Originally published in TheLi.st @ Medium Collection
When I quit being a lawyer in 2002, many people told me I was "lucky" and "brave." I had $40,000 in my bank account and no plans, so I sure felt lucky! But "brave" I didn't get, mostly because I was still several rent payments, billing cycles, and far-flung trips from that $40,000 dwindling down to zero. Once that happened, I got the "brave" part.
I've been "brave" a lot during my professional career, as I've gone back and forth from secure full-time gigs to the wildly insecure worlds of freelancing and entrepreneurship, and the variations in between. It has not always, or often, been easy. It has, however, been interesting. I've gone out on limbs, flung far, and Forrest-Gumped my way into the center of the action. As a matter of personal philosophy, I have generally said "why not?" far more often than either "why?" or "not." I have done things. I have done things. As a result, I am frequently told that I am "lucky."
It's true, I am. I feel lucky every day. But I can also trace that luck back to decisions I have made. Frequently those decisions have been to pay my own way to somewhere I want to be and something I want to do.
Here is one.
In mid-2005 I was the writer and editor at FishbowlNY, a New York-based media blog at Mediabistro.com. I had been clumsily freelancing for a few years and it was my first official job in media. Some of the big stories at the time were the Newsweek Koran debacle, which triggered the beginning of the press pushback against the Bush administration; the morning-show ratings rivalry between Katie Couric at Today and Diane Sawyer at Good Morning America; and Brian Williams starting a blog. There was another big story--the launch of the Huffington Post on May 9, 2005.
Panned as an utter disaster before it was a full day old, the Huffington Post pushed everyone in media off-balance--who were these people on its front page spouting their opinions about the news? Steven Weber? Alec Baldwin? Ellen DeGeneres? The highbrow journalism set sniffed; everyone else angled to get a spot on what had suddenly opened up as new online real estate. It was the mid-Aughts and, for context, six months before the publication of Clive Thompson's seminal New York magazine story on the rise of blogging, which blared its importance from the cover via the hugely-fonted word "BLOG." Any new media property on the web was increasing the web's real estate by a significant factor.
I took this photo of the first-ever HuffPo front page from my boyfriend's computer screen at 6:04 am on May 9, 2005. Not a screenshot, a photo. I was pretty hi-tech. The tagline read, "DELIVERING NEWS AND OPINION SINCE MAY 9, 2005." Arianna & team took the long view. Smart, as it turned out.
I tracked it from my perch at my desk in my apartment on the Lower East Side, on my computer literally held together with a paper clip, staying up all night until the switch flipped on the 9th and covering the Huffington Post avidly from then on, including who was posting what and what everyone else was saying about it. Arianna seemed confident and glamorous as she blogged her blogs about blogging, and took hikes with fabulous women in media who tried to game out Judith Miller's source (2005!).
When Gawker founder Nick Denton invited me to a party he was hosting for Arianna at his fabulous Soho loft in September 2005, I was ready. I pinged my friend Doug to be my date, because, sure, he was delightful company but he was also a former model. I asked my Greek friend Anastasia how to say "Welcome to New York!" in Greek. I bought a fancy red tube top with strategically placed sequins that I thought was very sophisticated. (Oh, 2005. I think I miss your tube tops most of all.) I just wanted one minute with Arianna. Just so she could meet me, and know who I was.
Gawker Media founder Nick Denton welcomes partygoers to his apartment in September 2005 and toasts his guest of honor, Arianna Huffington. Then-NYObserver editor now-Capital New York founder Tom McGeveran tries unsuccessful to get out of frame. Photoset by Nikola Tamindzic.
The party was packed. Dougie, model-tall as well as handsome, scanned the crowd over everyone's head to find our quarry. There were always throngs of people between us and her. The speeches came and went. I started to quietly panic. I had one purpose there, one alone.
I was just really, really, really excited to be there. Photoset by Nikola Tamindzic.
Suddenly she was coming toward us. I had my opening. "Hi Arianna. I'm Rachel Sklar from Fishbowl New York!" She was instantly warm with recognition, which I took to mean she'd recognized me. But you never know.
That's Michael Stipe in the corner, that's Michael Stipe in the spotlight with Arianna Huffington and Eric Alterman. Photoset by Nikola Tamindzic.
"Oh, I looove Feeshbowl!" she said in her beautiful musical accent, enveloping me in a cloud of perfume. I fell instantly in love with everything about her including her shiny hair. This was it. This was the time to make my mark. This was the time speak Greek. "Kalos orises! Ella New York!" I said, obviously mangling the pronunciation as her brow furrowed. Panicked, I said the only other word in Greek that I knew. "Malaka!" I blurted, and her face went from shock to amusement, then laughter. If I am not mistaken. I had just called her a fucking masturbator. I would have launched something desperately into the pause that followed, but suddenly Nick Denton was swooping down on us. "Arianna! Have you met Jessica Coen?" Jessica was the talented, comely Gawker editor, and this party was basically meant for her. I bowed out gracefully, Dougie in tow. I remember nothing else from that night.
The next day in my blog recap, I inserted an Easter egg: a sound file link to the title song from "Never On Sunday," which Anastasia had assured me was my closer. It was. Arianna e-mailed me how much she loved that song, and how nice it was to meet me. Pro-tip: Trust Greeks bearing gifts!
We stayed in touch. A few weeks later, she let me know she was having a party at her home in Los Angeles, for Nick, to return the favor. Would I be in town? "I would!" I said, and then booked a ticket.
Let's talk about money for a minute. At that point in my life I was pretty broke. I made a modest honorarium from FishbowlNY and made up the difference with temp legal gigs, but I was leaning into this whole full-time writer thing and, well, times were lean. I felt like if I just put in the time I could eventually make it to solvency. (I faintly remembered solvency and I missed it.) Still, building a career for myself doing what I loved seemed like a good trade-off. Plus, my parents spent a lot of time in Palm Springs and I knew that if I could combine a family visit with my fancy LA party I'd be able to just pull it off. I booked the ticket.
My parents were excited for me, and though I had packed a suitcase worth of potential outfits, took me shopping at White House/Black Market where I picked up a sparkly little cream shrug to wear over my black--yes--tube top. They also knew I was toughing it out and sprang for the $100 shuttle ride from Palm Springs to Los Angeles (er, I suppose this is where I admit that I can't drive.) Mediabistro had alotted $100 for expenses which mostly covered my very fancy hotel room at the Comfort Inn Santa Monica and did not cover the $18 bottle of wine I picked up at Wine Expo at 2933 Santa Monica Blvd, where they were so nice in helping me pick out something appropriately Greek that to this day I feel obliged to remain on their email list. Perhaps they felt bad for me, sweaty and frazzled and lugging my giant suitcase around Santa Monica. Cabs in LA are expensive.
Arianna had suggested I come over early since I had pitched an in-depth interview with her and had come all this way. She sent a car, and I luxuriated in the free ride to Brentwood--oh so free, so very, very free. We were having a glass of wine with her sister Agapi in the kitchen when Nick Denton walked in. I allowed myself to enjoy the look on his face. Sometimes it's fun surprising people.
I was just really, really, really excited to be there. Photo taken with my trusty camera, I believe by writer Mickey Kaus.
The party was great. The people were amazing. Bill Maher was there. David Mamet was there. Callie Khouri was there. I got to meet Megan Daum. There was a pool. There was food. I was there. Woot! Arianna was going to look after my ride home too and told me to stay till the end of the party, so we could talk further. I had my little recorder out. When everybody but a select few had left, we sat around and chatted some more before it was time for me to go. She presented me with a copy of her book, The Gods of Greece, summoned a ride back to my hotel and embraced me farewell in a final cloud of signature scent. I left even more in love with her than before, and couldn't wait to go write up my superfun, superexclusive interview.
Then I flew home.
Then I quit Fishbowl.
Then Arianna and her partner Kenny Lerer offered me a job.
And then, I joined the Huffington Post.
The day I accepted, Arianna was on The Colbert Report, and I was invited to attend along with the HuffPo staff. Afterward, she hugged me, put her hands on my shoulders, looked into my eyes and said, "We're going to change the world."
I can tell you that paying my own way to Los Angeles for that party changed my life.
Rachel Sklar is a writer/entrepreneur and founder of TheLi.st. She was previously the founding media editor at The Huffington Post and was one of its earliest hires. This essay was adapted from "Go Fund Yourself" from The 10 Habits of Highly Successful Women on Amazon. Honestly, Arianna smells amazing.