say to me, you know, you know, I want to do something different. I'm making decent money. And we lay this out. And I said, okay, but, you know, how do you feel if you make this choice, not being able to help your kids get through college? Because you can do what you want to do, but you can't do everything you want to do.

[Marielle Segarra]

So let's move on to step three. We've been talking about housing, and that's what this step is about, right? What do you tell people to consider here? Here?

[Jill Schlesinger]

I think, first of all, is if I were to sell this house right now, what would that mean? How would I feel? Would I feel unburdened? Would I feel untethered? Right. Those are two opposite poles of something. Right? Would I feel like I could have more freedom to consider something else in the future? For a lot of people, selling their homes makes absolutely no sense. A lot of people Say to me, well, I have all this equity in my house. I said, yeah, but you also have a 2.85% 30 year fixed rate mortgage, and that's pretty amazing. Maybe you could use this house in a different way. Maybe if you want to move somewhere else or do something else, maybe you could rent the house. But again, I think the biggest question to ask is that, you know, what is it that I'm looking to reset and how does my housing play into that?

[Marielle Segarra]

Does this step only come into play if you own a home? Or it's also, what are the questions if you rent?

[Jill Schlesinger]

The renting is, you know, have I really looked at what it means to like, tally up the cost of where I am right now? And, you know, when rents were going crazy and a lot of people said, I hate renting, I hate that my landlord has all the power. I would really encourage you to understand that owning is also really hard and that you might have a better deal than you think. There's plenty of very happy renters all over the country. It's just that the internal revenue tax code favors people who buy, which is an annoying thing that always bothers me day to day. But it doesn't mean that renting's a bad choice. So most of the people who are renting and are considering a reset have way more freedom to reset than those who own.

[Marielle Segarra]

I feel like we've been talking about expenses here when we talk about rent, and that is step four, right. To consider your spending habits and what you have to spend.

[Jill Schlesinger]

Yeah, this is one of those strange steps that you have to take regardless of how much money you have. It really is, because, you know, you can be somebody who's just starting out and living really lean and then saying, well, if I actually want to be able to spend more money in the future, I'm going to have to make different choices about maybe a career. You know, I'm really, really stressing that this is not about living like a monk. This is just accounting for what your needs are and then what you actually are spending your money on. In other words, you don't necessarily have have to say, I'm going to cut my expenses by blank. And the other piece is it is hard to lower the amount of money you spend sometimes. So if you're on this, like, track where you've been spending a lot of money and you say, well, you know what, I'm going to leave corporate America and be a teacher. And you think your whole family is going to reset to a lower spending, you have to be sober about that analysis. Maybe they will, but it is a lot of hard work to get there.

[Marielle Segarra]

Yeah. I mean, part of step four or part of analyzing this, I guess.

[Jill Schlesinger]

Right.

[Marielle Segarra]

Would be considering whether your current lifestyle is actually sustainable.

[Jill Schlesinger]

Absolutely. So also a lot of this is like you make plans. Plans change and you have to be open and honest about this. Like this is not sustainable. And so part of considering your spending habits is. Is understanding that we make choices throughout our lives. You can change your mind and you can make different choices going forward.

[Marielle Segarra]

We will have more life kit after the break.

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[Marielle Segarra]

So what's step five?

[Jill Schlesinger]

So this is a little bit more of the emotional part. Step five is consider the obligations that you might have to others. And so it's very hard to have these conversations. So have you made an obligation to your siblings that, you know, well, I make a bunch of money and, you know, I'll take on the care of mom. Do you have a sibling who's likely to need help down the line? Yeah, you just want to know about that. And so when you consider those obligations, as you're looking at your own reset, you know, that could actually have a real impact for you.

[Marielle Segarra]

Coming out of the five steps, you have all these numbers written down and all these factors. What do you do with them? Like, what questions do you need to be asking yourself, once you know these.

[Jill Schlesinger]

Things, we have to have a premise, right? I don't tell people where they're resetting to. I presume that you come into this having thought that you want to do something else, right? So if you think about. Let's sort of kind of be like the very basic kind of reset. You know, if you say that I want to change careers, and what would that mean? So one of the things that you can do is you can look at those five steps and then look at, say, the next three years and say, what would that mean in the next three years? If I were to change careers, would I need to spend down some of my money? Could I meet my obligations? So all I'm saying to people who have a reset in mind is that you have to start with the end point, right? So the first five steps are to figure out where you are today and then the scenarios that you build out, or for maybe the first, say, one, two, three years to say what happens to these five things in a year from now. If this is the best case, if it's a middle case, and if it's.

[Marielle Segarra]

The worst case, you yourself made a big career change. You wanted to go from being a financial advisor to working in media. Can you walk us through your worst, middle and best case scenarios at that time?

[Jill Schlesinger]

When I thought about my reset, it was the financial crisis, okay? So I went through 2008 with my clients, and it was brutal. And in 2009 is when I thought, okay, well, my, you know, my contract's up. What the hell? I'm gonna do it. And so what I was trying to do was trying to figure out, you know, like, what is the best and the worst case scenario. So, you know me, I'm starting with the worst case. So my worst case was it would just wouldn't work. No one would ever put me on the air. And also, maybe I was like, I'm moving back home to New York with my family. And maybe I was like, oh, that was a re. There was a reason I was there out of that. That family for 10 years. Like, I didn't know because I hadn't been living in New York for 10 years. So then I said, okay, what's the middle case? The middle case would be that maybe I'd make a career transition, but it would not be as much money as I really wanted to make. And maybe it would be, you know, I wouldn't be, like, blissfully happy. I would be okay, but I was. I would really have to hustle. A lot more. And maybe I would have to eat through some of the savings that I had. Right. So, you know, not terrible. And maybe I'd have to like sort of also part time be in the financial services business. So then I was like, okay, best case this works out, I can get a job or string together enough income in the media industry. And so what I thought really was I thought that really the middle case scenario was most likely that I'd be fine money wise, no big deal. It wouldn't be like the thrilling career and I'd probably end up going into some other career. It would be okay. And the worst case, I would just figure out that I could be a financial planner, go sell something and you don't have to really worry about the best case. And as it turns out, the best case really did work.

[Marielle Segarra]

That's great. That's what we love to hear. Okay, so let's say that someone does go through this framework and they walk through the five steps and the worst, middle and best case scenarios and they decide, actually, I can't afford to do this right now or I don't want to make the sacrifices I would have to in order to do this right now. What are some ways they can build a bridge to the future that they want?

[Jill Schlesinger]

You know, it's funny, I write about this guy Ross, which is really, he's like a composite really, because he. I get a lot of questions from people who are in their 50s and they are exhausted. And you know, it's interesting to me because a lot of people who have acquired a lot of money sort of feel like, well, I have the money, I should be able to retire. Well, you know, again, you've got to run through all these numbers. And one of this, one of these conversations I had with this guy Ross is that, you know, he's like, I want to retire. And I said, you know, if you do that, it is like literally a high risk bet. Because in my mind, even if you quit right now and you went to work at a lower paying job, you could potentially blow through a lot of your money. And what I said, would it be okay if you, if we gave you a real interim game plan and we, and I could say to you, could you work for five more years, you'll have some money coming in and then you'll build the pathway to your off ramp. And I don't think that in the moment he was so psyched about that, but he did call me back and say, actually, I think that actually makes me feel more comfortable, like I have a time horizon. I know how much more time I have to do this. I can kind of suck it up. And once I have my game plan, I actually feel better about that middle case scenario.

[Marielle Segarra]

Yeah, well, and it feels like you're doing something as opposed to nothing.

[Jill Schlesinger]

Absolutely. I mean, look, you don't know if this money reset is within your grasp unless you actually stop the like fantasy land and do the math. You just don't know. And so one of the reasons that, I mean, I love the idea of thinking about the big picture and thinking about what you want, but I also like the idea that it's only by going through this very clear process and using a framework that you give yourself the permission to do it in the way that feels most comfortable to you.

[Marielle Segarra]

Well, Jill, thank you so much. This has been super helpful and actionable. I appreciate your time.

[Jill Schlesinger]

I thank you so much for having me, really.

[Marielle Segarra]

If you love Life Kit and you want more, follow us on Instagram prlifekit. There you'll find videos demonstrating some of our features, favorite tips, plus comics and cute little videos we make just for the gram about things like sleep, myths and flirting and how to find things you've lost. Again, we're on Instagram prlifekit. This episode of Life Kit was produced by Mia Venkat. Our visuals editor is Beck Harlan and our digital editor is Malika Garib. Megan Keane is our senior supervising editor and Beth Donovan is our Executive producer. Our production team also includes Andy Tagle, Claire Marie Schneider and Margaret Serino. Engineering support comes from Carly Strange. I'm Mariel Segarra. Thanks for listening.

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