“I kind of pooh-poohed the experience stuff when I first got here. But this shit is hard.”

It was classic Trump: Confident, hyperbolic and insistent on asserting control.

But interviews with nearly two dozen aides, allies, and others close to the president paint a different picture – one of a White House on a collision course between Trump’s fixed habits and his growing realization that this job is harder than he imagined when he won the election on Nov. 8.

So far, Trump has led a White House gripped by paranoia and insecurity, paralyzed by internal jockeying for power. Mistrust between aides runs so deep that many now employ their own personal P.R. advisers — in part to ensure their own narratives get out. Trump himself has been deeply engaged with media figures, even huddling in the Oval Office with Matt Drudge.

Trump remains reliant as ever on his children and longtime friends for counsel. White House staff have learned to cater to the president’s image obsession by presenting decisions in terms of how they’ll play in the press. Among his first reads in the morning is still the New York Post. When Trump feels like playing golf, he does — at courses he owns. When Trump feels like eating out, he does — at hotels with his name on the outside.

As president, Trump has repeatedly reminded his audiences, both public and private, about his longshot electoral victory. That unexpected win gave him and his closest advisers the false sense that governing would be as easy to master as running a successful campaign turned out to be. It was a rookie mistake. From the indignity of judges halting multiple executive orders on immigration-related matters—most recently this week—to his responses to repeated episodes of North Korean belligerence, it’s all been more complicated than Trump had been prepared to believe...

As he sat in the Oval Office last week, Trump seemed to concede that even having risen to fame through real estate and entertainment, the presidency represented something very different.

“Making business decisions and buying buildings don’t involve heart,” he said. “This involves heart. These are heavy decisions.”

When Donald Trump gets angry, he fumes. “You can’t make them happy,” he said. “These people want more and more.”

He was complaining to friends that he had negotiated for weeks with Freedom Caucus members and he couldn’t believe the group was still against the health care legislation. Trump and his advisers were buzzing about making an enemies list and wanted to force a vote. But it was Trump, a man who hates to show weakness, who had to blink. As support flagged, the bill was shelved.

“I kind of pooh-poohed the experience stuff when I first got here,” one White House official said of these early months. “But this shit is hard.”

The [health care] defeat represented an early inflection point for a president who is openly more transactional than ideological. More than anything, it reinforced the president’s conviction that he could only trust the tight circle of people closest to him.

Now, Trump is forging ahead alone on taxes, rolling out a dramatic package of tax cuts on Wednesday without input from Hill leaders. “We aren’t listening to anyone else on taxes,” said one senior administration official, referring to Ryan. “It’s our plan.”

As Trump is beginning to better understand the challenges—and the limits—of the presidency, his aides are understanding better how to manage perhaps the most improvisational and free-wheeling president in history. “If you’re an adviser to him, your job is to help him at the margins,” said one Trump confidante. “To talk him out of doing crazy things.”

Interviews with White House officials, friends of Trump, veterans of his campaign and lawmakers paint a picture of a White House that has been slow to adapt to the demands of the most powerful office on earth.

“Everyone is concerned that things are not running that well,” said one senior official. “There should be more structure in place so we know who is working on what and who is responsible for what, instead of everyone freelancing on everything.”

But they’re learning. One key development: White House aides have figured out that it’s best not to present Trump with too many competing options when it comes to matters of policy or strategy. Instead, the way to win Trump over, they say, is to present him a single preferred course of action and then walk him through what the outcome could be – and especially how it will play in the press.

“You don’t walk in with a traditional presentation, like a binder or a PowerPoint. He doesn’t care. He doesn’t consume information that way,” said one senior administration official. “You go in and tell him the pros and cons, and what the media coverage is going to be like.”

Downplaying the downside risk of a decision can win out in the short term. But the risk is a presidential dressing-down—delivered in a yell. “You don’t want to be the person who sold him on something that turned out to be a bad idea,” the person said.

Advisers have tried to curtail Trump’s idle hours, hoping to prevent him from watching cable news or calling old friends and then tweeting about it. That only works during the workday, though—Trump’s evenings and weekends have remained largely his own.

“It’s not like the White House doesn’t have a plan to fill his time productively but at the end of the day he’s in charge of his schedule,” said one person close to the White House. “He does not like being managed.”

He also doesn’t like managing—or, rather, doesn’t mind stoking competition among his staffers. While his predecessor was known as “no-drama Obama,” Trump has presided over a series of melodramas involving his top aides, including Priebus, Bannon, counselor Kellyanne Conway and economic adviser Gary Cohn.

“He has always been a guy who loves the idea of being a royal surrounded by a court,” said Michael D’Antonio, one of Trump’s biographers.

Trump continues to crave attention and approval from news media figures. Trump huddled in the Oval Office with Matt Drudge, the reclusive operator of the influential Drudge Report, to talk about his administration and the site. Drudge and Kushner have also begun to communicate frequently, said people familiar with the conversations. Drudge, whose visits to the White House haven’t previously been reported, didn’t respond to a request for comment.

Several senior administration aides said Trump loves nothing more than talking to reporters – no matter what he says about the “failing” New York Times or CNN – and he often seems personally stung by negative coverage, cursing and yelling at the TV. Kushner, too, sometimes calls TV personalities and executives, in particular MSNBC host Joe Scarborough, according to people close to the Trump son-in-law. (It didn’t go unnoticed in the West Wing that, at the height of the Kushner-Bannon war, the Drudge Report and Scarborough’s Morning Joe had an anti-Bannon flair to their coverage.)

If the goal of most administrations has been to set the media agenda for the day, it’s often the reverse in Trump’s White House, where what the president hears on the cable morning gabfests on Fox News, MSNBC and CNN can redirect his attention, schedule and agenda. The three TVs in the chief-of-staff's office sometimes dictate the 8 a.m. meeting – and are always turned on to cable news, West Wing officials say.

The fact that 100 days, as a marker, has no legal or actual significance outside the media has not seemed to matter to Trump. While he has publicly derided the deadline as “ridiculous” on Twitter, he has decidedly reshuffled his schedule, priorities and agenda in the last two weeks to notch political points, knowing the deadline would get inordinate media coverage.

He has repeatedly pressed aides to have a health care vote before Saturday. He surprised his own staff by promising a tax reform plan by this week and urged them to round out his list of accomplishments. He has maintained an aggressive calendar, wooing conservative outlets and traditional reporters alike.

He told aides this week needed to be a busy one — just as he told them after his inauguration.

In days 1 through 10, it was executive orders on a federal hiring freeze, abortions abroad, withdrawing from an Asian trade deal and the explosive immigration order barring immigrants from certain Muslim-majority countries. He got into a diplomatic row with Australia, one of America’s closest allies. The immigration order sparked international protests and was stopped in court. Trump later told advisers he regretted how it was handled.

In days 90 through 100, it was a flurry of executive orders. He got into a diplomatic row with Canada, one of America’s closest allies, threatening a trade war. He moved toward unwinding NAFTA. “There is no way we can do everything he wants to do this week,” one senior official said.

“Trump is a guy of action. He likes to move,” said Chris Ruddy, a close friend. “He doesn’t necessarily worry about all the collateral damage or the consequences.”