So Here’s the Thing…: Notes on Growing Up, Getting Older, and Trusting Your Gut(19)

Hmm… there was the time I almost threw my wine at the South Korean trade minister during a dinner in the presidential palace when he decided to share his opinions with you about unmarried women in their thirties, which you were at the time.

Who are the top five most interesting people you met while working for POTUS?

The pope, the Queen of England, Magic Johnson, Kanye (the old Kanye, not MAGA Kanye), and Muhammad Ali.

Can you confirm for everyone that David Beckham was making eyes at me the night we had dinner with the queen? What’s your favorite memory from that night?

There was no doubt that David Beckham had his eye on you. I know this because you told me approximately thirty-eight times that night, and once every few months (including in this question) in the seven years since. For all the Beckham talk from that night, I have a strong memory of you cornering Colin Firth and talking to him about Love Actually, which he was more than happy to discuss (seriously).

What makes me a good PLP? When did you know we’d be pals for life?

This is a hard question to answer because everyone is different, but I think the key to any lifelong friendship/platonic partnership is trust. Not just trust that someone will keep your secrets, but trust that they won’t judge you in your most vulnerable or needy moments. So many friendships and relationships are centered around an ideal image that one wants to maintain—the cool one, the calm one, the strong one—but that’s not how life is. You need to feel 100 percent comfortable putting down your guard and being your most authentic self, even when it contradicts the person you want people to think you are.

I always tell people that you saved my life literally and figuratively. Literally by getting me to a hospital in an Uber when I had a blood vessel constricting blood flow to my brain, and figuratively because I never would have survived two years on a presidential campaign and six years in the White House without having you there to give me advice when I needed it, make me laugh in the dark times (personal and professional), and give me a swift kick in the ass when I was being dumb. If I hadn’t been willing to share with you my most embarrassing moments, my greatest fears, and my craziest insecurities, I wouldn’t have made it. You never once made me feel bad or embarrassed about my darker moments. No one could ever ask for a better friend.





“How Do I Get to Be You by the Time I’m Thirty-Five?”



What are gut feelings, and how do you use them? We all want to know the secret to success, and we all want the secret to be “It’s really easy, actually.” So when we see someone we consider successful, we immediately think they can tell us the one easy trick to becoming successful ourselves. But the truth is it’s very hard. Or at least it was for me. Too often, advice is understood to mean “telling other people what to do.” But beyond “life hacks,” good advice is entirely situational. Don’t get me wrong—I love a good hack. (The thing Sophia Amoruso says about wearing a tampon when you go commando—life-changing.) But you can’t hack your way to a fulfilling career.

Nevertheless, as my career has developed and become more “public-facing,” young people approach me asking for advice. The way they phrase it is usually something like: “I want to be you by the time I’m thirty-five.”

I’m sorry—I know it’s well meaning. But “I want to be [insert renowned other person] by the time I’m thirty-five” is the worst way ever to approach your life. I would not have been me by the time I was thirty-five if I hadn’t been open to random opportunities that presented themselves unexpectedly. I would not have been me by the time I was thirty-five if I had a list of characteristics and accomplishments that I thought defined who “me” was.

The message I wanted to get across in Who Thought This Was a Good Idea? was that there’s no path, and even if there were, you certainly don’t have to follow it. To me, an instinct is a good way to balance what you need to do with what you want to do. You may feel pulled in one direction or another, but deep down you know what’s right. When you have to consider both your dreams and your nightmares, your passion and practicality, practicality usually wins out, until it doesn’t have to anymore.

No one can do what I did by being safe, and you can only take risks if you’re relatively financially independent. Every component of good decision making—risk taking, trusting your gut, setting priorities—is contingent on your ability to take care of yourself. Even if we look at industries we think have clear, step-by-step procedures for reaching a senior position—investment banking, say—women rarely have opportunities to make it that far. Women are 18 percent less likely than men to get a promotion to management level, and from there their numbers in senior positions drop.

This is scary, but it’s also exciting. You can’t figure out how to get where you want to go without first figuring out where that is. “Success” is not a place. “Success” is everywhere and nowhere at once. It means wildly different things to different people.

Here is my trajectory, in more or less chronological order from around age fourteen, for proof:

Babysitter; bagger at Kilmer’s IGA; cashier at Del’s Dairy Cream; cleaner at the Beekman Arms hotel; hostess at the Beekman Tavern; babysitter; unpaid intern for Rep. Bernie Sanders; hostess again; audio transcriber for Ed Garvey, a progressive icon who unionized the NFL; babysitter; congressional intern for Rep. Bernie Sanders; babysitter again; real estate paralegal; secretary at Merrill Lynch (for five days); assistant at a very random start-up company; client relations person at Sotheby’s; all-around staff assistant for John Kerry; babysitter; associate at a Republican lobbying firm (I can explain!); press secretary for Democratic congressman Rick Boucher (from Virginia’s Fighting Ninth!); director of scheduling on John Kerry’s presidential campaign; adviser (and then political director) to Senator Barack Obama; lots more with Obama; White House deputy chief of staff for Obama; chief operating officer at Vice Media; New York Times–bestselling author; president of global communications for A+E Network; podcast host; and now…TBD.