Who Thought This Was a Good Idea?

by Alyssa Mastromonaco

There is no bigger compliment than being intellectually curious about what someone else spends his or her days doing—it turned out that not having the answers did me no harm.

Whatever anyone tells you about how technology and social media have made us disconnected from reality is probably right, but I think you can boil all these kinds of arguments down to the fact that people are no longer chill. They are goal-oriented. They are aware of all the things they could or believe they should have. They are aware of all the things that could go wrong. This awareness makes a lot of things—dating, finding a job, dating a person you meet at your job, planning a trip for the president of the United States—much harder.

The best part about those jobs in high school—all of which I gained some satisfaction from and remember fondly, even if at the time I was thinking I would rather be watching 90210—was that they taught me a very important way to rationalize when my career seemed doomed or my life felt like it was veering totally off course: If I am never good at anything else, I know I am good at this. You might think that sounds depressing, but it’s given me a lot of comfort over the years.

There is no greater feeling of independence than being able to provide for yourself, knowing that if you really hate a job—and you will probably hate jobs at various points throughout your life—you can leave and be OK.

Being self-aware means knowing when you’re about to act bad—and then not acting bad.

In every crisis, you need a captain—a person who is constantly gathering all the available information, who knows the whole story and all its component parts, in order to make decisions holistically and keep everyone involved aware of what’s going on.

you’re always sort of nervous to get emails from people you want to get emails from,

but I had also learned that I acclimate pretty well, and that every job has a learning curve that you have to, ahem, lean into. Every time you change jobs, even if you’re coming in as the editor in chief or senior marketing manager or whatever, you will have first-day jitters. You will still spend an hour (or two) thinking about what you should wear. Those jitters don’t mean you’re about to fail; they’re what get you ready to dive into something headfirst.

One of my main goals in writing this book is to give you the permission to admit to feeling or doing things that are silly; once you do, you can get on with your life. So here it is, the real reason why I didn’t want to go down the street: The crew at the Hope Fund had been together since the Senate race in 2003. They were all friends, and I really didn’t want to be the new kid.

I wrote the political plan for the 2006 midterms. A political plan is basically the who/what/when of the year: key people Obama should be seeing, major events that we should be planning around, and how it all fits together so that at the end of the year you can say, “We wanted to get XYZ done, and we did.” (Or didn’t.) It’s also a very good way to make sure the most senior people and Obama are aligned on the mission.

I knew there would be another opportunity. I hadn’t always believed that, but the older you get, the more confident you can be about what you’re good at. The more places you can see where you belong.

Kindness often exists on a smaller scale than the grand gestures popular on social media would have you believe. Though anonymously paying off someone’s student loans or giving a waitress a $5,000 tip are amazing acts of goodwill, things like being willing to cut someone some slack, or making a thoughtful phone call, can help another person so much.