The Career Comedown

After leaving the job of a lifetime as an Obama White House insider, ALYSSA MASTROMONACO relates how she lost and then recovered her sense of purpose after such a defining role, and how she is adjusting to a life more ordinary.

- Alyssa Mastromonaco

You’re probably wondering how I ended up in this situation. When I interviewed for a job — it started with director of scheduling — with Barack Obama, it didn’t feel like I’d nailed it. Obama bid me farewell with a classic job interview move: “We’ll be in touch.” Even if I don’t manage to get people to like me, I can usually persuade them that I am competent and not (too) annoying. So that’s how I started — with the humble goal of seeming competent and not too annoying. Like most women I know, I ultimately want to be likeable and trustworthy — as well as glamorous. Obama called and offered me the job.

In my time at the White House, I felt like I needed to overcome ageism more than sexism. I was young, but people had been young there before. Yet I always felt when I walked into the room, it was about me being the youngest person at the table, and that I needed to come off as being more serious. I will be the first to say I go through periods of insecurity, but when I was promoted to deputy chief of staff, I was so worried I might fuck up and that, if I did, really bad things would happen, that I went into my boss-slash-mentor and said, “I think someone else should do this job.” And he replied, “You’re the only person who thinks you can’t — the President thinks you can, the Vice-President thinks you can.” That snapped me out of it. My complaining had the tone of, “Stroke my ego, tell me I’m amazing.” It didn’t take me long to realise I have a lot to offer and people who were there through all the administrations were there to help and really did want us to succeed.