Sell Everything? Some thoughts about strategy before hitting the road.

One of the more interesting message board conversations I read of late was about how people managed their properties and STUFF at home before hitting the road. Did people keep a home base? Did they have rentals that supported them along the way? Or did they throw a Hail Mary and sell everything without looking back? And if they did throw the Hail Mary, did they perhaps harbor a few regrets and in fact peek backwards?

There was a wide range of experiences on the board. Many people maintained a home base, either keeping their home empty or renting it out for income while on the road. Some families had other rentals purely for income but had given up their own homes; others put everything in storage and sold their homes. Still others sold everything and left the United States with a clean slate. Amazingly, these were the people who noted almost without exception that they had no regrets! “Best decision of my life,” wrote one. “Never looked back,” wrote another. The exception was one woman responding to the question of whether people feared they wouldn’t be able to buy back in, particularly in popular and gentrifying areas. “I do wonder if I’d be able to get back in. But what’s done is done,” she wrote from some location in Southeast Asia. Still, there seemed no outright regret.

I was struck by the number of responses on the chain, and the relief – expressed almost with euphoria – by those who let go of everything and jumped into their travels with both feet.

Now, I’m someone who likes security. Or the illusion of security. Clearly there’s irony here considering my background is in reporting on conflicts and their repercussions. As in, war zone conflict. But even in the most unstable of conflict situations, I always knew I had a home to return to. During these forays I mostly rented out my home while I traveled thousands of miles away, and rarely had any difficulties. As a young, single woman traveling, my costs were low and I needed few creature comforts. Then I got older… I became a mother… my body started to creak… and rather than filtering through those $2 hostels with stains on the mattress, I now spent my time wondering how many days I could cut in order to afford one of those fancy hotels with the 100 percent cotton sheets or an infinity pool. I wanted luxury, or at least some version of that that I could afford. And I still felt confident that when the trip was over I could go back to what was comfortable and known in my home state, even if it was not necessarily where I wanted to be.

Which gets me thinking once again about the sell everything crowd. Yes, renting has allowed me to travel with my son while covering costs back in the states. But it has also created untold stress in terms of property management issues, with tenants leaving, things breaking, and other crises that a management company simply can’t handle without the owner on the line dictating directions. If taking a leave from one’s lifestyle is meant to encourage clarity, I have become crystal clear: I do not like being a property manager. But selling everything? The questions that arise are not only about giving up a sense of security in terms of being connected to Place, or giving up a property in an area whose costs are rising so fast that there is no chance of buying back in; it also begs an examination of whether I’d do well managing the cash of a home sale. Would I invest the funds well enough to last through my retirement? Or would I indulge a few too many times on the luxury hotels at the expense of more years of low-key travel? At this point these are all hypothetical questions, but necessary for anyone to explore. If you decide to rent, can you afford a management company while still covering costs? And if not, do you have enough savings to cover the rest while living abroad? Is your trip just a brief exploration or could it become a lifestyle from which there might not be a return? Is the illusion of “safety” (as in property ownership), the ball and chain that will keep you from discovering a new home? Or is it truly a place that will always call you back?

I recently decided to put my home on the market, and after a few weeks with little interest, I cut the price drastically. Then after difficulty with the current tenants refusing to show (7 cancellations!), I took it off the market completely with the intention of waiting out their lease. Plus, I’m not quite at the place where I can sell everything, particularly given the lovely community in which my home is based. But I’m getting closer. Because I want to be one of those people who doesn’t look back. I want one day to write that I sold everything and it was the best decision I ever made.

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