On the day after the Republicans kicked our butts in the 2014 midterm elections—enlarging their margin in the House of Representatives and taking control of the Senate for the first time in eight years—I sat at my desk in the West Wing waiting for the bell to toll. At the time, I was the White House senior adviser for communications and strategy, and had been advising Barack Obama on media strategy and message since right before he started running for president back in 2007. I was into my third hour of looking at the devastating exit polls and turnout numbers when I got the call to come down to the Oval Office. I was pretty confident that I wasn’t being fired, but I wasn’t looking forward to this meeting, either.

We always knew that 2014 would be tough. On the flight home from Chicago the day after Obama’s re-election, in 2012, strategist David Plouffe pulled up the 2014 Senate map and declared to everyone on Air Force One that the Democrats were going to lose seats. The only question would be whether Obama could defy political gravity just enough to hold on to the majority. He didn’t. Democrats not only lost in deeply red states like Arkansas, Alaska, and Louisiana, but we also lost in states like Colorado and Iowa that had gone strongly to Obama just two years prior.

When I trudged into the Oval Office, Obama was seated at the Resolute Desk. “Pfeiffer, tough night,” he said to me as he glanced up from the briefing he was reading. Obama was always at his most hopeful after a tough loss. I never knew how much of this phenomenon derived from his eternal optimism or the obligation he felt to be the “hope” guy. Either way, his staff always appreciated it.

I sat down in the chair next to Obama’s desk, the site of many conversations over my nearly six years in the White House. “In 2008,” he said, referring to our communications strategy, “We were so far ahead of the curve. Governing is harder than campaigning, but for most of our time here, we have at least kept pace with the change. Lately, it feels like we have fallen behind.”

I had been anticipating this chat, because the president was correct. We had been on the defensive for the last 18 months. Every time we would get a little momentum, something would knock us back on our heels. Obama was referring to his White House in 2014, of course, but whether the president knew it or not, he had presciently hit on a larger problem within the Democratic Party that would help facilitate the election of Donald Trump in 2016—and one that could prevent the Democrats from winning in 2018 and 2020.

The Democratic communications advantage that the Obama campaign built in 2008, and built upon in 2012, was gone. The ground had shifted under our feet. The media environment had changed and it had changed in ways that benefited the outrage-fueled messaging of the right wing. If I had better understood how dramatic this change was, I wouldn’t have been so sure that Trump was going to lose in 2016.

In early 2011, David and I were interviewing candidates for press secretary to replace Robert Gibbs, who had decided to leave the White House. Late one afternoon, we were meeting with Jay Carney in Gibbs’s spacious office while he was on the road with the president. Jay was a well-known and well-liked former bureau chief for Time, who had left journalism to become Vice President Joe Biden’s communications director. Unlike most who make the transition from the press to politics, Jay had done it seamlessly. He was probably the sixth or seventh candidate David and I had interviewed, and we had our routine pretty much down pat. The last question we asked every candidate was: “What piece of advice would you give us to improve our communications strategy?”

This is usually a good question to see if a candidate had the courage to tell you something you don’t want to hear; and at bare minimum, if you are going to spend hours interviewing people, all but one of whom you aren’t going to hire, you might as well get some free advice out of it. Jay had a particularly illuminating answer. “You guys pioneered ways of using the Internet to communicate directly with the public without going through the press,” Jay said about our 2008 campaign. “You should keep doing all those things, but maybe don’t rub the press’s face in it so much. You have to understand: reporters are going through an existential crisis where they don’t know if their job or industry is going to be around for that much longer.”

Jay’s comment summed up media in America, which was in a state of massive transition and turmoil, with regular announcements of layoffs and legacy-media outlets shuttering their doors. David and I both took what Jay said to heart. Soon after this meeting, the president hired Jay as White House press secretary.

The existential crisis that Jay referred to was a long time in the making, but when it happened, it happened fast. Someone (not me) could write a very long book on this topic, but let me do the CliffsNotes version. First, the Internet allowed people to get information without paying for it, which was not good for the newspaper business, which sold ads based on the number of subscribers. Second, the Internet and the smartphone made it so people could get information whenever they wanted it, wherever they wanted it, which was not good for the television industry, which sold ads based on the number of people who sat down to watch TV at an appointed time. Third, the 2008 financial crisis crushed the very businesses that bought the ads that funded the media industry. Newspapers were laying off people or closing altogether. The more experienced reporters were being offered buyouts, so outlets could replace them with cheaper, younger reporters. You now had fewer reporters with less experience and fewer editors writing more often to meet the never-ending deadline of the Internet.

Fourth, while media was weakened by technology and economics, it was also losing its sacred place in our democracy in the eyes of many Americans. By the time Obama had started running for president, the halcyon days of journalism were a distant memory. Public trust in the media declined precipitously, and by the time Trump won the 2016 election, the media was about as popular as Trump himself. Some of this decline can be attributed to a rise in skepticism of American institutions, but the media is not blameless either. Several high-profile incidents have given the public legitimate reasons to be more skeptical. Foremost among these is the coverage of the run-up to the Iraq war, where the media—and The New York Times, in particular—parroted the Bush administration’s false claims about the presence of weapons of mass destruction in Iraq.

Finally, the Republican Party and the right-wing media had been running a decades-long effort to convince their voters that the media was their enemy and to create an alternative version of reality. Fox News, the Republican propaganda outlet, which marketed itself under the banner of being “fair and balanced,” was the embodiment of the effort to nullify news that ran counter to the political wishes of the Republican Party and conservative activists.

All of this meant that Obama was entering office at a time when it was harder than ever to reach people through the news media, and people were more skeptical than ever before about anything they learned from the media. Not exactly a recipe for success for a new president (and his communications director) trying to tell the country about his agenda.

These changes created several media dynamics that defined daily life in the Obama White House and set the stage for the election of President Trump. During the ’08 campaign, our press strategy was geared toward the idea of always being on offense. This was a simple concept: we wanted to make news early in the day to push the political conversation, which in those days occurred primarily on cable TV, in our preferred direction. We wanted the media and our opponents to react to our news throughout the day, as opposed to forcing us to react to theirs.

Therefore, we would get up before 5 A.M. most days to make announcements of new endorsements, new television ads, or new policy proposals. Nick Shapiro, who was a deputy press secretary on the campaign, was assigned the task of getting up every morning to send out our news of the day at 5:30 A.M. for the network morning shows. Nick did this task without fail or complaint for months. It wasn’t till a year after the campaign, when we were both working in the White House, that I learned that Nick didn’t have Internet in his apartment, so he was getting up every morning and going to a nearby hotel to steal their Wi-Fi to send out our press releases, seated among a group of prostitutes that gathered in the lobby of the hotel at the crack of dawn.

That strategy now feels like a relic of a bygone age, before Facebook and especially Twitter became the arenas in which political combat occurred. By 2012, the news cycle moved so voraciously that we stopped making announcements early in the morning, because it would be old news by lunchtime. The political media machine—which was made up of an ever-growing collection of media outlets, cable channels, Web sites, bloggers, and tweeters (so many fucking tweeters)—now had an insatiable appetite for content. The news cycle was dead; long live the content monster.

As with most things, the Internet is to blame for this. First, the news cycle is dead in the eyes of the consumers; they want news immediately on demand. They don’t want to wait for the 6 P.M. news or the next morning’s paper to be delivered to get the latest news; they want to look at the news on their phone at any hour of the day, while killing time in line at the grocery store or sitting on a city bus. This means that reporters are basically working 24/7, updating stories posted earlier, and writing new stories as soon as events dictate. Second, digital advertising—the revenue source for most media in the modern era—is a volume game. The more content you create, the more ads you can sell, and with declining print ad sales, you need to make up the difference somewhere.

This means we live in a never-ending, always accelerating news cycle, which makes the brutal White House lifestyle more brutal than it has ever been.

My daily routine, particularly in the early years of the White House, was as follows:

4:50-5 A.M.: Read e-mails on BlackBerry that came in over the five hours or so I was asleep

5–5:30 A.M.: Shower, get dressed, read e-mails that start to come that morning from reporters. E-mail the morning tip sheets to ask them to include articles from the papers that fit our message and vigorously (sometimes over-vigorously) argue against the inclusion of articles that did not fit our message.

5:30–5:45 A.M.: Drive to the White House.

5:45–7:05 A.M.: Talk on the phone with White House correspondents preparing to go on the network morning shows, while I drive to work and eat breakfast at my desk in the White House.

7:30 A.M.–7:30 P.M.: Attend endless series of meetings (scheduled and impromptu) and take nonstop phone calls while careening from crisis to crisis (real and manufactured).

8–10 P.M.: Clean up desk, work on to-do list for the next day, drive home, and eat an unhealthy dinner at an hour later than any doctor would recommend.

10 P.M.: Log on to The Washington Post and The New York Times Web sites to read the next day’s stories that just got posted, begin e-mailing with other colleagues to craft responses to any problems, or e-mail reporters to fight for changes to any inaccurate or unappealing parts of those stories. Eventually go to bed, rinse, repeat.

On Christmas Eve in 2009, right after the Senate passed the latest version of the Affordable Care Act, I stopped by the office of White House Chief of Staff Rahm Emanuel. I was about to head out of town for my first days off since Obama had won the nomination. I wanted to check in before heading for the train station. Rahm was a top adviser in the famously chaotic Clinton White House for more than six years, where he dealt with countless calamities, including the effort to impeach the president. As I was bidding him farewell, Rahm looked up from his BlackBerry, rubbed his eyes, and said, “This year felt longer than all my years in the Clinton White House combined.”

Everything was moving faster than ever before. Politics and government were now operating at the speed of the never-ending news cycle. What used to take weeks now happened in a matter of hours. When you used to have a day to respond, you now had minutes—if you were lucky. And it’s only gotten worse since then. Much, much worse.

For most of my time working for Obama, whenever we encountered some Beltway political crisis that dominated cable news, we would ask focus groups of voters if they had heard anything about it. There were things that Washington got worked up about, and things the American people cared about, and rarely did those things overlap. But something had changed. Suddenly, focus groups knew all about the trivial things that Washington would get worked up over, and they knew about them in great detail, often reading back to the moderator what sounded just like Republican talking points or a Fox News story—which are actually the same thing.

When the moderator asked them where they’d learned this information, the answer was almost always the same: Facebook. It was the perfect petri dish for a fungus like Trumpism to grow. Trump understood that there were no rules and referees and that a good story was much more valuable than an accurate one. Trump’s main media experiences are the absurdity of reality television and the no-holds-barred world of New York tabloid journalism. Sadly, these were the perfect experiences to compete for president in 2016.

In hindsight, it seems obvious that Trump would thrive in this environment.

The hints were there all along. After that meeting in 2014, Obama sent me to Silicon Valley and New York to pick the brains of the smartest people in tech and media to better understand the current state of affairs and where things might be going. I went to Google, Twitter, YouTube, LinkedIn, and everywhere in between. The gravity of the challenge before us came in a meeting in Silicon Valley, when I explained the difficulty in getting our message out in the fragmented media environment, and one of the executives from a Silicon Valley giant responded: “We have been wondering the same thing and hoped you had some good ideas.”

Democrats need a better answer sooner rather than later.

Adapted from Yes We (Still) Can: Politics in the Age of Obama, Twitter, and Trump, by Dan Pfeiffer, to be published by Twelve.