Episode Overview

Podcast: Jill on Money with Jill Schlesinger
Episode Title: Burned Out in Tech, Can I Retire at 49?
Date: December 24, 2025

In this episode, Jill Schlesinger speaks with John, a longtime tech worker from Boston experiencing burnout as he approaches his 49th birthday. John wonders if he can retire early while maintaining his family’s lifestyle. The conversation dives deep into his finances, options, and emotional readiness for a major life change. Jill, with her hallmark warmth and clarity, breaks down John’s situation and dispenses practical, jargon-free advice for anyone considering their own “great money reset.”

Key Discussion Points and Insights

1. Setting the Scene: Holiday Rituals and Podcast Announcements

• [01:16–04:18] Jill and her producer Mark banter humorously about Christmas Eve traditions and the Italian “seven fishes.” They briefly discuss updates to the show’s website and subscription offerings—for listeners to interact more with the Jill on Money community.

2. Introducing John from Boston

• [04:18–05:54]
  • Jill jokes about Boston’s “town” feel compared to New York City.
  • John is hosting Christmas for both immediate and extended family, with a mix of traditional holiday foods and a special Argentinian treat, sandwich de miga.

3. John’s Dilemma: Burnout and the Retirement Question

• [05:54–06:21]
  • John shares he’s been in the tech industry for 29 years and feels burned out.
  • He asks: “Can I retire ASAP? Or should I wait until my mortgage is paid off?”
  • Jill answers decisively: “No.” (referring to working just because of the mortgage.)

4. Deep Financial Profile Dive

• [06:21–10:05]
  Jill probes John’s financials in detail:
  • Age: 48, turning 49 soon.
  • Spouse: 43, also recently quit tech in what John describes as a “rage quit.”
  • Children: Three adult kids (29, 24, 20) from a prior marriage, plus a three-year-old with his current spouse.
    • “You did. You are really a glutton. You were all done. Now you got a three year old.” (Jill, 07:17)
  • Income: Over $2 million last year, largely from tech stock grants.
  • Retirement Savings: $1.1 million (traditional), $50k (Roth).
  • Brokerage Account: $4.1 million, fully diversified into ETFs. John didn’t hesitate to “pay the tax” to diversify out of tech company stock.
  • Home: Worth $2.3 million, mortgage of $815k at 5.25% (recent purchase), intended as their “forever home.”
  • Cash: ~$150k in cash.
  • 529 Plan: $30k set aside for the three-year-old’s education.

5. Expenses and Desired Lifestyle

• [10:14–11:08]
  • With mortgage: about $129k/year for baseline expenses.
  • “Probably another 70” (thousand) for discretionary spending.
  • Jill pushes for $20k/month ($240k/year) as a generous estimate.
  • No pensions expected for either John or his spouse.

6. Other Responsibilities and Long-Term Considerations

• [11:09–12:52]
  • No outstanding obligations to ex-spouses or adult children.
  • Some potential for needing to help aging parents in the future, but John expects their own assets to cover care.

7. Is the Money Enough?

• [12:52–14:45]
  • Jill and Mark analyze the numbers:
    • $4.1 million in brokerage could likely provide ~$150k/year safely—but the desired budget is closer to $200k+.
  • "It’s more like that money would generate, like, I would say, like, more like $150k a year, not the $200k a year.” (Jill, 13:28)
  • Mark and Jill discuss options: Work a few more years? Cut spending? Find part-time income?
  • John contemplates giving notice in May, “playing it out” through the year to cash in more stock grants, and then paying off the mortgage.

8. A Path Forward: Pay Off the Mortgage, Reduce Fixed Expenses

• [14:45–16:36]
  • If John clears the $815k mortgage on schedule, fixed expenses drop to ~$71k/year—a “game changer” in Jill and Mark’s view.
  • Jill: “If that… mortgage is gone… then sure, this probably works.” (Mark, 15:09)
  • Potential vulnerabilities: a bear market could delay things, but John is young, employable, and open to new opportunities.
  • Jill’s concern: “Can you downshift into something else… have fun, enjoy your 3 year old, all that, but you know, you got a lot of time, man.” (Jill, 16:14)
  • Mark jokes: “One month with a three year old, he’s gonna be itching to get back into the work.” (16:14)

9. Next Chapters and Non-Financial Considerations

• [16:36–17:06]
  • John plans to “lean into the dad thing” and maybe take on pro bono tech work for charities or causes he cares about.
  • Estate planning is complete, as are his parents’.

10. Managing a Major Life Transition

• [17:06–19:19]
  • John is self-managing investments: “The plan has just been, you know, put it in there and just don’t touch it. And it’s been working fairly well.”
  • Jill’s advice: boost cash reserves before leaving work—ideally one year of living expenses on hand as a cushion during the transition.

11. Notable Quotes and Key Takeaways

• On Diversification:

  • “I'd rather just pay the taxes, diversify, and hedge my bets a little.” — John (09:05)

• On Career Windfalls:

  • “Sometimes you’re lucky because of the sector you’re in... If John were, you know, an academic...he wouldn’t have this kind of net worth. You’re in a sector that pays really well. You were able to ride the wave and now I think you’re smart enough to realize, hey, this takes something out of me.” — Jill (17:38)

• On Downshifting:

  • “This is like essentially my whole great money reset thesis, which is if you’re gonna change your work, if you’ve got the wealth to do this, you can change your life.” — Jill (17:49)

• On Family and Money:

  • “You have no obligation to your ex anymore, do you?” — Jill (12:14)

• On Lifestyle Inflation:

  • “I know you probably have had, like, your lifestyle has been creeping higher as you're making more money, but you can do this, so it’s exciting for us.” — Jill (19:19)

• On Options and Security:

  • “He is living a life that I think is commensurate with the income that he and his wife have had. And now he's got choices. And what is better than having those choices?” — Jill (19:40)

Important Timestamps and Segment Highlights

• 05:54 — John introduces himself and shares burnout concerns
• 07:47 — Details on income, investments, and family
• 09:41 — The "forever home" and mortgage specifics
• 10:45 — Details of living expenses and desired lifestyle
• 13:28 — Jill’s calculation on sustainable withdrawal rate from investments
• 14:31 — John’s proposed plan: notice in May, mortgage payoff, reduced expenses
• 15:09 — Mark and Jill green light the revised plan if the mortgage is paid off
• 16:36 — John’s vision for post-retirement life
• 17:38 — Jill’s core takeaway on luck, sector, and readiness for “the great money reset”

Tone and Final Thoughts

Jill’s tone is practical, supportive, and a little playful. She recognizes the privilege and luck in John’s situation but never diminishes the seriousness of making such a big life decision. There's an undercurrent of empathy for listeners who aren’t “$6 million tech people”—with clear encouragement that understanding your choices is empowering at any level. The episode reinforces Jill’s ongoing message: with good planning, honest assessments, and a bit of luck, you can take control and reset your life and money.

Suggested for Listeners

If you're wondering if YOU have enough to make a big life change, or how to approach a personal “work reset,” this episode and Jill’s approach are a practical, kind, and refreshingly honest place to start. For personal questions, listeners are invited to visit jillonmoney.com and use the “Contact Us” button to get Jill’s advice.