Kal Penn Kind of Promised to Have an Obama Holiday Party at a DC Strip Bar | #emailsecurity | #phishing | #ransomware

In 2009, after a stint with the Obama campaign, actor Kal Penn took a break from Hollywood and spent two years in Washington working for the new President. As it turned out, the star of the Harold and Kumar franchise found plenty of comedy in the bureaucratic doings of DC. In an excerpt from his new memoir, he pens a letter to his 31-year-old self—a summation, as he puts it, of “how many of the things I learned at the White House would have been good to know before going in.”

Penn applied for the job via Change.gov—a rookie move for a campaign vet. “You did what?” Michelle Obama asked when she learned that. Photograph by Pete Souza/Official White House.

Tip A: Invest in a Mini Fridge

We both know you have a tendency to get hangry, so let’s talk about the culinary situation. You’re not in Hollywood anymore. There’s no catering, and there are no production assistants, so no one is ordering you a vegan burrito with fair-trade, organic, shade-grown coffee at 10 am. Also, 10 am is super-late in Washington. Make yourself some oatmeal before you leave home.

Lunch is easily brought or bought, but since your workdays will usually end between 8:30 and 11 pm, plan ahead for dinner. Unlike what you saw on The West Wing, forget about delivery. Sure, the cooks at G Street Food seem nice, but the Secret Service won’t allow it because adversaries working at nearby restaurants could decide to poison your meal when they see where it’s going. More bad news: The area around the White House becomes a gastronomic dead zone after 6 pm. So, you’ll have to do what normal people across this great nation do every day: pack a dinner from home.

Go to the Target in Columbia Heights on a Saturday. Ask your intern James to help you bring a mini fridge back on the Metro, through Lafayette Park, and into the northwest gate. He’s going to be comically bad at lifting things and you’re going to want to yell at him a little, but this is not Hollywood and you’re not an actor, so you can’t throw tantrums to get your way. Be nice. Don’t be intimidated by the Secret Service guys on the White House roof with sniper rifles: Yes, you’re two dudes with a big box trying way too hard not to look suspicious, but . . . you have your badge.

One final tip: In emergency situations only, you can head down to the basement and pick up a vending-machine sandwich. The cheese option is the most edible and consists of two slices of (allegedly) yellow cheese on (supposedly) white bread with (purportedly) mustard-colored mayo. For me, your future self—don’t eat too much of this stuff. Your friends in Hollywood would be horrified if they found out you consumed white carbs.

Penn was acting in the fifth season of House when he got the DC gig, and his character was killed off so he could take it. Photographs, from top, by Charles Dharapak, Pete Souza, and Dan Spilo; all courtesy of Simon & Schuster, Inc.

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Tip B: How to Hang Things on Your Office Wall

You’ll want to be reminded of Grandpa’s legacy of public service each day as you begin your own. So, bring in Grandpa’s photo of Gandhi to hang on your office wall. A coworker will politely inform you: “You aren’t allowed to nail anything to the walls, Kal. You’re going to have to call GSA.”

You’ll think to yourself: Okay, no problem, I’ll just call GSA and be good. Not so fast.

Step One: Fill out a Work Order form, found on the office intranet. Print it, sign it, and go downstairs to the room where Work Order requests are filed.

Step Two: The door will be locked. Come back later.

Step Three: The door will still be locked. Someone will casually mention that the woman who processes those forms has worked in government for decades and accordingly accrued a lot of time off. She usually comes in around 10:30, takes an unnecessarily long lunch, and leaves by 3:30.

Step Four: Wait a full day. Don’t worry, pal, that picture is going to look great.

Step Five: The next day, schedule your meetings around Five-Hour-Workday Lady, and you’ll finally be able to complete Step One: dropping off the form. Great job!

Step Six: At some point, you’ll get an email asking when you can be available for a call (Step Seven, below) to talk about the request (Step One) you have put in (Step Five) for the photo you want to hang. You can complete Step Six by replying to schedule the call (Step Seven) for the next day. Hello, Gandhi!

Step Seven: The following day, somebody will call to confirm the details you have already listed on the (Step One) form: How big is the photo? How heavy is it? The Step Seven human will eventually ask to schedule a time when (Step Eight!) he can come by. He’ll be booked for a few days, so go ahead and save yourself some time by scheduling for the following week.

Step Eight: When half a fortnight passes, a nice man wearing an exceptionally large tool belt will show up and complete the final step—he’ll hammer a nail into your wall. Then he will leave. Oh, you thought he’d hang the picture, too? Silly, silly, Baby Kal. He is Captain of the Nails. It’s your responsibility to hang the picture. Welcome to the federal government, buddy.

Now look, you can do all of that . . . or . . . make things more efficient. Take a peek behind your office door. You’ll see a stray nail in the corner—left over from when some past staffer took down a picture. Wait until everyone has left for the night and yank it out. Use your stapler to bang it into the wall, and hang that photo, homie! After all, your grandparents marched with Gandhi because they were idealistic. They weren’t rule followers.

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Tip C: Work Email Is Not Like Personal Email

You work for the Office of Public Engagement, and because a lot of good people pin their hopes and dreams on what’s happening at the White House, your inbox will be inundated. When it comes to constituents whose organizations you’re working with, be sure to read between the lines of email signatures. Legit people don’t need to prove themselves with the girth of their signature. (Yes, that’s a euphemism. I can make dick jokes again, but you shouldn’t. Not a great look for a White House staffer.)

Speaking of euphemisms and dick jokes, let’s discuss internal emails. You’ll often be looped into large-group chains, many of which will require quick responses or dedicated decision-making throughout the day. Others are just for situational awareness. One day, the National Security Council (NSC) will email you and 80 others a memo with talking points about an upcoming visit by a delegation from the Philippines. It’ll be your first NSC loop-in.

I want you to know that almost everything in government is an acronym.

The memo will include several pages of talking points, but you’ll be super-obsessed with item 14: “One of the main terror groups in the Philippines is the Moro Islamic Liberation Front (MILF).”

Your hopes are confirmed by the next few bullets:

• MILF is considered highly dangerous.

• MILF has a long history of recruiting young men.

• Many young men who join MILF come to regret their choice, as the novelty of life with MILF wears off.

Listen. You can only laugh to yourself about a terror group named MILF. Don’t make the same mistake I made. Do not reply-all. Don’t write, “Whoa, their main terror group are the MILFs? Amazing!” If you do this, the chain will go silent for 30 minutes before an older NSC career person will also reply-all with the message “Looks like Kal Penn is in the building.”

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Tip D: Nobody Is Crazy

Try not to use the word “crazy” in describing anybody. Just as in Hollywood, nobody in the political world is actually crazy. People can have colorful personalities. They can be eccentric. They may have unconventional views. You can say something like, “Wow, Anthony from that think tank sent me a passionate email about the President’s foreign-policy strategy” or “Anthony from that nonprofit has such a peculiar take on leadership!” People in DC will know that you actually mean Anthony is 100 percent completely batshit crazy.

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Tip E: White House Snail Mail Is NOT Like Fan Mail!

Passionate emails with girthy signatures can be annoying. Colorful snail mail . . . now that’s just fun! In your old life, your publicist weeded out the weirdest notes from fans. Now the Secret Service handles this, and they’re filtering for anthrax, not for crazy.¹ So, get used to the following:

• Trash (yes, actual, physical garbage).

• Tiny bits of paper with nonsensical slogans scribbled on them, including gems like “Nocturnal challenges await the waited.”

• Rants from people claiming to be inter­galactic commanders.

• A weirdly stapled packet of photos, including pics of someone’s great-grandfather and the handwritten caption “This is my house. Here are the directions. You can come over and I will cook you yummy Indian food.”

• Really sweet notes from former ambassadors with absolutely incredible names.

It doesn’t feel this way, but you’re getting a window into America: a place with would-be intergalactic commanders and (Ambassador) Dick Swett. Appreciate these notes. You’ll miss them when you go back to acting.

¹ It’s fine to use it here.

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Tip F: Be Attentive, and Be Careful What You Agree To

One day, you’ll need a haircut. You’ll Google “Barber, Dupont Circle DC.” Raucous Rodolpho will have an opening right away.

“Kal! Penn!” he will shout, staring at you in the mirror. “Wow, man, it’s really you! How’s Obama?”

DC is a smaller city than most people realize, and word about hirings and firings spreads quickly. Raucous Rodolpho will have heard about your job. “I’m askin’ ’cuz I’m not just a barber, man, I own a tapas bar too, you need to come check it out, man! And hey! You should bring Obama!”

Always politely decline these kinds of invitations. Good-natured as they are, they’re also against the Obama World rules:

• Keep all work and personal emails separate.

• For your protection, always hide your security badge after you exit the complex.

• Don’t accept free anything.

That last one is a biggie. The President and senior staff had to turn down watches gifted to them by the king of Saudi Arabia. You’ll need to decline the free-tapas-bar invite.

Explain the situation to Raucous Rodolpho, who will double down: “Look, man. I’m a small-business owner from a minority background. I got this barbershop, and I got my tapas bar. It would be an absolute honor to have you guys there. If you can’t accept anything for free, I’ll charge you. I guarantee . . . you’ll all have a great time.”

“I’ll tell you what, man,” you’ll say, eager to change the subject, “why don’t you give me your card. If we’re planning a staff holiday party or event that needs a bar, I’ll definitely give you a shout.” Raucous Rodolpho will light up.

That night, you’ll empty your pockets: keys, some change, and Raucous Rodolpho’s card. You’ll look at it for the first time: a glossy black background with a long, thin drawing of a barber pole running down the center. Why is there a naked woman swinging on that barber pole? Just underneath her exposed cartoon breasts, you’ll find the name of the tapas bar in shiny letters. This is where you agreed to potentially have the White House Office of Public Engagement holiday party: RODOLPHO’S LADIES: TOPLESS BAR.

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Tip G: Be the Best Gatekeeper You Can Be

You’ll be putting together meetings and briefings for POTUS that include community leaders from outside the White House world. That can turn into a bit of a process.

You have to give their Social Security number to the Secret Service for a background check. Then their online and offline profiles are analyzed by the research team to make sure there’s nothing offensive or otherwise potentially distracting. That department will be led by a woman named Liz Jarvis-Shean. Be good to Liz. She’s a saint. She also has a couple bottles of really nice Scotch, which she’ll share with you on especially late nights at the office.

In a couple years, you’ll be planning a young leaders’ roundtable for the President during a visit to Iowa. You’re going to remember that energetic kid, Romen Borsellino, who put together Obama’s first-ever high-school surrogate event during the campaign. You’ll want to tap him for this meeting.

You’ll send Romen’s vitals to Liz, and she’ll email you a couple days later:

FROM: Liz Jarvis-Shean

TO: Kalpen Modi

SUBJECT: Romen Borsellino

In the middle of vetting for your Davenport event. Can you please have Romen Borsellino delete the tweet below?

You’ll stare dumbfounded at your screen, trying to come up with a reply, when the phone will ring. It’s Liz, and besides the cum-thesis problem, she’ll bring up something Romen has on Facebook.

Photograph of Borsellino by Kesa.

Laugh your face off, then send Romen a cryptic message asking to talk “about something important.” You’ll catch him on a drive, and he’ll be nervous. Play this up. Do not let on that you think any of this is funny. For example:

ME: I just got part of your vetting report back. There are a few problems. I need you to take down a Facebook photo . . . the one with the dildo.


ME: Hello?

ROMEN: Yeah.

ME: You have to take down the photo. The one with the dildo.


ME: Can you hear me? On your Face­book page, there’s a photo of you with a giant dil—

ROMEN: —Yeah. Will do.

ME: There’s also a tweet. About somebody getting cum on his thesis.

ROMEN: Oh, God . . . just so you know, that means cum laude. My friend Nihal got cum laude on his thesis. It was a congratulatory tweet.

(He’s trying to negotiate with us?!)

ROMEN: So, can I leave that one up?

ME: If a journalist asks, can you and Nihal prove that he got cum laude on his thesis, and that it happened right before you tweeted?


ME: Okay, I guess you can leave it up.²

Try not to laugh. Thank him and end the call. Having successfully “cleaned up his digital footprint,”³ Romen will be cleared for the meeting. It’ll be a few more years before you find out that he had the dildo because he was a student health educator who taught students how to properly apply a condom. Or so he claims.

Anyway, congratulations. With Liz’s team’s help, you’ve avoided a Fox News headline like MUSLIM “PRESIDENT” HESSEIN-OBAMA MEETS WITH DILDO-MANUFACTURING, CUM-TWEETING TERRORIST.

Don’t let them make your boss the butt of a dildo joke. See what I did there? Future you has still got it.

Kisses, Kal

P.S. If President Obama asks your advice on whether he should wear a blue or a tan suit to his August press briefing, for the love of God, don’t say, “Tan seems kinda fun.”

² It’s still up.

³ A fancy, political way of saying “deleting dick pics.”

Photograph courtesy of Simon & Schuster, Inc.

From “You Can’t Be Serious” by Kal Penn. Copyright © 2021 by Bhai, Inc. Reprinted by permission of Gallery Books, a division of Simon & Schuster, Inc.

This article appears in the January 2022 issue of Washingtonian.

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