“I certainly wouldn’t be here without a whole lot of luck,” says Riley Roberts.
As someone who’s had the unique pleasure of working with Riley side by side, I’d say luck had little to do with his success. At 28, Riley has led an impressive speechwriting career and has shaped the message for some of the most prolific political figures of our time.
“I remember when I first wanted to be a speechwriter,” says Riley. “It was during my internship in then senator Obama’s office. I was working for his economic policy advisor and I knew I wanted to be in politics, but wasn’t sure if I wanted to do policy or communications.”
“That was when the financial crisis was happening and I got to write a couple of floor scripts for the Senator. After seeing my words in print, I was so excited and realized this is what I want to do.”
“I had my eye on speechwriting from that day on and went after every opportunity to show that I was interested and eager to learn. I was fortunate that I got the opportunities that I did.”
Soon after his internship for Senator Obama, Riley landed a job as speechwriter for Congressman Joe Sestak’s campaign. The former U.S. Navy three-star admiral was running for a senate seat, and Roberts was at the forefront of his campaign.
Although Sestak was narrowly defeated by Republican nominee Pat Toomey, the week of the election, Riley heard through the grapevine that Holder was looking for a deputy speechwriter. He applied and got the job.
After 2 years as Deputy Speechwriter, the Chief Speechwriter left and Roberts was promoted to the position.
“I was really excited and really intimidated to work for the Attorney General,” admits Riley. “I’m not a lawyer and we’re writing about terror and crime and justice reform.”
“It’s a great advantage that Attorney General Holder is a wonderful guy– whip smart, fantastic sense of humor, and very informal. I can’t imagine working for someone better on so many critical issues… it was a dream come true.”
The work of a speechwriter
“People have a romanticized image of what being a speechwriter for the likes of the Attorney General is. Ninety nine percent of the job is you verses a blank screen. If you don’t really love that, and you’re not fairly good at it, you wont survive for long.”
“Speechwriting is you verses the computer. Then you get to be on the road, and meet new people. But I always loved writing so I approached it as a writer.”
“When you start to get burned out and lose that sense of awe… you should do something else. It’s a privilege to be in the room. You pinch yourself when you see the impact of those speeches or you’re providing advice and dealing with the White House, State Department, or CIA.”
“In 2013, I got to travel with the Attorney General Holder to the 16th Street Baptist Church in Birmingham, Alabama. We flew in for the 50th anniversary of the bombings– where 4 little black girls were killed. It was an intensely moving experience to hear from people who were there and be there with the community.”
“For Attorney General Holder, it was a deeply personal speech. I remember him telling me – this is for history. I felt like he was saying he felt the burden of that history that we were there to commemorate. It was an honor to see all these great speakers.”
From his years on the Hill and in the Administration, I know Riley had much wisdom to share. If you’re interested in a career as a speechwriter or writer, here’s what he says:
Be prepared to move fast
“There are only a few years to do this and be involved. This isn’t for someone who doesn’t have the time or energy to give it their all. This is your moment to make a difference so you absolutely have to seize it and that means working late and doing what has to be done. Do that and you will be rewarded by your colleagues and the greater institution.”
Be prepared to hold on to your idealism
“One of the most important things I learned from Attorney General Holder was the importance of holding on to my idealism. You have to fight day in and day out for what you think is right. The issues we were dealing with were so daunting… from national security to holding civilian trials to criminal justice reform.”
“I was always amazed by his ability to not pay attention to the BS and always be the same good natured guy.”
Be prepared to work as a team
“When it comes to speechwriting, I learned early on that writing a great speech is only part of your job. A huge part of your job is working with others, getting buy-in from people inside and outside the building to make sure that speech actually gets delivered.”
Be prepared to defend your work
“The other part is defending that speech during the vetting process. You have to have a sense of how the organization works so that you’ll be able to back up your reasoning for keeping the parts of a speech others think need to be cut.”
“If you fail to defend it, you risk losing your hope in your work.”
Be prepared to serve
“Attorney General Holder is an excellent role model. He is a true public servant. I have told him that there are people who work in Washington for 35 years and never have a chance to work for a boss like him. He brings no ego to the conversation; and treats everyone the same. He is warm and so idealistic. That’s what I really love about him.”
“In any position of authority I will carry this with me. Wherever you go and whatever you do, find a way to serve. You win peoples trust when they know they can rely on you and trust you.”
After Riley’s time with the Attorney General he went on to be a Senior Writer at West Wing Writers, a Washington institution.
In 2015, Riley married the love of his life, Elisa, in Normal, Illinois.
Riley holds a bachelors degree Political Science and grew up Wheaton, Illinois. He currently resides in Washington, DC.
(Update 2-16-2019: Riley is now divorced and dating.)