BILL SIMMONS: If you could go back to 2008 and tell yourself one thing, what would it be?
BARACK OBAMA: “You’re going to be busy.” Coming in, we were going through an unprecedented economic upheaval, combined with an upheaval in the Middle East that we hadn’t seen in our lifetimes. There was going to be a huge amount of disruption. I would probably tell myself to communicate more effectively early on than I did. We ran a great campaign. It wasn’t as great as it seems in retrospect—there’s always rose-colored glasses but there’s no doubt that we captured the country’s imagination. And somehow in those first two years, I think a certain arrogance crept in, in the sense of thinking as long as we get the policy ready, we didn’t have to sell it.
One thing I learned through some tough election cycles: You can’t separate good policy from the need to bring the American people along and make sure that they know why you’re doing what you’re doing. And that’s particularly true now in this new communications era. I think that we were ahead of the curve in 2008 in social media and the Internet and digital communications. When we came into office, instead of taking some of those lessons, we suddenly adapted ourselves to the White House press room and structures that had been built back in the 1940s and ’50s. As a consequence of those missteps early, we got the policies right, and that’s why the economy now has grown for five and a half straight years, six years, and why unemployment rates have gone from 10 percent to 5.1 percent. But there was a lot of political pain along the way that might not have been necessary.