Podcast Summary

Podcast: Jill on Money with Jill Schlesinger
Episode: Retirement and Leaving a Legacy
Date: February 13, 2026
Host: Jill Schlesinger, CFP®

Episode Overview

In this episode, Jill Schlesinger takes a call from “Jersey Mike,” a dedicated saver approaching retirement, to discuss the readiness of his financial plan, the trade-offs of pension-heavy income, tax and investment strategies in retirement, and considerations for leaving a legacy for his children. Jill unpacks Mike’s situation, offering actionable advice on managing required minimum distributions (RMDs), Roth conversions, estate planning, and balancing a comfortable retirement with plans for the next generation.

Key Discussion Points & Insights

1. Understanding Mike's (the Caller’s) Financial Situation

[03:03 – 07:12]

• Family Snapshot

  • Mike: 54 years old, employed full-time.
  • Wife: 51, now retired and receiving a pension.
  • Two children: 21 and 19, both in college and still financially supported.

• Income & Assets

  • Wife’s pension: $7,000/month (gross).
  • Anticipated pension for Mike upon retirement: $14,500/month (gross).
    • “My pension should be around $14,500 gross. Gross a month? Yes.” (Mike, 04:34)
  • Total pension income projected: $21,500/month (gross).
  • Monthly expenses: Generously estimated at $15,000 (“soup to nuts”).
  • Substantial savings/investments:
    • Joint account: $1,700,000
    • Rollover IRA: $585,000
    • Six-year deferred annuity: $565,000 (non-annuitized, two years remaining)
    • New York deferred compensation: $1,575,000
    • Checking/savings: ~$90–95,000

• Housing

  • Home value: $1.2–1.3 million, with $179,000 remaining mortgage.
  • Considering downsizing, potentially to a tax-friendlier or warmer location.

• Legacy Motivation

  • Mike is proud of being “financially free” and wants to pass down a legacy to his children.
    • “I'm really blessed, Jill, and it's really, I'm financially free and I'm...proud of what I'm starting, especially for my kids, you know, pass down a legacy for them.” (Mike, 08:48)

2. The Value (and Trade-off) of Pensions

[08:24 – 09:13]

• Jill highlights the often-misunderstood trade-off for pension earners: while pensions provide income security, they may result from jobs with lower salaries compared to private sector counterparts.
  • “Whenever we talk to people with pensions, I wonder if you understand, gang, if you don't have a pension, that usually that means you've made less money during your working years...there’s always a trade off here.” (Jill, 09:13)
• Jill emphasizes the impressive feat: Mike’s family built substantial wealth and security through long-term saving and investing discipline, not windfalls.

3. Tax Strategies, Annuities, and Roth Conversions

[10:05 – 12:18]

• Annuity Discussion

  • The annuity is non-qualified (funded with after-tax dollars).
  • Jill cautions about taxes: growth is taxed as ordinary income upon withdrawal.
    • “One of the reasons I hate annuities is that...whatever the difference is between what you put in and what you take out is ordinary income. Okay? So that's taxable...” (Jill, 10:37)
  • Mike plans to cash out the annuity in two years and add to joint assets.

• Managing Taxable Retirement Accounts (RMDs and Roth Conversions)

  • Jill notes the “curse and blessing” of having large pre-tax accounts.
  • Recommends considering incremental Roth conversions, especially prior to claiming Social Security, to manage future RMDs and keep taxes manageable.
    • “Maybe you start converting little by little...to stay in the 24% [tax] bracket...you’ll have more time to convert.” (Jill, 12:03)
  • Reiterates that waiting until age 70 to claim Social Security increases this conversion window.

4. Investment Risk & Legacy vs. Lifestyle

[12:18 – 13:17]

• Mike says he invests aggressively due to strong fixed income from pensions.
• Jill cautions against unnecessary risk—pointing out much of the nest egg is likely to benefit Mike’s children, not himself.
  • “If you said to me, oh, I'm investing very aggressively because I'm 55, it's not that—you're investing very aggressively because you have 20-somethings who you're investing for. That's what I think is the difference.” (Jill, 12:53)

5. Retirement Readiness & Enjoying Life

[13:17 – 13:53]

• Mike reflects on his public service and looks forward to enjoying retirement after hard work:
  • “In the public sector, it's almost...called the golden handcuffs...Emergencies, weather related stuff, all kinds of craziness.” (Mike, 13:17)
• Jill’s parting advice:
  • Update estate documents.
  • Consider tax planning with conversions.
  • Keep in touch when retirement actually happens, and share the experience!

Notable Quotes & Memorable Moments

• “Live your dream, baby. Live your dream.”
  — Jill, encouraging Mike to embrace retirement. (03:25)

• “No one ever buys an annuity. Annuities are sold.”
  — Jill explaining the issues with annuity products. (06:10)

• “It's not like a necessary thing...you're obviously investing for the kids, right? Because you're not going to use all this money.”
  — Jill reframes aggressive investing in the context of leaving a legacy. (12:53)

• “I’m financially free and...proud of what I'm starting, especially for my kids.”
  — Mike, reflecting on his life’s work. (08:48)

• “Our music is composed by Joel Goodman. Mark Teo is our executive producer and king of all things web.”
  — Jill, at the close, crediting her team. (14:20)

Timestamps for Key Segments

| Segment | Timestamp | |-------------------------------------------------|---------------| | Listener call with Mike begins | 03:03 | | Family and financial overview | 03:33–07:12 | | Home ownership and downsizing discussion | 07:01–08:17 | | Mike's path to financial freedom and legacy | 08:48–09:13 | | Pension trade-offs and perspective | 09:13 | | Tax strategy: annuity, RMDs, Roth conversions | 10:05–12:18 | | Investment risk tolerance & kids as legacy | 12:18–13:17 | | Mike’s career reflection & retirement plans | 13:17–13:53 |

Actionable Takeaways

• Evaluate Pension vs. Private Sector: Recognize the trade-offs in career paths—pensions often follow lower-salary roles.
• Plan for Taxes in Retirement: Prepare for RMDs if you have large tax-deferred accounts. Start Roth conversions while in lower brackets before claiming Social Security.
• Weigh Lifestyle vs. Legacy: High investment risk may not be necessary if core expenses are covered by pensions; consider the role of your portfolio in legacy planning.
• Update Estate Planning: Ensure wills, powers of attorney, and other documents are current to protect your legacy.
• Enjoy Retirement: Don’t delay savoring life post-career, especially after years of public service.

Tone & Closing Sentiment

As always, Jill is empathetic, direct, and practical. She celebrates Jersey Mike’s diligent savings and commitment to family, emphasizes the importance of thoughtful planning, and encourages listeners to dream big but be smart and proactive in managing both the blessing and the complexity of wealth.

“Enjoy yourself, give your notice...” — Jill’s signature blend of encouragement and solid advice.