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To Freedom and Back Again

Welcome to Wandering Hills, I’m Jerad Hill, a husband, father, and entrepreneur. I have a bit to break down as to what this is and what I plan to do here so in the first post I will try my best to present a 30,000-foot view of it all and as time goes on I will explain more. The goal is to create more freedom in our family life. Not to be so tied down to the things we get ourselves stuck in. For those interested, I will share how I got here.

My first business was in retail. It started as a brick and mortar store and quickly went online. As I added product lines and services both instore and online, I found myself working insane hours. I would get to the shop around six in the morning to get working on online orders that came in overnight and work on customer repairs that still needed to be completed. I had food delivered or picked up for me every day and often didn’t leave the shop until around eleven at night. Sometimes I had so much work that I just slept at the shop. The shop was open six days a week and closed on Mondays so I could catch up on orders and service work. I did this for several years. Retail was also very stressful because I constantly had to worry about my shop getting broken into by kids who wanted free skateboards and scooters.

Fast forward to the summer of my 2005, I was 25 years old and I knew I could not continue working like that. I had closed my shop down at the turn of the year and was considering the closure of the online store as well. I decided to sell off my remaining inventory and start developing websites as I had been doing some web design and development on the side. I had taught myself how to code out of the need to grow and add features to my online stores over the past five years. I had some money saved up so I thought I would give freelancing a try.

I knew that if I wanted to have a family, I needed to change my lifestyle.

When I decided to sell off the remaining inventory I knew that I could not go on like I was. I had ruined a relationship I was in which was largely due to the amount of time I spent working. I knew that if I wanted to have a family, I needed to change my lifestyle. There was no way I could be a good husband and have any relationship at all with my children if I worked twelve hours each day.

Shortly after starting my freelance website design business I got into photography and quickly turned that into a business as well. By mid-2016 I was shooting weddings and in 2017 I photographed 32 weddings on top of my already growing workload with website design. I still had a lot more freedom than I did when I had the shop, but I was getting busy again.

The housing market crash caused me to rely more on both of my businesses because people were not spending as much money as they were. I booked fewer weddings and businesses were holding on to their money to see how things played out. Thankfully I was diversified enough with my businesses and clients that I was able to stay self-employed. In 2008 I married the most amazing women I had ever met and I continued on my path to create more freedom from being locked down to my businesses.

In early 2008 I had started blogging on the topic of iPhone Apps. The iPhone had just received an update allowing support for third-party apps and my immediate thought was that it would soon be just as hard to find good apps in the Appstore as it is to find good music in iTunes. I turned out to be correct. Within a few months, I had a new business reviewing apps. I called it the DailyAppShow because I produced a video app review daily which was published to our podcasts, YouTube channel and a variety of other places. Back then there were a lot of sites trying to become what YouTube is today. Now I had three businesses I was running at one time.

In 2010, we had our first child and I decided it was time to get an office so I could keep work at work and be fully present when I was at home. My wife quit her job a few months before delivering our first child. For the next eight years, I would go from a small office to a large office and back down to a small office again. During that time I had ten different employees, five of which were employed at the same time. By this time I had transitioned from a freelance style business to an actual agency which I named Hill Media Group. I also had two more children. Things were getting complicated.

In July of 2018, my last employee quit to pursue different work and I found myself working all alone again. By this point, I had cut back quite a bit on the wedding photography and videography because I wanted to limit the amount of time I had to work on weekends. My kids were in school most of the week so the weekends needed to be for them. I was so busy during the week with other work that I had to start turning wedding clients away. In 2017 I photographed and filmed a small handful of weddings and in 2018 I took on none. Though I haven’t really kept this website up to date I am still receiving multiple inquiries for wedding photography each week. I still do a lot of photography work but it’s mostly commercial work that I do during the week which keeps my weekends free.

After emerging from the cloud of work that I found myself in after my last employee quit I sat in my office realizing that I had created exactly what I was trying to avoid which was a business that I felt tied down to. I also realized that my daily routine has become toxic. I felt the need to get out of the house immediately in the morning so that I could accomplish everything that I wanted to get done and be home by 5 PM. Though I was spending a full eight hours a day at the office I didn’t feel very productive. Once again I knew something needed to change.

I don’t need a physical office to conduct business so I made the decision to get rid of the office and set up a small home office. The problem with having a home office in our current home is that there is no room for that. My new office in our home is in our bedroom, which is a room only slightly larger than our bed. We had to get rid of our dresser to make room for my desk.

Now having far less overhead and the freedom of working from home, I have started looking into other ways I can cut back. I had a lot to get rid of by closing down my office. My 1400sqft office was pretty full. By moving into a small home office in our bedroom, I could only keep the essentials. Though I have downsized to my small office space I am still noticing items I rarely use that I could get rid of.

It is so easy to end up with more than we really need to operate on both in business and in our home. I often feel anxiety over all of the things we have and we don’t have as much as most in our community. It doesn’t happen overnight, it takes time to accumulate. Eventually, you need more storage and that leads to a larger house. It’s the American way and nobody will question your logic over it. We are great at justifying our actions.

On December 7th, we brought home an eleven-day-old baby girl we named Mikayla making us a family of six.

Early last month, we purchased a travel trailer and I started outfitting the trailer with new items. Amazon boxes were showing up daily. I wanted the trailer to be ready to go at any time. My logic seemed sound to me, but we already had enough stuff in the house to take from to outfit the trailer. I was once again accumulating more stuff.

Over the holidays, I started looking at what else I could get rid of. My wife went through her clothes so I did as well. I ended up getting rid of about 70% of my clothes which filled three garbage bags. I could get rid of about half of the remaining 30% and still have plenty of clothes. I have also started looking at other things I have that I have way too much of and plan to downsize even more. I am not downsizing to make room for more, I want small to be my new normal.

This summer we plan to travel in our trailer. The goal is to travel for two months while the kids are on summer break from school. Our trailer is a 28-foot town behind trailer which doesn’t have a ton of storage space. If we are going to spend as much as two months in this trailer, we are going to have to be very intentional about what we take with us. I am going to have to run my entire business from a backpack. My kids are only going to be able to take a few toys. We only have enough closer space for a few outfits. It’s going to stretch us quite a bit.

Two months of traveling in our trailer with limited stuff will be a reset for all of us. We will quickly learn what we can and can’t live without. By the time we return home, we will be used to less and my hope is that we can continue living a more minimalist lifestyle. I just want true intention for everything in our home. More does not bring happiness, it actually produces unrest.

My kids have a lot of toys. I have contributed to that as well as the rest of our family. When we travel, the kids are allowed to take a few toys with them and the rest stay at home. With less, they constantly play with their few toys. When at home, with all of their toys, they complain of being bored or not knowing what to do. I realized that in myself when I would get to my office and have a hard time figuring out where to start with my work. I had so much going on and so much stuff, it was overwhelming. It’s hard to decide what to do when you have so many options. You end up doing nothing.

We are getting excited about our road trip this summer. We will explore more than we ever have before and do more with less. As we move closer to our I will share more about how we are able to pull this off. Sharing our plans with others has generated a lot of questions such as:

  • How we are going to live as a family of six in a mid-sized travel trailer?
  • Where will we stay?
  • How will we wash our clothing?
  • How are you able to travel for two months of the year and run a business?

The concept of breaking free from the normal has never left my mind but I have taken some detours along the way. I could be a lot further along in my quest to be as free as possible, but we are here now and are working toward getting back to the freedom lifestyle I imagined having for myself and providing for my family. It will not be met without some resistance, but it is work we need to do. There is so much more out there and I need to experience it with my family. We have created a comfortable home and surrounded ourselves with things that make life more convenient, but that has not brought happiness.

If you are interested in following along as we make these changes in our life and travel as much as possible I would love to notify you of new updates when we post them. You can easily subscribe to our blog for free here.

What are your thoughts on living with less and creating more freedom in your life? I would love to hear your thoughts in the comments section below.

Here’s to Freedom and the Wandering Hills!

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