Why a Sleep Regimen Changed This Former Obama Staffer’s Life

By Alyssa Mastromonaco

Photo courtesy of Pete Souza

A question women often ask one another is: “What do you do?” It may refer to a skincare or exercise regimen, or a set of dietary restrictions, or how you manage to get out of the office with zero emails in your in‑box, but I think the question — which basically boils down to “How do you live your life?” — is rarely posed out of nosiness. Maybe it’s genuine curiosity (which is different from nosiness). Maybe it’s the compulsion to make sure that you yourself are on the right track. (Am I right to hate myself for waking up late?) Maybe there’s a little desire to steal some aspect of someone else’s routine for your own life. (How can I stop hating myself for waking up late?) Regardless, the answer is rarely uninteresting, even if it’s totally boring. Here’s what I do to stay prepared.

Photo courtesy of Pete Souza

(1) I always keep a list. I love a good list. I separate it into three parts: immediate goals, long-term goals, and personal. The immediate category usually includes things like paying bills, buying cat food, making a hair appointment, or picking up a prescription. The long-term list would include things like figuring out how to register my company in New York State, paying off my car (I did it!), planning a vacation, and getting tickets for an upcoming concert. The personal is basically just a list of friends whom, during the business of my life, I don’t want to forget to call, get drinks with, or track down to get our nails done. Something like “write this book” would end up falling in all three categories and listed three times so that I would maybe get the message.

Here is a sample list from today (August 15, 2016):

IMMEDIATE:

Finish chapter 6 with LO edits

Pay Q3 tax bill (need to find envelope/must drop in

Rhinebeck at dinner)

Go to PetSmart (need litter and more food for Petey)

Cut BunBun’s nails

Shower

430P call with Hope

Get train tix for this week

Put trash out

Leave by 515P for din with Mom and Poof

LONG-TERM:

Update chapters 1, 3, 6 with LO edits

Write chapters 4, 5

Email Souza about photos

Lock down Sept house for LO

Make list of improvements to Germantown house

See land in Germantown

Figure out Poof b’day present

Make hair appt

Get car washed

Try valerian root

Make Petey annual vet appt

Check to see if Ace+Jig coat has shipped

Check to see if No 6 clogs have shipped

Email Molly about CORA in Target

Connect with Sophie Walker

PERSONAL:

Book shit

Read The Girls

Less carbs

Photo courtesy of Pete Souza

(2) I put everything in my calendar. It takes so much stress out of my life to know where I can find things. My credit score went up 100 points when I started putting in reminders to pay my bills. I put birthdays in my calendar and set a three- day reminder in advance so I can put a card in the mail. (I keep birthday and all-purpose cards in the house at all times. And stamps. You should always have stamps.) I schedule reminders to pick up prescriptions or to make a dinner reservation at some bullshit hard‑to‑get- into place where you need to book a table 30 days out. Same for hair and gynecologist appointments — anything hard to schedule. I put my grocery list in my calendar. I almost always need 2% milk, Wheaties, watermelon, coffee, Coffeemate (don’t judge), and grapefruit juice, so I keep the list to remind me in case I happen to find myself at the store.

(3) Sleeping is good. For a long time, I was skeptical about those thousands of books that talk about the importance of sleep. When I worked at the White House, I started off going to bed at around 11:00 PM and waking up at around 5:15 AM, and because “going to bed” is different than sleeping, I probably slept only three to four hours a night. It was really after I turned 35 that sleep started having the greatest impact on my life, but keep it on your radar — you eat less, look younger, have a better attitude, and make better decisions if you get enough sleep. After I left the White House, even though by the end I was on a strict sleeping regimen, I was finally able to sleep in a meaningful way, and it changed my life.

(4) On traveling: No matter what I’m doing or where I’m going, I try to give myself as much time as possible to get there. (I am partially motivated to do this because I getstomach cramps or diarrhea when I cut anything too close.) If making an impression is important, I fly or take a train or drive the night before.

I also learned the importance of packing from Dey. (Dey, aka Danielle Crutchfield, was my deputy and suffered the same email traffic I did when things didn’t go according to plan.) When you’re working in the White House, you can traverse three distinct climates over the course of a trip, so packing is vitally important. On one trip, we started in Saudi Arabia, went to Egypt, stopped in Germany, and finally ended up in France. You will never go wrong with lots of layers and always covering your shoulders.

Because no one working in the White House had time to run around our apartments screaming, “Did I forget anything?” Dey had a packing checklist that quickly became legendary; after a year or so, we all used it religiously. Compression socks and a Snuggie (yes) for long flights. Granola bars for places with dodgy food. Tide pens. Bobby pins for countries with lots of humidity. Culturally appropriate footwear and dresses for state dinners in foreign countries. Once I accidentally packed a pair of peep- toe shoes on AF1 when we were heading to Saudi Arabia, and everyone made fun of me because I was afraid I would cause an international incident when meeting the king. (You’re not supposed to expose your feet.) It wasn’t the end of the world, but it wasn’t awesome. After being introduced to the packing list, I endured far fewer mishaps.

Also, I never have fewer than two tampons in my bag — One for me, one for a friend.

(5) On studying: The first lady was particularly adamant about state dinners: They were not just a fancy spread with free food and nice booze; they were work, and you were supposed to show up. Part of knowing how to be prepared comes from being self- aware — being able to anticipate what you’ll need (or screw up) and planning accordingly. I know

Photo courtesy of Pete Souza

I am rarely, if ever, the smartest person in the room. And that’s totally OK. What’s not OK is (1) not recognizing that and (2) not coming ready to participate in a meaningful way.

At state dinners, this meant knowing who you were sitting next to and reading up on a few things to talk to them about. Sometimes, this is awkward; at a state dinner for China, I was next to the commerce secretary, and although I’d looked him up online, there wasn’t a lot of information available. Finally, I dipped into my well of go‑to conversation starters, and since there was a musical performance at this dinner, I asked him what his favorite American song was.

He said it was “We Are the World,” so we spent the rest of the dinner trying to name all the musicians who sang on “We Are the World.” Long after we had given up, and he was talking to someone else, he looked back and me and shouted, “We forgot Cyndi Lauper!” Everyone was very confused.

If you don’t see yourself attending black- tie events with foreign dignitaries any time soon — though you never know — you can still take this advice to a job interview. When I’ve had to prepare for a job interview, I make sure to keep up on any news or current events related to the person or organization I’m meeting with. I read up, if I can, on my interviewer. It’s entirely possible someone who interviews you might not have Google results or be on Twitter, but if they are, you should know. At the very least, company websites usually have employee bios. The person will understand if you aren’t deeply acquainted with her stance on Bachelor in Paradise, but knowing her position in the company, how long she’s been there, and maybe even where she went to college (good for small talk) demonstrate a solid effort. Don’t go overboard in some psycho Instagram deep dive and open with “So I see your dog Chunk likes to eat rabbits,” or“You really enjoy Pilates!” — that would put you in the running for mayor of Creeptown. But if this person has a more public profile, scan a few articles about her. One of the best/worst/ most revealing job reviews I ever conducted was when, 10 or 15 minutes into the discussion, the woman stopped in the middle of what she was saying to exclaim, “Oh, waiiiiiiiit — weren’t you an Obama staffer for a while?”

I never started doing the type of work I do to become famous. But part of why preparedness is so important is that everyone knows you’re supposed to come to professional conversations with a couple of questions and a sense of whom you’re talking to. Everyone knows how easy it is to Google. The woman I was interviewing wasn’t living in a commune in the forest with no Internet access. Not knowing who I was didn’t make her look like an independent spirit or focused on her own work — it just made her look bad.

Photo courtesy of Pete Souza

Alyssa Mastromonaco is President Of Global Communications at A+E Networks and liaison to Viceland, A+E Networks’ cable network venture with Vice. Previously she served as Chief Operating Office at VICE Media, and prior to that as Assistant to the President and Deputy Chief of Staff for Operations at the White House from 2011–2014 and as Assistant to the President and Director of Scheduling and Advance at the White House from 2009–2011. Mastromonaco is a contributing editor at Marie Claire. She received her B.A. in Political Science from the University of Wisconsin, Madison in 1998.


From the book WHO THOUGHT THIS WAS A GOOD IDEA?. Copyright © 2017 by Alyssa Mastromonaco. Reprinted by permission of Twelve/Hachette Book Group, New York, NY. All rights reserved.