Jill on Money with Jill Schlesinger

Episode: Should I Go for the Promotion?
Date: October 22, 2025

Episode Overview

In this episode, Jill Schlesinger and co-host Mark tackle a packed mailbag, answering a range of listener questions about the interplay of life and money decisions, including retirement risks, Social Security timing, Roth conversions, mortgage management, and—most prominently—the life and financial calculus behind taking a job promotion when experiencing burnout. Jill’s signature blend of candor, empathy, and practical advice is front and center as she cuts through jargon and typical financial fear-mongering, helping listeners make sound decisions aligned with their values.

Key Discussion Points & Insights

1. Sequence of Return Risk in Retirement

• Listener Nathan worries about early retirement and the possibility of poor market returns having a disproportionate negative impact.
• Jill’s Take ([02:00]):
  • Don’t lose sleep over it; it's generally a risk to be aware of, not obsessed over.
  • The key is to plan for caution by assuming lower returns temporarily and ensuring liquidity for a couple of years’ living expenses.
  • Quote:

    "What I would be looking at is… how would your portfolio perform just assuming a lower rate of return over a multiple series of years?... I really wouldn’t worry about this." — Jill ([02:12])

• Practical Tip: Keep one to two years of living expenses in cash as a cushion at retirement.

2. Tax-Efficient Investment Allocation

• Listener Ann asks which investments are best placed in retirement vs. individual/taxable accounts, especially regarding interest- and dividend-generating assets.
• Jill’s Take ([06:00]):
  • Income-generating assets (bonds, dividend stocks) are generally better in retirement accounts for tax reasons, but not everyone can emotionally “split” their investments this way.
  • Know your tax bracket—sometimes anxiety is out of proportion to actual tax risk.
• Mark’s Nuance: In taxable accounts, use municipal bonds to ease the tax impact.
• Quote:

  "Ideally, the things that create income are better held in a retirement account… Most people can’t manage that emotionally. They really can’t." — Jill ([06:00])

3. Timing Social Security with Military Retirement

• Listener Gary: Age 61, receiving military retirement, wants to know if he should claim Social Security at 62.
• Jill’s Principle ([07:10]):
  • Only take Social Security early if you truly have no other choice. Otherwise, draw on other assets if possible to delay and avoid permanent benefit reduction.
  • Quote:

    "The time we tell people to claim early is when they really cannot afford to live their lives… Otherwise, we’d like to avoid that, truly." — Jill ([07:29])

4. Roth Conversions After Retirement

• Listener Helen wonders why Jill less frequently recommends Roth conversions after retiring.
• Jill’s Insight ([09:00]):
  • She loves conversions in theory, but most people lack sufficient taxable assets to pay the tax bills without sacrificing liquidity.
  • Exceptions exist for those with significant brokerage assets.
  • Mark’s Input:

    "Nine times out of ten, I would say that’s the reason. You gotta have the money on the sidelines." ([09:12])

  • Jill’s Humor:

    "Helen, tell us how much money you have. Come on." — Jill ([09:45])

5. Managing Mortgage Versus Investing Extra Cash

• Listener Kara: Bought a dream home with a seven-year ARM at 5.125%. Debates paying extra toward the mortgage versus investing the surplus.
• Mark’s Perspective ([11:38]):
  • Personally opts not to pay down the mortgage early; prefers liquidity.
• Jill’s Analysis:
  • Depends on one’s full financial and life picture. At Kara’s age and income, focusing on boosting brokerage/investment accounts is likely wiser for flexibility.
  • Quote:

    "I’d rather have access to my money. And you’re young. That’s the piece of it that is important…" — Jill ([13:27])

• Backstory: Kara and spouse have mid-six-figure incomes, substantial retirement accounts, and are in their mid-40s.
• Takeaway: Build flexibility—don’t overly focus on mortgage paydown if it restricts liquidity, especially with pending college costs.

6. Should I Go for the Promotion?

(Episode’s Main Question)

• Listener “West Coast Rob” is 41, single, well-off (net worth over $2 million), but feeling major burnout. A promotion offers a 10% salary bump and 50% greater bonus, but likely more stress. He wants Jill’s advice on whether to pursue it or focus on a more self-directed career shift.

• Rob’s Stats ([15:00-17:00]):

  • Current salary: $250K
  • 401(k): $700K; Roth IRA: $165K; Regular IRA: $462K; Brokerage: $600K; HSA: $85K; Cash: $135K
  • Home is paid off ($500K value)
  • Annual spending: $60K
  • Plan: Two more years at this salary, enhance investable assets, take a break, then seek lower-stress work.

• Jill’s Response ([17:00-18:30]):

  • Absolutely not the time to go for a promotion if burnout is an issue and you’re already in a strong financial position.
  • Promotion should be about excitement, not guilt or pressure.
  • Suggests a diplomatic “not right now” and revisiting later, unless the company draws a hard line.
  • Quote:

    "You are letting this flexibility and all this savings really amount to nothing if you don’t take advantage of it… The only reason why I think you go for a promotion is if you’re like psyched about it; you’re already bummed out and burnt out and I wouldn’t do it." — Jill ([16:50])

  • Mark’s Agreement:

    "No way. I think he kind of answered his own question." ([17:31])

  • Burnout at 41 isn’t sustainable or advisable; financial independence means Rob can choose more meaningful, less stressful work.

• Actionable Suggestion:

  • Rob should talk to his boss candidly, defer the promotion if possible, and avoid burning bridges or quitting prematurely.

Notable Quotes & Memorable Moments

• On Sequence of Return Risk:

  "If it’s really freaking you out, you can keep some extra cash on the sidelines just in case. That’s one of the reasons why we suggest you have one to two years of your living expenses in cash as soon as you retire." — Jill ([02:22])

• On Roth Conversions:

  "If you said to me, like, I have a million dollars in a retirement account, it hasn’t been taxed yet. I have $5 million in a brokerage account. Yeah, let’s go. Let’s just convert and go crazy." — Jill ([09:33])

• On Mortgage Anxiety:

  "Have you saved money for the kids’ education? I need more information. Generally speaking, I like people to feel better." — Jill ([11:51])

• On Promotions and Burnout:

  "If you are 40 years old and you are fried, that’s not great. And I don’t want you to feel locked into a job, especially because many people who are locked in… cannot make a different decision. You know what? You can." — Jill ([18:32])

Timestamps for Important Segments

• 00:40: Sequence of Return Risk in Retirement
• 06:00: Tax-efficient asset placement
• 07:10: Social Security claiming with military pension
• 09:00: Roth conversions post-retirement
• 11:25: Mortgage paydown vs. investing extra cash
• 15:54: “Should I Go for the Promotion?” (Rob’s story and planning details)
• 17:00: Jill and Mark’s advice on burnout, promotions, and aligning work with values

Overall Tone and Takeaways

Jill and Mark bring reassurance, humor, and personal warmth to every question, blending technical advice with reminders to keep financial decisions rooted in real life and personal values. Their advice consistently prioritizes flexibility, liquidity, and emotional well-being over theoretical maximum returns or rigid frameworks. The final segment, around Rob’s dilemma, delivers the heart of the episode: money is ultimately a tool to give you the freedom to live well, not just earn more for its own sake.

Missed the episode? This summary has you covered with the actionable highlights, warm moments, and Jill’s trademark candor—perfect for listeners at any stage of their money journey.