Saturday, December 5, 2009

Hello New York, farewell Chicago

Posted by Craig on 12/05/2009 15 comments
The last three months are hard to boil down into one post, but I'm going to try.

Since my last update on Sept. 7, 2009, when I made the transition from graduate student to undergraduate professor and celebrated one full year in Chicago, so much has happened.

It's been such a whirlwind that I haven't had time to update. Until now.

The class I taught was a great success; America's first Twitter journalism college class (not to be confused with the first Twitter class by Kathy Gill) engaged the students, sparked many great discussions, and it was a thrill for me, as I found I really enjoy teaching. But in the midst of that class, something funny happened.

I was interning at the Chicago Tribune with ChicagoNow at the time and before I get into what happened this October that threw my life for a loop, some more background on my choice of grad school and what's happened since.

I started grad school at DePaul University in September 2008. My primary goal was to set myself up to "work with a Web-savvy news organization full-time." That was stated clearly on my Web site from the start of that ride. We'll come back to that...

So at grad school, I jumped into contributing to local news sites like Windy Citizen, Chi-Town Daily News, and The DePaulia, and I worked on other reporting projects including going to D.C. to cover Barack Obama's Inauguration. I met everyone I could and did tons of networking.

Shortly after returning from D.C., I started Breaking Tweets, which took me through the ride of a lifetime since it began Jan. 31, 2009. I watched it grow exponentially, it allowed me to meet Guy Kawasaki and it was even blocked in Iran at the height of the Iranian Election dispute.

But as I operated Breaking Tweets, and watched it flourish, I kept asking myself, can this continue to operate independently? Can it ever make money? Can this be my full-time job?

All too often I found myself saying "no" and that scared me. The 30-40, even 50, hours a week I was putting into the site helped me elevate my online presence, and boost my Twitter followers, but not exactly fond of the spotlight, it also made me uncomfortable at times. I've always preferred to be someone behind the scenes, getting the work done and doing it well, but have never enjoyed getting too much attention. Still feel that way. (And the site was bringing me a lot of attention at DePaul, in Chicago, and even nationally and internationally.)

I eventually realized that even though the site never brought in money directly (other than the small amount from Google Ads), and even though the spotlight sometimes bothered me, it did lead to amazing opportunities: numerous speaking engagements at conferences and universities, an internship with the Chicago Tribune, the chance to teach an undergraduate class (and get mocked for it), and then... after a crazy October... the opportunity to work with The Huffington Post, a Web site I've long admired for its leadership and innovation.

How did it all transpire? Here's the story...

The Shift to New York

I never thought for an instant I'd be anywhere but Chicago for the foreseeable future after officially finishing grad school in August.

I had the opportunity to teach, I had my internship at the Tribune, and I knew I had a number of other potential opportunities if either of those didn't pan out long-term.

So I got an apartment by Wrigley Field, signed a one-year lease in mid-August, and was set until summer 2010.

The change of plans went like this...

I mentioned above my frustration with dedicating nearly all my energy to a Web site that wasn't making a sustainable income. I met with several entrepreneurs and journalists in the Chicago area to get their input. One talk, with Eric Olson, founder of Tech Cocktail, stood out. He said talk to larger media organizations, try to forge a partnership. Think bigger.

Sept. 28: I wrote a 10-paragraph email to Arianna Huffington, trying to keep it as brief as possible while at the same time elaborating on my background, Breaking Tweets, and my admiration for The Huffington Post, and asking about the potential for a partnership or some other arrangement, noting I was "open-minded to what that could be."

Oct. 3: To my surprise, I got a reply from Arianna in my inbox. She connects me with HuffPost CEO Eric Hippeau so we can discuss possible opportunities to work together.

Oct. 12: I talk with Hippeau for a good 30 minutes during a break at my internship. He says it was a great initial conversation and he'd like me to follow-up with CTO Paul Berry on ways we might work together.

Oct. 22: I talk with Berry, also for a good 30 minutes. He suggests I come out to New York City to discuss further. He isn't kidding...

Oct. 26: I arrive in New York City (talk about making plans on the fly) after an Amtrak train ride all the way from Chicago. I meet with several editors and executives of Huffington Post about a possible job that would have me doing similar work to what I've done with Breaking Tweets.

Oct. 30: I receive word from HuffPost that I might be offered the job "Traffic and Trends Editor." I tell them I would accept....

Nov. 3: I get a phone call from Arianna Huffington herself --- bringing the whole thing full circle --- and she welcomes me to the team.

Just one month after that first response from Arianna, all of a sudden, I was set to be moving to New York and joining HuffPost full-time.

It was a dramatic and unexpected series of events. I gave DePaul notice, finishing the term for my class (which ended mid-November), and worked like crazy to get my Chicago apartment subletted and find a new place in New York.

I was unsuccessful finding a taker for my Chicago place, despite a ridiculous amount of tweets (sorry all, I felt like a spammer), but I got luckier in New York, finding a place in Brooklyn on my very first Craigslist try (first person I called, first place I saw).

I began working remotely with HuffPost on Nov. 9. I left Chicago after breaking my lease on Nov. 30, and I drove a Budget truck (with my mom's help) to New York, arriving Dec. 1. My first day at the HuffPost office was Dec. 2, and first full day Dec. 3.

And here I am. Sitting at my apartment in Brooklyn. Still somewhat mesmerized by what's transpired. Extremely grateful, very excited, and hopeful for what this next chapter of my life will bring with a full-time job at a "web-savvy news organization" in the Big Apple - just across the state from where I grew up in Buffalo.

(NOTE: One big question I do have is what to do with Breaking Tweets, and would love to hear people's thoughts. I clearly don't have the time and resources to update it personally anymore, yet I'd hate for the domain name and Twitter account with 13,000 followers to remain idle. Thoughts?)


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