So Here’s the Thing…: Notes on Growing Up, Getting Older, and Trusting Your Gut

So Here’s the Thing…: Notes on Growing Up, Getting Older, and Trusting Your Gut

Alyssa Mastromonaco


This one is for all the wee dames-in-training:

JJ (aka “Cheeks”), Alice, Gigi, Val, Hailey, Lilz, Emily, Freddie, Nina, Ruby, Nico, Emzy, Grace, Sofia, Kyla, Clara—and Midge!





Once in a while you get shown the light

in the strangest of places if you look at it right.



“Scarlet Begonias,” Grateful Dead





Introduction



People these days want to make definitive statements, and to read definitive statements. Chalk it up to the political situation, which is confusing, unpredictable, and destabilizing—everyone wants something solid and dependable to latch on to. They want the comfort and clarity of advice to steady them during these wild times.

Unfortunately, I believe the best advice is not definitive but situational. That’s what I like about the phrase “So here’s the thing.” Which I happen to say all the time. I mean, all the time. When people ask me for advice, I understand they want something straightforward, an injunction: “Do this, and everything will be fine!” But I don’t work that way. I want to help my friends and colleagues—and the occasional Twitter user who @’s me—weigh options and then pick the best one, considering all the benefits and drawbacks, without denial or wishful thinking.

So here’s the thing (sorry, I had to): I think this is a good attitude to bring to writing a book, which is all about exploration, not declaration. In my first book, Who Thought This Was a Good Idea?, I wanted to suggest that everyone is different and that there’s no right path or way to deal with a problem or achieve a goal. Here’s the cheesy, oversimplified synopsis, for the purposes of this introduction: I used myself as an example of how, though I had only a vague idea of where I wanted to go, flexibility and adaptability helped me accomplish everything I did, which includes becoming the White House deputy chief of staff for operations for President Barack Obama. These qualities—flexibility and adaptability—are realistic ones. They require you to think about a particular set of circumstances and respond to them accordingly.

I didn’t really start thinking in terms of “so here’s the thing” until the summer of 2008. Before Obama became the Democratic presidential nominee, we’d been talking about taking a foreign trip as part of the campaign. As a candidate, you’re not given any resources for foreign travel, so all the transport, logistics, security, and everything else would be totally on us. The idea was to go to two or three countries to showcase Obama’s diplomacy skills, get some good press for being capable and charming abroad, and generally demonstrate how popular he’d be around the world. All fun in theory, but always very distant in practice. We had mostly tried not to get our hopes up about Obama getting nominated at all because it seemed like such a long shot.

But then of course he did become the nominee, so we had to have a real talk about the foreign trip. A conference call was scheduled. I dialed in on time, but when I got there, it seemed everyone else was already talking passionately. The call was under way. And soon my life was flashing before my eyes. The number of countries being mentioned was not two or three. Jordan. Israel. France. The UK. Germany. It was as if they had purposefully arranged to start the call earlier so the decision could be made before I got on. I was the director of scheduling and advance, so planning this was going to be on me.

But as the excited conversation progressed, I couldn’t say no. I would never say no. I don’t think that’s how you get what you want, and anyway, I’m always willing to be wrong. Except when it comes to other people’s love lives. I have 100 percent accuracy on that.

So instead of saying no [way in hell are we doing five countries], I said something to the effect of, “So here’s the thing: I think three countries is achievable—we can execute that. But five is a no-can-do.”

This did not get me the result I wanted. But it did inspire a long conversation in which my fears were moderately assuaged, or I was forced to admit that the cost-benefit analysis did not add up in my favor. Yeah, we did five. And it worked so well because every step of the way, we were being realistic about what we could and could not accomplish. Since “so here’s the thing” is also a gentle (probably feminine) way of letting people know they might not like what you’re about to say, it’s also helpful when you’re handing out undesirable assignments. When we were thinking about how we would coordinate logistics back home when we were traversing so many different time zones and continuing to plan parts of the trip (meaning: When we were in Israel, there was still a lot of Germany to sort out), I remember telling the team who would be in the States, “So here’s the thing: We’re basically going to need twenty-four-hour coverage, so you guys are going to have to figure out what works best. I need to know who I can call when I need answers.” (Translation: Someone was going to have to be manning—or womanning—the phones at 4:00 AM.) The tables were turned when a staff member for the company that owned the plane we were chartering from Amman to Tel Aviv began a sentence, “So here’s the thing: The landing gear…” I really did not want to have to go to Obama and say, “So here’s the thing: The plane won’t fly.” (Luckily, the landing gear turned out to be OK.)