Is Early Retirement a Possibility?

Summary

Podcast Summary
Jill on Money with Jill Schlesinger
Episode: "Is Early Retirement a Possibility?"
Date: March 12, 2026

Overview of Episode’s Main Theme

In this episode, host Jill Schlesinger takes a listener call from Dave in Connecticut, who, along with his partner, is contemplating a major life and career downshift—potentially retiring early or transitioning to part-time work. The discussion centers on the feasibility of “FIRE” (Financial Independence, Retire Early) for this couple, breaking down their finances, options for slowing down, and the psychological side of big financial transitions. Jill and her producer Mark analyze different approaches and provide both encouragement and caution as Dave weighs his next steps.

Key Discussion Points and Insights

Introduction & Listener Background [03:25–04:15]

• Jill greets Dave and sets a relaxed tone with weather talk.
• Dave (40) and his partner (36) are considering downshifting from high-earning careers to a more flexible, possibly less lucrative lifestyle.
• Dave’s income: $275–$400k/year (variable; could take a lower-paying, more local job at ~$80k if needed). Partner currently earns $50k, planning to drop to ~$30k part-time.

Current Financial Situation [04:51–07:28]

• Annual spending: $90k (can flex down if necessary).
• Savings strategies: Maxed 401(k), mega backdoor Roth, HSA, regular Roth IRAs.
• Current assets:
  • Dave’s 401(k) (traditional): $550k
  • Roth: $207k
  • Partner’s 403(b): $28k
  • HSA: $68k
  • Combined Roth IRAs: $170k
  • Brokerage/cash (post-home sale): $1.345 million
• Renting after selling a house; plan to continue renting. Annual rent: $40k.

Retirement/Downshift Feasibility [07:47–10:50]

• Dave wonders how safe it would be to make a drastic income cut—possibly all the way to $0 besides partner’s part-time work—and still be financially secure.
• Jill identifies two primary transition models:
  1. Stay in high-stress/high-earning role for a set period for a net worth “runway.”
  2. Downshift now, potentially pursue passion projects, and reassess spending/savings strategy.
• Health insurance planning—a must-add $10k/year to spending if both leave employer coverage.

How Much Longer to Work? [10:50–15:39]

• Timeline discussion: Dave could tolerate his current role if finish line is 3–5 years away, less so if it’s a decade.
• No major debt.
• Jill and Mark run the numbers: If Dave works five more years at the current savings rate (~$100k/year), they could accumulate ~$3.5 million, close to “a layup” for financial independence (Mark, [13:28]).
• Even quitting now and working part-time would likely work thanks to the robust brokerage account.

Psychological & Lifestyle Factors [15:39–17:44]

• Jill cautions: “50 years of retirement’s a lot” ([15:39])—longevity risk means more uncertainty for younger early retirees.
• Key concern is quality of life: Dave’s job is enjoyable but the long commute eats into weekly enjoyment and social life. Considering a lesser-paying, more local job could boost life satisfaction.
• Jill adds, “If you're feeling that way, then I understand it quite a bit more... that's life, and I couldn't live like that” ([16:39]).
• Dave and partner well-integrated finances and estate plans, discussing potentially formalizing their commitment (marriage).

Actionable Advice & Next Steps [17:44–19:20]

• Jill and Mark’s consensus:
  • Dave has options. Explore local, lower-stress opportunities first.
  • If willing to stay put for several more years, likely to have a “slam dunk” financial foundation.
  • If transitioning sooner, maintain a conservative asset allocation, especially in the brokerage account (buffer for early years’ withdrawals).
• Emotional flexibility and willingness to revisit the plan periodically are as vital as the math.
• Notable Jill quote: “You have done that. So, I mean, kudos to you.” ([18:58])
• Dave’s final question: Should they move more of their brokerage money into stocks or keep a conservative buffer?
  • Jill: If they stay at current jobs 5 more years, can take more risk; if transition soon, keep the buffer.

Notable Quotes & Memorable Moments

• “You've bought yourself some opportunity.” – Jill ([13:43])
• “In my mind, it's pretty close to being a layup.” – Mark ([15:28])
• “50 years of retirement’s a lot.” – Jill ([15:39])
• “That unpredictability over that long, long time horizon.” – Dave ([15:45])
• “The work week is for work, and the weekends are for relaxation, and so that sacrifice is tough.” – Dave ([16:14])
• "You have done that. So, I mean, kudos to you." – Jill ([18:58])

Timestamps of Key Segments

• Listener call begins: [03:25]
• Financial rundown and savings details: [04:51–07:28]
• Main retirement/transition scenarios discussed: [10:05–15:39]
• Psychological/lifestyle considerations: [15:39–17:44]
• Dave’s asset allocation/brokerage question: [19:04–19:20]

Conclusion

Jill and Mark commend Dave and his partner for their diligent planning and emphasize that, while there’s no “slam dunk” due to their youth and potential for a long retirement, their conservative lifestyle and ample savings make both continued high-earning and an immediate downshift very viable. The episode concludes with encouragement for Dave to continue exploring new job opportunities and to regularly re-evaluate as life changes unfold.

For listeners, the takeaway is clear: building options—and knowing your numbers—can make even big lifestyle leaps far less risky.

For more info or to ask your own question, visit jillonmoney.com.

Transcript

[A]

Everyone has their own reason for giving. Maybe it's to honor someone they love, to support a cause close to their heart, or just to make the world a little brighter. Whatever your reason, there's one way to do it better. A Donor advised fund from Daft Giving360 makes charitable giving simple, strategic and tax smart. Donate anything from stocks, securities and cash to non cash assets like real estate, life insurance and crypto. Contributions can be invested with the potential for tax free growth and then granted to any qualified U.S. charity. And you may qualify for a current year tax deduction on your contribution, but you don't have to make your grant decisions right away. No end of year scramble, no paperwork headaches, just smart flexible giving. All managed through an easy online dashboard. And there's no minimum to open an account. DaftGiving360 really does help you make a greater impact on your terms. Want to learn more? Visit dafgiving360.org hey gang, you know I'm all about not missing opportunities. And that starts with not missing calls. Because a missed call is money out the door. That's why today's episode is brought to you by Quo, spelled Q U O. The smarter way to run your business communications. Quo makes it easy for your team to stay on top of every customer conversation. Everyone can call, text and reply from one shared number. No more missed messages, no more disconnected threads. Plus it works wherever you are right from your phone or computer and you can even keep your existing number, add teammates new numbers or sync your CRM in minutes. It's built to scale as your business grows. And here's the kicker. Quo isn't just a phone system, it's a smart system. AI automatically logs calls, summarizes conversations, highlights next steps and can even handle after hours messages or qualified leads. Everything lives in one clean view so your team communicates faster, stays aligned and gives customers that personal touch that actually sticks. Make this where no opportunity and no customer slips away. Try quo for free. Plus get 20% off your first six months when you go to quo.com jillonmoney that's q-uo.com jillonmoney no missed calls. No no missed customers. Welcome to the Jill on Money show. It's Thursday, March 12th and we are here trying to help you parse through all of the anxiety you're feeling, the headlines and get down to what you can control your own financial destiny. So if you have a question, if something is going on, all you need to do is get in touch with us by going to jillonmoney.com. just click the contact us button. It's in the upper right hand corner. Write us a note if you'd like to join us live. You check the box and while you're on the website, you can check out our free stuff. We've got another podcast, it's called Money Watch. We've got a radio show, we've got a blog, videos, resources, so much right there. Don't forget to sign up for the free weekly newsletter while you are on the website. Right now it is time to talk to our listener, Dave, who joins us from Connecticut. Hello, Dave. Dave. I understand that it's gonna be 70 degrees here in the northeast. Are you ready for that?

[B]

So ready after all these snowstorms.

[A]

Oh, God, you must have gotten a big dump after that last one, the blizzard. What'd you get?

[B]

Oh, man. At least I wanna say 20 inches. 24.

[A]

That's a real number? For real.

[C]

Wow.

[A]

All right. Well, what brings you to us? Snow removal or something else.

[B]

So figured me and my partner, we love the show, we listen in and I think right now with where we are in life, we're thinking of downshifting. Ideally, we've been saving up for fire, but respect both you and Mark's opinion on this and just wanted to get a sense a gut check as to whether or not it's feasible.

[A]

Well, tell us about you and your partner and your family and what's going on. So how old are you?

[B]

I am 40 years old and my partner is 36.

[A]

Okay, are you both working full time?

[B]

Yes, although they are planning to downshift into part time soon.

[A]

Dude, I love that little pronoun shift. You're like, I gotta protect the anonymity of the partner. Okay, so tell us about how much you guys earn.

[B]

So my compensation is pretty variable. Depending on the year, I've made 275k a year, upwards of over 400. So it's pretty variable. They make approximately 50k right now and would be downshifting to part time work, which would probably pull in around 30.

[A]

Okay. And if you were to really hone in on that 275 to 400 range, if you were to downshift, what do you think you could downshift to? Reliably?

[B]

I would say at the very least, if I prioritize something that was more local, I would say something at least 80,000 a year.

[A]

Okay. And do you guys have kids or not?

[B]

No kids, just two cats. Oh.

[A]

All right. Do you think you guys could live on this hundred and let's call it 100 grand a year. Could you live on that or not?

[B]

Yeah, and I think we could actually. We've got 20k that we could flex down on, all said and done. So we live pretty below our means.

[A]

Okay, well what do you think you spend right now on this big chunk? You know, obviously, let's just say that you make between the two of you 350ish, because that's probably right. Okay, what do you think you spend

[B]

about 90k a year.

[A]

Wow. Okay, so tell us about your savings and see if this we can figure out whether the downshift is the downshift possible.

[B]

So right now I max my 401k, I do mega backdoor, I do Roth conversion as well as an hsa.

[A]

Oh my God, you are saving a ton. So how much is in, are you doing? I'm sorry, Roth or traditional?

[B]

So I do pre tax just because I'm in a higher tax bracket. And then my employer matches 50% of

[A]

that, how much is in traditional assets right now?

[B]

So in my 401k traditional, 550k. Okay, what else in Roth I've got 207k.

[A]

Okay.

[B]

And then my partner, they have a 403b that has a pre tax sum of 28k. And then in the HSA we've got 68k. And then we do have like separate non employer Roth IRAs that total 170k together. Yes.

[A]

Okay, got you. When you look at the like your cash flow now obviously you know you're saving all this money. Do you also have extra money to then put into a brokerage account? Because I mean, I know you're saving a lot in retirement. Is there any non retirement savings that you've done?

[B]

Yeah. So we have a total amount of, between the two of us, 1.345 million.

[A]

Mark. Can I have that little giggle? You know it's the mark giggle. It's The Telercio teehee. 1.345 million. Wow. Holy smokes. Do you guys own a home together?

[B]

No, we recently sold. So all of that was put into the brokerage account.

[A]

And why'd you sell? Just out of curiosity?

[B]

I think we just wanted to be closer to family, friends, so we moved to this new location. It's lower maintenance, less stress. Renting can be fun like that.

[A]

It's so great. Do you need to access some portion of that brokerage to buy again or do you think renting is for you?

[B]

I think renting is for us.

[A]

Excellent. What's the rent by the way, in wherever you live? Connecticut.

[B]

Quite a bit. 40 a year.

[A]

40 grand? Well, that's not that much. I mean, 40.

[C]

New York City, Joe. Right, sure.

[A]

Yeah, yeah, no, no, I totally get that. I'm just saying that, like, I know where he lives. He doesn't live right next to New York City, but it's like, it's close. Ish. So 3300 bucks a month is not so terrible to me. And do you like it? Do you like where you live or would you like to spend more? Like, what do you think?

[B]

I think it's perfect.

[A]

All right, great. This is an amazing story. What is the timeline for you?

[B]

I think just because of the job market and the precarity of employment these days, I really want to get a sense of if my partner is working part time, what would I have to, like, let's say I wanted to really flex into something that just doesn't pay as much. Right. But I'm really passionate about. I guess I want to assume that I would be earning nothing.

[A]

Zero. You just told me 80. How did I go from 80 to zero? Come on. So.

[B]

So I think if, if I lost my job, I would be able to find another full time job making at least 80. Right. But I think that, like, let's say I wanted to break out on my own and do freelance, or I wanted to pursue a pet project like animal rehabilitation. At that point, those pursuits don't really compensate much. And so I guess if I wanted to indulge in something like that, I would want to know that we're financially okay. But if I had to tough it out for a number of years doing what I've specialized in, you know, I want to get a sense of, like, when would we be okay in that regard? Right. Like, at what amount am I good to go?

[A]

So it's almost like there are a couple of different ideas here. One would be like, continue with this variable, but very high income. That is demanding. Do it for x many more years and then be able to go to zero. Right?

[B]

Yeah.

[A]

Presuming that your partner is going to 25 grand. Right. And just so I understand, when you say the expense is at 90 grand a year, would that include getting your own health insurance? Or would we have to. Would it be more than that? You know, should we add more into this equation just to make sure that we've covered your health insurance?

[B]

We would have to add more. I think when I looked at the marketplace, like, it would still be subsidized technically, but I budgeted 10 grand on top of the 90 to.

[A]

Okay, all right. All right, well, so that seems good. And you know, even if we just, I mean, instead of eight, let's just say, let's say nine grand a month. That would seem to be a decent way to figure it out. Okay, so is your partner entitled to any pension? Only because you mentioned a 403. So is there a pension possibility or. No?

[B]

No pension, unfortunately.

[A]

Okay, if I gave you the choice of, okay, you could work longer for some group of years or you could work part time immediately, but you have to work. You can't do like, you gotta make 50 or 80 grand a year. Let's say 80. Which one seems more appealing to you to have the. The like, wow, I don't have to do anything or I don't have to do this right now and I could do 80 for a while. What do you think sounds more appealing?

[B]

I think it depends on the timeline. Like if you told me I had to keep working my current job.

[A]

Yeah.

[B]

For 10 years.

[A]

Yeah.

[B]

I think I would struggle with that. If you told me three to five, I could definitely do that. I enjoy the work. I enjoy helping people. So I think it just depends on the time horizon.

[A]

And I presume you have no debt, right? Correct. Besides those two cats, which will, you know, they'll be into you for a while. Okay. So Mark, what do you think about Dave and his partner's quest for another endeavor? Not even retire early. It is there. You guys are really talking about. We, we've worked hard. We're good, you know, 15, 20 years out. And now we really want to just do something different and more enjoyable. And they've saved like crazy. I mean, crazy. Except that you're so young. So what do you think, Mark? Do you think that. How many more years of full time work? What if we did. Oh, my God, poor guy. What if we made him work five more years and you're saving so much like you are Saving basically like 100 grand a year at least, right?

[B]

Yes. Yep.

[A]

So 100 grand a year. You're one of those weird cases where you know you're going to go down in a, in tax bracket. So I'm not so freaked out about your whole, you know, your, your pathway forward in terms of Roth versus traditional. Mark, how many more years of saving? 100 grand a year, considering how much they've already saved, which is a lot.

[C]

Yeah, I mean, I have like two schools of thought. One is he basically just told us he's fine working another five years. He enjoys the job. He doesn't hate it. He's not miserable. So if he did that for another five years, saving $100,000 a year, I'm sure he knows this, they're going to have at least three and a half million dollars. On the other hand, if he wanted to quit today and you know, take six months to recharge, but then find something else part time for 80 grand, 100 grand a year, he could do that too because they have that brokerage account, right?

[A]

This is the thing that you've done. You've bought yourself some opportunity. So I think what's interesting here is I'm not gonna tell you it's a slam dunk just cause you're so frickin young, right? So if you did this for five years and you had 3.5 million bucks in the bank, it's all well and good and maybe you'll probably make something between the two of you, you make a little bit of money, but I don't think there's gonna be like a huge problem. You can live on your brokerage account. You can, you know, start pulling money out of your traditional account when. Yeah, I mean, I think it, it actually probably does work because we probably could pull 3 and a half, 4% a year out of your brokerage account. You would deplete it over time, right? But you would deplete it from, let's say age 45 to age 55, 59. It would go away mostly, not all. Then you would start pulling out of your traditional accounts, live on that. Then you'd have Social Security. So you can see how it works. It really to me feels more like you. What you need to do is go out there and find what would be available to you as a part time or next or new endeavor. Because if you find that like not the pet project so much, but like, what if you could get a job that you liked and you're into and it's not as much travel and you are down scaling a little bit, but that you can find a thing that would make you happy at 80, 90, 100 grand, your partner's making 25. And now you guys are supporting yourselves, living a nicer life, maybe a little bit less stress, and having a lot of, a lot more Runway in the future because you're not tapping out of your assets. So I don't know, it really depends on your personalities. A lot of people get freaked out about spending down or keep doing what

[C]

you're doing for five years. And in my mind it's pretty close to being a layup.

[B]

Okay.

[A]

I would say it's in the paint. I don't know if it's a layup, but, yes, it's only just because given

[C]

how much they save.

[A]

Yeah, but they're so young. So, you know, if they're 45 and they live to 95, 50 years of retirement's a lot.

[B]

It's that unpredictability over that long, long time horizon.

[A]

Right? Yes, exactly. Right. I don't know. I, like. I think that it depends also about, like, how you guys come to this, how you are approaching this together, how much. You know, I don't know if what you do right now is so taxing, by the way, at age 40, this is when you're supposed to be taxed, but you know that if you just are like, I'm dying inside. But it doesn't sound like that, which is sort of weird to me that we're having this conversation.

[B]

I think the issue is that living where I live, the commute is quite a bear. So to do that every week, it means that anything that I could do during the week in terms of social life and everything is. Isn't there. So really the. The work week is for work, and the weekends are for relaxation, and so that. That sacrifice is tough.

[C]

Oh, social stuff is overrated.

[A]

Yeah, it is. Why don't you, you know what, get another cat. You'll be fine. You won't miss anything. This is really one of those things that I don't have the. I hear what you are saying, and I think people who travel a lot or have long, long commutes. I was just in the car going to this, like, you know, wedding in New Jersey that was, like, in the middle of fricking nowhere in New Jersey. And my wife said to me, oh, you know, so and so commutes from here every day. I am not kidding. It must be four hours in the car every day. I would kill myself. So if that were the kind of thing that you were, like, encountering, I don't think I could do that. And we know people have really long commutes all over the country. To me, like, that's life, and I couldn't live like that. So if you're feeling that way, then I understand it quite a bit more. But I think that you're. Is there any chance, by the way, that you guys are going to get married, you're going to make honest people out of each other, or do you not care?

[B]

I think we. We are, like, we're very committed to each other. We look at our finances together. We have an estate plan.

[A]

Okay.

[B]

So I Think our lives are very much integrated. And so it is kind of like that final, that final step.

[A]

All right, I, I think, I think you're going to be okay either way. But I do think it's important for you to get a sense of really what else is out there so that you have a truer way to compare what you're doing now for three or five years. And look, if things go crazy and the economy's fantastic and three years from now we're talking to you and like, the numbers are really working and you can kind of start winding down or pulling some money out or getting some, some Runway for a couple of years of living expenses in advance. And things are just way better than you had anticipated. You made 400 a year, so you didn't save 100, you saved 150. Whatever it is, we can revisit this in three years. Or if it's like, oh, man, I just like sent out a Note to my LinkedIn network and someone came back to me and I can make 120 grand a year in something that sounds really great and close and I'd like to try that. That's also a good option. I mean, it's so wonderful that you and your partner have created these options for yourselves. And that to me is incredible. You have done that. So, I mean, kudos to you. We'll look forward to hearing more from you. I really think there are some really terrific opportunities for you ahead. So keep us posted. Are there any other questions we didn't answer yet?

[B]

I have just one. Given the spending down of the brokerage account, we have a lot in Treasuries, I would say. Okay, should we put more of that into stock or do we really need and want that buffer in the event that something happens?

[A]

I think it depends on what we're gonna, what like the pathway is. So if you're five more years, absolutely, you can put more in stocks. If it's like two years, then I want that buffer. Okay, so if you are like Dave and his spouse, his partner, and you are looking to find a new or next endeavor, get in touch with us. Go to jillonmoney.com, click the contact us button, write us a note and of course, let us know if you'd like to join us on the air live so we can ask you all of these more interesting in depth questions, not just the actual balance sheet questions. All right, you can subscribe to us on the Odyssey app, where, by the way, you can also subscribe to our weekend broadcast called Money Watch. So on the Odyssey app or wherever you find your favorite podcast, we ask that you do something nice for someone else today. Change your work. Change your wealth. Change your life. Thank you for listening. We'll talk to you tomorrow. Hey, gang. You know, subscriptions are one of those things that feels small in the moment, and then suddenly you're wondering why you are paying for all these things that you barely use. That's where Experian subscription cancellation comes in. Experian can take the pain out of canceling subscriptions by handling it for you. Just keep the ones you want, cancel the ones you don't, and put the money back in your pocket instead of spending your time trying to cancel subscriptions. If you even do that. And you know there are over 200 subscriptions that are cancelable, which means that there are lots of opportunities to clean things up. And. And it doesn't stop there. You can also save money by letting Experian negotiate the rates on bills you're already paying. They'll keep an eye out for new deals and savings opportunities and negotiate directly with your provider on your behalf. Get started with the Experian app now. Results will vary. Not all bills or subscriptions eligible. Savings not guaranteed. Paid membership with connected payment account required. See experian.com for details. 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 cults, and more.

[C]

And now Campus Files is back for another season.

[B]

There's a guy screaming into his phone. He's like, I just saw Charlie Kirk get assassinated right in front of me.

[A]

Every week is a new episode and a new story.

[B]

It was so chaotic. It's almost like a university under siege.

[A]

Listen to and follow Campus Files, available now. Wherever you get your podcasts.