A Clear Red Flag That Your Podcast Is Doomed to Fail

By Jeremy Enns

By Jeremy Enns

By Jeremy Enns

I’ve had 1:1 conversations with literally hundreds of podcasters looking to grow their shows.

And there’s one sentence that—when uttered—instantly tells me that their show will probably never be successful.

I’ve heard it spoken by everyone from solo creators to in-house marketing teams to seasoned entrepreneurs and celebrities who are getting into podcasting for the first time.

The phrase?

“I know I have a really good show…”

I’ve heard this line probably several hundred times and in most cases, I’ve listened through at least the first few minutes of an episode.

Out of those hundreds of episodes, I can think of just 3 specific shows that I thought were good enough to deserve many more listeners than they were currently getting.

It’s possible I’m a harsh critic.

But I’m not nearly as harsh a critic as a potential new listener who is (subconsciously) looking for reasons to disqualify the show as quickly as possible.

In most cases, the hosts that are most confident in the quality of their work seem to be those with the least idea of what they’re competing with.

  • They listen to few (if any) other podcasts of any kind, let alone those in their niche
  • They often aren’t even aware of the existence of other shows in their niche, let alone their specific formats and topic focuses
  • As a result, they tend to produce shows that are wholly undifferentiated from their competition

These hosts are stuck in Stage 1 of ​Tim Urban’s​ depiction of the Dunning-Kruger Effect where our incompetence is concealed by our ignorance.


Perched atop Child’s Hill and unaware of what else is out there, these creators possess a misplaced sense of confidence in their work.

One that will ultimately keep them stuck in place forever…

Or at least until they acknowledge how little they know, and how far their work needs to go to be successful.

Embracing this reality is uncomfortable, however.

The most successful creators I know are often perpetually dissatisfied with the quality of their work.

They consume a ton of media, have developed exceptional taste, and are tormented ceaselessly by their inability to bridge the gap between their current level of work, and the level they inspire to create at.

That doesn’t keep them from trying, however.

And it’s this combination of perpetual dissatisfaction and compulsive effort to improve that allows them to recognize—and then create—shows that are truly good.

This process doesn’t happen overnight, however.

Ira Glass, one of podcasting’s few, homegrown patron saints knows this.

“The most important thing you can do is do a lot of work. Put yourself on a deadline so that every week you will finish one story. It is only by going through a volume of work that you will close that gap, and your work will be as good as your ambitions.”

Unfortunately, while his advice has been widely adopted (and quoted) by creators in other mediums—specifically writers and YouTubers—it often seems to go overlooked by podcasters.

The necessary volume of work to close the gap is not 10 episodes.

It’s not even 100.

In fact, for the creators who are destined to succeed, that gap will likely never be closed.

The pursuit of it will span mediums and genres and formats and many years, most of which will be spent in absolute and utter obscurity.

But this is the way.

Only through this volume of work will we ever hope to discern what “good” work actually is.

And it’s then, and only then, that we can begin to create it ourselves with any level of consistency.

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