HERE’S THE THING: Lessons from Los Angeles about comedy, writing, and why lessons are bullshit

Welcome to HERE’S THE THING, where I talk about comedy-related things in a very HERE’S THE THING-type way.

I just returned from six days in Los Angeles, which was a trip I took for two reasons: 1) To visit my wonderful friend Dave Carp, who recently moved out there, and 2) to get some answers. Two years ago, I quit my job at The A.V. Club’s Chicago section so I could pursue freelancing full-time as a writer. Specifically, it was time to attack national-interest pop culture stories, and that required a move to New York—arguably the center of journalism in the United States. I felt unbelievably self-assured in my decision, and this is coming from a guy who doubts himself about the color of the iPhone case he buys or the toppings on a pizza he just ordered.

It was a crazy thing to do, and I felt great about it. But what I gained in mobility and day-to-day work customization (today I played video games and wrote about Bored To Death), I lost in automatic career direction. Without the indicators of advancement present working for a media outlet—or really any job—I was feeling lost. What was I working towards? I’d felt like I’d become a better writer, but did anyone care, specifically my editors? There’s that self-doubt again.

So I was in LA looking for answers. And even though I feel like I got more of them than I had anticipated, I realized just how little I know, how much work I have ahead of me, and how excited I am to attack the nebulous unknown.

Before I arrived, I stacked my days with meetings—lunch, coffee, or otherwise—that I hoped would illuminate some of what I’m hoping to accomplish. See, I’ve been a journalist for many years, and have enjoyed the occasional comedy piece I write for reading/performing series like The Paper Machete, or stories I’ve told at The Moth or my very own The Jukebox. I wanted to know what sorts of things writers do, and I mean “writers” in the most general sense. I met with comedians and industry folk, my editors at Variety whom I’d corresponded with via email but never met in person, the people I know at Earwolf, and writers on TV shows I really like. I recorded a few podcasts, ate really good Mexican food unlike seemingly all of New York, and spent a lot of time bouncing crazy ideas back-and-forth off Dave. It was a ridiculously productive three-or-so days.

And I’m only talking about half of my trip here. Because by the time Friday rolled around (I’d arrived Tuesday), I had what I thought was a pretty good handle on what I needed to be doing:

• Take stock in what I have by putting together a writing packet that demonstrates all of my abilities, not just tailored to a particular show or opportunity. Make it customizable.
• Be self-assured in what I’m doing. If I want to be the preeminent comedy journalist or whatever, tell people that, and stick to that as much as possible.
• Network more. Keep talking to people who do cool things, and let them know about the cool things I do. You never know what you’ll find in the fringes, what sorts of jobs exist you didn’t think existed.

Productive, for sure.

But then I got a text from Garry Shandling Friday afternoon that began the chain of events to undo all that work—in the best possible way.

Okay, I should back up. I have this strange relationship with Garry Shandling—which sounds a lot creepier than it is. I interviewed him ever-so-briefly for Variety last summer, since he was going to receive the Lifetime Achievement Award at the Just For Laughs festival in Montreal. What was supposed to be a brief 15-minute chat turned into something more like an hour, and I’m not quite sure why. Perhaps Garry doesn’t get to talk to many journalists these days, because he doesn’t need promotion or his “people” only let few people through. Perhaps he sensed my genuine curiosity in what he had to say, and admired my lack of star-struck-edness. (I certainly think Garry Shandling is a genius; I’m just not easily fazed by celebrity, which I suppose makes me better at my job.) Whatever the reason, it was a great chat, and I let him know that I would be in Montreal when he receives his award. He gave me his number and told me to call him when I got into town. Maybe he thought that was the end of it, but what he didn’t know is that I will never not take somebody like Garry Shandling up on that.

So I called, it went right to voicemail, his mailbox was full, and I sort of figured, “Ah well.” Then I saw him at the actual ceremony, introduced myself, and the first thing he said to me was, “You never called me.” I assured him that, indeed, I had called, he told me to text him next time, and within 24 hours I was headed to his hotel for a private meeting. Again, not as creepy as it sounds.

The meeting regrettably lasted only a few minutes, because he had forgotten the exact time of his flight and had to get going. But he told me that if I ever found myself in LA, he’d be happy to meet with me. Maybe he thought that was the end of it, but what he didn’t know is that I will never not take somebody like Garry Shandling up on that.

So I’d texted throughout my trip, we had vague plans to meet up Friday afternoon, and I hadn’t heard back. I headed to the set of How I Met Your Mother, where a friend works, and watched the cast of one of my favorite shows goof around on-camera. Then Garry texted, and I had to leave. Dave came too.

We met at the secret boxing gym he belongs to, and we decided to drive out to the beach and go for a walk. Because he only had his Porsche with him, and it only seats two, we had to take Dave’s car, so off we went in this beat-up green Toyota.

There’s a lot I could tell you about my walk along the beach with Garry Shandling (and Dave). But the first thing he said to me as we headed to the car was, “Is this off the record?”, which of course it was, and I want to respect that. It wasn’t really that personal of a talk or anything, but you never know, so in the interest of playing it safe, I’ll just say that it was pretty surreal. He’s really in-tune with people, the way they’re behaving, and what’s causing their actions. VERY. He told me things about myself that I didn’t want to admit were true, but very much were.

One of those things was probably really obvious to everyone except for me: I don’t know what the hell I’m doing. BUT…that’s not a bad thing. The hungrier I am, he said, the more opportunities I’m going to take advantage of and the more I’m going to figure all this shit out. That’s just it, too—I’d been talking to all these people, telling them what interests me, and secretly hoping they would say something like, “Aha, you should be doing this!” Which, of course, they couldn’t. I had to remove myself from the pressure others put on me—the pressures of a career, the pressure to find answers and be working towards something—and simply keep doing what I’m doing. Take a deep breath, I’m fine. If it sounds very Zen, well, then you can be sure it came from Garry Shandling.

I came to LA seeking answers, and I learned that the pursuit of answers is fruitless. So here I am, writing this blog post, part of my new and invigorated goal to trust my instincts and meander. I’ve worked all day sitting at my computer and writing, and the last thing I want to be doing is sitting in front of my computer and writing. But, at the same time, it’s the only thing I want to do.