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

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.

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)

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)

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)

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)

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

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.

End of summary.