So Here's the Thing . . .

Notes on Growing Up, Getting Older, and Trusting Your Gut


By Alyssa Mastromonaco

With Lauren Oyler

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From the New York Times bestselling author of Who Thought This Was a Good Idea? comes a fun, frank book of reflections, essays, and interviews on topics important to young women, ranging from politics and career to motherhood, sisterhood, and making and sustaining relationships of all kinds in the age of social media.

Alyssa Mastromonaco is back with a bold, no-nonsense, and no-holds-barred twenty-first-century girl’s guide to life, tackling the highs and lows of bodies, politics, relationships, moms, education, life on the internet, and pop culture. Whether discussing Barbra Streisand or The Bachelor, working in the West Wing or working on finding a wing woman, Alyssa leaves no stone unturned…and no awkward situation unexamined.

Like her bestseller Who Thought This Was a Good Idea?, SO HERE’S THE THING… brings a sharp eye and outsize sense of humor to the myriad issues facing women the world over, both in and out of the workplace. Along with Alyssa’s personal experiences and hard-won life lessons, interviews with women like Monica Lewinsky, Susan Rice, and Chelsea Handler round out this modern woman’s guide to, well, just about everything you can think of.


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 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.)

This book is an attempt at a conversation, not a statement. It’s the thing. What you learn as time goes on is that nothing is perfect, and there’s always a the thing. “So here’s the thing” means I’m basically about to edit something you’re 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 there’s always the thing. It’s gotten to the point where my starting a sentence with “So here’s the thing” sends everyone at work into a frenzy.

“Oh no!” they cry. “Not the thing!”

WTF Is Politics Anymore?

As an experiment, I’m 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.
  • Donald Trump pulled out of the Iran nuclear deal.
  • It was revealed that ICE had been separating migrant children from their parents at the border and detaining them without keeping track of who they were or how their parents could be reached.
  • Trump treated his historic summit with North Korea like a WWE match-up, alternately trading insults and boasting so that no one knew if it would actually happen.
  • John McCain died.
  • An anonymous senior staffer in the Trump administration published an op-ed in the New York Times claiming there was a “shadow Cabinet” specifically dedicated to undermining Trump’s leadership. (“Leadership.”)
  • Brett Kavanaugh, Trump’s nominee for the Supreme Court, was accused of sexual harassment by Dr. Christine Blasey Ford, ushering in a slew of further accusations against him. Dr. Blasey Ford and Kavanaugh testified in front of the Senate Judiciary Committee, an occasion that involved the latter saying things like “I like drinking beer” as evidence of his suitability to be confirmed.
  • He was, despite the ludicrousness of the affair and the unanimous agreement that Dr. Blasey Ford’s testimony was credible, confirmed to the Supreme Court.
  • The New York Times published an article claiming that Rod Rosenstein suggested secretly recording Trump in order to gather evidence for invoking the Twenty-Fifth Amendment.
  • The long-awaited midterm Blue Wave maybe happened? It’s unclear. The Democrats regained control of the House by the biggest margin since Watergate, but the GOP retained control of the Senate, as was expected. Reports of rampant voter suppression inspired outrage, and several races remained too close to call for weeks.

It wasn’t all bad. I woke up at 6:00 AM to watch the Royal Wedding with enthusiasm (and themed snacks). Ireland overturned its abortion ban. But the overall impression has been one of shock, followed by the sense that I shouldn’t still be shocked at this point. Repeat. Trump is doing exactly what he said he would, and then some, which is what he suggested he would do. Yet scrolling through Twitter still feels like an emotional roller coaster, one of the old, rickety wooden ones you’re pretty sure would never pass a safety inspection today: Anything funny or lighthearted is inevitably followed by some breaking New York Times investigation that reveals everything to be worse than you imagined. You leave feeling shaky, disoriented, and like you’re definitely going to hurt tomorrow.

It’s a privilege to be shocked: I understand that as a middle-aged white woman with money, I have always been and will always be insulated from the real effects of these policies. I’m not going to be needing an abortion anytime soon (and if I did, I could easily access one). But I also think it’s important to be honest about where we’re all coming from if we’re going to build a viable resistance and, eventually, win back the White House. Because from where I sit, the left remains a hot mess.

When my first book came out in March 2017, the reality of the Trump presidency had not really sunk in. I’d expected to unleash the book into an atmosphere of hope and optimism brought in by the first female president, who would, I expected, more or less continue Obama’s policies. When I woke up to my tear-stained pillow on November 9, 2016, to confirm that the Trump thing wasn’t just a nightmare, I realized, too, that I had no idea what was actually going to happen. It just seemed like a huge cloud of BAD was about to descend on my former workplace.

Now, more than two years later, I still quite frankly have no idea what’s going to happen. Or what’s happening now. As someone who had a long, successful career working in government, and who is now regularly called upon to comment on politics, I’m supposed to be an expert on it. But the only thing I can say from experience is that trying to predict what will come of Trump’s volatility and wake of destruction is a waste of time. I can tell you what it means that Trump didn’t visit Canada until more than a year after he took office and hasn’t yet been to Mexico at all. I can tell you what it means that he hadn’t filled hundreds of government positions more than five hundred days after he took office. I can tell you what the chief of staff does and why it was gravely concerning that Trump’s first one resigned in disgrace—remember that? It’s like it happened decades ago—and that his second one probably told Bob Woodward that the president is “an idiot.”

But what’s going to happen? Trying to answer that question is an exercise in futility that only makes well-meaning pundits look like out-of-touch know-it-alls. The Republicans can’t even predict what Trump’s going to do or what scandalous cover-up is going to come out, and they’re totally desperate to do so in order to maintain their status as ringleaders of the circus. I have to admit, it is a little fun to watch Mitch McConnell and John Kelly scramble to clarify or retract whatever inane thing Trump has said or done. But it’s not that fun, because it makes clear that nothing in the American government matters if no one believes it does.

This is an uncool position to take, but the revelation that institutions like the presidency might be held together by little more than the Tinkerbell effect was deeply disappointing to me. When I go on TV to comment on something, I sometimes feel like I’m screaming “BUT IT’S IMPORTANT!” into a void. Maybe it’s that I don’t want all the work I’ve done over the years to be for nothing. It’s partially that. But it’s also true that I did all that work because I believed that I was helping, in some small way, to make people’s lives easier. I believed things were slowly but surely getting better.

*  *  *

I have a memory of being woken up at 5:15 in the morning by Rahm Emanuel back in 2006 that I think illustrates how much things have changed. I was working for Obama, who was, like many popular sitting senators, on the campaign trail for the midterm elections, boosting Democratic candidates.

I was also hooking up with a guy named Bob. His house always smelled like mildew. We had gotten wasted the night before, so when my phone rang at 5:15 AM, I considered letting it go. I was desperately hungover. But I knew we were in a high-stakes moment, and when I looked at the caller ID I saw that it was Rahm, who was the head of the Democratic Congressional Campaign Committee (DCCC) at the time.

“Alyssa. Alyssa? It’s Rahm, Rahm. It’s Rahm. Alyssa. John? John’s dead. He’s not going to be able to do anything else. He’s radioactive. He really fucked up. He really fucked me over.”

Because my brain was wading through alcohol, I groggily assumed for a second he meant that John—as in Kerry—was literally dead. But no. What he meant was that John Kerry was supposed to campaign for a string of top-tier candidates for the promised Blue Wave in November, but the night before he had committed a gaffe: He’d said students who can’t navigate America’s education system risked “get[ting] stuck in Iraq.” Fox News and Republicans were already having a field day: John Kerry thought soldiers—our TROOPS!—were stupid.

Rahm was still on the phone. “John’s out, honey. He can’t go on. I gotta fill all these targets. Here’s what I need, all right…”

I got out of bed. (Far from being miffed that his lover was abandoning him in the middle of the cold, dark night, Bob was seriously impressed that I was fielding calls from Rahm Emanuel at five in the morning.) I told Rahm that Obama could replace Kerry at several events, went to Dunkin’ Donuts for a coffee, and prepared to inform Obama of his new schedule. Obama was annoyed—I believe the comment was: “Are you working for Rahm or me?”—but Obama’s involvement during that campaign season also catapulted him from promising young senator to “That guy should really run for president.” And the thing was, we all knew Rahm wasn’t wrong. John Kerry was radioactive and wouldn’t have been any help to anyone. He’d also been planning to run for president again in 2008, but his glib remark meant he’d no longer be able to.

The fact that one ungenerously interpreted offhand comment could ruin John Kerry’s hopes of running for president again was not an indication that the American political system was healthy. No. Particularly because he wasn’t insulting the military. He was making a basic yet important point: America needed to invest more in education so that young people from lower-class backgrounds didn’t feel the military was their only option. Any normal person would be able to see he wasn’t disparaging the military. It didn’t matter.

But if traditionally politics was guided by oversensitivity, today it’s guided by blatant, shameless opportunism. There’s been a total 180. Whereas every single comment used to be dissected with ruthless bad faith, now nothing anyone says matters at all. How many times has some news story broken to cries of “This is finally the nail in the coffin for Trump”? And it never is.

*  *  *

How are we, as engaged citizens, supposed to react to the news? There’s a confusing disconnect between the experience of reading the news (whiplash) and the apparent lack of effect it has on the actual political situation (Trump is still in office). On one hand, it’s critically important that we not get complacent and start treating the cruel absurdity as “normal.” On the other, despite our best efforts, the news cycle is becoming normal—the outrage that follows any one abysmal policy decision is drowned out by the outrage that follows the next one. Democratic presidential hopefuls tweet grave rebukes of the Trump administration to much celebration on social media and little practical avail. Republicans get aggravated, pay lip service to their constituents’ furious concerns, and then ultimately do exactly what they planned on doing in the first place. Everyone in government seems more concerned with their images than with the clusterfuck they’ve wrought on the American people.

This has effects both in America and around the world. In 2014, Obama was the first sitting president to visit Burma, to encourage the country’s liberalization process after the relative easing of its military regime. Though the optimism of that visit took a turn shortly after, going on that trip was a reminder of how much significance the American president has around the world, not just to diplomats and leaders but to ordinary people. There were so many people in the streets, waving Burmese and American flags, that they couldn’t be held back; the motorcade was going at parade speed—with POTUS still freaking out about hitting someone. Even if the policy discussion was flawed, the effect his visit had on the Burmese people was clear: He was validating them. Of course, a visit from an American president shouldn’t be a validating event for an entire nation. American foreign policy has often been ruthless and terrible. But that’s the world we live in, and seeing the happiness Obama brought those people was something of a consolation.

Maybe it was always a house of cards. (I guess that’s why the show is called House of Cards.) But I think there was some value in it. By treating foreign governments and peoples as though they’re pawns to be manipulated in a game that America is rigged to win, Trump is insulting them. Even the way the administration communicates with the people is ad hoc and panic-inducing. For months, the appearance of a new Trump tweet on North Korea would be followed by strings of semiserious text messages from friends asking if there’s a fallout shelter near my house and saying that if the world is going to end at least I won’t have to go on my business trip next week. Trump often brags about having avoided war with North Korea—forgetting, I guess, that his ability to do so is thanks to all the previous presidents, who also avoided war with North Korea. And they did it without so fully terrorizing the citizens of both countries. You can see that people are scared. It’s not as if other presidents haven’t engaged in brinkmanship, or high-flown back-and-forths, but they haven’t done so with the volatile intensity of Trump’s tweets, which foment panic and urgency. What’s more, the way Trump teased the Kim Jong-un summit, as if it were the season finale of a reality TV show, frittered away the significance of the diplomatic opportunity. Whoever comes after Trump—if anyone does—is going to have a very difficult task ahead of them if they want to restore the meaning of those kinds of visits and of the American government in general.

Of course, political rhetoric has always been strategic and biased. The difference is that in the past, politicians might have made statements you disagreed with, in order to sway voters. Obviously, you’re always going to present an issue the way you see it. But there’s a difference between Obama saying “The ACA is going to help many families stay out of poverty by giving them access to basic health care” and, as Trump once tweeted, “Obamacare is imploding. It is a disaster and 2017 will be the worst year yet, by far!” For the people who depend on Obamacare for health insurance, that kind of fear-mongering has a real effect. By treating every issue with the same level of intensity and hostility, Trump is a propaganda machine, sowing anxiety in order to scare his base into voting for him. When most presidents get into office, they make an attempt to speak to the entire American population, to at least gesture toward bipartisanship. The Democrats have been too conciliatory in this way. But Trump communicates as the Republican president to his core MAGA supporters and seems to truly believe that everyone else is out to get him. He is incapable of taking his own power into account or of understanding any actual policies. He never explains his own position (probably because he doesn’t really have one) and instead just says whatever he wants at the time. He has no sense of responsibility to anyone but himself.

I wish I could say that I felt confident in our side’s ability to respond to all this. But I can’t say that. It sometimes seems as if the Democratic Party is engaged in a slapstick performance of ineptitude for laughs. There’s no other way to explain why they do some of the things they do. Nobody is ever going to beat Donald Trump playing his game. When Chuck Schumer or Nancy Pelosi tries to be as inflammatory as Trump, it just lands flat; they can’t rouse people, and worse, the obviousness of their attempts to rouse people makes them look worse. (If you’re going to try, you need to make it your own!) Donald Trump is a television producer, desperate for ratings and an expert at getting them; the people who are up against him are legislators who look ridiculous when they act as though they’re auditioning for roles on a reality TV show about American politics.

While I was working on this book, people kept talking about Joe Biden as a top candidate for 2020. Joe Biden. Joe Biden! I love, love, love Joe Biden. But pollsters and pundits, desperate for someone to root for, get dazzled by name recognition and put him at 30 to 40 percent odds, forgetting that most of America has never heard of Kamala Harris, Cory Booker, or Kirsten Gillibrand. Eric Gar-who? The 2020 field is going to be absolutely packed. Anything could happen. Joe Biden polls high not because Americans want Joe Biden but because he’s the best person they’ve heard of.

I always have to think long and hard about how to disagree with Democrats because I’m afraid I’ll get kicked out of the party. Which is part of the problem. The left’s mantra is supposed to be about inclusivity, but you only get included if you have the same views the algorithm came up with. Those at the top of the DNC don’t want to listen to any criticism or consider any viewpoint that doesn’t mesh with their vision for the party, which is based way too much on appearances and not enough on grunt work and boots on the ground. Even after the 2016 election—when I told them, screaming into the void, “Pay attention to Bernie!”—some members of the party still refuse to see what’s right in front of their faces. Back in 1994, “progressive” was code for “socialist”; now it means a non-moderate Democrat, someone who’s on the right track but not fully on board with the agenda many young people want, which includes Medicare for all, free tuition, and criminal justice reform. Even for me, someone who is basically a socialist—does this count as my coming out?—it’s still surreal to see the label being proudly embraced by millennials, Gen Z, and even politicians. But I’ll get used to it, and the Democrats need to, too. People want government health care. People want dignity and expanded social services. People are sick of seeing downright villains get away unscathed from the wreckage they’ve caused and with their riches intact. It’s a shame that the next Democrat to win the presidency is going to have to fight his or her own party for legitimacy. Whoever does it will have to run without fear of losing and without backing from the polls.

Maybe by the time you read this we’ll have a better sense of who the Democrats will run. Regardless, I don’t look forward to watching the overcrowded primary debates. As voters, we have a responsibility to start looking at who really wants it—not who wants it because they want to be the president, because they want to see themselves in that office (and with that Twitter handle) but because they want to serve. The election in 2016 showed us that polls are not a reliable foundation on which to build a campaign. The people are. The best politicians, the ones I get excited about, know that.

*  *  *

When I left the White House, I wanted to be done with it all. I was tired. I’m conflict-averse, and I felt I’d done my time. I don’t like the sparring and politicking and behind-the-scenes jousting. I hated the theater of the dueling press releases, and I hate the spectacle of Twitter even more.

And never did I imagine that two and a half years after leaving my office in the West Wing—a building I didn’t just respect but loved with my whole heart—I would be outside those gates protesting a new president who gloated about grabbing pussies. On the one hand, it would be easy for me to tap out and avoid involvement.

On the other, I couldn’t do that in good conscience.


  • "Reading So Here's the Thing... is exactly like hanging out with Alyssa. You will laugh a lot, learn even more, and just be grateful that she is your friend."—Dan Pfeiffer, #1 New York Times bestselling author of Yes We (Still) Can and cohost of Pod Save America
  • "My favorite thing about Alyssa's books is knowing someone as normal as the rest of us can work in the most prestigious positions in the world and do it with a sense of humor and self-deprecation. We could all do with more of both. Read it, and laugh."—Chelsea Handler, #1 New York Times bestselling author of Are You There, Vodka? It's Me, Chelsea
  • "Growing up is hard. Trusting your gut? Sheesh. That sounds impossible at times. Let Alyssa Mastromonaco hold your hand and show you that with some good laughs and a lot of heart, life can be a little less daunting. I wish I'd read this book when I was younger, but it still resonates today, and I know it will be relevant at all stages of life. What a gift."—Aminatou Sow, co-founder of Tech LadyMafia
  • "I'm just going to say this book lets the 'cat out of the bag,' so to speak: everyone who knows her or reads her work wants to be Alyssa's best friend. SO HERE'S THE THING... makes it impossible not to want that. Her life stories somehow make all of us feel seen. All of which means my position on the waiting list for the best friend title may shift. While I'm coming to terms with that, I will also say I'm all for mixing patterns, just not always the ones Alyssa puts together."—Stacy London, New York Times bestselling author of The Truth About Style
  • "[So Here's The Thing...] is a delightful, digestible nosh of useful tips from Mastromonaco's long career in politics."—Portland Mercury
  • "Funny and...insightful. An entertaining miscellany by a sharp-eyed observer."—Kirkus
  • "Behind-the-scenes moments from [Mastromonaco's] career provide insights into the hectic work of campaigns and the White House...readers will enjoy the relaxed tone that Mastromonaco and coauthor Oyler set throughout -- like chatting with old friend, who just happened to have Mindy Kaling set up her Twitter account."—Booklist

    "Always fascinating and very funny, Alyssa's book is full of juicy stories from one of the world's most glamorous jobs."
    Mindy Kaling, New York Times bestselling author of Is Everyone Hanging Out Without Me? (And Other Concerns) and Why Not Me?
  • "WHO THOUGHT THIS WAS A GOOD IDEA? is everything we've come to know and love about Alyssa over the decade we worked with her: brilliant, funny, grounded, and inspiring. Anyone who's interested in politics - especially young people - should read this book."—Dan Pfeiffer and Jon Favreau, former communications director and speechwriter for President Barack Obama
  • "Few people have had as much access and influence over national events over the last decade as Alyssa Mastromonaco. No matter how serious the crisis or hard the problem, Alyssa took care of it with great skill and professionalism, and even greater humor. This book tells the story of a young woman succeeding under extraordinary circumstances, and throughout it all, never taking herself too seriously."—Stephanie Cutter, former deputy campaign manager for President Barack Obama
  • "I've often wondered how a woman can be so many things wrapped up in one dynamic package. Alyssa is my fairy godmother: she's wise, resourceful, insanely smart, and makes me laugh in a very special way. Her stories - from the front line of the White House to her kitchen - will entertain, inspire, and humor you for a long time to come."—Amanda de Cadenet
  • "Alyssa is a force: whip-smart, humble, and funny as hell. Her writing is as fearless as she is."—Sophia Amoruso, founder and CEO of Girlboss
  • "When imagining working in the White House, many picture meaningful meetings, glamorous dinners, and high-stakes decision making. It can be all of those things. But as Alyssa Mastromonaco writes in WHO THOUGHT THIS WAS A GOOD IDEA?, the reader gets a real and raw peek behind the curtains where Alyssa experiences the good, the bad, the distressing, and the often hilarious. Alyssa has real grit and grace, and her book is her story very well told."—Dana Perino, New York Times bestselling author of And the Good News Is... and Let Me Tell You About Jasper...
  • "A combination memoir and compendium of very good suggestions about how to get ahead -- very far ahead -- at an early age."—The Washington Post

On Sale
Mar 10, 2020
Page Count
240 pages

Alyssa Mastromonaco

About the Author

Alyssa Mastromonaco served as assistant to the president and director of scheduling and advance at the White House from 2009 to 2011 and as assistant to the president and deputy chief of staff for operations at the White House from 2011 to 2014. She is the New York Times bestselling author of Who Thought This Was a Good Idea? with Lauren Oyler and a contributor to Crooked Media.

Lauren Oyler is a writer whose work has appeared in the New York Times Magazine, the Baffler, the New Republic, VICE, and elsewhere.

Learn more about this author