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Listen to the Best Podcast Episodes Dropped in 2020

Best Podcasts 2020

Have you noticed better and better podcasts out there?

This past year I listened to countless hours of conversations and reporting. While walking, cooking or just sitting, podcast conversations stimulate my brain in all sorts of ways. I treat podcasts like articles, so I listen to them in order of relevance or convenience. I found tons of great older podcasts this year, but this is a list from 2020.

This list includes the best ten podcasts from 2020 arranged by topic, plus a few bonus episodes at the end.

Conversations with Entrepreneurs

Sean McCabe on Caleb Wojcik Show (Feb 2020, 1h20m)

I enjoy the insights from the prolific author, designer and entrepreneur Sean McCabe. He soundly advises that people focus on digital products and think of physical products as a fun bonus. Physical products take lots of time and investment!

Content is the cost of entry. If you’re not making content online, you don’t exist in people’s minds.

— Sean McCabe (@seanwes)

Andrew Wilkinson on Below the Line with James Beshara (Apr 2020, 2h4m)

This great conversation between two incredibly successful startup founders taught me the value of working efficiently and making smart decisions. I also like Andrew Wilkinson’s advice to limit your calendar to one scheduled hour per day – if only we could all do that!

Guy Raz on Tim Ferriss Show (Sep 2020, 1h30m)

The host of one of my favorite podcasts, How I Built This, is fascinating and combines Biz School case studies with storytelling arcs. Guy explains how they designed the show’s intro music to imitate one of Beck’s most upbeat songs, to ensure that NPR listeners would know this show differs from the usual programing. And it works! I’m embarrassed how much the intro song pumps me up.

Best Podcasts by Authors and Creators

Art and Science of Listening – Kate Murphy on Good Life Project (Mar 2020, 1h9m)

The author of You’re Not Listening, Kate Murphy offers this simple advice to listen better:

How you respond is the measure of a good listener – are you supporting the conversation and encouraging elaboration?

— Kate Murphy

Ryan Holiday with Cal Newport (Sep 2020, 1h15m)

Two writers that I deeply admire discuss a wide variety of topics on this recently launched show, Deep Questions. Cal Newport answers one listener question on how to overcome writer’s block. He explains that everything is hard, so choose the hard things you enjoy doing, such as writing

Ta-Nehisi Coates on Ezra Klein Show (Jun 2020, 1h32m)

Two of my favorite authors bring an interesting perspective in their discussion of the Black Lives Matter Movement. One great idea is that people with the most power should be asked to practice non-violence.

There is a critical mass around the country that feel that George Floyd is their neighbor.

— Ta-Nehisi Coates

Casey Neistat on How I Built This (Feb 2020, 1h34m)

As one of the most successful people on YouTube, Casey Neistat has a very unique perspective on life and work. He tells the story from his time working at MIT and getting the first investment in his startup, Beme, which CNN eventually bought two years late.

Top Three Podcasts

Ben Greenfield on The Portal with Eric Weinstein (Feb 2020, 1h10m)

Despite the importance of our health, I find it easy to focus on learning and studying other things. It helped me to listen to a fitness guru talk about some simple steps to improve your health from what you eat to how you sleep.

Atul Gawande on Armchair Expert with Dax Shepard (Aug 2020, 1h31m)

Who knew Dax Shepard could be an incredibly interesting and insightful interviewer? This podcast has risen to the top of the charts this past year. I found the conversation with the surgeon-plus-writer to be very comforting and informative in a confusing time. Gawande also offers terrific writing at The New Yorker and I found his book The Checklist Manifesto to be invaluable when I read it in my 20’s.

Jeff Haden on How to Be Awesome at Your Job (Jun 2020, 45m)

A terrific podcast from Pete Mockaitis with interesting guests that are new to me. It’s the perfect length for a run or stroll at 45 min. This episode with Jeff Haden, author of The Motivation Myth, offers some great tips for increasing willpower and staying motivated to do the work you want to do.

Bonus Podcasts!

In addition to the 2020’s best podcasts for learning, I also enjoyed fun podcasts from comedians and poets. Check out these for a fun time contemplating, relaxing, or laughing.

Don’t ask Tig with Ira Glass (Aug 2020, 33m)

The comedian Tig Notaro invites the host of This American Life onto her show to discuss listener questions about falling in love with roommates and deodorant etiquette. Funny stuff!

Mary Oliver interviewed by Krista Tippett – On Being Podcast (Sep 2020, 50m)

Originally aired in 2015, Mary Oliver passed away in 2019 and this interview was re-released with updates in September. The renowned poet reads a few of her works and discusses her writing process, which involves walking through the woods with a notebook almost every day.

Conan Needs a Friend– Michael Che (Aug 2020, 1h6m)

This almost feels like the perfect medium for Conan. He just blabs and jokes and gets very silly. I laughed a lot during this conversation with Michael Che, the host of Weekend Update on Saturday Night Live.

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