Second Shift: Turning chores into cash

James Cleveland is happy to have other people pawn their chores off on him…for a price.
Credit: Provided

We all know living in the city is expensive. So how do people do it? Our series, Second Shift, features people working more than one job to make it work. This week, meet James, who has a full-time job and is also a TaskRabbit for extra money. Want to be featured? Email

Name: James Cleveland
Age: 26
Residency: Riverdale, New York City
Lives: Alone
Number of jobs: 3

What’s your primary job?

I work as an office assistant in Midtown Manhattan. It’s a Monday through Friday, 9 to 5 job. I file, do reception work, computer work, run errands. … I wear a lot of different hats.

What do you do on the side for extra money?

I’m a TaskRabbit. Basically, TaskRabbit is a website where you can find different [jobs] you can do. Some are one-off jobs and some are reoccurring. There are so many different things on there, but they are jobs like making deliveries, events and packing items.

Do you ever see any really weird ones? 

Yeah. Last year, I was hired to be a hype man at a party. I went to a rooftop party, they gave me some beer to drink and I had to get everyone riled up. I got paid $100 and then got a $60 tip.

Was there ever one that you did that wasn’t worth the money?

I don’t really like doing cleaning tasks because people are very particular about how things should be cleaned. You might think it’s clean, but they’ll think you missed a spot and it becomes very tricky. I only do cleaning tasks if I really need the money.

What is the third job you work?

I just joined WunWun, which is a delivery service, mostly for people in Manhattan and Brooklyn. I get a text about what needs to be delivered and I just go buy the items and deliver it to the customers. It’s for places that don’t normally deliver, like Target. 

Do you rely on your TaskRabbit and WunWun money to make ends meet or is it more “fun money”?

It’s more “fun money.” My primary job is my make-ends-meet money, which pays my rent, bills and so forth. The TaskRabbit and WunWun money is just money in my pocket. But I haven’t really hung out with my friends since New Year’s Day. I’m always working. Every time I see an opportunity, I grab it. I’m very independent. Ever since I was 13, I’ve worked for everything I’ve wanted. My mother taught me that you have to work for things you want; people don’t just give them to you.

Do you find it hard to date since you work so much?

It’s not really an issue to me. I’m a pretty easy going guy, so if I meet someone and there’s a good connection, I keep in contact with them. I meet different people. I’ve met other TaskRabbits and we’ve become friends and hung out. It’s more about your personality and just knowing how to project yourself and then everything just kind of falls into place.

Follow Emily on Twitter: @EmLaurence



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