So Here’s the Thing…: Notes on Growing Up, Getting Older, and Trusting Your Gut(24)

And if you’re already looking for a job, few things feel worse than trying to re-create your career history from scratch in a succinct, clear, and optimistic mood. Odds are if you’re in between jobs, you’re probably depressed and feel like shit. The last thing you want to do is pause the Real Housewives marathon to describe what you did as a paralegal nineteen years ago.





Things You Should Never Say to or Around Your Boss





“How do I get to be you by the time I’m thirty-five?”

“I want more substantive/meaningful work.” (Hate to break it to you, but filing stuff is really substantive! And your boss will probably think, or say, something to the effect of: I filed a lot of shit when I was your age. Why do you think you’re better than me?)

“I’ve been in my job for a year and I want a raise.” (Instead, start with your raise-deserving accomplishments, why you love your job and the company, and how you want to grow there. Then end on “I hope that we can talk about my future.” I personally like to give a raise as an investment, something that says I believe in the employee and makes them want to invest in me.)

“I’ve been in my job for a year and I deserve a raise.” (No explanation.)

“I want to manage people.” (Let’s talk about this. Why do you want to manage people? What makes you qualified to manage people? What people skills do you have? Are you diplomatic? Do you have the temperament? I have often found that people come to me and ask to manage people not because they think it’s a skill they have but because they see it as the quickest way to get a raise. The responsibility of shepherding people’s careers is not to be taken lightly! Some people are solo operators, and that’s a good thing! Also: Do you want to manage people just because it’s a power thing?)

Don’t tattle on other people to your boss unless someone is being a real problem.

Don’t comment on outfits your boss is wearing.

Don’t talk about your boss on social media. Even if he seems like the most Luddite manager ever, he will see it.





Ted Chiodo’s List of Words AM Uses That You Should Pay Attention To



Things on the 2007 Obama campaign could get crazy. Very crazy. As the director of scheduling and advance—SkedAdv—I was responsible for a matryoshka doll of schedules: My staff was my responsibility, and their responsibilities were other people’s schedules, which were also my responsibility, and the compatibility (or not) of all those schedules together was also my responsibility. Because of all the pressure, I had to be particularly careful to act like the kind of manager I’d want to have, not the kind I’d complain about with the rest of my coworkers at the bar. And that means restraining yourself and treating your employees with respect even when they make you want to tear your hair out.

So, like many managers, I came up with some ways to communicate that allowed me to express my feelings without taking them out on my employees. I’m not saying I was passive-aggressive—I loved them—but it was…reservedly tactful. Yeah. All bosses will get exasperated and drop their own version of these occasionally, but if you find yourself on the receiving end of phrases like this frequently, you probably need to shape up.

Because I spent so much time with my team, they eventually cracked my code. Which led to Ted Chiodo, whom I’d worked with since 2003, back when he used to wear pants with lobsters on them to answer the phones at Kerry campaign HQ, to send the entire SkedAdv team the following email. Edited lightly for grammar—no offense to Ted. Or TED, as he refers to himself in this dispatch:





8 WORDS OR PHRASES THAT TED CHIODO SHOULD PAY ATTENTION TO WHEN USED BY HIS BOSS, ALYSSA MASTROMONACO, BUT DOES NOT BECAUSE HE IS AN IDIOT


“Fine”: This is the word used to end a conversation when TED is usually wrong and needs to shut up. Or when things are not fine and are in fact escalating out of control.

“Five minutes”: This means, “TED, go sit back down. The thing you emailed me wasn’t that funny.”

“Nothing”: This is the calm before the storm. This means something, and TED should be on his toes. Conversations that begin with “Nothing,” usually end with “Fine.”

“Go ahead”: This is a dare, not permission. Don’t do it, TED. DO NOT DO IT!!!

[loud sigh]: This is not actually a word, but a non-verbal statement often misunderstood by TED. A loud sigh means AM thinks you are an idiot and wonders why she is wasting her time standing here and talking with TED about nothing. (Refer to (3) for meaning of “nothing.”)

“That’s OK”: “That's OK” means AM wants to think long and hard before deciding how and when TED will pay for being an idiot.

“Whatever”: “____ YOU!”

“Don’t worry about it—I got it”: Another dangerous statement, meaning something that AM told TED to do several times but is now doing herself. This will later result in TED asking, “What’s wrong?” For the response refer to (3).





Electric Chocolate Cream Pie Acid Test



It was one of those parties that gave everyone a story. The occasion was Jim Messina’s fortieth birthday, the location a speakeasy called the Gibson. Being a nerd living in DC, I didn’t understand what a “speakeasy” was in practical terms. I thought it just meant that the bar would be like a normal bar but more expensive, 1920s-themed, and have no sign above the door.