The woman who dog-sits on Rover to support her passion for travel blogging

Life in the Gig Economy tells the stories of workers in an industry millions of people rely upon. If you’d like to share your story, email staff writer Jessica Bursztynsky at Jessicabursz@proton.me.

Christy Woodrow is a 44-year-old travel blogger and gig worker based in San Diego. This is what the experience has been like, in Christy’s own words. 

I grew up with a dad who has always owned his own business. I was born seeing that, which I really appreciate. Throughout my life, I’ve just been like, “I can’t really see myself working for someone else.” I worked for him for about five years. And I was doing a lot of bookkeeping, office management, because it’s something that I’m really good at. And then from there, I started working as an independent contractor and had different bookkeeping gigs and stuff, which paid the bills.

In school, I did some photography. I was always really interested in that and then writing, and so I just always thought that was going to be, like, my hobby. I built a travel blog just for fun and it was before blogging was really a thing, and so I wasn’t making any money. Then it just became my career, and I feel really lucky that I was able to do something that I love and be able to be creative. Of course the industry has changed a lot. Instagram came along, and AI and all sorts of things. I feel like I’ve gained so many different skills, and so then it leads really well to gig work. Partially I see opportunities where I’m like, hey a friend needs website work. I love the design aspect of that. I’ve kind of just done it on the side. But then with COVID, it’s become more of a necessity. 

The website work is becoming more of a main focus for me. So web design, helping businesses build their brand. I do house-sitting. That’s more of a recent thing. I do Rover and referrals, so house-sitting and dog-sitting. It works well, because I work remotely. But I’m kind of picky, where it needs to be a place where I can get work done. [Sitting] has been a couple times a month lately, but it’s more repeat business. And then I do catering, which is more of a referral thing. 

Last year, I was like, “Maybe I’ll look for another job.” It’s kind of exhausting to always be wondering where my next thing’s going to come from and my business being so up and down. Maybe it would be less stress. I applied for some jobs, but I’m very picky—I want remote work, and so does everybody else. So I honestly can’t see myself going back to that.

I started contributing to retirement when I was, like, 21. I didn’t do it every year. There were many years that I didn’t. But I just basically contribute to my own. When my business was doing well, I just did the max. I don’t have anyone, obviously, matching it. And I do wish that I would have stayed on top of it when I first started it and just done it every year. And health insurance is very expensive. So, that was also another thing where I was like, “Ooh, working for somebody else, I could have health insurance.” I guess that’s why I have to keep hustling.

This conversation has been edited and condensed for clarity.

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