Jill on Money with Jill Schlesinger
Episode: Should I Combine Accounts?
Date: August 26, 2025

Episode Overview

In this episode, Jill Schlesinger takes listener questions on practical money and investing dilemmas, focusing on topics like consolidating retirement accounts, managing retirement withdrawals, investing strategies for families, and financial plans for grandchildren. As always, Jill and her producer Mark provide clear, jargon-free advice rooted in actionable steps, all while keeping the tone light and humorous.

Key Discussion Points & Insights

1. Should I Combine My 401(k) Accounts?

(Starts at 03:00)

• Listener Thomas asks if he should combine his two 401(k) accounts upon retiring at 66—one with $1M with his current employer and another with $300k, plus a $70k pension.
• Jill's Advice:
  • She recommends consolidation: "Yes, Thomas, I love consolidation and Mark and I are big fans. So I think when possible combining is great." (04:00)
  • Suggests rolling over the smaller account into the larger one, especially if the larger account provider (she hints at companies like Vanguard, Schwab, Fidelity, T. Rowe Price) offers low-fee index funds.
  • Tip: If pitched by an investment advisor for consolidation but you are comfortable managing it yourself, Jill says: "You say, no thank you, I’ll do it myself." (05:00)
  • Use self-directed options to keep fees low and retain control.

2. Retirement Withdrawal & Stock Concentration Strategy

(Starts at 05:30)

• Listener Bill: Retiring couple (65 and 64) with $1.2M in 401(k), $560k in a single dividend stock, $180k in high-yield savings, $7k Roth, $15k HSA, paid-off $550k home; plan to work part-time and wait until 70 to claim Social Security (~$6,500/mo).
• Issue: Whether to sell stock gradually for gap years, or use other funds.
• Jill's Guidance:
  • Advises drawing from the 401(k) instead of the concentrated stock position: "I think what's more important is for you to start pulling the money out of the 401(k)—that's the ticking time bomb." (06:04)
  • Urges diversification: "You should make sure those dividends go into cash and you should start to diversify... I’d be diversifying a little bit anyway from that account and maybe a lot of bit."
  • Suggests consulting a CPA for optimal withdrawal strategy.
  • On working part-time: Mark comments, "They don’t have to work part time unless they want to." (06:41)

3. Am I 'Late' Investing in a Brokerage Account?

(Starts at 07:00)

• Listener Jack (41): Increased income, two kids (15 & 10), $625k in 401(k), solid 529s for kids, $75k emergency fund, new taxable brokerage, investing in S&P 500, NASDAQ, and dividend funds. Feels 'late' on investing outside retirement accounts.
• Jill & Mark's Response:
  • Jill: "Stop judging this gang. You are where you are. I hate that. You’re not late." (07:28)
  • Reassures Jack is ahead for his age.
  • Investment Mix Advice:
    • Mark: "As far as the brokerage account, I wouldn’t use those three funds. I would stick with the VOO [S&P 500 index]. Yes, I would probably mix in some bonds in the brokerage account as well." (09:30)
    • Jill: Advocates for rebalancing, adding international exposure, considering backdoor Roth if income is high, but shifting more to Roth in the retirement account may be simpler.
    • Suggests funneling more into 529 for the older child if college is a priority.

4. Are We Spending Too Much in Retirement?

(Starts at 11:30)

• Listener Jane: Retired couple in late 70s, $92k/yr Social Security, $710k in IRAs, $200k Roth, $100–120k cash/CDs, $120k annual spending, $750k home with $125k mortgage.
• Concerns: Panic over possibly overspending, especially if one spouse passes.
• Jill & Mark’s Analysis:
  • Mark: "If they're getting $90k from Social Security and only taking another $30k out of their nest egg, which is doable… it's about a million dollars. It's not the worst thing in the world." (12:10)
  • Jill: Cautions it's sustainable unless one spouse dies and Social Security drops. "To me, it’s not about the today. It is about the survivor." (12:27)
  • Suggests couple discusses trade-off between enjoying life now vs. preserving more for the survivor.

5. What To Do With Old 403(b) Accounts?

(Starts at 14:00)

• Listener Amy: Husband has two old TIAA 403(b)s, solid performance (13% last year); mid-40s, not planning to retire for 20 years.
• Jill's Take:
  • Advises leaving the accounts at TIAA, supporting their structure and balance: "I like TIAA. I think it’s a good company. Well run." (14:12)
  • Amy should check their allocation, consider being a touch more aggressive, but moving isn’t necessary.

6. Best Investments for Grandkids (Without a 529)?

(Starts at 15:00)

• Listener Mary: Wants to leave money for grandkids, prefers not to use 529s, has trusts for kids, small whole life insurance, and some I bonds.
• Jill's Suggestion:
  • Recommends custodial brokerage accounts: "Just open a brokerage account and call it a day." (15:45)
  • Cautions that whole life insurance may not be the most effective method for the grown kids.

7. Should There Be More Expert Guests?

(Starts at 16:45)

• Listener Teresa loved the Diane Swonk episode and asks for more economics/market guests.
• Jill & Mark’s Reflection:
  • Mark: "Depends on the guest. We can’t like… we don’t like to do them just to do them." (16:48)
  • Jill: "When we have a great one, yeah, we’re good." (16:52)
  • Encourages listeners to submit suggestions for future guests.

Notable Quotes & Memorable Moments

• On consolidation:
  “If you are getting a pitch from an investment advisor to combine everything and you’re comfortable doing it yourself, you say no thank you, I’ll do it myself.” – Jill (05:00)
• On diversified withdrawals:
  “I think what’s more important is for you to start pulling the money out of the 401(k)—that’s the ticking time bomb…” – Jill (06:04)
• On being ‘late’ to investing:
  “Stop judging this gang. You are where you are. I hate that. You’re not late.” – Jill (07:28)
• On sustaining retirement spending:
  “To me, it’s not about the today. It is about the survivor.” – Jill (12:27)
• On expert guests:
  “Depends on the guest… we don’t like to do them just to do them.” – Mark (16:48)

Timestamps for Key Segments

• [03:00] – Should I combine my 401(k)s when retiring?
• [05:30] – Retirement withdrawal strategy with concentrated stock positions
• [07:00] – Investing “late” in a taxable brokerage account and diversification advice
• [11:30] – Are we spending too much in retirement?
• [14:00] – What to do with old 403(b)s at TIAA?
• [15:00] – Best alternatives to 529 plans for grandkids
• [16:45] – Listener feedback: More guests vs. listener Q&A

Episode Tone & Takeaways

Jill maintains her signature blend of practicality, warmth, and humor—never hesitating to set listeners at ease or offer a gentle reality check. Mark and Jill banter throughout, making financial topics accessible and relatable. The advice is grounded in simplicity—favoring consolidation, diversification, low fees, straightforward estate planning, and self-direction when possible. The episode closes with an invitation for listeners to shape future content, continuing the show’s deep focus on community engagement.