No reason why a boy can't babysit.
I started babysitting at age 11 (I wonder now what the parents who hired me were thinking!?)... and kept it up until I was able to get my first "real job". My first real job was illegal, and I was paid less than minimum wage, and we were hired to sit in the boss' living room in the evenings, prepping roses for delivery to the convenience stores around town. So we'd have these big coolers full of long stemmed roses and we'd have to trim the stems, remove a lot of the leaves, and break off the thorns, then wrap them in cellophane. The single roses you'd see for sale at the counters at Stop & Go.
My fingers were like swiss cheese from the thorns! I had fun though because 2 of my friends worked for the guy but one of them was older and had a car and license, so he'd send us to Austin for deliveries on weekends and that was always fun.
Anyway, sorry to reminisce... most 14 year old's are going to be limited to babysitting, dog walking, mowing lawns, etc. I've seen some ads on Craigslist where someone wants to hire a teen helper to do work around the house but sometimes those ads give me a really creepy vibe.
My son was never able to mow lawns for money, except for my mom (who REALLY was cheap in paying him for having him do the 1/2 acre lot!!) because we have an electric mower..... he found that most people don't want to let you plug in your mower and then pay you to mow, so he nixed that one.
Meanwhile, I think kids can start volunteering at the Humane Society at 14 (without a parent present, but you should check their website to be sure), which would be good for a "resume" in a couple years, and good practice for learning to take direction in a work setting and having some responsibilities outside of the home.
It's actually fairly hard for a 16 year old to find places that will hire 16 year olds, from my son's experience. It was different when I was 16. Many places nowadays want you to be 18, minimum.