Jill Winger of The Prairie Homestead embraces failure

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When Jill Winger started blogging about life on her prairie homestead in Wyoming, she was just looking for ways to fill her days. Nearly a decade later, Winger has turned her homesteading lifestyle into a successful business and blog, The Prairie Homestead.

Jill Winger, blogger at The Prairie Homestead, with her family on their homestead in Wyoming. | Lindsay Linton Buk, Linton Productions

Everything looks picture perfect on The Prairie Homestead. Winger and her husband, Christian, have three beautiful children — ages 8, 6, and 3 — along with some chickens, goats, pigs, horses, milk cows and beef cattle on a 67-acres of picturesque prairie in southeastern Wyoming. In reality, the homesteading journey for this self-proclaimed “former city kid” has been far from perfect, but Winger’s willingness to embrace whatever challenges she confronts is part of what has made her so successful in accomplishing her self-sufficiency goals — and selling her brand.

Our Q&A with Winger reveals how she started homesteading, and how she makes the lifestyle work for her family. This is part of our Behind the Homestead Blog series on Hello Homestead, where we feature interesting homesteading bloggers and give an inside look into their lives.

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Hello Homestead: How did you get started homesteading?

Jill Winger: My husband, Christian, and I had just been married a little while. We were ready to buy our first house and we decided we wanted it to be out in the country.

We had just started working and had a small budget, so all we could afford was a ramshackle house on some land. It was what we wanted, but it was also depressing. I didn’t really know what homesteading was, but I was hit by this idea of making what we had pay for itself. That turned me on to the ways we could we do that.

This was about 10 years ago — we bought our property in 2008 — and homesteading wasn’t as big of a thing as it is now. It’s really been a movement, and I was able to grab on to the fringes of that movement and run with it.

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HH: Why Wyoming?

JW: My husband is from this part of Wyoming. I was here going to college and had just graduated. He had a job here, and the land was pretty affordable comparatively just start here and see what happens. It’s not a dream homestead climate which a lot of people don’t realize it’s a prairie so it’s flat, there are not a lot of trees harsh weather lots of wind.

HH: Did you grow up on a homestead?

JW: No, I was your typical ‘90s child. I grew up in a little house in town in Idaho. But from a young age, I was just obsessed with farm life. I kind of knew I wanted to get to the country as fast as I could, so I moved to Wyoming for college.

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HH: Why did you decide to start your blog, The Prairie Homestead?

JW: I started the blog in 2010. We had our first child at that point, and I was out in the middle of nowhere with no job. I needed an outlet, so I started the blog as a journal to keep track of my days.

Over time, it has turned into our bread and butter. We educate about the oils and help people learn how to use them, and as a result, have come to have a very large team over the years. It’s a legitimate business. We are independent distributors for doTERRA essential oils. It’s our main source of income. Christian works behind the scenes in that part of our business.

HH: What is the most profitable part of your brand?

JW: We sell ebooks, banner ads and other products, but our biggest revenue stream is our essential oils. A few years into blogging, I started talking about them just because I liked them. That got a lot of people interested. Now, we have a really large essential oils team, and we sell them through a company.

HH: What do you think is the key to your success?

JW: I am not afraid to fail and keep going, whether it’s homesteading, blogging or business. I have plans A through Z constantly. If one doesn’t work, I go to the next.

HH: Tell me about a time that you failed.

JW: One time, I poisoned my entire garden. I was so excited about this mulching method, but a potent herbicide that I had sprayed on our hay accidentally transferred to the crops and everything was wilting. Upon further research, I found that once the herbicide is in your area, it takes a few years to clear out completely.

But we didn’t stop gardening. We decided to try raised beds, and it ended up being a blessing in disguise. We had to figure out how to make them because we couldn’t use our existing plots. Since then, they have been popular on the blog, and they have worked really well for us. I wouldn’t have considered raised beds if we didn’t have the herbicide disaster to start with.

HH: One of The Prairie Homestead’s taglines is to help people “grow their homestead dreams, no matter where they may live.” Why do you think this is important?

JW: From day one of sharing our journey, I knew two things. I knew that I wanted other people to experience what we were experiencing because it was so empowering. I also knew that most people probably weren’t going to move to 67 acres in the country. If I wanted to share homesteading values, I needed to share it with people living in different locations. I think of homesteading as a state of mind, a mindset of ingenuity and self-sufficiency and creativity. Everyone can embrace that, even if you live in an apartment. You can master skills wherever you are.

Jill Winger, blogger at The Prairie Homestead, in her kitchen. | Lindsay Linton Buk, Linton Productions

HH: What do you think are the best skills for new homesteaders to start, no matter where they are?

JW: I recommend that everyone start in the kitchen. Even if you live in an apartment in New York City, you probably have access to a kitchen. There is so much you can do in a kitchen that is going to improve your diet, cut down your budget, and improve your ability to understand what you are eating. You can start working towards self-sufficiency with minimal materials.

HH: What is your favorite part of homesteading?

JW: I like having our kids be a part of it, and seeing them embrace that rural childhood. There are hard parts that come with that, like when animals die. It can be hard work walking them through that and helping them become well-rounded and balanced, but it’s been gratifying to be on that journey with them.

HH: What do your kids do to help around the homestead?

JW: They do chores in the morning in evening, like feeding the cats, taking care of the chickens and refilling water for the livestock. They are good at getting cows in if they get out. They are pretty handy to have around. They are 8, 6, and 3, so the 8-year-old leads the charge. We also homeschool them.

HH: How does homeschooling fit in to your lifestyle and brand?

JW: It’s a natural fit. I was homeschooled, so it was always in the back of my mind. I was always open to public school, but when we started this lifestyle, I got sad at the thought of sending them into town. Summer is kind of a free for all with projects.

HH: Do you think your kids’ experience will change as they get older?

JW: Hopefully, it gets easier for me a little bit as they have more responsibilities. I’m excited for the day that they can milk the cow. But when they get older, we probably will be going to town a little more for playdates. We’ll probably have to figure out a new balance of figure out homesteading projects with more trips into town.

HH: What is your philosophy for raising family on homestead?

JW: I really am a believer in the power of failure with kids. Letting kids experience disappointments and failures in a good, controlled environment is really a powerful teacher. The homesteading life is good at providing those opportunities. We make sure we don’t shield them from those life lessons.

That said, people email me wondering how to get kids to want to be outside, and I think all kids and families are different. For us, it’s been a process of showing them that work isn’t necessarily drudgery. We talk about the pleasure that comes with a job well done, and we make games out of it. We don’t want them leaving the lifestyle at 18 thinking, “Oh my gosh, all we did was work our whole childhood, and we hated it.” They still find joy in it. It’s a special experience.

HH: What are the greatest challenges of the homesteading lifestyle?

JW: We are trying to balance that old-fashioned style with one foot in our modern society. We’re not off grid, and we don’t have a desire to get off grid. We are still a modern family with cars and activities. There are some days when we need to go into town for an activity. We go to playdates, swimming lessons, gymnastics and meetings for our homeschool co-op; we also just started 4-H with our oldest. We do have to keep it more minimal than the average family because we do live far out and we have a lot of responsibilities at home.

The trick is to pick one thing and focus. I think that a lot people look at me and say, “How do you do so much?,” but there are a lot of things that we opt out of. We are pretty particular about what goes on our calendar.

HH: How do you find a balance between your old-fashioned and modern lifestyles?

JW: There is a definite paradox there sometimes. We are a high tech family with a blog, but also a milk cow. It’s tricky.

I really follow the idea of seasons. When it’s summer, we spend a lot of time outside and put blog projects on the backburner. During the winter, when the outside dormant, the blog is more active.

Even so, I think it’s ok to be old-fashioned on purpose, and to put that out into the world. We’re working on expanding that as much as possible.

This Q&A was edited for clarity and length from an interview with Jill Winger of The Prairie Homestead.

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