Podcast Summary: Can We Retire in Five Years?

Jill on Money with Jill Schlesinger
Date: October 30, 2025
Guest: JJ from North Carolina

Overview

In this episode, Jill Schlesinger answers a listener’s question about retiring within five years. JJ, a self-employed professional from North Carolina, joins the show to discuss her and her husband’s readiness to retire early, navigating retirement account strategies, real estate decisions, and considerations influenced by family health history. Jill and her producer Mark provide clear, practical advice throughout, with a focus on creating flexibility and peace of mind.

Key Discussion Points & Insights

1. JJ’s Financial & Family Situation

• JJ and husband: Both 52, two kids (college junior and high school junior).
• Employment: JJ is self-employed ($120k/year); husband has W2 employment ($170k/year).
• College Funding: Fully funded 529s.
• Retirement Accounts:
  • Husband: Over $1.07M in pre-tax 401(k)s, $121k in Roth 401(k)s after a company merger.
  • JJ: $360k in SEP IRA, maxed annually.
• Real Estate:
  • Primary home: Worth $1.1M, fully paid off.
  • Investment property: Worth $400k, no mortgage.
• Debt: None.
• Cash savings: $120k.

2. The Retirement Timeline

• Goal: Both retire in 5 years (at 57), ideally moving to their investment property and freeing up capital from selling the primary home.
• Plan:
  • Sell primary home when kids move out, possibly live in investment property for two years for potential capital gains tax benefits.
  • JJ may continue working flexibly; husband's burnt out and eager to retire, but Jill suggests waiting for full financial security.

“He would love to do it in less than that. I just think it’s realistic.” – JJ, (09:32)

3. Retirement Savings: Pre-tax vs. Roth, and Brokerage Accounts

• SEP IRA Conversion?: Jill advises against unnecessary complexity. Stick with current SEP IRA setup.
• Roth Strategy:
  • Husband should direct new 401(k) contributions entirely to Roth.
• Brokerage Account:
  • Instead of extra into retirement accounts, build up a taxable brokerage account for extra flexibility and liquidity pre-59½.

“Forget about it, do nothing, do nothing. Keep doing your SEP IRA, it’s fine. Your husband, he should make his contribution all Roth.” – Jill, (12:20)

• Estimate of future assets:
  • ~ $2 million in retirement accounts in five years (conservative 3% growth).
  • ~$1 million from sale of primary.
  • Brokerage account recommended for supplemental liquidity.

[10:13] (Mark, the producer):

“$1,700,000.” (projected pre-tax retirement assets in 5 years at 3% growth)

4. Projected Spending Needs & Retirement Drawdown

• Living expenses:
  • Target: $6,000/month post-retirement after downsizing.
  • Jill reassures that this drawdown, supported by accrued assets and the sale of the primary home, is sustainable as long as spending doesn’t balloon.
• Withdrawal Strategy:
  • Wait to draw on IRAs/401(k)s until age 59½ (to avoid early withdrawal penalties).
  • Use proceeds from home sale and brokerage for bridge years (age 57-59½).
  • Start pulling from pre-tax retirement accounts after 59½, then consider Social Security strategy based on health and changing circumstances.

“You’ll blow a hole through your plan if all of a sudden you sell your investment property and decide you want to spend another million dollars on a house.” – Jill, (15:01)

5. Handling Multiple Retirement Accounts

• Consolidation:
  • Recommended rolling over old 401(k)s into the new employer plan if possible for simplicity.

6. Brokerage & Trust Considerations

• Brokerage Account Management:
  • Use ETFs or mutual/index funds to avoid compliance headaches (husband works at a financial institution).
• Titling & Beneficiaries:
  • Brokerage account should be titled in the family trust (if possible).
  • Checking accounts: Use “transfer on death” (TOD) designations for simplicity.
  • Retirement accounts: List individual beneficiaries (e.g. children).

“When you establish your brokerage account, that will be an account that is called the blanket, the JJ Trust… Should be labeled that way.” – Jill, (19:55)

7. Personal Factors & Health Considerations

• Family Alzheimer’s history:
  • JJ lost her mother to Alzheimer’s; this influences an emphasis on enjoying life earlier, being flexible, and potentially adjusting Social Security plans accordingly.

“You have an experience of living with something that’s very difficult and that influences what you choose to do next.” – Jill, (18:20)

Memorable Quotes & Moments

• On Retirement Readiness:

  “...at 57 you’re done, you have 80 grand coming in and self-employment income. I don’t think it’s worth it for you to go through the whole pain in the ass of moving your SEP… Keep doing your SEP IRA, it’s fine.” — Jill (12:20)

• On Brokerage Accounts Given Compliance Issues:

  “I don’t think they’ll have a problem with a brokerage account with three exchange traded funds… They don’t want you to do something where there could be a conflict…” — Jill (14:59)

• On Living for Today:

  “Let’s make some determinations about whether your Social Security claiming strategy shifts once you have a little more information about yourselves... You have your story. You have an experience... that influences what you choose to do next.” — Jill (18:10)

Timestamps for Key Segments

• 03:18 – JJ Introduces Her Situation
• 04:04 – College Planning and Funding
• 07:08 – Target Retirement Plan and Real Estate
• 09:14 – Husband Burnout and Retirement Hopes
• 10:13 – Future Portfolio Estimates
• 12:20 – SEP IRA, Roth Contributions, and Brokerage Strategy
• 14:21 – Brokerage Accounts & Job Compliance
• 17:02 – Withdrawal Timing (59½+), Health Considerations
• 19:38 – Estate and Beneficiary Planning

Actionable Takeaways

• Don’t overcomplicate existing retirement accounts; keep using SEP IRA unless needs change.
• Switch all new workplace retirement contributions to Roth for the higher earner.
• Focus on building a taxable brokerage account for short-term liquidity and flexibility.
• Use ETFs/mutual funds to simplify compliance issues for employees of financial firms.
• Title brokerage accounts in the family trust for easy estate administration; use TOD for checking.
• Only consider larger housing expenses after careful consideration—avoid “blowing a hole” in the plan.
• Plan for early withdrawal needs (between retirements and age 59½) using brokerage or home sale proceeds.
• Adapt Social Security claiming based on evolving health and family needs.
• Keep estate documents and beneficiary designations up-to-date.

This episode exemplifies Jill’s practical, plain-spoken approach, balancing the math with real-life circumstances to help callers make financial decisions that match their values and reality.