The Homeless Homeschool


I always tell people that homeschooling is a complete misnomer…

Because we are never “home” and because we don’t do anything resembling “school”.

Right now, my family is attempting to stretch that definition even further.

You see we just sold our Long Island, New York house. In fact, we have to be out rather quickly, within weeks of this publication.

Except we haven’t decided where we want to go!

The tentative plan is to move into Manhattan and rent a tiny 2 bedroom apartment for a huge monthly sum. In case you aren’t aware how insane NYC prices are consider that one of my homeschool mom friends has four kids and lives in a 900 square foot 1 bedroom apartment on Riverside Park. It costs $4,000 in monthly rent!

Other ideas are hiding out at a family’s non-winterized beach house through the winter. Or escaping to the sunny and warmer clime of Florida (Naples or Miami) before figuring out our next steps.

But what kind of wackos decide to sell their house without any definite plan?

There was no urgency to sell it. We are happy here. The house is plenty big enough and well within our budget.

So why shake things up?

Well there were several reasons.

First, the opportunity to sell our house into a massive NYC real estate bubble is just too great to resist. We can afford to “not work” for several years now if we choose.

Second, to potentially shorten work commute times. If we move to Manhattan, one benefit would be a drastic reduction in “train time”.

Third, I’m over suburbia. I’ve about had my fill of having to drive everywhere: dance classes, soccer games and practices, karate 5 times a week, etc. Actually, it’s not suburbia, but the car! I’m over sitting behind the wheel all day.

Also, I have concluded that the conventional wisdom that kids are better and easier raised in homes rather than apartments is bunk. Backyards are nice, but parks full of kids within walking distance are much better. As homeschoolers we depend on “random kids to play with at the park”, if that makes sense.

Fourth, we need to walk. We need exercise, especially my kids. Urban living, with all its attendant walking, makes exercise automatic. I’ve found that my kids simply do not get enough daily exercise. You know how it is….they are homeschooled so if I kick them outside I will invariably find them sitting under a tree READING BOOKS!

Fifth, I believe socially it’s time to move. After roughly 7 years in one spot, any spot for that matter, the walls of a town start to close in around you. Homeschooled kids are always in many ways growing apart from their local “school” friends. And with my daughter 11 and my son soon to be 13, I can sense that things are getting stale as their local friends are grappling with 3+ hours of daily homework and the increasingly degenerate teenage culture – if you can call staring at iPhones all day long, “culture”.

But again, we may still do something even wilder – like vagabond and travel the world. After already living in Europe (See – Leaving London) we are itching to maybe do Asia.

This is what’s truly awesome about homeschooling.

You can do whatever you want, wherever you want, however you want.

You don’t need a school.

You don’t need a curriculum.

You don’t need a “home” in the traditional sense – just a roof over your head, maybe tonight.

You don’t even need a plan for the future.

In fact I would argue that all of the above are “educational constraints”!

If you haven’t heard of the terms, I’d encourage you to research ROADSCHOOLING and WORLDSCHOOLING. Search on Pinterest and Instagram.

I know – it seems crazy and utterly impossible. It will take some time for you to figure out how you can push your homeschool beyond your current home.

But if you plant the seeds of the idea now, I promise you that one day soon opportunities will present themselves. It took 5 years after I first thought about moving to Europe before it became a reality.

And I have clung to my 917 area code phone number for 14 years and through 7 moves because somewhere deep in the back of my mind I knew I was destined to return to NYC.

Where are YOU destined to go?


Dan (30 Posts)

Husband to Inez. Father of John and Christine. Homeschool Coach, Accelerated Math Teacher. Former derivatives trader and future scratch golfer! Follow our learning adventures at

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