Jeremy Jackson’s Tiny House Journey: From Fear to Freedom on the Road

Jeremy Jackson was one of the early pioneers of tiny house travel. After building his own Tumbleweed-style tiny house over the course of a year—mostly by himself—he hit the road to explore America. His story offers valuable insights for anyone considering the mobile tiny house lifestyle.

In this interview, Jeremy shares his motivations, fears, and the realities of those first days on the road with a tiny house in tow.

The Interview: Jeremy’s Tiny House Story

THT: What made you decide to start building a tiny house?

J: I woke up one day feeling frustrated with the world and my own life. My business was dying and I have been suffering from an industrial injury. Everything was crashing down on me.

I started to ponder about what would happen when my mother and siblings would pass because I am the youngest. At the time I was living with my mother. Well that evening I checked my email and stumbled onto the Yahoo! article which featured the tiny house movement and Jay Shafer.

I was instantly hooked from that moment on and I saw a spark of hope. I spent the next few months learning everything that I could on how to build a tiny house until I came up with a plan to build one myself because it made good sense to me.

I decided that if I were going to commit to building my own tiny house, I needed to get to it without allowing myself to over analyze the possible pitfalls. So I jumped in head over heels and started buying materials whenever and wherever I could get them.

So I sold all of my valuables, including the DJ and Karaoke business, and just started even though I am disabled and on a fixed income because I felt that if I were going to survive, I had to take a risk.

THT: So how long did it take you to complete the tiny house?

J: It has taken me the best part of a year to complete it (mostly by myself) but finally, it’s done.

Photos Courtesy of Jeremy Jackson

THT: Do you have any dreams you hope to fulfill thanks to this project?

J: As far as any aspirations are concerned, I’m not really sure yet. We Americans have allowed ourselves to become so burdened with life’s nuisances and its many stresses, that we have lost track of what’s important.

Happiness is an inward quality that has little or nothing to do with material gains. I believe that a free soul is the true definition of success and the minimalistic lifestyle is the fastest way I know toward achieving that.

I think more attention should be brought to the government on our need to live sustainably without the burden of restrictive codes within our communities.

THT: What were the first few challenges that you faced when beginning to build the house and how did you overcome them?

J: I was instantly faced with the fear that if I built something like this I might run into problems with the government. Jay makes it look so easy, and maybe it is, but for me it hasn’t been. I don’t have a piece of land nor am I an RV’er.

I mean, could I even navigate to these backwoods campsites without disaster occurring? My house is 13’5″ high. Another fear was that the cost of gasoline would jump up an extra $1 a gallon. If I’m not careful I could end up spending the price of rent for an 800-square-foot apartment just driving around to find “home”.

THT: How did hitting the road go?

J: I have, in fact, pressed rubber to the road and headed south into the wind. Lots of wind.

So windy that I wasn’t able to go more than 45 mph and my speedometer was going nuts. It stopped doing that when I detached.

I ended up making my first stop at an RV supply store to see if they had a receiver for my hitch that would allow the house to sit level without raising it above height limits. That cost me another $125 but the owner was nice enough to give me a wind deflector for the top of my cab which is helping.

I was able to reach 50 to 55 mph and I wouldn’t want to go faster than that anyway.

THT: Where did you stay?

J: I had my first Walmart camping experience in Kokomo, Indiana. Then to another Walmart in Marion so that I can get my medications. In both cases I asked permission to stay. They were most gracious and told me it was no problem.

After that, I went back to Kokomo where one of my friends live. I parked my tiny house beside his house for a couple of days.

THT: How have people reacted to your tiny house?

J: The interesting thing is how many people literally attack my house to try and get a look inside. I gave tours to probably 50 couples within two days. They had so many questions and I had so little time.

I really enjoyed showing it off and letting them have a look but there came a point where I literally had to hide so that I could have some privacy. I actually had one person ask me if I was Jay Shafer!

THT: How free do you feel?

J: It has been fun and liberating so far. As I laid in bed last night I noticed how much more relaxed I felt than I had in the past.

I didn’t have to lay there listening to the ramblings and chattering of my brain. I fell asleep quickly and had the best night’s sleep in a while.

I was able to jump up and begin my day without regretting having to do it. I have more energy than usually.

THT: Any final thoughts?

J: Tiny house living closes the door to stress and opens the door to creativity. A place where dreams are born.

I just want to find a place in the sun. My own little piece of heaven.

Lessons from Jeremy’s Journey

Jeremy’s experience offers timeless insights for aspiring tiny house travelers:

• Don’t over-analyze: At some point, you have to stop planning and start building
• Height matters: At 13’5″, Jeremy had to plan routes carefully—know your clearances
• Wind is real: A wind deflector made a significant difference in towing stability
• Walmart camping works: Always ask permission, and most locations are accommodating
• Expect attention: Be prepared for curious onlookers—your tiny house will draw crowds
• The right truck matters: Make sure your tow vehicle can handle the weight, especially in hilly terrain
• Freedom feels different: Many tiny house dwellers report better sleep and less mental chatter

Jeremy’s story reminds us that the tiny house journey often begins with a moment of frustration that transforms into a spark of hope. What’s holding you back from your own tiny house adventure?

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Alex

Alex Pino is the founder of Tiny House Talk, a leading resource on tiny homes and simple living since 2009. He helps readers discover unique homes, connect with builders, and explore alternative living.

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