A Promised Land

“I experienced failure and learned to buck up so I could rally those who’d put their trust in me. I suffered rejections and insults often enough to stop fearing them. In other words, I grew up—and got my sense of humor back.” 

This passage emphasizes the resilience Obama developed after graduating from Columbia University and taking a job as a community organizer in Chicago. The work entailed asking strangers for help on various projects, such as after-school programs and asbestos removal. Obama genuinely cared for the community he was helping, which kept him motivated even in the face of rejection. Obama drew on this tenacity throughout his political career, working to solve problems even in the face of major obstacles.

“I’d never once heard her dwell on the disappointments. Instead she seemed to find small pleasures everywhere. Until this.” 

This quote is about Obama’s mother, who maintained a positive attitude even through life’s challenges. Dunham remained joyful despite being twice divorced, raising two children on her own, and suffering financial hardships. Her demeaner changed after she was diagnosed with uterine cancer, a disease that left her so weak her saliva glands shut down. Dunham had a profound impact on Obama, even during her illness. Toward the end of her life, she encouraged Obama to pursue a seat in the Illinois State Senate, but only if he had Michelle’s support.

“The truth is, I’ve never been a big believer in destiny. I worry that it encourages resignation in the down-and-out and complacency among the powerful.”

People often tell Obama they knew he would be president the moment they met him. They present their assertions in religious terms, claiming that God had a plan for him. However, Obama was not a strong believer in destiny. Further, at no point did he think the presidency was a foregone conclusion. Had he known, he would have saved himself a lot of self-doubt and anxiety. 

“When asked a question, I tended to offer circuitous and ponderous answers, my mind instinctively breaking up every issue into a pile of components and subcomponents. If every argument had two sides, I usually came up with four. If there was an exception to some statement I just made, I wouldn’t just point it out; I’d provide footnotes. ‘You’re burying the lede!’ Axe would practically shout after listening to me drone on and on and on. For a day or two I’d obediently focus on brevity, only to suddenly find myself unable to resist a ten-minute explanation of the nuances of trade policy or the pace of Arctic melting. ‘What d’ya think?’ I’d say, pleased with my thoroughness as I walked offstage. ‘You got an A on the quiz,’ Axe would reply. ‘No votes, though.’” 

This passage describes a key aspect of Obama’s personality: his tendency to speak slowly and circuitously. This style of speech works well in some contexts, such as academia, but not in political debates. The most effective debate answers are not those that illuminate, but rather, that evoke an emotional response, identify an enemy, or signal loyalty to a constituency. The fact that Obama is a deliberate speaker, however, kept his gaffe quotient relatively low during presidential debates.

“I’ve often been asked about this personality trait—my ability to maintain composure in the middle of crisis. Sometimes I’ll say that it’s just a matter of temperament, or a consequence of being raised in Hawaii, since it’s hard to get stressed when it’s eighty degrees and sunny and you’re five minutes from the beach. If I’m talking to a group of young people, I’ll describe how over time I’ve trained myself to take the long view, about how important it is to stay focused on your goals rather than getting hung up on the daily ups and downs.” 

Obama describes his ability to remain calm under pressure after losing the New Hampshire primary to Clinton. His composure and air of optimism helped carry his team through the loss. Obama claims he inherited this trait from his maternal grandmother, who grew up in Kansas during the Depression. Her calm, tenacious personality allowed her to rise from an entry-level clerical position at the Bank of Hawaii to one of its first female vice presidents. 

“There is not a Black America and a white America and a Latino America and an Asian America. There’s the United States of America.” 

This quote comes from Obama’s 2004 Democratic Convention speech. The words are aspirational, rather than an accurate description of the country. Obama stressed that commonalities matter more than differences throughout his time in public office. However, he was also attuned to various forms of inequality and sought to effect changes to make the nation a more just place. Achieving this goal meant building coalitions across different racial and ethnic lines. 

“While there are moments in politics, as in life, when avoidance, if not retreat, is the better part of valor, there are other times when the only option is to steel yourself and go for broke.” 

Obama downplayed race during his campaign for the Democratic nomination because he did not want to divide the electorate along racial lines. Reverend Wright’s controversial comments denouncing the US as a racist country, however, demanded a direct response. Obama gave a speech at the National Constitution Center in Philadelphia about racial divisions and urged Americans to recognize each other’s realities. This shift in strategy paid off. Networks carried the speech live, over a million people watched it online within 24 hours, and Obama received strong reviews.

“The responsibility of tackling these problems didn’t scare me. In fact, I relished the chance. But from everything I was learning, things were likely to get significantly worse before they got better.” 

This passage exemplifies Obama’s commitment to solving the nation’s problems, even the most challenging ones. The economy worsened during Obama’s presidential campaign. Despite the passage of TARP, the financial system was in peril, the housing market was crashing, and jobs were rapidly disappearing. Experts speculated that the country’s three big automakers, General Motors, Fiat Chrysler, and Ford, would soon be in jeopardy. Although Obama was determined to resolve the economic crisis, he questioned how quickly it could be done and worried about the impact a long recovery would have on the American people.

“‘It went fine for us,’ I said. ‘But based on what I just saw, we better win this thing or the country is screwed.’” 

Obama spoke these jarring words after an emergency meeting in the Cabinet Room of the White House. Bush met with Obama, McCain, and senior Republicans and Democrats to discuss the TARP legislation. Despite its unpopularity, Obama voiced his support for TARP, laying out its strengths and pointing out areas that still needed addressing, such as homeowner relief compensation. Obama assured Bush that Democrats would put country over party and help pass the bill. When Bush called on McCain to speak, the Senator deferred to the other Republicans in the room. Obama pressed the issue later in the meeting, telling Bush he wanted to hear what McCain had to say. It became clear to everyone that McCain did not have a plan for economic recovery. At that moment, winning became an even bigger imperative for Obama. The country was depending on him.

“I would never fully rid myself of the sense of reverence I felt whenever I walked into the Oval Office, the feeling that I had entered not an office but a sanctum of democracy. Day after day, its light comforted and fortified me, reminding me of the privilege of my burdens and my duties.” 

The reverence Obama has for the Oval Office reflects the seriousness with which he took his responsibilities as POTUS. Although Obama grew comfortable enough to put his feet up on the desk and steal a nap on the couch, the Oval remained a powerful emblem of democracy and an ever-present reminder of his oath.

“‘When things are bad,’ Axe said, walking next to me as we left the December meeting, ‘no one cares that things could have been worse.’” 

Obama made unpopular decisions in response to the financial crisis. Following Keynesian economic theory, he compensated for cuts in private spending with massive increases in public spending. Obama and his team knew these drastic measures would only mitigate, not eliminate, economic hardship. In this no-win situation, the best they could do was temper the public’s expectations.

“No matter what you might tell yourself, no matter how much you’ve read or how many briefings you’ve received, or how many veterans of previous administrations you’ve recruited, nothing entirely prepares you for those first weeks in the White House.”

This quote describes Obama’s initial reaction to living and working in the White House. One of his goals with the memoir is shed light on the American political process and provide readers with a sense of what it is like to be POTUS. To this end, he provides a vivid account of his first weeks in office, describing the good, the bad, and everything in between.

“I hadn’t run simply to fan anger and allocate blame. I had run to rebuild the American people’s trust—not just in the government but in one another.”

Obama sought to restore the public’s trust in the government. For years, conservative media outlets and think tanks financed by the ultra-rich fueled resentment by promoting anti-government messages. The government, they claimed, was taking money, jobs, and college slots away from hardworking Americans. Worse, the government was giving these things to lazy people with problems of their own making. Obama aimed to counter this divisive rhetoric by fostering a sense of common purpose and restoring faith in the government’s capacity to do good. The economic crisis complicated this task by making people angrier, more fearful, and more convinced than ever that the system was rigged. 

“To see ordinary people sloughing off fear and habit to act on their deepest beliefs, to see young people risking everything just to have a say in their own lives, to try to strip the world of the old cruelties, hierarchies, divisions, falsehoods, and injustices that cramped the human spirit–that, I had realized, was what I believed in and longed to be a part of.” 

Obama’s overarching aim as POTUS was to make the US a safer place. To this end, he worked with the global community to curb Iran’s nuclear program. He drew inspiration from the past, in particular, from those who fought injustice and worked to improve the world at great personal risk. The solitary man who faced a government tank in Tiananmen Square in 1989 was equally inspiring to Obama as the American civil rights activists who marched in Selma in the 1960s. 

“But I also realized that around the world, in places like Yemen and Afghanistan, Pakistan and Iraq, the lives of millions of young men like those three dead Somalis (some of them boys, really, since the oldest pirate was believed to be nineteen) had been warped and stunted by desperation, ignorance, dreams of religious glory, the violence of their surroundings, or the schemes of older men. They were dangerous, these young men, often deliberately and casually cruel. Still, in the aggregate, at least, I wanted somehow to save them–send them to school, give them a trade, drain them of the hate that had been filling their heads. And yet the world they were a part of, and the machinery I commanded, more often had me killing them instead.” 

A key aspect of Obama’s personality is his ability to empathize. In this passage he describes empathizing even with those who break laws and show cruelty to others. His duty as POTUS, however, supersedes his impulse to save young radicalized men. His handling of the Maersk Alabama hijacking is a case in point. Three teenaged Somali pirates hijacked the container ship and kidnapped its American captain. On Obama’s orders, SEAL snipers killed the hostage takers and rescued the captain, who escaped uninjured. 

“Sometimes your most important work involved the stuff nobody noticed.” 

Good presidential decisions do not necessarily result in accolades. Some of Obama’s most consequential decisions never entered the public consciousness. A salient example is his handling of the H1N1 pandemic, which involved incentivizing drug makers to quicken vaccine production and distributing medical supplies across the country. The virus proved less deadly than experts feared. Thus, Obama’s efforts received little press coverage. 

“Tamping down my emotions as the justice spoke to the audience, I looked over at a pair of handsome young Korean American boys—Sotomayor’s adopted nephews—squirming in their Sunday best. They would take for granted that their aunt was on the U.S. Supreme Court, shaping the life of a nation—as would kids across the country. Which was fine. That’s what progress looks like.” 

Obama’s nomination of Sotomayor to the Supreme Court is among his most significant acts as president. Sotomayor is the first Latina, and only the third woman, to serve on the Supreme Court. Thus, she is both a groundbreaker and a positive role model for young people, in particular minorities.

“Should I tell the thirty million people who can’t get covered that they’re going to have to wait another ten years because we can’t get them a public option?” 

This passage underscores the importance of compromise. Activists on the Left criticized Obama for compromising on healthcare reform. These critics were upset about the lack of a public option in the final version of the ACA. As Obama points out, however, some progress on healthcare reform is better than no progress. The public option was removed from the Senate bill because there was no way it would pass. Obama approached other issues in a similar manner. Indeed, a key aspect of his leadership style was arriving at consensus through compromise.

“To be known. To be heard. To have one’s unique identity recognized and seen as worthy. It was a universal human desire, I thought, as true for nations and peoples as it was for individuals.”

This quote describes Obama’s approach to diplomacy and foreign policy. Throughout his presidency, Obama made a point of showing interest in the history and culture of the places he visited. He also included high-profile sightseeing into his trips, as well as town halls with young people. This show of interest improved perceptions of the US around the world. 

“Turns out avoiding a war is harder than getting into one.” 

Obama describes myriad conflicts that had the potential to turn violent. Iran’s nuclear facility in a mountain near Qom sparked outrage at home and abroad. Congress, Sarkozy, and Brown called for a strong international response in the form of sanctions. However, China was keen to avoid casting sanctions against one of its main oil suppliers, and Russia was a longtime ally of Iran. Obama had to a balance his goals with those of other countries without sparking a third world war.

“It's in the nature of politics, and certainly the presidency, to go through rough patches—times when, because of a boneheaded mistake, an unforeseen circumstance, a sound but unpopular decision, or a failure to communicate, the headlines turn sour and the public finds you wanting. Usually this lasts for a couple of weeks, maybe a month, before the press loses interest in smacking you around, either because you fixed the problem, or you expressed contrition, or you chalked up a win, or something deemed more important pushes you off the front page.” 

The press has the power to sway public opinion. Bad press usually passes after a few weeks, but Obama experienced near-constant bad press for his first two years in office. The economic crash and unpopular bills kept his name in the headlines, as did the country’s ongoing wars in Iraq and Afghanistan. The BP oil spill exacerbated the situation, despite being out of Obama’s control. When the accident first occurred, the public placed the blame squarely on BP. However, as the months passed and oil gushed into the Gulf of Mexico, the public shifted the blame onto Obama.

“I sometimes ponder the age-old question of how much difference the particular characteristics of individual leaders make in the sweep of history—whether those of us who rise to power are mere conduits for the deep, relentless currents of the times or whether we're at least partly the authors of what's to come.” 

This quote addresses the possibilities and constraints of being president. Obama embarked on his presidential campaign with overarching goals, notably, a desire to reform healthcare and the broken immigration system. However, he spent much of his time in office addressing issues he inherited, such as the financial crisis and the wars in Iraq and Afghanistan. Unexpected problems like the BP oil spill also occupied his time. Further, he faced Republican obstructionism at every turn. In short, Obama’s legacy was influenced, and in some cases determined, by factors outside his control. 

“What I hadn’t anticipated was the media’s reaction to Trump’s sudden embrace of birtherism—the degree to which the line between news and entertainment had become so blurred, and the competition for ratings so fierce, that outlets eagerly lined up to offer a platform for a baseless claim.” 

The lie that Obama was not born in the US received new life because of Trump. Fake news proliferated during Obama’s first term, both online and through traditional media outlets, where coverage of the birther conspiracy resulted in higher ratings.