Jill on Money with Jill Schlesinger
Episode: Left Government for Private Sector
Date: September 19, 2025
Host: Jill Schlesinger
Featured guest: Anna (Caller), with co-host Mark Telercio
Episode Overview
This episode focuses on financial transitions, specifically the journey from public to private sector work, and the resulting changes in income, retirement planning, and life goals. Anna, a listener from Washington D.C., calls in to unpack her family's new financial landscape after both she and her husband left federal government roles for private sector jobs. The conversation covers strategies for managing increased income, home and retirement planning, and balancing meaningful work with family needs and financial security.
Key Discussion Points & Insights
1. Navigating Career & Income Transitions
- Anna and her husband were “lifelong professional students” and recent federal government employees.
- Both now work in the private sector, almost doubling their income.
- Main concern: How to maximize financial growth during their private sector tenure, knowing Anna may want to return to public service for more meaningful work.
Memorable quote:
“My new job is good. It pays really well. However, it does not fill my professional cup like public service did.”
— Anna (03:38)
2. Current Financial Snapshot
- Both are 36 years old with a toddler and another child due soon.
- Combined income: $330k, projected to increase to $350k in 2-3 years (Anna as primary breadwinner, spouse at $60k).
- Home: Purchased at $795k, now valued at $825k. $756k remaining on a 4.5% fixed-rate mortgage.
- Savings: Maxing out retirement contributions where possible. Saving $3,000/month, currently at $18k; plan to reach ~$25k before the baby arrives.
- Retirement accounts:
- Anna: $45k in TSP (Roth), new Roth 401k ($17k) with 6% employer match, contributing 8% per paycheck.
- Husband: $25k in TSP (Roth) and $25k in 401k (not currently contributing due to baby on the way, but no match offered).
Memorable exchange:
Jill: “Is there a match, though? I want to make sure. We're not foregoing a match for him, are we?” (08:45)
Anna: “No, unfortunately, his employer does not match.” (08:49)
3. Housing Decisions: Stay, Upgrade, or Rent Out?
- Current house: Desire to keep through retirement; it's “snug”—two bedrooms, one bath.
- Considering moving to a larger house ($850-$900k) due to family size, leveraging a physician’s loan with little/no down payment.
- Investigated adding on to current home, but renovation quotes ($200-300k) deemed too high.
- Possibility to rent out current home: Very rentable, at least break-even or slight positive cash flow.
- Jill and Mark caution Anna about taking on too much at once (new baby, new home, keeping/renting first property).
Jill’s gentle warning:
“I almost feel like really, you're about to have a baby, you're going to have some maternity leave, and then you're going to throw this new house on top. There's like a lot of stuff.” (12:03)
Mark’s perspective:
“A newborn doesn't take up any space in the beginning... You have time. You could even push this out another year.” (13:08)
4. Planning for Public Service Return & Student Loan Forgiveness
- Anna left government for opportunity, not necessity ("sun is setting for us"), but wants to return if the right role appears.
- Public Service Loan Forgiveness (PSLF) was a consideration, but the new private sector job’s salary helps manage loans outright.
Anna’s personal insight:
“My heart's really very much in public service... I was set on PSLF. A blessing with this new job is it sort of takes care of it.” (15:01)
5. Risk Management and Future Planning
- Both have wills, estate planning, and life insurance addressed (thanks to early inspiration from listening to Jill’s show).
- Jill emphasizes continuing Roth contributions, especially at their age and the stage of their careers.
- Recommendation: Leave the thrift savings plans as they are; keep building up Roth assets.
Jill’s advice:
“Just leave the Thrift Savings plan where it is. Keep using Roth... The more you can do that now, the better.” (17:46)
Notable Quotes & Memorable Moments (with Timestamps)
-
On Moving for Money vs. Meaning:
“My new job is good. It pays really well. However, it does not fill my professional cup like public service did.”
— Anna (03:38) -
On the realities of timing a move:
“A newborn doesn’t take up any space in the beginning... You could even push this out another year. And by that point, mortgage rates may come down and it's really going to be a buyer's market.”
— Mark Telercio (13:08) -
On managing multiple life changes:
“I almost feel like really, you're about to have a baby, you're going to have some maternity leave, and then you're going to throw this new house on top. There's like a lot of stuff.”
— Jill Schlesinger (12:03) -
On financial catch-up and physician career paths:
“Often we talk to people who are doctors and... just not really starting. Like, if you look at your friend from college and you're like, my friend's been contributing to a 401k since she was 21. And like, yeah, but you were training.”
— Jill Schlesinger (17:46)
Actionable Takeaways
- Don’t rush big financial decisions when already facing large life events. Weigh the stress and bandwidth, even if the math works.
- Leverage Roth accounts when possible, especially at younger ages and during higher-earning years.
- Leave old government Thrift Savings Plans untouched; consolidate or roll over only after careful thought.
- If rental property is considered, ensure realistic expectations about property management and cash flow.
- Stay flexible: Be open to waiting for market conditions to improve, and don’t feel pressured to make every planned move immediately.
- Have full insurance and estate docs in order, especially with young children.
Structure & Tone
The conversation is warm, supportive, and honest, blending practical financial advice with empathy for the challenges of balancing career, family, and values. Jill and Mark engage as both experts and peers, drawing from personal experience to offer perspective without judgment.
Key Segments & Timestamps
- 01:42 – 03:38: Anna introduces her situation and goals
- 03:38 – 06:12: Anna and husband’s transition to the private sector, income, child on the way
- 06:12 – 10:00: Financial specifics—retirement savings, cash flow, home funding
- 10:00 – 12:03: House expansion vs. moving, rental possibilities
- 12:03 – 14:23: Jill and Mark's caution on timing and stress management
- 14:23 – 15:01: Anna discusses desire to return to public service and PSLF
- 16:21 –17:46: Final advice, insurance, estate planning, Roth strategy
- 17:46 – 18:45: Encouragement, wrap-up, “You’re in good shape”
For listeners in similar transitions—between sectors, or navigating suddenly increased income and responsibilities—this episode offers both reassurance and a clear set of priorities to help build long-term financial security without losing sight of personal fulfillment.