NerdWallet's Smart Money Podcast
NerdWallet's Smart Money Podcast

How to Plan a Sabbatical (and Pay for It), Plus the Hidden Costs of Cash Advance Apps

October 15, 2026

AI Summary

5 min read

When NerdWallet producer Tess bought a one-way ticket to Vietnam, she had a hotel booked for four nights and absolutely nothing else planned. She ended up staying in Asia for three years. That is the extreme end of what a sabbatical can look like, but it highlights a central tension in planning one: the desire for total freedom versus the practical need for structure and money. On this episode of NerdWallet’s Smart Money Podcast, hosts Sean Piles and Elizabeth Ayoola, joined by producer Tess, break down how to plan a sabbatical—whether you have a paid benefit from your employer or have to fund it yourself—and then pivot to a sobering look at the hidden costs of cash advance apps.

The Sabbatical Landscape: Rare, but Not Impossible

Only 5% of U.S. companies offer a paid sabbatical, and 11% offer an unpaid one. That means most people cannot rely on their employer to fund extended time off. Companies that do offer them tend to be in tech—Intel, Microsoft, Adobe, Zillow, Instacart—but the list also includes McDonald’s, which offers eight weeks after ten years of service. The key takeaway: if you want a sabbatical, you will likely have to build the plan yourself, and the first step is simply asking your employer what options exist.

Planning the Sabbatical: Goals, Money, and Healthcare

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What you'll learn

  • 1 (02:19) **Why Sabbaticals Are Rare & Today’s Plan** - Only 5% of US companies offer a paid sabbatical, so most people need to self-fund. The hosts (Sean, Elizabeth) and producer Tess share their personal sabbatical experiences.
  • 2 (04:34) **The Landscape of Sabbaticals (Paid vs. Unpaid)** - Data shows paid sabbaticals are rare (5% of companies), while 11% offer unpaid ones. Companies like Intel, McDonald’s (8 weeks after 10 years), Microsoft, and Adobe offer them.
  • 3 (07:20) **Step 1: Set a Goal for Your Time Off** - Before planning finances, decide what you actually want from the sabbatical. The hosts caution against over-scheduling.
  • 4 (09:36) **Tess’s Unconventional, Unplanned Sabbatical** - Tess quit her job, sold her house, and bought a one-way ticket to Asia for a self-discovery trip that stretched into nearly three years.
  • 5 (12:55) **Visa Logistics for Long-Term Travel** - Tess explains how she managed to stay in Thailand for 2.5 years by doing “visa runs” to nearby countries (Malaysia, Hong Kong) every few months.
  • 6 (15:13) **Length of Sabbatical: Short vs. Long** - The hosts compare the pros and cons of a short, structured sabbatical (5 weeks) vs. a long, open-ended one (3 years).
  • 7 (17:23) **Sean’s Structured Sabbatical Strategy** - Sean used his second sabbatical to take a major professional exam (CFP) and then immediately go on a celebratory trip to Vancouver, BC.

+ Full timestamped outline available in the app

Guests on this episode

Sean Piles Elizabeth Ayoola

Show Notes

Learn how to plan and pay for a sabbatical, plus why cash advance apps may cost more than you think.

How do you plan and pay for a sabbatical, even if your employer doesn't offer a paid one? Hosts Sean Pyles, CFP®, and Elizabeth Ayoola are joined by Smart Money producer Tess Vigeland to answer a listener's question about setting up for extended time off work. They talk about how rare paid sabbaticals are, which companies offer them, and how to set goals for your time away. Tess shares the story of her three-year sabbatical in Asia, and the hosts compare the pros and cons of shorter breaks. They also get into building a sabbatical budget and sinking fund, why debt and emergency savings matter even more when your paycheck pauses, what happens to your health insurance, and what it can feel like to return to work. Plus, ways to get a real break when a sabbatical isn't in reach.

Why might cash advance apps cost more than their marketing would lead you to believe? Senior news writer Anna Helhoski talks with Candice Wang, senior researcher at the Center for Responsible Lending, about new research on payday advance apps. They discuss how these apps differ from traditional payday lenders (and how they don’t), why users may not recognize them as high-cost loans, how an average 232% APR and frequent repeat borrowing can add up, why some state payday lending laws don't apply, and what you could consider before using one.

Explore the Center for Responsible Lending's research on payday loan apps, plus NerdWallet's guides to sinking funds and COBRA coverage:

The Cost of Payday Loan Apps in Your State: https://www.responsiblelending.org/research-publication/cost-payday-loan-apps-your-state

Sinking Funds: The Secret to Stress-Free Expenses: https://www.nerdwallet.com/finance/learn/nerdwallet-sinking-fund-savings

COBRA Health Insurance Eligibility and Alternatives: https://www.nerdwallet.com/insurance/health/learn/cobra-health-insurance

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