Evaluating Job Options

Summary

Podcast Summary: Jill on Money – Evaluating Job Options

Date: October 7, 2025
Host: Jill Schlesinger (CFP®, with Executive Producer Mark)
Episode Theme: Weighing a Job Offer – What’s Worth More: Time or Money?

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Overview

In this episode of "Jill on Money," Jill Schlesinger takes a listener call from Elle in Georgia, who is carefully considering a new job offer. The discussion centers around the trade-offs between compensation, benefits, and work-life balance, especially in the context of family needs and financial security. Jill and Mark walk Elle through a thorough analysis, highlighting the often-overlooked value of paid time off (PTO), vesting in pension plans, and the importance of negotiating for your true worth.

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Key Discussion Points & Insights

1. Elle’s Situation: Comparing Two Job Offers

[03:47–07:37]

• Elle, 39, currently has a job she likes with strong benefits, especially generous PTO and the ability to buy extra vacation days.
• She’s interviewing for a new position offering potentially higher compensation but with significantly less PTO (about 11 days less).
• Family time is Elle’s top priority: “Being able to have time off is really important to me.” (Elle, 03:47)
• The current role also offers a vested pension, 401(k) matching, and bonus potential.
• Her husband earns $115k (no bonus); they have a 10-year-old child.

2. Detailed Benefits & Financial Comparison

[05:44–12:35]

• Current compensation: $127k base + $15–20k typical bonus + long-term incentive stock grants.
• Current PTO: 20 vacation days, 10 sick, 11 holidays, 1 wellness, 3 volunteer days, option to purchase 10 more.
• New opportunity: Max $160k “total comp,” pension, and 5% 401(k) matching but only 20 days PTO (must be accrued) and only 5 wellness days, 9 holidays. No option to buy extra time.
• Elle and her husband are doing well with retirement savings (total over $400k in 401(k)/403(b), Roth IRAs, brokerage, and a 529 plan).
• Elle recently bought a home: $700k value, $688k mortgage.
• Both jobs offer pension plans, but Elle is already vested with five years in her current plan.

3. Non-Financial Considerations

[13:19–15:02]

• Uncertainty about travel required in the new job; “There was a discrepancy from the first round, saying, oh, it’s just once a year. And then what I’m hearing now, it may be more than once a year.” (Elle, 13:35)
• Jill’s advice: Loss of PTO plus more travel imposes a larger indirect cost, especially for someone prioritizing family.
• Security: Elle’s current company is a stable public firm; the new employer is private, “but what I have heard from friends… the last thing they will do is do layoffs.” (Elle, 14:27)
• Elle does not feel at risk of layoffs in her current role.

4. Negotiating and Knowing Your Value

[09:08, 15:02–17:29]

• Jill calls out a common self-limiting negotiation mistake: “You ding dong. …You just don’t set the bar high enough.” (Jill to Elle, 09:02)
• Elle wonders if she should ask for a higher figure, given the total compensation and PTO tradeoff.
• Jill and Mark agree that, to justify leaving, the compensation should start “with a two”: “The number that I would need … would be probably closer to, like, 225 because of everything that I’d have to give up.” (Jill, 16:29)
• Mark and Elle’s husband both side with staying put: “She’s already vested … So, I mean, if you’re asking me which way I’m leaning, I’m leaning where she is.” (Mark, 15:16)

5. Advice and Takeaways

[17:29–18:48]

• Jill recommends continuing the interview process to learn more and potentially sharpen negotiation skills: “You can always say, like, thank you so much. I don’t think I can do this. That’s fine.”
• It’s not only about higher pay: consider the hidden value in PTO, pensions, and job satisfaction.
• “You have to know the price at which you would jump. And I don’t think it’s 160, and I certainly don’t think it’s 180. It has to start…with a two.” (Jill, 16:50)
• Even if you are flattered by an offer, “change is exciting, but, you know, you’re doing…incredibly well.” (Jill, 17:12)

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Notable Quotes

• “Being able to have time off is really important to me.”
  — Elle ([03:47])
• “Eleven less days of PTO? Oh, no. That’s a lot.”
  — Jill ([04:47])
• “You just don’t set the bar high enough…We all do this to ourselves.”
  — Jill ([09:08])
• “You have to know the price at which you would jump. And I don’t think it’s 160…it has to start…with a two.”
  — Jill ([16:50])
• “She’s already vested…So, if you’re asking me which way I’m leaning, I’m leaning where she is.”
  — Mark ([15:16])
• “My first sensing is maybe I should just pull out and withdraw. But [my husband is] saying to keep going.”
  — Elle ([17:39])
• “You can always say, like, thank you so much. I don’t think I can do this. That’s fine.”
  — Jill ([17:50])
• “Change is exciting, but…you’re doing incredibly well.”
  — Jill ([17:12])

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Timestamps for Important Segments

• 03:47 — Elle introduces her dilemma: less PTO with a new job
• 05:44 — Current financial/benefit breakdown
• 08:37 — Details of new job compensation
• 09:08 — Negotiation tips and self-advocacy
• 13:19 — Questions about travel and non-salary factors
• 15:16 — Discussion of vesting, stability, and weighing the options
• 16:29 — What is your “jump number”?
• 17:50 — Advice to keep interviewing, don’t rush

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Final Takeaways

• Know all the numbers (salary, bonus, stock, pension, PTO, retirement contributions) before considering a move.
• Don’t undersell yourself when asked for salary history or expectations.
• Value non-monetary benefits (PTO, flexibility, already vested pensions) — they are hard to replace.
• Make sure the new role truly excites you or offers a significant financial step up before jumping.
• It’s always worth continuing the process for learning and possible negotiation practice—even if you don’t take the offer.

“You’re not leaving for the same money unless you’re miserable. This is your moment to take the big step up.”
— Jill ([18:20])

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For listeners facing job offers: Carefully evaluate all aspects of total compensation and lifestyle impact. Reach out to Jill if you want your own situation analyzed live!

Transcript

[A]

I want to tell you about another podcast I Can't Get Enough of. Giving Done Right is all about how to make an impact with your charitable giving and tackles the question every donor is asking, how can I make the biggest difference right now? With shifts in federal policy and funding in flux, nonprofits and civic institutions are struggling and your giving matters more than ever. You'll hear from philanthropic experts and major donors who who reveal how to maximize impact on issues from protecting democracy to supporting immigrants in crisis. Whether you give hundreds or millions, this show delivers knowledge that turns good intentions into real results. You can listen to Giving Done Right wherever you get podcasts. Today's episode is supported by what Should I Do With My Money? An original podcast from Morgan Stanley. And like Jill on Money, this podcast makes understanding money and getting advice about what to do with it less intimidating. You'll hear candid conversations from people just like you who have money questions just like yours. They talk to experienced financial advisors about their goals, worries and dreams, asking questions like can I retire early? Like really early? How do I leave a financial legacy for my special needs child? Menopause is making me feel wacky and it's shifting how I think about my money. Help. The conversations can get emotional, but they're always practical. Find what Should I Do with My Money? On your preferred podcast player and feel empowered and so supported when it comes to managing your life and finances. Welcome to the Jill on Money show. It's Tuesday, October 7th and we are here trying to provide you with a little guidance or mentoring about decisions you're facing in your financial life. Now it may not be a big one or something that you think is just sort of bubbling in the background, but maybe you would just like just a little bit of assistance and you know, there's not only one way to get to you would like to go. We understand that. So if you have something going on and you again just want someone another set of ears and eyes on a situation. Both Mark, the Best executive producer and I are certified financial planners and we'd be delighted to at least listen to what's going on and maybe help you out a bit. So all you need to do is go to our website jillonmoney.com, click the contact Us button, which is in the upper right hand corner and then a form will pop up. When you get that form, that is the email that we receive and you just, you know, if you're going to be a shy person, that's cool. Just give us a lot of detail if you'd like to join us on the program. Check the box. You can go a little bit lighter on the details because, you know, I'm very nosy. And of course, I will ask you those questions while you're on the website. Don't forget to sign up for the free weekly newsletter. And of course, you can buy my book, the Great Money Reset, which will help you take some steps to turn whatever chaos you're facing in your life, to reset it into opportunity. Okay. Today we are talking to Elle from Georgia. Hello, Elle. How are you? What's going on?

[B]

Hi, Jill. I'm good. How are you?

[A]

Great. Fantastic. What's up? What do. What can we do for you?

[C]

Where am I? No, hi for me.

[B]

Hi, Mark. How are you?

[A]

You're not supposed to be on the mic right now. It's the other show. Okay. Hi, Mark.

[C]

Am I confused today?

[A]

Yeah, I'm a little confused. All right. Anyway, he cut you.

[C]

Bye, Elle.

[A]

All right, get off. Okay, now I love Mark and he deserv. Hi. Okay, let's start again. Hi, Elle. How are you?

[B]

Good, Jill. How are you?

[A]

Doing really well. Want to say hi to Mark? Hey, Mark.

[B]

How are you?

[C]

I'm going to keep the original in, so.

[A]

Of course you are. I know you see the power he has over me, Elle. You see that? Okay, what is going on? What can we do for you?

[B]

Hi. So thanks for having me on the show and taking the time to speak with me about this decision that I may have upcoming. So I'm currently working, but I've been exploring another opportunity, and I am in the second round of interviews. And we just talked again with HR in this new opportunity about the compensation. And I just wanted to know about if this would be a worthwhile decision for me. I think one of the very important things is that I currently receive a lot of pto. And I also participate in our vacation purchase plan, which means that I pay for extra days and just family time is really important to me. And being able to have time off is really important to me. And the new position. I think I. If I'm doing the calculations correctly, I have 11 less days of PTO.

[A]

Oh, no. That's a lot.

[B]

Does it sound like a lot?

[A]

To me it does. Two weeks.

[B]

Yeah, I agree. Yeah.

[A]

All right. Wait a second. Maybe you'll make so much money, I'll change my mind. Let's do some basics before we get into the difference between the two jobs. How old are you, Elle?

[B]

I am 39. I had to think about that.

[A]

Well, congratulations. You're not yet 40. You're going to get to the fu 40s. It's fabulous. Okay. Are you married, Partnered? Single?

[B]

I'm married.

[A]

And how old is your spouse?

[B]

He is mid-40s.

[A]

Wow. It's great that you're just like I. Yeah, I used to know this. I kind of knew this. Don't know this right now. Okay, fine. Do you guys have kids?

[B]

We have one.

[A]

How old?

[B]

He's 10.

[A]

Okay, 10 years old.

[C]

Knew that one.

[A]

Yeah, I knew that one. Yeah, that, that's like seared into her memory. How much do you earn right now, Ellen?

[B]

I make about 127 yearly. Just the base pay. I have opportunities for bonus every year depending on the performance of our company. And then I also am part of the long term incentive plan. So I do get stock grants. I do have about 30k that is yet to vest and when I looked at the numbers, I get about 10k a year.

[A]

What's the bonus been? Generally? Not like, don't do the best year. Just give me like what you think you can count on. On top of the $127,000, $15,000 to $20,000. Your husband, how much does he earn?

[B]

$115,000.

[A]

Does he have any bonus potential?

[B]

No, he does not.

[A]

Okay, how about pension? Does he or you have a pension?

[B]

I do have a pension. I just vested this year.

[A]

I'm not leaving this job. Okay, sorry I just said that out loud. I may leave it. I may leave it. What's the pension? Tell me about it.

[B]

It's based, I think there's just a formula based on the years of service and then how much you make. I think it's the top amount of salary that you make that they do that.

[A]

How long have you been in this company?

[B]

It's been five years.

[A]

Okay, so right now what is the actual amount of vacation that you do get paid?

[B]

The actual amount I get is 20 days.

[A]

Oh, wait, I'm sorry.

[B]

Yes, 20 days and then 10 of.

[A]

Sick and then you buy in more.

[B]

I do buy 10 a year. I also get 11 days of holidays.

[A]

Oh my God. Do you work?

[B]

I. I get one day of wellness and then three days of volunteer or you know, education. Volunteer if you have a child.

[A]

Wow, that's pretty good.

[B]

Yeah.

[A]

Okay. Amazing. All right, so let's now compare this cushy job that you have right now that you like. Do you like or do you not like?

[B]

I think I'm resolving to. The fact as I'm going through the process is that you don't always have to love every part of your Job maybe that if it affords you the lifestyle and work life balance that you want, maybe that's where I need to.

[A]

Sit, which is great. That's why I tell people, go, look, I had someone at work say something to me like, oh, I can't believe we have to go back to work four days and five days. And they're limiting certain things. I say, you should go see what you're worth in the marketplace and you might change your mind. You might, may not maybe find a great job. Who knows? All right, let's talk about our new opportunity. I'm excited about this. So instead of you earning, you know, 120, like let's say 150 total, what is the new opportunity?

[B]

Yeah, so the new opportunity. We talked numbers just recently and they were saying that their. What they would offer me would be considered a total comp. So they asked for it during the application process and I. 130 to 160. 60.

[A]

Oh, you ding dong. Come on. You're supposed to put 200.

[B]

I just didn't know what. You just don't know going into these things.

[A]

This is such a, this is so common where we like, we all do this to ourselves. I'm calling you a ding dong. We've all done it. Which is like, you just don't set the bar high enough in which. Right. But okay, what do they come back to? Do you like, if you did they say, okay, yeah, total comp 160. Is that about what you think you might be looking at?

[B]

Well, that's the other part is that, do I need to go back to them and tell them that I'm looking for more than 160 given the fact that they provided me with the benefit sheet.

[A]

All right, so what are the benefits that they have? Let's just look at that.

[B]

Yeah, so I would. They also have pension, so that's. It seems like pretty much the same.

[A]

Okay.

[B]

Everything matches up to what I'm currently receiving except the fact of the PTO, which is 20 days. And I think you have to. The first year you have to accrue, which is not so great. And then they offer five days of wellness that you can use for volunteering or your own health or, you know, what have you. And then they have nine holidays and that was it.

[A]

They have no way for you to participate. There's no buying in the time because right now you have the 20 days plus 10 sick days and then, you know, forgetting about the extras. But you couldn't actually really buy that in. And maybe the pension is similar. Okay, this is interesting. And the retirement plan, you say there's a pension. Right now you have a 401k?

[B]

I do.

[A]

And is there a matching component of it?

[B]

Yes. My current match is 4% and their match is 5%.

[A]

Does your husband also have a retirement plan?

[B]

Yes, he does. He has a 403.

[A]

Okay. Is he a teacher?

[B]

Works for a non profit.

[A]

Okay, that's good. Okay. And your cash flow right now, just as everything stands. Everything is good for you guys with this, this kiddo.

[B]

Yeah, we're. We're really good. We're also just trying to catch up on retirement, but I feel like we're in a pretty good place. We do save a lot and put away a lot.

[A]

So let's talk about some of the savings that you've accumulated so far. So in retirement, what do you have?

[B]

So in the 403, we have 155k and we do 12% a year.

[A]

Great.

[B]

And then in my 401k, we have 200k and we max out every year.

[A]

Great.

[B]

We have a Roth IRA, 60K and 43K.

[A]

Okay.

[B]

And then we also have a 529 plan that we put in. Monthly it's 63K. And then a brokerage at 80K.

[A]

Smoking it.

[B]

Yeah, we're really just trying to catch up.

[A]

You're doing a very good job of that. Your house, do you own it?

[B]

We do own it.

[A]

How much is it worth?

[B]

Around 700.

[A]

Is there a mortgage on it?

[B]

There is a mortgage.

[A]

How much?

[B]

6.8.

[A]

Oh, yeah. That's a real number. So you bought it in the last year or so? Yeah. Okay. How much of the mortgage remains?

[B]

A lot of it.

[A]

$688,000. Okay. Okay. And so this all sounds very good. I have many feelings right now about this, so. You're doing an incredible job. Elle. You really. This is a beautiful outlook as you go through this. I want to ask you, what do you think the right number would be if you went back to them? Let's present. Pretend that you're like, you know what? I really do like this job. I really think I'd like a change. Do you feel like, is this worth going back to them and putting a number out there that's higher than what you already have? Do you, do you think that's like in your. Do you feel like you want to go through that exercise? I don't want you to go through it. If you're like, eh, I don't need to do that.

[B]

Yeah. So I have one more Conversation in my second round this week with one of the team members, and I feel like if I have a better idea of travel. So the other job requires travel, and that's where, you know, there was a discrepancy from the first round, saying, oh, it's just once a year. And then what I'm hearing now, it may be more than once a year. And so that's. To me, I'm like, well, you have less PTO and you have to travel, which takes away more time.

[A]

Yeah.

[B]

From being at home. So I think I'll have a better idea. If the travel is more than I want, I probably will not go back.

[A]

Is there a sense that you have that, like, one company has more financial stability also? I mean, like, if you're working at a place where you're like, oh, my God, the blank is hitting the fan. I need to get out before something bad happens. Is that where you are right now, or is the place where you are currently working? Feels secure. Ish.

[B]

It feels pretty secure. I think what I've been told about the other company is that what. So the company I work at right now is a public company. The other company is private. But what I have heard from friends who do work there is that if, you know, revenue is not doing well, the last thing they will do is do layoffs. So you're pretty protected in that sense. I don't feel like I'm in a place where I need to go somewhere to feel like I am not at risk for a layoff currently.

[A]

Okay. Mark, do you have a number in your head that you want to ask for? If Elle goes through and says, like, okay, the travel's okay, and this. Do you have a number in mind?

[C]

I don't know what the number would be. It's not what it is right now.

[A]

I mean, no, definitely not.

[C]

It's tough because she doesn't hate her current job. She doesn't come on here and say, I gotta get a new job. And the first words out of her mouth, basically, what's most important to her, which is the flexibility and the time off to be able to spend with her child and the family. So, you know, I know both jobs have pensions, but she's already vested in the current pension. She's got five years in. So, I mean, if you're asking me which way I'm leaning, I'm leaning where she is.

[A]

Yeah. I'm leaning stay. Unless. Unless if you end up in the next round and you get jazzed. Okay. And you're like, oh, my God, I want this. I actually do want this. Okay. If that's the case, then I do think there's an opportunity to go back to them and say, here's where I am. I am so. And it's almost like, you tell the truth, I absolutely am really excited by this offer. But when I add up all the different aspects of my other job and what you guys have, I think I probably have undershot, what I really would need to move. And the number that I would need to move would be probably closer to, like, 225 because of everything that I'd have to give up in that respect. I think that if you got a $200,000 offer, then I think it's possible that you might be like, okay, that's cool. But if you feel like what this has unearthed for you is an appreciation for the fact that, you know what, I kind of like where I am. It may not be perfect, but every job has downside. Then stay where you are, and you can keep looking. It sounds like you're obviously well sought after, but you have to know the price at which you would jump. And I don't think it's 160, and I certainly don't think it's 180. It has to start. I think it has to start with a two. I really do. But I'm inclined to stay where I am also. Like, change is exciting, but, you know, you're doing. You guys are doing incredibly well. You've got a lot of money saved. You. You've done the. What you need to do to, like, get yourself a beautiful financial foundation. I just hate to be like, the. Oh, I take a new job. Even if you made 200, they run into a problem. And then all of a sudden, the last one in is the first one out.

[B]

That makes me feel really good. And then also, your number matches my husband's number.

[A]

All right. Did he say. What did he say? Did he say 225? Two something?

[B]

He said around 200. He did say. You know, I think because I. My first sensing is maybe I should just pull out and withdraw. But he's saying to keep going.

[A]

I think keep going anyway, just to see what. See the process through. You can always say, like, thank you so much. I don't think I can do this. That's fine. What's the difference, right?

[B]

I guess so. Yeah.

[A]

It's not bad. It's totally not bad. And if you have the next conversation and you're like, this is a hard no, then you can pull out. You can say, like, oh, they're like, okay. By the way, you have to travel one week every quarter order, and you're going to be like, how about. No, that's fine. And you can just say like, wow, that's more than I thought. Just. See, it's interesting to learn, right? It's a great experience. Next time, you'll know that if you're going to start this process, you will start with a higher number you give. You're not leaving for the same money if. Unless you're miserable. So I always try to say, like, this is your moment to take the big step up, right? And that's where you are. But you're in really good shape, Elle, and you guys have done a great job, so I'm really psyched for you. And let's play it out a little bit more.

[B]

Okay, sounds great.

[A]

All right.

[B]

Thank you.

[A]

I love these. I love the analysis. So if you are like Elle, and you're looking at a new job offer and you want to know, like, hey, does this make sense for me or not? Get in touch with us. And if you're starting the process of looking for a job, just remember there's a lot of risks. Some people are just going out there and doing it because there's risk of where they are. That's why I asked that question. If there's something going on for you and you're nervous or you've got some, you know, just. Just need a little bit of coaching on how to move, weigh different offers against one another and what things are worth. Get in touch with us. Go to jillonmoney.com, click the contact us button and write us a note. And if you want to come on the air, it's much better if you come on the air with these kinds of questions, because then we can start to get a sense of, well, is the company in a good shape or bad shape and those kinds of things. So come on the air. It's very cool. While you're on the website, check out all of the content that lives there, including our subscription service. It's called Jill on Money Live, where you have access to quarterly live webinars, the back catalog of those webinars, bonus audio and video content, all for 45 bucks. For the next 12 months, you can subscribe to us on the Odysee app or wherever you find your favorite podcasts. Don't forget, forget to put your hands, metaphorically, on someone's backers. Give someone a hug, get permission, because it's a nice thing to do. Change your work, change your wealth change your life. Thank you for listening. We'll talk to you tomorrow. Hey gang, here's the thing about wine. Some of the best bottles are not sitting on a store shelf. They're being crafted at small, independent wineries. But those wines can be so hard to find sometimes. I wish I had a personal sommelier to guide me to find the best wines I normally wouldn't be able to access. Where's that handcrafted Pinot that I've been craving? Well, Psalmsation's expert team seeks out incredible wines from top independent producers. These are bottles that you will not find in stores and on shelves. And they aren't mass produced wines. They're handcrafted with care, using pure ingredients and meticulous winemaking. Whether you want a single bottle, a guided tasting experience, or an entire wine club membership, Psalmsation makes it easy to elevate your wine experience. Shop their [e-mail] jillonmoney that's somsation.com Jill Jill on Money hi, I'm Nancy Cartwright.

[D]

You may know me better as the voice of Bart Simpson on Simpsons Declassified. We're diving into the mysteries that keep the Simpsons forever young. Have you ever wondered how the Simpsons regularly predicts future events? Who better to ask than the show's creators, performers and writers, the celebrity guests? Be sure to follow and listen to Simpsons Declassified wherever you get your podcasts.