Rachel Sklar likes to shake things up, making major moves across countries, careers and platforms while making it all look incredibly easy. The 32-year-old Toronto native left her high-powered corporate attorney position, which saw her working in New York and Stockholm, to become a journalist five years ago. For the last three years, she’s been a full-time freelancer for publications such as Glamour, The Financial Times, The Chicago Tribune, Wallpaper, and The New York Post. In April of this year, she took the helm as co-editor of Mediabistro’s FishbowlNY, a media gossip blog covering the ins and outs of newspapers and magazines big and small. While Sklar shares editorial duties with Mediabistro’s editor-in-chief Elizabeth Spiers (with the help of Contributing Writer Christian Moerk and a recently acquired team of Fishterns), the bulk of the media-intense posts come from the witty, offbeat Sklar, who’ll blog about serious news stories about media figures such as Judy Miller and Peter Jennings as well as lighter fare. Sklar proved her ability to move quickly as she answered Gothamist’s last minute questions, telling all about her media learning curve, making a lateral career move, breaking into The New York Times, and her alter ego as an actress and singer. Be sure to catch her combining her love for media and song tomorrow night in media musical Weekly Review at Gotham City Improv.

You came from a history of print journalism to become co-editor and main writer for Mediabistro's FishbowlNY. Did you apply for the job or were you approached to do it, and how does it differ from your initial expectations? What's surprised you the most about the demands of blogging?
The opportunity to do Fishbowl came totally out of the blue. I was actually recommended by AJ Daulerio, one of the editors at the Black Table and now the resident sinner at Oddjack. I had done a few Black List/Waxing Off entries and had helped out with the BT's Republican National Convention coverage, most notably a party crash of an RNC event where I witnessed a Republican Conga Line. In November when Elizabeth was looking to launch the six MB blogs she needed someone for the service blog–which became mbToolBox, blogged by the incomparable Claire Zulkey. I just didn't consider myself qualified to offer advice at that time, and plus I was a bit bummed that the gossip blog slot was taken. We parted ways and that, I thought, was that. Out of the blue in mid-March I got an email from her asking if I was still interested. I was. Scared witless but yes, very interested.

I don't even know if I had initial expectations–there honestly wasn't time. The learning curve was incredibly steep, and I was paranoid about making mistakes so I was following every link on every story, and deeplinking everything (I think that's a word, am I using it right?). But it was so much fun and such a total rush–and it felt really familiar too, like the elaborate goofy emails I used to send to my friends during all-nighters at the law firm. It reminded me of–geek alert–doing my law school humor magazine ("The Hearsay", breaking the Orientation Committee daytimer scandal wide open) and "The Winnebugler" at my summer camp (Camp Winnebagoe, which astute readers of Fishbowl will recognize). Choosing the images, writing goofy headlines, using links to create gags–it sounds dorky but it was just so much fun.

What's surprised me most about the demands of blogging–the relentlessness of it. 24-hour news cycle, every media imaginable right here in New York, totally fair game. Something is ALWAYS happening, and you are never covering everything. I won't mention law school again but it reminded me of exams right from the getgo–sandwiches on the go, sixpacks of Diet Coke crumpled at your feet, papers everywhere, and the adrenaline rush pretty much the whole time. I rarely forget to eat but at the beginning blogging had me forget-to-eat busy.

FishbowlNY's tagline is "Because you can't shoot spitballs at the media elite if you don't know who
they are!" Did you know about the people you're now covering before you started the job, and how much reading/preparation have you had to do to get up to speed?

I knew laughably little. See aformentioned fear, paranoia. I knew the standard-issue Gawker targets–I had been an early adopter in the Elizabethan Era, and Graydon Carter is Canadian after all–but the Kit Seelyes, Tom Scoccas, Keith Kellys, Jack Schafers and David Carrs of the world really weren't on my radar (though Radar actually was). Luckily, my boyfriend at the time worked at a magazine and just knew the industry inside and out. He was a total mentor and gave me an amazing media crash-course. Plus Elizabeth is a one-woman historian of the New York media scene, and in addition to all that I was reading like a fiend. I learned quickly.

Because the media world is so small and interconnected, has that ever presented a conflict of
interest problem for you, and if so, how have you dealt with that?

It hasn't happened that often but yes, there have been a few conflicts. Nothing major. Of course the shrieking desire for the scoop can get really strong, but so is the desire to safeguard connections and keep everone happy. I started as kind of an outsider - freelancer working from home, building contacts from the ground up etc.-so I didn't have too many relationships holding me back. But you're right, it is a small and interconnected world-which, by the way, I think is a good thing becauase it keeps information flowing-so conflicts are going to be unavoidable-but we're all professionals, if you're careful it's not hard to navigate. I'm always aware that I live in a glass house surrounded by giant stones, and I try to be even-handed. Though my dad thinks I'm tough on Bill O'Reilly.

What was the adjustment period in becoming a first-time blogger like? What kind of a learning curve has there been and do you feel like you've finally settled into the job?
I talk about that a bit above, but yeah, the adjustment was huge. The ADD of seventeen different windows open on your computer with the TV on in the background, forgetting to eat, ridiculous amounts of Diet Coke (my worst habit). Plus I had no idea what I was doing technically–for the first month in order to link to old Fishbowl posts I'd click on the "email me" link and then copy and paste that. I had no idea about right-clicking on the date or time. It was also a very exciting day when I learned how to use bullet points–SAC (FBNY's Sacramento Correspondent) had emailed me a post with bullets, and I copied and pasted my way to a whole new level of blogging.

I do feel like I've settled into it now. I kind of miss forgetting to eat though. It was cheaper.

What Fishbowl stories so far have been your favorites?
Yowsers. Okay, well, probably the most obsessive thing I've done has been the "We Didn't Start The Fire" post, where I rewrote the song to reflect the big news stories of the day, with a link for every one. That took a long, long, long time but was really satisfying (I also liked writing my Eater song, and was deadly serious about Per Se).

I was pretty proud of my Bright Eyes get at Coachella-poor Conor Oberst, he never had a chance. I've really enjoyed being engaged by the issues involved with the Deep Throat, Newsweek/Koran and PlameGate stories. They're all linked, of course. I find it all fascinating. Others dear to my heart: Google goes all googly; Ellie and the big scary spider; the saga of the Lowdown belt buckle; the stories of the Johns Roberts as told in Rush songs; the Fishies, just because I love titling them. Also, it sounds hokey but I love giving people props for their material. I know how it feels to be bizarrely proud of a sentence, and to have someone notice and compliment-well that's nice. I know, I'm a geek.

Also, recurring motifs: Mixtapes. MEL. My Sexy New Yorker. Blog Synchronicity (when something completely random coincidentally comes up twice in one day-I would so love it if that actually made it into the blogger lexicon). Gina Kolata. Tom Friedman's mustache. New York Media Secretly Loves Showtunes. And, of course, Canadians: The Shadowy Strangers Among Us.

Which have been the most popular with readers?
My Jon Stewart round-ups. I was shocked at how instantly popular those were - according to Elizabeth they were the most-trafficked posts OF ALL THE BLOGS, at least at the beginning; it probably had something to do with the new set and at least what I perceived to be the new Jon. But man, they take forever. PlameGate. Lots of reader mail on PlameGate and Judy going to prison. What else–Dan Abrams' hair, strangely. On the flip side, I got lots of frustrated emails from people who couldn't understand why I liked Tucker Carlson. What can I say, I did, and I miss it at 9 because it was a great catch-all for stuff I missed that day. The late shift doesn't work for me–I have to blog Jon Stewart! Oh, the cruel irony.

Do you earn a set salary or is that contingent on how much you post or how many readers you get? Are there any restrictions on what you can or will post? Do you consider Fishbowl your full-time job, and how many hours a week do you spend working on it?
I earn a fixed amount every month for six posts per day, though sometimes it will end up being more or less as exigencies require. It balances out. Elizabeth has given me a shockingly free hand–at the beginning I would sort of let fly with a showtune reference or 80s lyric and kind of hold my breath, but she's been committed to letting me have a voice right from the start, for which I am extremely grateful. I totally consider Fishbowl my full time job–I have to say I freaking love doing this blog. I just enjoy the medium so much, I love the fact that it requires me to read amazing stuff by hilarious and talented people, and forces me to know what's going on in the world. Plus as a side benefit, I get all these random emails from people and end up having these really nice on-line relationships. That sounds dirty but it's not.

You mentioned that you're in constant contact with your fellow Mediabistro blogger Brian Stelter of TVNewser. Is there a camaraderie or sense of community amongst your fellow Mediabistro bloggers? Are you all in it together or are you competing for readers/hits?
And that's the other amazing thing: I love my co-workers. Garrett (Graff, FishbowlDC), Brian (Stelter, TVNewser) and Michael (Sonnenschien, FishbowlLA) are all talented and funny and so helpful–there is serious camaraderie there. I have to say I don't feel competitive with them in the slightest–in fact, we link to each other all the time, credit each other, congratulate each other, send each other links and tips–it's a total team. One of the things I used to miss, badly, when I freelanced was a workplace, and I have to say I have a great one.

Much has been made of the old school/new school newspaper vs. blog wars. Where do you see news and media bloggers such as yourself fitting into the world of professional journalism? Is there a niche you're filling that traditional print journalism can't or hasn't yet? Is there really a schism between the two media?
Blogs have the advantage of immediacy over print–it's just a basic fact. I just wrote about that the other day regarding the awful killing outside of Teany–it was a great example of blogs being more limber with respect to breaking news than a newspaper could be. Personally, I don't feel there's a schism between print and blogs. I mean, it must suck to work on a story and then get scooped by some kid with a wireless card, but other than that I think the two are ultimately complementary.

At Fishbowl, you've broken stories such as Elisa Lipsky-Karasz leaving Women's Wear Daily for The New York Post. Where do you get most of your tips from andhow much fact-checking do you do before going with a story?
You know, I don't actually remember who tipped me off to Elisa leaving. We get tons of tips through the anonymous tip box on the site, though it's frustrating because I can't ever email a tipster back for follow up, which is why I have to let a lot of good tips wither on the vine. I just can't risk printing something that might besmirch a reputation unfairly. Actually, I'm not much for besmirchitude in general, if I can avoid it. I never take a tip on face value–too many people have grudges.

You co-authored the book Stroke of Luck: Life, Crisis and Rebirth of a Stroke Survivor with Howard Rocket. How did that project come about and what did you learn from it?
Howard is the father of a girlhood friend–his daughter Amie and I went to junior high, high school and college together and were part of the same group of friends. He was in super shape, and then he had a massive stroke and almost died. When he came through he felt strongly that he wanted to share the experience, but was bedridden and could barely talk, let alone write. By this time, Amie and I hadn't seen each other for years but for some reason, she thought of me and suggested to her dad that I take on the project. I wrote it while I was in law school (and actually wrote the second half here in New York while I was summering at a law firm after second year). I was basically the family's biographer. That was unfortunately driven home recently after a member of their family died suddenly and I saw them all at the funeral–their relief at having that written record was pretty humbling. I think it turned out to be one of the most important things I have ever done.

You've written several neighborhood reports for the City Section of The New York Times, profiling people such as Karyn Bosnak of Savekaryn.com, Lynn Harris, creator of Breakup Girl,
and Blaire Allison of Marryblaire.com. How did you break into The New York Times, and do you have any advice on doing so? What about these profile subjects made them particularly newsworthy?

Ha–I broke into The New York Times thanks to MediaBistro, baby (hi Laurel!). Actually technically it wasn't the City Section–my first clip in the Times was in Metro Diary, my first assignment for my first Mediabistro class, which was also my first-ever New York media event. I wrote a poem called "A Canadian Moves South" about why I was staying in New York. It was January 2002 (I wrote it on a legal pad sitting in a partner's office at my law firm, I remember). I got home from class and decided to email it in. Two weeks later it ran. I remember I closed my office door and jumped up and down.

But I also owe the City Section connection to MB–I used their "How To Pitch" guide for the Save Karyn story (shopaholic with the pay-my-debt website). I think Karyn and MarryBlaire were newsworthy because of their sheer chutzpah–they were both going online and doing something that we'd never do but got results. I would just watch my inbox–when I'd get an email that someone just had to pass on I would see if it had legs. I did Odd Todd too, for the National Post back in Canada. For a while "quirky net innovators" was my beat.

You recently taught a class for Mediabistro on "Mastering the Lateral Move: How To Get Out of Your Current Position and Into Full-Time Journalism," something that you learned firsthand transitioning from being an attorney to a full-time freelancer. Firstly, what prompted the move from lawyer to writer?
I always knew I wanted to write–it's just what I've always done. That's why I've dabbled in so many other things–writing is the constant. I had never really wanted to practice law–something which was borne out by the practice of law–but I loved law school and I was really engaged by the material. I always knew I'd leave, it was just a matter of when.

What are the main points someone needs to know when contemplating such a move? Should they start freelancing first before they quit their day job? What are the biggest mistakes people make when first breaking into journalism and how can they be avoided?
DO NOT QUIT YOUR DAY JOB UNTIL YOU HAVE ESTABLISHED YOURSELF AS A FREELANCER! And even then make sure you have a hefty chunk saved up. And even then make sure you can go back if you have to. Your lifestyle WILL change and you WILL feel the pinch. It's what they mean when they say "wow, you're so brave." I didn't realize I was brave until my savings ran out. Oh, did I say brave? I meant stupid. That seminar was basically a "do as I say not as I did" cautionary tale. Oh well–you live, you learn, as a Canadian prophet once said.

You've covered a variety of topics, events and people in your varied journalistic career, from a New York Times piece on extras casting to women like Jennifer Garner who out-earn their mates to the World Hockey Championships in Russia. Are most of your pieces ones that have been assigned to you, or ones you've pitched?
Probably most pitched, though with magazines I find that I'm more often assigned stuff. The World Hockey Championships story was my break-in piece; I was living in Stockholm at the time (six month stint at my firm's Swedish office) and jaunted over to St. Petersburg for two weeks, and ended up staying at the same hotel as almost all the teams, many of which were NHL players whose teams didn't make the playoffs. It was kind of hilarious. Actually Alex Balk recently accused Canadians of all knowing each other (after I published my mom's high school yearbook photo of Peter Jennings) and I told him to name another Canadian and he named Todd Bertuzzi . . . who I hung out with in Russia (NB not "hung out with" if you know what I mean). I got unique stories because I traveled for them–the World Cup of Lawyers in Malta, the Nobel Museum in Stockholm. So, ironically, what made me broke is also what helped me get a career.

You also went from your natural brunette hair color to blonde for a Glamour piece. How did that switch go and do blondes have more fun? How far would you go for a story? Have you ever been asked to do a story like that that infringes on your personal life that you've refused?
I almost didn't do it–I self-identified as a brunette and frankly I was doing all right for fun. But it was such a cool story opportunity, to go blonde at a top salon on someone else's dime–and get to write about it–that I said sure. I did make them promise to take me back to brown when I was done with it. I'd do a lot for a story but I do have limits–my first opportunity for Glamour came when I got a call out of the blue asking me if I'd like to go write about Club Med Singles Week in Cancun. I had been dating someone for less than a month but I couldn't do it; didn't feel right to write about Single's Week when I'd be going up to my room to call my boyfriend every night. So I turned it down . . . and instead sent my friend who had just emerged from an awful divorce. She had sex on the beach with a hot Frenchman, and I got a Glamour story a few months later. Karma!

In yet another career, you've studied improv with the Upright Citizens Brigade, performed in comedy shows, and won a Best Leading actress award for your role in Behind the Badge in last summer's NYC Midnight Moviemaking Madness festival. Were you ever or are you now interested in pursuing entertainment full-time?
You are very generous Rach but it's a hobby, not a career. I love writing sketch and doing improv and performing in general (sorry, people I've ever done karaoke with) but I would be foolish to bank on that, especially now that I'm a little past the ingenue stage. But I love writing comedy, and improv was amazing for that. And being on stage gives you a different perspective when you're writing, I think. As for Behind the Badge, that was a really fun fluke–I was the ingenue in that, and it was really fun having people buzz around me and say things like, "Hurry! We want to make sure Rachel's hair catches the light!" (A sentence that will never again be uttered.) The award wasn't for the whole festival, it was for my category–Western. I found out about it in a Google search, and actually never heard from the director again, despite repeated emails. Draw your own conclusions.

You're currently part of Weekly Review: A Media Musical at Gotham City Improv, which bills itself as "the first ever musical comedy based entirely on ever-changing events in politics and the media," which features a new musical ever week. What's the timeline for writing the songs each week, and can you give us some of the highlights thus far and what we can expect in the future?
I love doing this show –the people are great, the material is hilarious and it's just so much fun. We turn the stuff around within a week or so, balancing 'breaking news songs' with set pieces and stuff that has a longer shelf life. I actually haven't written as much as I'd like but my big moment was performing "Look At Me, I'm Sandra D. (O'Connor)" as Ruth Bader Ginsberg. We've done a gospel/revivalist number for Justice Sunday, Bush singing a lullaby to frozen blastocysts and good ol' fashioned Broadway-style showstoppers to boot. Except for parody the music is all original, written by our director Tom Thomsen (fun name, too!) who doubles as our anchor. It runs Saturday nights at 10 pm at Gotham City Improv–this Saturday I get to do a torch song in a sweet sequined dress. Again, it would be helpful to still be in the forget-to-eat stage.

You’re originally from Canada, and got your start as a lawyer and writer there. Was the transition a smooth one for you? How has being Canadian informed your work and outlook?
Well, I took the New York bar so practicing here was never a problem–the case law in Canada is pretty similar to the U.S. As for writing, sometimes I still spell things the Canadian way, just for fun. I love being Canadian, it's a real honour.

When I go to Toronto I say I'm going home; when I return to New York, I say I'm going home. I love living in New York and I love being from Canada. I always get a kick out of Canadians who do well here–hence my trumpeting of Canadian journos on the blog. Evidently I still sound very Canadian; I am often asked to repeat the words "out" and "about," just for kicks.

Read Rachel Sklar’s daily media insights at FishbowlNY. Weekly Review: A Media Musical runs every Saturday at 10 p.m. at Gotham City Improv, 128 West 23 Street, 2F. Sklar will also be part of blogger reading series WYSIWYG Talent Show in September.