Are We Really Ready to Retire Early?

Summary

Jill on Money – Episode Summary

Episode Title: Are We Really Ready to Retire Early?
Date: March 10, 2026
Host: Jill Schlesinger
Guests: Sonia and Michael (Callers from Denver, Colorado), commentary by producer Mark Telarisio

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Overview

In this episode, Jill takes a live call from Sonia and Michael, a Denver couple in their late 40s/early 50s, who are debating whether they’re financially and emotionally ready to become “work optional” and retire early. The discussion explores their finances in detail, covers couples’ dynamics around major life decisions, and offers practical, jargon-free advice about early retirement—especially for high-earning, high-saver families. The episode dives into the realities of early retirement, the subtle complexities of spousal expectations, and the importance of planning for both finances and purpose.

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Key Discussion Points & Insights

1. The Couple’s Primary Question

• [03:57] C (Michael): "We would just like to know if we're in our current financial situation. It's an option for us to be financially independent, basically be work optional."
• Sonia expresses doubt, Michael is ready to quit now.
• Jill: “I can also be a marriage counselor as well...” ([04:41])

2. Financial Snapshot & Assets

Jill methodically builds the couple’s financial landscape:

• Ages: Sonia (49), Michael (54.5) ([04:48])
• Incomes: Sonia ≈ $100k; Michael's base and bonus ≈ $390k ([14:45])
• Retirement assets:
  • Roth (tax-free): $600,000 ([05:40])
  • HSAs: $26,000 ([05:40])
  • Traditional tax-deferred: $1.2M ([05:56])
  • After-tax brokerage: $1.9M ([06:40])
  • Cash/money markets: $200,000 ([06:40])
  • Additional vested RSUs: $450,000 ([06:40])
• Real Estate:
  • Primary home value: $900,000 (paid off) ([07:18])
  • Rental property: $500,000 (net ~ $1,500–2,000/mo) ([07:32–07:55])
• No mortgage, no rich parents, no caretaker obligations.
• 529s fully funded for both children’s college ([06:15])

3. Spending & Early Retirement Math

• Current monthly spending: $9,000–$12,000, potentially higher with healthcare and kids ([08:05–08:48])
  • “Let’s say 12 grand a month. Let’s call it.” — Jill ([08:48])
• Discussion of healthcare costs and ongoing travel/lifestyle needs.
• Jill pushes for realism in post-retirement health expenses.

4. Income Bridge to Traditional Retirement Age

• Expected future pension: $1,300/month at age 67 ([10:14–10:34])
• Estimated Social Security at 67: Michael $3,300, Sonia $1,630 ([11:32–11:43])
  • Total household SS + pension at 67 ≈ $5,000/mo + $1,300/mo

5. Retirement Drawdown Strategy

• Game plan:
  • “Let’s use that [brokerage/RSU/cash] money for some period, then the pretax accounts, then at 67–70, rely on Social Security and pension.” — Jill ([12:16–12:29])
• Considering the IRS ‘Rule of 55’ for 401(k) withdrawals ([12:29–12:44])
• Michael floats idea of using cash as “runway” in market downturns.

6. The Emotional Side & Spousal Alignment

• Sonia: Uncomfortable with quitting if Michael stops but “I do like working. But I don’t want to work full time if Michael is not going to be working.” ([09:19–09:25])
• Michael: “I think I'm not uninclined to work. I just want to figure out if we have to.” ([13:05])

7. Expert Opinions

• Mark (Producer) weighs in:
  • “They could probably do this. But I also think it’s very, very close... with the health care expense, it’s close. It’s probably too close for me.” ([13:31])
• Jill agrees and suggests improving liquidity by selling the rental property:
  • “$1,500 a month is OK. It’s not great on a half million dollar investment.” ([13:44])
  • “Even if the numbers work, you guys have to feel good about this together.” ([14:15])
• Jill’s Proposal:
  • “What would make me feel better: Sell that rental, get that $500,000 to work... Also, consider both working part-time for a while, especially for keeping health care covered and softening the transition.” ([14:15–14:45])
  • “When you said you’re not on the same page, this is not about money. This is about philosophically, how do we view the next five years?” ([15:37])

8. Mind the “Work Optional” Gap

• Transition plan favored:
  • "If you were to work full time for three more years, this is a lot easier." ([16:54])
  • “Do that for a couple of years, and then, boom, you’re done.” ([17:23])

9. Family & Legacy Concerns

• Sonia is emotionally attached to the rental property: dreams of passing it to kids ([18:00])
  • Jill: “Come on. Damn kids... It’s better for the kids and your lives for you to have liquidity than to have a piece of property to pass down.” ([18:10])
  • Suggests primary home ($900k) is plenty of legacy ([18:20])

10. Key Advice for Listeners

• Liquidity and flexibility are crucial—don’t get locked into illiquid real estate or overly rigid plans.
• Spousal alignment is as important as the spreadsheets.
  • “This is not about money. This is about philosophically, how do we view the next five years?” ([15:37])
• Early retirement is possible, but when it’s “close,” caution, flexibility, and continued earning (even part-time) make a big difference.
• Estate planning and regular document reviews are a must for those approaching retirement.

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Notable Quotes & Memorable Moments

• Jill, on early retirement nerves:
  • “If you’re making a half million dollars a year together, going from a half million to zero is a lot.” ([14:48])
• On family consensus:
  • “Even if the numbers work, you guys have to feel good about this together.” — Jill ([14:15])
• Jill, pragmatic:
  • “I would sell that rental property and get that $500k and get that to work in a different way... Having the liquidity is important.” ([13:44])
• Jill’s philosophical zinger:
  • “This is not about money. This is about philosophically, how do we view the next five years?” ([15:37])
• On passing down property:
  • “Come on. Damn kids. Good Lord, Mark. What am I to do with this?” — Jill ([18:10])
• Mark, lighthearted:
  • “I can just envision Sonia, like, giving him the elbow throughout this whole time. See, I told you so.” ([20:13])
• Jill, on conservative planning:
  • “When it’s close, I’m going to err on the side of being more conservative because I’m a wimp.” ([20:07])

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Important Timestamps

• [03:54] – Call begins, Sonia & Michael introduced
• [04:25–05:56] – Ages, incomes, retirement accounts
• [06:06–06:29] – Children and college savings
• [06:40–07:14] – Brokerage, cash, RSUs
• [07:18–07:55] – Real estate holdings and rental income
• [08:05–08:48] – Monthly spending, healthcare cost discussion
• [10:11–11:43] – Pension & Social Security estimates
• [13:31–13:44] – Producer Mark’s conservative take
• [14:15–16:54] – Jill’s proposal: sell rental, work part-time, ease into retirement, get on the same page
• [18:00–18:47] – Emotional debate about passing real estate to the kids
• [20:07–20:13] – Jill on the value of being conservative with close decisions, Mark’s quip about spousal nudging

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Final Advice & Tone

Jill’s Style: Warm, honest, slightly teasing, direct and practical—balancing the spreadsheets with life realities and relationship needs.

• “Take a deep breath. You can cancel the marriage counseling session. I feel like we’ve gotten to that place.”
• “What I really want to know is how this story ends.”

Big Takeaways:

• Early retirement for high savers is possible, but only just in this couple’s case; extra caution is recommended.
• Emotional readiness and teamwork are just as important as numbers.
• Liquidity provides flexibility and peace of mind.
• Part-time work and gradual transitions may be the smarter route.

Actionable Listener Advice:
“If you and your spouse are going through something like this, you want to try to get on the same page, get in touch with us. Go to jillonmoney.com, click the Contact Us button...”

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(Summary skips advertisements, website intros, and closing promos.)

Transcript

[A]

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[B]

Hi. Thank you for having us.

[A]

Of course. What's up?

[C]

We would just like to know if we're in our current financial situation. It's an option for us to be financially independent, basically be work optional. And I think it would be great to get your you guys input on that. And yeah, that's basically okay.

[A]

Wait a second. So you want to just. You're done? Are you fried? Are you happy? Are you like, where are you in the life cycle? How old are you? What's going on?

[B]

So I must say that I'm not sure we're on the same page with my husband. And I think that's the main reason why we are calling you. Also, Michael thinks we are ready to retire. I'm not 100% confident that we can, and that's the main reason why we're calling you.

[A]

Well, then that's good because I can also be a marriage counselor as well as. Okay, Sonia, how old are you?

[B]

I'm 49.

[A]

Oh, you're young. Okay. And Michael, how old are you?

[C]

54 and a half.

[A]

Okay, the halves. Boy, here we go. You guys are both working full time?

[C]

Yes.

[A]

Sonia, how much do you earn?

[B]

Around 100k.

[A]

Do you use a retirement plan through work?

[B]

Yes, we do. Both of us.

[A]

Okay. All right. How much are you contributing right now into retirement, Sonya?

[B]

The maximum amount in my 401k and also I do a backdoor IRA, also the max amount.

[A]

Okay, great. So you're saving a lot of money, so you're doing a backdoor Roth. How much money's in your. In your Roth and how much is in traditional?

[C]

As a family or doesn't matter.

[A]

However you guys want to tell me you get, if you have the total, give me the total. Otherwise you can bang it out.

[C]

Sure. It's tax free. Is a little more than 600,000 in Roth 401K and Roth IRAs, and then around 26,000 in HSAs.

[A]

Okay, what about traditional tax deferred?

[C]

Let's see. So 1.2 million, roughly. A little more. Yeah. So that's 401 IRAs combined.

[A]

Okay. You guys have kids?

[C]

Yeah, two.

[A]

Yeah. How old are they?

[C]

One is a freshman in college, the Other one is 16, so junior high school.

[A]

Oh, God, you're in it. What about saving for college? Have you had. You have some money set aside for that?

[C]

Yeah, we have 529 fully funded for four years of in state college.

[A]

Oh, gosh, you're good. Okay, so that gives you a lot of comfort there. Okay. A lot of money saved already for retirement. Any money in brokerage accounts?

[C]

Yeah, so we have in after tax accounts, roughly 1.9 million. So that's like 1.2 roughly. In a joint brokerage, then we have a little more than 200,000 in money markets. Just cash, basically. Other cash, just checking and so on. 1:35,000. And I work in big tech and I get like RSUs and basically a slot plan. We have around 400, depending on which. What time of the day you look, it's around 450,000.

[A]

Okay, got it. Okay. And your home, you own a home, correct?

[C]

Yeah, we. We do. No, no mortgages. We have 900,000 roughly for is what our home is worth right now. And we also have a rental, if that's important. Yeah, so paid off.

[A]

So how much does that. Is that worth and how much cash flow does it generate?

[C]

So it's 500,000 roughly, and like gross year, 35,000.

[A]

What about net? Let's do net net.

[B]

I will say we every month we have about between 1500 and 2000 remaining after all the.

[A]

Okay, yeah, all the stuff. Okay. What about the most important question that I like to ask, which is how much do you spend?

[B]

We spend around $9,000 a month. Yeah, that includes everything.

[C]

Yeah, 108, 110. That includes tax, like real estate tax, Travels, everything.

[B]

About 9,000amonth.

[A]

If you were both to quit, what about health care? Would you just pay for that? Should we just add Another thousand dollars a month into your spend. If you were to both call it

[C]

quits, I would say that's probably too low because we still have to take care of our kids.

[A]

Oh, yeah, I forgot about them.

[C]

I would say let's say 11, basically. What? What? I'm guessing, and I don't. I don't know, depending on, you know, how we can manage income. But worst case, we're thinking about 30,000 a year.

[A]

So let's say 12 grand a month. Let's call it. Okay, then instead of nine. Is it the case, though, just so I get this straight, because it sounds like Michael's like, yeah, let's quit. Sonia, do you want to keep working? Because obviously, if you were to work at least even for some period of time, we could kind of get the health care paid for. Right?

[B]

Yes.

[C]

It's a bit of contention here.

[A]

Why? Why? Because you're like, why should I work if you're not going to? You so and so.

[B]

Exactly.

[A]

Okay, I understand that. I understand it. But do you like. But do you like working, Sonia?

[B]

Yes, I do. But I don't want to work full time if Michael is not going to be working. And if he doesn't work, we'll most likely travel a little bit.

[A]

Not why you have a high school junior or senior.

[B]

Yeah, we forgot to mention we don't want to retire tomorrow, obviously. So we're thinking about. Or is thinking about in a year.

[C]

Well, at the latest, I think. I think.

[A]

You are fried, man. You are done. Is that it? That's what's happening. Wait, Michael, before you go on, what happens to your RSU's when you say, I'm out of here? Does the company. How does a company treat those?

[C]

What I. The amount I gave you is what's already vested.

[A]

Okay, Sorry. Got it. All right. And no pensions available for you.

[B]

Yes.

[C]

Well, at 65. Right.

[B]

Yeah.

[A]

Right. Tell me about that. What's the. The pension amount?

[C]

So it's a little like where we have some around. I want to say a thousand three hundred combined per month, starting at various, like, when we're all 67 or so on.

[A]

Okay.

[C]

Phases in. Right.

[A]

Okay. Okay, got it. So 67. $1300 a month, plus there'll be some Social Security, but we got bigger fish to fry because we got a dozen years where you got to figure out how you're gonna live.

[B]

Right, Exactly.

[A]

Is there anything else that we should know about in terms of your balance sheet, in terms of, like, anything else? Like, do you have to take care of parents or do you have Rich parents who are gonna leave you piles of money.

[B]

No, we don't have rich parents, but I wanna add that. So we calculated that in a year we should have an additional roughly $280,000. That's combined savings and what we put in our retirement accounts.

[A]

You guys looked at your. Let's just use 67. We can always wait till 70. But Social Security at 67. Do you have that number?

[C]

Sure. For me it would be 3,300. If I would until the end of the year for sonia would be 1630.

[A]

Roughly like five grand in Social Security. Thirteen hundred dollars a month. These are future dollars. However. I'm listening. One of the things that's always challenging is we talk about things in the future. It's not like necessarily exactly where we are today. And what you're saying is that, you know, you've got this, you'll probably have. Let's just call it $2 million in brokerage cash RSUs. Right. And you'll. Is the game plan like let's use that money, let's live on that money for some period of time and then let's start pulling money out of our pre tax accounts to get the money out. Live on that. And then when we're 67 or 70 years old, everything else will support us. Is that kind of the game plan?

[C]

I think the exact game plan is to, you know, to be discussed. But yeah, in, in principle. I mean, yeah, 55. I mean in my 55th year. So I could even access the. Another 401k rule of 55.

[A]

Yeah.

[C]

Just sequencing it and we. We have a fair amount of cash that we are basically trying to use as a Runway in case the market goes down. So yeah, I guess pretty much.

[A]

And there is zero income or hey, I'll do something. I'm a tech guy who's burnt out, but I certainly can do.

[C]

I think I'm not uninclined to work. I just want to figure out if we have to.

[A]

Mark Telarisio, you're listening to all of this and besides chiming in with what you know, I'll say, which is they're so young, how could they stop working? What do you think about Sonia and Michael's ability to have the. Again to stop without feeling like they had to make money.

[D]

They could probably do this. But I also think it's very, very close. Especially with the added health care expense. If not for that, I would be a bit more confident. It's close. It's probably too close for me.

[A]

It would be too close to me. I'll tell you one thing that would make me feel better. I'd sell that rental property and get that 500 grand and get that to work in a different way. Because I don't think that that rental Property is like $1,500 a month is okay. It's not great on a half a million dollar investment. Do you know what I mean? I think of it as, it would be great if you could maybe come to a nice place together that you both feel confident about. Now, Sonia, you like what you do. Michael, you don't. So is it possible that we could say, like, hey, Michael, let's get this younger kid graduated from high school. Let's just get through that. And then let's come to a place where we're like, okay, between the two of us, we're gonna make some amount of money. Or maybe one of us, maybe Sonia, maybe you would wanna keep working. Not for the insurance. Cause you want to. And then potentially after your income goes down. Cause at this point, Michael, how much do you earn?

[C]

Base and BONUS Together, around 390.

[A]

I mean, if you're making a half a million dollars a year together, going from a half a million to zero is a lot. So it would seem to me that even if you had like, like 18 month Runway, you could say, okay, we're gonna like stockpile some money. We're gonna make sure that we do what we gotta do. But then I think you guys do need to work on this idea about like, kind of what's happening in the interim. Like, if you're 56, Michael and Sonia, you know, you're 50 or 51, you know, what is it gonna make? What's gonna make you guys feel happy? I think that if you sell the rental property, that this works a lot better for me because I think having the liquidity is important. But the other big looming thing is that even if the numbers work, you guys have to feel good about this together. You really do. And so what would be great would be as if you could say, well, what is it that each of us really wants here? So you might be like, I want to work, but I don't want to work and make 100 grand. I'm going to make 50. And Michael, you might say, hey, I'm really happy to work, not doing what I'm doing, but I'll do some part time stuff, I'll do some consulting, consulting stuff, and I'll make 50. So now you have 100 grand a year coming in. It could do that for a couple years. And Then it just sort of starts to build a game plan that's workable. But what I'm hearing is when you said you started the conversation with, we're not on the same page. This is not about money. This is about philosophically, how do we view the next five years? And I think this is a five year thing, because honestly, if you were to work full time for even three years, I think that this is a lot easier. And if you presume, and if we do presume that you do sell the rental property after you stop working, because then your tax liability will be different, then we're in really good shape. But I agree with Mark. It's a little close for me. Cause you guys are young and you're gonna live a long time, hopefully. So how we get you on the same page is just really talking through, like, what is it that I see myself doing? I think that, Michael, when you say, I want to have the ability to stop working, I think you will have the ability to stop working. But I think the answer is really like, well, what are we doing together here to get to this place? Because I don't think it feels good to kind of go at it alone. You have to both feel like you're on the same page. You feel good, hey, we're going to keep working for till the little ones graduated. Then at that, you know, leading up to that, in the next, you know, 18 months or so, we're both going to look at revenue. Really, what are the options for reducing our workload, having some money coming in for each of us and just so that we're kind of in the same boat, and then do that for a couple of years and then, boom, you're done. And that's kind of what I would say. Michael, are you mad at me for saying this? Tell me the truth.

[C]

No, not at all.

[A]

No.

[C]

I think I, you know, I think you're spot on. I think it's an agreement that Sonia and I have to come to. And I really think we are, if not already very close to financially independent. And so, you know, this is. Again, this. This is mostly what I'm trying to. Trying to get out of. This is, you know, some advice from you of how we get.

[A]

Yeah, I mean, do you feel okay selling the rental property? Or is that like, oh, I love that thing? Well, how do you feel about that?

[B]

I personally am emotionally attached, I suppose, to the rental. And I was hoping that maybe down the road our kids could have it.

[A]

Oh, come on. Damn kids. Good Lord, Mark. What am I to do? With this. What am I to do with this?

[D]

You're not a parent, Jill.

[A]

I know, but come on, how much more they're gonna. Kids are not gonna come out of school with anyway. It's better for the kids and your lives for you to have liquidity than to have a piece of property to pass down. What about the $900,000 house? That's not enough for them.

[B]

Yeah, I guess. I guess it is. But I wanted to say that I agree with you. Like, that's how I felt initially. Like, I think it will be best for both of us to keep working somehow. Like, even if it's, like, very part time.

[A]

Yeah.

[B]

I'll feel way more comfortable with that. That will cover at least health insurance and a little bit more. To me, that sounds like a more.

[A]

Yeah. Because even if you just both were working enough to cover, like, extra health insurance and have a few bucks left over. Yeah, that's great. You're still in a low tax bracket. You can still either sell the rental or, you know, kind of rejigger or even think about pulling money out of your retirement account. Being in a low tax bracket, to me, having liquidity, access to your money, whether it's the rental property, selling RSUs, having that money diversified, working and available is key to you guys feeling more secure in the future. Yeah, sounds good.

[B]

Sounds good.

[C]

Couldn't agree more. Thank you.

[B]

Yes.

[A]

All right, take a deep breath. I feel like you don't. You can cancel the marriage counseling session. I feel like we've gotten to that place. Do you guys have your estate documents? Done everything good tidy up?

[C]

I think we need them reviewed. But we do have estate documents, which we.

[A]

Perfect. All right, get back in touch with us. I really want to know how this story ends. I am very comfortable saying that. I think that the man, he's a little mad at me. I think that they can do it, Mark. It's just a question of kind of getting together and making sure that they both feel comfortable. If I were married to you, Mark, I would make you carry the health insurance and keep working. I don't know how you feel about that.

[D]

I can just envision Sonia, like, giving him the elbow throughout this whole time. See, I told you so.

[C]

See?

[A]

Told you, told you, told you. I mean, we love you both. And thank you so much for joining us. Listen, when you are looking at decades of financing your retirement, this is really the issue. It's just there are so many variables. So we want it to be a slam dunk. And when it's close, I'm going to err on the side of being more conservative because I'm a wimp. That is why. And I think that maybe things will be a lot better. Maybe. For all I know, the guy works at an amazing company and in a year he's going to be like, hey, my RSUs are worth $800,000. Who knows? I'm just saying things can change. So I would rather be a little more conservative. But if you and your spouse are going through something like this, you want to try to get on the same page, get in touch with us. Go to jillonmoney.com, click the contact Us button, write us a note, and if you'd like to come on the air live, check the box. Mark will do everything else. Hey, don't forget to sign up for the free weekly newsletter comes out every single Friday. You can subscribe to us on the Odyssey app or wherever you find your favorite podcasts. Please leave us a rating and review wherever you listen. And of course, do something nice for someone else today. Change your work, change your wealth, change your life. Thank you for listening and we'll talk to you tomorrow. Hey gang. I just made a first time ever purchase on behalf of the pod. I was so psyched because Mark and I don't do a lot of promotional materials, but I was able to create a branded sweatshirt. Yep, a Jill on Money branded sweatshirt with vistaprint. Now I'm not usually good at these things, but Vistaprint made it simple to bring this idea like, oh, wouldn't it be cool if Mark and I could create some sweatshirts that we'll try out and maybe the listeners would want to get them as well. They've got these great design tools. They have fast shipping human support if you need a little guidance along the way. Because the sweatshirts were so easy to execute. Now I'm thinking about doing some other stuff. Maybe there's some baseball caps or, I don't know, other fun stuff that you you guys would want. You'll let us know. There's a reason that over a million people trust Vistaprint for their small business. Print needs Vistaprint print your possible right now, new customers get 20% off with code [e-mail] it is not hard to destroy a college. Last season the podcast Campus Files brought you stories of fraternity drug rings, stolen body parts, campus colts, and more. And now Campus Files is back for another season. There's a guy screaming into his phone. He's like, I just saw Charlie Kirk get assassinated right in front of me. Every week is a new episode and a new story. It was so chaotic, it's almost like a university under siege. Listen to and follow Campus files available now wherever you get your podcasts.