Alyssa Mastromonaco - Who Thought This Was a Good Idea? Former Whitehouse Deputy Chief of Staff

When I first met Barack Obama in December 2004, Im not sure he liked me very much. I had worked for John Kerry on and off for four years, and although the secretary of state has a reputation for being aloof, the two of us had had a very warm and close relationship, pretty much from the moment I started as an assistant in his press and scheduling office in the spring of 2000. I expected my rapport with Senator-elect Obama, who was much closer to me in age and disposition, would be similar. Plus, I was coming off the presidential campaign for the Democratic nominee. I figured Obama, who was basically unknown at the time, would be thrilled that someone with so much experienceas well as so much wit and charm and talent!would want to come and work for him.

I was wrong; Barack Obama is tougher than that. He cared less about my credentials and more about the fact that I wasnt from Illinois. He wanted someone with a connection to his constituency, which I didnt have. I think he also wanted someone who wasnt too big for her britches, and he couldnt tell immediately how I fit into my britches. Literally or figurativelythe stress of a presidential campaign is not kind to the waistline.

But I really wanted to work for Obama. After the brutal Kerry defeat, I especially wanted to work for someone who was not going to run for presidentI didnt think I could take that heartbreak twice in a lifetimebut I also thought Obama was no bullshit and so, so smart. Even then it was clear he was special.

Id heard about the position from my friend Robert Gibbs, who had quit the Kerry campaign to work on Obamas US Senate race. One day after we lost, I was in the Kerry office, doing the very solitary, depressing work of making sure everyones invoices had been paid before we turned the lights off for good, when a message from Gibbs popped up on my AIM: What are you doing now?

I said I was wrapping things up, and after that, I didnt really know.

Do you need a job?

Yes, I did. I had been thinking about going on to work for John Kerrys PAC, but it wasnt clear Id get the role I wanted, deputy PAC director. Gibbs told me he was working for Barack Obama, who was really great, and that he thought I should interview to be his director of schedulinga senior adviser. Pete Rouse, a famous and beloved figure on Capitol Hill, had just signed on as chief of staff.

I told Gibbs I would look into it, and soon after, I met with Pete (who was wearing cowboy boots and jeans). He liked me and set me up to meet Obama.

Walking into the interview, I wasnt nervous, really. If youre nervous, you seem uncertain, and Ive always gone into interviews with the sense that, if it works out, thats great; if it doesnt, then it wasnt meant to be. Besides, Obama was wearing a black mock turtleneckit put me at ease.

It was a fairly run-of-the-mill interview, with Obama at the head of the table and me across from Pete and Gibbs, going over my life and my priorities. Why would I want to work for him when I wasnt from Illinois? And since I had just come from doing what was essentially a much more intense version of the same jobwith a very big staff and a lot to dowouldnt I get bored sitting around at the Senate all day?

I didnt feel like Id nailed it. Obama bid me farewell with a classic job interview move: Well be in touch. But if nothing else, I felt confident in my personalityat worst, I am good but difficult (and a tad sensitive), and at best I am assertive but laid-back, resilient with a righteous sense of humor. Even if I dont manage to get people to like me, I can usually persuade them that I am competent and not (too) annoying.

And thats how this story startswith the humble goal of seeming competent and not too annoying. Like most women I know, I ultimately want to be likable and trustworthyas well as glamorousbut its important to take baby steps. Though Pete later told me it had taken some persuading, Obama called and offered me the job.

I wrote a lot of this book during the 2016 Rio Olympics, and even though social media was around for 2012 and 2008, this years Games really felt like they were taking place online. If I didnt catch an event when it was on TV, it was pretty easy to figure out what had happened by looking on Twitter. And on Twitter, the commentary was much funnier.

One of the most iconic images from this Olympics was quickly turned into a viral meme by someone with 830 followers named @a7xweeman. The photo is really crazy: In the semifinal for the mens 100-meter dash, the Jamaican sprinter Usain Bolt, the fastest man in the world, is looking over his left shoulder as he pulls away from the blurry mass of his competitors, all of whom are pretty far behind him, and he is smiling. Huge. @a7xweemans caption for this picture was, *Record scratch* *Freeze frame* Yup, thats me. Youre probably wondering how I ended up in this situation.

I am 5 feet 2 inches and not a sprinter, or a runner, or an athlete; I switched to Pilates in 2006, after I nearly broke my teeth falling off a treadmill. (I was BlackBerrying.) Nevertheless, Ive often felt like this during my career: Yup, thats me. Youre probably wondering how I ended up in this situation. When you see my life on paper, its not remotely obvious how I would end up, at age 32, working as the right-hand woman to the first African American president, sitting across from him on Air Force One heading to Afghanistan, Russia, Chinaor, honestly, anywhere.

As I write this, I am 40 years old, not even close to the end of my career, and Ive already done more than I ever could have imagined for myself. I am a townie from Rhinebeck, New York; now, its a posh little weekend-getaway spot that appears in hashtags and cooking shows, but when my family and I moved there it had one stoplight, our road wasnt paved, and the chicken in a pita at Dels Dairy Creme was the pioneering predecessor of the artisanal farm-to-table movement. I graduated from high school with about 76 other kids. I was a good(-ish) student, but I was also a big fish in a small pond. My wardrobe consisted of flannels and Grateful Dead T-shirts, and my biggest accomplishment was surviving an impeachment as student body president, followed by my mean impression of Eddie Vedder. When I got a job as a checkout girl at Kilmers IGA Market, I was the fastest and most fastidious checker on double coupon day (do not try to pass off an expired coupon on me). I loved working the Wednesday before Thanksgiving because it put my bag-packing skills to the ultimate test.