Personal Finance

Changing Your Life: From Contractor to the Farm

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Last updated on January 27, 2021 Comments: 14

This is a guest article by SimplyForties, a 48-year-old single mother of a college-aged son, who is navigating her way through midlife and documenting it.

Like a lot of people, I lost my job in the summer of 2009. I had a very lucrative position as an off-site paralegal for a retired Coast Guard commander who worked as a liability expert in cases of marine casualty. He felt I was invaluable to him and he was willing to pay me a good deal of money to always be at the top of my client list. To top up my coffers even more, I had a few contracts providing technical network support to local small businesses. I was making a lot of money but I was also working a lot of hours.

When the bottom fell out of the economy, insurance companies were choosing to settle instead of going to court, and the bottom fell out of the liability business too. I lived in a very small town in west Texas and when my primary client had to regretfully let me go, there was little chance I could pick up enough business elsewhere to bridge the gap. I had a mortgage payment, a son in college and some decisions to make.

I had for a long time been yearning for a different sort of life, and this seemed like a good time to make a drastic change. I began to think about where I would choose to be if I could be anywhere. What I came up with was a little cabin, a few chickens and a garden; in other words, a much simpler, less expensive lifestyle. I put that out there and things started to get a little weird!

I stumbled across an article on a blog I’d never seen before. The article was about a small farm in southwestern Virginia the author had purchased. He was unable to occupy the farm right away, so he was looking for a caretaker. On a whim, I sent him a response. He received dozens of applications but, after discovering and reading my blog and realizing we were on the same path, he offered me the position.

I put my house on the market and made arrangements to sell the bulk of my possessions. In spite of the soft market, I was able to sell my house in three days for above my asking price. Within a month of having read that blog post, I was on the farm, living a very different life!

When I first came to the farm I was expecting to be here for a year. After six months, the farm owners suffered a change of circumstance and let me know that they would be moving to the farm on April 1, several months premature. I decided house-sitting might be just the gig for me so I signed up with a service and starting looking for another position.

Things are going pretty well. My next stop will be just outside Knoxville, Tennessee, where I will be house-sitting for some RVers who are setting off on a six-month trip around the country. In October I will be looking after a home in Houston for some clients who spend the better part of the year in France. That gig will take me through June of 2011 by which time I will have been house-sitting full-time for nearly two years.

Although my income and my social circle has greatly decreased, I have been able to keep working and keep in touch with those of my friends who mean the most to me, thanks to technology. I’ve learned a lot about myself since starting this adventure. I am confident that I will be fine wherever I go, that I will be up to the challenges that face me.

I miss having friends I can call to meet for lunch or catch a movie or go for a drink but there are nice, friendly people everywhere, and I’m learning to reach out a little more. I’ve learned that I value free time more than money. I used to dream of a windfall solving my problems. Now my needs are few and all I really care about is being able to pay my very few bills and hopefully put a little away. The main thing I’ve learned is to stop pushing and allow life to happen.

How does anything get done if you stop pushing? It’s not about doing nothing, it’s about deciding where to put your energies. I’m no longer striving for a better job, bigger house, newer car or a bigger bank account. I’m striving to be a better person. That’s hard work. I figure if I can get that one down, the rest will take care of itself!

I don’t know what is going to happen next but I know that it will be the right thing and I’m facing it with a feeling of happy anticipation!

Article comments

Anonymous says:

Wow…let’s re-emphasize…DRASTIC change. You are crazy lol (in a good way?)

Anonymous says:

lol, a lot of my friends would second that opinion!

Anonymous says:

When I read the title of this post, I thought it was going to be about pursuing farming as a lifestyle as an alternative to cubicle-dwelling urban life. Shame it wasn’t, as that’s the precise transition I’m most interested in reading about, and kind of what I’m going through right now.

A lot of blogs about alternative lifestyles all come back to variations of “I’ve learned that I value free time more than money.” I’m not going to say I value money over free-time, but I do feel that many people over-value free time. There’s a limit to how much free time you can have before you start craving something to do. Even going out to lunch with friends gets old after doing it 3-4 times per week for months on end. I know, that’s pretty much were I just was until this month.

Anonymous says:

lol, sorry to disappoint you! Free time for me doesn’t mean sitting around doing nothing, it means I get to choose how I spend my time instead of how my boss chooses or how my bills dictate. I was pretty busy all day long on the farm. If you’re looking for a transition to farming you should check out the farm owner’s blog at because that’s exactly what he and his wife will be doing as of April 1!

Anonymous says:

Thanks for the link to the blog. I will check it out.

I didn’t sit around doing nothing either. During my unemployment, I spent at least 3 hours each day job searching, I did all the cooking and cleaning, I volunteered, I met with other unemployed friends for lunch. But I still had 60+ free, waking hours each week with nothing to do. I’m glad to have a job because now I’ve got something to keep me busy.

Anonymous says:

Thanks! Generally speaking you don’t get paid. Depending upon the situation you might have to pay utilities and you might have a few chores to take care of. It should be a mutually beneficial arrangement with you taking care of the property and having enough free time to work in exchange for living in the house for free. Being a telecommuter is the perfect arrangement for a housesitter!

Anonymous says:

Wow! What a great story! So, do they pay you or do you just get the privilege of not paying rent?