Kevin Rapp: How to Be A Cynical Optimist (#31)

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Today I’m joined by hardware engineer and comedy writer Kevin Rapp. Kevin writes a weekly newsletter about nothing, aptly titled the “Full of Krapp newsletter.” I’m subscribed to dozens of newsletters. Kevin’s is by far one of my favorites. It’s part hysterical part informative take on the ridiculousness of modern life. Highly recommended.

We cover:

  • Comedy, what it is and why it matters
  • Kevin’s favorite comedians (and some of mine)
  • The outrageousness of outrage culture
  • People who get compared to Hitler who shouldn’t be compared to Hitler
  • Writing advice
  • Glue, horses, and how they’re (not) related
  • Criticism and how nobody avoids it (even Viktor Frankl)
  • The draconian California lockdown curfew
  • And loads more.

Please enjoy!

Listen on Spotify | Listen on iTunes | Watch on YouTube | Trailer


Every Sunday, I write a weekly newsletter full of advice for creatives, plus extra goodies like drafts of blog posts and previews of the podcast. Sounds good? Click here to subscribe and get the next issue delivered straight to your inbox on Sunday.

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Insight follows movement

Sitting by, waiting for insight to strike – that’s rarely a reliable strategy.

Insight follows movement. Insight comes when we pick the pen, put down our excuses, and begin to work. Even if the first three drafts suck (they usually do). And even if we fail to meet our expectations (we usually do).

It’s rare for anything I make to turn out as great as I wanted it to. But I can at least try to meet my expectations. I can at least try to put in the reps.

Because that’s all that matters.

Repetition. Repetition. Repetition.

Start moving. Start seeing. Start creating.

Personal newsletters are the new social media (and that’s a good thing)

I’m not on social media much these days. Not for the typical reasons, at least. Whenever I’m on Twitter, it’s usually because I’m promoting the podcast and videos. And if you see me on Facebook and LinkedIn, it’s not me. I ghost-post the blogs on Facebook and LinkedIn straight from WordPress.

But let’s consider Facebook. Facebook is for connecting with friends and family. It’s to see what everyone’s up to. But what it’s really about is to see what everyone thinks they should be up to. You know, staying on top of politics, frappuccinos, the perfect vacation, complaints about work, all that fun stuff.

Facebook is like fast food food photography. A photograph of a quarter pounder makes the burger look as sexy as Aldous Huxley, but in reality, it’s about as ugly as Arthur Schopenhauer. In other words, your life will never be as exciting as it appears on Facebook. The opposite is true: your life is not as depressing as you make it out to be on Facebook.

Anyways, newsletters. So, there’s all sorts of newsletters. We have personal newsletters, brand newsletters, corporate newsletters, my newsletter. Let’s look at the first one.

A personal newsletter is like a Facebook post worth reading. It’s generous because nobody asked the writer to share it. It’s high quality because the writer has a deadline. And it’s lacking all the stuff that makes Facebook a two-way attention vortex: no distracting sidebar, no noise, no signaling, no showing off, no hiding behind the mask of filters.

People who write personal newsletters hold themselves to a standard. Their goal? To get better at writing. Which means that they want to get better at thinking. (Facebook would be much better if its users applied this mindset.)

I learn more about someone’s current state-of-mind than I ever could from the typical Facebook post. All because of the generosity of the writer, the high bar of a deadline, and the missing cacophony of sidebars and infinite scroll.

A great personal newsletter writer considers only this question: what am I noticing?

Here’s some personal newsletters I’d recommend to anybody looking to bring some joy and curiosity to their week. All written by generous friends of mine.

Letter from A Learn-It-All — Jen Vermet’s thoughtful posts on the bravery of learning.

Thinking Out Loud — Cullin McGrath’s weekly writings on personal growth.

Quick Brown Fox — The original playground for adults. Salman Ansari connects ideas from poems, drawings, and animations.

Happy reading.