Why I’m proud(-ish) of something I made

Last year I launched a podcast. It was called Special People. The log line was:

Special People: the podcast about the most important people in our lives.

(With jokes.)

I wanted to interview people about the most important people in their lives. The ‘special people’ my guests talked about could be… absolutely anyone. Good people. Bad people. People they needed to meet.

I did 36 episodes of it in the space of 12 months. I am proud-ish of it. I’ll explain the “proud” part, then the “-ish” part.

PROUD

1. I’m proud that I actually put it up. The technical demands of bringing it into the world were difficult. I’m not a tech natural. Buying the right equipment was a financial sacrifice. Even the basic act of recording it (in what I will generously call “reasonable” audio quality) was a challenge. Creating an evergreen place for it to live online — using Libsyn to host and Squarespace to showcase the content — was not the easiest choice. But I powered through and made it happen. We should high-five anyone in the world who has actually made a fucking thing happen. Making a thing is always so much harder than we can possibly fathom from the outside.
2. I became a decent interviewer. I learned when to shut up and let someone talk. I learned how to keep an hour of conversation loose enough to be spontaneous, but structured enough to help a listener stay connected. I learned how not to go for an easy joke. I learned how to stay present in a moment, and ask the question a listener, yelling at me through their headphones, would ask. I learned how not to miss an opportunity. I learned how to respect a guest. I also learned how not to respect a guest. Too much respect leads to boring talk. I got better at that balance. I’m proud of those new skills.
3. I talked with real award winners. My conversation with ex-Daily Show writer and 8-time Emmy winner J.R. Havlan was a doozie. We walked home together that night, too. And during the course of the walk, he answered every single juicy question I *should* have asked when the mics were on, but didn’t, like an idiot. I also loved my talk with Pulitzer Prize-winning New York Times reporter Serge Kovaleski. And I learned a few things about making news at the highest possible level. (While we were talking, at that very moment, Donald Trump was publicly insulting Serge — by name — to every news outlet that would listen to him. So, all of them.
4. I actually connected with people I love. I got to hear how future comedy legend Jo Firestone was almost destroyed by an ex-con in St. Louis. And how Matt Ruby uses Tom Petty as a personal lodestar. I cemented what I hope will be a lifetime of friendship with people like Kyle Ayers, Jeff Simmermon, Casey James Salengo, Doug Smith, Ahri Findling, Ryan Beck, Selena Coppock, , Tovah Silvermann, Jenn Welch, and Joe Zimmerman.

Amazing people went deep.

D. Perafan talked about being committed to Bushwick psych ward on Christmas Eve.

An anonymous friend talked about the end of his marriage, with no detail spared.

Monroe Martin explained how he survived a childhood spent in 15 different foster homes over 14 years (sic).

Wonderful people surprised me.

Diego Martin taught me a different way to approach regret, and how to get punched in the face.

Bob Hansen told me what it takes to be a professional wrestler.

Brooke Arnold and Dave Ebert took me inside the heart-breaking derangement of Christian cults.

Oliver Chin walked me through the process of female to male transition.

And I learned from the best interviewer the comedy world has ever known: Mike Sacks.

I’m proud of all of that.

Here comes the “-ish”.

“-ISH”

1. I called the show “Special People”. So it sounded like a show by and for the mentally handicapped. The first time someone pointed it out, it was funny. By the 17th time? I wanted to kill myself. Every time I saw the title, a stabbing needle of shame pushed deeper into my soul-nuts.
2. The audio quality. Oh, the audio quality. I had no dedicated show intro music, I had no “stings”, I had no reliable way (or skill-set) to level my output post-recording, and I had nothing better than Garageband to record the podcast on. That’s the 2009 edition of Garageband… the Garageband that is such a poor platform for podcasting, Apple actually DELETED podcast functionality from subsequent versions. I’m amazed the show is listenable. Also, on at least two occasions, I DID NOT PLUG MY MICS IN. That’s right. I set up all my fancy equipment, but neglected to plug the jack from the mixer into my laptop. Both my and my guests’ audio was just taken from the MacBook in-built mic. I have a master’s degree.
3. I didn’t prepare enough. Every interview felt like a Hail Mary Pass. Getting a guest booked and the equipment set up and all the technical aspects squared away felt like such a major achievement every week, my self-sabotaging brain left no time to actually prepare for the interview, and think about the CONTENT of the damn thing. Go back and listen to the Mike Sacks episode. He has built a career on scrupulous preparation, and I pledge from now on I will adopt his high standards or not bother interviewing at all.
4. The format was a problem. I was asking a lot of my guests, basically hoping that they would arrive with a perfectly formed anecdote about a person who changed their life forever. Most of them did, thank God. But not everyone is lucky (or unlucky) enough to have such specific heroes/villains in their lives, or willing to discuss them in public, or able to put the importance of those relationships into words. These things go beyond words sometimes. This, I have decided, was the fatal flaw of the show.
5. I say “fatal”, because I have decided to end the show. It was a great “sketch” for something else. A study. A first pancake, if you will. (You always throw away the first pancake.)

That’s the bad news. Here’s the good news. I’m going to launch another show at the end of summer 2016. And I’m going to pin this post to my forehead until then, to remind me of what I achieved, what I learned, and what mistakes I should not repeat. If you would like to know when that podcast is launched, give me your email and I will let you know.

Special People will never go away. I’ll host it in perpetuity. It will live here until I’m dead, I guess. Feel free to enjoy it forever. I’m extremely proud-ish of it.

The most popular thing I've ever written

A week ago, Gwyneth Paltrow and Chris Martin announced they were splitting up. The UK's Daily Telegraph (their biggest broadsheet newspaper) emailed me out of the blue. I'd written for them in the past, but not for a few months. They asked if I could turn something around in an hour: they already had an American woman's perspective on marrying a British man? Could I give them the opposite viewpoint? I bashed it out, happy with most of the jokes. I sent it, and promptly forgot about it. They ran it. And it blew up. It hit their front page. Last time I checked, it had been shared over 19,000 times on Facebook. It didn't change the world or anything, but it put me on the map with a few important people. That's a big win for me.

There's a weird lesson in here. Opportunity visits in strange ways, and at odd times. You may not recognize it when it arrives. But if you are always working hard, always honing your craft (pitching, thinking, meeting, performing, challenging, writing, and RE-writing), you will get your chance to shine in front of a large audience. If you are in a creative profession, it can seem like most of the time, you're just WASTING your time: writing stuff no one reads, telling jokes no one hears. You are not. You are constantly improving. And when opportunity knocks, it will be the anonymous failures that prepared you to succeed.