Encore Career at Age 50?

Summary

Podcast Summary: Jill on Money with Jill Schlesinger
Episode: Encore Career at Age 50?
Date: April 2, 2026

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Episode Overview

In this episode, Jill Schlesinger, CFP®, speaks with “Jay”, a 50-year-old listener from New England who is considering a dramatic career change from corporate work to becoming a police officer. The discussion focuses on the financial, personal, and practical considerations of making such a significant reset in midlife. Jill and her producer/co-host Mark also provide encouragement, professional insights, and actionable advice on making this kind of “encore career” both possible and sustainable.

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Key Discussion Points and Insights

1. Jay’s Motivation for Change (03:58–04:43)

• Jay’s background: 50 years old, nearly 25 years in corporate America, married 24 years, two children (one in college, one about to go).
• Catalyst for change: After years of stability, Jay feels "sick of corporate America" and wants a more meaningful, “passion project” career. No recent event triggered the shift—just a growing desire.
• Quote:
  • Jay: “Just kind of sick of corporate America. It's treated us well, but looking for something more meaningful.” (04:37)
  • Jill: “Oh, you know, I love a reset. It's right up my alley.” (04:08)

2. Family and Financial Readiness (04:46–05:10)

• Family: Wife (47, works part-time) supports the plan; kids’ tuition covered by 529 plans.
• Financial security: Both kids’ college funds are “fully funded.”
• Living Situation: No outstanding mortgage; house is valued at $1.4 million.
• Quote:
  • Jay: "We've got about 1.6 million in retirement." (07:43)

3. Details of the Encore Career (06:01–07:37)

• Career goal: Become a law enforcement officer. Jay has always wanted this but never pursued until now.
• Transition path:
  • Needs to pass physical and background checks, then attend a 4-month academy, followed by 8 months probation.
  • After a year, would be protected by civil service and union.
• Financial impact: Joint household income will likely drop from ~$180K to $100K/year, but their “low overhead” means this is viable.
• Pension Outlook: If he stays 10 years or until 60, eligible for a $20K/year pension, potentially $25–30K/year if he stays till 65.
• Social Security: Police in this state do not pay into Social Security; Jay could lock in current benefits from prior corporate years ($3,200/month at 65).

4. Breaking Down the Finances (07:43–10:15)

• Assets:
  • $1.4M in retirement (⅓ in Roth accounts), $200K in brokerage, $125K emergency fund, $25K in HSA, and some smaller holdings (e.g., Bitcoin ETF).
• Spending: Estimated at $5,000–$6,000/month, which matches their anticipated new income.
• Planning: Jay’s still contributing “age 50 catch up” to his 401(k) and contemplates front-loading retirement contributions before leaving.

5. Practicalities and Process of Becoming a Police Officer at 50 (11:22–14:52)

• Hiring Process: Physical aptitude test (age-scaled), interviews, background check.
• Timing: Jay plans to give notice at work only after passing initial hurdles.
• Contingency: If not accepted into law enforcement, Jay will stay in his current job or “do something else”—not desperate to quit but motivated for change.
• Location specifics: Some police departments have upper age limits, but not in Jay’s New England town, which surprises Jill and Mark.
  • Mark: “If I wanted to go join the NYPD right now, I wouldn't be allowed. There's an age limit.” (12:11)

6. Final Advice and Emotional Support (13:24–15:16)

• On Track: Jill and Mark agree the finances “look great.”
• Insurance/Estate Planning: Jay is “overinsured” with $3M life insurance, robust disability coverage, and a freshly updated estate plan.
• Family buy-in: Everyone’s on board; kids know grad school is on them.
• Concerns and Support:
  • Jill: “I have great respect for how hard that job is and I worry. But… you are golden. You guys have done an incredible job. If I write The Great Money Reset Volume 2, I'm using this story, okay?” (14:04)
  • Mark jokes about second careers: “I'm thinking about looking into doing other things now.” (15:38)
  • Jill praises Jay: “Gang, if you are called to something, you will make the sacrifice. Jay, we're lucky to have people like you.” (14:33)

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Notable Quotes and Memorable Moments

• On finding meaning at 50:
  • “If you are called to something, you will make the sacrifice.” — Jill (14:33)
• The financial litmus test:
  • Jill: “This seems like kind of a no brainer when it comes to the money part.” (10:39)
• Jay’s decisive response on family support:
  • Mark: “Is your wife and kids…they’re all on board?”
  • Jill: “Everyone’s on board. I’m so worried. I have the anxiety building in my chest right now for this matter.” (13:57)
• Jill’s signature reassurance:
  • “You guys have done an incredible job. You have got a reset. If I write the great Money Reset Volume 2, I’m using this story, okay?” (14:25)
• On physical demands:
  • Jill: “Are you in good shape already?”
  • Jay: “Yeah, definitely.” (14:52)
  • Jill, joking: “He’s drinking protein shakes, he’s in shape, he’s climbing walls, he’s doing all sorts of things...” (14:54)

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Important Timestamps

• Listener call introduction: 03:58
• Jay’s motivation and family situation: 04:13–05:18
• How finances are structured (retirement, brokerage, house, emergency funds): 07:43–08:36
• Encore career details, pensions, and future planning: 09:00–10:15
• Hiring process for police at 50: 11:22–12:21
• Insurance, estate planning, and family support: 13:24–14:04
• Jill’s final words of encouragement: 14:33–15:16

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Episode Tone

Friendly, supportive, pragmatic, and often humorous. Jill and Mark strike a balance between sound financial advice and empathy for the emotional side of a midlife reset. The discussion is frank and respectful—free of jargon and deeply focused on what really matters to the listener and their family.

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Conclusion

This episode highlights not only the financial but also the psychological and practical challenges of embarking on an “encore career” at age 50. Thanks to thorough preparation, strong family backup, and financial prudence, Jay’s journey is both realistic and inspiring—a perfect case study in how to pursue late-stage meaning while keeping your financial house in order.

Transcript

[A]

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[B]

Oh, my God. Don't. Don't tease me.

[A]

Wait a minute. Maybe we're going to have to talk to the CFP board and see if that would be possible. I doubt it. But anyway, it would be really fun. And wouldn't it be fun if we could have all CFPs get do their continuing ed by listening to our show or participating? Maybe this is something we ought to do. Like more, more fun continuing it. Honestly, the continuing ed is so boring, isn't it? It's horrible. Ugh. And so it's good if there's a live person. But anyway, consider this your education for your financial life. So if you all would like to get in touch with us, just go to our website, jillonmoney.com, click the contact us button, write us a note. And if you'd like to join us on the air live, just check the box. Mark will do everything else. Hey, while you're on the website, don't forget subscribe to our weekly newsletter. Comes out on Friday, so that's tomorrow. And also it entitle you to our blog. So you get both. Two for the price of zero, which is great. If you do want to spend some money, check out our subscription service. It's called Jill on Money Live. That's where you have access to quarterly live webinars, the back catalog of those webinars, bonus audio and video content. It's all for 45 bucks for the next 12 months. Okay, so enough about us. Let's move on to you. Jay from New England joins us. Hello, Jay. What is going on?

[C]

I'm a 50 year old corporate worker for nearly 25 years and just looking to make a pretty sizable career change. Step down.

[A]

Oh, you know, I love a, you know, I love a reset. It's right up my alley.

[C]

Well, this is. Yeah, this is a big one, hopefully.

[A]

Okay. All right, I'm ready to help. Wait, before you start. So you're 50 years old. You've been working in corporate America for a long time. Decades now. Like when did this shift occur? Like when did you start thinking about this?

[C]

About six months ago.

[A]

Okay, and did something happen? Was there something that happened at work? Did you get a new boss or were you just ground down?

[C]

The latter. Just kind of sick of corporate America. It's treated us well, but looking for something more meaningful.

[A]

Okay, and you have an us. Is there a partner, a spouse?

[C]

I do have an us. My wife, we've been married for 24 years and we've got two children. One nearly 20, she's in college and a son. It's going to be 18. He'll be going off to college in about a year.

[A]

Okay, the one who's in college. How are you paying for that?

[C]

529. It's covered.

[A]

Okay, so that's covered. And same for the 18 year old will be covered through 529.

[C]

Fully funded. Yep.

[A]

Your wife, how old is she?

[C]

She's 47.

[A]

Does she work full time also?

[C]

She works part time.

[A]

So when do you want this to occur? Like asap, or is there a. Do we have a glide path to get where you want to go?

[C]

I'd say like in the next three to six months.

[A]

When you say, you know, you're just sick of it and you want to reset, what do you want to do? Do you want to keep working in some capacity, just not earning as much as you're earning now?

[C]

Yeah, I want to work full time in the public sector in law enforcement, and it's just a passion project of mine that I've wanted to do off and on for my entire adult life, and it just never really came to fruition.

[A]

You're gonna have to be like, are you talking to me and saying, like, at 50 years old, you're gonna have to become a cop then?

[C]

Well, not have to choose to, but yes.

[A]

I mean, this is what you're choosing to do, Mark. Can you imagine this? I mean, already it's like I'm exhausted from the idea of it. That's wild. Okay, so how much do you earn right now, Jay?

[C]

We made about 180 last year.

[A]

Okay, so 180. And how much of that is your wife?

[C]

About 25.

[A]

Are you, like, along the way? Like, have you. What steps have you taken to realize this dream?

[C]

A ton of research, a lot of inside knowledge, a lot of friends that do it have a pretty good idea of what I'm getting into, but I have not formally started the process yet.

[A]

Okay, what would the process entail? Just to get you there. Like, let's just pretend we. We could do all the numbers and we'll get to the numbers in a second, but let's just say that you get out, you're done, and, you know, it's. I don't know, let's just call it the end of the year. So I'll give you nine months. What happens in 20, 27? Would you go into an academy? Like, what happens?

[C]

Yeah, academy lasts about four months, and then you're on a probationary status for the next eight months. And after the one year you're like, part of the civil service, protected by the union and all that? No Longer on probation.

[A]

Okay, and how much. So now we just go to 20, 28. I mean, you're making money once you're on probation, but how much does a first year once the probation is over, how much do you think you would earn total?

[C]

Both of us, we probably make about 100.

[A]

Okay. Can you guys live on 100? Yeah, yeah, no problem.

[C]

Yeah, we got pretty low overhead.

[A]

Amazing. So tell us about how much money you've saved up.

[C]

Yeah. So we've got about 1.6 million in retirement.

[A]

Wow. Is it all pre tax or is it Roth also?

[C]

It's a mix. It's probably about a third roth and then 200 of that is brokerage.

[A]

All right, wait a second. So of the 1.6 million, what's really retirement and what is non retirement? What's brokerage?

[C]

Retirement is 1.4. About a third of that is Roth.

[A]

Okay, and then 200 in the brokerage. Yeah, okay, I got it. I just want to make sure I got my, my fractions. Right. What else do you have?

[C]

We've got about 125 in like a, you know, rainy day emergency fund.

[A]

Yep. Great.

[C]

And then just like 25 grand in HSA and then, you know, a few thousand here and there. That's just like I've got 3,000 and a Bitcoin ETF. But other than the big numbers, I told you, that's, that's it.

[A]

Okay. House, how much is it worth?

[C]

It's worth about $1,400,000.

[A]

Okay. Is there a mortgage outstanding?

[C]

There isn't.

[A]

So what do you figure your expenses are? Probably five, five or six grand a month. Maybe that's why your hundred grand a year would work for you, right?

[C]

Yeah. Yeah.

[B]

Wow.

[A]

Okay. How, I mean, if you're going to make this huge change, I presume you would do it for a while. Yes. Like you would, you'd be planning to stay in this system for some period. Is there a mandatory retirement and age? I don't know even know about that.

[C]

So the state I'm in, in New England, after 10 years or age 60, whichever comes first. 10 years or age 60 in service, you can get a pension.

[A]

Right.

[C]

So the. Presumably, you know, if I just stayed in for 10 years, the pension would be like 20 grand a year. I intend on staying in for longer than that. But.

[A]

Right. You would really, you're not doing this to, for like an eight year time horizon. Clearly you're gonna, you're gonna, you're gonna try to do this. I mean, presuming your health is good and all that. What do you think? Ideally like 65?

[C]

Yeah, I'd like to.

[A]

Okay, great. And at that point, you know, I presume that the pension would compound a bit. So I'm guessing, do you know what that number is at 65? Would it be like 30 grand a year?

[C]

Yeah, I think 25 or 30. And then we'd get 3200 for Social Security. At age 65, I would. Assuming I stopped paying in right now because public service police and firemen, they don't pay into Social Security in my state.

[A]

Okay, so really interesting here. So the thing is, because you're willing to work and your wife is making a little bit of cash on the side, you guys can do this. I think it's quite doable. Mark, do you have, besides asking many questions about this, but the numbers appear to work from my perspective, don't they

[B]

for you, Mark, Based purely on what they spend each month? Yeah, it's obviously not a problem.

[A]

I mean, this seems like kind of a no brainer when it comes to the money part. Obviously there are some, some things you might want to do as you approach this period of time, which is, are you currently contributing to retirement?

[C]

Yeah, I'm doing the age 50 catch up max thing in a 401, but when is that?

[A]

So let's just think about this. Let's say the soonest you could retire is when? June 30th from your current job. Oh, did you gain your notice today?

[C]

That's a nice way to put it. Yeah, I could be done, you know, I could be done in two weeks, but there's. Okay, no rush because there's a process to this. I haven't actually gotten hired on yet.

[A]

So what's the process? Explain that to us.

[C]

So you have to do a physical test for age 50 and above in my case. So that's a slam dunk. And so that for different age ranges, it's, it's a different physical aptitude test. An interview and a panel interview with some of the higher ups, with the police, and then a background check, and then you get hired on. Then you go to the academy for four months.

[A]

Are you, are you planning to wait till you're sort of in that process before you give notice?

[C]

Yeah, I think so.

[A]

Okay. So we can protect you. Okay. Dumb question. If they find that like, oh, you know, you have rotten eyes or your feet are bad or you don't pass the physical, would you stay where you are or would you totally do something? Yeah, okay. Yeah, okay. You're not that miserable. You're Like, I hate it, but. Right.

[B]

It's interesting that, you know, if I wanted to go join the NYPD right now, I wouldn't be allowed. There's an age limit.

[A]

That's what I thought. It's amazing. They really must need people in your state. Right.

[C]

Yeah. What I'm finding is there's not an. At least in New England, most municipalities, there's not an upper age limit. That might be different in Boston proper, but not where I'm in.

[A]

Yeah, it's. So what is their age for New York, Mark?

[B]

I believe I want to say. I don't know why I know this, but I think it's like 43.

[A]

What? Yeah, we had that guy who called up from the show who's a very high ranking New York police guy. We should find out from him. That's amazing. Listen, I think you can do this. I would be careful just about my pacing of it. I always think having more money socked away is better, but, you know, especially because at this point, I presume, you know, if you're going to give your notice in the next few months, you will have already had a lot of the maximum retirement plan contributions taken from your paycheck. Right.

[C]

Yeah. I was thinking about just front loading that if I'm done in a couple months.

[A]

Yeah, I guess you could. I mean, I don't know.

[B]

Is it Roth?

[C]

Yes.

[A]

Okay, let's do it. I'm in.

[B]

As long as it's Roth. Yeah.

[A]

As long as it's Roth. Yeah. I agree. I think you're in great shape. I mean, it's such a wild story. Do you have the life. You have to carry life insurance and you need a really good estate plan. But do you have life insurance?

[C]

Yeah, we got overinsured. I think I've got like 3 million. And then I have a individual disability policy that's pretty robust. And then we just did our estate planning last fall.

[A]

All right. Do the kids know that if they go to grad school, you kind of. They're on their own.

[C]

I think they know that. Anyway, no matter what I end up

[B]

doing is your wife and kids. They're all on board.

[A]

Everyone's on board. I'm so worried. I have the anxiety building in my chest right now for this matter.

[C]

Oh, don't worry. I'll let you know how it goes.

[A]

I'll send you some. All right. All right. I really. I'm such a baby because I have great respect for how hard that job is and I worry. But that said, for your question and our purposes, I think you're golden. You guys have done an incredible job. You have got a reset. If I write the great Money reset Volume 2, I'm using this story, okay?

[C]

Oh, that would be great.

[B]

And by the way, what are you going to do if they put you on the overnight shift?

[C]

Just start drinking caffeine again?

[A]

Oh, my God. This guy was like, smooth sailing in his life and he's gonna. You see what happens? Gang, if you are called to something, you will make the sacrifice. Jay, we're lucky to have people like you. People in your state are very lucky that you're willing to do this. Get in shape. Are you in good shape already?

[C]

Yeah, definitely.

[A]

All right, so he's a bro. He's got. He's drinking protein shakes, he's in shape, he's climbing walls, he's doing all sorts of things that, you know, that they do to train the folks in law enforcement. So, Jay, good luck and let us know how it goes. I want a picture of you in your training. Okay. Send that to us. We won't post it. We don't want to out you like that. But I want to see it. Okay, you got it.

[C]

Thanks. Jill and Mark really appreciate what you do.

[A]

Well, we appreciate you. Hey, gang, are you trying to reset your life? It doesn't have to be as extreme as Jay, but if you are, get in touch with us. Go to Jill on money dot com, click the contact us button, write us a note, and of course, let us know if you'd be willing to come on the air because we love hearing stories like this, Mark. This is the payoff for us. We love this. We are such voyeurs. Right?

[B]

I'm thinking about looking into doing other things now.

[A]

Well, you better.

[B]

Yeah, that's true.

[A]

All right, gang, you could subscribe to us on the Odyssey app or wherever you find your favorite podcast. Please, please, please try to lift someone up. Change your work, change your wealth, change your life. Thank you for listening and we'll talk to you tomorrow.

[D]

Today's episode is sponsored by NerdWallet's Smart Money podcast. Ever Google a money question and end up 12 tabs deep with 12 different answers? This podcast is your shortcut back to clarity. NerdWallet's Smart Money podcast breaks down financial decisions with a team of trustees, trusted journalists, they explain the why behind decisions like investing, home buying and choosing credit cards. With clear research backed insights. No jargon, no misinformation. Make your next financial move with confidence. Follow NerdWallet's Smart Money podcast on your favorite podcast.

[C]

Apparently.