I Got a Late Start, Am I Okay for Retirement?

Summary

Podcast Summary: Jill on Money – "I Got a Late Start, Am I Okay for Retirement?"

Episode Date: February 11, 2026
Host: Jill Schlesinger, CFP®
Guest Caller: Katherine from Connecticut

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Episode Overview

In this episode, Jill Schlesinger takes a listener call from Katherine, a 58-year-old single professional who started investing for retirement late (mid-40s) and seeks reassurance about her financial path. The conversation delves into Katherine’s finances, future plans (including property sale), investment strategy, and lifestyle questions, providing actionable advice and reassurance for late starters to retirement savings.

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Key Discussion Points & Insights

1. Katherine’s Financial Snapshot

[03:46–08:08]

• Age & Status: 58, single, no children, happy renter
• Earnings: ~$250,000/year (variable due to self-employment/business moves)
• Retirement Savings:
  • $333,000 in 401(k) (of which $32,000 is Roth)
  • $21,000 in IRA
• Brokerage Account: $1.1 million, mainly in stocks
• High-Yield Savings/CDs: $300,000 (aiming to reduce to $200,000 as not all needed for liquidity)
• Real Estate Outside US: Worth $1.3 million after taxes, to be sold within the year
• Monthly Spending: ~$6,000

Jill [07:06]: “That’s incredible. Good for you. Is it all in stocks? ... All right, so that’s it. So I just want to make sure we got everything.”

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2. Retirement Planning & Concerns

[08:42–09:41]

• Katherine says she enjoys her work but has health considerations; she wants to work full-time until 65 and then part-time into her 70s, if possible.
• Her primary worry: Having started retirement savings late, is she truly “okay” for retirement, despite assurances from her financial advisor?

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3. Jill and Mark’s Analysis: “This is a Layup”

[09:41–11:19]

• Mark (Producer/Co-host, CFP®): Confirms Katherine is in very strong financial shape, echoing her advisor’s reassurance.
• Jill: Affirms that Katherine’s spending is reasonable and her assets are significant, especially factoring in her brokerage account and upcoming real estate sale.

Jill [09:57]: “The amount of money that you have saved, even though you got a late start, is awesome... You don’t spend a ton of money. So this is a really amazing story. I don’t think there’s any problem with the plan.”

Mark [10:10]: “Is this a slam dunk or a layup, which is easier? I say a layup.”

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4. Investment Strategy Going Forward

[11:19–12:25]

• Asset Sale: Jill recommends, when real estate proceeds arrive, that Katherine adjusts to a more diversified (less aggressive) portfolio, adding bonds and dialing back stock exposure.
• Advisory Fee: Jill encourages Katherine to negotiate for a lower advisor fee due to her increased assets.

Jill [11:40]: “You don’t have to be 100% stocks anymore. You’ve already gotten like the greatest benefit... When you add [the] new money, you should get your fee lowered; you should talk to the advisor and say, ‘Okay, I want to take less risk. I want to do something that’s a little bit less edgy, maybe add some bonds…’”

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5. Estate Planning & Lifestyle Spending

[12:25–13:15]

• Estate Documents: Thanks to Jill’s prior advice, Katherine has her paperwork in order and will leave her assets to extended family (not just her cat).
• Travel Wishes: Katherine wonders if she can afford to travel more, given her health has prevented it in the past.
• Jill’s Response: Full approval! Even annual $10–15,000 travel is manageable within her plan; “Fly business class!”

Katherine [13:08]: “If I were to spend more money on traveling—”

Jill [13:10]: “Not gonna be a problem... Go business class. Really, come on. I think you’re in great shape.”

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6. Encouragement for Late Starters

[13:15–14:00]

• Jill emphasizes that Katherine’s story shows one can get a late start and still end up in a strong position—especially if focused, with modest spending and by making investments work for them.

Jill [13:33]: “Everybody listening, you can get a late start and still be in great shape. So please, go off, enjoy yourself, and don’t worry about retirement.”

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Notable Quotes & Memorable Moments

• On Financial Anxiety:

  “Before you start judging yourself, we all have emotions around money and it’s very important to at least just acknowledge that.”
  — Jill [01:07]

• On Late Starts:

  “You can get a late start and still be in great shape... Don’t worry about retirement. Late start, worried about retirement is the name of the [episode]. And she doesn’t even want to retire—she wants to keep working.” — Jill [13:33]

• On Investment Adjustments:

  “You don’t have to be 100% stocks anymore. ... You should talk to the advisor and say, ‘I want to take less risk.’ ... Maybe add some bonds, do something less edgy.” — Jill [11:40]

• On Enjoying Life:

  “Go business class. Really, come on. I think you’re in great shape.”
  — Jill [13:16]

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Segment Timestamps

| Segment | Timestamp | |------------------------------------------------------|--------------| | Katherine introduces her financial situation | 03:46–08:08 | | Jill and Mark analyze the financial picture | 08:42–11:19 | | Advice on investment, risk, and advisory fees | 11:19–12:25 | | Discussion of estate planning and travel spending | 12:25–13:15 | | Broader encouragement to late starters | 13:15–14:00 |

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Takeaways for Listeners

• Starting late with retirement savings isn’t a dealbreaker—focus, high savings rates, and discipline can yield impressive results even in a compressed timeframe.
• Diversification and risk assessment should be revisited after major liquidity events like property sales.
• Reassess fee structures with your advisor as your assets grow.
• Quality-of-life spending (like travel) can be justified, especially if the plan is solid and well-funded.
• Estate planning isn’t just for the wealthy or for those with children—single individuals need this too.

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Tone: Encouraging, affirming, clear, and grounded in actionable guidance—Jill’s signature “no-jargon, all-heart” financial wisdom throughout.

Transcript

[Jill]

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[Katherine]

Hi, Jill and Mark. I'm so honored to get to talk to you both. I've learned so much from your show. Thank you.

[Jill]

Thank you. Oh, we are so happy to have you. We are always honored when someone comes on the air. So tell us what's up.

[Katherine]

So I just want to know if I'm doing okay for my retirement because I have a lot of worries. I started very late in my career. I started in my retirement investments in my mid-40s. And so I just have a lot of fear that I'm not doing okay. I do have a financial advisor who says I'm okay, but I just want.

[Jill]

Well, you know, they lie all the time. That's what they do. No, I'm just kidding. They don't. I understand. Just sort of like another person's ears and eyes on the situation. Another two people. And Mark and I are both certified financial planners, so we're happy to do that. So, Kathryn, you said you got a late start. How old are you now?

[Katherine]

So I just turned 58.

[Jill]

Okay. And are you married, single, partnered?

[Katherine]

I am single, no kids, one cat.

[Jill]

How much do you spend on the cat? No, I'm just kidding. Single, no kids. Okay. Okay. And you're working full time right now?

[Katherine]

Yes.

[Jill]

How much do you Earn.

[Katherine]

So last couple years it's been pretty up and down because I had to move my business and as expected, I lost a lot. But I think we're on track to be steady. I would say like 250.

[Jill]

Wow. Okay, that's great. Now you're putting money into retirement, right? Yes.

[Katherine]

So I started in my late 40s.

[Jill]

Okay. And how much are you contributing to retirement? Maximum, maximum. And with that catch up contribution because you're over 50. Okay. So you max out retirement. Is it a traditional account that you're using? Okay. How much money is in your traditional retirement account?

[Katherine]

Well, so in my 401.

[Jill]

Yep.

[Katherine]

I have 333,000.

[Jill]

Uhhuh.

[Katherine]

And 32,000 is Roth.

[Jill]

Okay. Of the 333.

[Katherine]

Of the 333.

[Jill]

Okay. So we'll say 300 and then we'll say. Okay, got it. What else is out there in terms of investment?

[Katherine]

So I have an IRA with 21,000.

[Jill]

Okay.

[Katherine]

And then I have my savings, mostly high interest savings and CDs are about 300k.

[Jill]

Wow, that's a lot.

[Katherine]

I was stockpiling because of the move, but I don't really need all that much. I'd like to be maybe at 200.

[Jill]

Fair enough. Now, do you own your home or do you rent?

[Katherine]

No, I rent and I'm a very happy renter. I don't have to worry about maintenance and with all the snow. Snow shoveling.

[Jill]

Oh my gosh.

[Katherine]

And I really love where I live. It's a nice neighborhood and everything.

[Jill]

Wonderful. So what do your expenses look like?

[Katherine]

Yeah, I also have some non retirement.

[Jill]

Oh, tell. I forgot. Thank you for piping in so brokerage account.

[Katherine]

Yeah, so most. So I did before I knew what I was doing. Like I did had everything in a low interest savings for like a long time until I figured out that there was such a thing as investment. So I have about like 1.1 in there.

[Jill]

That's incredible. Good for you. Is it all in stocks?

[Katherine]

Mostly? Yeah. Yeah.

[Jill]

Okay. All right. So that's it. So I just want to make sure we got everything.

[Katherine]

We have one more thing.

[Jill]

What do you got?

[Katherine]

So I do own real estate abroad.

[Jill]

Oh, is that something you get rent from?

[Katherine]

Yeah, it's not rental. The value is in the property itself.

[Jill]

How much is it worth?

[Katherine]

And so it's hard to say exactly because the taxes are so high. So I'll probably be taxed about 50% when I cash out. So I think conservatively it's about 1.3.

[Jill]

Wow. And it's something that you would sell eventually or you would.

[Katherine]

No, pretty. Probably within the year.

[Jill]

Oh, yeah. How did you come upon this property?

[Katherine]

Yeah, I had some help investing in it, and then it more than doubled in just a few years.

[Jill]

Oh, my God. So you're saying that it would sell for 1.3 and then it would be.

[Katherine]

No, that's after taxes.

[Jill]

So that is the net what you think you would have. So now we're talking about eventually, like in the. Let's say in the next couple years.

[Katherine]

Probably within the next year.

[Jill]

All right, I like that. Within the next year, you'll have $2.4 million in brokerage. Right. Because you'll have the cash out of the property abroad. Added to your 1.1 million, you've got your 300 grand that's in savings and your high yield. You got your, you know, your 330 something in traditional or almost 350 in all retirement accounts. Mostly traditional.

[Katherine]

Right.

[Jill]

So that's incredible. What do you think you spend on a monthly basis?

[Katherine]

Like around six.

[Jill]

Wow. Okay. 6,000. And how long do you think when we talk about retirement, you're worried about retirement? How long do you think it will be before you actually can retire, just like emotionally, not like financially?

[Katherine]

Well, that's kind of a big question because I started so late in my career and everything. I had a lot of health issues that I was trying to overcome. So I finally got my health stabilized. And so I absolutely love my job. I mean, I love it so much. And if I could, I would just keep working. But it is a strain on my health, too. So that's one concern. My plan is I want to work full time until 65 and then part time until into my 70s if I can. That's what I would love to do.

[Jill]

Amazing. Mark, I think that you're going to chime in here and tell me that things look pretty darn good for Katherine so that you might agree with her advisor that she's probably just fine for retirement. Do you agree with that, Mark? Yeah, I was just trying to decide, is this a slam dunk or a layup, which is easier? I say a layup. This is a layup. Like, I mean, for a variety of reasons, the amount of money that you have saved, even though you got a late start, is awesome. Which is why when Mark and I hear from people who are like, oh, you only talk to millionaires, because objectively, someone's going to hear this and they're like, katherine's a millionaire. But a lot of this happened because you started late. But you got very focused, obviously got your money to work. Yes. The market helped you, which is great. And you don't spend a ton of money. So this is a really amazing story. So I don't think there's any problem with the plan. The one thing that I would like to just put into your little thought bubbles is I want you to be clear that when you sell this rental property. I'm not rental property. This other property abroad, and you have that $1.3 million. I would like you to talk to your advisor about using that new money to have a more diversified brokerage account. I think that that would be much better for you as you look ahead. Meaning you don't have to be 100% stocks anymore. You've already gotten like the greatest benefit over the last five years from being a heavy duty, aggressive investor.

[Emma Greed]

You.

[Jill]

You don't have to do that anymore. If you didn't have that big chunk of money coming in from the sale of the property, I would say, let's do something today. But I mean, you do have 300 grand in cash. But when you be. Again, if you're going to the advisor and you say, I have this new money. Oh, and by the way, I don't know what your fee is right now, but you should. When you add. Before you add new money, you should get your fee lowered because you're not going to be over $2 million. Right. But you should talk to the advisor and say, okay, I want to take less risk. I want to do something that's a little bit less, A little bit less edgy. Maybe add some bonds, maybe add something that's a little bit less of the pedal to the metal. And I think that the advisor will probably agree with that, truly. And then, look, if something were to happen and it's like, I plan to work prime 65, but maybe you're like, oh, it ends up being 63 because of my health. Then you don't have to worry so much about where the market is when you make that decision.

[Katherine]

Oh, this is great. That was exactly the question I was gonna ask you about how to handle that money. So you answered it. Oh, that. That sounds like a very good idea.

[Jill]

Excellent. Now you are single. Are you gonna leave your cat all the money? Do you have estate documents?

[Katherine]

Because of you, I do, yes. I have lots of nieces and nephews and everything. So I have done that because of you.

[Jill]

Oh, I am so grateful about that. I really am. Because, you know, it's weird. Like, you have a bun and like you want it to go one versus the other or something. You have, you have ideas about what you want to happen, obviously. So I think that's great. I'm very happy about that.

[Katherine]

Can I ask one more thing though? Would it be okay if I, because of my health, like, I haven't been able to travel much, which is something I really love to do. If I were to spend more money on traveling.

[Jill]

How much? I mean, if you said to me every year you're going to take a 10 or $15,000 trip, not gonna be a problem.

[Katherine]

Oh, I don't even need that much.

[Jill]

But okay, yeah, go business class. Go business class. Yeah, fly business class. Really? Come on. I think you're in great shape and everybody listening. You can get a late start and still be in great shape. So please go off, enjoy yourself and don't worry about retirement. You know, late start, worried about retirement is the name of the. And she doesn't even want to retire. She wants to keep working. I don't.

[Katherine]

I want to keep working. I love my work.

[Jill]

That's so, that's so great. So listen, good luck, keep us posted. Send us a picture when you take that first trip and stay in touch if you need anything else. So if you are like Catherine and you got a late start but you don't have millions of dollars, that's okay too. Why don't you get in touch with us? And by the way, maybe you have an adult child who's getting a late start and they need some hand holding. We can help out. Go to the website jillonmoney.com, click the contact us button, write us a note, check the box if you want to come on the air and just don't judge it. It's probably going to be okay. We can work our way through many of the situations you guys present to us. You can subscribe to us on the Odyssey app or wherever you find your favorite podcast. Please leave us a rating and review wherever you listen. We also ask that you put your hands, metaphorically or maybe physically, on someone's back. As long as you have permission, give someone a hug. Hugging is good. Change your work, Change your wealth, Change your life. Thanks for listening. We'll talk to you tomorrow. Hey, gang. I just made a first time ever purchase on behalf of the pod. I was so psyched because Mark and I don't do a lot of promotional materials, but I was able to create a branded sweatshirt. Yep, a Jill on Money branded sweatshirt with vistaprint. Now, I'm not usually good at these things, but Vistaprint made it simple to bring this idea like, oh, wouldn't it be cool if Mark and I could create some sweatshirts that we'll try out and maybe the listeners would want to get them as well. They've got these great design tools, they have fast shipping, human support if you need a little guidance along the way. Because the sweatshirts were so easy to execute. Now I'm thinking about doing some other stuff. Maybe there's some baseball caps or, I don't know, other fun stuff that you guys would want. You'll let us know. There's a reason that over a million people trust Vistaprint for their small business print needs. Vistaprint print your possible right now, new customers get 20% off with code [e-mail].

[Emma Greed]

I'm Emma Greed, host of Aspire with Emma Greed, a podcast where I sit down with people who don't just dream big, they build big. From culture shaping voices like Mel Robbins, to leaders redefining success like Tracy Ellis Ross, to game changing entrepreneurs like Mark Cuban, Aspire is about mindset, ambition and doing the work that actually moves the needle. If you're ready to raise your standards and take charge about the life and career you're building, Aspire is where you start, follow and listen to Aspire with me, Emma Greed, an audacy podcast available wherever you get your podcasts.