A Promised Land

Authors(s): Barack Obama
Published: 2020

Overall Thoughts & Roadmap

An enjoyable (but long!) read that made me nostalgic about the Obama days... This book summary is divided into the following sections:

(1) 5 takeaways from the memoir
(2) Obama's journey
(2a) Deciding to run
(2b) Running for president
(2c) What the Obama administration did

(1) Five bits of wisdom from Obama

1. Align your quest for greatness with more selfless aims.

Growing up, Obama says he didn't want to be part of politics. He got the impression that politicians are people who want to look good rather than do good.

"With few exceptions, everything I observed about politicians seemed dubious: the blow-dried hair, the wolfish grins, the bromides and self-peddling on TV while behind closed doors they curried the favor of corporations and other monied interests. They were actors in a rigged game, I decided, and I wanted no part of it."

An important question he faces is: "How can you be in politics but not of it?" Once he gets on the bandwagon of running for Congress, he worries that he's in it for the wrong reasons.

"I recognized that in running for Congress I’d been driven not by some selfless dream of changing the world, but rather by the need to justify the choices I had already made, or to satisfy my ego, or to quell my envy of those who had achieved what I had not. In other words, I had become the very thing that, as a younger man, I had warned myself against. I had become a politician—and not a very good one at that."

He finds an answer to this question in Martin Luther King Jr's Sermon. One possible solution is "to align your quest for greatness with more selfless aims".

"I recalled a sermon by Dr. Martin Luther King, Jr., called “The Drum Major Instinct.” In it, he talks about how, deep down, we all want to be first, celebrated for our greatness; we all want "to lead the parade." He goes on to point out that such selfish impulses can be reconciled by aligning that quest for greatness with more selfless aims. You can strive to be first in service, first in love. For me, it seemed a satisfying way to square the circle when it came to one’s baser and higher instincts."

2. Politics can make decent people do seemingly indecent things. So try to understand the situation, rather than make judgements about the person.

Obama recounts multiple instances of being put at a disadvantage because of how his competitors tried to get ahead. For example, John McCain gave the impression to the press that he is the one who came up with the idea of pushing for a bi-partisan solution to the impending economic crisis (when in fact it was Obama who approached him with this idea). But this doesn't make them bad people. It's politics that make them do questionable things. Obama writes: "It was a testament to John McCain’s character, his fundamental decency, that anytime a supporter approached him spewing Palin-style rhetoric, he politely pushed back."

You can disagree with a person's politics and still acknowledge that they are a decent human being. Knowing the difference is important.

“I disagreed with just about every one of George W. Bush’s major policy decisions, but I’d come to like the man, finding him to be straightforward, disarming, and self-deprecating in his humor.”

On that note, recognize that you often have more in common with people than you think - even people you don't seem to see eye to eye with. On Dmitry Medvedev, he writes:

“Medvedev and I had more than a few things in common: Both of us had studied and taught law, gone on to marry and start families a few years later, dabbled in politics, and been helped along by older, cagier politicians. It made me wonder how much the differences between us could be explained by our respective characters and dispositions, and how much was merely the result of our different circumstances. Unlike him, I had the good fortune of having been born in a nation where political success hadn’t required me to ignore billion-dollar kickbacks or the blackmailing of political opponents.”

3. There often is no right answer. But you can still develop a process to find the best answer given the circumstances you're in.

In order to make tough decisions (see below for the list of problems the Obama administration faced), you need to make sure you have a process that ensures that the problem has been tackled from every angle and perspective. Although this process doesn't ensure that you've made the right decision (more often than not there isn't one right answer), it does ensure that you've most likely made the best one possible given your situation.

Most policy-problems don't have a clean or "right" solution - you are constantly dealing with probabilities.

“My emphasis on process was born of necessity. What I was quickly discovering about the presidency was that no problem that landed on my desk, foreign or domestic, had a clean, 100 percent solution. If it had, someone else down the chain of command would have solved it already. Instead, I was constantly dealing with probabilities: a 70 percent chance, say, that a decision to do nothing would end in disaster; a 55 percent chance that this approach versus that one might solve the problem (with a 0 percent chance that it would work out exactly as intended); a 30 percent chance that whatever we chose wouldn't work at all, along with a 15 percent chance that it would make the problem worse."

Since there is no "right" solution, you need a process to strike the balance between chasing after a perfect answer and picking answers that confirm your pre-existing beliefs.

"In such circumstances, chasing after the perfect solution led to paralysis. On the other hand, going with your gut too often meant letting preconceived notions or the path of least political resistance guide a decision—with cherry-picked facts used to justify it. But with a sound process—one in which I was able to empty out my ego and really listen, following the facts and logic as best I could and considering them alongside my goals and my principles—I realized I could make tough decisions and still sleep easy at night, knowing at a minimum that no one in my position, given the same information, could have made the decision any better.”

4. There are some things you can delegate and other things that you can't. Success comes with knowing what to delegate and to whom.

An entire chapter (Chapter 10) is devoted to explaining why and how he chose the members of his presidential team. Selecting the right people with the right attitude and expertise for the job is important.

However, there are some things that cannot be delegated to other people, no matter how much expertise they have. Building the culture of the White House is one example:

“Keeping up morale, on the other hand, wasn’t something I could delegate. I tried to be generous in my praise, measured in my criticism. In meetings, I made a point of eliciting everyone’s views, including those of more junior staffers. Small stuff mattered—making sure it was me who brought out the cake for somebody’s birthday, for example, or taking the time to call someone’s parents for an anniversary. Sometimes, when I had a few unscheduled minutes, I’d just wander through the West Wing’s narrow halls, poking my head into offices to ask people about their families, what they were working on, and whether there was anything they thought we could be doing better.”

5. To be resilient is to commit to accepting the situation you're in, no matter how sh*tty it is.

His presidency started with a global financial crisis, record high unemployment rates, and was scattered by various disasters such as the Deepwater Horizon Water Spill. What do you do when sh*t hits the fan? Obama channels his inner grandmother.

"I’ve often been asked about this personality trait—my ability to maintain composure in the middle of crisis.... In tough spots, I tend to channel my grandmother.”

This means doing what needs to be done given what you have available to you.

“She taught me the value of working hard and doing your best even when the work was unpleasant, and about fulfilling your responsibilities even when doing so was inconvenient. She taught me to marry passion with reason, to not get overly excited when life was going well, and to not get too down when it went badly.”

(2) Obama's Journey

2a. Deciding to run for president

Part 1 of the book documents Obama's journey from his teenage years to becoming the senator for Chicago.

Growing up, there was little sign that Obama was going to be a politician. He didn't grow up in a particularly political family. He describes his teenage self not as "a budding leader" but rather a "a lackadaisical student, a passionate basketball player of limited talent, and an incessant, dedicated partyer".

“no one in my family would ever have suggested I might hold public office someday. If you’d asked my mother, she might have imagined that I’d end up heading a philanthropic institution like the Ford Foundation. My grandparents would have loved to see me become a judge, or a great courtroom lawyer like Perry Mason.”

However, things change when he goes to Occidental College in 1979 - “The two years I spent at Occidental represented the start of my political awakening." He transfers to Columbia University after his sophomore year and "lived like a monk - —reading, writing, filling up journals, rarely bothering with college parties or even eating hot meals. I got lost in my head, preoccupied with questions that seemed to layer themselves one over the next."

When he graduates from college in 1983, he goes into community organizing and then goes to Harvard Law School. He meets Michelle while interning at a Chicago law firm the first year after law school. At the end of this part, Obama runs for and wins the Chicago senate position.  

2b. Running for president

Part 2 of the book documents his road to becoming president, starting from the Iowa caucus in Chapter 5 to his presidential campaign and victory over McCain in Chapter 9.

2c. What the Obama administration did

Parts 3 to 7 of the book describes the series of problems the Obama presidency faced and how his team went about solving these problems. Here is a list of the major policies they put in place.

Economic policy

In September 2009, two months before Obama won the election, Lehman Brothers collapsed. So the start of his presidency is marked by the largest banking crisis since the Great Depression. His first term was largely devoted to passing a major stimulus bill.

“By any conventional yardstick, I was about to sign historic legislation: a recovery effort comparable in size to FDR’s New Deal. The stimulus package wouldn’t just boost aggregate demand. It would help millions weather the economic storm, extending unemployment insurance for the jobless, food assistance for the hungry, and medical care for those whose lives had been upended; supply the broadest onetime tax cut for middle-class and working-poor families since Reagan; and provide the nation’s infrastructure and transportation systems the biggest infusion of new spending since the Eisenhower administration.”

Along with this, the team put in place other structural changes. Most notable is Tim Geithner's "Stress test" ("The Federal Reserve would set a benchmark for how much capital each of the nineteen systemically significant banks needed to survive a worst-case scenario. The Fed would then dispatch regulators to pore over each bank’s books, rigorously assessing whether or not it had enough of a financial cushion to make it through a depression; if not, the bank would be given six months to raise that amount of capital from private sources.") and signing the Dodd-Frank act in July 2020 ("Dodd-Frank would check a number of reckless practices, give regulators the tools to put out financial fires before they got out of hand, and make crises on the scale we’d just seen far less likely.”)

Healthcare reform

This was Obama's top domestic priority. He saw it as a moral issue. In November 2009, Congress passed Obamacare. The bills expanded Medicaid and provided healthcare subsidies (chapter 17).

Foreign policy

The administration increased the number of soldiers in Afghanistan (chapter 13), negotiated a nuclear deal with Iran and Russia (chapter 19), tried to negotiate with China about their gaming of the international trading system (chapter 20), pressured Mubarak to step down during the Arab Spring (chapter 25), and oversaw the killing of Osama Bin Ladin (chapter 27).

Environmental policy

Obama drafted the Copenhagen Accord (successor to the Kyoto Protocol) which required developing countries to monitor their carbon admissions (chapter 21) and had to deal with the deepwater horizon oil spill (chapter 23).

Civil rights and Immigration

LGBTQ Rights: In December 2010, he repealed "don't ask don't tell", ending the military's policy of disallowing openly gay and lesbian people from serving in the army (chapter 24).

Immigration: However, they didn't manage to pass the "Dream Act" which would allow young, undocumented immigrants legal status (chapter 24).