Podcast Summary: Jill on Money with Jill Schlesinger

Episode: Can I Quit My Job at 57?
Date: March 27, 2026
Host: Jill Schlesinger (A)
Guest: Anthony (C), Mark (producer/co-host, D)
Theme: Financial Planning for Early Retirement and Job Transitions

Episode Overview

In this listener call-in episode, host Jill Schlesinger fields a question from Anthony in Texas, age 57, who is considering quitting his well-paying corporate job to take a sabbatical, rediscover interests, and potentially transition to part-time work or other passions. Anthony seeks Jill's expert advice on whether he is financially prepared to make such a move, how best to withdraw from his substantial savings and retirement accounts, tax considerations, and how to structure his future lifestyle and support obligations. The discussion addresses practical withdrawal strategies, the flexibility of renting versus buying a home, tax optimization, Social Security planning, and estate concerns.

Key Discussion Points & Insights

Anthony’s Situation and Goals (04:27–06:07)

• Background:

  • Age: 57, single, no children, currently renting in Texas.
  • Considers leaving corporate job for a "gap year" followed by flexible, lower-stress work.
  • No strong dislike for job but wants the freedom to explore new things.

• Spending & Living Arrangements:

  • Current rent: $1,613/month, considering upgrade to $2,500/month apartment.
  • Current annual spending: $59,000; planning for $72,000 (future estimate, including rent upgrade).
  • Supporting parents: Pays $600/month toward their independent living.

Quote:
"I am getting closer to where I would love to leave my job. And so I need some guidance on, first of all, am I in a position financially where I can do this?" — Anthony (04:30)

Financial & Investment Profile (06:17–08:16)

• Income:

  • Base salary: ~$150,000; total with bonus: $180,000–$190,000.

• Assets:

  • Traditional 401(k): $1,851,000 (equities) + $503,000 (bonds)
  • Roth IRA: $303,000 (equities) + $3,100 (bonds)
  • Brokerage Account: $591,000 (equities) + $70,000 (bonds)
  • HSA: $56,000
  • High-Yield Savings: $162,000
  • Total Assets: ≈ $3 million

• No mortgage or home ownership; prefers renting for flexibility.

Memorable Moment:
Jill: "Good lord, you are a rock star. Okay... Mark, I can't believe I haven't heard you snicker yet. We're about to get hate mail. But, guys, oh my god, he's got $3 million." (08:17)

Retirement and Withdrawal Planning (11:41–14:06; 18:40–22:40)

• Retirement Timing:

  • Wants to give notice at end of year; open to staying for bonus.
  • Would need to fund living expenses for 2–3 years before hitting 59½ (penalty-free withdrawal age).

• Health Insurance Consideration:

  • Anticipates increased monthly costs post-job due to private insurance.
  • Jill suggests planning for ~$7,000/month or $84,000/year for living + healthcare.

• Withdrawal Strategy:

  • Use high-yield savings and brokerage account first for years before 59½ to avoid early withdrawal penalties.
  • Move assets from brokerage into cash as needed to avoid market risk for nearest years' spending.

• Tax Bracket Guidance:

  • Utilize "Rule of 55" (special 401(k) withdrawal without penalty allowed by employer) for flexibility.
  • Jill and Mark strongly advise not fixating on minimizing taxes in the lowest brackets but instead to withdraw up to the top of 22%–24% bracket annually to reduce future required minimum distribution (RMD) "tax time bomb."
  • Consider paying current tax rates rather than risking higher future brackets due to continued account growth.

Quote:
"Take out whatever I could to keep me in the 24, maybe the 32% bracket… Otherwise, you're just like a snowball going downhill, you know? That's the tax time bomb Ed Slott always likes to talk about." — Jill & Mark (19:28–20:08)

• Social Security:
  • Anthony plans to delay benefits to age 70; projected benefit ~$5,222/month.

Renting vs. Buying; Lifestyle Flexibility (08:39–09:14; 17:28–18:39)

• Advantages of Renting:
  • Maintains flexibility, especially if parents' health needs shift.
  • Avoids locking into a particular location or taking on mortgage risk before future plans solidify.

Quote:
"I think that you would want flexibility… What if you found out, gosh, I really want to be not an hour from my parents, I need to be 15 minutes from my parents. That's important to me." — Jill (17:28)

• Anthony agrees:
  "That is exactly why I was like, I really don't want to assume a mortgage because I really like the flexibility aspect." — Anthony (18:31)

Estate Planning and Family Support (24:05–24:46)

• Estate Documents:
  • Anthony has set up beneficiaries and documents but needs to complete notarization.
  • Parents have healthcare proxies and related directives in place, though limited financial assets.

Key Timestamps & Highlights

• 02:11 — Show intro and subscription service plug.
• 04:27–06:07 — Anthony outlines his goal of leaving work, sabbatical, and passions.
• 06:17–08:16 — Detailed run-through of Anthony's assets.
• 08:39–09:14 — Renting vs. homeownership discussion.
• 11:41–14:06 — Social Security planning and supporting parents.
• 17:28–18:39 — Flexibility advantages of renting.
• 18:40–22:40 — Withdrawal strategies, rule of 55, tax planning.
• 24:05–24:46 — Estate planning and beneficiary review.

Notable Quotes

• On Anthony's financial discipline:
  "You have so much money. What was your game plan going to be for Social Security claim at 67 or 70?" — Jill (11:30)
• On withdrawal rates:
  "Should I secure a mortgage before I pull the plug or…" — Anthony (08:39)
• On tax minimization concerns:
  "Dude, get over it. You have $3 million. You're going to pay taxes. Calm down." — Jill (23:37)
• On flexibility and parental support:
  "It's better to preserve that as an option just given where you are in your life." — Jill (17:28)
• On estate planning:
  "Do you have all of your beneficiaries and estate stuff all set up? Because you do have a lot of money." — Jill (24:06)

Summary Takeaways

• Anthony is in excellent financial shape to leave work, fund a sabbatical, and thoughtfully plan his next phase.
• Withdrawal strategies should maximize use of available tax brackets, not just focus on the lowest rates, to avoid larger future tax burdens from required minimum distributions on growing pre-tax accounts.
• Renting offers lifestyle and location flexibility, which is prudent given Anthony's support of his parents and uncertainty about future needs or preferences.
• Continue supporting parents, maximize account flexibility, and periodically revisit estate documents and beneficiaries.
• Anthony is encouraged (with humor and appreciation) by Jill and Mark to move forward with his plan: "Go find something else to do." (24:06)

For listeners considering early retirement, sabbaticals, or major life changes, this episode delivers practical, jargon-free advice—emphasizing the importance of flexibility, tax-aware withdrawal strategies, and the confidence to use well-earned wealth in ways that support desired lifestyles and family needs.