A Promised Land by Barack Obama Summary

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A Promised Land by Barack Obama

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My Thoughts

In writing this memoir, Obama said that his first and foremost goal for the book is “…to provide an honest rendering of my time in office. To offer readers a glimpse at what it’s like to be the president of the United States.” I think he did a good job of giving a glimpse at what it was like to be the president. He included a variety of details small and big, from how his clothes were neatly pressed and folded every night by the staff, to the processes behind making strategic decisions about the economy, troop deployments, and many other critical areas.

Even at 29 hours long the time goes by fast. It ends abruptly in the second half of his first term and I’m looking forward to reading the remainder of his memoirs. Like Greenlights, the audio version is read by the author which makes listening more intimate.

My Favorite Quotes

  • Enthusiasm makes up for a host of deficiencies.
  • The power to inspire is rare.
  • You don’t choose the time, the time chooses you.
  • People are moved by emotion, not facts.
  • It is important to take the long view. To stay focused on your goals rather than getting hung up on the daily ups and downs.
  • There is a direct link between doing your work and having your wishes come true.
  • No problem that lands on the president’s desk has a clean one-hundred percent solution.
  • Most presidents labor without knowing the economic impact of their actions.
  • The absence of catastrophe, and the preservation of normalcy, do not attract attention.
  • Having at least one contrarian in the room makes us think harder about the issues.
  • Sometimes your most important work involves the stuff nobody notices.
  • Resolve without foresight is worse than useless.
  • To be known, to be heard, and to have one’s unique identity recognized and seen as worthy is a universal human desire.
  • Getting things done means subjecting yourself to criticism. The alternative, playing it safe and avoiding controversy, is a recipe for mediocrity.

Key Questions

  • What kind of person do you want to be?

Key People

Because my list of key people from the book is a lot longer than for most books, I’ve moved it to the end of the summary. Here is my list of key people from A Promised Land.


His first and foremost goal for the book is to provide an honest rendering of his time in office. To offer readers a glimpse at what it’s like to be the president of the United States.

Only by hitching his wagon to something larger than himself was he able to locate a community and purpose for his life.

Part One: The Bet

Chapter 1

There are people in the world that only care about themselves. Then there are people who do the opposite and care about others. Which kind of person do you want to be? (A lesson from his mother)

He found refuge in books. He read a lot of books, all the time. He went to rummage sales looking for books. He developed a reading habit as a child. This was instilled by his mother. She would encourage him to “go read a book, then come back and tell me something you learned.”

Most of what he read, he only understood dimly. When reading, he would circle any unfamiliar words to look up. He was confident that it would prove handy once he figured out his calling.

For three years at college, he lived like a monk. He did a lot of reading, writing, and filling up journals.

At age 22, there was a wide gap between his grand ambitions and anything he was actually doing in life. He realized his vision of accomplishing great things was absurd. He was deeply self-conscious, sensitive to rejection, and maybe even had a fundamental laziness. He purged the softness from his life and developed a regimen of self-improvement that he has never entirely shed. He started working out, made lists, went for runs, ate healthy, and stripped himself of excess belongings.

When he graduated college in 1983 he had big ideas and nowhere to go. He got into community organizing and took a position in Chicago working with a group of churches trying to help the community.

The city of Chicago changed the arc of his life. It got him out of his head. He had to listen to what mattered to people. He experienced rejections and insults often enough to stop fearing them.

He left community organizing because he saw the work as too slow. It was too limited and not able to match the needs of the people he hoped to serve.

He was inspired by Harold Washington, the first African American to be elected as the mayor of Chicago. He gave people hope. He made you feel like anything was possible. This planted the seed that he might one day run for public office.

Enthusiasm makes up for a host of deficiencies.

Chapter 2

In 1995 he decided to run for Illinois State Senate when Alice Palmer vacated her seat, he was elected in 1996 and served until 2004.

He was not good at speaking initially. His speeches were stiff, heavy with policy, and short on inspiration and humor. He slowly got better and the ranks of his supporters grew.

During his first campaign he learned to respect the nuts and bolts of politics, the attention to detail required, and the daily grind that might be the difference between winning and losing.

For eight years he drove several hours to Springfield for senate meetings. He would listen to audio books during the drive. He liked longer books. John le Carré, and Toni Morrison were some of his favorite authors. He also liked listening to books about history.

Politics in Springfield was a series of transactions that were mostly hidden from view. What politicians in Springfield understood was that 90% of the time, voters back home were not paying attention.

In 2000 he lost the Democratic primary race for congress. He was in a dark mood after losing. He was almost 40, broke, had a strained marriage, and was coming off a humiliating defeat. Worst of all, in running for Congress he was driven not by a selfless dream of changing the world. Rather he was driven by the need to justify the choices he had already made, or to satisfy his ego, or to quell his envy of those who had achieved what he had not.

Chapter 3

To really shake things up, he needed to speak to and for the widest possible audience. The best way to do that was to run for a statewide office, like the US Senate.

Over time he learned to focus more on listening instead of speaking. The more he listened, the more people opened up.

He was invited to speak at the DNC in July 2004. Prior to the speech, he practiced for the first time on a teleprompter with his coach, Michael Sheehan. This was his first time speaking to a national audience.

Here is a video of that speech.

He took only seven days off during the 18 months prior to his election as senator.

As a senator his goal was to be a workhorse, not a show-horse.

One feature of the senate that excited him was that it gave him the ability to influence foreign policy. He was particularly interested in nuclear non-proliferation. After his election as senator, he wrote to Richard Lugar letting him know he hoped to work with him on these issues. He ended up taking his first foreign trip as a senator with Dick Lugar. Obama said the trip was invigorating and a reminder of how big the world is.

As senator he had Jon Favreau as his speechwriter, Pete Rouse as Chief of Staff, and hired Chef Sam Kass as a personal chef for his family. He recruited a team of highly qualified advisers to help him, among others this included a policy director, communications director, and more.

Chapter 4

This chapter is primarily about his struggle with the decision of whether or not to run for president. It was interesting to hear his perspective of how this was unexpectedly thrust upon him by the media and many others asking if he was going to run for president.

This was advice given by Ted Kennedy when he was contemplating running for president: the power to inspire is rare. Moments like this are rare. You don’t choose the time, the time chooses you. You either seize what may be the only chance you have, or be willing to live with the knowledge that the chance has passed you by.

Obama selected David Plouffe as his campaign manager, and David Axelrod as his chief strategist.

Part Two: Yes We Can

Chapter 5

The minute you announce your candidacy for president, the normal rules of speech no longer apply. Every word coming out of your mouth is recorded, amplified, scrutinized, and dissected.

Reggie Love, his body man, and Marvin Nicholson were his caretakers and anchors to normalcy during his campaign.

Obama’s initial problem during campaigning was his inability to boil issues down to their essence and tell a story. He was often too long-winded with his answers and worked on improving this. His tendency to give complicated answers often worked against him, especially during the debates.

David Axelrod told Obama that his problem in the debates was that he kept trying to answer the question. The point is not to answer the question. The point is to get your message across, your values and priorities. Give one line to seem like you answered the question and then talk about what you want to talk about.

Like it or not, people are moved by emotion, not facts. His job was to elicit the best of people’s emotions.

The main focus of the early campaign was to focus on winning Iowa which was the first state to vote in the primary election. They opened offices to cover all 99 counties and hired a young staffer to run each office with little pay or oversight. They deployed over 200 field organizers across the state. Obama spent 87 days in Iowa in 2007.

In Obama’s opinion, Washington was getting things wrong often by taking military action without first testing diplomatic options and also by observing diplomatic niceties to maintain the status-quo when action was needed.

The night of his speech at the Iowa Jefferson Jackson Dinner was when he became convinced that they would win Iowa, and by extension, the democratic nomination for president.

Chapter 6

I didn’t take a lot of notes on chapter 6 but I really like this piece of advice that he gave.

It is important to take the long view. To stay focused on your goals rather than getting hung up on the daily ups and downs.

Chapter 7

He had over 1,000 people on his campaign staff during the primaries.

The number of threats Obama received exceeded anything the secret service had ever seen during the primaries, so he was given secret service protection earlier than normal for a candidate.

The one big tactical error of his campaign was trying to win both Ohio and Texas at the same time. In retrospect he would have set more realistic expectations and conceded Ohio in order to concentrate all of their efforts on winning Texas. They ended up losing Ohio decisively and Texas just barely.

There are times in life when avoidance, or retreat, is the better part of valor. But there are other times when the only option is to steel yourself and go for broke.

Chapter 8

Was I prepared to be a world leader?

During his campaign, he felt the immensity of the challenges that awaited him if he won the election, and realized the grace he would need to do the job.

When he visited the Western Wall in Jerusalem in July of 2008, he wrote the following prayer to God and placed it inside a crack in the wall.

“Lord — Protect my family and me. Forgive me my sins, and help me guard against pride and despair. Give me the wisdom to do what is right and just. And make me an instrument of your will.”

Obama’s Prayer at the Western Wall in Jerusalem

While campaigning he would talk to his children every night when he was on the road. If he was home, he would read to them, challenge them to board games, and sneak out with them to get ice cream.

He knew that he would never get the missed time with his children back. He often found himself questioning the wisdom of trading time with his children in order to be president.

After winning the Democratic nomination for president, the single biggest decision he had to make was selecting his running mate. He had narrowed his choices to Tim Kaine and Joe Biden. In this section, he explains the pros and cons of each choice and his decision-making process in selecting Biden.

Chapter 9

George Haywood was the first person to warn Obama about the looming crash of the housing market and the financial system.

Obama began consulting with his in-house economic advisors Austan Goolsbee, and Jason Furman. He also put together an ad hoc advisory group consisting of Paul Volcker, Larry Summers, and Warren Buffett, they had all lived through major financial crises before. He said their briefings proved invaluable in helping him understand the nuts and bolts of the crisis, and evaluate the various responses being proposed.

He spent three days doing debate preparation for the presidential debate. His team recruited a pair of lawyers and political veterans, Ron Klain, and Tom Donilon to work with him. They gave him a detailed breakdown of the debate format and an outline of every conceivable question that might be asked. They, along with Axelrod, Plouffe, Anita Dunn, and the rest of the team, drilled Obama for hours on the precise answers they wanted to hear. They honed down to the last word or turn of phrase that he was to use.

They built an exact replica of the debate stage on which to practice. During the first night of preparation they did a full 90-minute mock debate. They picked apart every aspect of his performance including pace, posture, and tone. It was exhausting but useful.

“There is a direct link between doing your work and having your wishes come true.” Was a statement that his mom would frequently remind him of.

Obama was particular about his debate day rituals. On debate days, his schedule usually looked like this.

  • Morning: devoted to going over strategy and key points
  • Early afternoon: light campaigning
  • Schedule cleared by 4:00 pm
  • Quick workout to shed excess adrenaline
  • Shave and take a long hot shower 90 minutes before leaving for the debate venue
  • Put on a new shirt (white) and tie (blue or red) that his body man had hung in his hotel closet beside his freshly pressed blue suit
  • Dinner: comfort food. Steak cooked medium well, roasted or mashed potatoes, and steamed broccoli.
  • 30 minutes before debate: glance at notes and listen to music.

He eventually became compulsive about listening to a few specific songs before a debate. Freddie Freeloader by Miles Davis, My Favorite Things by John Coltrane, and Luck be a Lady by Frank Sinatra. Ultimately, it was rap that got his head in the right place. Two songs especially, My First Song by Jay-Z and Lose Yourself by Eminem. Both songs are about defying the odds and putting it all on the line.

Part Three: Renegade

Chapter 10

In the modern White House, the Chief of Staff is the day to day quarterback. The end of the funnel through which every issue facing the president had to first pass. Few in government, including the president, work longer hours or under more unrelenting pressure. His first and best choice for Chief of Staff was Rahm Emanuel. Rahm eventually accepted the position.

Prior to his announcement as president, he closed his eyes and summoned the prayer that carried him to that point. It was a prayer that he repeated every night that he was the president. It was a prayer of thanks for all he had been given, that his sins would be forgiven, that his family and the American people would be kept safe from harm, and a prayer for guidance.

Chapter 11

In the days leading up to the inauguration, Obama read several books on FDR‘s first term and the implementation of the New Deal.

Two weeks before his inauguration, Obama and Biden travelled to the capitol to meet with Harry Reid (Senate Majority Leader), Mitch McConnell (Senate Republican Leader), Nancy Pelosi (Speaker of the House), and John Boehner (House Republican Leader) to discuss what would eventually become the American Recovery and Reinvestment Act.

They often referred to these leaders as “The Four Tops.” For most of the next eight years, the dynamics among these individuals would play a key role in shaping Obama’s presidency.

He had read a lot about the previous presidents. He makes references to things done by Roosevelt, FDR, Truman, and many others throughout the book.

Most of his contact with the outside world depended on three aides who sat in the outside oval office. They were Reggie Love (his body man), Brian Mosteller, and Katie Johnson. They were his unofficial gatekeepers and life support system.

The First Family pays out of pocket for any new furniture in the White House, and for anything else it consumes from groceries to toilet paper, as well as extra staff for private dinner parties. This does not include the Oval Office, the White House budget has funds set aside for a new president to redecorate the Oval Office.

On his first full day in the White House, Obama walked through his closet to find every shirt, suit, and pair of pants he owned perfectly pressed and hung in orderly rows. His shoes were shined to a high-gloss, every pair of socks and shorts were folded and sorted like a department store display.

The main emotion Obama felt after the passing of the American Recovery and Reinvestment Act in 2009 was not triumph, but deep relief. They still had three or four big moves to make in order to end the crisis.

Chapter 12

Almost every night of the week he would plant himself in his chair after dinner to read and study. These were often the quietest and most productive hours of his day. He would pour over stacks of material that his staff sent over for review.

Material he would review nightly included:

  • The latest economic data
  • Decision memos
  • Informational memos
  • Intelligence briefings
  • Legislative proposals
  • Drafts of speeches
  • Press conference talking points
  • Letters from constituents

He requested to receive a nightly batch of ten letters from constituents. These were often the last thing he looked at before going to bed. This was his idea, he thought it would be a good way to reach outside of his presidential bubble and hear directly from those he served. He insisted on seeing a representative cross-section of letters, not just happy talk letters from supporters.

After reading each letter he would write a note to his staff to see what could be done to help, or write a response. Days or weeks later he would receive a follow-up memo explaining the actions taken on their behalf.

Obama talks about a speech by Tim Geithner about the economic recovery early in his administration. The speech was a total bomb and they learned a lot of lessons about preparation and improving processes through this failure. Among the lessons learned was to pay careful attention to how you staff big projects, and to pay close attention to the details not just of substance, but also to stagecraft.

“On any given moment, on any given day, somebody somewhere is screwing up.” -Bob Gates

They went to work trying to minimize screw-ups. Obama made a point of sitting down with each member of his cabinet to go over strategic plans for their departments. He would push them to identify roadblocks and set priorities.

For every event, meeting, and policy rollout, 100 people or more might be working behind the scenes. Every document fact checked, every person vetted, every event planned to the minute, and every policy announcement carefully scrubbed to make sure it was achievable, affordable, and didn’t carry the risk of unforeseen consequences.


Efforts to stretch the boundaries of what a First Lady should or should not do carried some peril. In the early months of the presidency, Michelle took her time deciding how she would use her new office. She figured out how and where she might exert an influence, while carefully and strategically setting the tone for her work as First Lady. She consulted with Hillary Clinton and Laura Bush. She recruited a strong team of seasoned professionals around her.

Eventually Michelle decided to take on two causes that were personally meaningful to her. One was the alarming rise in child obesity rates, and second was the embarrassing lack of support for America’s military families.

Obama was home most of the time, on most days work came to him. Unless he was traveling, he made a point of being at the dinner table at 6:30 pm each night. Even when it meant he had to go back downstairs to the oval office later.

Barack, Michelle, and Sam Kass began their day in gym every morning Monday-Thursday. Cornell McClellan was their family’s personal trainer. That hour in the gym was one more zone of normalcy that they could share with friends that still called them by their first names.

Decision Making

No problem that lands on the president’s desk has a clean one-hundred percent solution. If it had, someone else down that chain of command would have solved it already.

In decision making, and problem solving, the president is constantly dealing with probabilities. For example, a 70% chance that a decision to do nothing would end in disaster, a 55% chance that one approach or the other might solve the problem, a 30% chance that whatever they chose won’t work at all, and a 15% that it would make the problem worse.

In these circumstances, chasing after the perfect solution leads to paralysis. On the other hand, going with your gut too often lets preconceived notions, or the path of least political resistance, guide a decision. Usually with cherry picked facts used to justify it.

For decision making Obama’s desire was to follow a sound process, which involved emptying his ego and really listening, and following the facts and logic as best as he could, and considering them alongside his goals and principles. By doing this, he realized that he could make tough decisions and still sleep easy at night.

A good decision making process meant that he could allow each member of the team to feel ownership of the decision. This led to better execution and less leaks of White House decisions to the press.

The Auto Industry

By the autumn of 2008, auto sales had plunged to their lowest level in more than a decade. GM and Chrysler were running out of cash, while Ford was in slightly better shape (you can read more about what Ford was doing during this time in my book summary of American Icon).

This section of chapter 12 talks a lot about the auto industry and the decision making process the Obama administration went through in deciding how and what they could do to help.

Even major White House initiatives do not tend to produce any measurable impact on GDP or unemployment rates for months or even years. As a result, most presidents labor without knowing the economic impact of their actions.

The absence of catastrophe, and the preservation of normalcy, do not attract attention.

The voices of the American people meant a lot to Obama. He enjoyed reading letters from people sharing how programs his administration started had helped them. Those letters sustained his spirit and beat back whispering doubts on late solitary nights.

Chapter 13

A president’s single most important job is to keep the American people safe.

This is a lesson that Obama was learning early in his first term. Leadership, particularly in the national security arena, was about more than executing well-reasoned policy. Awareness of custom and ritual mattered, symbols and protocol mattered, body language mattered. He even had a coach help him work on his salute.

At the start of each day he would find a leather binder waiting for him at the breakfast table, it contained the President’s Daily Brief (PDB). The PDB was usually 10-15 pages in length and was prepared overnight by the CIA and other intelligence agencies. Most of what he read did not require immediate response, the goal was to have a continuous up-to-date sense of all that was roiling in the world. If you search online you can find samples of the PDB given to past presidents.

On the military front, Obama’s immediate goal upon entering office was to review each aspect of our military strategy so that his team could take a thoughtful approach to what came next. The broad outlines of the US withdraw from Iraq had been settled previously, but they needed to work out the details and pace of the withdraw.

Having at least one contrarian in the room makes us think harder about the issues.

Obama told Gates (Secretary of Defense) that his first priority was to make sure the US agencies, both civilian and military, were aligned around a clearly defined mission and a coordinated strategy. Unless they established realistic and limited objectives, they were setting themselves up for failure.

The military campaign in Afghanistan did not have a clearly defined goal. Obama’s team came up with the following primary goal: “To disrupt, dismantle, and defeat Al-Qaeda in Pakistan and Afghanistan, and to prevent their return to either country in the future.”

In 2009, Bob Gates recommended that they replace the existing commander in Afghanistan with Stanley McChrystal. They asked him to provide a fresh top-to-bottom assessment of conditions there within 60 days. Along with recommendations for any changes in strategy, organization, or resourcing of coalition efforts.

Unique among world leaders, the US president travels fully equipped so as not to rely on another government’s services or security forces. An armada of beasts, security vehicles, ambulances, tactical teams, and marine-one helicopters (when necessary) are flown in on C-17 transport planes in advance and pre-positioned on the airport tarmac prior to the president’s arrival.

Part Four: The Good Fight

Chapter 14

Most of this chapter is about Obama’s first G20 summit. I didn’t take a lot of notes on this section but it was interesting.

Obama proposed that NATO prepare individualized defense plans for each of its members.

Obama reminded himself of the following. Every president feels saddled with the previous administration’s choices and mistakes. Ninety-percent of the job is navigating inherited problems and unanticipated crises. Only by doing this well enough, with discipline and purpose, can you get a real shot at shaping the future.

Obama said that Václav Havel had been a distant role model to him. Watching him maintain his moral compass after gaining power had helped convince Obama that it was possible to enter politics and come out with your soul in-tact.

Chapter 15

Obama told John Brennan that his job was “to help me protect this country in a way that is consistent with our values, and to make sure that everyone else is doing the same.”

Ben Rhodes helped him with speech writing in addition to Jon Favreau.

Our history has always been the sum total of the choices made, and the actions taken, by each individual man and woman.

Chapter 16

This chapter is mostly about the Affordable Care Act.

People don’t really think about the flaws in the healthcare system until somebody in their own family gets sick.

Looking back, Obama says it his hard to deny his overconfidence about how difficult it would be to pass the affordable care act.

Passing up a chance to help millions of people just because it might hurt his re-election prospects, was exactly the kind if myopic, self-preserving behavior he had vowed to reject.

The Obama administration modeled the ACA legislation based off of Governor Mitt Romney’s Massachusetts health care reform, which was commonly known as “Romneycare.” Obama was convinced that Romney’s model offered them the best chance of achieving the goal of universal coverage.

In June 2009, the WHO declared the first global pandemic in 40 years over the H1N1 virus.

Sometimes your most important work involves the stuff nobody notices. This is the nature of the presidency.

Chapter 17

In politics, the stories told are often as important as the substance achieved.

Disdain between the two chambers of Congress is a time-honored tradition in Washington, one that even transcends party lines. Senators generally consider house members to be impulsive, parochial, and ill-informed. While house members tend to view senators as long-winded, pompous, and ineffectual.

Obama took pride in having created a culture in his administration where they didn’t go looking for scapegoats when things went south.

Some things are more important than getting re-elected. – Tom Perriello. What Tom told Obama before the healthcare vote.

Part Five: The World as It Is

Chapter 18

Obama learned to shed excess fear for the sake of focus while trying not to get so relaxed that he made sloppy mistakes.

Obama found Bob Gates to be practical, even-keeled, and refreshingly blunt. He had the quiet confidence to both argue his case and occasionally change his mind. They recognized in each other a common work ethic and sense of duty.

Obama had a series of nine 2-3 hour meetings from September-November to evaluate General McChrystal’s new plan for Afghanistan.

McChrystal’s new plan for Afghanistan revolved around using a Counter-insurgency (COIN) plan. It was similar to the strategy General David Petraeus used in Iraq.

The expansive view of COIN that McChrystal imagined for Afghanistan not only went beyond what was needed to destroy Al-Qaeda, it also went beyond what was likely achievable during Obama’s term in the office (if it was achievable at all).

Resolve without foresight is worse than useless.

They all agreed that the objective “To disrupt, dismantle, and defeat Al-Qaeda in Pakistan and Afghanistan, and to prevent their return to either country in the future” was not realistic. They developed this new set of achievable objectives:

  • Reducing the level of Taliban activity so they didn’t threaten major population centers
  • Pushing President Hamid Karzai to reform a handful of key departments. Like the ministries of defense and finance. Rather than trying to get him to revamp the entire government.
  • Accelerating the training of local forces that would eventually allow the Afghan people to secure their own country

Obama worried that the number of troops being requested was driven by ideological and institutional concerns, rather than by the objectives they had set.

Although not a perfect plan, the hours of debate had made for a better plan. It forced them to refine America’s strategic objectives in Afghanistan in a way that prevented mission creep. It also established the utility of timetables for troop deployments in certain circumstances.

Chapter 19

To be known, to be heard, and to have one’s unique identity recognized and seen as worthy is a universal human desire. This is true for individuals and Nations.

Obama was learning another difficult lesson about the presidency. That his heart was now chained to strategic considerations and tactical analysis. His convictions subject to counterintuitive arguments. That, in the most powerful office on earth, he had less freedom to say what he meant and act on what he felt than he had as a Senator or an ordinary citizen.

Most of this chapter deals with Obama’s foreign relations. Specifically with Iran and Russia. It goes into detail on his first trip to Russia as president and his meetings with Putin and Dmitry Medvedev.

Chapter 20

While visiting China, Obama’s commerce secretary left his hotel room for a meeting. He forgot something and went back to his suite, he discovered two men in suits thumbing through the papers on his desk. Their brazenness verged on comedy.

The presidency changes your time horizons. Rarely do your efforts bear fruit right away. The scale of most problems coming across your desk is too big for that. The factors at play are too varied. You learn to measure progress in smaller steps. Each of which may take months to accomplish. You have to reconcile yourself to the knowledge that your ultimate goal (if ever achieved) may take a year or two, or even a full term, to realize.

Chapter 21

Even successful initiatives, well-executed and with the purest of intentions, usually harbored some hidden flaw or unanticipated consequence. Getting things done means subjecting yourself to criticism. The alternative, playing it safe and avoiding controversy, is a recipe for mediocrity (and a betrayal of the hopes of the citizens that put you in office).

Obama appointed Cass Sunstein as the Administrator of the Office of Information and Regulatory Affairs. Over the next three years, Cass and is small team worked to ensure that the regulations they proposed helped enough people to justify their costs. Obama also asked him to lead a thorough review of all existing Federal regulations, so that they could get rid of those that were unnecessary or obsolete.

Cass found old requirements that forced doctors and hospitals to spend over a billion dollars annually on paperwork requirements and administrative burdens. He also found a bizarre environmental regulation that classified milk as “oil” and subjected dairy farmers to annual costs in excess of one-hundred million dollars. He also found a pointless mandate imposed on truckers requiring them to spend 1.5 billion dollars in wasted time filling out forms after each run.

When done properly, ambitious regulatory standards can actually spur businesses to innovate. This was mentioned on the topic of the innovations that resulted from new energy efficiency regulations on appliances and fuel efficiency regulations on vehicles.

During a United Nations Assembly, the Chinese delegation and others were avoiding negotiating with Obama about a climate change agreement. The leaders of China, Brazil, India, and South Africa were holding a secret meeting to hide from Obama and wait out the event. Eventually, Obama’s security team found them. Subsequently, President Obama and Hillary Clinton crashed the meeting uninvited and began negotiations anyway. This was one of my favorite stories in the book.

There would always be a chasm between what Obama knew should be done to achieve a better world, and what in a day, week, or a year he found himself actually able to accomplish.

Part Six: In the Barrel

Chapter 22

It is in the nature of politics, and certainly the presidency, to go through rough patches. Times when the headlines turn sour and the public finds you wanting.

Besides managing the government and getting the facts right, the public often looks to the president to explain a difficult and often scary world.

FDR understood that to be effective, governance couldn’t be so antiseptic that it set aside the basic stuff of politics. You have to sell your program, reward supporters, punch back against opponents, and amplify the facts that help your cause while fudging the details that don’t.

The shift in Washington power shows up on the president’s calendar. Rahm and Jim Jones saw Obama almost every day. Only Hillary Clinton, Tim Geithner, and Robert Gates had standing meetings with him in the Oval Office. Everyone else had to fight to get on Obama’s schedule. They tried to have full cabinet meetings once a quarter. Washington is a town where proximity and access to the president is taken as a measure of clout.

Keeping up morale wasn’t something he could delegate. Obama tried to be generous in his praise and measure in his criticism. In meetings he made a point of eliciting everyone’s views, including those of more junior staff members.

One aspect of management that took him longer to learn that it should have was the need to pay closer attention to the experiences of women and people of color on the staff.

Obama has long believed that the more perspectives around a table, the better an organization performs. He took pride that they had recruited the most diverse cabinet in history.

Once you become president, people’s perceptions of you, even the perceptions of those who know you best, are inevitably shaped by the media.

Obstacles and struggles rarely shook him to the core. Instead, depression was most likely to creep up on him when he felt useless, without purpose, when he was wasting his time, or squandering opportunities. Even during his worst days as president, he never felt that way. The job just doesn’t allow for boredom or wasted time. He usually came away from problem-solving meetings with his team feeling energized.

The Obamas tried to have regular weekend get-togethers with their regular circle of friends. In addition, they began hosting small dinner parties in the residence every few months. They would invite artists, writers, scholars, business leaders, and others whose paths they crossed and wanted to know better.

A significant portion of this chapter discusses reforming Wall Street. It describes what was involved in the passing of the Dodd–Frank Wall Street Reform and Consumer Protection Act. Obama considered it a significant triumph and the most sweeping change to the rules governing America’s financial sector since the New Deal.

Chapter 23

The most of this chapter details the Deepwater Horizon oil spill and how President Obama and his team responded.

With most presidential trips, this point is not so much to gather new information but to communicate concern and resolve.

Due to coastal erosion, Louisiana was losing more than 10,000 acres of land every year (see this article on FactCheck.org for more info).

A president has no choice but to continually multi-task.

Because the existing team working on repairing the oil leak was not able to come up with effective and timely solutions for the repair, Obama enlisted Steven Chu (Secretary of Energy) to help. This ended up being one of the best decisions Obama made in addressing the Deepwater Horizon problem.

Historically, the party controlling the White House almost always loses congressional seats after its first two years in power.

Later in this chapter, Obama discusses General Stanley McChrystal’s resignation and the Rolling Stones article The Runaway General that was the catalyst. He explains his thought process and decision-making that went into the decision to accept the resignation.

Ultimately, Obama saw no way to apply a different set of rules to a four-star general than the rules that are applied to all other military personnel. In the military, the stakes are always higher. Any failure to act as part of a team or any individual mistake didn’t just result in embarrassment, people could die.

Civilian oversight of the military is a bedrock principle of our representative democracy. According to Obama, the comments made by General McChrystal threatened to erode that principle if not addressed appropriately.

“When they are yelling at me, I know they’re thinking of you.” – Eric Holder to Obama

After an ambitious first year in office, Obama did not have a lot of political capital left. What little remained, they were husbanding to try to get as many initiatives as they could through congress before the 2010 midterms.

Even on vacation, Obama started his day with the President’s Daily Brief.

Chapter 24

Obama wished that he had the foresight on his first day in office to tell Harry Reid and the rest of the Senate Democrats to revise the chamber rules and get rid of the Senate filibuster.

Obama appointed Bill Daley as his new Chief of Staff after Rahm resigned to run for Mayor of Chicago. Bill had a reputation as a pragmatic, effective deal-maker with strong relationships with both labor and the business community.

According to Obama, Prime Minister Manmohan Singh was the chief architect of India’s economic transformation.

Historically, Congressional ambitions tend to be low during the stretch between election day and the Christmas recess. In spite of this, Obama and his administration worked hard after the 2010 midterm elections to try to get key legislation passed. This chapter highlights many of the bills they tried to get through Congress, one of the most interesting being the DREAM Act (it didn’t pass in 2010).

In six weeks, they enacted 99 laws during the 6 week stretch during the 2010 “lame duck” session.

Part Seven: On the High Wire

Chapter 25

Chapter 25 talks a lot about politics and conflict in the middle-east countries. A lot of it centered on Obama’s attempts at negotiating peace in the region between Israel and Palestine.

Members of both US political parties worried about crossing the American Israel Public Affairs Committee (AIPAC). Which is a powerful bipartisan lobbying organization dedicated to ensuring unwavering US support for Israel. AIPAC’s clout could be brought on just about every congressional district in the US.

Obama describes in detail his attempts at negotiating peace with Benjamin Netanyahu the Prime Minister of Israel, and Mahmoud Abbas the President of the Palestinian National Authority.

Periodically Obama would invite the leaders of Jewish organizations or members of Congress to the White House to ensure them of their ironclad commitment to Israel’s security and the relationship between the US and Israel. Obama helped fund the eventual development of the Iron Dome missile defense system.

Obama said he often ponders how much difference the particular characteristics of individual leaders make in the sweep of history. Whether those who rise to power are mere conduits for the deep relentless currents of the times, or whether they are at least partly the authors of what is to come. He wonders whether their insecurities and hopes, childhood traumas, or memories of unexpected kindness carry as much force as any technological shift or socio-economic trend. He wonders if the peace talks would have turned out differently if each of the leaders involved had different personalities, backgrounds, or were in differing life stages.

Obama had a Presidential Study Directive (PSD) done to evaluate unrest in Arab countries. Obama used that directive to instruct the State Department, Pentagon, CIA, and other Government agencies to examine ways the United States could encourage meaningful political and economic reforms in the region to nudge those nations closer to the principles of open government.

The middle of chapter 25 talks about Mohamed Bouazizi and his self-immolation which was a catalyst for the Tunisian Revolution.

In 2010, protests (made up mostly of young people) began in many Arab countries including Algeria, Yemen, Jordan, and Oman. These were the first flickers of what became known as the Arab Spring.

When we are too insulated, we see what we want to see and hear what we want to hear. These were Obama’s thoughts about Hosni Mubarak, the President of Egypt.

Obama said that Mohammed bin Zayed (MBZ), the Crown Prince of Abu Dhabi was perhaps the savviest leader in the gulf. He was young, sophisticated, and close the Saudis. He called Obama to tell him that US statements about Egypt were being watched closely in the gulf and with increasing alarm.

Chapter 26

This chapter focuses on Libya and Muammar Gaddafi during the Arab Spring.

Prior to America’s starting airstrikes in Libya, Obama called Gadaffi and offered him one last chance to pull back his forces and respect the rights of Libyans to engage in peaceful protest. Gadaffi refused.

Due to technical issues in Brazil, Obama had to authorize the airstrikes from an insecure cell phone that belonged to one of his staff. I found this ironic and relatable and even the president has technical issues this basic (with phones) that his team was not able to resolve and he found an unconventional workaround.

Hillary Clinton sent US Diplomat Chris Stevens to Benghazi, Libya to act as a liaison to the governing council there. Chris is the Ambassador that died during the 2012 Benghazi Attack. There was a movie made about this attack as well as an excellent book 13 Hours: The Inside Account of What Really Happened in Benghazi if you want to learn more about this event.

Chapter 27

This chapter primarily focuses on the hunt to find Osama Bin Laden. There are a lot of details included about the planning and execution of Operation Neptune Spear.

In May 2009 Obama told a handful of advisors, including Rahm, Leon Panetta, and Tom Donilon that he wanted to make the hunt for Bin Laden a top priority. He told them he wanted to see a formal plan for how he would be found. Obama wanted a report on his desk every 30 days describing their progress. He also had it put into a presidential directive to make sure everyone was on the same page.

Obama viewed the elimination of Bin Laden as critical to his goal of reorienting America’s counterterrorism strategy. By losing our focus on the small band of terrorists who had planned and carried out the attacks on 9-11, and instead defining the threat as an open-ended all-encompassing war on terror, we had fallen into what Obama believed was a strategic trap.

When the CIA identified the compound in Pakistan with “the pacer” that had a probability of being Bin Laden, Obama asked Tom Donilon and John Brennan to begin examining what an attack on the compound would look like.

They ended up with two options. Option one was to demolish it with an airstrike. The second option was to authorize a special ops mission. To preserve the secrecy of the operation, and deniability if something went wrong, the mission would be conducted under the authority of the CIA rather than the Pentagon.

They invited Vice Admiral William McRaven, the head of JSOC, to walk them through what the raid might entail.

The chain of command for the operation went from President Obama to Leon Panetta, then to William McRaven. McRaven was given complete authority to design and conduct the mission if they decided to go forward with it.

Notes on William McRaven. For his postgraduate thesis, he wrote The Theory of Special Operations. His thesis demonstrates how smaller special operations forces can achieve relative superiority. He defines relative superiority as the condition that exists when a smaller force gains a decisive advantage over a larger or well-defended enemy. I’ve also written a summary of Make Your Bed, one of McRaven’s books.

For planning purposes, the CIA had built a small 3D model of the compound. McRaven oversaw the construction of a full-scale replica of the compound at Fort Bragg. The SEAL team conducted a series of dress rehearsals at this compound to perfect the timing and planning of the operation.

To make sure the plan was pressure tested, they asked the National Counterterrorism Center to have their analysts pour over the available intelligence to see how their conclusions matched up.

While he couldn’t guarantee the outcome of his decision, Obama was fully prepared and fully confident in making it.

So much of what really matters in government comes down to the daily unheralded acts of people who aren’t seeking attention, but simply know what they are doing and do it with pride.

After the successful completion of the mission, Obama called George W. Bush and Bill Clinton to tell them the news. He made a point to acknowledge to Bush that the mission was the culmination of a long hard process begun under his presidency.

Obama called President Asif Ali Zardari of Pakistan to confirm the news. Obama expected this to be his most difficult call, but to his surprise he expressed congratulations and support.

Obama imaged what America might look like if we could rally the country so that our government brought the same level of expertise and determination to educating our children, or housing the homeless, as it had to catching Bin Landen.

He tells a brief story about a letter written to him by Payton Wall, meeting her at a 9-11 memorial, and helping her meet Justin Bieber.

Obama met with the team that successfully completed Operation Neptune Spear. He spent time with them and presented them with the Presidential Unit Citation, the highest award a military unit can receive.

The book ended at this point in the middle of Obama’s first term, around May 2011.

Key People

This is not an exhaustive list of people mentioned in the book. A full list would be several pages long. My apologies to anyone not included in this list. These are just some that stood out to me as being especially interesting, controversial, or that were mentioned the most frequently.

Related Book Summaries

Hope you enjoyed this and got value from my notes.
This is the 11th book read in my 2021 reading list.
Here is a list of my book summaries.

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