Maximizing 529 Rollovers and Tax Minimization Strategies

#647: What if you and your partner want to take a few months – or even a year – off work? 

How do you handle health insurance once you leave your jobs? 

And how do you make sure the time off isn’t wasted, but becomes a launchpad for what’s next?

In this week’s Q&A, we dive into those questions. 

We also cover three more listener questions: what to do with a leftover $125,000 in a 529 account, how one listener landed a fully remote job with a 30 percent raise, and whether you can amend your taxes after a FEMA-declared disaster.

Listener Questions:

Danielle (04:35): “We want a mini-retirement. What should we do about health insurance – and how can we make the most of the time off?” Danielle and her husband want a break, but don’t want to go uninsured, and they also don't want to squander their mini-retirement. We look at what happens when you leave a job, where to find coverage, and how to design a mini-retirement that sparks discovery instead of regret.

Lee (32:17): “We have $125,000 left in a 529 account. No one needs it for school. What should we do?”A six-figure leftover balance sounds great, but it comes with tricky rules. Can you roll it into a Roth IRA? Use it for other programs? Withdraw without a tax hit? We explore the surprising flexibility inside a 529.

Pedro (44:06): “I followed your job search advice – and just landed a new role!”Pedro once struggled with dead-end applications. Now he’s celebrating a fully remote job, a big raise, and better alignment. How did he do it? By targeting the intersection of his skills and industry, instead of casting a wide net.

Melanie (53:35): “I spent $45,000 after a FEMA-declared disaster. Later, Congress passed retroactive tax relief. Can I benefit?”Disaster tax relief is confusing, especially when laws apply after the fact. Melanie asks if she can amend her return to capture new benefits. We talk timelines, amended return rules, and why professional help matters.

Timestamps:

Note: Timestamps will vary on individual listening devices based on dynamic advertising segments. The provided timestamps are approximate and may be several minutes off due to changing ad lengths.

Key Highlights

• How to get health insurance during a mini-retirement.

• Why treating time off as a “science experiment” can reshape your career.

• Smart options for a leftover 529 account (including new Roth IRA rollovers).

• A real listener’s success story: from stalled applications to a remote job with a 30% raise.

• What to know about amended returns for FEMA-declared disasters.

Resources

Pedro's original question on Episode 605

Healthcare.gov — ACA marketplace for insurance enrollment

The Power of Fun by Catherine Price

Digital Minimalism by Cal Newport

Freedom app — tool for blocking distractions

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