Can I Fully Retire in 2-3 Years?

Summary

Episode Summary: “Can I Fully Retire in 2-3 Years?”

Podcast: Jill on Money with Jill Schlesinger
Date: January 7, 2026

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Episode Overview

This episode centers around a listener call-in with Angela from Texas, who is contemplating retirement in the next two to three years. With her husband planning to retire soon and both approaching their late 50s, Angela seeks Jill’s expertise in determining if they are financially ready to step away from work, how to structure withdrawals, and how to address some specific tax and estate planning questions. The discussion provides actionable advice, practical frameworks, and covers the emotional aspects of transitioning out of the workforce.

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Key Discussion Points and Insights

1. Angela’s Retirement Readiness (02:39–07:01)

• Background:
  • Angela is 56, turning 57, and her husband is 54, turning 55.
  • She expresses a strong desire for a retirement plan, feeling apprehensive but prepared for a transition out of corporate life soon.
• Financial Snapshots:
  • Both have substantial pre-tax 401(k) balances: $1.3M (Angela) and $1.2M (husband); about 10% in Roth accounts.
  • Husband will receive a lump sum pension (~$500K) and plans to retire next summer.
  • Brokerage account: ~$50K; cash savings: ~$50K; company stock: ~$50K, low basis.
  • Home value: ~$450K, mortgage balance: ~$56K at 3.125% interest.
  • Commercial real estate expected to net $400–500K “after taxes,” likely to be liquidated in the next 1–2 years.
• Social Security Projections:
  • Full retirement age (67): $3,665/month (husband); $3,629/month (Angela).

Jill Schlesinger [03:12]: “Dude, you made it sound like you married a 35 year old. So I was excited for a second, but. Okay. They're like the same age. Yeah, exactly.”

2. Spending, Withdrawal Strategy, and Tax Considerations (07:01–09:32)

• Spending Needs:
  • Angela estimates monthly expenses at $12,000.
  • Both are open to (but not reliant on) part-time “side hustle” income post-retirement.
• Portfolio and Withdrawal Structure:
  • After pension and real estate sales, total investable assets will exceed $3.5M, mostly pre-tax.
  • Jill calculates that this would require steady withdrawals before Social Security kicks in at 67—a classic “bridge period” for early retirees.

Jill Schlesinger [08:57]: “Are they comfortable spending down what they have? Because that's what it's going to take, right? You're going to have to take some of that two and a half million bucks, which will now be three because of the lump sum… You got to spend it. How do you feel about it?”

• Tax Bracket Analysis:
  • Pre-retirement income: ~$300K/year; anticipate dropping from the 24% federal tax bracket to 22% post-retirement.
  • Early withdrawals from 401(k)s will be taxable; recommend using pre-tax dollars first for living expenses after 59½.

Jill Schlesinger [09:34]: “… you're probably going to be in that 22% tax bracket. So maybe you will go down a tax bracket. You're going to need to pull the money out of your pre tax account. You're going to pay the tax on it. And if you're freaking out, then what's going to happen is you're going to be like, oh my God, I have to go back to work…”

3. Emotional & Legacy Considerations (09:32–10:58)

• Family Factors:
  • Angela expresses concern as a parent about spending down assets.
  • Jill observes that letting go of the “savings mindset” is harder for parents than for retirees without kids.
• Flexibility:
  • Jill reminds Angela that early retirement can be adjusted if her daughter needs support or if plans change after she graduates.

Jill Schlesinger [09:49]: “This is, I think, a very difficult decision to make for parents more than anything else. It really is. So if you're willing to. I think it can work. I do. But maybe you'll change your mind depending on what's going on with your kid.”

4. Lump Sum Pension vs. Annuity (10:58–11:19)

• Angela’s husband is “dead set” on taking the lump sum pension. Jill supports this, noting there’s no sense arguing with a determined Texan.

Jill Schlesinger [11:11]: “I'm not getting in the middle of that. A dead set Texan, really? Like, come on, there's no way I'm getting in front of that train.”

5. Financial Advisor Input & Money Management (11:20–11:54)

• Angela and her husband are experimenting with financial planners while also self-managing investments. The adviser’s review suggests they’re “good” to retire by 60, but Angela wants to see if retiring earlier is realistic.

6. One-Stock Concentration & Charitable/Family Gifting (11:54–13:21)

• Angela possesses $50K in a single company stock, acquired 20+ years ago.
• Jill suggests:
  • Gifting some appreciated stock directly to charity for tax efficiency.
  • Gifting to her daughter post-graduation and allowing her daughter to sell at what would likely be a lower tax rate, if she’s in a low income bracket.

Jill Schlesinger [13:02]: “So that's a possibility as well. I'm sure that the financial planner will walk you through that. But, you know, it's a big bet to have one stock if someone like. But it's not gonna kill you either…”

7. Estate Planning (13:21–13:29)

• Angela confirms all estate planning is “done,” which Jill affirms is crucial.

8. Closing Banter & Recommendations (13:31–13:59)

• Jill and Angela share some light banter about popular TV shows set in Texas, showing Jill’s personable, conversational tone.

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Notable Quotes & Memorable Moments

• On retirement jitters and readiness:
  • “I just feel like I'm ready to walk away from the corporate world in a couple of years.”
    – Angela [03:33]
• On the emotional difficulty of spending in retirement:
  • “People have a hard time doing this. I gotta tell you, Angela, this is, I think, a very difficult decision to make for parents more than Anything else.”
    – Jill Schlesinger [09:49]
• On lump sum vs. annuity:
  • “A dead set Texan, really? Like, come on, there's no way I'm getting in front of that train.”
    – Jill Schlesinger [11:11]
• On simple withdrawal strategy:
  • “You did save it. Why can't you spend it?”
    – Jill Schlesinger [08:59]
• On charitable giving with appreciated stock:
  • “If you gift the stock to the organization, that's number one...you can probably avoid paying the tax on it, so that's kind of nice too.”
    – Jill Schlesinger [13:02]

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Timestamps for Important Segments

• [02:39] – Angela introduces her retirement question
• [03:54] – Current savings and financial assets
• [05:04] – Pension, Social Security, and income sources
• [07:01] – Monthly spending needs and real estate plans
• [08:57] – Withdrawal strategy and emotional hurdles
• [10:58] – Pension decision: lump sum vs. annuity
• [11:54] – Single-stock concentration and tax planning
• [13:21] – Estate planning confirmation
• [13:31] – Closing and lighthearted exchange

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Conclusion: Key Takeaways

• Angela and her husband are well-positioned to retire within 2-3 years, given their substantial savings, anticipated pension lump sum, expected real estate sale, and sensible spending estimates.
• Jill emphasizes the importance of giving oneself “permission to spend” in retirement, especially after decades of diligent saving.
• Working with a planner can reinforce confidence in the plan, but flexibility and regular review will remain important.
• Smart tax planning with concentrated stock through charitable or family gifting can add value.
• Final encouragement: Retirement transitions can be more psychological than mathematical—planning is about both money and mind.

For those considering early retirement: this episode is an excellent, pragmatic blueprint for running the numbers, addressing emotional readiness, and structuring a flexible plan.

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For more practical advice like this, listeners are encouraged to check out Jill’s resources, newsletter, and related podcasts at jillonmoney.com.

Transcript

[A]

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[B]

Hello. Hi, Jill and Mark. I'm so excited to be here today. I wanted to get some advice on retirement and possibly walking away in two years. My husband is younger than me and he's going to retire next summer. And so I'm trying to decide if or how many more years I really want to stay working and what that looks like.

[A]

Okay. How old are you, Angela?

[B]

I'll be 57 in March.

[A]

Okay. And how much younger is he than you?

[B]

He is 55. He'll be 55 next August.

[A]

Dude, you made it sound like you married a 35 year old. So I was excited for a second, but. Okay. They're like the same age. Yeah, exactly. Okay, so what is the like for you? Why do you feel like the early retirement is the right thing for you? What do you think? Are you hating work?

[B]

No, I'm good. But it's just, you know, I've been working for a long time and I just kind of want to have a plan. And now as we're getting closer to that timing, it's getting more complicated because I'm very kind of scared of, you know, what to do. And I know I can take it day at a time, but I just feel like I'm ready to walk away from the corporate world in a couple of years.

[A]

That corporate world really does grind you down a bit. It really does. So, Angela, do you guys have kids?

[B]

We have one. She's 21, in last year of college. And we have a 529 that's covering off on that.

[A]

Okay, great. Fantastic. I hope she's going to UT or something nice and helpful to you guys. Tell us about the amount of money that you've saved.

[B]

So my husband and I both have worked and contributed to 401ks over the years. So the majority of the pre tax dollar or. Yeah, pre tax dollars are in 401ks? A little bit in Roth. 401? Yeah, 401k Roth, but mostly, mostly pre tax. So his retirement is about 1.2 million.

[A]

Okay.

[B]

And mine is between two companies, about 1.3.

[A]

And what about the Roth assets? About how much in there?

[B]

I mean, I would say maybe 10%. Not that much. We really.

[A]

Of the total of this two and a half million bucks, about 2%. 10% is in Roth.

[B]

Maybe. Yeah.

[A]

Okay. What about anything else? Like, will either of you be entitled to a pension?

[B]

So my husband will. He is adamant. He will take a lump sum.

[A]

Okay.

[B]

He's estimating that to be about 500,000.

[A]

Okay, no problem. You will not have a pension, but you'll both be entitled to Social Security. Yes.

[B]

Correct. Correct.

[A]

Do you know those amounts?

[B]

Yes.

[A]

Give it to me.

[B]

So 62 for him is 24.99. 62 for me is 2,499.

[A]

Down on like 62. Give me full retirement age.

[B]

Is that 67?

[A]

Yep.

[B]

3,665 for him.

[A]

And yours?

[B]

3,629.

[A]

Good. Are you guys both in good health?

[B]

Yeah. Yes, why not?

[A]

What about non retirement assets?

[B]

We have a brokerage account with about 50 grand in it. Cash savings, about 50 grand. I have some stock at about 50 grand, which I have a side question on that too.

[A]

Okay. And this stock granted to you or you bought?

[B]

Granted to me through my company years ago, like over 20 years ago.

[A]

So it probably is low cost basis.

[B]

Yeah.

[A]

Okay. All right. It's not a bad problem to have. I have, I have the stock that's made money. That's a good problem, Right?

[B]

Right.

[A]

Okay. What about your house? What's it worth?

[B]

About 450.

[A]

Is there a mortgage outstanding?

[B]

Yes, about 56.

[A]

What's the interest rate?

[B]

3.125.

[A]

Beautiful. Do you own any rental property, vacation homes, anything else?

[B]

We have some commercial real estate. We probably will sell it within the next year and a half, maybe two years.

[A]

Okay. If you sell that and you account for taxes, what do you think you will clear?

[B]

I would say conservatively between 400 and 500.

[A]

Yowza. That's great. That's awesome. You ready for the big magic question which is how much you guys spend?

[B]

Oh, I love that question. I've analyzed that so much, it's so hard. But I'm. I'm going to be conservative, like super Conservative and say 12 grand a month.

[A]

If you were to retire in two years, would either of you be looking at part time income?

[B]

My husband will for sure. I'm estimating his side hustle would be, I mean, at the low end, a grand a month, probably more. I'm willing to work part time. I probably will. But I kind of want to question if I could walk away.

[A]

Great.

[B]

If I have to, I will. But I kind of want to just know that I can walk away.

[A]

So mark 12 grand a month in Texas real money. What do you think about this? They'll have $7,200 in Social Security at age 67. But that's 10 years from now. What do you think about having 12 grand a month coming out of these accounts? Also knowing I just want to be clear with everybody, so we've got $2.5 million of money that's mostly pre tax. There is this half a million dollars of a lump sum pension that will be added to that. So that's $3 million of pre tax. Right. Plus there will be this 4 to $500,000 that will be added to the kitty after you guys sell the commercial property, which we would add to the stock position. So you'll have whatever. Let's say you'll have 500 grand extra in the brokerage account. So you'll have like 550 in the brokerage account. So, Mark, what do you think about 12 grand a month until they're 67? Yeah. Are they comfortable spending down what they have? Because that's what it's going to take, right? You're going to have to take some of that two and a half million bucks, which will now be three because of the lump sum. Right. You got to spend it. How do you feel about it?

[B]

I mean, I guess okay. Yeah.

[A]

I mean, you did save it. Why can't you spend it? You got the kid. Kid will probably inherit some assets. Here's what I think the generalized game plan would probably be. You retire at two years, you're 59 and a half, right.

[B]

Mm.

[A]

You start pulling money out of your pre tax 401k and you pay the tax that's due to. And you're gonna need to use that so that you can live. Right. And so you're gonna pull out whatever you need. You know, between the two of you right now, how much do you earn?

[B]

300.

[A]

So, you know, you'll be. It's interesting, you're gonna be. You're gonna probably be in that 24% tax bracket. Cause even if, you know, I know that we're talking about $12,000 a month, you're probably going to be in that 22% tax bracket. So maybe you will go down a tax bracket. You're going to need to pull the money out of your pre tax account. You're going to pay the tax on it. And if you're freaking out, then what's going to happen is you're going to be like, oh my God, I have to go back to work. Or you can give yourself permission to say, wait, remember that conversation with Jill and Mark and we talked about that we were just going to spend the money that's in this account. People have a hard time doing this. I gotta tell you, Angela, this is, I think, a very difficult decision to make for parents more than Anything else. It really is. So if you're willing to. I think it can work. I do. But maybe you'll change your mind depending on what's going on with your kid. You know, maybe. Maybe graduation from college results in a great job. Life is good on their own, doing their thing, launched, and you're like, great, we're gonna use our money or, oh, still with us. You know, I do think that that does. It's a very big hurdle for a lot of folks.

[B]

Yeah.

[A]

I'm curious. I know your husband's set on the lump sum. Did you ever see what the monthly annuity numbers were?

[B]

Yeah, we did. We got the whole, like, you know, calculations. But he is dead set.

[A]

I'm not getting in the middle of that market. A dead set Texan, Really? Like, come on, there's no way I'm getting in front of that train.

[B]

Exactly.

[A]

So. All right, that's fine. And he's managing the money and you're managing your money or like, who's managing the money right now?

[B]

So we're doing that both individually, but also we're testing out a financial planner. So trying all the things. Yeah.

[A]

All right. What does a financial planner say about your two year game plan?

[B]

They say, we're good, but I was going to work till 60 at least. So, I mean, that's fair, that's fine.

[A]

It's good. But I mean, if things go great guns, you do something different. Let's talk about your stock that you're like, I have too much money in one stock.

[B]

So we only have, you know, I've got one daughter, so I'm wondering if I should just put her as beneficiary and just give it to her later on or just worry about it from a tax perspective.

[A]

I wouldn't worry too much about it. Anyway, is the stock in a company that you would want to own right now or not?

[B]

Yes.

[A]

Okay. There's two things you can do. One is, are you charitably inclined at all? Sure. Okay. You can gift some of that highly appreciated stock to charity. You can be like, hey, I want to now gift five grand to Blankety Blank Church, Blankety Blank Cancer Research. Da da da da da. And you can gift the stock and there's no tax due. If you directly. If you gift the stock to the organization, that's number one. Number two, let's say your sister, your daughter graduates from college, right. And gets a job. Now your daughter is earning. I'm going to make it up $65,000 a year. Okay, maybe you gift her some of the stock, she sells it and she's in a lower tax bracket.

[B]

Okay.

[A]

So that's a possibility as well. I'm sure that the financial planner will walk you through that. But, you know, it's a big bet to have one stock if someone like. But it's not gonna kill you either. It's not like you said, I have $500,000 in this one stock. But, you know, you can probably avoid paying the tax on it, so that's kind of nice too. Right?

[B]

Okay. Okay. You gave me some options. Thank you.

[A]

Exactly. How about the estate planning? You got it. Done.

[B]

All good.

[A]

Oh, man. Anything else on your mind, Angela?

[B]

No. Thank you, though. I appreciate this. I love talking to you guys and listening to you all the time. So thank you.

[A]

Thank you so much. Is Landman TR what happens in Texas? And is that. Or Hunting Wives? Are. Are either of those things true?

[B]

Landman? Oh, my gosh. My Texans husband has a few issues with it, but we still watch it. It's great.

[A]

Okay, good. It's a. It's paramount. It's the company I work for. What about Hunting Wives, that crazy show?

[B]

I have not tackled that one yet.

[A]

All right, tackle that. Get back to us and let us know. It's. It's a little bit crazy of a show, so I'm going to just put it out there. All right. Angela from Texas, good luck. Let us know if there's anything else we can do. If you are looking at your future and you got some game plan that's percolating, you want to know is this sane? Is this right? Is this leading me towards where I'd like to go? Get in touch with us. Go to jillonmoney.com, click the contact us button, write us a note. And if you'd like to join us on the program, just check the box. Mark does everything else. He's so good about that. And while you're on the website, you can check out all the content that lives there. Our. Our free weekly newsletter, our blog. We've got another podcast, it's called Money Watch. We drop that on the weekends, so you can certainly subscribe to that as well as this program. On the Odyssey app or wherever you find your favorite podcast, we ask that you lift someone up. Come on, guys. Everybody needs a little boost. Change your work, change your wealth, change your life. Thank you for listening. We'll talk to you tomorrow. Foreign.

[C]

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[D]

It's Draymond Green. I'm back for my 14th NBA season and my podcast, the Draymond Green show is back, too. This season, I'm breaking down games, reacting to the biggest NBA stories, and sitting down with teammates, rivals and culture shapers. And trust me, I'm not holding back on the court or on the mic. Two new episodes every week. New segments, big conversations. Real basketball talk for the real hoop head. Listen to and follow the Draymond Green show wherever you get your podcast. We're back. We're better. Let's get it.