I’m broke. And, like a lot of people in New York, one reason I'm broke is because I sink a lot of money into my iPhone. So when I heard about the recently launched and revamped Gigwalk, the app that lets you make extra money by using your iPhone to find odd jobs that businesses need doing, I jumped at the chance to be a guinea pig. Basically, you open the app, tap the red dots around you on the map and do a small job for a few dollars. There are tons of these red dots all over the city, and most consist of just taking photos. Submitted gigs earn you “streetcred," or Gigwalk karma points. The more streetcred you have, the more those map dots pay. The app keeps track of what you earned, and you collect the money through PayPal. It sounded easy enough, so I set out to see if you could make enough on Gigwalk to have a solid supplement to a too-small paycheck.

Gig #1: Captain Café, Murray Hill
During my lunch break, I clicked on a red dot near my office building to pick up a quick gig. The map told me to head to Tony’s Burger to take photos, but the address listed was occupied by Captain Café. If a business is closed, Gigwalk only pays out $2; you just have to snap a couple photos to prove the business is closed. There were no instructions about what to do if there’s another business in the very same spot, but I figured if I went through with the whole assignment, I could get the full $4.

One secret of Gigwalk: when you first get started as a “Gigwalker," you have zero streetcred so nearly all the assignments open to you will be for Bing Maps. Each assignment required five photos: an exterior shot taken from across the street, an exterior taken from the same-side sidewalk, an interior "panorama" shot, and then two close-ups of items snapped in the panorama. Taking photos of the outside of the building was easy. As I fiddled with the app before taking my next steps, the hirsute proprietor came outside for a cigarette break and said, “You take lots of photos of my business.” I muttered an answer and tried to look busy. I felt awkward and kept giving one-word answers. Then came the hard part: I had to go inside and take the panorama shot using Microsoft’s Photosynth app.

As I stood in the middle of the room, rotating around with my camera, the owner shooed me away. “The customers, they don’t like to have their picture taken. Come back later when it’s not so busy.” I went back a few hours later. The owner was still there, and he asked what this was for. I tried to explain that I was a writer working for Bing, which is like Google but not. The cashier, who appeared to be his daughter, tried to translate for me but she was just as confused as he was. “You make money doing this?” Um, sort of? “Write something nice,” he said as I hurried out of the shop.

Time spent: 30 minutes
Amount earned (if accepted): $4

Gig #2: Bagel Café Ray’s Pizza, East Village
The East Village is chock-full of nutjobs, so no one will notice me snapping photos, right? After I got the façade shots out of the way, I spent $2 on a Snapple so it wouldn’t look odd that I was hanging around there. I went in and did the panorama shot as quickly as I could; but, of course, I screwed up because I was rushing. Retakes. Awesome. Walking by, one pizza guy said, “You recording, huh?”—but otherwise I was left alone. My hands got a little shaky when I did the close-up shots of baked ziti and the refrigerator but it was over and I submitted it.

Time spent: 20 minutes
Amount earned (if accepted): $4 (minus $2 for Snapple camouflage); +3 streetcred

Gig #3: Starbucks, Union Square
I thought this one would be easy—after all, lots of people visit Starbucks just to use the bathrooms, so I didn't expect to look conspicuous being there without buying anything. (Although, I had to wonder: Who the hell uses Bing to see what a Starbucks looks like inside?) I’d had a bad day but marched across Broadway, phone held high, confident a completed gig would boost my mood. But while taking the panorama shot, two people at table behind me kept stopping their conversation to giggle and stare at me. I tried to hide behind a girl with an iPad but they kept staring and soon other people were staring too. I abandoned the gig and ate a cupcake at home.

Time spent: 10 minutes
Amount earned: $0

Gig #4: Pret A Manger, Murray Hill
I have a friend at Pret A Manger. Or rather, there’s a guy there who gives me free cookies sometimes. I can’t tell if it’s because he thinks I’m cute or because he feels sorry that, like clockwork, I buy a chocolate-chip cookie every day at 4 and pay for it with a debit card. Either way, I thought I could nip some of Gigwalk’s accursed awkwardness in the bud by telling him upfront, “Hey, I’m not crazy, I'm getting paid to do this," and going in during a slow time. I took the damn panorama and the required close-up shots, but got stuck when it came time to take a picture of the shop across the street. Park Avenue is very wide so the shot wouldn’t be clear without zooming in and Gigwalk does not like zooming in. I wasn’t about to risk my life standing on the tiny sliver of an island. I punched in the bit about the island and submitted it.

Time spent: 15 minutes
Amount earned (if accepted): $4

Conclusion: It might just be that the "entry-level" Gigwalker jobs are the least fun to do, but I found completing the gigs to be embarrassing and impractical: try as I might, I couldn't find a way to get the required shots without getting in people's way with my iPhone. Once you earn "streetcred," the jobs might get better—but the app doesn't tell you how many more points you'll need to reach the next level. After a couple days, I found the work for the first two gigs had been rejected, meaning of the three completed assignments, I only earned $4 for one of them. At least “Sam" was nice enough to leave a comment in the feedback section of my account: “Some tips to prevent issues in the future are to dress well and make an appointment to photograph a difficult business.” For $4? No, thank you. I’ll stick to odd jobs on Craigslist.

Time spent: 1 hour, 15 minutes
Total earned: $4 – $2 Snapple = $2

Desiree Browne is the weirdo behind the vintage fashion and pop culture blog Pop-o-matic Deluxe!. She likes dancing salsa, decade theme parties, and Hello Kitty in a completely not ironic way.