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Wayfaring Day 33 - House Sitting?

  • Writer: fleming386sfa
    fleming386sfa
  • Sep 17, 2025
  • 5 min read

August 2, 2025 Saturday


This was a Saturday for getting things at home base under control. Living this homeless lifestyle can create some issues with things like laundry or issues with vehicles. We bought BBQ for everyone for lunch and spent a little extra time with David´s parents.


Today we discussed the house sitting idea after looking at several websites and making the determination that TrustedHouseSitters.com is the best fit for us. It seems that many of the people on this site are somewhat similar to us. We had also had to deal with the issue of going out of town and leaving pets behind. We were always having to impose on friends and family and wished we could find another way to deal with this issue. Unfortunately we did not know of this site while we were in need as pet owners. The one thing I found with house sitting is that pets are the primary issue which means most of the need is for house/pet sitting. Many of those looking for sitters are retired or empty nesters who want to travel more but need their home, pets and plants taken care of while they are away. As ¨wayfarers¨ we happen to be perfectly positioned to be on the sitter side of the equation.


Keep in mind that we are looking for ways to travel as inexpensively as possible while realizing immersive experiences. We are pet lovers. We are flexible. We are conscientious. This seemed like the ideal situation for both the sitter and the person needing a sitter. In our discussions we felt the mentality of the sitter must be one of having the well being of the pet(s) and the care and security of the home as the top priorities. Then, within those parameters, the sitter has the opportunity to enjoy the local community in a deeper way than when you are simply on ¨vacation¨. Hopefully there would be some time for exploring the surrounding area and maybe get to visit some special sites that might be nearby. Our conclusions as to the mentality of the person who is looking for a sitter were based on how we would feel if we were leaving someone with our home and pets. Hosts, we believe, should interact with sitters more as friends than as paid help or employees.

Obviously their is an abundance of trust required on behalf of both parties with the host having to initiate that trust. The host bears the most trust since they are inviting someone they ¨presently do not know¨ into their home and allowing them to care for a family member or livestock in their absence. The sitter, once committed, has to trust that, after making sometimes extensive plans, the host will not back out and leave them with costs they may not be able to recoup. It seems to us that both host and sitter need to have a flexible and open minded approach to the arrangement and in a way to life in general. We allowed a close friend´s family who live out of the country to use our house for a week. There were multiple adults and children in the house but we were not at all concerned about them living in our house but were more concerned that they not have any problems while they were in town. It seems that hosts in this arrangement would be not only concerned for their home and pets while away, but would also have some concern for the well being of the sitter. In that same vein, we think the host has to realize this is not a job for the sitter but this is a give and take arrangement. Yes, the host is getting free sitting, but the host should realize they are providing a travel experience for the sitter as well. This is why we say ¨presently not know¨. In our mind this encounter should be more like getting to know new people and making friends than like hiring an employee.


We spent some time looking through the website listings to get a feel for how this would work. There were plenty of listings in areas where we were most interested in visiting. We really like places that are not as hot or maybe not as cold. Some of the areas that were of interest to us that were also areas with more opportunity were the west coast, Colorado, the northeast and the United Kingdom. As we read through the listings we were able to get an idea of what sort of situations we thought would be best fits for us and the host.


When looking at a listing you should probably read the general description first. Sometimes that is enough to help you decide to read more or move on. In our opinion, reading the Responsibilities is the next section to read. Reading the Responsibilities section will tell you a lot about the host. We are not saying that you read this to see if the sit is going to be too involved, but that may be a worthwhile consideration. What we think is that it reveals the mentality and attitude of the host. This allows you to see how you feel about the way you and the host are a good fit, or not a good fit. The responsibilities vary from people writing one or two sentences to several paragraphs. Now this is just how we look at it: We look to see how we think the host perceives the arrangement. Some hosts lead us to think that they do not see this as a give and take arrangement and seem to think you are an employee that they don´t have to pay. We look for people who make it clear that they understand this is an arrangement that benefits both parties. If we are satisfied with the Responsibilities we read the Home & Location section. This will further reveal the hosts desire for the sitter to not only take care of things but to also enjoy the stay. If they are concerned with how you enjoy your visit they will make mention of restaurants, grocery stores and other interesting places to visit. We read the Amenities last just to see if there is something we feel we can´t live with or without. Of course we look at the pets, but other than some of the livestock that is outside our wheelhouse, we are willing to sit for pretty much any pet or animal. Most of the sittings are for dogs and cats but there are some with different types of fowl, horses, sheep and others. If you are considering doing sitting you might not be as flexible as we are. For example, you might not like really large dogs or gerbils. Oh yeah, we don´t count snakes as animals for our purposes here!



 
 
 

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