Name: Rachel Sklar
Age: 37
Location: New York, NY
Why we care: Rachel Sklar had her first byline in the New York Times before she gave up her job being a lawyer, the kind of savvy move that gets her a gold medal in career-changing. Today she's an editor-at-large for media-gossip site Mediaite, writing a book on Jewish culture, and we're sure her mother is kvelling.

You've been a lawyer and now you're a journalist, but what was your first job?
I'm not sure what the first one was. In Grade 10, I worked at Baskin-Robbins as an ice cream scooper. I got fired, officially because I took too much time off for the school play, but I think the boss was an anti-Semite. She said something really horrible that escapes me right now. I also worked at Shopper's Drug Mart, which is like a Canadian Duane Reade. I made minimum wage.

Why did you stop being a lawyer?
I was always creative, and I just wanted to write. When my first piece got published in the New York Times, someone at the firm left the page of the Times open on my desk. I closed the door to my office and just cheered. I liked being a lawyer, but it didn't hold a candle to doing something that I loved and was good at.

You took a pretty big pay hit.
It was brutal, obviously. I went from being a lawyer at a top New York firm to being a freelance writer with no contacts. After I'd quit, when I was very broke, I was invited to a wedding in Toronto with all of my friends. Everyone was bringing something to contribute and they knew I was struggling, so they just asked me to bring paper plates and cups for a get-together one night prior to the wedding. I spent like $40 on all this stuff — it was like 40% of my total net worth — and when I got to the party, a bridesmaid said, "Oh, thanks. But we already have this stuff." Not mean or anything, but she just tossed it in the trash. And I was horrified. The $40 I'd spent on it was so much money to me.

What'd you do to make it work?
Well, immediately after I quit, I had savings. After about a year-and-a-half, I moved out of my lawyer apartment. But I also had tons of stuff that I didn't need anymore, like business suits and other clothes, that I just sold off on Craig's List. I used to have people fill a bag full of clothes and charge them $50 for whatever they could fit in the bag. I actually met a bunch of cool people that way.

You're Canadian. What about the Canadian dollar?
It's awesome. When the exchange rate was really good and I was still a lawyer, I went home and picked up a lot of checks. I didn't know I'd be broke soon.

What's the deal with all the change? Carrying all that change around must be a hassle.
You mean the toonies and the loonies? I would guess that organized people have strategies to avoid coin overload situation.

You've got a book coming out about the culture of Judiaism. Any mention in there of Jews and money?
Nothing like that. I'm more focused on the filmmakers, writers, artists, journalists, musicians. To be honest, I haven't noticed a spending difference between Jews and other folks. Comedy? Yes. Food? Oh, yes. Money? Not so much. And it's certainly not apparent in my own spending habits.

Speaking of your spending habits, what do you spend money on?
My biggest splurge is cabs. I haven't had a non-essential spa treatment, like a facial, since 2004. My last haircut was my first in 8 months. But cabs make a real difference if you're walking around in high heels. With the subway, there's stairs to get down, then more stairs to get to the train. It's a foot killer. A cab takes you right to your door.

What on earth is a Charitini?
For my 36th birthday, instead of having my friends buy me a drink, I told them to donate what they would have spent on me to charity. I called it "Charitini," and now it's one of the projects that I'm working on, to encourage microgiving. Every charity that I check out, I wind up donating a little to.

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