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Passionate experience junkie. Lover of the arts and architecture. Want to see and share the world, one village at a time.

One Guaranteed Tip to Win the House Sitting Assignments You Want

Remote house sitting in ItalyMy goal here at HouseSittingTravel.com is empowering people to succeed at house sitting.

To that end, I have written blogs about aspects of the whole process, such as creating a really fantastic profile and understanding the language of house sitting.

What I want to talk about this time is the one sure-fire way to catch the attention of a homeowner. I have written about this in THE HOUSE SITTING BOOK, (no longer available — contact me if interested), but two recent happenings cemented home – once again – just how important this one little tip is.

The first time you reach out to a homeowner, appealing to them why you are the perfect candidate for the job, your letter may be among one hundred or more similarly-worded appeals. All the potential house sitters tell stories about their high level of responsibility, experience taking care of homes and pets, and how they love house sitting and meeting great folks around the world. They leave laudatory references that would impress even the most skeptical of homeowners.

So how can you set yourself apart from all those qualified, wonderful, experienced house sitters?

House Sitting in Denmark

Conrad and I house sat in Denmark with Erin and Georgia


I had not one, but two great situations lately that made my heart so happy. Here’s what happened:

  1. Linda, a woman who read my book, emailed me that she landed her first house sitting assignment by using my one tip.
  2. A homeowner who I recently contacted to win a short house sitting assignment in New York City told me she picked me because I was the only person that made a comment about the photos of her dog.

That’s the tip: Simply mention something personal about their photos.

Here’s what Linda told me she did to land an assignment:

She made comments about the homeowner’s photos and asked a question about the pets. It started an email conversation between Linda and the homeowner, establishing a connection. Here’s an excerpt of her letter to the homeowner:


It looks like you like to travel as much as we do with all the wonderful photos on your wall. I noticed a photo of Venice and we’ll be there next month as well. Your house is charming and has a cozy cottage feel to it. We are also looking forward to taking care of your cats. Are they any specific breed?


It really couldn’t be any simpler. Besides giving her qualifications, Linda took the time to speak directly to their photos and words.

And in the situation where I won an assignment:

I was the only house sitter that mentioned the homeowner’s precious dog in my opening letter to her. And, you know, to her, the dog is the biggest and most important reason for hiring house sitters. I was shocked to be the only applicant to specifically mention her dog, but it proved to me that this is the one thing to set you apart from the pack. So easy – just talk about their pets. (Or something else in their photos or words.)

House sitting in U.S.

I won an assignment at this home in Baltimore, Maryland because I said how much I loved this little backyard fountain and could picture myself there on a warm, sunny afternoon.

Moral of the story: Turn your attention to the homeowner. When 
you write that first letter of introduction, pick out something 
that speaks to you either in their photos or their words. This 
has to be genuine. The more genuine you are, the quicker the 
sentiment gets right to the homeowner’s heart.
What I said to the homeowner about her dog was that he looked so 
cute digging in the sand and my only regret was that we would be 
house sitting in winter and couldn’t take him to the beach and 
watch him doing that in person. That’s sappy, but it’s what I really 
felt when I saw the picture, and it touched the homeowner enough 
for her to award me the assignment.  

They say a picture tells a thousand words. What are the homeowner’s 
photos telling you? Get in close and pick out little details. Be 
genuine and be simple.
What do you think of when you look at their home? Do you long to be 
in that setting? Are the landscape plantings similar to ones you have? 
Does a porch look inviting for a nap?
What about pictures of their pets? Do they look like rascals? Have you 
had the same breed before or like that particular breed? Is their photo 
caught at a perfect moment?
All people want is to know you pay attention and care about connecting 
with them. Your observations make them feel closer to you.  And it works.
Then of course you can go on to give your shining qualifications, which 
may or may not be different from the dozens of other applicants. 
What really sets you apart are your comments about their specific photos and words. 

I wish you happy and safe travels always and all ways.

I love to offer tips on house sitting. Click here for a menu page of more tip-related articles.


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6 Responses to “One Guaranteed Tip to Win the House Sitting Assignments You Want”

  1. I’ve been selected many times by using these tips in a genuine way of course and had pet/home owners comment that many applicants never even mention the pets.

    I’ve even been known to write directly to the pets …. and then got to meet them!

    March 4, 2014 at 12:18 pm Reply
    • Hi Angela,
      What a super idea — to write directly to the pets! So cute. And thanks for proving my point — this tip works!
      I so appreciate you stopping by to comment.
      Happy house sitting,

      March 4, 2014 at 12:27 pm Reply
  2. This is such a little jewel of wisdom and worth so much value, Josie. If I’m a smart chick like you, and I think I am, I’m using that now..so much Aloha. 🙂

    January 24, 2015 at 9:46 pm Reply
    • Welcome, Robin! — and thanks for your kind words.

      January 25, 2015 at 9:13 am Reply
  3. Josie, that’s a great tip. We’ve done a couple of housesits, but haven’t made the cut on many more we’d have liked to have done. Next time…
    Tom Bartel recently posted..Tomb of Jesus, Church of the Holy Sepulchre, JerusalemMy Profile

    January 25, 2015 at 10:03 am Reply
    • Thanks Tom! I’ll be waiting to hear about many more successful house sits . . .

      January 25, 2015 at 10:45 am Reply

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