With all the talk about what this week’s convention speeches need to achieve, I thought I’d offer some perspective on what a shitshow it is to be involved in writing one.

Tomorrow night, Barack Obama will address what is likely to be his biggest audience between now and the end of his presidency. He’ll do so at the Democratic National Convention, where America first met him as a 42-year-old state senator exactly 12 years earlier.

It’s where I met him, too. The day before Obama was scheduled to deliver the keynote address, he was practicing the speech on a teleprompter (a device he’d never used before) in the Boston Celtics’ locker room, which is where all the speakers rehearsed that week. Halfway through his session, I interrupted — a 23-year-old speechwriting asshole from the Kerry campaign who had been sent to do the dirty work of my superiors: ask Barack Obama to change a line in his speech that John Kerry wanted to use in his.

I was, of course, terrified. I could barely get the words out. “But that’s one of my favorite lines,” he said, with a “Who in the hell are you?” look on his face.

It was entirely justified. The original line ended the speech’s now-famous red state–blue state riff, and went something like this: “We’re not red states and blue states, we’re the United States, all of us standing together for the red, white, and blue.” I bumbled through an explanation worthy of Meredith McIver about how Kerry had supposedly written a similar line, when I was saved by a tall, mustachioed man named David Axelrod.

“Son, why don’t we step outside and rewrite the line together?”

We did, it worked, Kerry lost, Obama won, and in January of 2005, I was hired as the Senator’s first speechwriter — but only because Obama had absolutely no idea that I was the same kid who had interrupted his rehearsal.

Months later, a group of us were reminiscing about the convention when Obama said, “Remember that little shit from the Kerry campaign who made me change the line?” I confessed. “What?” he exclaimed. “I would’ve never hired you.”

I waited.

He laughed.

I exhaled.

Four years after Boston, I found myself working with Obama on another convention address. This time, it was an acceptance speech for the Democratic Party’s presidential nomination. And as I sat through the first meeting about the speech with the candidate and all of the campaign’s senior advisers, I became even more terrified than I was in that locker room.

“We need to tell Barack’s story.”

“We have to draw a sharp contrast with McCain.”

“He should lay out his vision.”

“Voters want specifics.”

“Let’s go big.”

“Keep it short.”

I had never written a speech this big or complicated. Neither had anyone on my young team of speechwriters. Neither had Obama, really. The stakes just weren’t as high for him in 2004. They might have been for his 2007 Jefferson-Jackson Dinner speech, or his 2008 race speech, but the former was only 20 minutes in length, and the latter was intensely focused on a single issue. An acceptance speech needs to do a lot of business in a relatively short amount of time, and the danger in a speech about everything is that it becomes a speech about nothing — a paint-by-poll-numbers checklist of issues, cheesy slogans, and born-in-the-middle-of-middle-class-America biographical clichés.

Oh, and we were also in the middle of an election that was far too close for comfort, with plenty of Gallup-induced bed-wetting reminding us daily that a loss in the general would be a much, much bigger deal than a loss in the primary, which we weren’t ever supposed to win, anyway.

As the meeting went on, I was inching towards panic when I heard the voice that always calmed me down at times like this:

“We’ll be fine. We’ve still got a few months, and I’ve got a pretty good idea about what I want to say. I’ll download some thoughts to Favs, and we’ll get a draft going soon.”

Obama. Always the calmest person in the room. I never knew if it was an act intended to keep the rest of us calm, but I also never cared, because it worked.

At least, it worked temporarily. Birthing a solid first draft was a fairly miserable experience. I tried to lock myself in a closet during the day, but there was too much other work and breaking news, so I’d stay up every night, writing as late as I could in our Chicago headquarters without falling asleep. After a few weeks, I sent an early draft to Axelrod. I didn’t take it as a good sign when he called back and said, “So I do like what you’ve done here on page eight.”

Axe is a political genius, a brilliant writer, and one of the kindest people I’ve ever met. His judgment as to whether or not a speech hit the mark was almost always accurate, but because he spent the campaign on the road juggling 10 projects at once, it was difficult to extract the constructive part of his criticism. “It just needs to be bigger,” he would often say. “It feels like we may have missed the runway” and “You should take another look at that 2004 convention speech” were also favorites.

At that point, I asked the rest of our speechwriting team if they would save me, even though they were all busy writing speeches for Obama’s three finalists for vice president: Evan Bayh, Tim Kaine, and Joe Biden. The team, including Ben Rhodes, Adam Frankel, and Sarah Hurwitz, retreated to Cody Keenan’s parents’ place for the weekend, and we wrote together. We wrote riffs defending Obama from John McCain’s attack that he was a celebrity, we wrote riffs about the true meaning of patriotism, and we started to write the end, which began with an allusion to Dr. Martin Luther King Jr.’s March on Washington, an event that took place exactly 45 years before the night Obama would accept the nomination in Denver. In order to include that allusion, I had to fight with a number of our consultants, who were concerned that referencing King would hurt our efforts to attract white voters, an argument that Axe, campaign manager David Plouffe, and Obama found as absurd as I did.

We sent our draft to Obama a week before the speech. On the Saturday before the week of the convention, he locked himself away in a Chicago hotel room to work on it. Late Sunday night, he emailed his draft. Per usual, the many pages he’d written added depth, passion, brilliance, honesty, inspiration … and length. So much length. The draft was nearly twice as long as the one we’d sent him. It would’ve taken him 90 minutes to deliver, maybe more. And the speech was Thursday. I tried not to panic as I read his note: “I know it’s too long, but we’re good at cutting, and we have plenty of time to get this thing in shape. See you on the plane tomorrow morning!”

I’m not a good flyer. I do it, but I hate it. To me, every bump or dip is a sure sign that we’re headed straight into the side of a mountain. It was entirely predictable, then, that the first legs of our preconvention swing would be horribly turbulent — and that was the only time I had to essentially cut the speech in half.

At some point during our flight to Montana, Obama fell asleep. Axe did too. The only person awake in our cabin was Senator Jon Tester, who must’ve wondered why the insane-looking kid with the laptop across from him was drenched in sweat and rudely refusing small talk. Still, I managed to cut large sections of economic and foreign policy wonkery that belonged in a Brookings lecture, as well as big portions of our original draft, and got the speech down to a manageable length by the time we landed (there is a picture of me floating around the internet where I’m stepping off a plane in aviators — now that you know this story, you’ll understand the look of sheer terror on my face).

That night, Obama summoned Axe and me to his hotel room. He wanted to talk about the latest draft, but first, we turned on the television for a sight we never thought we’d see: Hillary Clinton, on stage at the convention in Denver, delivering one of the best, most passionate cases for Barack Obama’s candidacy we’d ever heard.

It highlighted for Obama that his speech still didn’t have a central thesis — it didn’t make a clear argument that held all the different policies and proposals together:

“We keep talking about the American promise at this convention, but what is that promise? Isn’t it that each of us has the freedom to do our own thing, but the obligation to treat each other well? Isn’t it that government can’t solve all of our problems, but should solve the problems we can’t solve on our own? That it should ensure a basic level of opportunity for everyone?”

As he went on, I typed every word as fast as I could. At about midnight, his long, slightly meandering riff came to an end.

“OK, you got all that? Think you can turn this around by first thing tomorrow morning?”

He saw the look on my face.

“I’m sorry. Can I buy you a Red Bull from the machine?”

It was the first true all-nighter I ever pulled. But by the time we arrived in Denver the next morning, we had ourselves a speech — or, at the very least, a speech that Obama was ready to line edit. The rest of the speechwriting team joined us at the convention, and we all went back and forth on drafts until dinner. As we left to get some food, Obama said, “Favs, don’t come back after dinner. You’ve been up for two days straight now. Your mother would kill me. Go get some rest. We can take it from here, and we’ll wake you up if anything exciting happens.”

That’s the man I worked for.

I look back at Obama’s 2008 convention speech today, and there are certainly some things I would change. There’s still a little too much policy detail. There are a few too many hits on McCain. There are a few cringeworthy lines we threw in for applause (“Eight is enough!”)

Still, there’s one part toward the end that I’ll always remember — not from when he delivered it on stage that night, but when he practiced it earlier in the day.

We were in yet another makeshift rehearsal room, prompters and all. Obama began to deliver the speech aloud for the first time. As he approached his first applause line, there was a knock on the door. He opened it to find someone from hotel room service.

“Did anyone order a Caesar salad?”

There were a few seconds of complete silence as we looked around the room. Finally, Axelrod sheepishly raised his hand. “Axe, I’m terribly sorry to interrupt your lunch with my convention speech,” Obama quickly said, smiling, and we all started laughing.

He went through the rest of the speech just fine, but when he got to the end, he paused. I thought it might be another knock at the door, or something wrong with the prompter. But when I looked up at him, I saw tears in his eyes. “Give me a couple of minutes, guys — I’m sorry. I guess it finally hit me.”

He disappeared into the bathroom for a bit, and when he came back, he finished the speech without a problem. A few hours later, he accepted the Democratic nomination for president before a record-setting crowd of 84,000 people on a beautiful night in Denver. And this time, when he delivered those final lines, his eyes were clear, steady, and filled with pride:

“… It is that promise that, 45 years ago today, brought Americans from every corner of this land to stand together on a Mall in Washington, before Lincoln’s Memorial, and hear a young preacher from Georgia speak of his dream. The men and women who gathered there could’ve heard many things. They could’ve heard words of anger and discord. They could’ve been told to succumb to the fear and frustrations of so many dreams deferred. But what the people heard instead — people of every creed and color, from every walk of life — is that, in America, our destiny is inextricably linked, that together our dreams can be one.

‘We cannot walk alone,’ the preacher cried.

‘And as we walk, we must make the pledge that we shall always march ahead. We cannot turn back.’”