You’re one of the last charter Team Obama guys still on the job. What’s keeping you around?
I never set out to work in the White House. What drew me to the campaign was really the opportunity to work for Barack Obama. I don’t necessarily see this as a situation where I’m going to be going through the revolving door, in and out of administrations. I happen to have found somebody who I really love to work for, who I have a really good relationship with, and it’s hard to walk away from that.
Do you ever feel envious of friends you started with, who’re out now and setting their hours?
Anybody who leaves here, you see them a couple months later and they look a lot better. They look 20 pounds lighter and five years younger. So it does give you some envy, because you see the physical toll the job takes on you. You see everybody moving, some in Washington, some out to California, and you realize there are many green pastures out there. I still come to work in a windowless office in the basement of the White House. But the other side of the coin is that there’s no other job like this. When you walk out that door for the last time here, you realize your ability to be at the center of events and decision-making on momentous things that are changing the course of history, that goes away. It cuts both ways.
You had a choice when you entered public life between this and pursuing a career as an author. Is that still the plan when you leave?
I had originally been looking at writing, including fiction. When I leave here, I would certainly want to do my own writing, but more in the non-fiction realm — books, long-form journalism, and related opportunities. So I haven’t given it much thought beyond that. But after writing for somebody else for so many years, it will be interesting to pivot back to doing things in my own voice.
What advice would you give to somebody who wants to follow your path, about the most relevant experience you had to land you this job?
People make a mistake when they think that if you just accumulate a set number of things on your resume, it’s going to lead you to a particular place — the pattern of essentially compiling credentials to climb your way up a ladder. That may work, but that’s not at all what happened to me. I found people I really wanted to work for; I made myself available to do whatever I could with the skills I had; I took some risk, packing up and moving to Chicago; and I looked for the opportunities that fit for me. So I think the biggest advice is to find people you love to work for who you’re going to learn from.
You and the President obviously spend a lot of time together. Do you have any travel rituals? What do you do on the plane?
He’s a card player, I’m not. But I’ve gone on all of his foreign trips. We’ll have very intense schedules. One ritual is he likes to find little pockets of down time in the day to just unwind, talk about other things, to be relaxed. But the one ritual that’s always the case is that on speeches, he works very late, so he’ll constantly be making line edits and fiddling with text up until the last minute. So you get a lot of late nights, especially on the big speeches. So you have to kind of pace yourself with the expectation you’re not going to get a lot of sleep, that you’ve got to find ways to relax over the course of the day and that you need to have a reserve of mental energy that you can draw from. That’s the rhythm that you get into on these foreign trips that can be quite a grind.
When you’re actually in the White House, how long is your typical day? Can you characterize it?
I’ll get in around 8 and get an intelligence briefing at the beginning of the day, and then go into a series of morning meetings that are about figuring out what we need in place for that day. The afternoons tend to be meetings or work on what policies are running through a process, what are the next big things we’re getting ready for, the next big trip, the next big speech, the next big rollout of a policy. And I’ll tend to be at work from 8 to 8. But the thing about this job, it’s not so much the hours in the office—it’s that you’re always on call. So you’ll end up having to answer email and do things up until you go to bed at 12 or 1 in the morning. So even when you’re home, you’re still working. That’s particularly true in foreign policy. The other day, when we launched airstrikes in Syria, we obviously knew that was going to happen, but that happens overnight, so you basically end up being up all night. You don’t get to control the timing of when things happen in foreign policy like you do in other areas. If something happens in North Korea, or the Middle East or Ukraine, you have to respond to it no matter what time of day it is. So it ends up making you essentially on call 24 hours a day.
What’s the most important speech you’ve worked on so far? I’m wondering where the UN speech ranks.
The UN speech is definitely one of the most important, because it’s intended to set the tone for the next year or so going forward, here in the United States but also globally. It’s the roadmap for we’re doing, where we’re trying to go, what we expect of others. There have been a handful of speeches like that. The Cairo speech in 2009, in some ways the Nobel speech he gave, which in some ways was a window into his view of the world that endures well. They break through in a way because they’re bigger than the precise moment we’re in. They’re about laying down markers for what’s going to define the U.S. role in the world for a period of time to come.
Photo: Pete Souza—The White House/Getty Images
Did you revisit the Cairo and Nobel speeches in writing this one? How’d they inform it?
I actually find the two things I always try to do before working on a big speech are to go back and read relevant speeches by President Obama and by other presidents. It’s interesting to see how other presidents deal with similar moments in time. How did other Presidents speak at the UN at times of significant international turmoil or the beginning of a military action? For President Obama, I often try to go back and look at the foundational speeches. So, what did we say at the UN in previous years? What’s in Cairo speech, what’s in the Nobel speech, even going back to the campaign. And you try to find a thread you can pull forward and update. Even sometimes there’s specific language that you seek to use again to make sure there’s a thread of consistency to the message.
Are there speeches by other presidents you referenced specifically for his latest UN address?
I looked at the 1961 speech to the General Assembly by John F. Kennedy, and I actually ended up putting a quote from that speech in this one. There, too, the theme was essentially a world at a crossroads and having to make a choice between different paths. And so that ended up impacting how we framed this speech. We looked at others, too, and it’s interesting to see how different presidents make use of that particular world stage.
Looking past the current military campaign, how hopeful are you about a lasting peace, in whatever way you want to define that, presiding in the Middle East in the mid- to long-term? Some people are seeing nothing less than a civilizational collapse that’s not fixable in our lifetimes.
The reason I have to optimistic is that it’s the one thing everybody in the region seems to agree on–that this is such a shocking organization that it’s stirred people out of complacency and opened the doors to alliances that weren’t previously possible. We had the Iraqi prime minister in a meeting with the five Arab nations in our coalition, who have Sunni-led governments. That would not have been thinkable even six months ago. If everybody maintains the current sense of urgency, you can see a pathway for this group to be steadily eroded, but also something better taking its place in terms of a new approach to regional stability. And the other thing I’d say is we can fall into a trap of making these groups and threats out to be more resilient than they really are. With Al Qaeda, we’ve shown that if we just keep the pressure on and have a consensus against an organization, the organization in Afghanistan and Pakistan for intents and purposes is at best a shadow of its former self. The challenge is now doing that in the heart of the Middle East with this group and other extremist satellite. But part of the reason the President gave the speech that he gave is to make clear this can’t just be us launching a bunch of airstrikes. This has to be a much broader effort.
Most of our readers would agree with the assessment behind the rebalance to Asia, that economically the center of gravity in the world is shifting there. It also seems unavoidable with ISIS, and Israel, and Ukraine, and Ebola, that your focus is directed elsewhere right now. How do you deal with that?
You have to be very disciplined to make sure that even as you’re working the urgent issues, you’re not neglecting what I’d say are the opportunity pieces of your agenda. And the rebalance to Asia is certainly part of that. So for instance, when I went up to the UN with the President, even as we had to work on the speech and all the elements of the coalition building, I carved out two hours for a meeting with the presidential advisor from Burma to talk about the President’s upcoming trip there. It would have been easier to just scrap something like that and focus on ISIL. But you have to be disciplined and remember that you have to focus on the opportunities in the world and not just the threats. The fact is in the long run those may end up making a bigger difference, because there you can make progress and you can build new ways of doing things. The key to it is looking at your schedule at the beginning of the week, and saying to yourself, As easy as it would be to only do the Middle East this week, I have to set aside some time for Africa, for Asia, for Latin America—which we generally define as the opportunity regions—and be sure we’re hitting our marks on them.
You’re part of the first brother team to make this list. What was your dynamic with [older brother David, president of CBS News] growing up? Did you argue politics over the dinner table?
We always got along very well. We definitely had different political perspectives. But in my family we were encouraged to argue about everything over the dinner table. And I think since then, we’ve never been competitive, in part because we’re in different fields. He’s in media, I’m in politics and foreign policy and that makes it easier for us to root for each other without competing in the same territory.
Does knowing him make you more or less cynical about media?
Seeing his perspective about what people are interested in over the years definitely helped me understand that the media is in a high pressure business of their own and they have to find ways in a crowded information environment to report the news in a way that gets peoples attention. It gives me an understanding of the dynamic on the other end of the phone when I’m talking to a reporter, which I have to do a fair amount of.
This story is from the October 27, 2014 issue of Fortune.