Is Investing a Pipe Dream?

Summary

Podcast Summary:

Jill on Money with Jill Schlesinger — "Is Investing a Pipe Dream?"
Date: February 6, 2026 | Host: Jill Schlesinger

Overview

In this episode, Jill Schlesinger dives deep into the question: Is investing a pipe dream for the average American? Responding to a thoughtful listener email, Jill and producer Mark unpack the unique challenges and anxieties that so many people face when considering investing, especially those outside the country’s wealthiest circles. Through listener stories and practical advice, they demonstrate the core principles—and myths—of investing, the hurdles faced by everyday Americans, and the importance of starting early, regardless of the amount.

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Key Discussion Points & Insights

1. Are Most People Shut Out of Investing?

• Listener Email ("Double K") frames the episode: Expresses concern that average Americans don’t relate to financial advice aimed at the wealthy, asking, “Is there any hope for hardworking, taxpaying Americans who love this country but feel like investing is a pipe dream?”
• Jill’s Perspective:
  • Acknowledges financial inequality and how “most recently, we’ve been hearing from a lot of those people who have a very low cost of living… they are able to realize their retirement goals” (05:53).
  • Emphasizes that retiring early (e.g., at 53/55) typically requires stable pensions or unusually strong finances.
  • “I don’t think it’s 75% [that can’t invest], but… the top 20% are doing fine. The bottom 20–30% are going to rely on social safety nets… everyone in the middle… the choices you make in life… you make different choices” (06:37).

2. Starting Early Is Key—Regardless of Amount

• Mark’s Take:
  • “A lot of times, people… weren’t making a gazillion dollars… but they all started saving early. Even if it was just a hundred bucks a paycheck…” (07:09).
  • Compound interest only works if you “start early.”
• Jill:
  • “If you’re really struggling and you want to know how to start investing, we’re happy to hold your hand… For most people, it’s putting money into a retirement plan. Getting started early and a little bit at a time.” (07:35)

3. Real-Life Listener Scenarios

• Anne, a New Divorcee with $400k–$500k Windfall:

  • Has two teens, $20k credit card debt, $60k salary, and no other assets.
  • Jill’s Step-by-Step Advice:
    • Pay off the $20k debt.
    • Save 6–12 months of expenses in a high-yield savings account.
    • Max out the Roth IRA for the year.
    • Use employer retirement plans if offered.
    • “Would not buy a home… You should rent and run your cash flow and see…” (09:44)

• Ken’s Silver Investment for Grandkids:

  • “No, that is not a long-term retirement vehicle… Put the money in a 529 plan, let's call it a day…” (10:28)

• Stephanie, Disabled and Needing 529 Funds for Herself:

  • Can withdraw with penalty/taxes—“Call [the plan], tell them the exact situation… you'll pay a few bucks. You'll get the money out. Boom, done.” (11:30)

• Kathy, 73 and First Year RMD Withdrawal:

  • Yes, you will owe tax on your 401(k) withdrawal, likely around 12% if single. (13:00)

• Tressa, 69, Worried About Market Fluctuations:

  • Wants to keep more cash in the bank for emergencies, temped to pay off the house.
  • Jill: “No, no, please, Tressa… Keep some money in cash… but please don’t take that [retirement] money out… that's your safety net.” (15:04)

• Ann, 75, With Substantial Investments and CDs:

  • $3M brokerage, $1.4M Roth, $300k laddered CDs; wants to know if CDs count as emergency reserves and whether to move them into investments.
  • Jill & Mark: “If it makes you feel good, let it be… Put your little head down on that CD pillow and relax. Get some sleep. It’s all good.” (17:31)

4. Meta-Discussion: Email vs. Live Call-In Episodes

• A Listener Critique: "The email shows stink. I love listening to when people are live." (18:23)
• Jill’s Response:
  • Defends the value and importance of email shows: “Do not stink. I find that very offensive.” (18:30)
  • Explains the show’s origin and volume of emails: “We have 4,054 [in the inbox]…” (19:50)
  • “This is a two-person band… Mark does so much…” (20:03)

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Notable Quotes & Memorable Moments

• Jill on Relatable Advice:
  • “If you're out there and you feel like you're struggling, you're probably not listening to this podcast. There is a funnel… we are appealing to people who probably have a few bucks and are interested in their finances.” (07:30)
• Jill on Starting Small:
  • “For most people, it’s putting money into a retirement plan. Getting started early and a little bit at a time.” (07:35)
• Mark on Early Habits:
  • “It’s always a common theme… they all started saving early. Once you do that… compound interest kicks into gear.” (07:20)
• Jill on Security vs. Returns:
  • “If it makes you feel good, then let it be… Put your little head down on that CD pillow and relax.” (17:31)
• Jill on Listener Criticism:
  • “Do not stink. I find that very offensive… We did it based on emails because everyone was freaking out during the pandemic, remember?” (18:30)
• Jill’s Signature Tone:
  • Direct, practical, never sugar-coating, and always with a slight wink—“Let her have her nice, fluffy CD.” (17:40)

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Timestamps for Key Segments

• 03:37 — Start of main listener question about investing as a pipe dream
• 07:09 — Mark emphasizes saving early, even in small amounts
• 07:35 — Jill’s starter advice for people new to investing
• 08:45–10:20 — Case study: Anne’s post-divorce finances and actionable steps
• 10:26 — Quick take on investing in silver for grandkids
• 11:20 — How to withdraw from a 529 when circumstances change
• 13:00 — Tax implications of RMDs from retirement accounts
• 15:04 — Jill’s take on managing cash vs. investments in retirement
• 17:31 — Discussion on keeping funds in CDs for peace of mind
• 18:23 — Jill & Mark discuss listener feedback and the value of email episodes

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Summary

Jill Schlesinger reaffirms that investing is not a pipe dream—it's about getting started, even with modest resources and beginning small. The path to financial security may differ based on your starting point, income, and choices, but small, early efforts, measured risk, and realistic goals lay a solid groundwork. This episode offers both empathy and clarity, busts myths about investing “needing” large sums, and showcases the kind of no-nonsense, compassionate financial advice that has made Jill a trusted voice for real people trying to secure their futures.

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For questions or to join the show, visit jillonmoney.com and click Contact Us.

Transcript

[Jill]

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[Mark]

People get so hung up on that.

[Jill]

Oh yeah. And he kind of like he breaks it down. So any tax question, any Roth question, any of that, you just have to get in touch with us and join us for Jill on Money Live. Now, maybe you can't make it on the night of the 26th and you're like, but I love Ed. You can purchase that one webinar for 15 bucks. So you can find this all on the website jillonmoney.com okay. This is from Double K, who says in the subject the majority of those wanting to retire don't see light at the end of the tunnel. Jill, thank you for doing what you do. My husband and I, both baby boomers, took early outs at 53 and 55 when it was offered because how much is enough? We needed to assist many close relatives. Unfortunately, at the end of their lives. We honestly felt the way it all just fell into place. It was meant to be. Fortunately, we had both have pensions and Social Security and had nice investments. However, the last 20 years or so of retirement have seen many ups and downs in the economy. Luckily, we own our home and our child was through his education. We're doing fine and feel blessed every day. We also save $2,500 a month besides going on a nice small and large vacation. So we're fine. But what am I writing about? So many people in the US don't have the income or the investments that many of your listeners do. It sounds like the east and West Coast People on your show are hugely rich. What about the other 75% or more of the society? They scrape along working as many jobs as they can in hopes of paying their bills, their car and their house, food and medical insurance. When they do have extra money, how do they begin to invest correctly? Does it take 100 or 500 or $1,000 to begin? I've heard this story so often that it makes me very sad. Is there any hope for those truly hard working, taxpaying Americans who love this country but feel like investing is a pipe dream? Well, look, I know we got some rich people who listen, but sometimes we talk to people who don't have as much money and they have lives that they can afford. And in fact, Mark, I would say that most recently we've been hearing from a lot of those people who have a very low cost of living and sometimes they live in low cost of living places and they are able to realize their retirement goals. Now, I don't think anyone is going to suggest that you could retire early at 53 and 55 unless you had a pension. So lucky for you. So, you know, I think that people are chipping away. They're doing a better job. I do think the younger generation is investing earlier and more than older generations do. I don't know. I don't know how, how to, you know, make sense of what you know. I don't think it's 75%, but I do think that a lot of people who are, say the, let's call it the top 20% are doing fine. I think the bottom 20 or 30% are going to rely on the social safety nets that are in place and everyone in the middle, depending on how much money you can afford to put away and the choices you make in your life and whether you think it's important to put your kids through school or save for retirement, you make different choices. Mark, am I missing the boat?

[Mark]

You're not missing a boat. And I'll also say that a lot of times with our I'm doing air quotes, rich listeners, you know, when you get the backstory, and oftentimes we get the backstory off the air. So not all the time you guys get to hear it, but it's so it's always a common theme. You know, a lot of times people, they weren't making a gazillion dollars when they first started in their careers, but they all started saving early.

[Jill]

Early.

[Mark]

Even if it was just 100 bucks a paycheck, they all started early. And that's the key because once you do that, that's when the compound interest kicks into gear.

[Jill]

Yes, man, yes, ma', am. That's exactly right. So listen, if you're out there and you feel like you're struggling, you're probably not listening to this podcast. So let's also be clear that like there is a funnel that we are appealing to people who probably have a few bucks and are interested in their finances. But you know, if you're really struggling and you want to know how to start investing, we're happy to hold your hand and take the first step. For most people it's putting money into a retirement plan. Getting started early and a little bit at a time. All right, this is a message from Ann who writes. Hi Jill and Mark. I'm recently divorced and the home will be sold. I'm expecting to receive about 4 to $500,000 when the sale is complete. I had two teenagers, a Roth with 100 grand, 20 grand in credit card debt, no other assets, and a full time job earning $60,000 a year. Hey Double K, how about this? This is like a regular person, right? My question is what to do with the 500 grand? Pay off the debt. Should I buy a home outright? I'm pre approved for a $400,000 house. No other money coming in other than wages. No child support, no alimony. Okay, now this is a great tee up, Mark, because it helps with like the previous question, right? Okay. So Anne, number one, when you get that money, first thing you're going to do is you are going to start thinking about the big three. The big three is no consumer debt, an emergency reserve fund that can cover you for six months, maybe 12 months. And three would be putting money into a retirement account. So let's pretend you got $400,000 or let's say 500 because I like more is better for you. So we pay down your 20 and then with another 60. Let's put that in a high yield savings account right away. Just do that. Then you're going to make your contribution to your Roth IRA for this year. And I'm wondering if your full time job offers a retirement plan. If it does, then we want you to start using that. If not, I think that what we would really suggest is that you would not buy a home. That is not important. That is not a thing that you should do. You should rent and then we can run your cash flow and see how much money it will cost you to float your life. And what could be available for your own retirement? Maybe a supplemental plan. I think that buying would tie up all that equity and you lose access to it. Maybe wherever you hold your Roth ira, you could just open up an account in your own name and just kind of play it really simple like some money in the stock index, some money in a bond index, some money in a commodity index and call it a day. But I'd really like to hear a little bit more about, like, what it costs you to live your life right now before we made that decision. So, Mark, thanks for. Did you do that on purpose to, like, line that up like that?

[Mark]

That is a coinky dink.

[Jill]

Coinky dinky. Fantastic. Okay. Okay, Mark, you want to answer this? Ken wants to know, is it a good time to invest in silver for my grandkids as a long term retirement vehicle? No, that is not a long term retirement vehicle. I love it when people ask questions about something that's already gone up like 100%. It's like, would you want to do that? How about this for your grandchild? Let's just throw some money in crypto. Do me a favor, put the money in a 529 plan, let's call it a day, and that's that. Speaking of 529s, here's Stephanie, who says she's got a 529 account that would have been for her daughter for college, but now cannot be used for her. I'm 54 years old, I'm disabled and I'm single. I really need the money, but I'm not sure how to get it out. What do I need to do to get the money out? Thank you for your time and support in this matter, Mark. She pulls the money out and pays the tax, right?

[Mark]

Yeah, I mean, that's it. You're going to pay. You're going to pay a penalty. And if you've been taking state income tax deductions along the way when you were making those contributions, there may be a recapture.

[Jill]

Call them up, tell them the exact situation you just told us about, and they'll get you your money and you'll pay a few bucks. You'll get the money out. Boom. Done. Kathy writes, I'm 73 and last year withdrew my first required minimum distribution from my 401k. Will I need to pay taxes this year on the withdrawal? Yes, you will, Kathy. You absolutely will. So Kathy is retired. Her Social Security check is her only income. So think about this. You're going to have Social Security. You tally up that income, and on top of that, you will take the income from your 401k and that will be part of. I don't know if you have a spouse or not, but you'll pay it whatever rate it is. So let's pretend that you are single. You probably pay 12% tax on that. So I will hope you have some money that is available to pay any taxes. But you know what, I'm sure you're fine. So she says, oh, there's a we. So let's see. It depends kind of what your who your we is, how much weight your tax bracket is. So she says, we value your opinion. We love being able to watch you on cbs. You're the best. Thank you so much and God bless me. How about that, Mark? I like Blessed. I need it. You know, I've been binge watching Grantchester because it's on Netflix and it's like this vicar who's adorable and I do it when I do my long bike rides. I now cause on peloton, I don't know if you realize this. You do a long bike or you can use Netflix, right?

[Mark]

So. And I was checking that out. So you're listening to Netflix. So you're not getting the instructor at all?

[Jill]

No, I got my own workout. Cause I have the miraculous Samantha, my trainer, who's like programming me these crazy workouts that are very specific to my kind of training. And, and so sometimes she'll say, you can do a peloton for this. But other times she just gives me, I have a thing, an app on my, that on my phone that tells me the whole workout. This morning I did an hour and 45 minutes.

[Mark]

And it tells you the resistance and all that.

[Jill]

She doesn't. She basically it tells you the output. Right? So she. It's like what you're targeting for your output. And so I'll give you an example. So this morning, I'm sorry to digress, guys here. It's like I had like a, like a 20 minute warmup and then it was like in four steps, be in zone 1, 2, 2, 2, 3, 3, 4. And they get. She gives you like the output, you know, the 153, 135. And then she just does. So it was an hour and 45 minutes. I banged out three episodes of Grantchester. It's amazing.

[Mark]

Anyway, I tried utilizing this the other day. I wanted to watch some tennis, but then I realized, okay, I'm watching tennis. I'm no longer getting the instructor, so I need the instructor.

[Jill]

Well, you don't have any discipline.

[Mark]

I just need direction.

[Jill]

I need to be well. That's why I had the direction, so it's. It works for me. All right. Tressa says, love your advice on CBS Mornings. Oh, my God. I'm talking to the six people who watch CBS mornings. Thank God.

[Mark]

Down to three.

[Jill]

Yeah, let's. I could. Who knows? Okay, so I have money with my financial advisor's company for retirement. I'm 69. I'm curious, how much should I keep in my savings account at my bank? As opposed to keeping the emergency money inside my retirement account, which, of course, I can access as needed in my checking account. I keep money for a house payment and all other bills. I drive a 2009 car. I've got no debt. I worry about the markets taking a dive, a dump, not having cash easily available. This seems to be a constant worry for me, and I'm tempted to pay my house off, too. No, no, please, please, Tressa. No, no, no, no, no. Okay, here's the thing. That retirement money is your slush fund. Okay? I get that you hate debt, but. But if you're really worried about markets, just free up some more money so that you have two years of your actual expenses safely set aside, either in a high yield savings account at your bank, or you can do it in, you know, in some other way. But like, keep some money in cash. Then let's tell your financial advisor that you're really worried about those ups and downs and make sure that that person is directing you in a portfolio in a retirement account that's consistent with that fear. But please don't take that money out. Please don't, because it's truly going to be loss of that safety net that you might need. So, you know, she had put down 200 grand in cash and owes 130. So, no, please trust us. We want you to have access to your money always. All right, last one for today, Mark. Ann writes, should I convert CD investments to brokerage and stock investments? Here are the details from ann, who is 75, and she says, My husband is 79. We're retired. We've saved all of our lives. We've got $3 million in a brokerage account, 1.4 in Roths, 300 grand in various CDs, which do mature at different times. I like that. That's like the laddered approach. Okay, so the question is, can these serve as our emergency reserve funds if needed? Yes, absolutely. Let me read a little bit more of the background. Our house and car paid for. Our pensions, cover our expenses. Last year, we brought in $120,000. We spent 118,000, which included two special vacations, of course. Mark, she knew that you would want to know. One was a safari in Tanzania and another to Egypt. So cool. I love that. She does say, I don't think we're going to be traveling like that in the future. Aging is such a bummer. So we will probably have extra money in the future. I want to know, is it wise to keep that money in CDs or wiser to invest in the brokerage account? Note, I do like the feeling of security the CDs give me. I don't have so many years to wait for a comeback. If a recession hits, the market dumps. But of course, the returns in the markets are greater. What do you think?

[Mark]

And she doesn't have to wait for a comeback. Pensions cover the expenses.

[Jill]

I mean, first of all, if it makes you feel good, then let it be.

[Mark]

Who cares?

[Jill]

Come on, no pressure.

[Mark]

Unless you want to, like, invest it for your kids or something.

[Jill]

Now let her. Let her have her nice, fluffy CD.

[Mark]

$3 million in a brokerage account.

[Jill]

It's pretty nice, huh?

[Mark]

One and a half in Roth.

[Jill]

So, yeah, I wonder what they did, you know, and they have pensions for a long time. They save for a long time. 75 and 78. Put your little head down on that CD pillow and relax. Get some sleep. It's all good. You don't have to worry. All right, that's it. Hey, a Friday. And we did emails. I love it. You know, sometimes I do like the emails, Mark, although you must get so sick of hearing my voice.

[Mark]

Somebody wrote in.

[Jill]

Was it mean? Don't you dare tell me if it's mean.

[Mark]

I mean, who cares? Like, you know, you're never going to please them all. Who cares?

[Jill]

All right, what do you write?

[Mark]

Oh, here. This was on YouTube. You left a comment. No offense, but the email shows stink. I love listening to when people are alive.

[Jill]

Well, then everybody has to just be. The email show. Do not stink. I find that very offensive.

[Mark]

That was. That was Chris on YouTube.

[Jill]

Hey, Chris, go to the next show. How about that? I don't know. Like, if everybody hates the email episodes, it's hard because then you people write emails that this is how the show began. We did it based on emails because everyone was freaking out during the pandemic, remember?

[Mark]

It's just that the conversations with people are so good that the emails shows kind of feel like a little bit of a letdown. So I get it. But, you know, we got to do them because some people are shy and they don't want to come on.

[Jill]

Yeah, and we want to answer their questions. And I'm not going to do. I'm not answering emails all day long because I do have another job. Sorry, dude. Stink. What a nice. If you met me face to face, would you say that?

[Mark]

See that, Chris? This will bother Jill. It does.

[Jill]

So mad right now.

[Mark]

It does not bother me at all, Chris.

[Jill]

I have a lot of. I have a lot of feelings right now. I only wish you were on the air with me, truly. Why don't you guys step in my shoes? Chris, Got a very big life that I'm managing here.

[Mark]

Oh, boy.

[Jill]

Oh, brother. Thanks, Dingbat. Thank you. All right. I love hearing from you when it's good. No, I can take it. I know. I like the conversations also. We just. We have. So, Mark, how many emails do we have right now?

[Mark]

The email inbox. Oh, it's almost a very round number. 4054.

[Jill]

4000 emails that we haven't answered. And we always will ask whether or not you want to join us on the air live. It's very difficult. Okay. We really do want to try to work with all of you.

[Mark]

This is a two person band.

[Jill]

Exactly. I don't have. You know, you listen to those podcasts and they have like 17 people they're thanking at the end. Jeez. I mean, it's us, just the two of us. And Mark does so much for me. That is not just show. It's this show. It's Money Watch, it's Jill on Money Radio. It's managing the website, it's managing my social media. Yeah, I don't see your nasty remarks on social media because Mark kicked me off. I don't even know how to get to my friends on LinkedIn because I'm like, did he change the. The password? I can't even go there. People send me reels and stuff. Mark. I have no idea. I'm like, oh, boy, I wish I knew my Instagram sign. And Mark knows that I don't. So when you're sending any nasty grams, Mark is filtering it out for me because I'm so thin skinned.

[Mark]

You really are.

[Jill]

I know. Don't you love me for that? It's because I care. All right? I do care. And I so grateful for you guys for listening. And I'm sorry if you don't love your email episodes. I think they're kind of fun sometimes. All right, if you would like to get in touch with us, go to Jill on money dot com. Click the Contact Us button. Write us a note if you want to come on the air. Check the box. Mark does chase down anybody who says they want to come on the air, so it's a lot of work for him. And that's part of the process here. So the more of you that say you'll come on the air, you can change your name, you can change where you're living. We'll protect you. Don't worry. But we do love to talk to you live. And it is more fun. And I get it. I do. So I want to try to satisfy everybody. And we are still always just so grateful that you hang out with us every day, Monday through Friday. Okay. Subscribe to us on the Odyssey app or wherever you find your favorite podcasts. Leave us a rating and review wherever you listen, but only good ratings and only good reviews. Our music is composed by. She's kidding. A little bit, sort of. Our music is composed by Joel Goodman. Mark Teleso is the very best executive producer in the world, and he also has managed to become the web king. We are distributed by the lovely folks at Odyssey. We ask that you lift someone up. Change your work, change your wealth, change your life. Thank you for listening. We'll talk to you on Monday.

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