Theodore May ’08 (history), a freelance journalist who has spent the last three years reporting from and traveling in the Middle East. In 2010 he went on a 1500 mile trek in the Middle East following the footsteps of Alexander the Great, and blogged about it here http://alexanderthegreat.globalpost.com/ Most recently, he reported for USA Today from Cairo, and spent about two weeks in Cairo’s Tahrir Square.

Let’s start at the beginning; why journalism?

I was a history major at Middlebury, and I’ve always been interested in storytelling, which is essentially what journalism is. I hoped to use my knowledge of history, specifically of the Middle East, to tell better stories and write better articles about the region. After my junior year I had the opportunity to intern for a semester with the Daily Star in Lebanon, which certainly helped cultivate my interest in the trade of journalism. After graduating I really just wanted to go there and be on the ground, and freelance journalism was the easiest way for me to pay the bills, small bills, anyway!

Then what? How does one become a freelance journalist?

I had hoped to get a Fulbright or other fellowship after graduation, which are great options by the way, but it didn’t work out for me. I was basically itching to go travel around and write about the region I loved, which is the Middle East, but for others could  be Latin America, China, Europe, Africa etc. So I basically booked a one-way plane ticket to Cairo and hoped for the best. When I got there, I discovered that the best way to get started was with the small newspapers, so I got a job with small English-language paper, where they were in need of people who could write well in English and also communicate in Arabic. These kinds of papers and magazines are always looking for native English speakers who can write, even with a limited journalism background.

You’ve written for USA Today, National Geographic and Foreign Policy just to name a few. How did you move up from local Cairo papers to these global media outlets?

When I worked for the paper in Cairo, I covered mostly business and there wasn’t always a pressing story for me to cover, I got to explore and find other stories, events and angles to write about. I would write these stories up and try to sell them to all kinds of newspapers and magazines. Many morning I would wake up, go out into Cairo or across Egypt to find what’s happening–to find the action! There’s a lot of self-promotion when you work as a freelance journalist, because you’re constantly selling your work and your credentials to editors in hopes they will buy a story or pay you to cover something. This is what it takes, and that’s how I eventually got my longer assignment at Global Post.

Yes, your 1500 mile trek. How did you sell that to your editors and what was it like?

I’ve learned that the smaller the news outlet, the more open they are to ideas and proposals from young and up-and-coming journalists. I had written for the web-based outlet Global Post before, and when I approached them about a 8-month trek by foot across the Middle East, following the path of Alexander the Great. I wanted it to be a ground-level account of the people across the Middle East and their connection, knowledge and feelings about Alexander the Great. Above all the blog sought to expose the amazing diversity of people across the region, which we in the west don’t understand because these regular people are not covered on the news It was an amazing experience to listen to and write about all the different people I met, and to hear their different connections to Alexander.

You were sent to Egypt  by the Associated Press to cover the protests after your journey. As a journalist, what was it like reporting from Tahir Square in Cairo?

It was one of the most amazing places I’ve ever reported from. Every day I got to walk right out of my hotel and talk to all kind of Egyptians who were walking around, chatting, preying. It was really a fun atmosphere in the square and all sorts of businesses popped up to cater to the crowds: food stands, face painting and even a tent hotel. I was also astounded by the unity of the message; if you asked anyone who organized the protests they would say nobody did and that it was entirely organic–that’s the perception they wanted to give the media. And it was also the easiest place to report from, because everybody wanted to talk to me and I really didn’t have to go anywhere!

Any advice for the aspiring journalist?

Some general advice for everyone: start small. The local papers will be much more willing to hire you out of school, and you can gain valuable experience and build your portfolio of writing while you’re there. If you’re interested in covering foreign affairs like me, the best advice I can give is go there–wherever that is. Even if you don’t have anything secured, you need to be on the ground to network, talk with people, and find the action!