The Upgrade: A Cautionary Tale of a Life Without Reservations (35 page)

I looked at the time. Still four hours until Sarah’s plane landed—plenty of time. I gently moved Amy’s arm off my shoulder and tried to figure out how to crawl over her and get to the shower. It was then that I realized something heavy was on the end of the bed, trapping my feet. I craned my neck up to see what the hell we’d left on the bed. Judging by my headache it was probably a keg of beer.

“What the fuck?” My whispered shout woke Amy up.

“What’s going on?” she asked.

“Look at the end of the bed,” I said. She craned her neck too.

“What the fuck?” she said.

There, curled up on the end of the bed, like a little fully clothed dormouse, was Milo from the
Telegraph
.

“What the hell is he doing on the end of the bed?” I asked.

I didn’t even remember Amy coming back to the hotel with me, let alone Milo. At least he was still dressed, I suppose, which was more than could be said for Amy and me.

Amy shrugged. Just another morning in London.

After half an hour in the shower, removing the smell of alcohol from my body, I headed out to meet Sarah.

I’d suggested a lunch to welcome her to London and her response was less than enthusiastic. But she could hardly fly all the way to London and not at least meet me for lunch.

“Hey!” I said, as I walked into her hotel lobby and found her already waiting, checking her email.

“Hi,” she said, forcing a smile, but clearly not sure that this was a good idea at all. I swear she was looking me up and down, trying to tell if I was drunk already.

“Don’t worry,” I said, “I’m not drunk yet.”

“Yet,” she said. Lunch itself, though, was far better than I’d expected.

After a few more minutes of awkwardness, we both realized how much we’d missed our bitching sessions about the publishing industry, journalism, Silicon Valley and our mutual friends.

Sipping a glass of water, I told her about Butlins—minus most of the drinking—and she asked how my book was going. I told her the truth—that it was going really, really badly, and she sympathized, raising me the fact that she was still slaving away on the chapter plan for her next book, an investigation into global entrepreneurship in emerging markets.

We talked for an hour without either of us really taking a breath; it was just like old times—two best friends catching up.

“This is great,” I said. She nodded.

“It really is. I have to say, I was really not looking forward to seeing you. I just didn’t want to have to
deal
with you, you know?”

But I didn’t know. Or at least I didn’t think I knew. She must have seen the hurt in my eyes and the confused look written across my whole face.

“You really don’t see it, do you?”

“I know I’ve been drinking a lot,” I said, starting to apologize. First Robert, now Sarah. I knew where this was going.

“It’s got nothing to do with the drinking,” she said. “Or at least, that’s just a symptom. I drink, everybody drinks. Yes, I’d prefer it if you didn’t act like a drunken asshole towards me, but that’s not what my problem with you is.”

“Then what is it?”

“It’s the fact that you’ve stopped caring about what you do.”

For the next hour, Sarah explained.

“When you said you were moving to San Francisco, I was really happy for you. I was going to introduce you to people and help you make connections there. But what happened? You got off the plane and you immediately decided you wanted to go to every party with a free bar and make this big splash as the new drunk British guy in town. You could have decided to arrange meetings and focus on the one big advantage you had—being one of the few people who writes about technology for a British newspaper but who actually lives in Silicon Valley. You could have got some real stories about them and then you could have written it in your slightly drunken Brit style that everyone loves reading; that I loved reading; and you’d have had the best of both worlds—the fan base who loves the fact that you’re a loser, and the people in Silicon Valley who would be interested in reading some proper analysis on the industry written by an outsider.”

“Loved reading?” I interrupted, caught up on the past tense.

“Yes, loved reading—past tense—once you decided to focus on the drinking, and to spend your whole life either drunk or hung-over, it
became really obvious from your writing. Look back at the early columns you wrote and compare them with the stuff now. You barely write about technology any more; it’s just a string of stories starting with “I woke up …” They’re funny for the first few times, but now they’re the rule not the exception. Also, you make no effort to hide your contempt for the people and things you write about—like your ignorance is a badge of honor. You write about drinking with Brits, or Americans who want to be around Brits, and about the hangers-on who go to every party there’s a free bar. And you do that like it’s where you want to be: that you want to be a drunken hanger-on too, and that anyone who actually takes the time to get to know serious people in the Valley or start serious companies or—I don’t know—write serious journalism, is somehow not worth getting to know. I lost count of how many times I had to tell people that you weren’t really like that, that you were a really nice guy and that when you were sober you wrote really well. I told them about your book, that you were just going through some kind of phase. And then …”

“And then what?”

“And then it stopped being true. The drinking took over, and the ego, and the don’t-give-a-shit persona you adopted in your writing stopped being a persona. It just became you.”

I didn’t have any response. Sarah was saying the same thing as Robert had said a few days earlier about my drinking, but to her the drinking was just a part of it. I’d become a hideous caricature of myself—a belligerent, egotistical drunk who forgot that it was supposed to be an act.

The evidence was pretty damning: I was less than six months away from submitting a book that I hadn’t even started to write and I was basically just phoning in my
Guardian
columns, assuming that as long as I packed them with enough drunken stories, they wouldn’t realize that I had stopped trying.

Looking back, it was an absolute miracle they hadn’t fired me.

The next day the
Guardian
fired me.

And that was that. Economics, pure and simple. With times being so hard for newspapers—ironically because the web is killing their advertising-based business model—the
Guardian
simply couldn’t justify continuing to pay me to write a weekly column about getting drunk.

As Charles said in his email, they were having to give lots of freelancers the boot, not just me, but, looking at the ones they kept, it was easy to see the trend. The writers left behind were the ones who added actual value: hard news, or proper industry analysis. The stuff that brings in serious readers.

For all my ego, that’s really what mattered.

“Are you OK?” For everything she’d said at lunch the previous day, Sarah seemed genuinely upset when I told her the news.

“I know it meant a lot to you,” she said. “Still, at least you can concentrate on the book now.”

That was true—and yet losing the column symbolized a lot more than a few hours a week saved; it meant I no longer had an excuse for living the way I was. The excuse that someone paid me to act like an ass had been my only real justification, to Robert, to Sarah, to all my other friends and to everyone else I met.

I could go back to just writing the blog, but it would be obvious to everyone that it was a step backwards—that people had fallen out
of love with my shtick. And then there was an even bigger problem: losing a regular paycheck was a pretty dramatic change in circumstances—I had no idea how it would affect my eligibility to live in the US.

I had less than a week until I was due to fly back to San Francisco.

“So, what are you going to do?” asked Sarah “Have you had any other offers?”

A few hours earlier, I’d updated Twitter with the news of my firing—more out of frustration than anything else, but also partly in the hope that someone might offer me another job.

“Actually, yes,” I said, “the
Telegraph
want me to blog for them.”

“Well, that’s good, right?” And it was, except for the fact that to most of my liberal friends moving to the
Telegraph
was like going from the ACLU to the KKK. Accepting their offer would be the very definition of whoring. More importantly, though, the blogs editor had made it clear that I would be bound by the paper’s strict “no swearing” rule.

“Maybe,” I said, “but it’s certainly no replacement for the
Guardian
.”

Sarah sat silently for a moment, clearly weighing something up in her head.

“Have you heard from Mike?”

M
ichael Arrington began his career as a corporate lawyer. Then, after years of advising Silicon Valley entrepreneurs on their businesses, he decided to launch a blog about the people and deals behind the second dot-com wave. So-called “Web 2.0.”

As Web 2.0 had grown, so had his site and his personal influence. By 2008 Arrington was listed by
Time
magazine as one of the one hundred most influential people in the world. The name of his site was TechCrunch, regarded by almost everyone—including me—as the most influential technology news site in the world, with millions of weekly readers including everyone who is anyone in Silicon Valley. And since Sarah had begun writing for TechCrunch, Arrington had gone from being her friend to her boss.

As it happens, I had heard from Mike. We’d met a few times at events in San Francisco and we’d got on reasonably well. Despite the fact that I’d taken occasional jabs at him in my column, he claimed to read it every week—mainly, I assumed, to reassure himself that TechCrunch had nothing to fear from the
Guardian
.

A few hours after I’d broadcast news of my firing, he emailed me with simply the words “
you’re hired
.” I’d replied back: “
make me an offer
” but hadn’t got a reply. I assumed he was joking. There were, after all, a number of reasons why me writing for TechCrunch would be ridiculous. For one, I only wrote one column a week at the
Guardian
—TechCrunch, like most news sites, is published twenty-four hours a day, seven days a week. Its writers are well paid but they’re expected to write more than one article a day, let alone a week.

Also, I tend to write long; my column at the
Guardian
should have been 900 words, but it often ran to over twice that. TechCrunch was all about short, newsy posts, tuned to the ADHD attention span of the
average Silicon Valley entrepreneur or investor. And, finally, something told me the drunken, sweary ramblings of a clueless Brit whose behavior since he moved to Silicon Valley had alienated everyone remotely serious wouldn’t fit well on the pages of the web industry’s paper of record.

Mike’s email was a nice gesture—and also a slight victory lap on his part, I suspected—but we both knew it wouldn’t come to anything. I explained all this to Sarah.

“I could talk to him if you like.” I literally didn’t know what to say.

“I … You’d really do that?” I asked.

I’d considered trying to act cool—“I don’t need your charity” and all that crap—but, given our recent conversation, it didn’t seem like the time for acting.

“I mean, you told me a few days ago that you were embarrassed by my writing.”

“I am,” she said, “but this could be your chance to fix that. You’d have to stop with all the grandstanding crap and actually start doing proper work. Keep the voice, lose the attitude, you know? Can you even remember how to start a paragraph without the words ‘I woke up …’?”

“I think so,”

I said, feeling thoroughly ashamed of myself, but also genuinely amazed at what I was hearing.

“Do you really think Mike would hire me?”

“Let me speak to him,” she said.

My flight back to San Francisco was due to leave in three days.

While I waited to hear back from Sarah, I had time to think and to make some serious decisions. The first decision, unsurprisingly, was to stop drinking.

Not to cut down, not to stop writing about drinking but still have the occasional beer with friends, but to actually stop drinking—for a few months at least. Until I’d got myself back on track, and actually started to make some progress on the hotel book.