When friends and family find out that we’re planning to spend (at least) the next 500 days on the road, the first response is usually an animated “amazing!” quickly followed by a puzzled “…how?”  What I suspect that question is really getting at is: “how on earth are you going to pay for this?”

So, how exactly will we pay to travel full time as a worldschooling family of five?  It’s an entirely legitimate question–and one that we intend to answer right here over the next couple of years.  

When Kat and I married 15 years ago, we had negative net worth, thanks largely to my massive student loan debt. We’ve been fortunate that our professional careers have allowed us to save over the years, and we’ll be relying on that capital and investment income to see us through.

The nature of our jobs is such that we move every few years, so we don’t own a home and are very familiar with the idea of picking up and relocating. Our assets are liquid, which gives us an enormous amount of flexibility.  Financially, at least, we’re not tied to any one place.

All this helps, but we’re still preparing ourselves for a massive lifestyle change.  

Standard Disclaimer: We are not financial advisors. In fact, most financial advisors would likely view our 500-day ‘unretirement’ as a cautionary tale rather than a strategy.

We’re both leaving jobs that offer guaranteed pensions, and, in my case, an annuity that would begin immediately if I worked for just five more years.

To walk away from that is not financially sound.  Really, none of this is.  

We have good, stable jobs. When we’re overseas (which we have been since 2011), housing is paid for, and so are the kids’ schools.  By most conventional metrics, we’ve made it to a good place.  

It is entirely reasonable to think we’re crazy for walking away from it all.  We might be.

What Kat and I have come to believe is that, at this moment, we can’t let the financial aspects dictate our next steps. We do recognize how fortunate we are to be able to make this decision with some confidence that we’ll be alright for a while.

Some people jump into this kind of life without dwelling much on the financial aspects. I genuinely admire that. But it’s an approach that’s increasingly foreign to me, especially as I settle into life as a middle-aged father of three. 

Money aside, this is simply the right decision for us. The nature of our work has changed, and it is no longer possible to reconcile our morals with our professions.  At the same time, spending more time together as a family has become our greatest joy–and our greatest ambition.

If ever you are forced to jump from a burning building into a turquoise sea, I suspect you’d make the same decision.  

Here’s hoping there are no sharks. 

Over time, this section will grow. We plan to share what we spend, what surprises us, and what we get wrong. Check back in May for our first deep dive into how we’ve developed the budget and how we manage finances on the road.

While we’re happy to share our financial journey, please remember that we are not financial advisors. Our path involves specific risks and trade-offs that may not be right for everyone. Please see our full Terms of Service for our complete financial disclaimer.