Jill on Money with Jill Schlesinger

Episode: Can I Take a Break? • Date: September 11, 2025

Overview

This episode of Jill on Money features host Jill Schlesinger and co-host Mark fielding listener questions that range from annuity advice and Roth IRA rules to taking career breaks and preparing for early retirement. In their signature candid, practical tone, they offer insights to demystify financial decisions—especially for those facing inflection points in life and money. The episode also acknowledges the significance of September 11th, weaving in personal reflections as New Yorkers.

Key Discussion Points and Insights

9/11 Reflections

• Jill and Mark reminisce about their experiences on September 11, 2001, emphasizing the personal and emotional impacts of that day.
  • Jill: “It's September 11th and Mark and I are both New Yorkers and... we do like to mark this, this moment.” [01:43]
  • Jill shares that not being in NYC that day reaffirmed her desire to move back:

    “It is such a strange thing for me... to be a New Yorker but not be in the city for that was a very weird feeling. It was actually probably the moment I knew that I had to move back...” [03:21]

Annuity Versus 401(k): Should I Move My Money? (Joe’s Question)

• Listener Joe (60, still working) is advised by his “advisor” to move half his 401(k) into a 6-year annuity.
• Jill’s Analysis:
  • Strongly advises against the annuity, noting the advisor is acting as a salesperson, not a fiduciary.
  • Key points:
    • No one can predict the market—“This is baloney. I hate this advice.” [07:02]
    • Annuities often benefit the seller via high commissions.
    • Suggests Joe consider managing his own investments or finding a true fiduciary advisor.
  • Memorable Quote:

    “This is a terrible idea, number one... I think you might want to consider shopping around your advisor relationship.” [07:35]

Roth IRAs and The Pro Rata Rule (Anonymous Listener)

• Question: Can my husband do a backdoor Roth IRA if I have a rollover IRA?
• Mark: “The answer is no. But he can't contribute. He would have to do a backdoor Roth.” [09:41]
• Jill: Explains that the pro-rata rule applies only to the person with the IRA, not the spouse, and recommends looking into Roth 401(k) availability. Also suggests consolidating old IRAs into current 401(k)s to facilitate backdoor Roths. [09:45-10:11]

Roth vs. Traditional Contributions, and 72(t) Withdrawals (Darrell’s Question)

• Listener Darrell wonders about the advice to use Roths when tax rates haven’t really risen in decades and asks about utilizing 72(t) for early retirement.
• Jill’s Take:
  • Agrees that historical inertia may support pre-tax contributions for those in high brackets but notes the flexibility of having after-tax assets.
  • Points out the rigidity of 72(t) withdrawals and that future tax rate increases are likely based on national fiscal outlook.
  • "I really don't love the idea of being locked into anything.” [12:44]

Burnout and Taking a Break from Work (Jackie’s Question)

• Listener Jackie (39, NYC, $185K salary) is burned out as a primary caregiver and wonders if she can afford to take a break.
  • $480K in Roth assets, $133K in traditional, $49K brokerage, $85K in cash, $4K/month spending, and likely property inheritance.
• Mark: Empathizes but notes concerns about re-entering the workforce, especially in a slowing job market. [15:49]
• Jill:
  • Supports the idea if Jackie is emotionally and financially prepared.
  • Suggests talking to her employer about a leave first.
  • Cautions about potential delays in re-employment:

    “If you feel comfortable that you can land a job in January, then sure, there's no problem doing this. But just beware that the job market is slowing down, and things can change very quickly.” [16:27]

Credit Monitoring Memberships: Are They Worth It? (Sue’s Question)

• Sue is paying for Experian, TransUnion, and LifeLock, wants to cut costs.
• Jill & Mark: Recommend dropping all three and simply freezing her credit, as it’s more effective and free.
  • Mark: “...the best course of action that you can possibly take is to just freeze your credit files.” [18:14]
  • Jill: “Just freeze it, Sue... Freezing your credit, gang, it means that nobody can open up your credit record for anything, not even you. You have to unfreeze it to go get new money.” [18:24]

Pursuing a Flexible "Off Ramp" to Retirement (Cynthia’s Question)

• Cynthia (45, $143K salary, $6K/mo spending, expects to drop to $3K after mortgage payoff, targeting simplified/part-time work)
  • Projecting $1.6M in 401(k) by age 59.5 and $4,800/month Social Security at 70.
  • Seeks to know if taking a 50% pay cut to decompress is viable.
• Mark: On the surface, doable given low spending, but cautions that things can change and encourages regular re-evaluation. [22:10]
• Jill: Endorses the plan as a good framework, emphasizes monitoring and adjusting for inflation, income, and job realities.
  • “If it makes you feel good to just sort of say like, this is my generalized game plan, then great. The one thing just to be careful about... is that sometimes you say, like, ‘Oh, I can go part time and I could take a pay cut’—like, yeah, maybe. Sometimes things don't work out that way.” [22:28]

Listener Thank You: The Impact of the Show (Alex’s Letter)

• Alex, a recent CFP, credits the podcast for inspiring a successful career change into financial planning.
• Memorable quote from Alex’s note:

  “Listening to your podcast, hearing the advice you gave, and learning from Mark's own journey to becoming a CFP made me think of maybe I can do this too... What started as a personal passion has now become my career. And you both played a big part in making that happen.” [24:32]

• Jill: “Thank you for that lovely note. What a nice way to end the show.” [25:08]
• Mark: Confirms Alex is now a CFP in Chicago. [25:03]

Notable Quotes & Memorable Moments

• On Predicting Markets:

  “First of all, no one is really very good at predicting market tops and bottoms.” — Jill [07:02]

• On Burnout:

  "I'm feeling burned out. I just want to know if I can take a break from work. I am a primary caregiver for my elderly mom. I've got a demanding job and managing her care for the past several years has taken its toll." — Listener Jackie [15:18, paraphrased by Jill]

• On Taking Action:

  “Don't squander those opportunities. You're not stuck where you are. Maybe there are different things that you, you could be thinking about.” — Jill [05:32]

• On Being Cautious with Career Breaks:

  “If your costs are going down and you only spend Four grand a month... you have money in savings and checking. You could float this. ...But just beware that... things can change very quickly.” — Jill [16:27]

• On Credit Protection:

  “Just freeze your credit. Freezing your credit, gang, it means that nobody can open up your credit record for anything, not even you.” — Jill [18:24]

• On Planning for Early Retirement:

  “I think you're on track and you need to keep retesting the assumptions. That's what I would say. So good luck. Let us know.” — Jill [22:28]

• On Listener Impact:

  “Just wanted you to know that your work makes a real difference in people's lives. I am one of them and I am grateful.” — Alex [24:32]

Timestamps of Important Segments

• [01:43] Reflections on September 11th as New Yorkers
• [06:45] Joe's annuity vs. 401(k) dilemma
• [09:41] Roth IRA backdoor and pro-rata rule Q&A
• [12:25] Discussion of Roth vs. pre-tax contributions and 72(t) withdrawals
• [15:18] Jackie asks about affording a break from work
• [18:14] Advice on credit monitoring memberships
• [18:56] Cynthia’s “off-ramp” retirement plan question
• [24:32] Alex thanks Jill and Mark for inspiring his CFP career

Summary Table: Listener Questions and Core Advice

| Listener | Main Question/Issue | Core Advice/Insights | |---------------|----------------------------------------------------------|--------------------------------------------------------------| | Joe | 401(k) versus annuity in face of market fears | Say no to annuity; self-manage or find a true fiduciary | | Anonymous | Backdoor Roth given spousal rollover IRA | Spouse’s IRA doesn’t block backdoor; look into 401(k) roll-ins| | Darrell | Roth vs. pre-tax & early withdrawal using 72(t) | Flexibility matters; beware rigid 72(t) schedule | | Jackie | Can she afford to take a break from work (burnout) | Financially yes; be wary of employment market risks | | Sue | Keep credit monitoring memberships? | Cancel all, freeze credit instead | | Cynthia | Reduce work, spend less, wait for SS/401(k) in retirement| Plan looks good; revisit assumptions regularly | | Alex | Listener's thank you for career inspiration | Celebrated by hosts; underscores positive impact |

Overall Tone and Takeaways

Jill and Mark approach every question with empathy, candor, and a voice of lived experience, favoring flexible strategies, expense management, and caution against expensive or irreversible financial moves—especially those promoted by advisors with conflicts of interest. The episode is a warm reminder of the real-life impact of sound financial advice, celebrating both personal and professional growth among listeners.

If you’re considering a big financial or life change, Jill’s recurring message is: evaluate, talk it out, know your numbers, and keep retesting your assumptions as life evolves.