How I Get Paid to Take the Best Writing Retreats Ever (With Puppies!)

In the months of April and May, I’ll be taking a total of six writing retreats, and I get paid for each one.

One had a jetted whirlpool tub. One had a fully stocked bar. The one I’m on as I write this is at a quaint country house on five acres of gorgeous tree-covered hills.

I don’t take advantage of most of the amenities (apart from the tranquil settings) because I’m deep in the process of researching and writing a book on chronic pain, and these times away from my normal distracting comforts are invaluable in forcing me to focus and bang out pages in a way I never could at home.

Some of these retreats are just overnight; some are a week or more. All of them include limitless pet, play and cuddle time with adorable dogs, which I have been yearning for since losing our home and our ability to own and foster dogs in the multiples.

How do I manage this, you ask?

I’m a dog sitter on Rover.


What I Love About Being a Rover Sitter

As a freelance writer, most of my work is paid for after the fact — I submit a blog post, invoice the client when it’s published (often weeks later), then get paid (a week to two after that, on average). Now that I’m working on a book on chronic pain, the next few months will largely be spent researching and drafting, but I won’t see my payment until after I submit the manuscript in July.

That means clearing my schedule to do a lot of work for basically no income in the present. Not the best model for a financially strapped couple living one income (mine).

Rover allows me get paid to type away (in addition to giving me my much-needed puppy fix). I bring my Chromebook to a client’s house, ask to tap into their wifi, and viola! I earn money while I work, which serves as an “advance” of sorts, buying me time to focus on my projects.

Check out just a few of my furry “clients”:


Rover - Toby





Sure beats staring at cubicle walls all day.


How It Works

I’ve been dogsitting since college, but word-of-mouth referrals only go so far. Rover allows me to tap into a whole networker of pet owners in my area and advertise why they should hire me to care for their furbabies. The sites does take 20% of my earnings, but it goes towards their 24/7 emergency support number, and I consider it a finder’s fee for connecting me with clients I may never have found otherwise.

My Rover calendar syncs with my personal Google calendar and lets people see at a glance which days I’m available. In addition to overnight stays in people’s houses, I also offer dog walking and half-hour drop-in visits to feed pets, let them out and generally give them some love. Rover also allows me to set rate levels for different services, including puppy care, multiple-dog care and cat care.

Clients (human) can contact me through the site or app, and Rover assigns each of us an anonymous number that forwards directly to our personal phones. The whole thing is extremely convenient and user-friendly, and thanks to the connections I’ve made in my first couple months with the site, I’m hoping to have a full roster of clients soon!


How You Can Become a Rover Sitter

If this sounds like something you’d be interested in doing, you can sign up here. You’ll need to pass a short exam on pet sitting basics (the questions are super-easy if you have any experience at all), and then you can create your profile.

I get paid to play with puppies. You can too -- join @RoverDotCom here: Click To Tweet

Your profile is your chance to tell potential clients why you should be the person they entrust with their pets, so be sure to mention what sets you apart — and include plenty of photos of you and pups to show your style. You can take a look at my profile here to see how I presented myself. (The main photo of me and my husband shows you the life I left behind when we lost our home and our dogs. I miss them so freakin’ much…)

There are plenty of helpful tips in the Rover Help Center for when you’re just getting started, and I also recommend applying to be a member of the & DogVacay Sitters Facebook group. It’s full of people who’ve been doing this for a while — some have even launched their own businesses as a result! — and it’s a great place to get feedback on tricky situations, pricing strategies and more.

What side gigs do you have to help support your passion? (If you don’t have any, now’s the perfect time to get started. What would you like to do?)

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  • Saja

    I tutor. But the prep time and business side takes up time and mind space away from writing. Keeping the kids all straight can feel like juggling knives.
    I’d rather dog sit!
    But I’m fueling a less than simple life. The dog-sitting might fit someone I know who needs a flexible job. What are the downsides?

  • I’ve been financing my various paid play efforts and the odd bill with the backing I get for the Paid to Play Podcast on Patreon. My biggest backer gets an hour plus of one on one brainstorming with me every month!