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Jill Schlesinger
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Jill Schlesinger
Welcome to the Jill on Money show. It's Tuesday, May 26th, I hope you had a good Memorial Day weekend. The unofficial start to the summertime. Also the unofficial start time to you shutting down about anything financial. I know it happens. It's summer. You're still on an academic calendar even though it's 40 years ago. It doesn't matter. If you would like to squeeze in a financial question before your jesco off for the summer, just say, I just need to relax. I understand that, but before that actually occurs, why don't you get in touch with us? Go to our website jillonmoney.com click the contact us button, which is in the upper right hand corner. Wherever you are navigating on the site, write us a note. And if you would like to join us on the program live, then just check the box. By the way, we are seeking folks who will come on video with us for our other program, which is called Money Moves, which is starting up just next month. It's in the old Money Watch feed. We're just turning that feed into a different show. And that show is going to be really geared towards people who are younger. So let's say south of 45. If you're younger than 45, you'll be on the Money Move show and we'd love to get you on camera or, or here's another opportunity for you. You can just shoot a video of yourself and send it to us. Just easy peasy. Say, I have a question about blank, especially if it's sort of a single issue question. We'd love to hear from you again. Jillonmoney.com, click the contact Us button. If you are listening and you have somebody in your life who is under the age of 45, tell them all about Money Moves. All you have to do is subscribe to the Money Watch channel. It'll just happen. Hey, while you're on the website, don't forget, besides subscribing to our podcasts, you can subscribe to the free weekly newsletter which comes out on Fridays. And we'll have all the information about the new show in that newsletter and you'll check it out. So please do that. And what else can I tell you? Oh, next month, don't forget, we've got our next webinar. It's all about Social Security. Mark, have we started to get some Social Security questions for the expert who will be joining us at that live webinar? Heather Schreiber? Yeah, you know, you must have just mentioned it recently because a few rolled in over the weekend. Great. If you've got Social Security questions and you want Heather Schreiber, who is an incredible expert who will be joining us for the Jill on Money live webinar on June 17th. Definitely send us that ahead of time because we always get slammed and we do get a little bogged down answering questions live. Don't forget to join us live. You must be a member of Jill on Money Live. That'll cost you 45 bucks for the next 12 months. It will entail this webinar. Three more after this. Bonus audio, video content, the fabulous Ed slot, the beautiful graphics. Mark, did we get those behind the paywall? Also all the Ed Slott charts and fun things that are there. Right? That's there. And we just recently did a couple of chats with Michael Clinton and Beth Kobleiner. Those are both up there now as well. So much stuff. Mark is just a one man content machine. I'm just the mouthpiece for that machine. Anyway, join us for Jill on Money Live. If you don't want to spring for the 45 bucks for the next 12 months, it's okay. You can just purchase a single webinar. It'll cost you 15 bucks. Can't join us live, but you will get that webinar once it airs. But join us because it's more fun anyway. Okay. Today we are joined by Susan from Pennsylvania. Hello, Susan, how are you?
Susan
I am great. How are you?
Jill Schlesinger
Fantastic. What's going on? How can we help you out?
Susan
In two letters, AI is what's going on.
Jill Schlesinger
Oh, gosh. I was just on an editorial call where somebody was raising this issue about AI I said, I don't think we can do enough stories about how freaked out everybody is about AI and you count yourself among one of those freaked out people, right? Yes.
Susan
Starting to freak out. So I've had my own one woman content business for over 20 years now. It's been very lucrative and I've been aware of AI for several years. But I'm really starting to see signals that it is going to encroach on at least the historic way that I've done business. Normally when a client moves from organization A to organization B, I hear from them within a couple of months and start working with them again. I had two instances where clients made those kind of moves and I didn't hear from them and well, actually I did. And then I didn't and come to find out they are very much using AI and they are kind enough to say completely changing. And so, you know, I turned 50 last year and I'm not ready to stop working. But I'M not sure that I'm going to be able to do business as usual for 10 or 15 more years. And just kind of wanted you to sort of weigh in on where we are, how things look like if it were to decline a bit or if I get to a point where I need to completely pivot to something else, how that could look financially.
Jill Schlesinger
And yet you are asking Jill and not asking Claude.
Susan
Yes, I've decided Claude is extremely promiscuous because I'm. Claude is just spreading his wealth everywhere. When I read LinkedIn, I just roll my eyes continuously.
Jill Schlesinger
So, okay, first of all, I, I am in your situation as well. I am like a one woman content machine as well. And I wonder, you know, the stuff that I put out, at least written stuff, anybody can get it. Like anybody can say, you know, give me 500 words on, you know, the best advice for college graduates. Right. So I feel what you're feeling. And I think any of us in the content creation world, we're using AI ourselves, but also trying to figure out how do we differentiate ourselves in this world where there is AI and how
Susan
do you, how do you price?
Jill Schlesinger
Yes, that's the quandary. So let's start with how freaked out you have to be because I think that you will make the transition. The question is how fast do you have to transition or can you kind of take your time because you've done such a good job of saving and investing. So you said you are 50, are you single? Are you partnered? Are you married?
Susan
I am married and my husband has been retired for nine years last month.
Jill Schlesinger
Oh, wow. Okay. How old is he?
Susan
He is 69.
Jill Schlesinger
Okay. Did he claim Social Security?
Susan
He has. So he claimed at full retirement age and net of his IRMAA and all that good stuff. It's about 39,000 a year.
Jill Schlesinger
Okay. Does he have a pension?
Susan
A small one. About 18,000 a year.
Jill Schlesinger
So 39 and 18 is coming in no matter what, right?
Susan
Right, yes.
Jill Schlesinger
Okay, great. Do you guys have kids?
Susan
We do. One that is fully, fully grown and one who just graduated and is going to launch later this month, has a phenomenal job and our bills will be coming down very shortly, I think.
Jill Schlesinger
Oh, that's what good timing for you. Wow, that's amazing. So you mentioned irmaa, which is the fact that your husband, who is on Medicare now has an adjustment because you guys make enough money together that the government kind of whacks you for that. So in addition to his Social Security and his pension, what other income do we have? Is it just Your self employment income.
Susan
That's right. He has not started taking anything from his retirement assets, and he probably. He doesn't plan to until he has to.
Jill Schlesinger
Okay, and how much do you earn right now, Susan?
Susan
I went back and looked at the last 16 years. I've averaged about $250,000 a year. I'm still on that track so far this year, but I can see a bit of a cliff. Okay, so.
Jill Schlesinger
All right.
Susan
That's the historic path.
Jill Schlesinger
Okay, let's talk about the money you guys have saved. So you said he has not yet tapped his retirement plan. So let's talk about his retirement assets first.
Susan
Okay.
Jill Schlesinger
How much has he squirreled away and is it mostly traditional?
Susan
It is all traditional. He really. There wasn't a Roth 401K when he. So he has got 1,535,000 across his traditional.
Jill Schlesinger
Great. That's awesome. Fantastic. And he doesn't want to tap that until he turns. Until he has to at age 75, is that right?
Susan
Yes. And in his ideal world, he would tap that and then turn around and put it in the brokerage account.
Jill Schlesinger
Okay. Okay, let's see if we might need some of that. How have you saved for retirement, traditional assets?
Susan
I have 1 million 313. And Roth, I have 342,000. I actually started doing all Roth in my solo 401k a few years ago.
Jill Schlesinger
Great, that's amazing. So you got a bunch of money in retirement. Do you also have brokerage accounts between the two of you or each of you individually?
Susan
We have a joint. It's about 1.6.
Jill Schlesinger
My God, you guys got a lot of moolah. Okay. Mark's laughing. Okay, and in that joint account, does that include just some safe money, meaning cash savings, high yield Savings, Money Market CDs, or do you have other money that's set aside for that?
Susan
We have about 60 ish thousand just sitting in bank accounts. But then across all of the retirement and brokerage, we have about 450,000 in cash. But most of that brokerage is in stock index funds. Index 500 in total stock at Vanguard.
Jill Schlesinger
Okay, and are you guys managing your own money?
Susan
We are, yes.
Jill Schlesinger
Okay. Susan, do you guys own your home?
Susan
We do. It's paid off. We could sell it pretty quickly, I think for probably right, about a million.
Jill Schlesinger
Okay, but you want to stay?
Susan
Yes.
Jill Schlesinger
Okay. Any other real estate, rental, real estate, second home, shares of anything? Okay. And besides the fact that you think that your income is going to drop significantly, is there anything else financially on the horizon?
Susan
No, we actually have Done a lot of stuff on the house that has gotten it in good shape. So not anything big like that. We each have an HSA that's about 91 combined.
Jill Schlesinger
Oh, very good. How do you get health insurance? You pay for it yourself?
Susan
I pay dearly myself, yes.
Jill Schlesinger
How much is that, just out of Curiosity?
Susan
It's about 1,000amonth.
Jill Schlesinger
Okay, so now that you have got one launched and one about to be launched, what do you figure your expenses look like?
Susan
Well, we actually spent some time on that, and it's a bigger number than I wish it were. I was listening to.
Jill Schlesinger
Oh, come on now. Wait a second.
Susan
Can I just say hundred a month sounds pretty good. I don't know how you pull that off.
Jill Schlesinger
Okay, listen, this. There's no judgment here, okay? Let's just figure like, the number's the number and maybe it doesn't matter. So what do you figure again? And I hope that this is not. Oh, we are going to cut this and cut that. Like the number you really would like.
Susan
Let's call it 15,000amonth.
Jill Schlesinger
You will not have any old pension money, Right. There's not going to be anything coming through in your. For you down the line, right?
Susan
No, but my husband's does continue at that same level. There's no cola, but I will get that for my lifetime as well.
Jill Schlesinger
Oh, no cola. That's interesting. Okay, all right, that's good. How about your health? His health? Everything okay?
Susan
Yeah.
Jill Schlesinger
All right. So what we now know is that between his Social Security and pension, just in today's dollar dollars rather, he got about a third of the money you need. Right. Social Security and pension, 4750amonth. So we need 10 or we need like 12 grand a month. Ish. Like when I think about paying taxes. But let's just, you know, we need about, you know, $12,000 a month so you can live your life. Okay.
Susan
And that is after tax money. Like I didn't, you know, the taxes obviously change depending on what I make.
Jill Schlesinger
Yeah, that's what I'm just. I'm going to say because your husband had and because of your husband's income of that 4750amonth. I'm just assuming that we need another. Say, 12,000 less taxes nets you 10,000. That gives you your 15,000amonth with your husband's stuff. I would think that's a safe way to approach it. A gross amount of all of your assets. Now let's go through the assets again for a second. Your husband's going to be so mad at me, because I want to tap that traditional money sooner rather than later. I don't love the idea that he's going to have to take the money out. So it may be that as your income goes down, that is when we start taking his money out, he's going to have to take it out one way or the other. But if your income is going down dramatically, you would tap his accounts first. Right? Because we need to get that money
Susan
out anyway, even if we don't spend it. Like, even if you're going to spend
Jill Schlesinger
it come out, it has to come out no matter what. So you're going to pay tax on it. But who says you're not going to spend it? In other words, let's say this year everything is status quo. And I don't think that you go from 250 to 0, but let's just say, let's pretend from 50 to 55 instead of 250 a year, your income's going to drop. Let's give me a number that you feel like, eh, I'll figure out how to make blank amount of money a year.
Susan
Oh, gosh. I mean, that's the big question. I mean, I, I would not want to go much below 200, to be honest.
Jill Schlesinger
All right, I'm going to say, let's say you're making 120 grand a year, right? Oh my God. You got, don't freak out. Let's just, let's play with that as a possibility. Okay.
Susan
All right.
Jill Schlesinger
So at 120 grand a year, you stop putting any money away for retirement. You're just done. You're living on that money, right? Plus you've got, so that's, you know, your, that'll be 10,000amonth. Plus your husband's Social Security and pension kind of gets you, that saves you. So if you had a situation where you went from 250 to halved. Right. 125. Right. If you had half as much income, the first thing you would do is you would say, I'm not putting any money into retirement. You guys have plenty of retirement money. It's great. So I wouldn't worry about that. But if you made half as much money between your income and his Social Security and pension, you'd live, you'd be okay. You'd live your life. You wouldn't save anymore. Shouldn't we just plan it as if that were to happen? And anything extra is gravy, right?
Susan
Yeah.
Jill Schlesinger
Oh my God. I've depressed this woman. Oh my God. This is not a Claude Wouldn't have done this. Claude would have been like, you've done a great job, Susan. Fantastic. Clearly not a financial problem. This is all between the ears.
Susan
Okay. You haven't even talked to him.
Jill Schlesinger
Oh, good old him.
Susan
Hypothetically, say I was able to kind of sustain more of the 200 to 250. Yeah, you were me. Would you stop doing the Roth contributions anyway and start just saving that 30 or so grand in the brokerage so that I have more flexibility since it's so many years till I'm half?
Jill Schlesinger
Yeah, sure. I mean, I don't think you're going to have to do that, but, I mean, you would. You might. Maybe you would. Instead of put. If you had 30 grand extra a year, maybe I put 10 in the Roth and 20 into the brokerage because I still. As you're young and that Roth money having that tax paid is going to be lovely. Splitting it two thirds, one third seems good, but I don't think this is like. So let's just say. Let's go back to my scenario.
Susan
Okay?
Jill Schlesinger
You make 125 grand a year. From 50 to 55, you live okay. You have absolutely no problem. You've supported yourself. You don't save any more money, though. Okay. You're living on your salary or whatever. You use your income, his Social Security, his pension. Now you're 55 years old. Okay. And let's say from 55 to 59, do you want to just keep working, doing something?
Susan
Oh, yeah. I mean, I really. I'm not looking to stop working. I just.
Jill Schlesinger
Well, what would happen if we then said, okay, in those five years? I give you five years to figure out, like, how to manage the transition of whatever happens next. Right. So that's five years where, you know, hopefully you make more. But if you made 120 would be okay. Did you ever. Have you always worked for yourself? I mean, would you ever work for another company?
Susan
And that's one of the scenarios that I'm kind of.
Jill Schlesinger
I have.
Susan
I spent about a decade working for other, you know, for companies. And given the cost of health insurance, especially as I get older. And one of my hypotheses is that with AI, the freelance model is going to get harder to justify. Whereas if I were inside, I could use their own.
Jill Schlesinger
Yeah.
Susan
Private language models. And yes, that I do. So I'm not opposed to going in house either now.
Jill Schlesinger
So maybe there's like this idea that even, like if the next couple of years. You see how it goes, maybe we're overstating the fear factor. Maybe we're not. But at the same time you're looking for jobs, you're sort of seeing how this goes. And maybe you would go in house. Going in house wouldn't mean they had to pay you 250 a year, by the way. Honestly, they paid you like 180 or 150 a year. You could make a good go of it, 150 a year. The insurance cost will come down. The actual cost of health insurance would come down. There'd be some retirement account with some match. You know, all these things add up, right?
Susan
Yes.
Jill Schlesinger
And so that wouldn't either also be a bad outcome. But it's also possible that from 50 to 55, if you've taken a haircut, maybe from 55 to 59, you take another haircut. Mostly because you say, well, you know what? My husband now has to pull money out of his retirement account. I don't have to make so much money. We can live on the withdrawals from his account. And instead of him putting into the brokerage account, you're actually using it to live on. But then the pressure's off you in terms of what you earn. So let's just pretend that for you, the two phases of 50 to 55, where you're doing something, making 125 grand either for yourself or working somewhere else, the next phase of 55 to 59, the pressure comes down even more. I mean, honestly, if you made 80 grand at that time from 55 to 59, and your husband's pulling money out of his retirement account, which he has to do anyway, and you have to live on it. And at the end of the day, I hope that he, that you guys pull all the money out of this traditional account of his before you ever have to think about touching your money. And your money just grows. What's wrong with that? And I haven't even Talked about the $1.6 million in the joint account. The weird thing is, for him, he won't want to hear this. It's better for you, for you, the 50 year old, to have him pull money out of the traditional account again. If your tax bracket especially is going lower, pull that money out now and get the money out and live on it, because the money has to come out no matter what. If he were turning 75 right this second, he has to take about 4% of the money out. That is 61 grand. Now you're going to pay tax on it and you can live on it, or you can pay tax on it and put it in your brokerage account. It does not matter. You're going to have, you have enough money. You guys, Mark made the best analysis, which is this is not a. It's not a. This is not an asset and liability and cash flow problem. This is a problem that is somewhat emotional because it's scary. And to have your income drop dramatically is scary. This is not unlike my friend who was a doctor and one year Medicare changed the coding on her reimbursement and her income was down by 4 0%, 40% in one year. And it was a massive adjustment. She was young and she had kids in college, so it was a big deal, right? However, the most amazing thing happened in the subsequent years she has figured out how to bring that income back into her world. Maybe it was working few extra hours, maybe it's working one weekend day to be able to justify it, but she figured it out. And I'm not saying that AI is going to take you out, you know, lock, stock and barrel, but I think it is fair to say that you can give yourself some time to adjust. You are willing to work, you want to work.
Susan
Part of it that's freaking me out is the loss of identity. It's sort of like when being a great writer has been core to who you are since you were like 8 years old, to have the writing kind of be democratized and essentially free. A little jarring.
Jill Schlesinger
I am so with you. I am talking to you on a day where I don't want to make this about me, but we all go through this. I am talking to you on a day when it is my last day of doing radio for the CBS network and my identity started with the radio division. I mean, television notwithstanding, I'd always felt like, hey, you know, I have my voice. I can get too old and too wrinkled and too ugly for TV and they won't put me on the air. Someone younger and more vibrant will come on the air. I will lose that job. But I can always do radio is what I always thought. And thankfully, although the demise of radio came sooner than I thought. But I have this podcast, right? This podcast was not my money making. I mean, I always made more money with through the network than I did on this podcast. But now as I make the transition, it is hard for me to think of this, you know, that I'm doing just the podcasting when I love talking to people. But there was something that I really missed about radio because it's live and it's fun and I love working with all these super duper pros who made Me so much better at my job and that world's going away and it is now gone for me. But, you know, as I speak to you, and we air this on the 26th of May, the radio division at CBS is done. It's gone. So, so much change. And I understand that there's an emotional aspect to it. Of course there is. We're emotional. You know, we aren't clawed, we aren't AI models. We actually have emotions. So what I think is smart is that you are basically ahead of the curve. You really are. And you're thinking this through and you're saying to yourself, hey, what are the things that I need to consider if my income is going to go down? What are the ways that. Where is your expertise needed? Maybe it is in house. Maybe it is like you said, using their large language models, using their. I mean, you do need a human being to prompt the model and then to check it and then to listen. I've done this, I've said just for fun. Hey, let me see if this, Let me see if Claude can write an article for me. I mean, it's not very good, but there's enough stuff that I have written that I can get a sense of like how I can make it and put it in my voice. And I think that every organization is going to need someone who gets that. And you may be that person who's like the really on the front line of seeing it. Thank God you have money. Well, that's it. I mean, like you said, Jill, she's not going from 250 to zero. And let's just say she went to $100,000 continuing to work for herself financially, even if it was $100,000 for the next 10 years. You guys are so fine. It's not even. There's no question, there is no question financially. And if your husband needs a little prompt about the idea of accessing those retirement funds, we're happy to talk to him as well. But for. The question that you're posing is one that every single, per. Every single knowledge worker is asking him and herself. I do, yeah, they should be exactly right. And so someone just said, well, you know, this is, was a great case for the, you know, this is why young people should just go into trades. I'm like, this is as stupid as saying, like you're going to say, oh, everyone should be a bricklayer. Okay, well, what if I don't? What if I can't do that? What if I'm not good at that? It's like saying Everybody should be a coder. Which, by the way, wasn't the greatest advice, was it?
Susan
No, not in hindsight.
Jill Schlesinger
Not in hindsight. And you never know. I think you're in really good shape. I am going to be interested to hear how you move forward. Just, you know, I always ask these questions. So do you have your estate documents done?
Susan
We do. They're very outdated because now our younger child is well past the age of adulthood, so we probably need to update them.
Jill Schlesinger
But, yeah, get a little update. Get that going. I mean, that's another thing, like people say to me, oh, well, now I definitely don't need to go to a lawyer to do my estate planning.
Susan
Oh, please. No.
Jill Schlesinger
Yeah. I mean, it is your whole life and your death. But, okay, if you just want to let Claude do it, fine. Good luck. I still like the human touch on that. So you get that done, Susan, and you keep us posted. We're here. We're not going away.
Susan
Awesome. And I know that that's true eight years after my first appearance, so thank you.
Jill Schlesinger
I mean, you were an early caller, so thank you so much for coming on. And hey, gang, if you're worried about whatever's going on in your industry, but specifically, if you really are freaking out about AI, I hear you. It's scary. Get in touch with us. Go to jillonmoney.com, click the contact us button. Write us a note. We will walk you through it. We will commiserate with you. We will understand whether or not you have the ability to keep doing what you're doing, maybe at a reduced rate, who knows? But it is important that you reach out. You let us know how we can help you. Don't forget, 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 or have Claude do that for you. Of course, we ask that you lift someone up that you don't have Claude to do. You do that yourself. Change your work, change your wealth, change your life. Thank you for listening. We'll talk to you tomorrow. Hey, gang, you know I've changed my tune on Bitcoin. Meaning I know that a lot of you are bitcoin curious, and that's okay. I know you're not putting all of your money into this. If you've been curious about Bitcoin, but haven't made the jump yet, Cash app makes it easy. You can set up automatic purchases with zero fees or buy larger amounts, also with zero fees. Start small or go bigger. It's designed to be simple either way. So whether you're just learning or ready to try it out, it's built to meet you where you are for a limited time. New customers can get $10 added to their balance. Just use code CASHAPP10 when you sign up. And don't forget this part. Send at least $5 to a friend in the first two weeks Terms apply. Cash App is a financial services platform, not a bank. Banking services provided by Cash App's bank partners. Bitcoin services provided by Block Inc. Brand for additional information, see the Bitcoin disclosures at Cash App legalpodcast On my new podcast On Par with Maury Povich, we're getting down to the truth behind the names that you know and love. Unfiltered conversations with legends like Leanne Morgan, Kathy Griffin, Ricki Lake to find out when they feel the most on par. We're breaking it down with Don Lemon, Aaron Parnas, Imani Jones, laughing it up with Josh Johnson, Dan Soder, many more. You know the results are in. Great conversations are always on par. So follow and listen to On Par wherever you get your podcasts.
Podcast: Jill on Money with Jill Schlesinger
Date: May 26, 2026
Host: Jill Schlesinger, CFP®
Guest Caller: Susan from Pennsylvania
This episode tackles the unsettling realities facing small business owners and content creators as AI tools become deeply integrated into professional workflows. Jill Schlesinger takes a call from Susan, a highly successful freelance writer “freaking out” about artificial intelligence threatening her business and sense of identity. Together, they dig into Susan's finances, explore what a business pivot might look like, and share strategies for navigating change in an AI-disrupted world—all while keeping the conversation candid, supportive, and practical.
Susan's Concern:
Quote:
Jill’s Response:
After her husband’s retirement, Susan remains the household’s main earner—averaging $250k annually, but now forecasting a potential drop.
Husband: retired 9 years, 69 years old, collects Social Security ($39k/yr) and a small pension ($18k/yr).
Two children—one launched, one just starting a new job.
Assets:
Expenses:
Jill's Assessment:
Quote:
On AI 'Freakout':
Identity & AI:
Career Transition Wisdom:
On In-House Roles vs. Freelance:
For listeners feeling threatened by AI or rapid workplace change, this episode underscores that financial planning can provide peace of mind, but emotional adaptation is equally essential. You are not alone—and support is available.