Can I Make a Career Change at 57?

Summary

Podcast Summary: “Can I Make a Career Change at 57?”

Podcast: Jill on Money with Jill Schlesinger
Date: June 17, 2026
Host: Jill Schlesinger (CFP®), with producer Mark
Guest/Caller: Lucas from Los Angeles

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Episode Overview

This episode spotlights the financial and emotional considerations in making a major career change later in life. Jill Schlesinger offers expert advice to listener Lucas, who’s considering leaving a long career in the entertainment business to pursue more meaningful, stable work in the nonprofit sector—at age 57. The discussion balances financial security, the impact of family support, and the courage required for personal reinvention.

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Key Discussion Points & Insights

1. Lucas’s Background and Career Transition Motivation

• Career Summary: Lucas has worked 30 years in entertainment production in LA, where the business has become increasingly unpredictable and stressful.
  • Quote: “I work in the entertainment business… as you know, in the entertainment business are just a little up and down at the moment. And it's just been really stressful in terms of work"—Lucas, [04:48].
• Major Shift: Lucas wants to leave the “chaos” for a steadier, more meaningful job for the final decade of his career, likely in the nonprofit world.

2. Personal Situation and Financial Footing

• Family Status: Single, no children.
• Income:
  • Good year: ~$130,000–$140,000
  • Average year: ~$100,000
• Expenses:
  • About $4,500/month (notably low for LA), with rent at $1,700/month.
  • Quote: “My expenses are about, you know, maybe 4,500 a month.” —Lucas, [06:18].
  • Jill notes: “That's kind of low considering where you live.” [06:32]
• No significant debts: No credit card, car, or student loans.

Asset Overview

• Roth IRA: $76,000
• Brokerage Account: $555,000
• Inherited IRA: $16,000
• Traditional IRA: $243,000
• Roth 401K: $10,000
• Cash/Emergency Fund: $24,000 ([08:10])
• Total Investments: ~$900,000+

3. Extraordinary Family Support

• Generous Sibling: Lucas’s sibling (worth ~$60 million) has offered to buy him a condo in LA, covering all property taxes and fees for life.
  • Jill’s reaction: “Oh my God, I love your sibling so much.” [07:02]
  • Condo budget: $1M–$1.2M ([15:03])
  • Sibling plans to leave money for Lucas’s ongoing care; condo will eventually go to the sibling’s kids.
• Impact: This will drop Lucas’s expenses further by removing rent (currently $1,700/month).
  • Mark: “Never do we hear about expenses going down…substantially.” [13:49]

4. Contemplating the Career Switch

• Desired Job: A steady, rewarding nonprofit position in LA, likely paying ~$75,000/year.
  • Quote: “I kind of want to get into the nonprofit world...just something that's a little more rewarding.” —Lucas, [10:52]
  • Jill estimates: “If it were 75 grand, which would be kind of perfect for you...the 75 grand will cover your expenses, and you've got that big fat brokerage account that you can tap if you'd like…” [11:42]

5. Emotional and Practical Barriers

• Hesitation: Lucas is excited but nervous about closing one chapter and opening another after three decades in one field.
  • Quote: “It's really just kind of, you know, pulling the trigger and just like, all right, this is going to happen.” —Lucas, [12:53]
• Jill’s Encouragement: She emphasizes that Lucas is in an enviable financial position, with unique family support and the means to pursue more meaningful work without risking his stability. Jill and Mark both stress the rarity and blessings of this situation.
  • Jill: “I just—I really think it's great for you. Really. I don't see any downside in this at all, except we'll lose a wonderful guy in production.” [14:39]
  • On generosity: “What an amazing thing. So. But if you are the sibling and you're rich and you want to help out, give us a holler.” [16:12]

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Memorable Quotes & Moments

On Family Support:

• “They would like to buy me a place to live…buy the condo and pay the taxes…and basically for the rest of my life.”
  —Lucas, [06:41–08:47]

On Financial Security:

• “Even without the sibling buying of that place, the fact that your rent is so cheap, you probably could do this anyway.” —Jill, [11:42]

On Change and Opportunity:

• “One chapter closes, another chapter opens. I mean, never, never do we hear about expenses going down.” —Mark, [13:39]

On Accepting Generosity:

• “For, like, a few seconds, I was like, oh, wait, I can't do that. Like, I can't let someone find me a place. And then I was like, wait a minute. What am I thinking?”
  —Lucas, [14:39]

Humor and Humanity:

• Jill jokes about matchmaking for Lucas’s sibling if not for them being married ([15:12]), and the trio teases about “Nepo babies” and the rare occurrence of sibling support at this level.

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Notable Timestamps

• [04:48] — Lucas shares career background, income instability, and desire for change
• [06:32] — Financial situation and monthly expenses
• [07:02–09:58] — Details about sibling’s generosity, property plans
• [10:52] — Lucas describes nonprofit aspirations
• [11:42] — Jill reviews financial and practical feasibility of new career
• [12:53] — Lucas discusses emotional hesitancy
• [13:49] — Mark and Jill comment on rare opportunity of lowered expenses
• [15:03] — Sibling’s condo budget: $1M–$1.2M
• [14:39–16:12] — Encouragement and closing thoughts on gratitude and embracing new chapters

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Conclusion

Jill reassures Lucas (and listeners) that major midlife career pivots can be made safely—especially with sound finances and, in this rare case, extraordinary family support. Jill highlights the importance of aligning your work with your values and emphasizes not letting fear or guilt block positive life changes. The episode is both a practical financial counseling session and an encouraging meditation on second acts.

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Final Thought:
“Put your hands, metaphorically, on someone’s back. Change your work, change your wealth, change your life.”
—Jill Schlesinger, [17:12]

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Transcript

[Jill Schlesinger]

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the Jill On Money Show. It's Wednesday, June 17th and we are here trying to help you navigate your financial journey. And it is the most important thing to stress here is that it is your journey. It's nobody else's. It is everything about what is important to you. So if you've got a question, if you're maybe you're weighing two different jobs, maybe you're thinking about should I be thinking about retiring? Maybe I should be getting some something different in terms of housing. Whatever's going on in your life, we would love, love to hear from you. Just go to our website, jillonmoney.com jillonmoney.com and just click the contact us button. Write us a note. And if you'd like to join us on the air live, then all you have to do is check the box. Mark will do everything else because he's so fabulous. Now, Mark, come on. The microphone, please. What is the cutoff to join us for the webinar tonight?

[Mark]

It's usually right around 3:00 clock Eastern.

[Jill Schlesinger]

Okay, so you got it. 3:00 clock Eastern, gang, if you would like to join us live for our webinar tonight, you must, must become a member of Jill on Money Live. By 3 o' clock Eastern Time. This afternoon, you plunked down 45 bucks that'll carry you through the next 12 months and it will allow you to join our webinar this evening live with

the Social Security expert.

She is the queen of everything Social Security, Heather Schreiber. So it's going to be a great, great night. I know it's going to go by Mark, whenever we do these, like Heather, or when we have the questions that are coming fast and furiously to Ed Slut. The hour goes by so quickly. So I really encourage you to join us, especially if you're thinking about Social Security, have questions about claiming strategies, something's going on. Join us, please. It's going to be fantastic. If you cannot make it live tonight, you can always purchase the single webinar after the fact for 15 bucks. You can do that on the website as well. So. Okay, let us go and talk to our listener Lucas, who's joining us from Los Angeles. Hello, Lucas. How are you?

[Caller Lucas]

Hey, Jill. Hey, Mark. I'm good. How are you?

[Jill Schlesinger]

Good. What's going on? What can we do for you?

[Caller Lucas]

All right, so this is my deal. I'm 57 and live in LA and I work in the entertainment business, have done that for the past, I don't know, 30 years or so, work in production and things, you know, as you know, in the entertainment business are just a little up and down at the moment. And it's just been really stressful in terms of work and it's, you know, sort of inconsistent. So I kind of want to change Careers.

[Jill Schlesinger]

Oh, really?

[Caller Lucas]

Yeah, and just get out of the chaos and do something just a little more steady for the next decade, and then maybe, maybe I'll be able to retire. I mean, that's what I just wanted to ask. Talk to you about.

[Jill Schlesinger]

Okay, so are. Are you single, partnered, married? Where are you in. In the life process?

[Caller Lucas]

I am single. No partner and kids. No kids.

[Jill Schlesinger]

Okay, got it. So we're just planning for you, and that's really actually pretty helpful, especially if you're thinking about a big career change. Right. So right now, I know it's mercurial, production is crazy, but, like, what, approximately what are you earning right now?

[Caller Lucas]

I earn probably in and around, like, on a good year, maybe like 130, 140 and an average year, maybe like, you know, a little over 100.

[Jill Schlesinger]

How has your. How has it been to support yourself on, like, the hundred?

[Caller Lucas]

It's been fine. You know, I mean, I have, you know, I. I have, you know, no credit card debt. I have no car loans, I have no student loans. Like, I don't have a huge overhead. My expenses are about, you know, maybe 4,500amonth.

[Jill Schlesinger]

That's kind of low considering. Where you live. Do you own or do you rent?

[Caller Lucas]

Well, I rent right now, my rent. 1700amonth.

[Jill Schlesinger]

So cheap.

[Caller Lucas]

Yeah, well, I've been here since, like, the 1920s, basically. But there is. There's a big asterisk with that is that I have a super generous sibling who is very wealthy and they would like to buy me a place to live.

[Jill Schlesinger]

Oh, my God, I love your sibling so much. Okay, let's. Before we do that, let's talk about what you've saved on your hundred to 140 grand a year. So tell us what. And are you a. Are you a 1099 worker? Are you W2? Like, are you employed or are you an independent contractor?

[Caller Lucas]

It's W2 work when I am employed, yeah.

[Jill Schlesinger]

Okay. And so what have you squirreled away so far?

[Caller Lucas]

All right, so the. These are my numbers. I have, like, various buckets here.

[Jill Schlesinger]

Okay.

[Caller Lucas]

So I have a Roth IRA that has 76,000. I have a brokerage account that has 555,000.

[Jill Schlesinger]

Okay, nice.

[Caller Lucas]

I have an inherited IRA from my mother who passed away in 2012. It's tiny. It's got like 16. 16,000, I think, in there. And then a traditional IRA of 243,000.

[Jill Schlesinger]

Okay.

[Caller Lucas]

And then a tiny Roth 401K at this company that I'm working at now that has about 10,000 in it.

[Jill Schlesinger]

You've got some money in cash maybe. Yeah.

[Caller Lucas]

Not. Not as much as I would like. I had more before all this upheaval in the entertainment business. And I had just, you know, I had periods of unemployment, so I only have, like, an emergency fund about, like, 24 grand.

[Jill Schlesinger]

But, you know, right now, as you said, $4,500 a month, including your rent. You're not spending a ton of money. Okay, so let's talk a tiny bit about how do you. So your sibling wants to take care of you, which is lovely.

[Caller Lucas]

Yes.

[Jill Schlesinger]

So what would that mean? I'm going to buy you a place. Like a house. A condo. Like, what are we thinking?

[Caller Lucas]

Were thinking a condo. They would like to buy the condo. And also. I can't believe I'm saying this. They'd like to buy the condo and pay the taxes and the way. The property taxes and the way. Basically for the rest of my life.

[Mark]

Wow.

[Jill Schlesinger]

How rich is this person? I need to know, like, worth $100 million?

[Caller Lucas]

No, but I would say in the $60 million range.

[Jill Schlesinger]

60. Okay, then no problem. I'm gonna just say thank you very much, then move on. Mark. Thank. Do you see how I made that shift? Right. Okay. So rich Sib wants to buy, and you're like, is there any question about this? Of course. Do this. What happens if their sibling dies? Then what? They're gonna leave some money for you to be able to do that.

[Caller Lucas]

Exactly. Yeah. And then when I pass away, which I'm totally fine with, it would go to.

[Jill Schlesinger]

You're fine with passing away? Not me. I'm not fine with that happening yet.

[Caller Lucas]

Yeah, not yet. Maybe like 30 years or so. But they would. It would go to their kids.

[Jill Schlesinger]

Okay. But this, obviously. So this is like a ridiculous thing. Amazing. Okay, that's great. So let's pretend that happens. Is that. And it's in the works, right?

[Caller Lucas]

It is in the works, yes.

[Jill Schlesinger]

Good. So that's happening. Fantastic. So, in fact, what you're telling me is that your expenses are going to go down when that happens because you have to pay your $1,700 a month of rent.

[Mark]

Is it just the two of you? Are there other siblings in the picture? I'm just curious now.

[Caller Lucas]

Just the two of us.

[Mark]

Okay.

[Jill Schlesinger]

Oh, I love this. And the kids. And a lot of kids this sib has, or not so much a couple kids. Couple kids. Are the kids deadbeats? You know, are these the kind of kids who are like, oh, God, thank God dad and mom are rich? Because these kids are just never gonna. They're gonna be Little Nepo babies?

[Caller Lucas]

No, not. Not at all. They're like the. The hardest working, like, Gen Z you'll ever meet.

[Jill Schlesinger]

Oh, wonderful. That's great. Also, they'll take care of you, which is amazing. Exactly. Okay, so when you say you're gonna chill out a little bit and, you know, try to change careers, what would that mean for you?

[Caller Lucas]

You know, it's. I've been doing a lot of volunteer work over the past few years, and I kind of want to get into the nonprofit world, I think, and do something that, again, is steady, that has, you know, a little more meaning. Not. Not that what I do doesn't have meaning, but, you know, just something that's a little more rewarding. And I know it would probably require a pay cut, which I think I'm fine with, but it would just be something that, you know, that I can spend, like the next decade doing, that I can look back and be like, oh, my God, like, I gave back.

[Jill Schlesinger]

Yes. Okay. That's fantastic. And have you looked into this or is this still in idea mode?

[Caller Lucas]

No, I've been definitely looking into it for sure.

[Jill Schlesinger]

So you feel like you can get a job for like, 70 grand or something?

[Caller Lucas]

Yeah, probably like, you know, 75. 80, something like that.

[Jill Schlesinger]

Let's call it 75. So if it were 75 grand, which would be kind of perfect for you, because what you could do is get a job. Also, if you're in nonprofit land, there's usually decent matches. But, you know, what I would say is this. You're going to move. Your expenses are going to be reduced. The 75 grand will cover your expenses, and you've got that big fat brokerage account that you can tap if you'd like, just to kind of help you if you do something big, if there's a big trip. I don't think that there's any problem with this. And I think that even if I thought that there was a problem, knowing that you have the safety net of a wealthy sibling is kind of nice, but also, like, I think what they're doing is wonderful because there's probably some feeling with this sibling that it would make them feel more comfortable for you in the future to be able to just know you're set, you know? And I think even without the siblings buying of that place, the fact that your rent is so cheap, you probably could do this anyway. It's just a matter of spending down some of your brokerage. So the. What's holding you back emotionally on this?

[Caller Lucas]

You know, that's a good question. I mean, I feel like I'm. I don't know. I just. It's. You know, I've been in this business for, you know, three decades, and it just. It's really just, you know, and I haven't gotten an offer or anything, but it's really just kind of, you know, pulling the trigger and just like, you know, being like, all right, like, this is going to happen. Let's just do it. I mean, the. The condo thing is definitely happening. Like, I'm looking. I have, you know, real estate agents, so that's definitely happening. So it's just, you know, it's just. It's a big change, like, all around, but I'm a little nervous. But I'm also. I'm also kind of excited about it.

[Jill Schlesinger]

Yeah, I'm ready to go. Mark, any update on your end about, like, what you're thinking? I. I think this is. You're ready, Mark? This is. Here's a situation that Mark could absolutely not relate to.

[Mark]

No. Nor could most people. I mean, you know. No, this is great. One chapter closes, another chapter opens. I mean, never, never. Do we hear about expenses going down.

[Jill Schlesinger]

No, no.

[Mark]

Substantially.

[Jill Schlesinger]

Yeah. I really think that this is a. This is a great opportunity, and I think that it's great that you are able to just take advantage of it. And listen, it would be one thing if it were like, oh, you know, my. My sister, my brother, my sib is doing this. They don't really have enough money to do this, but they're worried. Like, this is such a great case of, like, paying it forward for my family and doing good work, and you then being in a situation where you can get more meaning out of your work. I think it's a great all around. I just. I really think it's great for you. Really. I don't see any downside in this at all, except we'll lose a wonderful guy in production.

[Caller Lucas]

That is true. That is true. No, I. It was a very. When I was presented with this offer of my sibling to buy a place, I was just, like, taken back, and for, like, a few seconds, I was like, oh, wait, I can't do that. Like, I can't let someone find me a place. And then I was like, wait a minute. What am I thinking? I'm like, what are you thinking is right?

[Jill Schlesinger]

Exactly right.

[Mark]

What's the budget?

[Jill Schlesinger]

Oh, yeah. What are we spending on the place?

[Caller Lucas]

It's between a million and 1.2.

[Jill Schlesinger]

All right, very nice. And that'll get you in a place. Is it going to be nicer than what you're living in right now.

[Caller Lucas]

Oh, yeah, absolutely.

[Jill Schlesinger]

So I love this so much. This is great. All right. Is your sibling married?

[Caller Lucas]

Yes.

[Jill Schlesinger]

Too bad. I was about to get very, very excited about fixing that person.

[Caller Lucas]

Happily married, so, yeah, as far as we know.

[Jill Schlesinger]

Okay. Anything else on your end that we need to help you noodle around with?

[Caller Lucas]

No, I mean, that's it. I mean, I imagine, you know, since my siblings taking care of everything, like, taxes wise and everything like that, there's really nothing on my end. I mean, I'll have to deal with all, like, plumbers and stuff like that, but everything else is, like, taken care of, so. That's great.

[Jill Schlesinger]

Amazing. It's amazing. It's completely amazing. So I think that. I think you're in great shape, and I would be ready to rock and roll.

[Caller Lucas]

Excellent. Okay, well, thank you so much.

[Jill Schlesinger]

All right. Hey, gang. If you have a rich sibling who wants to buy you at a place, Mark, this might be a first for us.

[Mark]

Yeah, I can't recall a caller like this.

[Jill Schlesinger]

Over the years, we've had parents who want to do this. We've had parents who want to buy stuff for their. But this is. This is kind of like a little bit different because sometimes you guys, when you're the parents and you're getting in touch with us and we're like, are you sure the kid wants it? Or, you know, are you sure you can afford it? Like, this is so obvious. Like, yes, this guy or gal. I don't know if it's a man. The sibling can afford it. So that's number one. And number two, it's like, I bet that this is, like, peace of mind also for the sibling. Like, I. I don't want to worry that my. My brother's gonna be, you know, living in a rental, whatever. Like, what an amazing thing. So. But if you are the sibling and you're rich and you want to help out, give us a holler. Or if you're the one receiving it, give us a Holler. Go to jillonmoney.com, click the contact us button. Write us a note. If you want to come on the air live, check the box. Mark will do everything else. Don't forget that you can subscribe to us on the Odyssey app or wherever you find your favorite podcast. Put your hands, metaphorically, on someone's back.

Change your work, Change your wealth, Change your life.

Thank you for listening, and we'll talk to you tomorrow. Nerds.

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