Roth or Not?

Summary

Podcast Summary: Jill on Money with Jill Schlesinger Episode: Roth or Not?
Date: June 3, 2026

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Episode Overview

In this episode, host Jill Schlesinger, CFP®, addresses listener questions on some of the trickiest retirement and investment decisions, with a particular focus on whether or not to use Roth IRAs. Joined by frequent contributor Mark, she analyzes real-life financial scenarios involving Roth conversions, retirement income strategies, annuities, and housing decisions. The episode stands out for its plain-spoken, direct advice, Jill’s characteristic humor, and her dedication to actionable guidance.

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Key Discussion Points and Insights

1. To Roth or Not: Timing Roth Conversions

• [04:00] Listener Scenario:
  A couple (54 and 58, both federal employees, combined income ~$376,000, $1.5M in traditional IRAs, $100K in savings) asks if they should start Roth contributions/conversions now or wait until retirement, given they’re at their peak earnings and expect to be in the highest tax bracket of their lives. The listener is also concerned about funding a $200K house renovation.

• Jill’s Response:

  • “You don’t need to use Roth now. That’s not necessary.” [04:26]
  • Since they're in the 24% tax bracket and still earning, Jill recommends not starting a Roth conversion at this very high income level.
  • Advises to concentrate on saving cash for the renovation, rather than borrowing or withdrawing from retirement accounts: “Maybe pause to fund the renovations.” [05:44]
  • If they’re working for many more years, partial Roth contributions or Roth 401(k) could make sense, but only if they’re not sacrificing emergency savings or renovation savings.

• Mark adds: If they're working for several more years, starting Roth contributions now could be beneficial, but only alongside savings for the renovation.

2. Investing for Heirs: Roth for the Next Generation

• [06:45] Listener Scenario:
  Leslie plans to fully convert a $365,000 pre-tax IRA to Roth over the next three years for her kids’ inheritance. How should she invest for long-term growth?

• Advice:
  Jill: “We are investing not for Leslie’s future retirement, we are basically have like a 30, 40, 50 year timeline, Mark.” [07:16]

  • For long horizons like this, primarily stocks—US, international, some commodities if desired. Only add bonds if heirs might need the money in 10 years or less.
  • “Pedal to the metal!” – Mark, emphasizing aggressive allocation works for such extended timeframes ([08:19]).

3. Retirement Plan Provider Dilemma: TIAA CREF vs. Fidelity

• [08:20] Listener Scenario:
  Roger, with $4.5M in pre-tax retirement accounts at TIAA CREF, is considering moving to Fidelity since his company now offers it. He details high monthly expenses, a mortgage at 6% interest (due 2036), and retirement in 2031.

• Jill & Mark’s Take:

  • No need to refinance or pay off the mortgage if planning to move before the note is due.
  • TIAA CREF is a solid institution; switching to Fidelity mostly means “you’ll have more investment choices.”
  • “It depends. Do you want more of like a brokerage option?... To me, they’re good [at TIAA].” – Jill [10:05]
  • Mark: No shade at Principal, but “TIAA is good.” ([10:18])

4. What To Do With an Old Variable Annuity

• [10:25] Listener Scenario:
  Lee has a variable annuity funded with an excess 401(k) contribution, grown from $16K to $140K, set to annuitize at 65 (in 2027). What are the options?

• Jill’s Advice:

  • Check with the provider on tax status (qualified vs. nonqualified).
  • “If you don’t need the money at all, I don’t know why you would annuitize it.”
  • See if it can be rolled into a Roth, non-deductible IRA, or IRA rollover, depending on its tax status.
  • “I would not do the annuitization. I just wouldn’t.” ([11:37])

5. Timing Social Security: Early or Wait?

• [11:45] Listener Scenario:
  Jerry and spouse, retired since 2019 with $800K in retirement savings, ask whether to start Social Security now or wait until age 70.

• Advice:

  • “If you can afford to wait, we really would like you to wait. That’s the deal.” – Jill [12:04]
  • Waiting leads to higher benefits, and “that Social Security benefit is indexed for inflation.” – Mark [12:14]

6. Buffered Annuities: Do You Need One?

• [12:34] Listener Scenario:
  Betty, 65, is offered a registered index-linked deferred annuity (buffered annuity) by her advisor. She has a pension, cash bridge to age 70, an existing annuity, $800K in retirement accounts, and a paid-off house.

• Jill’s Strong View:

  • “This is a terrible idea, and I’ll tell you why. You have a pension. You have cash. You do not need to lock up your money.” [13:31]
  • Advises: “Say no thank you,” and “start shopping for a new advisor.”
  • “There’s absolutely no reason to do this... This does not seem to be a – I would say no to this product, and I might interview a new financial advisor.” [13:49]
  • Only time a buffered annuity could make sense is if someone truly needs more guaranteed income for living expenses—but Betty does not.

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Notable Quotes & Memorable Moments

• On Roth timing:
  “You don’t need to use Roth now. That’s not necessary.” – Jill [04:26]
• On inheritance asset allocation:
  “Pedal to the metal.” – Mark [08:19]
• On annuity product pitches:
  “This is a terrible idea... start shopping for a new advisor.” – Jill [13:31, 13:49]
• On TIAA CREF vs. Fidelity:
  “TIAA is good and it’s cheap.” – Jill [10:25]

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Timestamps for Important Segments

• [03:21] Ed Slott photo anecdote and upcoming webinar
• [04:00] Main “Roth or Not” question
• [06:45] Long-term investment strategies for Roth IRAs and inheritance
• [08:20] TIAA CREF vs. Fidelity discussion
• [10:25] Navigating old annuities and rollover options
• [11:45] Social Security claiming age advice
• [12:34] Critical view of buffered annuities
• [13:49] Jill’s broader reflection on annuity product recommendations

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Flow & Tone

Jill maintains her signature direct, warm, and sometimes playful tone throughout. She emphasizes practical, customized solutions and doesn't shy away from calling out poor product recommendations, especially in the annuity space. Regular references to real-life numbers and scenarios make the advice highly relatable.

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Conclusion
In this “Roth or Not?” episode, Jill Schlesinger cuts through the noise on retirement strategies, taxes, and investment product sales pitches, giving clear, candid, and highly actionable advice for listeners at various stages of their financial journey.

Transcript

[A]

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[B]

The Ed Slott photo reminds me of a character from the Godfather.

[A]

He's like the Jewish godfather, as if like the consigliere, but like the one who's like the. The numbers guy. Anyway, Heather Shriver is amazing. She is a Social Security expert. We call her the Social Security Queen. She will be on with us for our next webinar, Wednesday, June 17th at 7 Eastern Time. But you must be a member of Jill on Money Live, which will cost you 45 bucks. I tell you something, 45 bucks. Fantastic deal. That's your annual membership. If you want to buy the individual webinar, It'll cost you 15 bucks. Do the whole thing. Come on. All right, gang, we got to do some emails right now because they're piling up. Yan writes, too Roth or not too Roth? That is the question. We are 54 and 58, both federal employees. Our income is 178,000 and 198,000. Each of us has $750,000 in traditional IRA, no Roth, 100 grand in savings, staggered CDs, no investment account, both kids are launched mortgage 3.5%. It feels like we're at the peak of our earning and likely the highest tax bracket in our lives. Does it make sense to start a Roth now or wait until we retire to do the conversion? Also, we do live in a very old house. It needs an update. House is worth $1.1 million. I doubt it would sell at that in its current status. We have $330,000 left on our mortgage. How can we fund our major upgrade? I think it will cost about 200 grand. Okay, you don't need to use Roth now. That's that's not necessary. But here, here's the thing. You are going to be in a high tax bracket as you retire, but it doesn't mean you have to do anything now. And you didn't mention when you would retire. But I'd wait, I really would because, you know, if 1, 10, 2, 3, you know, they're at 400ish right now, Mark. And so I think that puts them in 24%. So I wouldn't necessarily do that now. I wouldn't even. I'm not sure that I would put away money in a pre tax account. Maybe what you should do is right now while you're both working you is to put some more money away to do these renovations. I don't know, could be worth it.

[B]

Do they say when they want to retire? They don't.

[A]

No, they do.

[B]

I mean if they're going to be working for the foreseeable future, I don't know. But if they are, yes, maybe pause to fund the renovations. But I would actually use the Roth. If they're going to be working for several more years.

[A]

Yeah, I don't know. I don't know if they're ready to rock and roll or not. So let's presume. Okay, let's give you two different things. If you're going to work for like till you're 60, both of you 50, let's say you're 54 and 58, you're going to work till you're 62, you know, and 58, 59, if that's the case and you're going to work for a few more years, I would take some of the money and put in Roth and I would actually start saving money to pay for the renovation. When you're really ready to renovate, even if you don't want to do it this second, it's possible you just take some withdrawals from your retirement accounts and use that for the renovation. But I'd love it if you could. I just think it would be great if you could start saving some money for that. Right now that's just me. And presumably with federal employees, they'll get big pensions. But get back in touch with us because it may be that there's a few little. There may be ways to take that money out. I wouldn't necessarily borrow to do that. A $200,000 renovation. So that's that. Okay. Leslie has a pre tax IRA, $365,000. She writes, over the next three years, I plan to convert this account to a Roth ira. After the conversion, I plan to leave the Roth account to be inherited by my kids. Both the pre tax and Roth IRAs are at Schwab. How do you think I should invest this money for long term growth? What a great question. So I want to just say that when you are investing for yourself if you might have a very different outlook. But here we have. I don't know how old the kids are, but let's just pretend that Leslie has kids who are in their 20s and 30s. They've got. Now they're. We are investing not for Leslie's future retirement. We are basically have like a 30, 40, 50 year timeline, mark. Younger children, how to invest long term growth.

[B]

Yeah, if this is strictly for the kids, yeah. 100, 100% stocks.

[A]

100% maybe 80, 20.

[B]

No, if this is for them and they're not going to need it. I don't know the exact timeline here, but if it's decades in the future, I'm all in on stocks.

[A]

So some stocks, some us, some international. You could throw some commodities in there if you feel in like that. Well, you know. No, Jill, they're 35 and they might need it for a house in 10 years. Then maybe throw a few bonds like a bond fund or two. That's it. Very easy. Don't freak. Get back in touch with us. If the kids are like a little bit older, that might be something that might sway us a little bit. But yeah, you can like press the, press down the accelerator. Time to go.

[B]

Pedal to the metal.

[A]

Pedal to the metal. Roger lives in Annapolis, Maryland and he says I have a lot of pre tax retirement dollars at TIAA cref in the CREF stock index funds and bonds. Okay, so should I stay with TIA CREF or move to Fidelity? My company added Fidelity and I can do a no cost swap. There are vitals for his spouse. Monthly expenses, 11 grand when 2027 rolls around, fewer vacations. La la la la la. Okay, they have. Check this out. $4.5 million in a pre tax retirement account. 100,000 for spouse. Goal was to live off my retirement. My house in Maryland is valued at $400,000. We owe $250,000 at 6% interest only due in 2036. Refi. What do you think, Mark? They plan. Oh wait, we plan to move in retirement which will be 2031. No, don't refinance if you're going to move. Don't refinance if you're going to move and don't pay it off. Just hang in there. Social Security retirement. Four grand at 67 five at 70. Spouse 67. And four. Okay, the essence of this question. First of all, Roger, you and your wife are in amazing shape. Okay? There's a ton of money, right? Don't pay off the loan, don't refinance. I like TIAA cref. I'm not sure why you want to move, but you'll have more choices. You'll have more investment choices at Fidelity. So, Mark, do you think worth a move just to expand the menu of options for investing?

[B]

I don't know. I mean, it seems like they've done pretty well. Pretty well so far.

[A]

So good at tia? I don't know. I mean, it depends. It's just like you. Do you want more of like a brokerage option? Do you want to scratch the itch of like investing in individual securities? I don't know what you want to do, but to me, they're good.

[B]

They're good. You know, no shade at like, you know, I don't know, principal. But it's not like we're talking about going from principal to Fidelity. TIA is good.

[A]

Yeah, it's good and it's cheap. So check that out. Okay, Lee writes, in Mark's words, I have won the game and I'm moving to retire soon. That's right, Mark, those are your words. Question, what do I do with a variable annuity that was funded many years ago with an excess 401k contribution? I hated getting this annuity. I felt it was the best way to defer. You know what, sometimes you make a decision based on the tax law at the time. So I wouldn't go back. Okay. It was funded with $16,000 over the years and it has grown to $140,000. I set it up at the time to annuitize at 65. It starts at in 2027. What option should I discuss with the company? Okay, so I would discuss whether you could take an excess. So I just wonder. So the excess 401k contribution is. Is this all taxable? In other words, this is not a qualified annuity. It's a non qualified. Right. Because it's an excess. Can this be rolled into a Roth? I don't know about this. So first of all, I'd ask them if I wanted to roll it over, what account would I roll it over into? That's number one. If you don't need the money at all, I don't know why you would annuitize it. I mean, I really don't. So I'd like to try to figure out like what is the tax Liability on this. Where can it roll to? Can I roll into an IRA rollover? Is it a. It? Would it be have to go into a non deductible ira. Like you need to talk to them and see how it's labeled. And then I would roll it over. I would not take a do the annuitization. I just wouldn't. Okay, Jerry, when should we take Social Security? We've been retired since 2019. We've been living off our retirement funds. We've got 800 grand in the future. Should we take Social Security now at full retirement or wait till 70? If you can afford to wait, we really would like you to wait. That's the deal. Presuming you have decent health, the money is just a lot bigger. And Mark, as we always like to say that Social Security benefit is indexed for inflation in the future. That's kind of a nice thing, you

[B]

know, you don't need it and you're healthy weight.

[A]

Betty wants to know about Buffered Annuity. I already hate this product, so. Okay, but let's just do this. Hi, Jill and Mark. First of all, I love your show and I've learned so much from you both. I listen to it religiously. We have an evangelical listenership. Mark, we are so lucky. Okay. Betty is 65 and she writes, I am about to retire in September. My husband is already retired. He will be 65. Our financial advisor wants us to put between $170,300,000 into a single premium registered index linked deferred annuity by Athene Amplify 2.0. There are.

[B]

What a mouthful.

[A]

There are fee and no fee based options that are linked to an index and there is a cap on the up and down side. I really want people to take a deep breath and be careful before they hop onto the annuity train. Okay. That's number one. So Betty even says, after listening to you, I am wary of buying this product. I have a pension. We already have an annuity which starts paying out 35 grand annually starting in September. We also have cash set aside to tie us over until 70. We have about $800,000 in retirement accounts, a paid off house and we live below our means. Once we turn on Social Security, we will have 150% of our fixed costs covered. I have not asked if there is a commission, but I assume there is. I asked about if there is a fee and she said there is no fee even though there is a fee option as well with a bigger upside. Do you have any experience with Buffered Annuities? And are they a good product? I don't think we need them, but I don't know anything about buffered annuities. Thank you so much, Betty. Okay, Betty, let's just start with two things. One is, you may not know anything about buffered annuities, but you know about your own life. This is a terrible idea, and I'll tell you why. You have a pension. You have cash. You do not need to lock up your money. There's absolutely no reason to do this. You. So the first thing I would do is say, no, thank you. The second thing I would do is start shopping for a new advisor. That's what I would say. Why would we do this? If you have the income you need, and. And you could just invest in index funds that are less than that, and I feel like this is a weird. This was a weird recommendation from a financial advisor. Unless. Okay, can I give the financial advisor a possibility? Unless they said, like, we really want more income. We want it to be consistent, but they don't seem to be. Need that. They have an annuity. I don't know. This does not seem to be a. I would say no to this product, and I might interview a new financial advisor. That's a tough one. I get so nervous about these things. Like, I want to make sure that I'm just not throwing everybody under the bus. But, like, annuities are so, so difficult because they are so complicated, and it can work. I am not saying that annuities just never work. I'm just saying that, like, it's better for. In a. In a case like this, that, like, we already have the income we need, why would we tie up our money? Remember that there is, like, the whole idea that you've lost access to this money. I don't know. I just don't get it. I don't get it. I don't get it. Okay, gang, if you've got an annuity question or any other question about anything we've talked about today, get in touch with us. Go to jillonmoney.com, click the contact us button. And, of course, if you want to come on the air, check the box. Mark will do everything else. Don't forget to check out all the content that lives on our website. Mark does such a great job with that. And subscribe to our free weekly newsletter. Comes out on Fridays. You can subscribe to us on the Odyssey app or wherever you find your favorite podcast. Try to lift someone up. Change your work, change your wealth, change your life. Thank you for listening. And we'll talk to you tomorrow. Are you really buying a car online on Autotrader right now? Really? At a playground? Yeah. Really? Look at these listings from dealers. Wow, your search can really get that specific. Really? And you just put in your info and boom, car's in your budget. Mom needs a second. Honey, you can really have it delivered. Really? Or I can pick it up at the dealership. One sec, sweetie. Mommy's buying a car. Mommy, I think your kid is walking up the slide. Kyle. Again? Really? Autotrader? Buy your car online? Really? Hi, this is Jill Schlesinger, CBS News business analyst, certified financial planner, and the host of the Jill on Money podcast. Beginning, middle, or end of the year, it's always a great, great time to take control of your financial life. And the Jill on Money podcast is here to help. Your questions make it possible for me to provide unconventional and entertaining insights on your money and, more importantly, on your life. Follow and listen to Jill on Money wherever you get your podcasts.