Expectations were high, my performance low. I knew the subject, but somehow couldn’t articulate my ideas coherently. Delegates didn’t hold back when it came to criticism and told me afterwards that my strategy was unclear, my content muddled and that I had given them no clear direction. It would have been so easy for me to have run my presentation by Louis in the days before I gave it - but I hadn’t wanted to subject myself to negative feedback. So I’d blundered on. I felt that I’d blown it and feared being sent back home.

I was also told that a brand-new CEO shouldn’t be trying to make huge acquisitions. I was “crazy,” as one of our investment bankers put it, because the numbers would never work out and this was an impossible “sale” to the street.

The banker had a point. It’s true that on paper the deal didn’t make obvious sense. But I felt certain that this level of ingenuity was worth more than any of us understood or could calculate at the time. It’s perhaps not the most responsible advice in a book like this to say that leaders should just go out there and trust their gut, because it might be interpreted as endorsing impulsivity over thoughtfulness, gambling rather than careful study. As with everything, the key is awareness, taking it all in and weighing every factor—your own motivations, what the people you trust are saying, what careful study and analysis tell you, and then what analysis can’t tell you. You carefully consider all of these factors, understanding that no two circumstances are alike, and then, if you’re in charge, it still ultimately comes down to instinct. Is this right or isn’t it? Nothing is a sure thing, but you need at the very least to be willing to take big risks. You can’t have big wins without them.

Then I made two other mistakes. One was that I didn’t fully appreciate the importance of simply provisioning traditional institutional reassurance. By asking and challenging everything, you create a lot of uncertainty, and that uncertainty can be debilitating to the ongoing functioning of the organization. I failed to appreciate that if you’re going to be questioning everybody and challenging everybody, you have to do a lot of reassuring in return. I didn’t say, ‘Isn’t Harvard great?’ If I had said that, it would have been much more reassuring.” - Lawrence Summers.

Thankfully, there were people close enough to me to tell me the truth. I had a number of conversations with senior staff, who told me there was ambiguity where there shouldn’t have been any: “Nobody’s making decisions, and when someone does step up, they’re accused of making a power grab. You have to name a GM, Will.”

But all I heard was: You need to work harder. You’re not here and you need to be, so you better figure out a way to shoehorn an extra hour into the day so you can do your new job and this one, too. No matter how guilty I felt, I was able to rationalize it away. “How bad could it be, when our guests were so happy?

Chapter 6: Victory in our Lifetime: Marriage

“‘What else should we have done?’ he responds, his voice calm and even. ‘We weren’t burying our heads in the sand. We were saying we’ve got this good thing going on, and even if we don’t know where it's going to take us, let us commit. Because love is about committing.’ I guess no one ever really knows how a marriage will unfold. You just take a chance. You bet on your love.