How This City Boy Became a Homesteader


 Have you ever felt like you’ve lived 2 separate lives?  I can tell you that I sure do. My first life started 40 years ago in Los Angeles, CA.  Santa Monica to be exact. It was an urban jungle by the sea, but for me it was home. Some of my earliest memories were of me playing at the beach, a strip of sand on the edge of a sea of concrete.  I grew up to love the ocean, especially while I interacted with it thru surfing. Surfing was my life. I’d scour the LA coastline looking for waves. If I went a day without surfing, I would begin to feel anxious.

Driving on the freeways, stuck in traffic, only to find the best waves with 100 other surfers already out, I just thought that was normal.  Born and raised in LA, I never knew what open space was. I remember it wasn’t until I was 15 years old, while driving at night on a road trip, that I saw a break in the city lights between towns. It dawned on me then the vast expanse of concrete that I lived in.   LA was one BIG town with city lights that went on forever..

That experience opened my eyes.  I now had a yearning. I craved open space.  I began to find it thru surf trips to Baja California and up the central coast of California.  It all changed for me on a trip to Kauai when I was 18 years old. It was a paradise. Warm water & great weather.  World class waves. Beautiful nature. And something new to me, food growing on trees. I knew this was it. I had to find a way to live in the islands.

That short trip planted a seed.  A seed that kept on growing, until one day it got too big for its pot.   I remember living in San Diego at the time, feeling like my life was going nowhere, when something clicked.  I think it was when I first learned about permaculture through a random internet search. It was the answer I was looking for.  Best of all, there were a lot of farms in Hawai’i that practiced Permaculture. I had to do it. I began looking at land on Hawai’i Island where all the permaculture farms were and to my surprise, I saw lots selling for $3000!  It was a sign. I could afford land in Hawai’i!! I had never been to the Big Island before, but hey, it’s Hawai’i isn’t it? I sold most of my stuff, packed a couple surfboards and clothes and I was on a plane to Hawai’i. Five years after that first trip to Kauai, I finally moved to Hawai’i. My second life was about to begin.

The start of my Homesteading Life
I landed on a farm just outside of Pahoa on the Eastside of Hawai’i Island as a WWOOFer (Willing Worker on Organic Farm) and stayed there for almost a year.  It wasn’t as amazing as Kauai, but I fell in love with the place anyways. Beautiful nature. Fun waves. Cool people. Plus, living at the farm, I got to experience growing food for my first time.  It made complete sense to live this way.

I soon set out on my journey to find a piece of land of my own.  I didn’t have much cash so I purchased land that was on the low end of the price scale.  With money saved up from a few years working in California, I was a proud owner of ½ acre of secluded forest property halfway between Honoli’i and Poho’iki, the 2 best surf spots on this side of the island.  Another reason I chose where I did was because I was looking to build off grid and unpermitted, and in my subdivision there were plenty of both.

It’s so exciting having a piece of land you can call your own and I was ready for the challenge.  With not much money left after the purchase of the land, I cleared a little of the forest by hand and moved my Van onto the property, which became my home for the next 2 years.  My homesteadin’ journey had begun. It took some odd jobs, strict budgeting and some luck, but after 6 months living in my van, I was able to have enough money to pay for a dozer to clear some land to make way for my new home and garden.  I did make sure to save as much of the native Ohia trees as I could in the process.

Then, slowly but surely, I built my first home with my own two hands, with crappy plans I bought off the internet.  It cost me $10k, which included a 20×20 home, solar power and water catchment. Some of the materials I was able to scrounge, but Hawai’i’s second hand supply is pretty slim pickins, so most of it was purchased new.

I remember the day I called the tow truck company to take my home, the Van, off my property.  It was a glorious day. Over the 2 years it began a slow decay, to the point where every night, the first 10 minutes were spent eliminating flying cockroaches so I could get a good night sleep.  But that day was over! I could finally say goodbye to my van and hello to my new home. I felt like I was moving into a palace.

The Reasons I Homestead Keep Growing
Since then, I’ve built up an edible food forest, met my wife and had 2 lovely children.  I get to raise my kids in a beautiful setting inside a home I built. I have no mortgage and no pressure to bring home the bacon.  In fact, after 6 years of raising the kids as a stay at home mom, my wife wanted to switch roles and get a job. So now I stay at home.  I manage the homestead mostly along with a little help from the kids. I fix our cars. Repair the appliances. Tend to the garden. Manage the chickens.  Make home improvements. Manage our finances. Cook the food. Educate my kids. Having these skills gives us more freedom.

I live my life close to my ethics and morals.  We have minimized our tax burden to the state. Very little of our tax dollars goes towards building bombs or destroying the environment.  In fact we get back way more in a tax return than we pay out, thanks to child tax credits. I use surplus time planting trees around the island.  Trees that will feed and help battle climate change. I get to choose my life, not have it chosen for me. These were not the original reasons I chose a homesteading lifestyle, but they sure are great additions to my original purpose.

I started off wanting to build a simple life where I can grow my food and surf.  Now I have that, plus way more than I could’ve ever imagined.

Why do you want to live off grid?  Having a why makes off grid living that much more of a reality.  Leave a comment below to share your why and begin your path to off grid living today.

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Sean Jennings

Sean has been living simply Off-Grid in Hawai'i for over 18 years. He lives debt free on Hawai'i Island with his family and over 40 chickens. When he's not tinkering around the homestead, he's off exploring the shorelines for fish & surf.

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