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Hill Climbers: For Orlando Watson, Timing on Hill Was Elementary

Capitol Hill was never in Orlando Watson’s plan. Convinced that the private sector creates more value for society and that politics was becoming too divisive, the new press secretary for Rep. Paul Gosar, R-Ariz., decided to major in public policy at the College of William & Mary in Williamsburg, Va.

But in 2008, on the advice of his college professors, Watson began to take a good look at presidential candidates across the political spectrum — and that’s when then-Rep. Ron Paul caught his eye.

“The more I learned about Dr. Ron Paul, the more I became … sort of reinvigorated,” Watson said.

It was two years later, when he graduated, that Watson jumped at the opportunity to work on the Senate race of Paul’s son, Rand Paul. The Kentucky Republican’s campaign was the first for which Watson had ever worked.

And timing was everything.

“If I had graduated a year earlier or two years earlier, or a year later, I probably would be doing consulting work like the rest of my miserable friends,” Watson joked.

During the campaign, there was no task that Watson wasn’t tapped for. He traveled with Rand Paul, dealt with press inquiries, handled media booking, videotaped events and helped out with advance work for fundraisers and campaign events. At one point, he was even the candidate’s driver.

His work and adaptability paid off, earning him a job as a press assistant on Paul’s Capitol Hill staff after the senator was elected.

Watson, 24, credits his success to four things: “ambition, hard work, timing and opportunity.”

Having moved from New York to Virginia when he was 16, the move to Washington, D.C., itself wasn’t a difficult transition — but the move to Capitol Hill was all new.

“It’s fun; it’s young,” Watson said of working on the Hill. “The Capitol grounds is like a big campus — so it definitely reminds me of college.”

But the slower pace of work on the Hill, compared with the action-packed campaign, took some getting used to. A lesser frustration was learning to navigate the Capitol complex.

“I’ve got an awful sense of direction. My navigational skills aren’t good … so I would get lost all the time,” Watson said.

It wasn’t long before Watson earned a promotion to deputy press secretary in Paul’s office.

It was around the same time that Watson’s business drive caught up with him — resulting in the creation of his own hyperlocal news aggregation website for the Washington metro area,

“I was putting together the daily news clips for the office for a while, and it was sort of like my own personal Drudge Report, and I thought to myself, ‘Well, if I can do this for the office, why not do it for all of D.C.?’” he said.

So he got together with a friend and began working on the project, which ended up providing a valuable, yet somewhat disappointing, business lesson.

“There’s a phrase in business, ‘Build it and they will come’ … but ‘Build it and they will come’ does not work.”

Watson is no stranger to hard work and commitment. His grandfather, an immigrant from Barbados, is the inspiration behind the work ethic his Hill colleagues have come to admire. He also happens to be the person who shaped Watson’s conservative worldview.

“He emigrated to this country and worked really, really hard to provide his family a life,” Watson said. “He was personally conservative, very thrifty, cared about family and community.”

With an example like that to live by, Watson said he feels frustrated by a view of conservatism he said doesn’t sit right with him.

“People define the word conservatism today as meaning sort of backward or authoritarian or stuck in the past, but that’s not how I define it at all,” he said. “I care about the middle class and the working poor, and people who are trying to achieve the American dream — just like my grandfather.”

Watson stayed in Paul’s office until recently, when the opportunity to become press secretary for Gosar arose.

And he is as full of praise for his new boss as he was for his old one.

“He’s a great listener; he’s funny; he’s got a good sense of humor. He’s willing to listen to his staff,” Watson said of Gosar.

But most importantly, he has “a strong conservative backbone,” and that’s what it’s all about for Watson.

“Had I not been doing work that I find meaningful, I would have left the Hill a long time ago. If I felt like I was just shuffling papers for prestige. But the work that I do, I think, is actually meaningful.”

No two paths are the same, but Watson’s advice to anyone looking to start a career on the Hill is simple.

“One: Work on a campaign. Two: If you can’t do that, get an internship and work hard at that internship. Three: You know, if none of those fit your bill, always be networking, because you need to know someone.”

Thinking ahead, he keeps the advice of a friend in mind.

“Don’t plan ahead too far into the future, because tomorrow you might wake up and get hit by a bus and everything changes,” he said. “Right now, I’m just focused on doing the best I can in the job that I have.”

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