Podcast Summary: Jill on Money with Jill Schlesinger

Episode Title: Seeking Financial Flexibility
Date: December 9, 2025
Host: Jill Schlesinger, CFP® (with producer Mark)
Guest Caller: Lynn from Alaska

Overview of the Episode

This episode centers on a caller, Lynn, who is navigating mid-career financial planning and seeking strategies to gain flexibility and security as she and her husband approach retirement. Jill and Mark guide Lynn through issues surrounding pensions, Social Security (including the Windfall Elimination Provision), retirement savings, and the psychological/emotional trade-offs between financial goals and job satisfaction. The advice is practical, candid, and focused on real life circumstances, offering insights for listeners with similar questions about seeking flexibility before full retirement.

Key Discussion Points & Insights

1. Lynn’s Financial Snapshot

[03:42 – 04:41]

• Lynn (54) and her husband (52) both work full-time; children are grown.
• Husband will receive a defined benefit pension (PERS) of approx. $4,300/month at age 60.
• Lynn earns $75,000/year, husband earns $102,000/year.
• All kids are grown and independent.

2. The Retirement Metamorphosis and Desire for Flexibility

[03:42 – 04:01]

• Lynn’s goal is not a traditional “beach” retirement but having the financial flexibility to make other life decisions and possibly embark on a “next endeavor.”
• She wants the option to downshift or make employment changes without jeopardizing long-term security:

  “I’m starting to have a little bit of a metamorphosis when it comes to planning for retirement... to allow us some financial flexibility to make other decisions, a little next endeavor, a little look ahead.” – Lynn [03:42]

3. Understanding the Windfall Elimination Provision (WEP)

[05:39 – 07:59]

• Lynn is concerned about how WEP will impact her Social Security benefits, given much of her career is in higher ed (not covered by Social Security) and only 18 years with substantial SS-qualifying earnings.

• Mark explains she qualifies for SS with 10 years, but reduction under WEP depends on “substantial earnings” years.

• Jill clarifies:

  “When they calculate the amount... the windfall elimination, as it’s written right now, appears to apply either way. So regardless of what earnings record it goes against, you’re still going to get knocked down.” – Lynn [07:46]

• Lynn contemplates working more qualifying years to lessen the hit by changing the WEP reduction from ~40% (current) closer to 20%. She’s considering whether she should change jobs, stay in her field, or “crank” up SS-qualifying earnings:

  “I've got, you know, some working years left and I could work a few more years to have enough substantial earnings to change that percentage...” – Lynn [07:19]

4. Balancing Job Satisfaction vs. Maximizing Benefits

[08:00 – 08:15]

• Mark asks if Lynn enjoys her job. She responds:

  “I don't necessarily like the industry I'm in, but I like the type of work that I do... I just don't know that where I'm at is maybe the best fit.” – Lynn [08:05]

• Jill and Mark suggest not to endure an unsatisfactory job solely for maximum SS benefits, especially if it diminishes quality of life or mental health.

5. Current Savings, Debt, and Spending Needs

[08:51 – 10:39]

• Assets: $1,000,000+ in retirement savings (primarily pre-tax), $40,000 in Roth, $35,000 emergency fund.
• Debt: $275,000 mortgage on $525,000 house.
• No brokerage account.
• Annual living needs in retirement estimated at $100,000 (including taxes).
• Mark and Jill stress the importance of considering access to non-retirement (already taxed) money for greater flexibility:

  "We're going to need to have access to more money for you guys that has already been taxed... maybe to use instead of putting all that money into retirement." – Mark [13:07]

6. Evaluating Retirement Timeline & Income Gaps

[10:14 – 16:30]

• Husband’s pension ($4,300/mo) and Social Security (approx. $3,000/mo) will eventually suffice, but there’s a gap from ages 60-67 (pre-full SS).

• Lynn wants to have the option to make career changes within five years, possibly reducing income.

• Jill and Mark recommend:

  • Avoid focusing on paying off the mortgage early; prioritize cash flexibility and retirement savings.
  • Plan to work longer, perhaps in lower-stress, part-time, or more enjoyable roles, to reduce pressure on retirement assets during the crucial pre-SS years.
  • The later they can start tapping into retirement accounts, the stronger their overall plan will be.

• Memorable quote:

  “Even if you had to make a little bit less money for you as you make this shift, I'd be okay with that. As long as you're happier. Because if it meant that you could stay beyond five years, maybe it's seven years...” — Mark [15:20]

7. Job Change Considerations

[16:30 – 17:16]

• Lynn floats the idea of moving to a job with a defined benefit plan.

• Jill and Mark caution against putting the retirement plan ahead of job satisfaction:

  “Don’t go for the retirement plan or this plan or that. Get a job you like, because you are so lucky that…he’s got this defined benefit plan. You need to find something you like, actually want to be engaged with.” – Mark [16:53]

• The true driver should be finding “something where you feel like it’s... actually want to be engaged with. It matters less to me about what type of retirement plan you have.” – Mark [17:02]

8. Final Takeaways

[17:16 – 17:19]

• With current assets, future pension, and Social Security (even with WEP), Lynn and her husband are well positioned if they continue to work (albeit less or differently) through their early 60s.
• The focus should be on maximizing flexibility, maintaining happiness, and protecting against early depletion of assets by not making a sudden jump into retirement.

Notable Quotes & Timestamps

• “I’m starting to have a little bit of a metamorphosis when it comes to planning for retirement... to allow us some financial flexibility...”
  – Lynn [03:42]

• “When they calculate the amount... the windfall elimination, as it’s written right now, appears to apply either way. So regardless of what earnings record it goes against, you’re still going to get knocked down.”
  – Lynn [07:46]

• “I don't necessarily like the industry I'm in, but I like the type of work that I do...”
  – Lynn [08:05]

• “We're going to need to have access to more money for you guys that has already been taxed...”
  – Mark [13:07]

• “Even if you had to make a little bit less money for you as you make this shift, I'd be okay with that. As long as you're happier. Because if it meant that you could stay beyond five years, maybe it's seven years...”
  – Mark [15:20]

• “Don’t go for the retirement plan... Get a job you like, because you are so lucky that…he’s got this defined benefit plan.”
  – Mark [16:53]

Timestamps for Key Segments

• [02:54] – Main Show Begins (skip ads, intro)
• [03:42] – Lynn introduces her evolving retirement goals
• [05:39] – WEP and Social Security eligibility explained
• [08:00] – Discussing job satisfaction vs. benefits
• [08:51] – Current savings, debt, and asset overview
• [10:14] – Calculating retirement income needs
• [13:07] – Importance of taxable savings, not just retirement
• [15:20] – Advising phased, flexible semi-retirement
• [16:30] – Should Lynn seek another defined benefit plan?
• [17:14] – Episode wrap-up with final guidance

Tone and Style

Jill and Mark are practical, empathetic, reassuring, and honest. They balance the hard math of planning with sensitivity to emotional factors around work and life choices. Their advice avoids jargon, focuses on actionable steps, and emphasizes well-being and flexibility over rigid milestones.

Useful for Listeners Who…

• Fear running out of money if they downshift careers before full retirement
• Want to understand the Windfall Elimination Provision
• Are tempted to prioritize investment maximization at the expense of happiness
• Value straightforward, jargon-free financial advice with real-life context

Summary prepared for those seeking a comprehensive yet relatable breakdown of financial planning for flexibility, especially when considering non-linear or phased retirement paths.