In the fifteen years that I’ve been a podcaster, I’ve used many different kinds of formats. Daily shows, weekly, long-form interviews, unscripted improv, monthly magazine-style. None of them have stuck with me as something I’d like to do long-term.

I’ve noticed the surge in seasonal podcasting due to the popularity of shows like Serial and the rise of True Crime podcasts. So I decided to experiment with seasonal podcasting and dedicate each season to ideas I’ve had swimming around in my head for thirty years. Once I committed to this idea, I found it remarkably liberating, so much so that I could come up with an idea and produce twelve episodes of a season in a matter of weeks. To my delight, this season has been the most popular in terms of downloads, unique listeners, and fan engagement that I’ve had in some time. It’s led me to believe this is where I should have been all along, and I will continue making seasons of my show from this point forward.

With that in mind, I’ve got some observations about why this switch to seasonal podcasting became a natural fit for me.

They’re easier to outline

The first decision I made was the number of episodes I wanted to produce in the season. At first, I thought ten was a suitable number, but after some thought, I upped it to twelve because I would let the next nine episodes drop weekly after an initial drop of three. With that decision, I gave a topic to each episode, wrote a draft, and then edited it down. Because I took the time to do this first, I wrote the scripts for all twelve episodes in about ten days. It was a much better process for me than the grind of prep, outlining, writing, and producing every three to four days.

There’s a beginning, a middle, and an end

A season of a podcast is the same as the season of a TV show. You’re telling a long story that arcs over weeks. In this season of my podcast, I spent the first three weeks establishing the character called ‘This Pirate.’ Then over the following weeks, I let him reveal more and more of himself until we get to the last episode, which is a callback to the first episode and a nice ending to the season. The first-person narrative of ‘This Pirate’ made the writing very easy for me. Still, as I move into the next season of my podcast and a third-person narrative, it will be vital to tell a complete story with a beginning, a middle, and an end.

You can explore a variety of ideas

The following season of my podcast will continue the This Pirate line, but I have other ideas for future seasons. One of these ideas has been in my head since 1989, the rest since 1999. Of course, they’re fictional and will require more resources than just talking into a mic. Nevertheless, this switch to seasonal podcasting has lit that fire underneath me to start writing these stories and put them out in the real world in a way I never could do before. Perhaps it’s better to say that I’ve never felt as empowered to put these stories out in the world before now. Regardless, I’ve never been as positive that I can produce these figments of my imagination as I do now.

I find them less taxing than a weekly podcast

A daily or weekly podcast is a Sisyphean effort of prep, outline, write, produce, distribute, and repeat. It’s almost too much for one person to do, and I respect anyone who can. I can’t. I’ve repeatedly tried, and with kids and a job and obligations, it’s just too much for this guy. While the effort it takes to create a whole podcast season in one shot may seem just as much a struggle, it’s just for a short time. Once done, I can move on to the next thing on my list, like Promotion, community building, and scheduling some downtime to prepare for the next season. The weekly grind creates anxiety for me, and when I have that anxiety, I can’t perform consistently. I would rather be anxiety-free and consistent than be bouncing off walls and podcasting on a hit-or-miss basis.

They can be pre-produced and pre-scheduled

After I wrote the 12-episode season, it took me another four days to produce and distribute them. So from the initial idea to distribution, I created 12 episodes in about two weeks. Pre-scheduling these episodes to drop means I have a podcast season that runs weekly until July 30th. I plan to add one more episode out of the Pirate character, but I plan to record that closer to the end of the season to include more behind-the-scenes material. So this podcast will end on August 6th, and by then, I hope to have most of the next season produced, tentatively scheduled to start around Labor Day. The mental bandwidth it gives me and the pressure it takes off me is priceless.

Consistency is built-in

You must maintain consistency in creativity to keep an audience engaged. After a while, if the audience can’t rely on you to deliver when you say you’re going to deliver, that audience will move on to someone who can. With this method, your consistency is built-in. You’ve guaranteed that there’s a new podcast dropping next week for the next couple of months while you’re working on the next thing. Because it’s a season, you can bake the expectation of a hiatus until the next season into the last episode of this season. As long as you tell your listeners what’s happening, they’ll be there waiting when you get back.

Promotion is easier

Let me get this out: Promotion has never been my strong suit. I know they won’t just come if you build it, but telling people that I’ve built, it has always made me feel — and this is a technical term — icky. I despise high-pressure salespeople, and I don’t particularly appreciate feeling like one. However, with the reclaimed time I have using the seasonal method, I can create graphics and stories for my social media accounts and pre-schedule those posts using Buffer. A bonus to this method is using my social media accounts to be me, which lets me feel better about the scheduled posts hawking my stuff. I tend to schedule those posts about four hours apart, so those posts are bookends on a sandwich, with me being a human in the middle.

The M Word

Finally, we get to the elephant in the room. Of course, the obvious upside to seasonal podcasting is the possibility of monetization. I uploaded all the podcasts in the season to Patreon. I offered early access to all the shows for five dollars a month, with the ability to access a subscriber-only podcast and a monthly get-together on Twitch. With this new way of doing things, I admit that the Patreon approach is not yet working. However, I believe it will take hold because the podcast is still growing. Looking at the data for my show, I reached the total downloads for May on June 14th. On that trajectory, I should double the number of downloads, and if that trajectory holds, I should be able to continue outperforming the previous month. On the subject of unique listeners, I continue to attract new listeners every day, and repeat listeners return for the next episodes. I think it’s only a matter of time before the subscriber model starts working.

Conclusion

Of course, your mileage may vary. For me, this switch to seasonal podcasting has been the best decision I’ve made for my creative work since I decided to start creating audio for the internet back in 1999. So if you have a day job, family, kids, obligations, or you want to start a podcast but don’t think the weekly grind is for you, I would strongly recommend seasonal podcasting. I see no better way for me; I hope it works for you.

When I first started podcasting in 2006, I didn’t possess the technology to do interviews, so I left that out of my show for a long time. One of the first interviews I did in 2008 was with a gentleman named George Tabb, a NY punk icon and early activist for those who suffered from 9/11-related sickness. While it was a bit stilted and awkward, it gave me a definite idea of the kinds of interviews I wanted to do in the future.

I think the essence of a good interview is that it isn’t an interview at all. It’s a conversation. That’s why Larry King and Howard Stern are so good at their job. They engaged in a conversation with their guests, and in doing so, they could draw more out of their guests than intended. Someone who has appeared on Stern has said they told him things they would never have spoken to anyone else. I think that’s a high compliment, and it’s certainly something I try to emulate. Last year, I did a limited series of interviews on my podcast related to how people became creatives and how they stayed creative during the pandemic. I’m biased, but I think it’s some of my best work because I think I managed to get into a personal zone with people and gain their trust during the process.

I am by no means an expert, but I do know what works for me. So I’d like to share with you five things I would do when interviewing guests.

Do your homework

If your guest has written or appeared in anything recently, you need to know about it. Read and consume anything relevant to your conversation, and maybe go beyond that. I like to ask relevant questions, but I also look for human moments in a person’s bio, social media, blog posts, and videos. If it’s funny, all the better.

Now, you may want to tell the guest you found this moment and ask if it’s ok to bring it up. Don’t go for embarrassing the guest. It’s crass, and that guest has friends who will hear about it and never appear on your show. In my experience, the human moments we all share can be a real icebreaker or pressure release during an interview. If you can get the guest to share that laugh with you, you’ve got a good conversation going.

Listen. Really.

It’s easy to get sidetracked doing other things while the guest is talking. Riding a volume level, responding to chat if this is a live stream, posting quotes on social media, and other things. I’m asking you to stop that. Your focus should be entirely on the guest and what they are saying. I have heard my share of podcasts where The host prepared the questions well in advance, and the guest said something nullified a question, only to have that question pop up later in the show. That’s an unforced error, and you’ll pay for it. The other problem with not focusing on the guest is that it becomes very awkward. Sure, you can fix long pauses between questions in Post, but the guest may have a bad feeling about it, and it will reflect in their attitude, and the quality of their performance as the interview goes on. If you realized the person you were talking to wasn’t paying attention, how long would you stick around and participate? Exactly.

Be prepared to go off the list

I want to be clear about this point. I am not saying that you shouldn’t have a list of questions or a game plan for this interview. I am saying that if you’re actively listening to the guest, they may say something that opens up a whole new line of questions you hadn’t thought about and might be worth exploring. Conversations are not linear; you can drop one thread, pull on another one for a minute, then come back to the first one. That is what makes for an organic, authentic experience for the guest and the listener. If the guest feels you are in this experience with them, chances are they’ll trust you more, and they’ll loosen up and give you the interview you want

Stay in tune with the guest

You should be getting a good read on your guest as the interview proceeds, and you should be getting an idea of places you should and shouldn’t go. If you inadvertently head down a path the guest doesn’t want to go, and they might clam up a bit, don’t push. In some cases, the guest might say something they didn’t realize would take them down that path and then give you some indication that they’d rather not. If you hit a boundary, respect it.

Know when to end it

Ideally, you’re looking for an interview to take up a substantial part of your regular podcast, but like any party, you should be looking for hints that the party is ending. The guest might start giving you shorter answers or other context clues when they start feeling like they’ve said everything they need to say. When I get to that point, I have two questions I ask to signal the guest I’m starting to wrap up. I’ll ask what they’re working on now (or next) and how people can connect with them on social media. Then I’ll thank them and wrap it up. Know when that time is coming, and don’t stretch it out. An interview that goes too long becomes awkward later, and the listeners will pick up on it.

Interviews don’t have to sound like interviews; they can be all call and response and no substance. To get to something real, don’t treat it like an interview. Treat it like you’re just talking to a new friend you want to get to know. The result is a better product for you, a better experience for the guest, and trust as an interviewer grows in your field.

I want to start this by suggesting each of us ask ourselves a question: Am I OK?

I know that might sound simple, and you might think that’s ridiculous, but I’m dead serious. I want you to ask yourself if you’re OK, and I want you to be honest with yourself about the answer.

The reason I’m talking about this is pretty straightforward, I have had to ask myself this same question, and my answer is “I’m not sure.” I’m not OK, but I’m not in dire straits or anything. I can only describe myself as being in some weird limbo state that allows some things to pass, and other things stick and drag me down a little bit for a little while. I don’t know if anyone can relate to this, but maybe you can. It wouldn’t be the first time I’ve lost my audience by talking gibberish, and it certainly won’t be the last.

Basically, I’ve spent most of my time in the company of my family or outdoors, far away from everyone else. The main human contact I’ve had is with people that share my last name. I have seen other people three times in the five months we’ve been in this state. The only time I can tell you I am in the company of other people for any length of time is on Sunday Mornings when we do the groceries. I have not done any delivery side jobs since the shutdown because I think it’s dangerous. I lost a job I absolutely loved at the end of May. I’ve been looking ever since. I’ve been doing freelance work, but it doesn’t replace my income. I wish it did.

Some of you will tell me that I’m acting like, as one friend has put it, a covidiot. There are a few people in my life that believe that this thing has been blown out of proportion, that it’s not as bad as the news has made it out to be, that it’s a big hoax, and that I’m a sheep. If that’s what you believe, you’re more than welcome to believe that. You do you. What I’m not going to do at any point is argue with people about this because that’s time out of my life that I’m never getting back, and what I have seen out of the arguments I’ve read or been a witness to is that the anti-maskers are all about demanding respect for their rights, but not willing to respect the rights of others. I’m not into recognizing your right to put me in a possibly bad situation, but I’m not going to change your mind, and you’re not changing mine, so let’s just leave it.

I realize that I will probably have to break my promise to myself that I will never take another Customer Service / Tech Support phone call, and I hate it because the second I take that job, I feel like I’ve given up. I have done many things, but giving up is not one of them. Still, coming to that conclusion has not done wonders for my disposition. It’s depressing, to be honest. I had a great job, and I want to keep doing it. I just have to figure out how, and I don’t have much of a plan as I have a bunch of ideas that barely string together to form a coherent thought.

As near as I can figure, what I need to do is post content every day and promote the heck out of it. I need to reach out to people and ask if they need something I can provide, like podcast editing or Voice work, for example. I think I’m going to create a storefront to sell my photos somewhere. I’m going to write like the dickens and get it submitted places. I would like to start making videos again, and that one seems to be the hardest button to button. I suffer from what I’ll call “Neistat Syndrome.” I just don’t think my life is that damn interesting compared to people like Casey Neistat or Peter McKinnon, and while I know I’m comparing myself to two of the tippety-top YouTubers, It’s still a thing I’m dealing with. I need to think about the format.

In the end, I think I have what Michelle Obama says is a ‘low key’ depression, maybe? I don’t feel bad, I just feel resigned to certain things and disappointed. I’m fifty years old, and that’s a factor. I indeed have more time than my parents had; there is a limited amount of time on the game clock. So I’ll do what I always do. Work, and try to pull off the seemingly impossible.