Podcast Summary: Jill on Money with Jill Schlesinger

Episode Title: When Can I Downsize My Job?
Date: January 15, 2026

Episode Overview

In this episode, Jill Schlesinger takes a listener call from Paul in Chicago, who is at a financial crossroads. Paul and his wife have worked hard, accumulated significant savings, and now wonder when and how to “downshift” to less demanding work and eventually retire. Jill guides Paul through their current financial situation, discusses possibilities for a phased retirement, explores the implications of purchasing a second home, and gives candid advice about life insurance and long-term planning.

Key Discussion Points and Insights

1. Paul’s Financial Overview and Goals

• Current Status:

  • Paul (57) and his wife (51) both work full-time and earn about $520,000 combined with bonuses.
  • Both max out their 401k contributions, primarily now using Roth accounts.
  • Retirement Savings: Roughly $3.2M in pre-tax (traditional) accounts, just under $400k in Roth accounts.
  • Brokerage Savings: Around $600k.
  • Homeownership: Owns a Chicago apartment worth ~$1.7M with a $500k mortgage at 2.75%.
  • Children: Two kids (one college freshman, one high school freshman), $500k in 529 plans for education.
  • Additional Assets: Deferred compensation (~$100k), company stock (~$65k vested), whole life insurance with $1M death benefit and $171k cash value.
  • Monthly Spending: Approximately $25,000.

• Primary Question/Goal:

  • When can Paul meaningfully “downsize” his career, ideally in 3-5 years, to focus on more meaningful or less stressful work, while maintaining his family’s financial security?

2. Defining the “Glide Path”: Phased Retirement

• Paul is not “miserable” but wants to slow down after decades of intense work, considering a transition to nonprofit work or teaching.

Jill’s Advice:

• With their substantial assets, good savings habits, and Paul’s wife’s intention and ability to work until 65, they have “a real buffer."
• Even a step down to a $100k salary for Paul is feasible, given his wife’s $220k salary and strong savings.

Quote

“Three to five years would be like good, right? ... If we could get you done at 60... you’d have a huge chunk of money that she’ll keep making. Instead of you making 300, could you make 100 and be happy doing something?”
– Jill (12:28)

3. Education and Family Financial Planning

• $500k in 529 plan savings supports private college tuition ($91k/year), requiring minor top-ups for the eldest, while continuing to support the younger child into college.
• Kids’ education fully accounted for, minimizing uncertainty.

4. Home Equity and the Second Home Dilemma

• Paul’s question: How to tap into their apartment’s significant equity without resorting to costly reverse mortgages?
• Considering buying a second, warmer location (possibly $500k), potentially using it as a rental.

Jill’s Caution:

• Advises not to rush into buying, especially without landlord experience.
• Recommends renting in any target area before purchasing, to test both the area and the landlord experience.

Quote

“I’m not a huge fan of trying to walk into the real estate market in my 60s, never having done that as a landlord... Make no big decisions, but try it out.”
– Jill (17:38)

5. Life Insurance Complexity

• Paul owns a whole life policy begun 15 years ago, with $1M death benefit, $171k cash value, $8k/year premium.
• Jill’s take: Hindsight suggests a 20-year term policy would’ve been much better, but given sunk costs, keep for now, at least until the youngest child finishes school.

Quote

“I love how you can delude yourself. ‘I’ve dug myself a hole for 15 years and now I’m finally reaping the benefit’...”
– Jill (09:31)

• Paul and his wife also have substantial term insurance and employer-provided coverage.

• Jill suggests an independent, fee-only planner could review the policy and their overall insurance needs.

6. Withdrawal Strategies and Future Planning

• Paul and wife will bridge early retirement income needs (before Social Security) by drawing from the brokerage, deferred comp, and retirement accounts.
• Jill assures them their plan is robust due to:
  • High ongoing income from Paul's wife
  • Ample retirement assets
  • Ability to cover health insurance through wife’s employment
  • No urgent need to tap home equity

Quote

“You’ve saved a lot of money and also spend a lot of money, but your wife’s willing to work and that does a lot of the heavy lifting for you. So I think this works.”
– Jill (14:40)

7. Estate and Investment Management

• Paul manages investments himself, has wills and a trust in place.
• Hesitates to pay a 1% assets-under-management fee; Jill suggests targeted planning advice is a better value.

Notable Quotes & Memorable Moments

• On the Cost of Private College

  “It’s a grotesque amount of money for a private institution.”
  – Paul (06:28)

• On the Glide Path to Retirement

  “If you work three more years, you can throw a little bit more money in the 529... In three years, you will have already saved... at your age 60 you’re done.”
  – Jill (13:08)

• On Owning Rental Property in Retirement

  “Unless you said to me, ‘We rented for three years in this southern place, we love it’... Otherwise, be careful.”
  – Jill (17:38)

• On Life Insurance Regret

  “If you’d bought yourself a 20-year term policy then and put the money in some mix of funds... I can guarantee you would’ve been better off.”
  – Jill (09:50)

Timestamps for Important Segments

• [02:10] – Paul introduces his goal of downshifting work
• [03:01] – Breakdown of household ages, jobs, and income
• [04:08] – Overview of retirement and brokerage savings
• [05:40] – Discussion of possible second home in a warmer climate
• [06:32] – Private college costs for their oldest child
• [07:50] – Cash holdings and approach to savings
• [08:51] – Whole life insurance dilemma
• [11:03] – Monthly household spending estimate ($25,000)
• [12:19] – Wife’s ongoing career supports long-term financial stability
• [13:08] – Jill lays out a path for a three-year off-ramp
• [15:23] – Health insurance will be covered by wife’s employment
• [16:08] – Real estate and rental property caution
• [18:13] – Estate planning status and DIY investing
• [18:52] – Jill recommends paying for targeted planning advice, especially for insurance

Tone and Listener Takeaways

• Jill is direct, approachable, and practical, blending realistic optimism with prudent caution.
• She celebrates solid financial decisions while humorously calling out missteps (e.g., whole life insurance).
• Listeners learn the importance of:
  • Building buffers into retirement plans.
  • Leveraging spouse’s ongoing income to smooth transitions.
  • Testing major lifestyle changes (like relocating or real estate investing) before committing.
  • Using targeted professional advice for complex areas.

Summary

Paul and his wife are on strong financial footing to begin downshifting work in 3-5 years, relying on ongoing salary, ample retirement savings, and careful planning. Jill underscores delaying any second home purchases, reevaluating insurance products, and maintaining flexibility in the years ahead to ensure both financial security and personal fulfillment in their next life phase.