Jill on Money with Jill Schlesinger

Episode: Best Strategy for Flexibility

Date: November 7, 2025

Overview

In this episode, Jill Schlesinger, CFP®, takes a call from Tom in Arizona, who—alongside his wife—wants advice on structuring their savings and investments to allow for maximum flexibility with an eye toward retiring (or at least downshifting to part-time work) in 15 years. The episode covers the nuances of prioritizing different investment vehicles, balancing retirement planning with near-term accessibility, and the mechanics of making such a long-term, flexible plan work. Co-host Mark joins to lend perspectives, especially around Roth strategies.

Key Discussion Points & Insights

Tom & Family's Financial Snapshot

• Ages: Both 40
• Children: 2 (8 and 5 years old)
• Income: ~$260,000 combined
• Retirement Savings:
  • $1.1 million in traditional 401(k)s
  • $50,000 in Roth IRAs
• Taxable Brokerage Account: $20,000 (newer focus)
• 529 College Savings: $30,000 combined
• High-Yield Savings: $80,000
• Home:
  • Value: ~$1 million
  • Mortgage: $450,000 at 6%
• Health Savings Account (HSA): ~$30,000–$35,000
• Other Notes: No pensions, no expected inheritance, "term" life insurance at $500,000 each, estate docs completed

Tom’s Big Question:

"What should our savings strategy be for flexibility, especially since we hope to retire (or downshift) in 15 years? We’ve been maxing out 401(k)s, but is that the best path now?"

Detailed Breakdown & Advice

1. Importance of Consulting Before Big Moves

Jill (01:45):

"If you're thinking about what happens next, or if you're weighing two different jobs, or if you're wondering whether it's time to buy a home, sell a home... get in touch with us. That's when we'd love to chat with you, not after you've already done something that it's harder to undo."

2. Current Savings Allocation

• Previously maxed out traditional 401(k) contributions
• Recently shifted strategy: Now only contributing enough to 401(k) to get the employer match (5% each), redirecting additional dollars into a taxable brokerage account (currently $1,200/month, going up to $2,000/month once youngest child enters elementary school)
• Ongoing 529 contributions ($250/month per child)

3. Should They Shift to Roth 401(k)?

Mark, Roth Subject-Matter Expert (10:03):

"I would obviously make the switch. I mean, they got a huge pile of pre-tax money already and they're so young. That's just going to keep growing and growing and growing. Yeah, I would make the switch."
Jill: Agrees, and notes if they need to access money before age 59½, taxable (brokerage) accounts offer flexibility.

4. Retirement Flexibility & Accessible Funds

• Jill and Mark agree that having a robust brokerage account is crucial given early retirement goals, since drawing from retirement accounts early is tricky/penalized.
• Brokerages offer access for living expenses, healthcare, or unexpected needs before traditional retirement age.
• Mark does a conservative projection:

  "Conservatively, in 15 years, they keep saving at their current pace, they're gonna have at least $4 million... Probably not enough to pump $10K a month in today's dollars, but you said you're open to a career change or downshift."

5. Life Insurance Needs

Jill recommends:

• Get more term life insurance (quote $1 million, 10–15 year policies for each spouse, given current $500,000 per person will be tight for family with kids).

6. Investment Choices

• Tom and wife mostly use plain index funds; Jill strongly affirms this.

  Jill (13:12): "Yeah. You know why? Because it works."

• Both Jill and Mark approve the move to prioritize brokerage with continued retirement and Roth contributions.

Notable Quotes & Memorable Moments

[04:15] Jill (about Tom’s 401(k) balance):

"Wow, you're so young. And look at all that money you’ve saved. Holy moly."

[06:05] Jill (on Tom’s wife wanting to retire early):

"Oh boy. She's putting the pressure on us. I feel like my neck is hurting already."

[10:23] Mark (on shifting to Roth 401(k)):

"They got a huge pile of pre-tax money already and they're so young. That's just going to keep growing and growing and growing. Yeah, I would make the switch."

[11:43] Jill (on the strategy):

"I love the idea of looking ahead... at least get you in the ballpark. I'm going to add to your actual expenses, because I think you need more life insurance."

[13:12] Jill (on index funds):

"Yeah. You know why? Because it works."

[14:01] Jill (on the time horizon):

"I never thought in terms of 15 years because it seems so far ahead."

Timestamps for Important Segments

• [02:44] — Tom introduces his family’s goal and situation
• [04:42] — Current investment accounts rundown
• [07:37] — Changing approach: from maxing 401(k) to match-only, rest into brokerage
• [09:04] — Discussion of Roth 401(k) option at work
• [10:23] — Mark: Strongly recommends Roth 401(k) contributions going forward
• [10:50] — Family's monthly expenses ($10,000 including mortgage)
• [11:43] — Jill and Mark: Projecting future plan, validate current approach
• [12:40] — Life insurance advice: seek $1M each in term coverage
• [13:12] — Index fund reassurance

Final Takeaways

• Flexibility is Key: For a 15-year (early) retirement plan, balancing accessible funds (brokerage) with tax-advantaged accounts is crucial.
• Shift to Roth 401(k): If you already have significant pre-tax savings and your employer offers it, especially while you’re young.
• Beef Up Life Insurance: With two young children and only a half-million each in term, get quotes for $1 million per spouse.
• Stay the Course: Index funds remain an optimal, low-stress approach; don't chase complexity.
• Check Back as Life Changes: Increase savings if income grows, and periodically reassess.

Quick Summary Table

| Account/Asset | Current Value | Recommendation | |-------------------|-----------------|--------------------------------------------| | Traditional 401(k)| $1.1M | Contribute only up to employer match | | Roth IRA | $50,000 | Continue maxing out annually | | Taxable Brokerage | $20,000 | Direct additional savings ($2000/mo soon) | | 529 College Funds | $30,000 total | Maintain $250/mo per child | | Home | $1M value, $450k mortgage (6%) | Stay, no immediate action | | HSA | $30k–$35k | Continue maxing | | Term Life Ins. | $500k/spouse | Increase to $1M 10-15 year term |

Bottom line:
Jill, Mark, and Tom all agree: the blended approach of securing retirement coupled with near-term flexibility is the best bet for early (or just flexible) retirement goals. Index funds, the right insurance, and intentional, forward-looking planning make this a model case for listeners aiming for similar outcomes.

For your own 15-year, 15-month, or even 15-day financial planning questions, Jill encourages you to reach out at Jillonmoney.com.