Jill on Money with Jill Schlesinger

Episode: Can I Scale Back and Live a Bit More?
Date: August 22, 2025
Host: Jill Schlesinger, CFP®
Listener Guest: Catherine (Pacific Northwest)

Overview

In this episode, Jill takes a call from Catherine, a listener seeking guidance on whether she can afford to scale back her career and/or enjoy life more—such as taking more vacations or shifting to a less demanding job. Catherine is navigating the complexities of blending finances with her soon-to-be spouse, managing family responsibilities, and wrestling with the “permission” to tap into her significant savings. Jill offers a careful analysis of Catherine’s finances, reassures her about her financial security, and explores both practical and emotional barriers to making lifestyle changes.

Key Discussion Points and Insights

1. Catherine’s Current Situation

• Age & Partnership: Catherine is 46, partnered, and planning to marry this year. Her partner is 48.
• Income: Catherine earns approximately $186,000/year. Her partner earns $145,000/year and is in a job he enjoys with a pension benefit.
• Family: Four children between them. Catherine is responsible for two younger ones (ages 10 and 11) for college expenses; the older two are managed by the other parent.

Finances

• Catherine’s Assets:

  • 401(k): ~$180,000
  • Taxable brokerage accounts: $1.68M and $1M (the difference between them remains a bit unclear—possibly individual stocks vs. a long-held account)
  • HSA: $42,000
  • Savings: $98,000
  • Home: Worth $600,000, fully paid, no mortgage
  • 529 Accounts (College): $277,000 total, divided for the two younger children

• Partner’s Assets:

  • 401(k): $642,000
  • 457: $836,000
  • Pension: Estimated at $6,000/month starting at age 53 (in 5 years)

2. Desire for Change

• Catherine expresses wanting to either enjoy more discretionary spending (e.g., vacations to Europe) or scale back from her current demanding job (“mentally taxing”) to something less intense or of greater personal meaning, possibly at a significantly lower salary (~$90,000/year).
• She questions whether she’s saved “enough” to justify these choices, especially if her next job did not allow further retirement contributions.

Spending Patterns

• Current monthly expenses: $8,000–$9,000 (“fluctuates” depending on the month)
• Joint finances with her partner are not fully merged yet; they both contribute to a joint account for shared expenses but otherwise keep finances somewhat separate.

3. Jill’s Financial Analysis

Permission to Enjoy

• Emotional Block: Catherine has the means but feels “worried about being responsible for all these little people” and not giving herself “permission” to enjoy her money.
  • Jill: “Give yourself permission to go to Europe. Catherine, what is your problem? Why are you so mean to yourself?” [08:42]
• On Catherine’s Wealth:
  • “You have a lot of money, right? What’s the freak out here?…Even if…you spend ten grand a month, …you can do that.” [09:57]

“Can She Afford It?”

• Jill runs through the numbers and concludes that Catherine is already extremely secure.
  • Jill: “If Catherine wanted to basically take a job…maybe not even ever put any more money in retirement, and she was looking to generate eight grand a month…Do you think she has enough money saved so that she can, like, actually have a job that’s a much more meaningful job, scale back a little bit in time, make less money? Will all that money…be enough for her to live this life that she’d like to live? 100%. I mean, she’s very close to being there right now. Unbelievable.” [11:42]
• While not yet including her partner’s assets or pension, Jill is confident Catherine’s solo position is secure; fully merged, the financial picture is even stronger.
• Key Calculation: With a combined post-scale-back salary of $235,000 (“your 90 and his 145”) and current spending, the plan is feasible.

Next Steps & Considerations

• Clarifying the Real Question:
  • Jill presses Catherine to consider which change matters most: “Is it to work less and therefore…spend less, or…keep earning…but be able to spend a little more money? …That’s the real question.” [10:39]
• Testing Scenarios:
  • “If it were 90 grand and you could do something better, you’re 90 and his 145 could pay your bills. …You can do that. ...But I think it really requires you guys to sit down together and look at this together.” [13:45]
• Need to Consolidate: Jill encourages merging finances post-marriage for a clearer picture; currently, “we have like two thirds of the story and not the whole story yet.” [15:46]
• Estate Planning: Once married, update all estate documents.

4. Emotional & Behavioral Barriers

• Catherine’s lingering discomfort seems to be more about permission and psychological readiness than lack of means.
• Jill’s Closing Advice:
  • “I don’t want you to be in a terrible place where you’re, like, you’re spent, you know? So I think you should try to really work hard together. To say, like, is it really the job I have and the amount of time I’m spending, or is it like, I just don’t give myself permission to spend even with this job? I think that those are questions that we need to answer.” [16:18]

Notable Quotes & Memorable Moments

• Jill on Perspective:
  “You don’t spend that much money. Four kids is a lot. It’s three more than Mark has—put that in perspective.” [09:21]

• On Having a Well-off Ex:
  “I like, if you’re going to have an ex, I’d rather have a rich one than a poor one. Let me be great.” [09:11]

• On Scaling Back:
  “Sometimes I’ve talked to women who do this all the time. They’re like, I’m going to go part time. And it’s like they go part time, but it’s actually terrible because they end up working full time, getting paid half as much.” [13:13]

• Final Advice:
  “You’re young, you’re happy, like, enjoy yourselves. You’ve got a bunch thing going on. You’re good. …Take a deep breath and get us a little more information. Maybe you get back in touch with us with the fiancé on the line and we’ll pump him for information.” [16:43–17:04]

Important Timestamps

• 02:13 – Catherine introduces her question about scaling back and/or spending more
• 03:08 – Discussion of her income, marital status, partner's job and pension
• 04:36 – Review of Catherine’s retirement savings and brokerage accounts
• 05:44 – Home ownership and mortgage status
• 06:10 – Details of children and college savings
• 07:10 – Catherine's HSA and cash savings explained
• 07:37 – Partner’s retirement assets detailed
• 08:14 – Current and potential monthly spending discussed
• 11:16 – Main question: is her savings enough for scaling back?
• 12:31 – Jill’s calculation: “You’re very close to being there right now.”
• 13:36 – Exploring what “scaling back” would look like
• 16:09 – Estate planning reminder post-marriage
• 16:18 – Emotional readiness and giving herself permission

Summary & Actionable Takeaways

• Financial Security: Catherine is in an excellent financial position to either spend more or scale back at work, especially when combined with her partner’s pension and retirement assets.
• Next Steps:
  • Consolidate finances post-marriage to gain full clarity.
  • Decide jointly what spending and working levels bring the desired balance of enjoyment and long-term security.
  • Update estate documents after marriage.
  • Give herself “permission” to enjoy the wealth she’s accumulated.
• Invitation to Follow-Up: Jill suggests Catherine re-connect after marriage, ideally with her partner, for an even deeper analysis.

Tone: Supportive, practical, a little humorous, always direct.

For Listeners: Catherine's situation is a case study in both financial preparedness and the emotional/behavioral dimensions of money decisions—reminding us “having enough” is only part of the equation; being willing to enjoy it is another.