279: Digital Nomad-ing and Answering All Your FIRE Healthcare Questions w/Amy & Tim from GoWithLess

Health insurance for early retirement? Is that even a thing? If it is, it doesn’t seem self-evident in the United States. For most early retirees within the USA, you have a couple of options for healthcare—make a low enough income to qualify for government-subsidized healthcare or pay an exorbitant amount of money to either buy healthcare upfront or pay out of pocket any time you get sick. But, that’s not a terribly safe way to live, especially when you’re working with a (relatively) fixed income.

Throughout their world travels, Amy and Tim from GoWithLess have had to learn this the hard way. They were originally insured on a healthshare plan but found it far riskier than they would have liked. Now, as they travel throughout the United States, Mexico, and the world, they’re making sure they’ve covered all bases so a random surgery or two doesn’t force them back into the working world.

Early retirement health insurance is one of the biggest reasons that financial independence-chasers stay at their jobs, so if you’re itching to get your post-work-life travel on, listen to this whole episode. In it, Amy and Tim drop gems about finding health (and auto) insurance when retiring early (or abroad). They also discuss the best questions to ask a healthcare provider or broker, what to look for in a healthcare plan, and how to save money with digital nomad insurance.

In This Episode We Cover

How Amy and Tim’s post-pandemic travel plans unraveled in 2020 and 2021

House-sitting, dog-sitting, and other ways to creatively lower your travel costs

“Quick traveling” and the time/mental energy it takes to be a full-time nomad

Roth conversions and using resident-specific tax benefits to convert more

The top questions to ask a healthcare broker when choosing health insurance

Car insurance as a retiree and how to pay less to be more protected

And So Much More!

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