Jill on Money – "Can I Retire in 18 Months?"

Date: March 19, 2026
Host: Jill Schlesinger, CFP® with producer Mark
Guest Caller: CJ from Wisconsin

Episode Overview

In this episode, Jill Schlesinger takes a call from CJ, a long-time professional contemplating a major life and career transition. With nearly 30 years in the workforce and significant financial assets, CJ wonders if it’s feasible to downshift to part-time work within the next 18 months. Jill and Mark walk through CJ’s financial landscape and explore the viability of his early semi-retirement plan, providing actionable insights and clear-eyed advice without financial jargon.

Key Discussion Points & Insights

1. Understanding CJ’s Motivation for Change (03:23)

• CJ’s career status:
  • Worked nearly 30 years, 22 at the same company.
  • Main reason for change: boredom, seeking a reset and more time flexibility, potentially in another field or reduced hours.
• Jill’s take:
  • “Once you go to part time, I doubt you’re going back to full time. Come on. Are we? Let’s be honest with each other.” (04:27)

2. The Family & Financial Snapshot (04:43–07:59)

• Demographics:
  • CJ: Age 50, married, three kids (one employed, one in college, one in high school).
  • Spouse: Age 49, self-employed in healthcare.
• Income:
  • CJ: $175,000/year (full-time).
  • Spouse: $100,000/year (gross).
  • Health insurance is only available through CJ’s work.
• Assets:
  • $1.4M in pre-tax retirement (403b/457 plans)
  • $700k in Roth/HSA
  • $200k in brokerage
  • Home fully owned ($500k), building new home ($700k value goal), construction loan in progress.
  • Medical office building (producing $10k/year in rental income).
  • $600k in vacant/recreational land.
• Expenses:
  • Around $5,000–$6,000/month (not including taxes or health insurance).
• Upcoming Changes:
  • New house will be ready by the summer, plan to use sale of current home to minimize new mortgage.

3. College Costs & Kids’ Status (05:33–05:56)

• Two kids still in school, using 529 savings accounts (roughly 75% funded for the sophomore; junior will have enough as well).
• College funding seen as manageable.

4. Retirement and Income Bridge Planning (10:53–17:18)

• Pension:
  • CJ eligible for a $55k/year pension at age 55 (joint and survivor, inflation-indexed).
• Gap Plan:
  • CJ is considering the transition to part-time at age 52, so needs to bridge income for ~3 years until pension starts.
• Cash Flow Strategy:
  • Jill’s suggestion: “You use that 457 as your main source of income from 52 to 55. Then, reduce the draw when the pension kicks in, and let the Roth accounts and brokerage grow.” (13:35)
  • Max out contributions to the 457 (better options, accessible at any age after separation); reduce 403b contributions to increase liquidity for the transition period.
• Social Security Potential (at 67):
  • CJ: $4,200/month
  • Spouse: $2,300/month

5. Real Estate Assets – To Sell or Not? (08:31–10:25, 12:10–12:33)

• Commercial property (medical building): Will be paid off soon. Could be a substantial additional asset (~$700k–$800k value).
• Vacant land ($600k value): Not income-generating. Jill leans toward eventually liquidating some or all if needed:
  • “That’s a lot of money to be tied up in something that we’re not using and not generating any money... I’m on your wife’s side right now. I’m team wife on this.” (10:34)
• CJ reluctant; his wife would like to sell.

6. Feasibility of CJ’s Plan (17:01–18:22)

• Mark sees the plan as “kind of a layup,” primarily because of the strong pension and continued spouse income:
  • “For me, the big thing is that pension. That’s a big pension. And they don’t spend a lot of money.” (17:14)
• Jill’s note of caution:
  • “You need a pinky swear with your wife that if this gets tight… you’ll sell some of these lots off... You have to be willing to do that if things get tight or circumstances change.” (17:16)
• Risks and variables include:
  • Kids needing more help
  • Wife ceasing to work earlier than planned
  • Rising living expenses (possible drift from $6,000 to $8,000/month)

7. CJ’s Future Work & Well-being (18:22–18:37)

• CJ unsure what part-time work he’ll pursue, open to anything, doesn’t mind if it’s not stimulating.

Notable Quotes & Moments

• On career change and honesty:
  “Once you go to part time, I doubt you’re going to full time. Come on. Are we? Let’s be honest with each other.” – Jill (04:27)
• On liquidity and tough decisions:
  “That’s a lot of money not to be doing anything with... I’m on your wife’s side right now. I’m team wife on this.” – Jill (10:34)
• On risk management:
  “You need a pinky swear... If we can’t do it, we’ll sell some of these lots off.” – Jill (17:16)
• On the financial plan’s strength:
  “Unless I’m missing something, this is one of those kind of layups for me because the wife’s going to keep working. He’s going to be working part time. They have a little bit of rental income. But for me, the big thing is that pension.” – Mark (17:01)

Timestamps for Major Segments

• 03:23 – CJ introduces himself and his desire for a career reset.
• 04:43 – Personal and family demographics, household income.
• 05:33 – Children status and college funding.
• 06:08 – Breakdown of retirement savings and assets.
• 07:00 – Real estate transition and home financing.
• 08:11 – Family spending, projected expenses, and health insurance needs.
• 09:05 – CJ’s anticipated part-time earnings.
• 10:25 – Real estate holdings: commercial and recreational.
• 10:53 – Details about CJ’s pension.
• 13:35 – Jill explains bridging income with the 457 plan.
• 17:01 – Mark declares the plan a “layup,” highlighting pension and frugality.
• 17:16 – Jill’s key risk-management advice.
• 18:22 – CJ’s thoughts on potential part-time work.

Final Guidance

Jill’s summary for CJ:

• The early semi-retirement plan can work, thanks to a strong pension, spousal earnings, and substantial assets.
• Maintain flexibility with real estate assets (“pinky swear” to sell some land if cash flow is tight).
• Be prepared for the possibility of expenses rising, spousal retirement timing changes, or kids needing more support.
• Build more liquidity in the short term, favoring the 457 plan over the 403b.

Listener Takeaway

If you’re contemplating a major career reset like CJ, do the homework on your future cash flows, keep your options open, and consider your family’s full asset picture—including illiquid real estate. And, as always, enlist a “team” for an outside perspective, whether that’s a spouse, financial expert, or the Jill on Money community.