I’m Fried, Can I Retire Next Year at 55?

Summary

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Podcast Summary: "I’m Fried, Can I Retire Next Year at 55?"

Jill on Money with Jill Schlesinger
Date: June 29, 2026
Episode Theme:
Jill Schlesinger takes a call from Roger, an Illinois listener burned out after 24 years at his job who wants to know if he can retire at 55, make his creative side hustle his main focus, and still maintain his financial security. Jill and her producer Mark dissect Roger’s financials, probe the risks, and deliver a candid, no-nonsense assessment of his prospects for an early retirement.

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Episode Overview

• Main Theme:
  Can Roger, 54, retire from his well-paying job next year at 55, live off his savings, and turn his long-standing wood and bone carving side hustle into his primary gig? Jill and Mark provide a thorough, plain-language financial checkup, weighing hard numbers against dreams and risk factors.
• Purpose:
  Offer actionable retirement advice for early retirees, especially those considering pivoting to a passion project or side hustle as a new main income stream.

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Key Discussion Points and Insights

1. Roger’s Situation and Motivation (05:32–06:36)

• Roger’s current job: 24 years in the same position, feeling “burned out.”
• Reason for switch: Wants to pursue carving (wood, bone, etc.), his side hustle for 30 years, as a main gig.
  • “I'd like to retire and pursue that.” – Roger (05:40)
• Current side hustle income: About $6,000 a year; thinks he can increase this with more time.
• Marital status: Married, wife currently not working due to health but may return in future.
• Kids: Two grown sons, living at home, paying rent, self-sufficient.

2. Roger’s Finances: Detailed Breakdown

a. Income and Expenses (06:48–08:27)

• Current salary: $130,000/year.
• Household spends about $6,000/month (excluding healthcare and taxes).

b. Assets and Savings (09:35–10:48)

• 401(k): $1.3 million (Traditional, pre-tax)
• Spouse’s 401(k): ~$20,000
• Brokerage account: ~$100,000
• Savings: $20,000 (high-yield), $30,000 (CD), with additional $30–$40k coming in from timber income in the fall (one-time lump sum from family farm logging)
• Farmland: Owns half of family farm (worth ~$1 million). Not expected to sell; considered legacy for kids. Ongoing income: $12,000/year from farmland rental.
• Home: Worth $230,000, mortgage-free.

c. Pensions and Social Security (08:34–13:21)

• Two "tiny" pensions:
  • $120/month (or $20k lump sum) available now
  • $200/month (or lump sum) available at age 65
• Social Security:
  • At 62: $2,500/month
  • At 67: $3,700/month
  • At 70: $4,700/month

d. Healthcare (13:47–14:34)

• Roger can stay on former employer’s health plan until 65 at ~$700/month for family coverage.

3. Big Question – Is Roger’s Plan Feasible? (15:08–19:07)

The Math:

• Needs $6,000/month for living (excluding healthcare), plus $700/month for health insurance: $6,700 total monthly need.
• Side hustle could realistically bring in $1,000/month if he focuses full-time.
• Farmland rental brings $1,000/month.
• That covers ~$2,000/month—still $4,700/month short.

Withdrawal Strategy:

• 401(k) withdrawals under Rule of 55 are possible since he’s separating from service at 55.
• "You could safely take like $4,000 a month from that account and probably not run out of money, but that's not $6,000 a month." – Jill (15:46)

Jill’s Bottom Line:

• "I would not feel comfortable doing it this way. I would be much more comfortable if you had more money in the retirement account or more money in the brokerage account… I think it's tight." (16:53)
• Main concerns: No extra cash buffer, reliance on everything going exactly to plan, uncertain return of spouse to work, farm is illiquid legacy asset.

Mark’s Assessment:

• "Everything's gonna have to go, like, really just right." – Mark (17:41)
• If side hustle exceeds $1,000/month, it helps the math, but he shouldn't count on best-case scenarios.

4. Risks and Scenarios (17:47–19:57)

• Best-case: If wife goes back to work or farm is sold (and proceeds invested), early retirement could work.
  • "If you are like Roger… and you just want to try to make your side hustle your main hustle, give us a holler." – Jill (20:15)
• Fallbacks: Roger could try side hustle full-time for a year, but must be ready to return to part-time work if necessary.
  • Jill cautions: "It's a risk. And if you feel comfortable assuming that risk, then you can go ahead and do it. But, you know, you are young, and I just want to make sure we're doing this with our eyes wide open." (19:59)
• Caution: "I don't want to be a dream crusher. I just want to be a realist." – Jill (20:38)

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Notable Quotes & Memorable Moments

• Jill on risk: "I don't like to do planning based on every single thing going right." (17:47)
• Mark on the side hustle income: "If he could get it beyond a thousand, then, you know, then that changes the equation." (17:47)
• Jill’s ‘dream crusher’ warning: "I just want to make sure everyone understands that, you know, things happen and you can get unlucky, too." (20:41)
• Roger’s candid realism: "I'd like to try it for a year or two with the carving and see what I can do. If that doesn't work out, then go back part time.” (18:54)
• Jill’s encouragement: "We're going to kind of do advice and counsel, and you're going to make your own decisions. That's what you do... If things all go great, you come back and you're like, I didn't take your conservative, boring advice. Fine." (20:16)

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Key Timestamps for Major Segments

• [05:32] Roger introduces his issue and side hustle ambitions
• [06:36]–[08:27] Deep dive into current earnings, family, and expenses
• [09:35]–[10:48] Detailed review of retirement accounts, brokerage, and savings
• [12:18] Farmland value discussed as legacy asset
• [13:01]–[13:21] Social Security estimated benefits at 62, 67, 70
• [13:47]–[14:34] Health insurance options and costs in early retirement
• [15:08]–[16:53] Jill and Mark analyze feasible withdrawal rates and risk
• [17:47]–[19:57] Discussion on side hustle, fallback plans, and realistic options
• [20:13] Jill’s parting advice on risk, realism, and next steps

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Tone & Takeaways

• Tone: Supportive but candid, pragmatic, and slightly cautionary, laced with Jill’s signature friendly directness.
• Message: Early retirement at 55, supported by a passion project as a side hustle, is potentially possible for Roger, but only if he’s willing to accept significant financial risk. Having a more robust cushion in liquid assets or a working spouse would make the plan safer.
• Action for Listeners:
  If you’re "fried" and want to pivot to your own side hustle, run the numbers, have a backup plan, and get real about the risks—then reach out to the Jill on Money show for advice.

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For financial questions or to appear on the show, visit jillonmoney.com and click the "Contact Us" button.

Transcript

[A]

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[B]

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[B]

welcome to the Jill on Money Show. It's Monday, June 29th. I can't believe it. We are getting through the first half of this year. It's been a blistering pace. I know. Maybe it's just like as you get older, time goes by really quickly. But that's what I find at least. And if you're finding that your first six months has gone by really quickly and you haven't gotten to the to do's on your financial list, give us a holler. We might be able to light a little fire under your tush and get you going. And remember, Mark and I are both certified financial planners, so we love doing this stuff. If you have a question, all you need to do is go to our website, jillonmoney.com jillonmoney.com click the contact us button, write us a note. And if you would like to join us live, you can check the box for either audio or video. Why video? Well, because tomorrow we are launching our brand new podcast web show called called Money Moves. And we are going to put you on video if you so desire. You know, Mark, I had this idea that I wanted people to be able to come on with their video but blur them out like they're in the witness protection program. I thought that would be kind of a fun thing. Or we could put. What would you want to put up? Like maybe just a little piggy because we have a piggy bank and. How do you say piggy in Mandarin, Mark?

[C]

Piggy. Juro.

[D]

Juro.

[B]

Okay, so I think we maybe if you want to come on as video, but we're going to blur you out, we'll put a little pig up on your face.

[C]

I think that would help because as predicted, as you've said, most people do not want to come on camera.

[B]

I'm sorry, I keep telling people this, that it's not easy. And you know, I get it. I wouldn't do it either. So if you want to do it, great. If not, no big deal. We're going to figure this out. I'm going to tell you right now, we're going to figure this out. So. But do get in touch with us. Go to jillonmoney.com everything lives there. And also while you're there, you can subscribe to our free weekly newsletter which comes out on Fridays. This also entitles you to our blog. And, you know, hopefully you get the whole rundown of everything going on by being a subscriber. It's very easy to do. Hey, did you miss our session with Social Security queen slash expert Heather Schreiber? We conducted our webinar. It was a couple weeks ago and Heather was on fire. Mark and I did decided that, Mark, we have to do that episode where we're just going to do all of the people who asked amazing questions who we couldn't get to, but Heather just answered questions in, in like this rapid fire manner. Mark and I were talking after it was over. It was like you, you cannot believe how much information this woman has in her brain. She's incredible. And so I want to make sure that we highlight her. And if you want to buy the episode, it's 15 bucks. Not a big deal. But we're going to do an episode with Heather where we're answering more questions. Boy, she was fantastic. And again, you can buy the single webinar for 15 bucks. Now that has taken place and just. It's under the Jill on Money live area. Okay, let's now get to you. It is Roger who joins us from Illinois. Hello, Roger. What can we do for you?

[E]

Hi, Joe. Hey, Mark. I was hoping I could retire at 55 and pursue other interest.

[B]

I am burnt out. Are you feeling like you want to do something like really radically different? Like what's going on for you?

[E]

So, yeah, I mean, burned out. I've been at the same job I'm at now for pushing 24 years. I've had kind of a side hustle for quite some time. So I, I'd like to retire and pursue that.

[B]

So you mean you, your real question is, can I make my side hustle? My main hustle?

[E]

Right, that's, that's would be the goal, yeah.

[B]

Oh, I like that idea. Why did you start doing this side hustle? Was it for money or was there some other reason?

[E]

It's been 30 some years ago I started that. But yeah, it was, it was money, but it was also just a desire. You know, I, I carved different things, wood, bone, make things out of that. And. But it was. Yeah, at the time I needed extra money and now need extra money, but I still do it because I enjoy it.

[B]

That's so great. That's awesome. So, okay, let's talk a little bit about like what's going on in your life. For example, you're working full time now and how much are you earning?

[E]

I make about 130,000 a year.

[B]

And how much does the side hustle bring in?

[E]

It varies a lot. The more time I put into it, the more money I make. But I don't know, on the average, probably right now around, I don't know, I'm probably making around 6,000 a year. Okay. I could definitely make that more. I'm positive I can.

[B]

Okay, that's okay. But the, but we got the 130 and are you married, single, partnered?

[E]

Yeah, I'm married.

[B]

And does your spouse work currently?

[E]

No, she's got some health issues, but she's recovering from that. But she does plan on going back to work at some point.

[B]

Okay, but are we doing this. Are we trying to create this exercise without thinking whether. Like, that you would have to do it, in other words. Right. You would want to make. Okay, got it.

[E]

Yeah.

[B]

So, okay, next up. Do you have grown kids? Do you have. Is everyone on there? Okay, so that's good to know. And they're on their way. Do you help them out?

[E]

So I have two grown sons. They. They both still live at home, going to college and working. However, they pay me rent, so they're providing for themselves. They're not costing me money.

[B]

That sounds good. So when you look at your bills right now, forgetting about the rent that the kids give you, but like, let's just talk about your various bills that you have out there. Tell us, like, how much do you spend?

[E]

About 6,000amonth. I'm still figuring on that, but that's what I'm seeing right now. About 6,000amonth.

[B]

Okay, that's great. And will you be entitled to a pension of any kind?

[E]

Okay, so I've got two tiny little pensions.

[B]

Hold it. Teeny tiny pensions. Got it.

[E]

Yeah. So one at the time of retirement, you know, whether it's now or later, that one provides about $120 per month. Or I could take it as a lump sum. That would be roughly about 20,000.

[B]

Okay, 20 grand. Okay. And what's the other one?

[E]

The other one is, it's roughly 200 per month. But I don't understand this, really. But I can't get it until I'm 65.

[B]

200amonth. And at 65, is there a lump sum amount?

[E]

I think that is an option, too.

[C]

Okay.

[B]

All right.

[E]

What the lump sum is.

[B]

Okay, fair enough. So when you look at the kind of. The big basket of savings, tell us about what you have done so far apart from these pensions. So let's talk with. Let's talk about, like, the retirement plan savings so far.

[E]

Yes, I have a 401k, traditional tax, deferred. Yep. I have 1.3 million in that today.

[A]

Great.

[B]

Okay, fantastic. Does your wife have an old retirement plan as well?

[E]

She has a very small 401k, maybe about 20 grand.

[D]

Okay.

[B]

I love when people say not much. Like 20 grand is a number, man. You know what I mean?

[E]

Come on.

[B]

Is that all for retirement? Do you have IRAs?

[E]

No.

[B]

Okay. And what about none non retirement. Like a brokerage account or savings or CDs. What do you got in that?

[E]

I've got a brokerage account. There's about 100,000 in that.

[B]

Great.

[E]

For savings. Currently I have about 20,000 in a high yield savings and another 30,000 in a CD.

[B]

Any other asset besides real estate? Just in terms of like financial asset.

[C]

Yeah.

[E]

I've got. Well I guess to add to that savings and cd I got some more money coming at the end of the fall.

[B]

Tell me more.

[E]

Probably 30, 40,000 somewhere in between there. And I plan on just putting that into another cd.

[B]

What is that from?

[E]

So okay. I, Okay. I own some farmland.

[A]

Oh.

[E]

Me and my cousin inherited it. So I own half of, of our family farm.

[B]

Okay.

[E]

And that money is from. We're logging out part of the timber on our farm. So that's, that's from that.

[B]

What do you think your half of the farm is worth?

[E]

About 1 million.

[B]

Wow. But is this something that will never be sold or is this something that you could sell in your lifetime?

[E]

It'd be highly unlikely. We have that rust and it, the plan is eventually it'll go to my children.

[B]

Okay, but is it fair that we could count on that 30 or 40 grand a year in terms of just extra income or not?

[E]

Nope. That 30, 40, 000 a year, that's a one time deal for the logging.

[B]

Okay, I got you.

[E]

I do receive rent for the farmland.

[B]

How much is that?

[E]

My portion of that's 12,000 a year.

[B]

Okay, so farm rent is 12 grand. Any other income that's such a, like. Okay, you know, I want that money from the farm, but it's just not happening.

[A]

I'm gonna, I'm.

[B]

Let it go. Let me let it go. Million dollar asset that's yielding 12 grand a year is nothing like I, I, I. All I want is that money. But there's no other money that is coming in terms of income and asset. Like the assets have already been passed to you.

[A]

Is that right?

[E]

Yes.

[B]

Okay. And you know what I forgot to ask very important. Roger. How old are you and how old is your wife?

[E]

I am, I will be 55 in September.

[B]

Okay.

[E]

My company has, you know, the rule of 55. So.

[B]

Yes, got it.

[E]

That door opens for me very soon.

[B]

Okay.

[E]

And your wife, she is 48.

[B]

Oh, she's young. Okay. And presumably she would be claiming half of your Social Security in the future, is that right? Or is she going to have her own record that she would claim on you don't. I guess we don't know Yet. Because she hasn't gone back to work.

[E]

Yeah, I. The plan is that she would have her own.

[B]

Okay. Do you know what your Social Security benefit looks like right now?

[E]

Yes. Tell me it's 2500 at 62.

[B]

No, no, do not give me 62. I'm going to ban 62 from our lives. Okay, let's do 67 and 70.

[E]

Okay, 67. 3700amonth. And 74. 700amonth.

[B]

Okay. How's your health now? You said your wife had some issues. Good.

[E]

No, I'm good. Yeah.

[B]

Okay. The house, the. The actual primary home, how much is that worth?

[E]

230, 000.

[B]

Is there a mortgage on it?

[E]

No, it's. No, we own it outright.

[B]

Okay. And there's no other real estate besides the farm.

[A]

Right, Right.

[B]

Okay, so here's the question that you're. Have I gotten all the stats and all the info so far?

[E]

Healthcare, maybe?

[B]

Oh, yeah, I'd like healthcare. What would you do at 55?

[E]

So my company lets me remain on their plan, but at a increased rate.

[B]

So forever. Like, until 6. Like, for the next 10 years, until

[E]

I'm 65, and also until my wife's 65.

[A]

Oh, that's good. All right.

[B]

But it's a little bit more expensive, but at least you have it, right? Okay. When you said six grand a month, does that include the health care or not?

[E]

That does not.

[B]

How much?

[E]

Health care or taxes?

[B]

Okay, so health care, what do we think it will cost you in retirement for those 10 years?

[E]

If I retired soon, I'm on a family plan. That's about 680amonth after retirement.

[B]

Okay, I'm gonna say 700amonth. Okay. Let's just presume. I mean, obviously the kids can only stay until they're 26, but let's just. I'm gonna use that 6. $700 a month as a holder. Right. So now we have $6700 a month is your need. You know, I know that you said that your side hustle's just a couple, you know, 6,000 a year. You said you could make that more. What reasonable dollar amount can we put on the side hustle? Like, what amount of money do you think would be reasonable to assume you could do if you were not working?

[E]

I Honestly, I feel 10, 12 grand wouldn't be a problem.

[B]

Okay, so like a thousand bucks. A thousand bucks a month?

[C]

Yeah.

[E]

I mean, I. I feel like.

[B]

So put it this way. If you made a thousand dollars a month, we could pay for your health care, then we're back to your 6,000amonth as your basics. Okay, so what you're asking me is, hey, Jill, can I take $1.3 million from my traditional account? Can I pull enough money out to create $6,000 a month of income? If I tell you no, what's going to happen? Are you going to freak? No, you're not. What do you think the answer is in your heart of hearts?

[E]

I think it's possible, but it might be tight. It's going to be very dependent on my other income streams.

[B]

Here's the thing. If we really look at just the thousand dollars a month that is coming in, and we're not assuming your wife is back to work because we don't know she's back to work yet. Right. She would like to go back to work. But so if we're just looking at your own income, I look at this and I say, okay, well, there's $1.3 million in this account. Right. And you say, well, I want to invoke the rule of 55. Fine. Okay. So let's presume that you take. I don't know, I'm going to just give basics four. You could safely take like four grand a month from that account and probably not run out of money, but that's not six grand a month. I think you're right. If you just decided you wanted to die with zero at the right time, you may be able to do this. I would not feel comfortable doing it this way. I would be much more comfortable if you had more money in the retirement account or more money in the brokerage account.

[A]

And.

[B]

And that you didn't have to start dipping into it for a few years. Now Mark is probably running all the numbers. And Mark, do you agree with me? I'm just doing it based on looking and doing math in my head. So am I right that it's probably a little tight, even with a couple hundred dollars from pensions? But the 10 years, we have to get at least 12, or let's say 12 or 15 years till Social Security. I'm feeling a little anxious about this, especially since I don't have the million dollars from the farm. What do you think, Mark?

[C]

Yeah, I tend to agree. I mean, he's got, you know, he. He will hopefully have a thousand from the side hustle. If he ramps that up, he's going to have a thousand from the farm rental income that comes in every year. So that's 2,000amonth, but 4,000. Yeah, I mean, everything's gonna have to go, like, really just right.

[A]

Yeah.

[C]

I would love the side hustle to go, you know, if he could get it beyond a thousand, then, you know, then that changes the equation.

[B]

Yeah, I think it's. I don't like to do planning based on every single thing going right. So I really think that it would be important for you to build up a little bit of cushion, and the cushion would be just working a little bit longer and then seeing, you know, it is possible. Just to be clear, it is completely possible that you could do this. Your wife is back to work in a couple of years. All of a sudden she's making, I don't know, 50, 60 grand a year. And now you're. You might be able to do it, but until we know that for sure, I would not feel comfortable doing it, Roger. I wouldn't. Or two things. Either she's back to work and working, you know, full time. Ish. Or bringing more money in, or you say, actually, we are going to sell the farm and I have a million dollars less taxes, and, you know, I have 700 grand that I can pay pop into my. My brokerage account. Now there's 800. Like, all of a sudden, now I feel like there's a. That's your cushion. But without either of those things, I think it's tough. I really do. So I hope that's not too disappointing for you.

[E]

No, I mean, my thoughts was I'd like to try it for a year or two with the carving and see what I can do. If. If that doesn't work out, then go back part time, you know, which is common in my.

[B]

Okay, here's, here's. Here's the issue with this. I'm gonna. I'm gonna poke holes. What I have to do. This might be a dream crusher kind of day. I'm okay with that. Do you have a job where you could go back part time?

[E]

Yeah, that's pretty common.

[B]

Yeah. Okay.

[E]

Yeah.

[B]

And do you feel like. Is now really the right time to do that? Like, you know, I don't know what you do for a living, but then you don't have to say. But I mean, it's a huge risk to me, and I want to make sure that we've given you plenty of cautions, but if you wanted to do that, sure, I guess you could go back and you could go back part time and you could say, well, you know, in the year that I, you know, did my side hustle full time, I could make a thousand dollars a month from that, and I could bring in five grand a month working part Time. My wife's making three grand.

[A]

Like, if it all starts to add

[B]

up that way, sure, it can work. It's a risk. And if you feel comfortable assuming that risk, then you can go ahead and do it. But, you know, you are young, and I just want to make sure we're doing this with our eyes wide open.

[E]

Yep. Thank you.

[B]

Does that seem reasonable?

[E]

Yes.

[B]

All right. You know, people come on the program, they're going to ask their questions. We're going to kind of do advice and counsel, and you're going to make your own decisions. That's what you do. So I think that that's fine. I just want to make sure we're appropriate in our, you know, in being sober about the things you guys all want to do. So there's a lot of different ways to get there. If things all go great, you come back and you're like, I didn't take your conservative, boring advice. Fine. But I also want to make sure everyone understands that, you know, things happen and you can get unlucky, too. So if you are like Roger and you are kind of fried and you just want to try to make your side hustle, your main hustle, give us a Holler. Go to jillonmoney.com, click the contact us button, write us a note. And if you'd like to come on the air, check the box. Mark will do everything else. While you're on the website, check out all of our content that lives there, including our brand new show which starts tomorrow, Money Moves. You can find it. I guess we're going to have links to it on the website, right, Mark? And then also we'll have a YouTube channel. Anyway, if you have a question, we're always here for you. And don't worry, we always, always, always love to hear from you. Whether it is trying to give you the advice that's going to help your dreams come true. Or maybe just make sure that your dreams are have a little bit of reality that you can ground them in. Just again, I don't want to be a dream crusher. I just want to be a realist. Okay, so subscribe to us on the Odyssey app or wherever you find your favorite podcast. Always lift someone up. Change your work, change your wealth, change your life. Thank you for listening and we'll talk to you tomorrow.

[C]

Nerds.

[D]

Today's episode is sponsored by NerdWallet's Smart Money podcast. Personal finance can feel like a pop quiz you didn't study for. This podcast is your study guide on NerdWallet's Smart Money podcast. You'll hear from from trusted journalists who explain the why behind major financial decisions. You'll get research backed, insights and clear pros and cons. Whether you're planning a big purchase or just want to grow your wealth, make your next financial move with confidence. Follow NerdWallet's Smart Money podcast on your favorite podcast.

[B]

Applied.