PREVIEW: Starting Over at 68 — A Patreon-Exclusive AMA With Donna

Summary

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HerMoney with Jean Chatzky

PREVIEW: Starting Over at 68 — A Patreon-Exclusive AMA With Donna

Release Date: December 4, 2025
Host: Jean Chatzky
Guest: Donna

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Episode Overview

In this special preview episode of HerMoney, host Jean Chatzky launches a new, Patreon-exclusive AMA (Ask Me Anything) format, featuring candid, one-on-one conversations with listeners facing real-life financial challenges. Today’s guest, Donna, is 68 years old and recently returned to full-time work after years of part-time employment and a long-term disability. Having recently ended a 30-year marriage and now earning a significantly higher salary, Donna is seeking practical advice on how to reinvest, rebuild, and safeguard her financial future as retirement draws nearer. The episode delves into the complexities of “starting over” financially later in life, touching on investing, account selection, dealing with “small” portfolios, and leveraging newfound income.

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Key Discussion Points & Insights

Donna’s Background & Situation ([01:11]–[07:36])

• Life Changes and Career Transition:

  • Donna, 68, lives in Poulsbo, Washington, a small, close-knit tourist town.
  • After a 30-year marriage ended, she moved locally, still works in Poulsbo, and recently shifted to full-time employment at an eco-tourism company where her daughter (her boss) also works.
  • Previously worked part-time for decades due to medical issues and disability.

• Emotional and Financial Impact of Change:

  • “It’s a big paradigm shift for me to have to be, you know, out of the house, like a 9 to 5. But along with that shift is a paycheck, a nice paycheck, which I haven’t gotten one yet… I want to be able to do something with the money that makes sense, that can grow the money, and I’m just at a loss.” — Donna [02:36]

Financial Snapshot ([03:51]–[06:42])

• Assets and Accounts:

  • 401(k): Around $6,700, reflecting years of part-time contributions and a 4% employer match.
  • House: Owned outright, valued at ~$550,000.
  • Merrill Lynch Account: Approximately $80,000, consisting mostly of Roth funds with a small IRA portion.
  • CD (Credit Union): $20,000.
  • Ally Savings: Used as emergency savings.

• Recent Financial Decisions:

  • Cancelled a new home purchase after red flags surfaced in the development, resulting in a $12,000 loss. Donna views it as a necessary, if costly, decision: “Sometimes it’s better safe than sorry.” — Donna [06:04]

Income and Goals ([06:20]–[07:36])

• New Earning Power:

  • Donna’s new salary is about $90,000 per year (“double basically what you were earning” — Jean [06:29]), providing significant new saving opportunity.

• Priorities:

  • Main objective is to build toward retirement, utilizing increased income for strategic saving and investing.
  • Expresses frustration at difficulty finding financial advisors willing to work with a “smaller” portfolio:
    • “I’ve talked to four different people and they, because my portfolio is low for them, it’s like, well, it’s not worth it for us to have you and it’s not worth it for you to pay a fee. And so I’ve just been… dog paddling… three years… on this route to get some direction and help.” — Donna [06:52]

• Jean’s Advice (Initial Overview):

  • Emphasizes maximizing use of tax-advantaged investing (401(k), Roth IRA).
  • Points out the value of Donna’s new monthly savings power and the need for a portfolio that will last “to and through retirement.”
  • “You want to put as much of it into tax-advantaged investing as possible.” — Jean [07:36]

Retirement & Living Expenses ([08:07]–[09:11])

• Social Security:

  • Donna is already receiving payments (converted from disability to Social Security at full retirement age).

• Expenses:

  • Living costs are low: house is paid off, daughter shares living expenses and covers utilities and taxes.
  • Donna mainly pays for food, gas, and home maintenance.

• Retirement Outlook:

  • Donna aims to work for five more years (maybe up to ten), but wants clarity on how to optimize savings during this period.

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Notable Quotes & Memorable Moments

• On Exercising Caution Despite Financial Loss:
  “Sometimes it’s better safe than sorry.” — Donna [06:04]

• On Advisor Accessibility:
  “Because my portfolio is low for them, it’s like, well, it’s not worth it for us to have you and it’s not worth it for you to pay a fee… three years… on this route to get some direction and help.” — Donna [06:52]

• On the Opportunity of a New Start:
  “You’ve got a great opportunity here because… you’re going to be spilling off a couple thousand dollars a month that you’ll be able to invest.” — Jean [07:36]

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Timestamps for Important Segments

• [01:11] Donna introduces herself; life in Poulsbo, Washington.
• [02:36] Donna describes her career break, return to full-time, and financial disorientation.
• [03:51] Breakdown of assets: 401(k), house, Roth IRA, CD, and savings.
• [06:04] The decision to cancel a home purchase and absorb the loss.
• [06:29] Earning $90,000/year and impact on savings potential.
• [06:52] Challenges with financial advisor access and “small” portfolios.
• [07:36] Jean’s foundational advice—tax-advantaged savings, goal to build a retirement portfolio.
• [08:23] Donna’s Social Security situation.
• [08:50] Current low living expenses; daughter shares household costs.
• [09:11] Preview ends; Patreon invitation.

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Summary

This preview episode candidly showcases the financial complexities of “starting over” in one’s late 60s—navigating newfound income after life upheaval, seeking help when traditional advisory models fall short, and the pursuit of security amid uncertainty. Jean Chatzky and Donna touch on deeply human challenges—decision fatigue, the sting of financial missteps, and the dignity in taking another shot at financial independence. The conversation sets up a practical, hopeful roadmap for women in similar shoes, emphasizing actionable steps and the value of community support.

To hear the full conversation—including tailored advice on retirement planning, RMDs, Social Security, and creating a sustainable financial plan—subscribers can access the full episode on Patreon.

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Transcript

[A]

Hey everyone. Jean Chatsky here. Today we're doing something a little different on the Hermoney podcast. We're giving you an exclusive preview of one of our brand new Patreon only AMA episodes. Conversations where I sit down one on one with listeners to talk about their real financial conversations in real time. You're about to meet Donna. She just turned 68. She's stepping back into the workforce full time after years out due to disability and the end of a 30 year marriage. She is making more money decisions than ever before, almost double her previous salary. We talk about how to invest when you're starting over later in life, how to choose between Roth and traditional accounts, and what to do when every advisor says your portfolio is too small. So here's the first half of our conversation with Donna. If you want to hear the rest and all of our new bonus content, join us by heading over to patreon.com and searching hermoney podcast.

Hi Donna, welcome to the show. Thank you so much for being with us.

[B]

Thank you very much. I really appreciate it.

[A]

Of course. So tell me a little bit about you. Where do you live? What do you do? What made you write?

[B]

What made me write was I was just reading one of the weekly emails and I just started having all these questions and you're the first time I've ever written to anybody, so.

[A]

Oh, well, I'm honored.

[B]

Yeah. And I. I've been reading your newsletters and seeing you around for many years. So I work in a small town called Poulsbo. It's in the Cat Peninsula in Washington, a ferry ride from Seattle. And I lived in Poulsbo for 30 years and I split up from my husband of 30 years and I moved up the street. So I still work in Poulsbo. It's a tourist town. It's about initially 12,000 people, but that doesn't include the unincorporated area. So it's just a really charming city. I love it. It's fun to just walk down on the waterfront and you know, see tourists and answer people's questions. And I work for a small eco tourism company. We do two boats in Alaska. Environmental education. One boat's 20 people, one boat's 24 people. So very small, intimate. And I've been with them since 2011, but I had a few year break in between. I had some surgeries and some medical issues. So I've been back for about three years and as I wrote in my email to you, I've been working half time basically part time for the last 30 years and I started Full time last week. So it's a big paradigm shift for me to have to be, you know, out of the house, like a 9 to 5. But along with that shift is a paycheck, a nice paycheck, which I haven't gotten one yet. It's not until next week, so I can go. Yay. So I want to be able to do something with the money that makes sense, that can grow the money, and I'm just at a loss.

[A]

I mean, we can figure that out. How old are you?

[B]

I just turned 68 the other day.

[A]

A happy birthday.

[B]

Thank you.

[A]

How long do you think you'll continue to work?

[B]

Probably for, I don't know, five years.

[A]

Great.

[B]

Maybe ten. I don't know. It depends. But it's a small. It's a family foundation. So there's only 14 people in the company. And my daughter, I work with my daughter, actually. She's. She's my boss and I love it. Yeah. And the rest of the company is based in other parts of the country.

[A]

And tell me a little bit about how you're situated for retirement. How much do you have saved? Where is it? Does this business come with a retirement plan?

[B]

I do have a 401k that I've been with them since they started. They started it after I had started a couple years later. So when I had left for a few years and came back, I was already vested in, so I was able to jump right back onto it. And I think, think because I was only working part time, I believe I had like 25% of my income going into the 401k. They match four. So I have that right now. It's still low because I've only been part time. I think I'm at about 6,7000 in that. I have pretty much most of my retirement's in my house. I own my house outright, and it's worth like.

550 ish. I do have a Merrill Lynch, Roth, mostly Roth, and a small IRA. And I have a CD at a credit union. That's like $20,000. I have Ally savings I had opened up just to throw my savings from the bank into something that makes more than 0.01% interest.

[A]

Yep.

[B]

Yeah. So I kind of have money, you know, here and there in total. Mostly right now, it's like my house is my.

[A]

Okay. And what is in. How much is in the Merrill lynch account altogether?

[B]

It's in Merrill lynch altogether is about 80.

[A]

Okay. All right. And then the Ally account. Is that your emergency money?

[B]

It is it right now. It's pretty low. I'm getting ready to transfer some money. I had bought a house in a new development back in Poulsbo where I work and love and canceled it in July and I lost my. And I knew I would if I canceled it, but there were too many unknowns. Things were starting to get really shaky in the development. They were dropping the prices and like 20, $30,000. So I lost like $12,000.

[A]

But sometimes it's better safe than sorry.

[B]

Exactly. It just. Things weren't looking good. So. So I'm. My paychecks are going to be huge. Huge for me because. And I don't know. Do you want numbers?

[A]

Sure. I mean, I'd like to know. I'd like to know. You wrote in your email that you're going to be earning about $90,000 a year, which is double basically what you were earning. So that's amazing. And it, it means that if you were living on half, it means that there's a lot of additional money to save. Am I reading that right?

[B]

Exactly. Yes, exactly. Okay.

[A]

And the goal of saving this money is it, Are we aiming for retirement? Is that sort of where we're trying to go here?

[B]

Yeah, yeah, basically. And I'm, I think I had written that I've just been having a hard time finding like a financial, even a fiduciary here. I've talked to four different people and they, because my portfolio is low for them, it's like, well, it's not worth it for us to have you and it's not worth it for you to pay a fee. And so I've just been sort of swimming, dog paddling and, and each year goes by. It's been like three years that I've been on this route to get some direction and help because you know, I could put it in the Merrell, but then I have to go in and invest it and I need to join your investment club. That's what I'm going to do. But.

[A]

Well, you can absolutely join our investment club, but it's not going to necessarily answer this particular question. Right. You need a portfolio that's going to get you to and through retirement. And you've got a great opportunity here because if I'm reading it right, you're going to be spilling off a couple thousand dollars a month that you'll be able to invest. You want to put as much of it into tax advantaged investing as possible.

[B]

Right.

[A]

And then you want to continue to invest the rest so that when you get to retirement you are as comfortable as you can possibly be right. I assume you haven't taken Social Security. You won't take Social Security till 70.

[B]

I did take Social Security a number of years ago because I was on disability. When I had left the company, I had like neck fusions, back fusion knee replacements. So I had lots of bone issues. And so that disability has just turned into Social Security because I'm at full retirement age.

[A]

So your Social Security payments are locked. So what do you what does it cost you to live each month?

[B]

Not a whole lot because my daughter pays for she lives with me and the house is paid for. So she pays for all the utilities and the taxes. And so it's basically food and gas and maintenance, which of course can be a pain. And I've had to do a lot of that. So not a whole lot.

[A]

And that's where we're going to pause Donna's story for now. If you want to hear the rest of this conversation, plus everything we talked about around retirement planning, social securities, RMDs, and how she can finally get a plan in place after years of trying, you can listen to the full episode right now on our Patreon. On Patreon, you'll get exclusive bonus episodes including AMA call in mailbags like this one, a lively private chat with other Hermione community members, ad free listening across the entire feed, front of the line, access to have your questions answered and access to a very special event we're hosting in the new year. Details coming soon. If you love having more Hermoney in your week, we'd love to have you join in. Join [e-mail] CW HerMoney podcast. We can't wait to see you there.