Podcast Summary: Jill on Money with Jill Schlesinger

Episode Title: Moving From Saving to Spending
Date: March 17, 2026
Host: Jill Schlesinger
Producer/Co-host: Mark Tallagio
Featured Caller: Chris from Seattle

Overview

In this episode, Jill Schlesinger addresses one of the most challenging transitions in personal finance: shifting from a lifetime of diligent saving to spending in retirement. Caller Chris, a recent retiree, seeks advice on everything from Roth conversions and withdrawal strategies to tax minimization, asset consolidation, and gifting. Jill and Mark dive deep into Chris's financial situation, using it as a case study to explore the psychological and tactical aspects of entering the “spending phase.”

Key Discussion Points & Insights

1. Transitioning Mindset: Saving to Spending

• Chris's Dilemma: Recently retired, lifelong saver, finds it hard to shift to spending.
  • "I am just a huge time saver and kind of having a struggle moving from the saving mode to spending." – Chris [05:09]
• Jill empathizes, noting this is a common challenge for dedicated savers.

2. Roth Conversion Strategy

• Current Situation: Chris, 61, single, with a mix of Roth, traditional, and taxable assets.
• Jill's Advice: This year presents a prime opportunity for Roth conversions due to lower taxable income (pre-pension, pre-Social Security).
  • "You'd be in the 22% bracket and I think you probably should do some conversions." – Jill [11:22]
• Suggested Approach: Convert $150,000 this year, taking the tax hit now while in a lower bracket, and use high-yield savings/CDs to pay the tax.
  • Alternate: Just withdraw from 401(k) for living expenses, pay taxes as needed, without converting.
• Mark's Take: Leaning toward just “yanking it out” for expenses as conversion of all pre-tax balance isn’t practical.
  • "There's so much pre-tax money. He's never going to get all this converted." – Mark [14:18]

3. Withdrawal Strategy and Cash Flow

• Chris currently pulls from a combination of 401(k), brokerage, and high-yield savings.
• Pension (available at 62) will cover a large part of annual expenses.
• Jill and Mark discuss optimizing withdrawal timing and sources to minimize taxes, suggesting flexibility as pension and Social Security kick in.

4. Timing Social Security

• Jill's Input: Delaying Social Security to age 70 maximizes benefit, but individual health and needs should factor in.
  • "Pretty good sounds like 67. Really good sounds like 70...if you’re in good health, the longer you wait, the better off you are." – Jill [12:54]
• Chris’s Projected Benefits: $3,700/month at 67 or $4,600/month at 70 [13:10]

5. Consolidating Accounts

• Current Setup: Assets divided between Fidelity (former employer’s plan) and Edward Jones (brokerage).
• Jill encourages consolidation for ease of management, favoring the provider offering better advice and value.
  • "I like combining. Why? Because it's easier to manage." – Jill [18:31]
• Action Item: Urges Chris to check Edward Jones’ fees and compare the quality of advice.

6. Charitable Giving & Donor-Advised Funds (DAF)

• Chris is charitably inclined, both for eventual legacy and current giving.
• Jill recommends using appreciated securities in the brokerage account to fund a DAF, allowing tax-smart giving over time.
  • "You could essentially open a donor advised fund...immediate $100,000 deduction on your taxes...you don’t have to give it away all at once." – Jill [17:39]
• Suggests future large tax years as opportune moments to contribute to a DAF, and highlights practical benefits and mechanics.

7. Family Gifting

• Chris mentions having brothers, nephews, and a niece—potential beneficiaries.
• Jill suggests considering gifts during their lives, when they can use the money.

8. Action Steps for Chris

• Decide on Roth conversion amount and preferred method (conversion vs. withdrawal).
• Analyze current advisory fees vs. tangible value at Edward Jones.
• Consider consolidation based on where service is best.
• Explore donor-advised fund to amplify charitable efforts and maximize tax benefits.
• Consider gifts to family while living.

Notable Quotes & Memorable Moments

• On Retirement Mindset:
  • "We're going to turn you into a spender or a philanthropist in about two seconds." – Jill [20:59]
• On Over-saving:
  • "You’re incredible...I'm single." – Jill, marveling at Chris’s savings [08:32]
• Reflections on Podcast Origins:
  • "We created the seven-day show because there were so many questions coming from you...let’s just do the show we want to do." – Jill [04:00]

Timestamps for Important Segments

• [05:01] – Chris introduces his main dilemma: how to move from saving to spending and asks about Roth conversions and withdrawal strategy.
• [06:36] – Review of Chris’s substantial retirement and brokerage account balances.
• [09:05] – Discussion of Chris’s monthly spending needs and current withdrawal methods.
• [11:22] – Jill suggests making a large Roth conversion in 2026.
• [12:54] – Social Security timing debate for maximizing benefits.
• [14:18] – Mark leans toward simply withdrawing for living expenses rather than aggressive Roth conversions.
• [17:39] – Jill details the mechanics and advantages of donor-advised funds.
• [18:31] – Advocacy for consolidating accounts; warning to check advisory fees.
• [20:59] – Jill encourages Chris to spend or give away money and keep in touch with progress.

Tone & Language

• The episode is conversational, humorous, and supportive, mixing practical financial advice with friendly encouragement.
• Jill and Mark are empathetic and direct, balancing financial expertise with real-world relatability.

Summary Takeaways

Chris exemplifies the challenges that face many new retirees: overcoming saver’s guilt, optimizing withdrawals and taxes, and finding fulfilling ways to deploy wealth. With Jill’s practical, jargon-free guidance, listeners learn about the psychological flip required for retirement, the strategic use of Roth conversions, the value of consolidated account management, and tools like donor-advised funds for impactful giving. The episode wraps up with a focus on aligning finances with values, both for living well and leaving a legacy.

For financial questions or to appear on the show, Jill and Mark invite listeners to contact them at jillonmoney.com.