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

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

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.

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.

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]

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

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.

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