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People always ask what I do with all my time, since this column clearly cannot take more than five hours, a number I’m greatly exaggerating for the sake of my editor. I explain to these curious people that, just like everyone even tangentially involved in the media, I spend the majority of my work hours as a guest on podcasts.

I have been on podcasts about things I know nothing about: cult films, entrepreneurship, baseball, motherhood, cocktails (two different ones) and, even more oddly, podcasting. It is totally feasible that there will soon be a podcast about podcasts about podcasts.

The reason so many people are creating books, podcasts, songs and videos isn’t that technology uncaged millions of potential artists by removing the barriers to entry. It’s that technology allowed people to consume tiny bits of media in every half-moment of potential boredom, thereby removing the barrier of being entertaining. All that content needs to accomplish is to be slightly more exciting than standing in line or paying attention to our children.

It’s gotten to the point where it’s embarrassing to tell people I don’t have a podcast. So after years of refusing offers to do one because the offers did not involve money, I got a deal from the podcasting company Midroll Media, which is responsible for such hit shows as Who Charted?, Yo, Is This Racist? and Denzel Washington Is the Greatest Actor of All Time Period. My friend Art Chung, who works at NPR, suggested I record just five episodes of self-improvement projects and call it What’s Wrong With Me? This sounded great to me, since I have exactly six things to improve about myself and one was not having a podcast.

I met the producer Midroll hired for me at a coffee shop near my house, and immediately knew I had made a horrible mistake. Shara Morris is 26, smart and eager to work hard, which was a huge problem since that would involve me working hard. I suggested we record episodes in which I wrote thank-you notes, learned about classical music and made a Republican friend. She insisted that I “dig deeper” for “truth” by working on my marriage, overcoming my lack of assertiveness, giving back to society and finding a more challenging career. Shara clearly thought this was her chance to win some podcast award from the National Podcast Association, which is an organization I have no doubt will exist by the time you finish reading this. By the end of our coffee, I agreed to do it her way, solely because I hadn’t yet tackled my lack of assertiveness.

So I found myself interviewing self-help guru Tim Ferriss, sex-advice columnist Dan Savage and philosopher Peter Singer; confronting my dad on his job as a grandfather; volunteering as a writing tutor and other things that took way more than five hours. My assertiveness-training therapist made me walk up to six strangers and compliment them, which sounds easy since I’m a reporter and, also, a human being. But it took me six weeks, and several hours of walking around coffee shops hunting for approachable-looking people. Five of my compliments involved hats, despite the fact that I don’t like hats. I just figured people with hats are looking for attention. Before I confronted my dad, I went to a Jewish deli and found an old Jewish man and asked him to pretend to be my father so I could practice. Then I had to confront my lovely wife Cassandra, who was upset that I was spending my time on a project that pays even less than print journalism.

And then, after I had a session with the brilliant therapist Phil Stutz, during which he told me I was dead inside, Shara started to cry because Stutz had casually mentioned she seemed to have some healthy anger in her. This led to an outpouring about how that anger was related to her feeling overwhelmed by the podcast workload. That required talking and hugging. About a podcast. This reminded me why I write, which already involves one too many people for my taste.

I told Shara that this was just one podcast in a bright career that will be full of many, many podcasts, and that one day she’d look back on our podcast as just a silly fling between a young girl and an old-media man. Eventually, she stopped crying and had me back in my living room talking into a microphone with a blanket over my head to improve sound quality. You confront your desperation to stay current when you’re under a quilt in the middle of the summer, next to a twenty-something podcast producer, talking to yourself in the dark about your marriage. Shara might not have been the only one to cry.

This appears in the September 07, 2015 issue of TIME.

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