How I Approach the Toughest Decisions

Our choices reflect and determine who we are.

Barack Obama
8 min readDec 9, 2020
Photos by Pete Souza

One of the first things I discovered as President of the United States was that no decision that landed on my desk had an easy, tidy answer. The black-and-white questions never made it to me — somebody else on my staff would have already answered them. And while few decisions in life are as complex as the ones you face in the Oval Office, I did walk away from my eight years as president with some thoughts on how to approach tough questions.

In March of 2009, just a couple of months into my presidency, the economy was in freefall. Unemployment was up to 8.5 percent, on its way to ten percent. 800,000 Americans lost their jobs that month, families across the country were losing their homes, a tanking stock market was depleting their 401ks, and a difficult credit market was making it hard for small business owners to take out the loans they needed. To turn around any of this required stabilizing the financial system, and to do that, I had settled on what was the least bad of three lousy options — subjecting the 19 largest banks to “stress tests” to see whether they had the capital to survive an even worse economy.

Nobody was happy about it — not the public, not Wall Street, not me. My own advisors disagreed about the path forward, with some calling for a sharper condemnation of the bankers whose recklessness had gotten us into the mess, and others saying that such gestures might stifle the very market confidence we needed.

To get everybody on the same page, I called a meeting with my economic team. We spent a long, exhausting day hearing from Treasury Secretary Tim Geithner about how the stress tests were going, hashing out various alternatives, and pushing every idea to its logical conclusion to see if it might work. By evening, I left the meeting to have dinner and get a haircut and told my team that I expected a consensus upon my return. But the truth was that, through that grueling process, I had already reached my decision to let the stress tests bear out. Within six months, the economy would start growing again. And by the next year, the biggest banks had paid back every dime of taxpayer money — plus interest.

But the point is, in just a few short weeks on the job, I had already realized that because every tough decision came down to a probability, then certainty was an impossibility — which could leave me encumbered by the sense that I could never get it quite right. So rather than let myself get paralyzed in the quest for a perfect solution, or succumb to the temptation to just go with my gut every time, I created a sound decision-making process — one where I really listened to the experts, followed the facts, considered my goals and weighed all of that against my principles. Then, no matter how things turned out, I would at least know I had done my level best with the information in front of me.

There was something liberating, and humbling, about leaning on a process.

Of course, that only works if you listen — really listen — to others. For me, that meant asking everybody in a meeting what they thought about the problem at hand. I’d call on folks in the back row, including the most junior staffer. That required people to come prepared to share their views.

But, like every leader, I had my blind spots. Late in my first year, Valerie Jarrett reported that some of the senior women on staff were experiencing a culture where the men on the team interrupted them, dismissed their ideas before adopting them as their own, and generally made them feel diminished — to the point where some of the women had altogether stopped talking in meetings. These were some of my most important advisors, so I convened them over dinner to hear more. Listening to their stories, I considered the degree to which my own tolerance for machismo behavior had contributed to their discomfort and, inadvertently, stifled their important contributions. We didn’t resolve everything in one night — but being aware was a start. The men, I later discovered, had been oblivious — and were appropriately mortified. They promised to do better, and a few months later, Valerie said she noticed some improvement.

One of the earliest decisions I had to make about the war in Afghanistan was one that had been pending since before I took office. Although we were planning to revamp our entire strategy, the commander on the ground was requesting an immediate deployment of an additional 30,000 troops. That’s how I found myself in the Situation Room, two days after inauguration, discussing the issue with the principal members of the National Security Council — people like the Chairman of the Joint Chiefs of Staff and the Director of the CIA. Almost everyone in the group was inclined to support the troop deployment.

Except for my Vice President, Joe Biden. He made the case to delay deployment until we had a clearer strategy. It wasn’t easy. Speaking up exposed him to criticism. But Joe’s willingness to go against the grain and ask tough questions was invaluable — and it would continue to be a trait I relied on throughout my eight years. Because one of the risks of soliciting views from a large group is that a current of thinking can quickly take shape and move everybody in the same direction. Having at least one contrarian in the room pushed us all to think harder — and, frankly, everyone was a bit freer with their opinions when that contrarian wasn’t me.

When you have a tough, almost unsolvable decision to make, you don’t just want people to tell you what you want to hear.

You also want to create space to think. Remember that dinner and haircut break I took during that marathon economic session? That mattered, too. That was part of making the decision. Even in situations where you have to act relatively quickly, as was frequently the case during the financial crisis, it helps to build in time to let your thoughts marinate.

You can’t always plan a well-timed break or predict how it might clarify your thinking. One evening in March of 2011, my national security advisors and I were engaged in a stressful discussion about whether to intervene in the ongoing conflict in Libya. At some point, I had to step out for a dinner with the U.S. military combatant commanders and their spouses.

Seated next to a young Marine who had lost both his legs to an IED in Afghanistan, I couldn’t help but think about the decision that awaited me about whether to send more young men like him off to the battlefield. We sat just a stone’s throw away from the airless Situation Room — but the space and perspective that dinner afforded helped refine my thinking. And by the time they cleared dessert, I had reached a decision.

In my first year, I would sometimes walk over to the small pool house by the Oval Office and have a cigarette (or two), savoring a quieter moment and letting my thoughts wander and deepen. After signing the Affordable Care Act into law, I finally quit smoking for good — but took pains to maintain other outlets, other rituals, that helped preserve some boundaries, however tenuous, between life and work. My morning workout, an evening walk on the South Lawn, after-dinner pool games with our dear friend and family chef Sam Kass. Whatever decision I might be carrying would breathe a little — and so would I.

Those rituals included leaving the Oval Office at six-thirty each night so that I could have dinner with my family. There was nothing more refreshing than spending that time with the three most important people in my life — listening to Malia and Sasha narrate their days, ask questions and tease me to no end. Afterwards, Michelle and I might get a few extra minutes alone to catch up. I always found myself replenished, as though my family had decluttered my mind and restored my equilibrium.

Many of us tend to work relentlessly — whether it’s at our jobs or taking care of our families. It can feel like there just aren’t enough hours in the day to take time out. But it’s actually vital. One thing I learned as president was that the decisions I had to make were so weighty and consequential, the pace so unyielding, that it was easy to feel almost removed from myself. But the time I spent away from my desk, especially with my wife and kids — whether coaching Sasha’s basketball team or date night with Michelle — was a crucial, daily reminder of who I fundamentally was as a person. This was so important, because we bring our whole selves to the decisions we make. And those decisions, in turn, both reflect and determine who we are.

That was something my mother made sure I understood. Once, she found out that I had been part of a group teasing a kid at school. She sat me down and told me that there were two kinds of people in the world: Those who only think about themselves and tear others down to make themselves feel important. And those who think about how others feel and avoid doing things that might hurt them. “So,” she asked me, “Which kind of person do you want to be?”

All these years later, her question still helps guide my decisions. On an official visit to Japan, I met with the Emperor and his wife, and instinctively made a little bow. To me, it was the most obvious, natural thing to do — a sign of respect in a different culture. I later learned that conservative commentators threw a fit, with one calling my bow “treasonous.” Rather than anticipating and fearing the right wing’s bizarre insecurity about my carrying out a culturally appropriate greeting to my elderly hosts, I followed my own basic humanity and sense of decency.

Everything I learned about making impossible decisions during the first two years of my presidency culminated in one of the toughest choices I had to make: whether to authorize the raid to take out Osama bin Laden. It was an operation rife with uncertainty and risk. So, I ran a tight process. I trusted my team. I listened to every voice in the room. I gave myself space to think. And then I made a decision that reflected my own personal sense of what was right.

While I couldn’t guarantee the outcome, I was confident in making the decision.

Looking back, the number of complex situations I had to adjudicate seems remarkable — that’s the job of the President of the United States. But the truth is that, even as regular Americans going through our days, we face countless decisions — a reality made even more acute by the pandemic. We’re constantly assessing how to act and what to do, carefully weighing the safety of each choice. It can be exhausting.

The best we can do is find a framework that helps us consider our choices, knowing that there may not be one perfect answer. That way, we can rest a little easier knowing that did the best we could in the circumstances, come what may.

It’s not always clean and straightforward. But as my mother would say to me, “The world is complicated, Bar. That’s why it’s interesting.”