Keeping All the Balls in the Air

Summary

Jill on Money with Jill Schlesinger

Episode Title: Keeping All the Balls in the Air
Original Air Date: December 4, 2025

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Episode Overview

In this candid and relatable episode, Jill Schlesinger is joined by John from Pennsylvania, a high-earning professional and family man struggling with the stress of balancing life, work, and complex financial decisions. The discussion centers on the emotional weight of financial uncertainty, the reality behind “having it all together,” and the practical next steps for those who feel overwhelmed by managing their wealth, planning for retirement, and facing the next life chapter.

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Key Discussion Points and Insights

1. The Challenges of "Keeping All the Balls in the Air"

• John's Introduction (04:36–06:30):
  John articulates the universal struggle of juggling career, family responsibilities, household maintenance, and increasingly complex finances.
  • He describes the overwhelm of supporting a family—with his spouse primarily focused on raising kids—and the pressure that comes with being the main breadwinner.
  • Quote:

    "It's hard. It's hard to keep all the balls in the air. So, you know, working, having a family, making sure your kids are safe and bring them up properly, spending time with your spouse, paying bills, mowing the lawn, you know, making sure that the mailbox is straight... And then you Add the financials and it's like, oh my gosh." – John (04:36)

  • John expresses empathy for single parents, admiring how they “rise to the occasion.”

2. John’s Financial Situation Laid Bare

• Assets, Income, and Retirement (07:07–10:53):

  • John is 55, as is his wife; their children are in their 20s, with one working and one about to graduate college.

  • Household income is roughly $350,000/year ($335,000 his, $15,000 wife's part-time).

  • Retirement assets total about $1.3 million, with ~$600k in traditional accounts and $115k in Roth accounts.

  • Substantial non-retirement assets: $3 million in a brokerage account, most of which John has self-managed with some self-admitted “chasing the next thing.”

  • Home is paid off, valued at approximately $650,000. They are considering a nearby move to a more remote area with a higher price point, budgeting $200,000 from savings for this purpose.

  • He maintains a large emergency fund, nearly $560k in cash, driven by job security worries.

  • Memorable Moment:
    Jill reacts lightly to John’s confessed investing jitters:

    "Oh, you're that guy. That's all. Dividends are interesting. Let me open up a dividend fund... Now it should be in index funds. Let's get into index funds. What about international?" – Jill (08:47)

3. Redefining What’s “Enough” and Planning Retirement

• Spending Needs and Moving Goals (10:15–12:00):
  • John tracks expenses closely with his wife, estimating core costs at $65,000/year excluding health insurance.
  • With anticipated ACA health insurance, he projects $90,000/year after taxes to cover everything.
  • Jill probes his willingness to work part-time in the future, possibly in enjoyable settings (e.g., REI, Trader Joe’s), noting that part-time jobs often bring unexpected time commitments relative to pay.

4. The Emotional Reality and the Need for Professional Guidance

• Jill’s Core Advice (12:51–15:43):

  • Jill tells John he’s done “an amazing job” and, despite his anxieties, is in “very good shape”—financially secure and free to choose his next chapter.
  • She urges him to give himself permission to step back at work, potentially seek less stressful part-time or consulting roles, and, most importantly, to hire a real financial planner (not just an investment manager).
  • Her concern is less about the money and more about John’s ongoing emotional distress (“You are the perfect type of person to hire a financial planner. You really are. Because you've got a pile of money. There's really nothing bad that's going to happen except what you do to yourself.” – Jill (13:47))
  • Jill emphasizes the importance of a holistic planner who can address both financial and life questions; someone who can “take the financial baggage off your shoulders.”

• Notable Quote:

  "You have saved so much money that you have now bought yourself the ticket to being able to explore what that next chapter is. You really have." – Jill (15:15)

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Notable Quotes & Memorable Exchanges

• On parental pressure and empathy:

  "Sometimes I think about the single parents out there... My heart goes out to those people that just don't have that support.” – John (06:30)

• On investing self-doubt:

  “I've done a good job messing that, that side of it up too.” – John (08:27)

• On financial anxiety despite strong savings:

  "For all of your, your anxiety and self doubt, you've done— and you and your wife have done— an amazing job." – Jill (13:34)

• On what a financial planner can and can’t do:

  “Here's what they cannot solve for, they cannot solve for if you haven't saved enough money. You have saved enough money.” – Jill (15:00)

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Important Timestamps

• 02:58 — Jill welcomes listeners, invites financial questions, outlines ways to contact the show
• 04:08 — John introduces his life and money challenges
• 07:07 — Breakdown of John's family and financial snapshot
• 08:27 — Discussion around self-directed investment pitfalls
• 10:15 — Housing plans and moving goals
• 11:25 — Social Security benefit review and retirement budget
• 12:51 — Jill’s key advice: reassess, permission for change, seek professional guidance
• 15:15 — Empowerment for next chapter: “You’ve bought yourself the ticket…”

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Tone and Style

Jill delivers her trademark blend of empathy, humor, and practical, actionable advice. The conversation is honest, supportive, and peppered with occasional light-hearted teasing (especially about John’s investing style), ultimately centering on self-kindness and the value of seeking trusted professional help.

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Summary Takeaways

• Financial complexity and stress are normal—even for highly successful savers.
• Big financial wins can’t always alleviate the emotional burden of money management.
• Giving yourself permission to change, seek support, and pursue new lifestyles is critical.
• Professional, holistic financial planning can offer relief, structure, and peace of mind for those ready to move into new phases of life.

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For more resources or to submit a question for Jill, visit jillonmoney.com.

Transcript

[A]

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Welcome to the Jill on Money show. It's Thursday, December 4th, and we are here trying to help you make sense of whatever financial question is driving you crazy or maybe just kind of on your mind. It doesn't have to be extreme. It has to be anything that comes to mind as you listen to this program, especially if something that we say is sort of, kind of applicable to you but you're not sure. We'd love to hear from you. We'd love to hear you in your own words tell us what's going on, and then maybe Mark and I can try to guide you a little bit towards wherever it is you say you'd like to go. So if that's you, just go to the website, jillonmoney.com, click the contact us button, write us a note if you want to join us on the air live, which we love. It's really so much fun for us. Check the box. Mark will arrange everything while you're on the website. Don't forget, sign up for the free weekly newsletter. And in fact, check out all of the free resources that live on the website. We've got another podcast called Money Watch. We've got a radio show called Jill on Money. There are videos, there are resources. All there. Jillonmoney.com that is the key to everything you will need, at least from us. Okay, Right now, let's talk to John from Pennsylvania.

[B]

Thank you just for your time and what you do and the service that you provide. I really appreciate your candidness and your intelligence. And I love when Mark sort of comes behind the curtain and gives his two cents, too. It's nice to have another opin opinion there. Not that Jill's opinion is not right all the time, but.

[A]

No, it's definitely not. And he definitely corrects me many times. So it's good. We're. We're a good team. So tell me what's up.

[B]

I've been trying to do the right thing financially in life and everything, and what I found is it's hard. It's hard to keep all the balls in the air. So, you know, working, having a family, making sure your kids are safe and bring them up properly, spending time with your spouse, paying. Paying bills, mowing the lawn, you know, making sure that the mailbox is straight. You know, just silly things, but takes so much time. And then you Add the financials and it's like, oh my gosh, okay, you gotta bring in some income, you gotta get the right job. You've got to save for retirement. How about 529s? What about taxes? What about, you know, what about medical? What about this? It's just so complicated. And you get into HSAs. What should I do with HSA? Should I be saving there? There's so much complexity and when, when you hear the financial people talk, it sounds so simple. But when you actually do it and go through life and try to keep everything in balance, it's hard. We took a, not that we're very traditional people, but we just took a traditional role that my wife's going to stay at home and focus on the kids. I'm gonna, you know, I'm gonna be the career guy and bring in the income and there's some benefits there that she gets to focus. There's some downside too that she loses some of her self in not working. And I have all the pressure to bring in the income and, and support everyone and, and that adds to the stress too, you know, and sometimes I think about the single parents out there.

[A]

I know it's like too much. Mark and I were just, we had talked to somebody, we're like, how do they do it? It's amazing.

[B]

You know, people rise to the occasion and you don't really know what you're, you're, you can do until you're put in those situations. But God, my heart goes out to those people that just don't have that support.

[A]

Okay, John, how old are you?

[B]

55.

[A]

How old is your wife?

[B]

55.

[A]

How old are your kids?

[B]

They're in their 20s. One is launched in a career, first year, I think he's launched. The other one is finishing up college. Undergrad will be done in April.

[A]

Okay, well, that's good. How much do you earn, John?

[B]

Me personally or household?

[A]

Well, you said your wife doesn't work.

[B]

She works part time now.

[A]

Okay, how much does she earn part time?

[B]

$15,000.

[A]

Okay, and what about you?

[B]

$335.

[A]

Here comes the hate mail. Okay, 335. How much are you putting into retirement? Are you maxing out?

[B]

I've got some unique things. I think that I can't max out certain things because of the way our company is structured.

[A]

You're a highly compensated employee, as they say. How much money do you have in retirement right now?

[B]

How about that in retirement? $1,300,000.

[A]

And that's in a pre tax retirement plan.

[B]

It's a combination of 600,000, 401, $600,000 traditional, which was some rollover also. And there's like $115,000 in Roth.

[A]

Are you entitled to any pension? No. No. Okay, on this 335, you've got this great pile of money in retirement. Do you have non retirement assets as well?

[B]

I do. I've got.

$3 million in a brokerage account.

[A]

Do you do it yourself or do you have someone manage that for you?

[B]

No, I've done a good job messing that, that side of it up too.

[A]

So what do you mean? Say more about Ben messing that up?

[B]

You know, I've been doing, I've been investing for 25 plus years and I sort of don't know what I'm doing. So I sort of chase one thing and then say, oh, that fund's no good. Let me open up another fund.

[A]

Oh, you're that guy. That's all.

[B]

Dividends are interesting. Let me open up a dividend fund. Well, and then it's like this, you know, last 10 years, it should all be index. I'm like, okay, now it should be in index funds. Let's get into index funds. What about international? Oh yeah, let's get some international in there. How about small cap?

[A]

So let's just do a few more details here. You own your home, John.

[B]

Correct. Own it outright. So we're about 650 and dropping daily.

[A]

No, don't be ridiculous. Are you going to stick around?

[B]

We're sticking around. We want to stick around the area, but we want to get out of the neighborhood where we raised our kids. So we want to go more remote. But that's within a 10 mile radius. So of the 3 million brokerage, I've earmarked 200,000 in cash for the house quote. Downsize.

[A]

What are you talking about? Like you, you wait a second. You're going to sell a 650, you're going to move slightly outside and you're going to end up spending 850 by.

[B]

The time you got moving costs, closing costs, realtor fees.

[A]

I mean, come on, can't you just use the. Whatever you sell. Here's the first rule. Whatever you sell, the proceeds. Like use that for whatever the next house is. And that's it. That's your top end.

[B]

Unfortunately, in this world, in this area, it doesn't work because people are building these monster houses in these remote areas and there's no land. And to get something reasonable, even on the low end, it's going to cost. Yeah, it's going to cost 750, 800.

[A]

Let's talk a little bit more about what do you actually need to spend? Like when you. You got $335,000, you've saved a bunch of money. Do you have money just in cash, just an emergency reserve fund, or is that a part of the brokerage?

[B]

Again, there's. It's part of the brokerage, but there's always a rub to what I do. So in.

I never felt comfortable with my security of my job. So we've always kept a couple years of cash on hand, and in that case, we've always kept a couple hundred thousand liquid. Not that we spend a hundred thousand a year. It's just. It was a round number that we were comfortable with.

[A]

Okay.

[B]

I added a couple hundred thousand for the house, so I'm sitting on 560,000 in cash.

[A]

When you say of the 3 million. Okay, good. That's fine. So when you look at your Social Security benefit at your full retirement age, which is probably 12 years from now, John, what is that benefit? Do you know?

[B]

4057 is 70. 3268 is 67. 22. 72 is 62.

[A]

All right, 3300. So you're telling me you think you need 10 grand a month to live on, Is that right?

[B]

No, my expenses are tracking. We put them in a spreadsheet. I twist my wife's arm every month to do this, and she's been agreeing with me. 65,000 is the expenses without health care. And I'm anticipating if I go on ACA, maybe 20 to 25,000 in health care expenses, to be conservative.

[A]

Yeah, I think that makes sense. So we're going to say 90 grand.

[B]

Yeah, and then add some taxes.

[A]

All right, so 90 grand net is probably what we're looking at. Would you work part time? What if you. What if you could work part time now, could I get you to just, like, cover some of the moolah that you need? Can you do something part time or not?

[B]

Yes, I can. If it's is related to some of my sporting goods addictions, yes, I. Yeah, right.

[A]

Go work at like, REI or something. Get your stuff for free.

[B]

Well, I. I like food and I like sporting goods. So I was thinking, you know, Trader Joe's or A RE because they offer benefits.

[A]

Exactly.

[B]

I envision me doing that. And I'm not a kind of guy that can leave anything undone. So, you know, I'm. I'm there and this needs to be done. So next thing I know, I'm Working there eight to ten hours a day. And I'm going to look at my paycheck and I'm going to say, what the heck did I do?

[A]

You need a shrink for that. Which I'm happy to do, but I'd be like your kick your ass shrink. Listen, here's what I want you to think about. Take a deep breath with me, please. You're in very good shape, okay? You really are. You saved a boatload of money. You almost can't screw this up from this point. You almost can't. You really got this. You have plenty of money. Even if I took out, even if I took out of your 3 million, if I said, all right, it's really not 3 million, it's actually 2.6. All right? Because we're going to do the house and you like some security, that's fine. Your money will be able to create this income. I want to tell you what you really, I think you really do need. I think you need an advisor. I really do. I think you're driving yourself crazy. I mean, you have a lot of freaking money, John. You have a lot of money. And for all of your, your anxiety and self doubt, you've done. And you and your wife have done an amazing job. You have, okay, the kids are almost done like this. Got one more in college. You're done. This is what I think you should give yourself permission to do. First of all, you're fried. You're clearly fried. You need to take a break. You need to talk to your boss. You know, and we're not doing this this second, but I'm just saying maybe next year talk to your boss and say, I'm fried. I love you. You've been great to me. And maybe there's a question about whether you could do something consulting ish for this company. Maybe not. Who knows? Before you have this conversation, you start looking around and you say, let me just get a fun job. Let me just do something, just something for fun. That's it. And you kind of plan that out. You're going to have to free up money to help pay for your bills. That's fine. But all of this is to say you are the perfect type of person to hire a financial planner. You really are. Because you've got a pile of money. There's really nothing bad that's going to happen except what you do to yourself. But your emotional life, in retrospect, you look at this, you say, oh, I did this. I did terrible. I look at it, I'm like, you guys are Amazing savers. I'm sorry, you're driving yourself crazy. But you need help. You need help to manage it because it's too much. And so you don't just need someone to manage your money, because that's dumb. You don't want to pay for that. You need a real financial planner who can help you weave together all of your needs and wants, and you're paying that person. I know that's a drag, but this is something you should absolutely consider. You need to get a human being to help you. You just need that. That's, to me, like, the real takeaway from this whole conversation is you're in very good shape and you don't believe it when you talk to an advisor. Here's what they cannot solve for, they cannot solve for. If you haven't saved enough money, you have saved enough money. You have and you're willing to work. You're not saying, I'm never, ever going to work again. You don't have that mentality. You don't want to work like you are working right now. You want a next chapter, I get it. You want a next endeavor, I get it. And I hear how fried you are. But you have saved so much money that you have now bought yourself the ticket to being able to explore what that next chapter is. You really have. If you need a little bit of guidance, if you need some coaching, mentoring, if you need us to just sort of take the financial baggage off your shoulders, we'd love to help you out. Just go to jillonmoney.com, click the contact us button, write us a note, and of course, check the box. If you'd like to join us on the air, you can subscribe to us on the Odysee app or wherever you find your favorite podcasts. Don't forget to lift someone up. Change your work, change your wealth, change your life. Thanks for listening. We'll talk to you tomorrow.

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[C]

It's Vaughn Miller, Super Bowl MVP chicken farmer and now host of Free Range. This is a show where I go off the field and off the street script. We're talking what's hot in music, film, trending news and everything blowing up your feed. If you love football, you'll feel at home. But if you're here for the vibes, the Internet deep dives the conversation. This is your podcast. Join me every Wednesday. Follow and listen to Free Range with me Von Miller everywhere. You get your podcast.