So Here’s the Thing…: Notes on Growing Up, Getting Older, and Trusting Your Gut(23)

My business cards.

Two photos: one of me on Air Force One headed to Iraq in a sandstorm, surrounded by dudes, and another of me pretending to be a hedgehog to make POTUS laugh.





Quitters Sometimes Win



Quitting fucking sucks. It doesn’t matter if you’ve loved your job or hated it—change is hard, and no one likes being destabilized, unsure of what’s going to happen next. Gone are the days when you were selling fudge at the Dutchess County Fair and felt so overwhelmed by your hatred for it that you sent your best friend in to quit for you. (You know who you are!)

No: Most of the time, how you leave a job matters as much as how you come into a job. Social media and the general lack of privacy we have now mean that your potential employer can talk to your past employer easier than ever, and your reputation can precede you more than you anticipated. Even if you want a career in fashion and you’re working at a plastic-supply company, you’re still forming connections and generating recommendations you’ll need for the rest of your life. And they often hinge on how you act when it’s your time to go.

Once you start daydreaming about quitting on the reg, you’re in the danger zone. (The same is true of relationships: Once the idea of a breakup comes to you, and you imagine yourself sipping cosmos with the girls on a singles’ vacay, it’s hard to turn back.) When I’ve gotten to that point, I’m usually bored, annoyed by coworkers, exhausted, no longer interested in the mission of the company/organization, and probably already looking elsewhere.

When I left the White House, a mission so much greater than I could ever really wrap my brain around, it was because I was depleted. It took me a long, long time to recognize this. How could I get sick of that mission? It was the mission of the United States of America! Slowly but surely, though, I was becoming the person I found annoying: the person who could explain in painful detail all the solutions that had been tried before and why they all failed. A combination know-it-all/hater.

If you’ve never reached your breaking point with a job, you’re probably thinking, Isn’t that a good thing? You can anticipate problems!

Not really. I wasn’t being productive. If you’re trying to find new and interesting ways to communicate what the intentions of the president’s policy proposals are in a burgeoning era of “new media”—that’s what we called it back then—you have to be willing to try new things, think out of the box, and fail before you hit it out of the park.

Back in 2014, for example, when we were brainstorming ideas for reminding people about the open enrollment period for the Affordable Care Act, VJ and Pfeiffer wanted POTUS to appear on Between Two Ferns with Zach Galifianakis. I was so against it. “This isn’t ‘presidential’!” I cried, scowling at my desk. From our deeply uncomfortable vantage in the Trump era, you can LOL all day long. But back then I felt I was in the right. Presidentiality was important. It was an institution. It was continuity. Never mind that Between Two Ferns was hugely popular and hilarious. I had no idea what it was, and I wasn’t about to google something so stupid.

I just checked, and today the segment with Obama has over twenty-five million views. It was one of the most successful tools for getting the word out about open enrollment.

Progress usually needs fresh eyes, and despite my love and admiration for President Obama and FLOTUS, and my devotion to the squad, which had been together for so long, I knew it was time for fresh eyes. I owed it to the man who gave me the opportunity of a lifetime and also, tbh, to the American people. I also wanted to leave on a high note, not after people got so annoyed with me that they started shit-talking my bad attitude and lack of vision behind my back. The idea of walking into a room and seeing everyone abruptly end their conversation because they’d just been saying I had been a bitch in the 8:00 AM meeting was brutal.

Telling POTUS that I had to leave—and then actually leaving, which took much longer than I thought it would—were probably two of the most difficult and emotional things I’ve ever done. But I wasn’t wrong, and have never regretted it.

If you have a good relationship with your supervisor, tell her how you feel. It’s important to not do the French exit if at all possible. If there are other positions in the company that you’re interested in, talk about it. If there aren’t, explain what you’ve enjoyed about the job, where you see your future, and why you think it’s time for a change. Most decent people would rather help you land your next gig than deal with a miserable and dissatisfied grouch. (And if you threaten or even just pose quitting and your supervisor offers you a meager raise: Don’t take it. If you stay, you have to recognize she called your bluff, and she owns you.)

Sometimes we quit because we can and we want to. Other times it can be more complicated. The job may become impossible because of people in the office—no judgment. Regardless, you should always have an updated résumé, something in progress where you keep track of when each position ends. Every couple of months, give it an eyeball, gussy it up, and make sure it’s good to go in case you need it. I’ll be totally honest: I don’t have one right now. Because I thought I was hot shit and didn’t need one anymore. But it turns out that even recruiters for the most senior positions will ask you for a CV, and if you don’t have one, it’s not going to make you look important and cool—it’s just going to make you look unprepared.