Thanks, Obama: My Hopey, Changey White House Years

But I was lying. In truth, the mood was awful. We slouched through the EEOB’s hallways. We plodded across West Exec. It was as if every White House staffer had been simultaneously broken up with.

And in a way, we had been broken up with. The most pressure-packed workplace in the country was no longer located at 1600 Pennsylvania Avenue. Overnight, the center of the universe had left us for a nondescript building in Maryland, the headquarters for our heroic team of nerds. I rooted for what reporters were calling “the tech surge.” I wanted it to succeed. But on a more personal level, I wanted life to go back to normal. I wanted the White House to feel White House-y again.

Part of me doubted it ever would. Websites can be fixed, but the damage to Obama’s movement would be far more difficult to repair. In Washington, you often hear people say that “perception is reality.” I usually like to imagine these people walking through plate-glass windows. This time, however, they had a point. After our shutdown triumph, the Obamacare rollout was supposed to be the knockout punch. The battle over the size and scope of government—an argument decades in the making—would be settled once and for all.

Instead, thanks to unforced errors, our greatest victory had become our most catastrophic defeat. To the press, Obamacare would be forever mired in controversy. To the law’s opponents, Healthcare.gov would be a symbol of government’s inability to do anything right. It was disappointing. It was infuriating. More than anything, it was exhausting. Sure, we were on the right side of history. But would we ever actually prevail?

Perhaps it sounds corny, but what kept me going was Zoe Lihn. “I refuse to walk away from forty million people who have the chance to get health insurance for the first time,” said POTUS, and despite my growing doubts, I agreed with him. I thought about Zoe’s mom, Stacey, standing on that Charlotte stage. I thought about Wendy, my Ohio volunteer, pacing our campaign headquarters despite near-crippling pain.

And I thought about Jacqui. A year earlier, after earning her law degree, she had graduated into one of the toughest job markets new lawyers had ever encountered. While she found work that paid decently, it didn’t come with benefits. She was uninsured.

I should add that Jacqui was in perfect health. Her situation was nothing like Wendy’s or Zoe Lihn’s. Yet this was precisely the point: my girlfriend was one of the lucky ones, and her lack of coverage was something we worried about literally every day. The night Jacqui first met my family, we were walking to a bar in Brooklyn when my sister accidentally brought a spike heel down on her foot. More than her pain, I remember her panic. Was something broken? How much would an emergency room cost? Could we set a bone using duct tape and WebMD?

There we were, two well-educated professionals in the richest country on earth, wondering if we knew how to jury-rig a splint.

OUR A-TEAM OF CODERS COULDN’T UNDO THE DAMAGE TO THE president’s credibility. They could, however, make Healthcare.gov suck less. By mid-December, the site’s error rate was under 1 percent. In speeches, we urged Americans to try signing up online.

In private, however, I advised Jacqui to wait. Engineers were still fixing faulty code. The insurance wouldn’t actually kick in until New Year’s. Why not give it more time?

Specifically, why not wait until Christmas? Two years into our relationship, I had finally promised to spend Jacqui’s favorite holiday in New Jersey with her family. I saw this as a gesture, like telling an English friend you’ll go with him to watch a soccer game. She saw it as a full-blown embrace, like telling an English friend you’ll tattoo Saint George’s Cross on your forehead and beat a Scotsman with a pipe.

Thus my real reason for suggesting Jacqui wait to buy insurance. If the Christmas spirit overwhelmed me, I could always count on Healthcare.gov to darken the mood. Driving north on the turnpike, we listened to “Grandma Got Run Over by a Reindeer,” and I casually wondered who paid for Grandma’s outpatient therapy. A nativity scene became an excuse to mention that, thanks to the Affordable Care Act, pregnancy was no longer a preexisting condition.

And yet, despite my determination to be a wet blanket, Christmas charmed me. It wasn’t just the presents and pajama-clad mornings. Beneath the cheer and sleigh bells, I found a web of often-contradictory traditions. Layers of familial angst needed managing. There was the constant sense that one’s celebrating was not quite celebratory enough. And to think I worried about fitting in! Pork products notwithstanding, Christmas was the most Jewish thing I’d done in months.

Lost in piles of wrapping paper and mountains of spiral-cut ham, we nearly didn’t get around to health care. But once Christmas Day was over, we decided it was time to take the plunge. On the night of December 25, 2013, Jacqui and I closed the door to her childhood bedroom. Then, cautiously, we opened Healthcare.gov.

When speechwriters sought out Real People for POTUS remarks, we tended toward the dramatic: hero firefighters, single moms returning to college, wounded veterans beating the odds to recover. If an anecdote wasn’t extraordinary (or, as often happened with midwesterners, the RP was frustratingly humble), I wasn’t above teasing out a quote.

“So, would you say getting hired at the Chrysler plant made you believe that, in America, anything is possible?”

“Uh, I guess so.”

“No, really. Would you say it?”

What I had forgotten, until I myself became a real person, were the countless far less dramatic stories that begin with a decision a politician makes. Red light cameras are installed to compensate for a budget shortfall, and suddenly you’re opening a ticket in the mail. A trade deal stalls in Washington, and a dentist in Malaysia buys a Hyundai instead of a Ford. A president makes health care reform a priority, and five years later a pair of twenty-somethings sit on a twin bed, wondering if their relationship will survive history’s most infamous online store.

The first step, creating an account, went smoothly. But if signing in was easier than expected, what followed was hopelessly complex. To help you pick the right insurance plan, the site asked a series of questions. These reminded me of the “would you rather” game I used to play on the middle school bus. Would you rather fart every time you blink or have hiccups forever? Have no nose at all, or a second nose on your butt?

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