Alyssa Mastromonaco - So Here’s the Thing . . .: Notes on Growing Up, Getting Older, and Trusting Your Gut

Once in a while you get shown the light

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

Scarlet Begonias, Grateful Dead

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 destabilizingeveryone 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. Thats what I like about the phrase So heres 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 dont work that way. I want to help my friends and colleaguesand the occasional Twitter user who @s meweigh options and then pick the best one, considering all the benefits and drawbacks, without denial or wishful thinking.

So heres 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 theres no right path or way to deal with a problem or achieve a goal. Heres 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 qualitiesflexibility and adaptabilityare realistic ones. They require you to think about a particular set of circumstances and respond to them accordingly.

I didnt really start thinking in terms of so heres the thing until the summer of 2008. Before Obama became the Democratic presidential nominee, wed been talking about taking a foreign trip as part of the campaign. As a candidate, youre 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 Obamas diplomacy skills, get some good press for being capable and charming abroad, and generally demonstrate how popular hed 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 couldnt say no. I would never say no. I dont think thats how you get what you want, and anyway, Im always willing to be wrong. Except when it comes to other peoples 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 heres the thing: I think three countries is achievablewe 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 heres the thing is also a gentle (probably feminine) way of letting people know they might not like what youre about to say, its also helpful when youre 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 heres the thing: Were 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 manningor womanningthe 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 heres the thing: The landing gear I really did not want to have to go to Obama and say, So heres the thing: The plane wont fly. (Luckily, the landing gear turned out to be OK.)

This book is an attempt at a conversation, not a statement. Its the thing. What you learn as time goes on is that nothing is perfect, and theres always a the thing. So heres the thing means Im basically about to edit something youre thinking or doing, in the nicest way possible. It might be about needing to break up with a boyfriend, quit a job, apply for a higher-level position, or figure out a way to pay off your student loans, but theres always the thing. Its gotten to the point where my starting a sentence with So heres the thing sends everyone at work into a frenzy.

Oh no! they cry. Not the thing!

As an experiment, Im going to list, off the top of my head, all the news I can remember interrupting me while I was trying to write this book:

• Students organized a nationwide walkout to protest gun violence.