Episode Summary: "Downshift or Double Down?"
Podcast: Jill on Money with Jill Schlesinger
Date: September 15, 2025
Host: Jill Schlesinger, CFP®
Guest/Caller: Elise
Overview
In this episode of Jill on Money, Jill Schlesinger takes a listener call from Elise, a mid-career professional seeking a “gut check” on her family’s finances. Elise and her husband are considering a major life change: possibly moving out of their city for more space and family support, and maybe even taking their careers in a new direction. The discussion revolves around balancing retirement and college savings, assessing housing decisions, and, most importantly, evaluating how career choices interact with personal well-being and financial security. Jill unpacks the tough reality of high-cost living, steady (but not extraordinary) incomes, and the evolving priorities of a young family.
Key Discussion Points & Insights
1. Introduction & Caller Background (01:25–04:35)
- Elise (45) and her husband (46) live in the Northeast, both work full-time, and are parents to a 6-year-old and an 18-month-old.
- They juggle expensive childcare and rent, feeling squeezed but "okay."
- Elise describes herself as an "obsessive listener" of the show.
Memorable Moment:
“I think I’m just gonna sleep when I die is really where we’re at.”
— Elise, regarding parenting an 18-month-old (04:13)
2. Financial Snapshot (04:36–07:52)
- Income: Household earns ~$320k, plus unpredictable bonuses.
- Retirement Savings: Aggressively contributing to retirement. Elise’s 401(k) = $385k, Husband’s 401(k) = $60k. Additional rollovers and Roth accounts.
- Brokerage & Cash: $35k in a brokerage, $250k cash savings (emergency fund and/or possible home down payment).
- 529 College Savings: $83k for the older child, $37k for the younger.
- Rent: $3,000/mo for a space that is “getting tight.”
- No significant debt—only ~$9k in low-rate student loans.
3. The Crossroads: Relocation & Life Choices (07:52–13:33)
a. Why Move?
Elise feels they will outgrow their current apartment, especially with both working from home, and contemplate moving closer to family.
b. What Would Moving Cost?
- Houses near family cost $800k (possibly $500–900k).
- Mortgage estimate: $700k mortgage at 6.5% → principal & interest ~$4,400/mo.
- Property tax: ~$10k/year.
- Overall housing cost could double (from $3k to ~$6k/month).
Key Quote:
“You’ve got well below market rent in your area... Moving is not like the slam dunk save.”
— Jill (10:51)
c. Lifestyle Triggers
- Question: Can Elise afford to “slow down”—take a lower-paying, less demanding job?
- Jill highlights the need to clarify what a “better life” means for Elise and her family.
4. Crunching the Numbers & Gameplan (13:34–17:42)
a. Downshift Risk Analysis
- Jill walks through the risks: housing costs may increase, possible reduced retirement contributions, college is on the horizon, and the unique benefit of current low rent is hard to replicate.
- Jill preaches prudence: do not pull back on retirement savings yet.
Notable Exchange:
“I want to point out the obvious... wow, this is not looking so great for my game plan.”
— Jill, on moving’s financial downsides (12:56)
b. Career Reevaluation Homework
- Elise is well-regarded (“recruited regularly”), but her current job offers important parental benefits.
- Jill recommends exploring the job market methodically—see if a job at $200–220k could offer better balance.
Quote:
“You don’t know what’s going to happen next... given that you are feeling kind of fried, I think now is a good time to look.”
— Jill (14:24)
- Consider renting first if relocating, then buy after settling and (preferably) once mortgage rates improve.
5. Family Protection & Estate Planning (17:43–18:22)
- Insurance: They have life insurance, plan to increase coverage.
- Estate Planning: Documents drafted, just need witnessing and notarization.
6. Parting Guidance & Action Steps (18:23–18:41)
- Jill tells Elise to only make a major move if it makes life genuinely better.
- Continue funding retirement; pause extra 529 contributions for now.
- Homework: Research the job market, network, and focus on what “better” really means for their family.
Closing Advice:
“You’re only going to do this if your life’s going to get better. If you’re basically replicating the life you have and just making less money—no, thank you.”
— Jill (18:23)
Timestamps for Important Segments
- 01:25 – Elise introduces her family and situation
- 04:35 – Financial snapshot (income, kids, lifestyle)
- 07:52 – Specifics on housing, relocation, and financial goals
- 10:51 – Jill analyzes housing cost realities
- 12:56 – Acknowledging the challenge of the numbers
- 13:33 – Career introspection: Can Elise downshift, and what would that look like?
- 14:24 – Jill urges strategic career research
- 17:43 – Check-in on insurance and estate planning
- 18:23 – Jill’s parting summary and action steps
Memorable Quotes
- “I think I’m just gonna sleep when I die...”
— Elise (04:13) - “You’ve got well below market rent in your area... Moving is not like the slam dunk save.”
— Jill (10:51) - “You don’t know what’s going to happen next... given that you are feeling kind of fried, I think now is a good time to look.”
— Jill (14:24) - “You’re only going to do this if your life’s going to get better. If you’re basically replicating the life you have and just making less money—no, thank you.”
— Jill (18:23)
Takeaways
- Life transitions require holistic, honest analysis—not just financial calculations but also personal and career reassessment.
- Low rent can be a major hidden financial asset in high-cost areas—don’t give it up without real purpose.
- Job market research and networking are crucial for anyone at a career crossroads; don’t settle for “just less money” if it doesn’t mean a better life.
- Pause before big financial moves, especially with major variables (job, location, mortgage rates) up in the air.
Anyone grappling with similar mid-career, family, and financial crossroads will find both practical steps and empathy in this lively conversation. As Jill says, sometimes the wisest move is to simply “take a breath,” assess your options, and prioritize what will genuinely lift your family up.