Episode Overview

Podcast: Jill on Money with Jill Schlesinger
Episode: Can We Run Off to Travel the World?
Date: October 21, 2025
Host: Jill Schlesinger, CFP®
Main Theme:
Jill answers a listener's question about whether she and her partner can financially afford to take an extended break from work to travel Europe for four months, potentially leading to a semi-permanent lifestyle change or partial retirement. The discussion centers on financial independence, risk, re-entering the workforce, and how to plan for major life changes without jeopardizing long-term security.

Key Discussion Points & Insights

1. Introduction and Listener Context ([03:34]-[04:39])

• Guest: Jessica, 51 (soon 52), long tech sales career, calling from Seattle.
• Goal: Take about a year (or shorter/longer) sabbatical to travel Europe with her partner.
• Relationship & Finances: Five years together, maintain separate finances, independent estate planning.

Jill:
"What someone else's desires are, what your next door neighbor's doing...has nothing to do with what you want to do." (01:38)

2. Personal Finance Snapshot ([04:43]-[10:41])

• Jessica:
  • Income: $350K–$500K/year (tech sales; variable comp)
  • Assets:
    • Primary home: $680–700K (mortgage: $190K @ 2%)
    • 401(k): $35K
    • Rollover IRA: ≈$1M (pre-tax)
    • Brokerage account: $1.5M
    • High-yield savings: $760K (originally earmarked for a home, now potential travel fund)
  • Expenses: ≈$90K/year (~$8,500/month, includes buffer and health insurance)
  • Kid: 24, mostly independent, still on her health and phone plan.
• Partner: 51, small business owner, financially stable, not combining finances for this plan.

Jill:
"I hope one of you has a lot of money saved. Since you said you've had a long career in tech, I'm thinking you might be the one who has the lots of money socked away. Is that the case?" (04:04)

3. Logistics of the Travel Plan ([06:59]-[11:33])

• Plan: Four months travel, Europe (maybe longer), house will remain unoccupied (not rented).
• Work: Would need to quit the job (can't take a leave of absence).
• Travel Budget: $7,600–8,000/month in Europe, estimates $25K–60K for the whole trip, including U.S. living expenses.

Jill:
"The high yield savings of 760...you're going to burn up 60 grand. Like, that's my European adventure, is 60 grand." (11:00)

Jessica:
"That is actually more exciting than a cool house." (08:34)

4. Can She Afford to "Run Away"? ([11:33]-[17:27])

• Can Jessica's Savings Support a Permanent Life Change?
  • Jill and Producer run the numbers:
    • $8,500/month needs for life (U.S. or elsewhere), with the current assets, looks possible but with slim margin for error.
    • Success depends on markets, expenses, longevity, and no large unexpected costs.
  • Withdrawal Strategy: Likely involves drawing from savings and brokerage, then IRA after age 59½, with social security later.
  • Work After Sabbatical:
    • Best option: Return and work part time, or at a lower income (e.g., $100K–$175K/year instead of $350K+).
    • This de-risks the plan and builds in cushion.

Jill:
"Can we generate $8,500 a month for Jessica for the rest of her life? In other words, when she comes back from her European adventure, does she have to get a job? It's very, very close. I mean, can it happen? Probably. But every single thing has to go right...there's really no wiggle room." (12:33)

Jill:
"What would be more likely is you go take your romp, have an amazing time, you return, you get a job that maybe where you don't have to make as much money...that, to me, seems like a more realistic way to approach this." (13:52)

• Alternative Scenarios:
  • Can she live in Europe for same/lower cost and never work again? Not safely, unless she drastically reduces expenses.
  • Can she take on work that she loves, outside of tech, at a lower salary (even $50K/year)? Yes, with caution.

Jessica:
"Absolutely...the question is, is it something I really love to do that's outside of tech...do I need to sort of earn more in the 175? Because that's very possible as well." (14:39)

• Unique Value of Sales Skills:
  • Jill strongly advises not to undervalue sales experience:
    "It is a magic skill, Jessica. It is magic. People don't know how to do it. And if you are good at it, it may mean that you take that skill to something else." (16:34)

5. Tactical Recommendations & Next Steps ([17:14]-[19:40])

• Before Leaving:
  • Button up estate planning
  • Set up health insurance for travel period and after
  • Make post-trip plans for deploying the $700K idle in savings into investments

Jill:
"By the end of 2026, maybe it's a half a million of the 760 has to be invested. Has to go into that brokerage account to get it working." (19:21)

• Networking While Abroad:

  • Use time before/during travel to network and line up future, less demanding or more enjoyable work.

• Travel Itinerary:

  • First Japan, then Portugal, Spain, France, Italy, ending with Ireland and Scotland. (18:41)

Notable Quotes & Moments

• Jill on Lifestyle Choices:
  "If you are thinking about doing something, some goal that you have and you want to run it past two people who are certified financial planners…then this is the show for you." (02:12)

• On Reality of Early Retirement:
  "You're really young and…I hope you have lots of longevity in your genes…if your expenses…are $8,500 a month…we're going to have to be willing to spend down some money. I don't know how you feel about that..." (11:54)

• Jessica on Priorities:
  "It would mean working not at all or working less. And that is actually more exciting than a cool house." (08:34)

• Jill on Sales Skills:
  "I would be careful not to throw away just how important that skill is of selling, because I think that is quite valuable no matter where you go." (16:56)

Important Timestamps

• Listener Introduction & Context: [03:34]–[04:39]
• Current Financial Position: [04:43]–[10:41]
• Travel Plans and Budgeting: [06:59]–[11:00]
• Sustainability Analysis: [11:33]–[17:27]
• Career Pivots & Sales Skills: [13:52]–[17:14]
• Planning Before Traveling: [17:14]–[19:40]
• Travel Itinerary Reveal: [18:41]

Overall Tone

Warm, direct, and practical—with Jill offering “tough love” and realistic financial planning wisdom while rooting for Jessica’s dreams and encouraging listeners to take informed, personalized leaps.

Actionable Takeaways

• Take time to run your own numbers if you’re considering a major life change.
• Don’t undervalue your transferable skills when considering a post-corporate career pivot.
• Leaving a high-paying job for adventure is possible, but build in margin for error and future security.
• Major shifts are best supported with proper insurance, estate planning, and thoughtful investment of idle cash.
• Use sabbatical periods to network and prepare for future, fulfilling work.

For listeners considering similar adventures:
"Can you run away? Whether it's four months, six months, can you do something different in your life? Let us help you work through it." —Jill [19:40]