Why I intentionally made myself homeless

Lee Hiskett
4 min readJan 21, 2023

This is the story of my transition from a regular guy who worked a 9 to 5 job into a digital nomad who is now traveling the world and seeing it all.

Background

It all began one winter morning as I pulled out of my driveway and prepared to head off to work.

I had the heater on but it had not yet kicked in, I turned on the radio to get some background noise as I drove to work.

Then I found myself pulling into the company car park. “Oh my god!” I exclaimed out loud to no one in particular but I needed to say something nonetheless.

What just happened? I had driven the best part of 16km along winding country roads without being aware that I had done so. So why was this?

After a few days of retrospection, I realized it was because my life had finally reached a level of monotony that my brain no longer needed to take an active role to a great degree. With this revelation and a few more days of troubled sleep, my exit plan began to form.

I needed to leave the UK and a life of stagnation and drudgery if I wanted to succeed in recovering myself and my happiness.

Planning

First, I needed to offload my excess possessions. This was done fairly easily by selling items, giving them away to friends and family, or donating them to charity.

While this process was taking place I began to research exactly where to go. My main driving forces were budget, lifestyle, and communication/interaction problems.

I analyzed these things collectively as no one element was able to stand out by itself. With my can-live-there-and-not-die approach to my French and Spanish skills, I was able to ascertain that any Spanish or French-speaking country could be included as my proficiency would allow me to ask for basic needs such as food and shelter, etc. without my getting into a situation where I was unable to find food or shelter.

Few places leaped out as the budget would be quite tight so despite my best efforts, South America and Northern Africa were out of the running for mow.

This left Asia, due to some wonderful times in Thailand when vacationing from my temporary home in…

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Lee Hiskett

Currently traveling in S.E Asia. Join the free men, travelling free, living and loving life to the fullest https://wegoodmen.com/membership