Jill on Money with Jill Schlesinger

Episode: Roth Conversions Leading to Early Retirement?

Date: January 13, 2026
Host: Jill Schlesinger, CFP®
Producer/Co-host: Mark

Overview

In this episode, Jill Schlesinger and co-host Mark tackle pressing listener questions centered on Roth conversions, early retirement strategies, and fee-only financial planning. The show features nuanced, jargon-free discussions about when—if ever—it makes sense to convert traditional pre-tax retirement funds to Roth accounts and how timing, tax brackets, liquidity, and individual retirement goals should influence your decision. Other listener questions address selecting a financial planner and best practices for estate and pension planning.

Main Discussion Points & Insights

1. Listener "SL": Should I Convert My Traditional 401(k) to a Roth?

[03:17 – 06:52]

• Listener Profile:

  • 49, single, no kids.
  • Targeting retirement readiness by 55 with $200k+/yr after-tax income.
  • $2.7M in brokerage, $600K in money market, $170K cash, $1.25M in traditional 401(k), $165K Roth, $40K HSA, $350K in a cash-balance pension.

• Listener’s Question:
  Should I convert my sizeable traditional 401(k) to a Roth IRA now (and pay taxes now), or wait until I'm in a potentially lower tax bracket? And should I shift future contributions to Roth?

• Jill & Mark’s View:

  • Liquidity: “We love conversions. We do think you need the liquidity to do this.” – Jill [04:24]
  • Timing Consideration:
    • Since SL is currently in the top bracket, converting now would mean hefty taxes.
    • "I just wonder if we might get a shot to be at a lower tax bracket," Mark advises, suggesting a strategic wait until early retirement, when taxable income may drop. [06:40]
  • Definitive Advice:
    • On Future Contributions: "The last part for me is a no brainer... Yes, I would switch going forward. You don't need any more tax deferred money." – Mark [05:53]
    • On Big Conversion: They recommend possibly waiting until after retiring at 55, when lower income could offer a better tax environment for conversions.

• Notable Quote:

  • "You're so close [to retirement]. It's only six years away and I would agree with Mark absolutely. You should put money into the Roth bucket as opposed to pre-tax at this point. Let's not compound the problem." – Jill [06:52]

2. Listener "Chris": How Do I Find a Fee-Only Financial Planner?

[07:32 – 08:43]

• Listener’s Frustration:
  Finding an advisor in California who doesn’t push products or manage assets.

• Jill’s Solution:

  • NAPFA: “National Association of Personal Financial Advisors... that’s N-A-P-F-A dot org.” [07:59]
  • XY Planning Network: For those wanting just a plan, not asset management: “xyplanningnetwork.com... this is a really good option.” [08:12]

• Notable Quote:

  • “Both of those things are possibilities for you.” – Jill [08:36]

3. Listener "Brooke": Roth Conversions and Early Retirement

[08:41 – 13:36]

• Listener Profile:

  • Age 35, married, two kids, sole provider.
  • $640K in traditional, $160K in Roth, $200K ESOP, $360K taxable brokerage, home paid off.
  • Living on $70K/year with goal to retire or semi-retire by 45–50.

• Key Questions:

  • Should I start small annual Roth conversions in the 22% tax bracket?
  • Is Rule 72(t) (substantially equal periodic payments from retirement accounts before age 59.5) a logical early-retirement strategy?

• Jill & Mark’s Analysis:

  • On Conversions: Cautious about big conversions now; if retirement income will drop within a decade, there may be better opportunities later for conversions in a lower bracket.
  • Rule 72(t): Supported as a useful option for early penalty-free withdrawals, but only with careful planning.
  • Compounding Growth Caveat:
    • "It’s very hard to do these small conversions... the accounts are going to grow at such a clip… It’s very hard to move the needle." – Mark [13:10–13:24]
  • Practical Tip:
    • Keep using Roth for new contributions; consider conversions only if they don't push you into higher tax brackets.

• Memorable Quote:

  • “The growth is going to, you know, probably surpass whatever amount you convert.” – Mark [13:30]

4. Listener "Steve": Estate Plan, Trusts and Beneficiaries

[13:35 – 15:10]

• Listener’s Situation:

  • Pension ($266K), $200K savings, $45K in 403(b), $116K IRA, $400K from house sale, $1,600/month Social Security.

• Estate Planning Concern:

  • Should retirement accounts, house proceeds, and other assets go into a trust?

• Jill’s Clarification:

  • Retirement accounts and pensions pass by beneficiary designation.
  • Trusts might help with non-retirement assets or for protecting assets against long-term care costs.
  • Discussion Encouraged: Speak with family and professionals for personalized guidance.

5. Listener "Victor": Military Survivor Benefit Plan

[15:14 – 16:14]

• Listener’s Question:
  Should I elect the survivor benefit plan for my military pension?

• Jill & Mark’s Guidance:

  • Depends on household needs, spouse’s finances, and relative life expectancy.
  • Generally recommended if a spouse is younger/has less other income.
  • More personal details are needed for a firm recommendation.

Notable Quotes & Moments

• On Roth Conversions:
  • "We do think you need the liquidity to do this." – Jill [04:24]
• About Waiting on Conversions:
  • "You’re so close. It’s only six years away... let’s not compound the problem." – Jill [06:52]
• On Finding a Planner:
  • “Check out NAPFA or XY Planning Network—both good options if you want just the plan, not a product being sold.” – Jill [08:12]
• On Small Roth Conversions:
  • “The accounts are going to grow at such a clip… it’s very hard to move the needle.” – Mark [13:10]
• On Military Pensions:
  • “If you have a spouse who’s really relying on you... we’re often saying, let’s do the survivor benefit.” – Jill [15:36]

Key Timestamps

• [02:20] – Show start, mission statement
• [03:17] – SL’s Roth conversion dilemma
• [05:53] – Mark’s take: Yes to future Roth, maybe wait on conversions
• [07:32] – Chris asks about fee-only planning
• [08:41] – Brooke’s Roth conversion and early retirement plan
• [13:35] – Steve’s trust/estate question
• [15:14] – Victor’s military pension survivor benefit question

Final Takeaway

Jill and Mark emphasize the importance of personalized, tax-aware strategy with big retirement account decisions, particularly for high earners considering Roth conversions or early retirement. Their advice consistently steers listeners away from blanket solutions and toward thoughtful timing, awareness of tax brackets, and consulting with reputable, fee-only planners.