Hello from Chicago! New to the Site

I’m excited to get started on my journey. I absolutely love travel and exploring new places. I live just outside of Chicago in the western suburbs. I’m single, have two grown children, and work remotely. I have the perfect situation to travel freely throughout the US. I also hope to travel internationally with my vacation days.
I’d love any suggestions anyone has to offer or what I should expect.
Thank you!


Welcome! My family and I are currently sitting in Berwyn.

My best advice is to just start putting yourself out there for sits that align with your availability. Over time, you will perfect your profile and learn more about the types of sits you are or aren’t open to.

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Hello @MidlifeTraveler. Welcome to TrustedHouseitters and the community forum. One thing many new members do is put a link to their sitter page in their forum profile, so our members can take a look at it and suggest things that might fine tune it and improve your ability to get those important first sits.

Welcome! I’m new as well. It sounds like the hardest part is getting your first couple of sits, like your first couple of jobs. But this being the holidays, I think it’s a great time in favor of the sitter. I’d try to do a couple local sits this month and next; that’ll get you off to a great start.

Try to put yourself in the shoes of the HO and also other sitters. I didn’t realize that some sitters send almost(?) generic applications, whereas others send very detailed ones, making it clear they read the HO’s listing. I’m a detail-oriented person by default, so of course I read the whole listing—and waited a day to mull it over—but I may not necessarily convey that in an application, and that’s to my detriment. So just make it dirt-simple for the HO to understand that you read their listing, understand the pets you’ll be caring for, and will be a responsible sitter.

And be patient! I know some get lucky right away, and others have 10 rejections in a row. People here on the forums seem very helpful, like about constructive feedback on your profile, and I guess you could even provide sample application/cover letters and request feedback.