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How to Make Your First House Sitting Message Win

written by Sam and Veren April 7, 2018
How to Make Your First House Sitting Message Win

So you’ve signed up for a house sitting website and found a sit you’re interested in. Now it’s time to write that winning first house sitting message that will get you noticed by home and pet owners!

And if you somehow ended up here without prior knowledge of house sitting, first you should dispel any myths about house sitting, and if you decide it’s for you, start here at our post: How to Start House Sitting. Once you´ve made an account (we recommend TrustedHousesitters) and fleshed out your profile, it’s time to start applying!

While this is written from the perspective of house sitters, homeowners take note: your sitter’s first message should incorporate these aspects. For more tips on choosing a sitter, head to our article: 5 Steps to Using a House Sitter for the First Time

We want to dispel the myth that housesitting is a free vacation for sitters. If you really want to housesit, you should take it seriously, much like a job. We definitely do and we’ve landed over 16 house sits since we started.

With that in mind, what are practical steps you can take in your first house sitting message to homeowners? 

  1. Carefully read (not skim, actually read) the homeowner’s post

This is your chance to glean for details, to show that you’re paying attention and that you have the homeowner’s needs in mind.

Do they mention that they’re concerned about a sitter being able to properly administer the pet’s medication? Is the pet still young and jumping around with boundless energy? Do they need three walks a day or just a minimum total amount of time?

There’s an endless amount of things that homeowners could care about. Most homeowners will say exactly what matters to them in their post.

Once we pointed out that we had experience with hounds and their incessant need to sniff everything. Ultimately, this got us a sit in Manhattan, a very competitive area for house sitting. When we asked why she had chosen us, she immediately said, “Well, you’re the only one that mentioned knowing my dog’s breed personality, and that means a lot to me.”

You don’t have to address everything that the homeowner mentions, but throwing in a few details shows that you’re on the ball. If the homeowner mentioned that their pet needs medication, talk about your experience with administering pet medication or your willingness to learn. If they seem concerned about their dog getting enough exercise, talk about how much you like to take walks, runs, hikes, whatever (and if you don’t like these things, consider whether you want to house sit for an energetic dog).

  1. Focus on the Homeowner’s needs in your Message

Sam and I are avid fans of all things Japanese. We love their food and we watch anime regularly. I particularly love manga and films about feudal Japan. While we do talk about challenging travel norms, and prefer to travel alternatively, we will totally admit we have certain dream destinations, like Japan.

While it’s nice that we feel that way, the day we find a sit in Japan, the message to the homeowner will not be “omg we loooove Japan and that’s why you should choose us.” Loving Japan does not make us good house sitters.

We’re amazed at how often we hear that homeowners received responses that only talked about the sitter and how well the sit would work for them.

This isn’t to say that you can’t talk about how excited you’d be to visit the place where the homeowner lives. People love when you’re interested in their town or city. But leave it towards the end, and focus on what you have to offer the homeowner first. We’ve done this many times and find it’s nice to sign off by including a bit about why we want to visit their region in particular.

Also, we’re not saying that you shouldn’t have your needs met as well. We say it in all our house sitting posts – house sitting should be about a fair exchange. We’re assuming that if you’re applying to a house sit, you’ve already decided that this is a situation you’re interested in learning more about.

If you get to the “interview” or Skyping stage, be sure to ask questions about your needs as well. If you learn things when talking with the homeowner that make you reconsider if you want to do it, don’t be afraid to politely decline. Read our post How to Avoid Bad Housesits for tips on what we do to make sure it’s a fair situation.

Mainly, our point here is this – you don’t want to come off as a high-maintenance house sitter.

Check out this blog post from the perspective of a homeowner about the applications she receives from house sitters for more insight.

Cinnamon dog in snow

  1. Structuring Your First House Sitting Message

Usually, we start off with a line or two introducing ourselves. We say that we’re interested in house sitting for them and share a quick tidbit about us, such as where we currently are.

Then we get into the nitty-gritty – our experience house sitting. This part is where we really tailor each message. We mention a line or two about our experience with the type of pet (we have dog, cat, bird, small pet experience) as well as address any specific concerns that the pet owner has talked about in their posting. This will really help you stand out from the crowd, because believe it or not, most people don’t do this.

Finally, we end with a suggestion for a video chat for further discussion. We strongly feel that video chats are essential for getting both parties needs discussed and establishing a relationship. You can tell way more in a face to face conversation than in messaging. We personally would not housesit for someone who did not want to have a direct conversation to discuss things.

  1. The Perfect Length

Incorporate all of these tips in a message that is short and sweet. We find that a 3 paragraph message works well (4 if there is more to say, like if there is a particular connection). You don’t want to overwhelm them with an essay detailing all your experience – that’s what your profile is for. You also don’t want to make it too short that there’s nothing to interest them.

If all you say is “I’m interested in house sitting for you, please see my profile,” they very well might pass onto someone who has taken the time to send out a well-thought-out message. It shows that you’re willing to go the extra mile, which will translate into how you will care for their pets.

And finally…

  1. It’s a job – treat it like a one.

We have always approached house sitting with this mindset. With 16 plus house sits via TrustedHousesitters, we might be onto something.

Our society values work ethic and professionalism. People won’t take you seriously unless you know how to conduct yourself in a professional manner within a workspace.

We are well aware that house sitting is quite an unconventional scene, and tends to attract people of alternative lifestyles.

Yet, that doesn’t mean you can slack on your applications and obligations. Whether we are currently rebelling against the norms or not, we will all judge someone’s merit on how well they can present and pitch themselves for the job.

Also, consider: how often are you the only one applying for a job? Pretty much never.

In house sitting there are several, even dozens of people messaging the homeowner for the same sit. All it takes is one lazy message, or lack of detail, or just plain old boredom, for the house owner to stop reading and never look back again.

Think of your first message like a short house sitter cover letter, where you want to grab their attention and get them to look at your profile, which is like your résumé.

Writing an application message might seem intimidating and like a lot of work at first, but if you really want to housesit, having a winning message is key.

And practice makes perfect.

Dog walking in Jackson Heights

Top Tips for New House Sitters: How to Make Your First House Sitting Message Stand Out: Most people neglect these things when messaging pet and home owners, so if you do these five things you'll stand out from the crowd! Click to learn more and start house sitting! #Housesitting #BudgetTravel #LongTermTravel

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