On getting good by not letting yourself be bad

You write, edit, and publish Hot Pod, a newsletter about the podcasting industry. How did that come about?

I started it in November of 2014, right in the middle of the first season of Serial, which was exploding at the time. I was working another job in a newsroom and I wasn’t particularly happy with it. I felt like I wasn’t learning very much. And by that time, I had already been a huge consumer of podcasts. I’m originally from Malaysia, and came to the States for college in 2008. In Malaysia we didn’t have a tradition of narrative radio, so when I first encountered public radio during freshman year, it was a big revelation for me.

When Serial peaked the way that it did in the first season, I saw a bunch of writing, sort of mainstream coverage about podcasting, that I felt was in contrast to what I understood about the medium and the business behind the medium. So I started a small project through Tiny Letter, a free newsletter service, and I just started writing, basically blog posts or weekly thoughts on what I felt the podcast industry was going through. I used it as an opportunity to teach myself how to report, how to do analysis, and how to talk to people.

So I had this project that I kept doing every week, and I’ve just never stopped doing it ever since. That’s how it’s grown into what it is today.

Did you consider yourself a writer before you started Hot Pod?

No, and to be honest, I still don’t consider myself a writer at all. It’s just a form of expression that feels very true to me that I enjoy doing. Even though I hate going through the process, I love having done it. I’m a very anxious person, and I use writing to work stuff out a lot. It’s the thing I go to when it comes to managing my emotions, to be honest.

Why don’t you consider yourself a writer?

I don’t know, I just feel like it’s an identity that I don’t quite feel like I’ve earned, or I don’t quite identify with. I feel like there are such connotations around the notion of, “I’m a writer.” I don’t really know what I am. But, it’s what I’m doing at the moment. It might change over time, who knows?

At what point did you decide to solely focus on Hot Pod? Was that in the plan?

No, I think the reality is that none of this was ever planned. If you asked me when I graduated college in 2012 if I would expect myself to be a podcast guy, I would obviously have said, “No, I have no idea what you’re talking about.” I decided to go solo because I had loved doing Hot Pod as a side project for a number of years by that point.

I had the sort of usual experience of being a young person, trying to figure out how to build a professional life in a world that doesn’t quite feel like it’s built for me. And you kind of have to add that I’m a recent immigrant. I moved to this country in 2008, and I decided to stay, and I got married to my now wife, and I have all these feelings of like, you know, “I’m not American, I don’t quite belong here, and don’t quite fit here.” All these systems, all these ways of working and being a person in the world, it doesn’t quite make sense to me. So at some point, I just had enough bad work experiences that I decided to go solo. And to start my own company and see where it took me.

I assume that going out there on your own can come with a lot of pros and cons, one of the cons being you don’t have colleagues to read your work, or an editor. How do you edit your own work? It seems like it would be hard and solitary at times.

Oh my god, well, it’s incredibly lonely, right? I literally do everything. I write, I edit, I publish, but I also source for the stories I report, I fact check and do as much contextual research as I can. But on top of that, I also make sure that the website is running, I file my taxes. I do the legal stuff and I do the accounting stuff.

When it comes to the core experience of writing a piece, or having a column, I usually don’t have a ton of time between writing and editing. I’m always super hyper careful with having too strong of a take, when it comes to an angle. My big thing, personally, is to be as charitable and as generous as possible with my interpretations. But, if I need to take a punch, I have to be generous in that punch. It’s definitely made my anxiety worse, but to be perfectly honest, it can only work because I’m anxious all the time.

What do you mean by that?

I am so afraid, all the time, that I misunderstood somebody, or I got something wrong, or I misread something. I average maybe one or two typos a newsletter. I also average one or two things that could warrant a clarification or a correction. But I feel like my constant fear makes me a bit more clean as a writer, as a person who tries to put this stuff out on paper.

More careful, I guess?

Yeah, carefulness is one way of putting it. Anal is another way.

I imagine that time management is a huge part of successfully running your own creative business. How do you manage your time?

Oh man. It’s funny, because I feel like in many ways I’m the laziest and least disciplined person in the world. But that’s because I’m very, very harsh on myself. But I have a routine, and I never break from the routine. I try not to. I mean that physically, like when I say that I’m going to be in front of a computer and work on this thing, I will be in front of the computer and work on this thing. I might be procrastinating at many points in that process, but as long as I’m physically there, the opportunity for me to get back to work is always there, which is good. And I try to never break that bond.

Also, I think it helps that I work alone, because when I used to work in a newsroom and at companies, my favorite thing in the whole wide world was just walking to the guy over at the next table and just shooting the shit. I love gossip so much. That’s why I do this job. And so I think it’s good that I work alone, to be honest.

What is a writing or working habit that you feel like you always have to fight against? And how do you fight against it?

I have a lot of tics within my sentence structure. I keep a very conversational tone, but I also have a few crutches. I know my crutches very well. I use the phrase, “which is to say,” a lot. I use the same dumb lead structures all the time. And I try to let myself do that, to be honest—I try to lean into my tics.

I don’t see writing as an artistic act at all. I think it’s a little bit more like farming or building a house. You just have to lay down some structures. That is always the same. And you build, or improvise, around all those things. So I let my tics sit there, and I use them a lot. It’s kind of a weird push and pull.

I saw you tweeted recently that you “fucking hate writing.” I think a lot of writers can probably relate to that feeling, at some point in the process. When does that feeling usually creep up during your process, and how do you bring yourself out of those moments? Or do you let yourself be in those moments?

I tweet that like every other week nowadays. It’s coming out a lot more fast and furious.

This is probably not a healthy thing, but I really do not think what I have to say is important. I really, really don’t think that anything that I put on paper feels new, and I’m surprised that I get to do this every day. I’m surprised that people let me do this every day. That is a feeling I’ve never been able to shake, and I don’t think I ever will. So that is definitely part of why I feel like I hate writing, because I sit down, and I put words and sentences together, and on the aesthetic level, I feel like I’m nowhere near good. I don’t even think I’m a decent constructor of sentences. And when I look at something, I look at the first few sentences I put out every week on the draft, and I’m like: “Oh, this is garbage. This doesn’t flow right, this doesn’t feel good. I don’t even know what I’m saying. All this is garbage.”

I think it has to do with the fact that I’m a huge consumer of stuff. I compare the sentences that I put together with the things that I see, and I’m not able to let the stuff that I write kind of be considered on its own terms. I understand it can be somewhat unhealthy, but I also feel like the opposite is not great. Like, if I loved everything I ever wrote, I’ll just be that guy in that lit class in college who is just really insufferable. And I feel like that is how you get good: you don’t let yourself be bad.

I read that one of the reasons you started Hot Pod was because you needed to do something other than grocery shopping on the weekends to fill your downtime.

Oh my god.

You just landed a book deal. Is that kind of your new thing to fill your downtime?

No. Absolutely not.

That’s good.

So I’m trying my hand at fiction because it’s new to me, I haven’t written fiction before, and I just want to do something that isn’t my regular work. And honestly, even though I hate it sometimes, the only thing I know how to do is write. I also go to the movies by myself a lot. I watch a lot of basketball. I hang out with friends at bars a lot. That’s my new downtime thing.

I am curious to learn a little bit more about the book.

It’s an oral history of podcasting. The enterprise is to create a first pass at the history, so it’s a lot of interviews and restructuring conversations in interesting ways. There’s a balance to strike with structuring who I’m going to talk to with this book, who is going to represent the important parts, over the past 10 years, of this medium. I’m also new to oral history, so I’m learning how to get the stuff out of people in a way that looks good on a page. I’m supposed to file it next November, so I have months ahead of me with this thing. I think about it all the time, it scares me, but I like working at a 30,000-foot level. It actually feels very good to me.

What does that look like on a daily basis? How are you making a huge project feel manageable?

The process of these things is pretty much the same for me at any given point in time, which is to break the big parts into small little component parts.

My week looks like this: So the newsletter comes out Tuesday morning. I usually take Tuesday morning off. I take a nap, or I go for a walk, or I work out or whatever. And then Tuesday afternoon, I start thinking about stories for next Tuesday. Every Wednesday, Thursday, Friday, I work on the book in the morning. I work on Vulture stuff in the afternoons, and I do more reporting for the newsletter in the evenings. I listen to podcasts when I wake up in the morning, and all throughout the day, and sometimes at night. By eight o’clock, I try not to work anymore, because I want to be present for my wife and my life. I try not to work on Saturdays, just to give myself some breathing room. I come into my office on Sunday, and I work from two to six, and that’s usually me writing the column for Tuesday. Mondays, I edit the column, and when I feel like I’m done with it, I spend the remainder of the day either planning out my Vulture piece or doing more book work. That’s been the structure of my weeks so far. Sometimes I go into New York to do interviews, in which case, that entire day is lost time. But other than that, I try never to break from the routine, because if I do, nothing will ever get done.

You have achieved the dream of a lot of creative entrepreneurs. You’ve taken your hobby and turned it into your full-time job. What advice would you give to someone else who’s contemplating making their side project or their hobby their full-time focus?

So I’ll say two things. One was a piece of advice that was given to me. I wish I got it earlier, but a really good friend of mine, who’s a very successful creative person, told me this, and it really restructured the way I thought about things. I forget how he phrased it, but it was something like, “When you are more successful, you get more work and you hate yourself more.” That’s just gonna be what it is, especially if you are built the way that I am. But, the fact of the matter is, if the emotionality of the whole thing is to work to a point where it gets easier, it doesn’t. It gets harder and harder and harder. It’s more stuff, people know you more, you have a track record now, and that’s held up against you. That is what happens when this works out, and that’s a whole different skillset to sort of wrap your head around.

The other thing is to really know that this is what you want. I think when I shifted what was previously a hobby, something that I genuinely enjoyed doing, into something that is my professional life and the main thing that has come to define me in the eyes of a lot of other people, it completely changed the relationship between me and the thing. You cannot do it just for private pleasure anymore, and as a result, you have to be really fierce and focused as to why you love doing this thing.

The self doubt never goes away. The pain of it never goes away. If it does go away, I think something’s wrong with the process. It’s supposed to be hard, to a good extent. Which isn’t to say that it should be unhealthy, but I’m not the right person to ask for health advice at this point, I think.