Jill on Money with Jill Schlesinger

Episode: Feeling Lost, What's the Next Step?
Date: September 5, 2025
Host: Jill Schlesinger, CFP®
Producer: Mark Dalerisio
Main Caller: Anne from Connecticut

Episode Overview

In this episode, Jill dives into a listener’s detailed, real-world case study about handling significant accumulated wealth, especially as retirement nears and the transition from saving to strategizing tax-efficient withdrawals becomes daunting. The main focus: how to navigate complex portfolios, prepare for required minimum distributions (RMDs), and decide whether to consolidate accounts and/or seek more tailored financial advice. Jill provides actionable insights while breaking down complicated concepts into relatable, practical takeaways.

Key Discussion Points & Insights

1. Catching Up Post-Labor Day

[01:07 – 05:04]

• Jill welcomes listeners back after a break, expressing genuine excitement to reconnect.
• Brief banter with producer Mark Dalerisio about his challenging trip to China.
• Jill reflects on how much she enjoys interacting with her audience compared to her TV work:
  "This is by far the most fun that I have all week long, which is why I feel like I'm excited to talk to you all." (04:14)

2. Upcoming Live Event: Estate Planning Focus

[04:44 – 05:13]

• Jill promotes the September 10th Jill on Money Live webinar centered on estate planning, bringing in an attorney and a financial therapist for holistic guidance.

3. Main Caller: Anne's Wealth Journey

[05:17 – 27:45]

a) Background on Anne’s Financial Life

• Anne and her husband started with little, made steady progress, and steadily invested their growing surplus over decades, primarily through simple index funds and brokerage accounts.
• Received advice from a friend to diversify and set up proper college funds (UTMAs).
• Inherited assets from her parents, placed into a trust intended for her eventual heirs.

b) Asset Overview

[07:32 – 12:05]

• Joint self-managed account: ~$1MM
• Trust (inherited, now in Anne's name): $466K
• Muni bond managed account: $391K
• Joint managed account at Morgan Stanley: $915K
• Three former UTMA accounts (for their children): $160K each (~$480K)
• Retirement accounts:
  • Tom's IRA: $910K
  • Anne’s IRA: $976K
  • Anne’s 401(k): $1.7MM
• Primary residence: $1.6MM, no mortgage

c) Family and Income Details

[12:05 – 15:00]

• Anne (66, working, $600K annual income, physician), Tom (68, retired).
• Three adult daughters, independent or nearly there—one with significant self-made savings.
• Tom and Anne both plan to delay Social Security to age 70 for full benefits.
• Anne also has a robust pension: $6,240/month starting at 70.

d) Spending Needs & Retirement Income Planning

[14:45 – 16:38]

• Realistic monthly spending currently around $20K–$25K; can spike higher due to taxes.
• Projected retirement income from Social Security and pension: ~$13,800/month.
• Will need to supplement from savings/investments for desired lifestyle.

e) Retirement Account Tally

[16:04 – 16:47]

• Jointly, they hold over $3.5MM in pre-tax retirement accounts, not yet subject to RMDs.

f) Anne’s Main Concern: “Am I Doing This Right?”

[17:15 – 18:56]

• Worries about a looming “huge tax liability.”
• Seeking guidance on whether to consolidate, adjust investment approach, or pursue more active management (advisor recommended “Parametric”/custom core for tax efficiency).
• Expresses self-doubt:
  "I kind of feel like a rube. I feel like a foreigner in this land of finance… Part of me wants to just trust the guy at Morgan Stanley and say, just do it. Fix it. Take care of everything." (18:52, Anne)

g) Skepticism Around Financial Advice

[18:56 – 19:18]

• Anne is hesitant about blindly trusting advisors, citing local doctors who lost pensions to Bernie Madoff:
  "There's a medical group in my town who had a great pension plan invested with a guy that had great returns, and his name was Bernie Madoff." (18:58, Anne)

h) Jill’s Core Recommendations

[20:23 – 26:15]

• Acknowledges Anne has “won the game” financially and will not outspend her assets.
• Primary focus should now be on efficient withdrawal and minimizing taxes—especially on the sizable pre-tax retirement nest egg.
• Encourages interviewing multiple financial planners for a second opinion, not limiting to Morgan Stanley, even if familiar with their tools like Parametric:
  "You guys are a perfect couple to consider shopping around for a real financial planner... This is your moment in time." (23:25, Jill)
• Looks at fees: with $4MM at Morgan Stanley, 1% management fee seems high; with assets at this level, lower rates might be negotiable.
• Stresses importance of “implementation” and not just plan creation—help with RMD strategies, tax-efficient withdrawals, and legacy planning is vital, not just accumulating assets.
• Notes that now is the time to switch mindset from accumulation to distribution and efficiency.

i) Advice: Get Second Opinions & Validation

[26:15 – 27:45]

• Urges Anne to use her “second opinion” instincts from medicine for finance as well.
• Reinforces:
  “You’re in very good shape and in great shape. So congratulations about that mostly. And then also I want to be clear that whoever you decide to move forward with, it’s like you’re in medicine, right? You get second opinions.” (26:48, Jill)
• Notes it's not just about not outliving your money, but passing it to kids efficiently and planning for taxes.

Notable Quotes & Memorable Moments

• On the reality of wealth accumulation as a late-career high earner:
  "This is what happens when you are born at the right time in the right generation and you keep investing early." (20:05, Jill)
• Anne’s humility on managing money:
  "I kind of feel like a rube. I feel like a foreigner in this land of finance." (18:52, Anne)
• Jill on the need for professional guidance:
  “This is your moment in time… to put together a strategy with a [financial] advisor who will develop that strategy with you, who will implement that strategy with you, who will help you make sure that the money gets passed on to your kids in the way that you want.” (23:25, Jill)

Important Timestamps

• 01:07: Jill’s return, post-vacation enthusiasm
• 05:17: Anne introduces her background from Connecticut
• 06:58: Anne describes the formation of various investment accounts over time
• 07:32 – 12:05: Detailed rundown of Anne’s various accounts and asset values
• 12:22: Anne discloses her income as a physician: ~$600K/year
• 14:45: Reveals real (and rising) monthly spending: $20K–$25K/month
• 16:10 – 16:38: Overview of the couple's retirement savings
• 18:52: Anne worries about being a “foreigner in this land of finance”
• 20:23: Jill begins her strategic overview on managing taxes and withdrawals
• 23:25: Jill insists on the value of seeking multiple planner perspectives
• 26:48: The importance of second opinions and not “shopping by price” alone

Summary Flow and Takeaways

Jill on Money’s case study with Anne is a masterclass in practical, late-career financial planning—especially for those who “did everything right” but now must shift focus from growing to efficiently using and distributing wealth. The episode balances technical advice with empathy, normalizing the feeling of being “lost” when moving into a new financial phase. Jill’s repeated emphasis is on planning for what’s next—not just what worked before.

Listeners in similar situations—complex assets, impending RMDs, concern about advisor recommendations—will come away with clear steps:

• Inventory assets and income needs
• Seek truly independent, comprehensive financial planning (not just product management)
• Get second opinions, just like in medicine
• Always weigh fees against the value provided at higher wealth levels

Jill’s tone is straightforward, slightly irreverent, and always rooted in real-world practicality, encouraging listeners to “lift someone up,” take charge, and embrace both the privilege and responsibility of wise wealth stewardship.